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Lutsen, Mn Rental Property - Home - Nice - Dancing Bears Lodge
(1 Reviews)
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- Minimum stay:2 nights
- Sleeps:8
- Bedrooms:4
- Bathrooms:2
- Property type:House
- Internet:No
- Pets considered:Yes
- Wheel chair accessible:N/A
About the Property
House, 4 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 8-10)
Dancing Bears Lodge - your home away from home near the beautiful shores of Lake Superior. Located just minutes from the lifts at Lutsen Ski Hill and Golf Course, Dancing Bears Lodge is a quaint and rustic 4 bedroom, 2 bath home, accommodating up to 8 persons. This 'Up North' newly remodeled Lutsen rental home offers the convenience of all the North Shore has to offer. Less than a two hour drive from Duluth, Dancing Bears Lodge combines the magic of a remote getaway with the convenience of a nearby highway. Come stay with us and you will understand why Dancing Bears Lodge is considered Lutsen's best kept secret!
Keywords: Hiking, Ski, Snowmobile, Single Family Home Rental, Lutsen Rental
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Member since: 2011
Property Type
- House
House Rules
- Max. occupancy 8
- Pets Considered
Accommodation Type
- Vacation Rental
- Guests Provide Their Own Meals
Bedrooms: 4 Bedrooms, Sleeps 8, Beds for 8
Other Amenities
- House is on 5 acre wood lot, 3/10 of a mile from Lutsen Ski Resort
- CD Player
- DVD Player
- Satellite / Cable
- Stereo
- Marina
- Restaurants
Local Services & Businesses
- ATM/Bank
- Groceries
Leisure Activities
- Beachcombing
- Bird Watching
- Boating
- Scenic Drives
- Shopping
- Walking
- Wildlife Viewing
Location Type
- Rural
Sports & Adventure Activities
- Cross Country Skiing
- Cycling
- Fishing
- Fly Fishing
- Golf
- Hiking
- Hunting
- Kayaking
- Mountain Biking
- Rock Climbing
- Skiing
- Snowboarding
- Snowmobiling
- Dining Area
- Clothes Dryer
- Garage
- Linens Provided
- Mobile Phone
- Parking For RV/Boat/Trailer
- Washing Machine
- Wood Stove
- Cooking Utensils
- Dishwasher
- Kitchen
- Microwave
- Refrigerator
- Deck / Patio
- Outdoor Grill
Currency ConversionDates | Nightly | Weekend Night | Weekly | Monthly * | Event |
Base Rate 2 night min stay |
$199 | $225 Fri, Sat |
Don't forget your vacation protection! Get protected now
Adding our Vacation Protection services can make sure your getaway goes smoothly, no matter what. We offer Cancellation Protection and Damage Protection so you can truly relax.
The property's calendar has not been updated in over 72 months. You can contact the owner for availability or look for properties with confirmed availability
Car: Necessary
3/10ths of a mile from Lutsen Ski Area base.
Owner info
Year Purchased: 2009
About the owner: I am an outdoor enthusiast and love the North Shore.
Why the Owner Chose Tofte, MN, USA:
Because of our love of the North Shore and all the activities it has to offer, including skiing, snowmobiling, fishing, boating, hiking, kayaking, golfing and biking, we decided that we wanted a place where we could enjoy these favorite activities. The home is conveniently located to all of these activities.
The Unique Benefits at this House:
This four bedroom home is just 3/10 of a mile from the Lutsen Ski Resort, and just 2/10 of a mile from the snowmobile trails. Superio National Golf Course is just across the street. The nearest Lake Superior boat access is just 7 miles away. The beautiful town Grand Marais is just 17 miles away.
Contact us
Send email
- Primary: 612-910-0641
Links to more information:
- CLICK HERE - http://www.dancingbearslodge.com
- Click Here to see All My Rental Listings
Dancing Bears Lodge - Lutsen, MN Rental
Kitchen Area - Dancing Bears Lodge
Bunk Room - Dancing Bears Lodge
Living Area - Dancing Bears Lodge - Lutsen, MN
Bedroom - Queen - Dancing Bears Lodge
This listing was first published here in 2011.
Date last modified - Monday, March 27, 2017
Partner Offers
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- Home
- Business Opportunities
SM Technolgies
SM Technolgies
No. of Franchise Outlets: --
Investment: Rs. 2lac - Rs.5lac
S.M Technologies – global IT Consulting & Solutions Company has come up with franchise opportunity for you...Read On!
S.M Technologies is a well established business company, successfully entered in the global market in 2009, established its own brand & conquered the local & global market with its extra-ordinary strong presence on World Wide Web.
Our Software group offers solutions and services in the Technology segment and as a Technology-facilitator for Retail, Academic, Hotels, Industries, Travel and Trade segment for Internet, Applications and the Enterprise using Microsoft, J2EE and IBM technologies on Microsoft Operating Systems and other processor platforms.
SM Technologies is global IT Consulting & Solutions Company that has been providing high value-added business solutions to enterprises of all sizes. We specialize in the development of custom software applications, HR services and offshore software outsourcing services. Specifically, our company carries out custom programming, database design, client-server, e-business solutions and internet/intranet software application development.
Franchisee Prerequisite:
- Leadership experience in related field
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- The commitment and resources essential to market & represent our products to a swiftly expanding and diverse customer population
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Opportunity is available, contact now for franchise details...Hurry!
Thanks & Regards
S.M Technologies Team

subset: commoncrawl


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If you don't save at least the cost of your prescription card membership fee in one year, we'll give you the difference.1
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Membership fee required ($20 individual or $35 family per year). Persons receiving benefits from a Medicare or Medicaid program are ineligible. Program offers Member the right to purchase specified health care services from participating providers at a discounted rate. The average savings on purchases of a 90-day supply of a value-priced generic at: Tier 1 ($10) $50.41; Tier 2 ($20) $52.54; Tier 3 ($30) $118.08. The average savings for purchase of commonly prescribed quantities of covered: (i) brand name drugs is $31.16 and (ii) generics that are not value-priced is $21.79. Amount of the discount may vary based on type of item/service Member purchases but provider will not charge Member more than the discounted rate. Program does not make any payments to providers. Member is entirely responsible for paying discounted price to provider at time of service. Membership may be cancelled within 30 days of enrollment effective date for a full refund. To request: (i) a list of discounted services; (ii) a list of participating providers (name, city, state, specialty) and/or (iii) the full terms and conditions of the Program before joining, call 866-922-7312 or visit Walgreens.com/RxSavingsClub. WAGDCO, LLC, 104 Wilmot Rd., Deerfield, IL 60015 is a discounted medical plan organization regulated by State Insurance Commissioners.
The Program does not meet the minimum creditable coverage requirements under Mass. Gen. Law c. 111M and 956 CMR 5.00.
The Program is not a Medicare Prescription drug plan.
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1 If by the end of the 1-year membership, member has not achieved total savings on all eligible Pharmacy and Walgreens Bonus Program items and services purchased with the PSC card that is equal to or greater than membership fee, member is eligible for store credit equal to the difference between membership fee and the member's total savings. See our Terms and Conditions.
2 The average savings for purchase of commonly prescribed quantities of: (i) brand name drugs is $31.16 and (ii) covered generics that are not value-priced is $21.79.
3 Restrictions apply to earning and use of 10% bonus. See Terms and Conditions for more information.
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George Martens (jockey)
George Martens | |
Occupation | Jockey |
Born | September 23, 1958 Not found |
Career wins | 686 |
Major racing wins | |
Hill Prince Stakes (1975) Belmont Stakes (1981) |
Racing awards | |
Eclipse Award for Outstanding Apprentice Jockey (1976) | |
Significant horses | |
Summing, Key To Content, Cryptoclearance |
George Martens (born September 23, 1958) is a retired Champion jockey in American Thoroughbred horse racing best known for winning the 1981 Belmont Stakes, the third leg of the United States Triple Crown of Thoroughbred Racing.
In 1976, George Martens was the top rated apprentice jockey in the United States, voted the Eclipse Award as the country's Outstanding Apprentice Jockey. In 1981 he earned the most important win of his career when he rode Summing to victory in the Belmont Stakes.
Martens retired from riding in 1985 but returned to racing the following year. Following his permanent retirement, he has worked as an exercise rider at Belmont Park. Some of the horses he has prepped include Lemon Drop Kid, Touch Gold, Sharp Humor, and Colonial Affair.
- June 15, 1981 TIME magazine article on George Martens and his 1981 Belmont Stakes win
- September 17, 1987 New York Times article on George Martens
This American horse racing biographical article is a stub. You can help Wikipedia by expanding it. |


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La-Z-Boy Contract has specialized in commercial furniture since 1981 with a focus on healthcare. La-Z-Boy Contract was one of the first manufacturers to design/engineer a "true healthcare recliner." Specific healthcare applications are all areas in an Acute Care facility, including patient rooms, waiting areas, treatment, emergency room waiting areas, orthopedics, and NICU units. We also specialize in furniture for Surgery Centers, Oncology, and Dialysis Centers. In addition, you will find a complete offering of lobby/lounge furniture for healthcare, commercial office, and higher education.
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text: The Low Budget Action show By jeangell mean to be cheeezy in perpose! Funny traler for fake show! Published October 28, 2007 102 views More Info » Full Credits jeangell Uploader Additional Credits Additional Credits: Jesse Angell, Kaleb Lundberg, Edwin Stats & Data 2 Funny Votes 2 Die Votes 102 Views Published: October 28, 2007 Categories: Sketch Music Keywords: low budget Jesse Angell Kaleb Lundberg funny Trailer Up Next: Enigma Boy AUTOPLAY Up Next In: 10 Enigma Boy Young a Stranger The Light Weight Low-Budget James Bond Movie Follow Facebook Twitter Tumblr Instagram Browse Related Comments 4+ more View All ▶ jeangell Vaguely Related Videos Vaguely Related Pics & Words Advertisement Tags: low budget Jesse Angell Kaleb Lundberg Advertisement Featured Today More


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Apple Defies Trend Of Declining PC SalesWhile other major computer-makers saw shipments fall in 2015, Apple increased the number of Macs it shipped worldwide last year, according to estimates from two research firms on Tuesday.
$100 Google Chromebit Turns Any TV Into A Full ComputerThis summer, Google is unveiling a full computer that will cost less than $100. It looks like a memory stick or maybe a high-tech highlighter, but it's actually a full-fledged quad core processor computer with 16 gig hard drive and 2 gigs of ram. Just plug it into any TV with an HDMI port available.
Apple Posts 'Staggering' Quarterly Profit Of $18 Billion, Sells 74 Million iPhones, 21 Million iPadsApple said Tuesday that it sold 74.5 million iPhones during the three months that ended Dec. 31, beating analysts' expectations for the latest models of Apple's most popular gadget.
Apple Unveils New OS X Yosemite, iOS 8 At 25th Annual Worldwide Developers ConferenceApple's Mac operating system will have easier ways to share and search, while the iOS software for iPhones and iPads is getting new features for keeping tabs on your health and controlling home devices.
Apple Updates Operating System, Shows Off New Radio Service At SF ConferenceApple revealed a digital radio service and changes to the software behind iPhones and iPads during a keynote presentation Monday at the company's annual conference for software developers in San Francisco.
Apple Blocks Java On Macs Due To VulnerabilitiesSome Mac users were taken by surprise Thursday as their computers stopped running programs written using the Java programming language after Apple blocked Java due to security problems.
Apple Says 3 Million Copies Of OS X Mountain Lion Sold In 4 DaysApple said Mac users downloaded 3 million copies of Mountain Lion, its latest operating system, in the first four days it was available.
Orbitz Reportedly Steering Mac Users To Pricier HotelsThe move by Orbitz is part of the growing trend of online retailers tailoring their offerings based on a wide variety of available user data; in this case, they targeted the hardware used by the shopper.
Apple Expected To Showcase New Macs, Software In SF MondayApple CEO Tim Cook is expected to show off new iPhone software, updated Mac computers and provide more details on future releases of Mac software when he kicks off the company's annual conference for software developers on Monday.
Tech Report: Apple Products Seen In Half Of U.S. HomesKCBS Technology Analyst Larry Magid looks at a new report that shows just how widespread the ever-growing popularity of Apple products are in the U.S.
Tech Report: Steve Jobs Remembered As Private, InnovativeWhile Apple co-founder Steve Jobs is remembered as a visionary, Larry Magid says he was also a very private person, seldom giving one-on-one interviews.
Tech Report: Macintosh Reaches Critical Mass For Malware AttackAn old trick that's beguiled Windows users for years has become a growing threat on Macintosh machines.


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Thursday, November 3, 2005
September 10, 2005
Mixing it up and trying players in different positions was the name of the game for the Hood River Valley High School girls' varsity soccer team, as they started their 14-game season on Thursday afternoon at home against Cleveland High School. Sporting spotless, bright white jerseys, the girls made a good showing, despite an eventual 4-0 loss against a bigger, more physical Cleveland squad.
"It was a good pre-season game," Coach Joe Kelly said. "It lets us know were we are. And that's what this is all about right now, it's getting girls exposure to that kind of play. These non-league games are more about exposure and playing time for certain players in different positions. It's not about going out and doing whatever you have to do to win. It's really about getting players some experience in different positions."
The girls started the game on a tough note, with Cleveland scoring two goals in the first ten minutes and another shortly after.
After halftime, the Eagles showed far greater field presence. They controlled the midfield better, pushed forward more collectively, and cleared the ball better on defense. Kelly attributed the second half improvement to the girls playing positions they were more comfortable with.
"We're experimenting still, and the girls have been great about that," Kelly said. "They're willing to switch around positions a bit and play in places that they're not used to. They have responded well by being real positive about that."
The girls have five more games before their first league match at Bend High School on Oct. 14.
Varsity roster
Seniors: #
Kaitlin Bauld 0
Markee Cox -
Emily McCallum 1
Jessica McMorran 3
Kelly Durkan 16
Heather Van Swaay 15
Diana Hernandez 7
Juniors: #
Kayla Lloyd 10
Justine Bryant 2
Meredith Danko 11
Jessica Ostler 13
Jill Chance 4
Sara Desitter 8
Katie Rawson 5
Sophomores: #
Jennifer Hanners 17
Lindsay Halliday 12
Sadie Dallman 9
Dani Lichty 6
Upcoming games
Monday, Sept. 12
Home vs. Southridge, 4 p.m.
Thursday, Sept. 15
Home vs. Reynolds, 4 p.m.
Tuesday, Sept. 20
Away vs. St. Helens, 4 p.m.
Thursday, Sept. 22
Away vs. Milwaukie, 7 p.m.
Tuesday, Sept. 27
Home vs. Sam Barlow, 4 p.m.
Friday, Sept. 30
Away vs. Bend, 4 p.m
More like this story
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Parkdale third graders sing "12 Disaster Days of Christmas"
Welcome to your sing-able Christmas gift list. What follows is an emergency rendition of "12 Days of Christmas" – for outfitting your home or car in case of snow storm, earthquake, flood or other emergency. Read it as a simple list, or sing it to the tune of "12 Days" – you know, as in " … and a partridge in a pear tree…" Not to make light of it, but the song is a familiar framework for a set of gift ideas that you could consider gathering together, even if the recipient already owns items such as a bunch of coats, tire chains and flashlights. Stores throughout the Gorge are stocked up on all these items. Buying all 12 days might be prohibitive, but here are three ideas for checking any of the dozen off your list (notations follow, 1-12.) The gift items needed to stay warm, dry and safe are also coded to suggest items in your abode (A) in your car (C) or both (B). 12 Gallons of Water (A) 11 Family meals (B) 10 Cans of propane (A) 9 Hygiene bags (B) 8 Packs of batteries (A) 7 Spare coats (B) 6 Bright red flares (C) 5 Cozy blankets (B) 4 Tire chains (C) 3 Flashlights (B) 2 cell phone chargers (B) 1 And a crush-proof first aid kit (B) Price ranges? Here's a few quotes for days Three, Two, Four and Nine: n A family gift of flashlights (three will run $15-30, Hood River Supply, Tum-A-Lum) n Cell phone chargers (two will run $30-60) n Tire chains (basic set, $30, Les Schwab, returnable if unused for the winter) n Family meals ($100 or so should cover the basics for three or four reasonably well-fed days) n The home kit should be kept in a handy place near an exit, and remember that water needs to be replenished every few months. If you have a solid first aid kit already, switch out the gift idea with "and-a-sto-o-u-t- tub-for it-all …" Otherwise, it's a case of assembling your home or car kits and making sure all members of the family know what the resources are and how to use them (ie flares and propane). Emergency situations are at worst life-threatening, at best deeply uncomfortable if you and your family are left without power for an extended period, or traveling and find yourself in a situation where you need to wait out a storm, lengthy traffic delay, or other crisis. Notes on the 12 gift ideas: 12 – Gallons of water: that's one per person in a four-member family to last for three days, the recommended minimum to be prepared for utility outages. 11 – Easy-open packaged goods, energy bars, dried food and nuts are good things to include for nutrition. Think of what your family of four needs for three days to stay fortified and hydrated (see number 12). Can-opener also recommended 10 – If you have a propane camping stove, keep extra fuel handy. 9 – Hygiene bags: put packaged moistened towelettes, toilet paper, and plastic ties in large garbage bags (for personal sanitation) Resource list courtesy of Hood River County Emergency Management, Barbara Ayers, manager/ 541-386-1213. The county also reminds residents to Get a Kit, Make A Plan to connect your family if separated, and Stay Informed. See www.co.hood-river.or.us to opt-in for citizen alerts. Enlarge


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skipvia commented on the word luncheon meats
See luncheon. Also see the Fake Food and Luncheon Meats lists.
March 13, 2008


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When applied by itself, rarely works. However, security through obscurity can be effective if applied in conjunction with normal security procedures. If you don't tell anyone about that login port, folks are less likely to try it. But you better have a password on it for the fool who happens upon it. See Making things foolproof results in better fools.
There is no way to measure the number of security holes in existence that are protected by nothing more than an algorithm known only to the the author. One sure fact is that hackers do decipher some of these messes and find the exploits, for good or evil.
All public key cryptography systems that I am familiar with also rely on some form of obscurity. Everyone assumes that the algorithm to decrypt a message from its cipher text and public key is computationally infeasible. As far as I know, no public key system has proven the lack of existence of a "back-door."
Consider RSA as an example. It's so called strength comes from the difficulty of factoring large numbers, specifically the public key n=p*q, where p and q are prime. But it has some known weaknesses for otherwise valid values of p and q: p and q must have very different values, (p-1),(p+1),(q-1),(q+1) can not be products of small primes. RSA key generators check for these cases before issuing a key pair. But nobody knows what other weaknesses may exist, hidden in the obscurity of mathematics! An algorithm to quickly factor any p*q may exist, but humans did not create mathematics and can not search its blueprints for a hole. Quantum computers promise to crush RSA by changing the fundamental order in which the product of two primes can be factored.
Smart cards have me worried. They rely on public key cryptography to protect real money. Banks are willing to trust cryptography to store value in the real world. If a security hole is found who knows what will happen? And holes will be discovered. But will they be publicized or kept in obscurity? What would you do if you were working at the IBM lab that finally creates a working implementation of a quantum computer and could bring down an entire monetary infrastructure?
Maybe sometimes security through obscurity is the best we can hope for.
It's not just public key cryptosystems that aren't proven secure. Neither are virtually all symmetric algorithms. But if you take RSA; it is an algorithm that has been around for many years and based on one of the oldest problems in mathematics (finding prime factors). I'd lay more money on RSA being secure than on Rjindael; but frankly with the amount of research and study that goes into both, I don't believe an exploitable weakness will occur in either any time soon.
By contrast, security through obscurity is when you don't really have any security at all, but you just hide the weakness. A canonical example is having your root account named fred instead, with an easy to remember password. Or writing your own encryption algorithm and using it with no peer review, and thinking it is more safe to use than an open algorithm. The concept of backdoor in the context of security through obscurity refers to intentionally laid backdoors. You seem be calling exploitable weaknesses in algorithms backdoors.
security through obscurity
(alt. `security by obscurity') A term applied by hackers to most OS vendors' favorite way of coping with security holes -- namely, ignoring them, documenting neither any known holes nor the underlying security algorithms, trusting that nobody will find out about them and that people who do find out about them won't exploit them. This "strategy" never works for long and occasionally sets the world up for debacles like the RTM worm of 1988 (see Great Worm), but once the brief moments of panic created by such events subside most vendors are all too willing to turn over and go back to sleep. After all, actually fixing the bugs would siphon off the resources needed to implement the next user-interface frill on marketing's wish list -- and besides, if they started fixing security bugs customers might begin to expect it and imagine that their warranties of merchantability gave them some sort of right to a system with fewer holes in it than a shotgunned Swiss cheese, and then where would we be?
Historical note: There are conflicting stories about the origin of this term. It has been claimed that it was first used in the Usenet newsgroup comp.sys.apollo during a campaign to get HP/Apollo to fix security problems in its Unix-clone Aegis/DomainOS (they didn't change a thing). ITS fans, on the other hand, say it was coined years earlier in opposition to the incredibly paranoid Multics people down the hall, for whom security was everything. In the ITS culture it referred to (1) the fact that by the time a tourist figured out how to make trouble he'd generally gotten over the urge to make it, because he felt part of the community; and (2) (self-mockingly) the poor coverage of the documentation and obscurity of many commands. One instance of deliberate security through obscurity is recorded; the command to allow patching the running ITS system (escape escape control-R) echoed as $$^D. If you actually typed alt alt ^D, that set a flag that would prevent patching the system even if you later got it right.
--The Jargon File version 4.3.1, ed. ESR, autonoded by rescdsk.
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This is an exciting adventure of four 12 year olds. These boys and girls must save the world from destruction. Only they must do it as tiny lizards to avoid detection. Once changed into tiny lizards with genetic technology they are dropped deep inside the rain forest jungle. In the deep rain forest jungle they must face great dangers just to get to the hidden hideout. Then they must defeat the evil terrorists to save the free world. Who will survive!? Will they defeat the evil terrorists!? Will they just become lunch!?
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The routine roll call at the Presidio stockade in San Francisco was disrupted last October. Linking arms and singing We Shall Overcome, 27 Army prisoners staged a sitdown protest. An hour later, they were hauled off to their cells, charged with mutiny one of a baker's dozen of crimes ranging from murder to rape punishable by death under the Uniform Code of Military Justice.
At the outset of their mass trial, a seven-man court-martial board was told by the presiding law officer that it was a "nonviolent mutiny." Maximum pen alty: life in prison. To simplify defense procedures, the...
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President Barack Obama's budget this week makes clear the real political equilibrium in the US. The federal government is shrinking. Discretionary spending in the new Obama budget would shrink to 4.9 per cent of gross domestic product in 2023, compared with 7.9 per cent of GDP in 2008. Both parties have signed on to this shrinkage. Neither will try to stop it.
The implications are enormous. Until 2017 at the earliest, there is likely to be no or very meagre action to address America's growing underclass, gaping inequalities, decrepit infrastructure, persistent drought or worsening climate change. Slow growth, unemployable young people, a vast incarcerated minority population and gaudy excesses at the top will remain the norm. Even Mr Obama's few new initiatives, for example for early childhood development and new infrastructure, are tiny drops in America's ocean of unmet need.
Read the full article at the Financial Times or the PDF here
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Publication number | US6663958 B2 |
Publication type | Grant |
Application number | US 10/077,657 |
Publication date | Dec 16, 2003 |
Filing date | Feb 15, 2002 |
Priority date | Jun 20, 2001 |
Fee status | Paid |
Also published as | DE10129611A1, EP1270701A2, EP1270701A3, EP1270701B1, US20030013790 |
Publication number | 077657, 10077657, US 6663958 B2, US 6663958B2, US-B2-6663958, US6663958 B2, US6663958B2 |
Inventors | Marc Husemann, Stephan Zöllner |
Original Assignee | Tesa Ag |
Export Citation | BiBTeX, EndNote, RefMan |
Patent Citations (15), Referenced by (7), Classifications (16), Legal Events (6) | |
External Links: USPTO, USPTO Assignment, Espacenet | |
The invention relates to pressure sensitive adhesives based on block copolymers, said block copolymers comprising at least the unit P(A)-P(B)-P(A), composed of a middle polymer block P(B) and of two polymer blocks P(A) surrounding the middle polymer block P(B), or the unit P(B)-P(A)-P(B), composed of a middle polymer block P(A) and of two polymer blocks P(B) surrounding the middle polymer block P(A), to the use of such adhesives, and to a process for preparing them.
In industry, hotmelt processes operating with solventless coating technology are of growing importance in the preparation of pressure sensitive adhesives. In general, environmental regulations and increasing costs are forcing forward the development process of such adhesives. Besides SIS (styrene-isoprene-styrene copolymers) systems, acrylic polymers are increasingly being applied from the melt as a polymer film to backing materials. Moreover, for specialty applications, pressure sensitive adhesive tapes which feature very low outgassing are needed. This is something which can be ensured only by means of hotmelt processes, since conventional coatings applied from solution always still contain small fractions of residual solvent.
Additionally, there is a growing need for acrylic pressure sensitive adhesives on apolar surfaces. In industry, the use of plastics is on the increase, owing to the weight reduction they offer as compared with conventional metals, and, accordingly, more and more adhesive bonds are being formed on these substrates. Since the large number of their ester groups makes polyacrylates relatively polar, bond strength can be increased only by using resins of similar polarity. Although these resins exhibit good bond strength on polar surfaces such as steel, their bond strengths to apolar surfaces are merely moderate, which is inadequate for the majority of applications.
U.S. Pat. No. 4,418,120 A describes crosslinked pressure sensitive adhesives comprising rosin ester resins, which possess good bond strength to polypropylene. Owing to the unsaturated nature of the resin, however, the UV stability of these adhesives is poor. The bond strengths to the apolar surfaces as well are relatively low.
U.S. Pat. No. 4,726,982 A describes crosslinked pressure sensitive adhesives featuring high bond strength to inks and paints. The copolymers of acrylic esters and N-vinyl-2-pyrrolidone are blended with tackifiers such as poly(isobornyl methacrylate), pentaerythritol esters of rosins, and mixed aliphatic/aromatic resins.
Here again, relatively polar resins are used to increase the bond strength to apolar surfaces. The tackifiers mostly described, however, possess unsaturated compounds which, in the hotmelt process, can lead to instances of gelling; additionally, after bonding, the unsaturated compounds undergo aging or weathering under UV light and, accordingly, the adhesive properties suffer over a prolonged period of time.
In EP 0 707 604 A1, polyethylene/butylene macromonomers are used for copolymerization with acrylates. As a result, phases are formed which have a low glass transition temperature, which in turn allow the adhesives to flow on apolar surfaces and thus ensure high bond strengths to PE and PP. A disadvantage is the poor conversion of the polymerization process described. Furthermore, the macromonomers are copolymerized randomly, and so no domains are able to form. Such domains would offer regions in which even very apolar resins would be soluble. With these pressure sensitive adhesive tapes, therefore, only a relatively low bond strength to apolar surfaces is attained.
Furthermore, the polyacrylates described are very difficult to process as hotmelts because the high residual monomer fractions impact negatively on the concentration process, and migration within the pressure sensitive adhesive tape can have an adverse effect on the long-term adhesive properties.
In contrast, styrene-isoprene-styrene (SIS) block copolymers are widespread as elastomers for hotmelt-processable pressure sensitive adhesives [preparation processes: U.S. Pat. No. 3,468,972 A; U.S. Pat. No. 3,595,941 A; use in pressure sensitive adhesives: U.S. Pat. No. 3,239,478 A;
U.S. Pat. No. 3,935,338 A] with high bond strength to apolar surfaces. Their effective processability is achieved by means of a relatively low molecular weight and by means of a specific morphology [EP 0 451 920 B1]. These pressure sensitive adhesives can be crosslinked very effectively with UV light in the presence of photoinitiators or with electron beams, since the middle blocks contain a large number of double bonds.
Nevertheless, these elastomers are not without their disadvantages, such as, for example, severe aging under UV light (i.e., in daylight too) and in an oxygen/ozone atmosphere. Another very unfavorable property for application is the relatively low thermal shear strength. These pressure sensitive adhesives, accordingly, are unsuited to relatively long-term, outdoor bonding applications and to applications within relatively high temperature ranges. Moreover, owing to the formation of domains of the hard polystyrene end blocks, effective flow on apolar surfaces is prevented. The same applies to other block copolymers which possess a middle block containing at least one double bond [U.S. Pat. No. 5,851,664 A].
A solution to the aging problems, the hotmelt processability, the high cohesion, and the efficient radiation-chemical crosslinking is offered by the combination of SIS polymers and polyacrylates.
U.S. Pat. No. 5,314,962 A describes A-B-A block copolymers as elastomers for adhesives, which possess A domain formation as their cohesion-forming feature. As a result of the selection of the comonomers used, however, only low bond strengths can be realized on apolar surfaces. Additionally, these polymers are not compatible with highly apolar resins.
EP 0 921 170 A1 describes A-B-A block copolymers which have been modified with additions of resin. Here again, owing to the selection of the comonomers and added resins, only poor bond strengths can be realized on apolar surfaces.
EP 0 408 429 A1 and EP 0 408 420 A1 described A-B-A block copolymers which, however, were synthesized by living anionic polymerization. Because of the absence of an acrylic acid fraction, however, these polymers are unsuited to use as pressure sensitive adhesives, since the internal cohesion of the middle block is too low and an at least lower fraction of polar monomers is required for bonds to steel. Because of the anionic polymerization, it is not possible to use acrylic acid comonomers or other hydroxyl-functionalized acrylate comonomers, such as hydroxyethyl acrylate, for example.
In U.S. Pat. No. 5,166,274 A, this deficiency is compensated by hydrolyzing block copolymers of tert-butyl methacrylate in order to liberate the carboxylic acid function. On the industrial scale, however, this method cannot be applied to pressure sensitive adhesives, since the hydrolysis step is very costly and time consuming.
In U.S. Pat. No. 6,069,205 A1, diblock and triblock copolymers are prepared by an atom transfer polymerization and utilized for adhesives. This method is also unsuitable for preparing pressure sensitive adhesives, since it uses relatively high catalytic amounts of heavy metal compounds which would have to be removed, in a cumbersome operation, by extraction processes.
EP 1 008 640 A1 describes styrene block copolymers comprising an acrylate middle block composed, however, of the common C2 to C14 alkylacrylates. Because of the restriction of the comonomers and, associated therewith, the restriction of the resins which can be used, only low bond strengths to apolar substrates are achievable with these polymers. Moreover, metal salts are used to prepare these polymers too (in analogy to U.S. Pat. No. 6,069,205 A), which would have to be removed, again a cumbersome operation, for pressure sensitive adhesive tape applications.
It is an object of the invention to provide improved pressure sensitive adhesives based on polyacrylate which do not have the disadvantages of the prior art, or in which said advantages are reduced, and which, therefore, exhibit good cohesion even in the uncrosslinked state and possess very high bond strengths to apolar surfaces. Further desirable qualities are minimal change on aging, and suitability particularly for processing by the hotmelt process and for use as a hotmelt adhesive.
This object is achieved by the pressure sensitive adhesives of the invention as specified in the main claim. The subclaims relate to improved embodiments of these pressure sensitive adhesives, to a process for preparing them, and to their use.
The invention accordingly provides a pressure sensitive adhesive based on block copolymers, said block copolymers having at least one unit composed of three successive polymer blocks, said three successive polymer blocks being chosen in alternation from the group of the polymer blocks P(A) and P(B), wherein
P(A) represents a homopolymer or copolymer block obtainable from a component A which is composed of at least two monomers A1, A2, the polymer block P(A) having a softening temperature of from −80° C. to 0° C.,
at least one (A1) of the monomers of component A is an acrylic or methacrylic acid derivative of the general formula
in which RI═H or CH3 and RII is in particular a branched or unbranched, cyclic, saturated or unsaturated, substituted or unsubstituted alkyl radical having from 1 to 20, with particular preference from 4 to 14, carbon atoms,
at least one further (A2) of the monomers of component A is an acrylated macromonomer of the general formula
in which RIII═H or CH3 and RIV is an aliphatic, linear or branched or cyclic, unsubstituted or substituted alkyl radical having more than 30 carbon atoms, the average molecular weight Mn (numerical average) of said at least one macromonomer being between 492 g/mol (30 carbon atoms) and 30 000 g/mol,
P(B) represents a homopolymer or copolymer block obtainable from a component B which is composed of at least one monomer B1, the polymer block P(B) having a softening temperature of from 20° C. to 175° C., and
the polymer blocks P(A) are not homogeneously miscible with the polymer blocks P(B).
Accordingly, the block copolymers of the inventive pressure sensitive adhesive comprise at least the unit P(B)-P(A)-P(B) composed of a middle polymer block P(A) and of two polymer blocks P(B) enclosing the middle polymer block P(A), and/or the structural unit which is inverse to this, i.e., at least the unit P(A)-P(B)-P(A) composed of a middle polymer block P(B) and of two polymer blocks P(A) enclosing the middle polymer block P(B), subject to the above-described provisos for the polymer blocks P(A) and P(B).
The block copolymers for the pressure sensitive adhesive of the invention can be prepared and used to advantage in a very wide variety of structures. Explicitly, reference may be made to linear or branched chains of the polymer blocks P(A) and P(B), corresponding for example to a general structure [P(A)-P(B)]n, to star polymers of P(A) and P(B), corresponding for example to the general structures [[P(A)-P(B)]n]mX or [[P(B)-P(A)]n]mX or [[P(A)-P(B)]n]mX[P(A)-P(B)]p] q, or to the general structures [[P(A)-P(B)]n]mXLp or [[P(B)-P(A)]n]mXLp, in which L here can denote different radicals. The enumeration of these structures is intended only by way of example, without representing any limitation. The structures also embrace all of the "asymmetric" structures in which all of the polymer blocks P(A) and P(B) meet per se the definitions set out above, but in which the indices n, m, p and q imply only the multiple occurrence of the individual units but not their chemical or structural identity. L can with preference be radicals which, for example, represent poly(meth)acrylates but which do not inherently have a block structure. Also included here are homopolymers of the components A or B.
In one advantageous further development of the invention, at least one vinyl compound containing functional groups is used additionally as monomer A3 for component A.
One particularly advantageous embodiment of the invention features the following composition of component A:
from 35 to 97% by weight acrylic acid and/or methacrylic acid derivatives corresponding to monomer A1,
from 3 to 40% by weight macromonomers corresponding to monomer A2,
from 0 to 25% by weight vinyl compounds corresponding to monomer A3.
In a very advantageous procedure, the monomers chosen for component A are acrylic and/or vinyl monomers which lower the glass transition temperature of the block P(A)—alone or in combination with further monomers for component A—to below 0° C.
As monomers A1 it is preferred to use one or more compounds described by the general formula (I) in which RI═H or CH3 and the radical RII is chosen from the group consisting of aliphatic linear, branched or cyclic, substituted or unsubstituted, saturated or unsaturated alkyl radicals having from 4 to 14, preferably from 4 to 9, carbon atoms.
Preferred examples of monomers A1 are n-butyl acrylate, n-pentyl acrylate, n-hexyl acrylate, n-heptyl acrylate, n-octyl acrylate, n-nonyl acrylate and their branched isomers, such as 2-ethylhexyl acrylate, for example. Furthermore, the methacrylates corresponding to the abovementioned acrylates are among preferred examples of the monomers A1. Compounds which lend themselves outstandingly to use as monomers A1 are, additionally, isobutyl acrylate, isooctyl acrylate, and isobornyl acrylate.
For the monomer A2 it is preferred to use hydrogenated ethylene/propylene macromonomers and/or hydrogenated ethylene/butylene macromonomers which possess a softening temperature of not more than 0° C. and carry an acrylate or methacrylate function as end group. One very preferred example used is Kraton L-1253™ (Shell AG). Kraton Liquid L-1253™ (Shell AG) is a macromonomer having a molecular weight of 4000 g/mol, is methacrylate functionalized, and possesses a saturated poly(ethylene/butylene) unit as aliphatic side chain.
In a procedure which is very advantageous in the sense of the invention, the macromonomers used comprise aliphatic acrylates, such as triacontanyl acrylate, and also higher homologs.
Vinyl compound monomers A3 are all monomers containing a vinylogous double bond capable of polymerization, especially those in which this double bond is activated for polymerization by functional groups. In this sense it is also possible to classify (meth)acrylates within the group of the vinyl monomers.
In one very advantageous embodiment of the invention, at least one of the monomers of component A, especially at least one of the monomers A3, is chosen such that it contains one or more functional groups which can be used for a crosslinking reaction of the block copolymers, especially for a thermal or radiation-chemical crosslinking, and, very particularly, for a crosslinking which is induced and/or assisted by UV radiation or by irradiation with electron beams.
With particular advantage, these can be (meth)acrylic derivatives containing unsaturated alkyl radicals in the radical RVI, of the general formula
in which RV═H or CH3. Preferred for RVI are alkyl radicals having from 3 to 14 carbon atoms which contain at least one C—C double bond. For acrylates modified with double bonds, allyl acrylate and acrylated cinnamates are particularly advantageous.
In one advantageous variant of the pressure sensitive adhesive of the invention, it is also possible to use acrylic monomers of the general formula (III) in which the group —ORVI represents another functional group for crosslinking of the adhesive or comprises two or more further and/or different functional groups for crosslinking of the adhesive. Moreover, it is also possible, very advantageously, to use as monomers A3 vinyl compounds having further double bonds which do not react during the (radical) polymerization. Particularly preferred examples are isoprene and butadiene.
Preferred examples of monomers A3 further include vinyl acetate, acrylamides, photoinitiaters functionalized with at least one double bond, tetrahydrofuryl acrylate, hydroxy-functionalized (meth)acrylates, carboxyl-functionalized (meth)acrylates, amine- or amide-functionalized (meth)acrylates, and also vinyl esters, vinyl ethers, vinyl halides, vinylidene halides, vinyl compounds containing aromatic ring systems and heterocyclic systems in α position, especially vinyl acetate, vinylformamide, vinylpyridine, ethyl vinyl ether, vinyl chloride, vinylidene chloride, and acrylonitrile.
As monomers A3 it is also possible to use, with advantage, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl ethacrylate, acrylic acid, methacrylic acid, allyl alcohol, maleic anhydride, itaconic anhydride, itaconic acid, benzoin acrylate, acrylated benzophenone, acrylamide, and glyceridyl methacrylate.
In another very advantageous embodiment of the inventive pressure sensitive adhesive, functional groups capable of crosslinking are introduced which are capable of a crosslinking reaction under the effect of thermal energy. Greatly preferred in this context are hydroxyl, carboxyl, epoxy, amide, isocyanato or amino groups.
Said at least one monomer B1 is preferably chosen such that the polymer blocks P(B) are capable of forming a two-phase domain structure with the copolymer blocks P(A). Advantageous examples used as monomers for component B are vinylaromatics, methyl methacrylates, cyclohexyl methacrylates, and isobornyl methacrylates. Particularly preferred examples are methyl methacrylate and styrene.
It has been found particularly advantageous for the invention if the block copolymers have an average molecular weight Mn (numerical average) of between 5 000 and 600 000 g/mol, in particular between 80 000 and 450 000 g/mol.
The fraction of the polymer blocks P(B) is preferably between 10 and 60% by weight, in particular between 15 and 40% by weight, of the overall block copolymers.
The invention additionally provides a process for preparing the inventive pressure sensitive adhesive, in which the block copolymer is prepared by a trithiocarbonate-controlled radical polymerization.
For preparing the block copolymers used for the pressure sensitive adhesives of the invention, it is also possible in principle, however, to use any polymerization which proceeds in accordance with a controlled-growth radical mechanism, such as, for example, ATRP (atom-transfer radical polymerization) or nitroxide/TEMPO controlled polymerization or, more preferably, the RAFT process (rapid addition-fragmentation chain transfer).
The polymerization can be conducted in the presence of an organic solvent or in the presence of water, or in mixtures of organic solvents and/or water, or else without solvent. It is preferred to use as little solvent as possible. Depending on conversion and temperature, the polymerization time is between 6 and 72 hours.
In the case of solution polymerization, the solvents used are preferably esters of saturated carboxylic acids (such as ethyl acetate), aliphatic hydrocarbons (such as n-hexane or n-heptane), ketones (such as acetone or methyl ethyl ketone), special boiling point spirit, aromatic solvents such as toluene or xylene, or mixtures of these solvents. For polymerization in aqueous media or in mixtures of organic and aqueous solvents, it is preferred to add emulsifiers and stabilizers for the polymerization. Polymerization initiators used are customary radical-forming compounds such as, for example, peroxides, azo compounds, and peroxosulfates. Initiator mixtures are also outstandingly suitable.
For the purpose of radical stabilization, nitroxides of type (IVa) or (IVb) are used:
in which R1, R2, R3, R4, R5, R6, R7, and R8 independently of one another denote the following compounds or atoms:
i) halides, such as chlorine, bromine or iodine
ii) linear, branched, cyclic, and heterocyclic hydrocarbons having from 1 to 20 carbon atoms, which can be saturated, unsaturated, and aromatic,
iii) esters —COOR9, alkoxides —OR10 and/or phosphonates —PO(OR11)2, in which R9, R10 and R11 are radicals from group ii).
The compounds (IVa) or (IVb) may also be attached to polymer chains of any kind and can therefore be used for constructing the block copolymers, as macroradicals or macroregulators.
As controlled regulators for the polymerization it is more preferred to use compounds of the following types:
2,2,5,5-tetramethyl-1-pyrrolidinyloxyl (PROXYL), 3-carbamoyl-PROXYL, 2,2-dimethyl-4,5-cyclohexyl-PROXYL, 3-oxo-PROXYL, 3-hydroxylimine-PROXYL, 3-aminomethyl-PROXYL, 3-methoxy-PROXYL, 3-t-butyl-PROXYL, 3,4-di-t-butyl-PROXYL
2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), 4-benzoyloxy-TEMPO, 4-methoxy-TEMPO, 4-chloro-TEMPO, 4-hydroxy-TEMPO, 4-oxo-TEMPO, 4-amino-TEMPO, 2,2,6,6,-tetraethyl-1-piperidinyloxyl, 2,2,6-trimethyl-6-ethyl-1-piperidinyloxyl
N-tert-butyl 1-phenyl-2-methylpropyl nitroxide
N-tert-butyl 1-(2-naphthyl)-2-methylpropyl nitroxide
N-tert-butyl 1-diethylphosphono-2,2-dimethylpropyl nitroxide
N-tert-butyl-1-dibenzylphosphono-2,2-dimethylpropyl nitroxide
N-(1-phenyl-2-methylpropyl) 1-diethylphosphono-1-methylethyl nitroxide
di-t-butyl nitroxide
diphenyl nitroxide
t-butyl t-amyl nitroxide.
As a further controlled polymerization method, use is made of atom transfer radical polymerization (ATRP), in which preferably monofunctional or difunctional secondary or tertiary halides are used as initiators and the halide(s) is (are) abstracted using complexes of Cu, Ni, Fe, Pd, Pt, Ru, Os, Rh, Co, Ir, Cu, Ag or Au [EP 0 824 111 A1; EP 0 826 698 A1; EP 0 824 110 A1; EP 0 841 346 A1; EP 0 850 957 A1]. The various possibilities of ATRP are described further in the documents U.S. Pat. No. 5,945,491 A, U.S. Pat. No. 5,854,364 A, and U.S. Pat. No. 5,789,487 A.
The P(B)-P(A)-P(B) block copolymer can also be prepared by anionic polymerization. In this case the reaction medium used preferably comprises inert solvents, such as aliphatic and cycloaliphatic hydrocarbons, or else aromatic hydrocarbons, for example. The living polymer is generally represented by the structure P(B)-M, in which M is a metal from Group I of the Periodic Table, such as lithium, sodium or potassium, for example. The molecular weight of the polymer is determined by the ratio of initiator to monomer. In order to construct the block structure, the monomers for block P(A) are added, after which the monomer(s) for block P(B) is (are) added in order to prepare the polymer block P(B)-P(A)-P(B). Alternatively, P(B)-P(A)-M can be coupled by a suitable difunctional compound. In this way, star block copolymers [P(B)-P(A)]nX are also obtainable. Examples of suitable polymerization initiators include n-propyllithium, n-butyllithium, 2-naphthyllithium, cyclohexyllithium and octyllithium, without wishing this enumeration to constitute any unnecessary restriction.
Furthermore, it is also possible to use difunctional initiators, such as 1,1,4,4-tetraphenyl-1,4-dilithiobutane or 1,1,4,4-tetraphenyl-1,4-dilithioisobutane. Coinitiators can also be used. Examples of suitable coinitiators include lithium halides, alkali metal alkoxides, and alkylaluminum compounds.
As a very preferred variant, the RAFT process (reversible addition-fragmentation chain transfer) is carried out. The process is described in detail in the documents WO 98/01478 A1 and WO 99/31144 A1. Suitable with particular advantage for preparing block copolymers are trithiocarbonates [Macromolecules 2000, 33, 243-245], in which case, in a first step, monomers for the end blocks B are polymerized and, in a second step, the middle block A is polymerized. Following the polymerization of the end blocks, the reaction can be terminated and reinitiated. It is also possible to carry out polymerization sequentially without interrupting the reaction. In one very advantageous variant, the trithiocarbonate (V) is used for the polymerization:
In the process for preparing the pressure sensitive adhesives of the invention, the solvent is removed under reduced pressure preferably in a concentrative extruder. This is done using, for example, single-screw or twin-screw extruders which distill off the solvent preferentially. Twin-screw extruders may be operated with advantage in corotating or counterrotating mode.
For its advantageous further development, up to 50% by weight, in particular from 20 to 40% by weight, of resins are added to the pressure sensitive adhesive of the invention. Examples of resins used include terpene resins, terpene-phenolic resins, C5 and/or C9 hydrocarbon resins, pinene resins, indene resins and/or rosins, alone or in combination with one another. In principle it is possible to use any resins which are compatible with the corresponding polyacrylate middle block P(A); in particular, mention may be made of all aliphatic, aromatic and alkylaromatic hydrocarbon resins, hydrocarbon resins based on pure monomers, hydrogenated hydrocarbon resins, functional hydrocarbon resins, and natural resins.
In a preferred procedure it is further possible to add additives, particularly crosslinkers, aging inhibitors, light stabilizers, ozone protectants, fatty acids, plasticizers, nucleators, expandants, accelerators and/or fillers (for example, carbon black, TiO2, solid or hollow beads of glass or other materials).
Suitable crosslinkers for chemical crosslinking that are compatible with the pressure sensitive adhesive include, preferably, metal chelates, polyfunctional isocyanates, polyfunctional amines or polyfunctional alcohols. Furthermore, among others it is also possible to use polyfunctional acrylates with advantage as crosslinkers for a crosslinking induced or promoted by actinic radiation.
In the case of UV crosslinking of the pressure sensitive adhesive, UV photoinitiators are added to the block copolymers as substances which promote and/or initiate crosslinking. Useful photoinitiators whose use is very favorable include benzoin ethers, such as benzoin methyl ether and benzoin isopropyl ether, for example, substituted acetophenones, such as 2,2-diethoxy-2-phenyl-1-phenylethanone, 2,2-dimethoxy-2-phenyl-1-phenylethanone, dimethoxyhydroxyacetophenone, for example, substituted alpha-ketols, such as 2-methoxy-2-hydroxy-propiophenone, for example, aromatic sulfonyl chlorides, such as 2-naphthylsulfonyl chloride, for example, and photoactive oximes, such as 1-phenyl-1,2-propanedione 2-(O-ethoxycarbonyl)oxime, for example.
A further development which makes the inventive process particularly advantageous for the preparation of, for example, adhesive tapes is notable for the further processing of the (blended or unblended) pressure sensitive adhesive from the melt, in which case it is applied in particular to a backing.
Suitable backing materials in this context include those materials which are customary and familiar to the skilled worker, such as, for example, films (polyester, PET, PE, PP, BOPP, PVC), webs, foams, wovens and scrimmed films, and also release paper (glassine, HDPE, LDPE).
Subsequent to preparation and further processing, advantageously, the pressure sensitive adhesive is crosslinked. Crosslinking takes place preferably by means of brief UV exposure within a wavelength range of about 200 to 400 nm using commercially customary high or medium pressure mercury lamps with an output of, for example, from 80 to 240 W/cm, by means of thermal energy within a temperature range between about 70 and 140° C., or by means of ionizing radiation, such as electron beam curing, for example.
For UV crosslinking it may be appropriate to adapt the lamp output to the belt speed or, in the case of slow travel, to partially shade off the belt in order to reduce its heat exposure. The exposure time depends on the model and output of the radiation sources in question. Accordingly, the invention finally provides for the use of a pressure sensitive adhesive as described above for an adhesive tape provided on one or both sides with the pressure sensitive adhesive, particularly for an adhesive tape for bonds to apolar surfaces, said adhesive tape being prepared preferably by applying the pressure sensitive adhesive from the melt to a backing.
The purpose of the examples below is to illustrate the invention, without wishing to subject it to any unnecessary restriction.
Commercially available chemicals employed
Chemical composition
Vazo 67
Regalite R91
fully hydrogenated hydrocarbon resin,
Mn = 500 g/mol, polydispersity = 1.4
Softening range: 85-91° C.
A strip of adhesive tape 13 mm wide was applied to a smooth, cleaned steel surface. The area of application measured 20 mm×13 mm (length×width). Subsequently, the following procedure was carried out:
Test TA1: At room temperature, a 1 kg weight was fastened to the adhesive tape, and the time until the weight fell off was recorded.
Test TA2: At 70° C. a 1 kg weight was fastened to the adhesive tape, and the time until the weight fell off was recorded.
The shear adhesion times recorded are each recorded in minutes and correspond to the average of three measurements.
A strip 20 mm wide of an acrylic pressure sensitive adhesive applied to a polyester layer was applied in turn to PE (TB1) or PP (TB2) plates. The pressure sensitive adhesive strip was pressed down twice onto the substrate using a 2 kg weight. The adhesive tape was then immediately removed from the substrate at an angle of 180° and a speed of 300 mm/min. All of the measurements were conducted at room temperature under controlled-climate conditions.
The results are reported in N/cm and are averaged from three measurements.
As a regulator, the following trithiocarbonate (V) was prepared in accordance with Macromolecules 2000, 33, 243-245 and Synth. Commun. 1988, 18, 1531-1536.
A 500 ml Schlenk vessel was charged with 400 ml of styrene and 3.47 g of the trithiocarbonate (V) (0.01172 mol) and degassed three times, after which the polymerization was carried out under argon. It was initiated by heating to 120° C. and carried out with stirring for 30 hours. To isolate the product, the batch was cooled to RT and the polymer was dissolved in 1000 ml of dichloromethane and then precipitated from 7.5 l of methanol with vigorous stirring. The precipitate was filtered off on a frit and then analyzed by GPC (Mn=23 500, Mw/Mn=1.32).
A 750 ml Schlenk vessel was charged with 500 ml of styrene and 3.47 g of the trithiocarbonate (V) (0.01172 mol) and degassed three times, after which the polymerization was carried out under argon. It was initiated by heating to 120° C. and carried out with stirring for 48 hours. To isolate the product, the batch was cooled to RT and the polymer was dissolved in 1000 ml of dichloromethane and then precipitated from 7.5 l of methanol with vigorous stirring. The precipitate was filtered off on a frit and then analyzed by GPC (Mn=29 100, Mw/Mn=1.26).
A reactor conventional for radical polymerizations was charged with 32 g of trithiocarbonate-functionalized polystyrene (VI), 400 g of 2-ethylhexyl acrylate, 45 g of Kraton Liquid L-1253 ™ (Shell), 4 g of acrylic acid and 0.12 g of Vazo 67™ (DuPont). After argon had been passed through for 20 minutes and the reactor degassed twice, it was heated to 70° C. with stirring. After 4 hours, dilution was carried out using 200 g of acetone/special boiling point spirit (1:2), reinitiation took place after 5 hours with 0.12 g of Vazo 67™, and after 24 hours the polymerization was terminated.
For isolation, the batch was cooled to RT, the block copolymer was diluted to 40% with acetone/special boiling point spirit (1:2) and then blended with 10 parts by weight of Regalite R91 ™ (Hercules) based on the polymer fraction. The acrylic block copolymer is freed from the solvent mixture in a vacuum/drying cabinet and then coated from the melt onto a Saran-primed PET backing, 23 μm thick, at an application rate of 50 g/m2 from a slot die. The product was then tested in accordance with methods TA1, TA2 and TB1, TB2.
The procedure of Example 1 was repeated. The acrylic block copolymer was blended with 20 parts by weight of Regalite R91™ (Hercules) based on the polymer fraction. After coating from the melt, testing was carried out in accordance with methods TA1, TA2 and TB1, TB2.
The procedure of Example 1 was repeated. The acrylic block copolymer was blended with 30 parts by weight of Regalite R91 ™ (Hercules) based on the polymer fraction. After coating from the melt, testing was carried out in accordance with methods TA1, TA2 and TB1, TB2.
A reactor conventional for radical polymerizations was charged with 32 g of trithiocarbonate-functionalized polystyrene (VII), 340 g of n-butyl acrylate, 4 g of acrylic acid, 44 g of Kraton Liquid L-1253™ (Shell) and 0.12 g of azoisobutyronitrile (AIBN). After argon had been passed through for 20 minutes and the reactor degassed twice, it was heated to 60° C. with stirring, reinitiation took place after 2 hours with 0.12 g of Vazo 67™ (DuPont), after 6 hours, dilution was carried out using 150 g of acetone/special boiling point spirit (1:2), and after 24 hours the polymerization was terminated.
For isolation, the batch was cooled to RT, the acrylic block copolymer was diluted to 40% with acetone/special boiling point spirit (1:2) and then blended with 10 parts by weight of Regalite R91 ™ (Hercules) based on the polymer fraction. The acrylic block copolymer is freed from the solvent mixture in a vacuum/drying cabinet and then coated from the melt onto a Saran-primed PET backing, 23 μm thick, at an application rate of 50 g/m2 from a slot die. The product was then tested in accordance with methods TA1, TA2 and TB1, TB2.
The procedure of Example 4 was repeated. The acrylic block copolymer was blended with 30 parts by weight of Regalite R91 ™ (Hercules) based on the polymer fraction. After coating from the melt, testing was carried out in accordance with methods TA1, TA2 and TB1, TB2.
A conventional radical polymerization reactor was charged with 1.6 g of trithiocarbonate (V), 400 g of 2-ethylhexyl acrylate, 40 g of Kraton Liquid L-1253™ (Shell), 100 g of acetone and 200 g of special boiling point spirit 60/95, and degassed three times, after which the polymerization was carried out under argon. It was initiated by heating to 80° C., and by addition of 0.2 g of Vazo 67™ (DuPont). After 4 hours, a further 0.2 g of Vazo 67™ (DuPont) was added and after 6 hours the batch was diluted with 100 g of special boiling point spirit 60/95. After 48 hours the polymerization was terminated, the batch was cooled to RT, and the polymer was freed from the solvent in a vacuum drying cabinet. The polymer was then dissolved in 200 g of xylene and 80 g of styrene, again transferred to a polymerization reactor and heated to 120° C., and 0.2 g of Vazo 67™ (DuPont) was added. After 6 hours, a further 0.2 g of Vazo 67™ (DuPont) was added. After 48 hours, the polymerization was terminated by cooling to RT. The block copolymer was subsequently blended with 10 parts by weight of Regalite R91 ™ (Hercules) based on the polymer fraction, freed from the solvent in a vacuum/drying cabinet, and then coated from the melt onto a Saran-primed PET backing, 23 μm thick, at an application rate of 50 g/m2 using a slot die. The product was then tested in accordance with methods TA1, TA2 and TB1, TB2.
The table below lists the technical properties of these adhesives.
BS to PE/TB1
BS to PP/TB2
+10 000
+10 000
+10 000
+10 000
+10 000
SAT: Shear adhesion times in minutes
BS: bond strength in N/cm
Examples 1 to 3 demonstrate that the polystyrene end block-functionalized polyacrylates of the invention containing apolar side chains, in combination with the resin Regalite R91™ (Hercules), exhibit a very good bond strength to apolar surfaces. The higher the resin fraction, the higher the bond strength to PE and PP. At 30% resin, bond strengths of more than 7 N/cm are realized.
Additionally, owing to the formation of block domains in the polystyrene, crosslinking is no longer needed. The specimens have high shear strength at room temperature and therefore very good cohesion. Furthermore, the pressure sensitive adhesives are very clear and transparent, despite the fact that Regalite R91™ is a highly apolar resin and is normally not compatible with polyacrylates. Example 6 represents an inversely constructed block copolymer with the structure P(A)-P(B)-P(A). These block copolymers are also obtainable by means of the process, and can be used without additional crosslinking as strong pressure sensitive adhesives.
Cited Patent | Filing date | Publication date | Applicant | Title |
US5225470 * | Feb 22, 1991 | Jul 6, 1993 | Monssanto Company | Acrylic hot melt pressure sensitive adhesive compositions |
US5229195 * | Jun 16, 1992 | Jul 20, 1993 | Lintec Corporation | Composite body having a blister-free pressure-sensitive adhesive sheet attached thereto |
US5294668 * | Nov 15, 1990 | Mar 15, 1994 | Minnesota Mining And Manufacturing Company | Polyolefin pressure-sensitive adhesive compositions containing macromonomers |
US5578683 * | Jun 27, 1994 | Nov 26, 1996 | Avery Dennison Corporation | Crosslinkable graft pressure-sensitive adhesives |
US5625005 * | Oct 25, 1995 | Apr 29, 1997 | Avery Dennison Corporation | Acrylic saturated rubber hybrid pressure-sensitive adhesives |
US5648166 * | Feb 21, 1995 | Jul 15, 1997 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesives and tape articles |
US5650215 * | May 5, 1995 | Jul 22, 1997 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesives having microstructured surfaces |
US6589651 * | Sep 13, 2001 | Jul 8, 2003 | Rohm And Haas Company | Adhesive compositions containing graft copolymers |
US20010044024 * | Apr 4, 2001 | Nov 22, 2001 | Hiraku Miyashita | Acrylic hot melt pressure-sensitive adhesive and protective film utilizing the same |
US20030013790 * | Feb 15, 2002 | Jan 16, 2003 | Marc Husemann | Pressure sensitive adhesive, particularly for apolar surfaces |
US20030096111 * | May 21, 2002 | May 22, 2003 | Marc Husemann | Pressure sensitive adhesive, particularly for apolar surfaces |
EP0651013A1 | Sep 26, 1994 | May 3, 1995 | Rohm And Haas Company | A tie-layer and a process for improving adhesion of a surface layer to a polyolefin substrate |
EP0822967A1 | Apr 17, 1996 | Feb 11, 1998 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesives for polyolefin surfaces |
EP0921170A1 * | Dec 2, 1998 | Jun 9, 1999 | Elf Atochem S.A. | Utilisation of linear non-dienic type block copolymers as auto-adhesives or auto-adhesive components |
WO1995002003A1 | Jul 8, 1994 | Jan 19, 1995 | Avery Dennison Corporation | Acrylic-saturated rubber hybrid pressure-sensitive adhesives |
Citing Patent | Filing date | Publication date | Applicant | Title |
US7605212 | Sep 9, 2005 | Oct 20, 2009 | Tesa Se | Method for producing contact adhesive masses containing acrylic |
US7618705 * | Aug 17, 2004 | Nov 17, 2009 | Lintec Corporation | Pressure-sensitive adhesive sheet for tire and method for manufacturing the same |
US20050050429 * | Aug 4, 2003 | Mar 3, 2005 | Tantivy Communications, Inc. | Forward error correction scheme for high rate data exchange in a wireless system |
US20060009552 * | Apr 28, 2005 | Jan 12, 2006 | Tesa Aktiengesellschaft | Pressure-sensitive adhesive |
US20060154098 * | Nov 11, 2003 | Jul 13, 2006 | Tesa Ag | Self-adhesive article |
US20070054118 * | Aug 17, 2004 | Mar 8, 2007 | Kouji Tabata | Pressure sensitive adhesive sheet for a tire and producing method for the same |
US20070282064 * | Sep 9, 2005 | Dec 6, 2007 | Tesa Ag | Method for Producing Contact Adhesive Masses Containing Acrylic |
U.S. Classification | 428/355.0AC, 526/328.5, 526/329, 428/355.00R, 526/329.7 |
International Classification | C08F293/00, C09J157/00, C09J133/06, C09J153/00, C09J7/02 |
Cooperative Classification | Y10T428/2852, C09J153/00, C08F293/005, Y10T428/2891 |
European Classification | C09J153/00, C08F293/00B |
Date | Code | Event | Description |
May 6, 2002 | AS | Assignment | Owner name: TESA AG, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HUSEMANN, MARC;ZOLLNER, STEPHAN;REEL/FRAME:012879/0495 Effective date: 20020423 |
Jun 8, 2007 | FPAY | Fee payment | Year of fee payment: 4 |
Oct 7, 2010 | AS | Assignment | Owner name: TESA SE, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:TESA AG;REEL/FRAME:025105/0057 Effective date: 20090331 |
Jun 9, 2011 | FPAY | Fee payment | Year of fee payment: 8 |
Jun 11, 2015 | FPAY | Fee payment | Year of fee payment: 12 |
Dec 17, 2015 | AS | Assignment | Owner name: TESA SE, GERMANY Free format text: CHANGE OF ADDRESS;ASSIGNOR:TESA SE;REEL/FRAME:037317/0675 Effective date: 20150422 |


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United States District Court, D. Minnesota
July 2, 2015
Demarco Hughes, Plaintiff,v.Georgina M. Goynes, Defendant.
DONOVAN W. FRANK, District Judge.
The above matter comes before the Court upon the Report and Recommendation of United States Magistrate Judge Jeffrey J. Keyes dated April 29, 2015. (Doc. No. 46.) The factual background for the above-entitled matter is clearly and precisely set forth in the Report and Recommendation and is incorporated by reference.
No objections have been filed to that Report and Recommendation in the time period permitted, which required objections by May 13, 2015. However, on May 29, 2015, Plaintiff filed a "Reply to Report and Recommendation, " which appears to provide evidence supporting Plaintiff's claims for damages (Doc. No. 47.), as requested in the Report and Recommendation (Doc. No. 46 at 10.)
The Court acknowledges receipt of Plaintiff's Reply and having fully considered Magistrate Judge Keyes's Report and Recommendation, as well as the Reply, adopts the Report and Recommendation in full. The Report and Recommendation recommended that Plaintiff be given 30 days from the date of this Order to provide evidence supporting his claims that he owned the items of personal property listed in the attachment to his Consolidated Amended Complaint (Doc. No. 40-1), and evidence supporting those items' monetary value. Plaintiff may now also submit additional items that show ownership and value within 30 days from the date of this order. The Court notes that Plaintiff's current Reply (Doc. No. 47) is likely insufficient to establish his ownership and the monetary value of the items he has listed as lost. The Court suggests that Plaintiff should submit additional evidence that may include, but is not limited to, receipts for work performed on the vehicles, vehicle titles, vehicle registration statements, etc. Further, the Court again cautions Plaintiff that self-serving affidavits authored by Plaintiff and his family may also be insufficient in this regard.
Thus, based upon the Report and Recommendation of the Magistrate Judge and upon all of the files, records, and proceedings herein, the Court now makes and enters the following:
1. Magistrate Judge Jeffrey J. Keyes's April 29, 2015 Report and Recommendation (Doc. No. [46]) is ADOPTED.
2. Plaintiff Demarco Hughes is entitled to a default judgment against Defendant Georgina M. Goynes on Plaintiff's claims that Defendant wrongfully deprived him of his personal property.
3. Plaintiff's motion for summary judgment (Doc. No. [45]) is DENIED AS MOOT.
4. Plaintiff must submit evidence supporting his claims that he owned the items of personal property listed in the attachment to his Consolidated Amended Complaint (Doc. No. 40-1), and evidence supporting those items' monetary value, within 30 days of this Order Adopting the Report and Recommendation, so that the Court can evaluate ...
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The last Boeing C-17 Globemaster III cargo plane built at the company's Long Beach plant departed from the facility Sunday, closing an important era for aircraft manufacturing in California.
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I see you!
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I don't know who was more surprised, this little bird or me. While at Mason Neck Park last weekend there were many nesting boxes in the area. This one was near a bench we had been sitting on at the end of our walk. Gregg and I were getting ready to leave and he was half way to our car when my curiosity once again took over and I hung back. I wanted to see if there was any nesting material inside because after sitting a few minutes I saw no activity. Not wanting to walk right up to the box I pointed my camera at it and zoomed in. Yes, I could see some small twigs, yes there were signs of a nest. Curiosity satisfied I was about to leave when suddenly this little head popped up. I was so surprised it gave me a bit of a jolt. In the viewfinder his head seemed as big as a bowling ball and he startled me so I almost fell out of my shoes. That's what focusing like a laser does and not expecting to see anything I suppose. I was able to snap off a picture or two before I joined Gregg and shared with him the cute little bird I had just encountered. I think maybe he is a tree swallow as I saw several flying about earlier.


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Publisher: mcgraw-hill nyc 1971
Publication Date: 1971
Binding: Hardcover
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Edition: 1st Edition
brodart protected neil fijuta dj with $6.75 on flap and some of the cellophane loosening---common with this book only this time not much loosening purple cloth with black cloth spine stamped in gold 349 states fiorst american Book Condition - Fine, Jacket Condition - fine. First Edition. Hardcover. Bookseller Inventory # 120227
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Out of concern for the health and well-being of our patients, Novant Health is asking the community to keep visitors age 12 and under out of all of its hospital facilities effective Friday, Feb. 24 at 7 a.m. Read more about visitor restrictions due to the widespread outbreak of the flu virus.
The Novant Health Charlotte market offers a wide variety of classes, seminars, support groups, maternity tours and community events at our hospitals and other facilities. Please note: Some of our classes fill up very quickly. If you plan to take a maternity tour or register for infant CPR or newborn care classes, we highly encourage you to secure your spot as soon as possible.
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Publication of Earnings 2015-16
Patient notice, merger with The Surgery, Fulmar Drive
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Heaton Moor Medical Group is a combination of practices with a branch surgery's & a combined patient list of over 31,500 patients. Our GPs and large support teams offer a broad range of services to our patients.
The surgery opened in 1971, taking in just six doctors originally. Since then, the premises were totally renovated and extended in 1994 and extended again in 2002. Over this time our team has grown to include twelve doctors and seven practice nurses.
We are training practices and have GP Registrars, nursing students and medical students. They are an important part of our services and help us to keep up to date with the latest developments in healthcare.
We are also keen to innovative and are always looking for ways to improve our services for patients. We participate in pilot schemes for new ways of providing care, as well as adapting to feedback and suggestions from patients.
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Deep Dark Blue Forest
by Sondergaard
Updated | |
Artist | Sondergaard |
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nature pretty dark fantasy deep surreal beautiful branches trees wood magic goth gothic horror magical scary woods blue black green sky insekts flyes night twilight pretty sad alone spooky
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Beautiful shade of blue. I love that there are contrasty darks and lights but the lights aren't so pale they get bright. Text is easy to read.
Rated 5 out of 5 stars by PamperedSaluki on March 29, 2015
My favorite theme
This is my favorite theme :)
Rated 5 out of 5 stars by DarkKnightRenee on January 17, 2014
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text:
Sci fi/Fantasy image by
Sascha Stiven-TomsettXanthia, my level seven (out of eight) L.A.R.P. character. She is an invoker of Ashan, an elf and aparently a vampire. Shhh, don't tel the church she works for... :D. The symbol on the desk is a spirit talisman of aura of fear. Tells you alot about Xanthia. She is crazy. Oh yeah and married to a druid who is afraid of sunlight and water. Joyous marriage. just a sketch for the moment will finish the colour version one day.
Published More than a year ago
Category Mythology
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