I 1111111111111111 11111 1111111111 111111111111111 IIIII IIIII 111111111111111111  US009045650B2  c12)  United States Patent  Finnie et al.  (IO)  Patent No.:  US 9,045,650 B2  (45)  Date of Patent:  Jun. 2, 2015  (54)  POLYMER WITH SALT GROUPS AND  ANTIFOULING COATING COMPOSITION  COMPRISING SAID POLYMER  (58)  Field of Classification Search  CPC ...... C09D 5/16; C09D 5/1687; C09D 5/1656;  C08F 220/18  USPC ......................... 523/122; 514/772.3; 528/321  See application file for complete search history.  (75)  Inventors:  Alistair Andrew Finnie,  Whitley Bay  (GB);  Clayton Price,  Whitley Bay (GB);  Richard Mark Ramsden,  Pelaw (GB)  (73)  Assignee:  AKZO NOBEL COATINGS  INTERNATIONAL B.V.,  Arnhem (NL)  ( *)  Notice:  Subject to any disclaimer, the term of this  patent is extended or adjusted under 35  U.S.C. 154(b) by 254 days.  (21)  Appl. No.:  13/058,714  (22)  PCT Filed:  Aug.10,2009  (86)  PCT No.:  PCT/EP2009/060317  § 371 (c)(l),  (2), ( 4) Date:  Feb. 11, 2011  (87)  PCT Pub. No.:  WO2010/018144  PCT Pub. Date:  Feb. 18, 2010  (65)  Prior Publication Data  US 2011/0144217 Al  Jun. 16, 2011  Related U.S. Application Data  (60)  Provisional application No. 61/091,813, filed on Aug.  26, 2008.  (30)  Foreign Application Priority Data  Aug. 13, 2008  (EP) ..................................... 08162288  (51)  Int. Cl.  C09D 5116  C08G  75124  A0lP 15100  C08F 220118  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (52)  U.S. Cl.  CPC ................  C09D 5116  (2013.01);  C09D 511656  (2013.01);  C09D 511687  (2013.01);  C08F  220118  (2013.01)  (56)  References Cited  U.S. PATENT DOCUMENTS  2008/0124298 Al*  5/2008 Solomon et al ............ 424/78.09  FOREIGN PATENT DOCUMENTS  EP  EP  GB  GB  WO  WO  WO  WO  0 529 693  0 663 409  798 604  1 457 590  00/43460  02/02698  2004/018533  2005/075581  3/1993  7 /1995  7 /1958  12/1976  7/2000  1/2002  3/2004  8/2005  OTHER PUBLICATIONS  International Search Report, PCT/EP2009/060317, mailed Oct. 2,  2009, 4 pages.  European Search Report, EP 08162288.8, mailed Dec. 18, 2008, 6  pages.  Szegezdi, Jozsef, et al., "New method for  pKa  estimation", presented  at eCheminformatics, Nov. 10-14, 2003.  Szegezdi, Jozsef, et al., "Prediction of dissociation constant using  microconstants", presented at the American Chemical Society  National Meeting, Mar. 28-Apr.2004.  * cited by examiner  Primary Examiner  - Kriellion Sanders  (74)  Attorney, Agent, or Firm  - Kenyon & Kenyon LLP  (57)  ABSTRACT  Szegezdi, Jozsef, et  al., "A method for calculating the  pKa  values of  small and large molecules", presented at the American Chemical  Society Spring Meeting, Mar. 25-29, 2007.  A film-forming polymer with improved chemical stability in  antifouling coating applications, said polymer bearing pen› dant to its backbone a salt of (i) a basic group with a first  pKa  of the conjugate acid of at least 4.0 and (ii) an organic acid  with a first  pKa  of 2.0 or less; said basic group being  covalently bonded to the polymer backbone.  21 Claims, No Drawings 