US006291723Bl  (12)  United States Patent  Gerber  (10)  Patent No.:  US 6,291,723 Bl  (45)  Date of Patent:  Sep.18,2001  (54)  DIOLEFIN/HYDROXYARYL CONDENSATES  AND CATALYST THEREFOR  (75)  Inventor:  Arthur H. Gerber,  Louisville, KY  (US)  (73)  Assignee:  Borden Chemical, Inc.,  Columbus, OH  (US)  ( *)  Notice:  Subject to any disclaimer, the term of this  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  (21)  Appl. No.:  09/388,966  (22)  Filed:  Sep. 2, 1999  (51)  Int. Cl.7  ............................  C07C 37/14;  C07C 39/06  (52)  U.S. Cl.  ..........................  568/793;  568/628; 568/630;  568/632; 568/732; 568/733; 568/806; 528/205;  528/171  (58)  Field of Search  ..................................... 568/733, 793,  568/806, 732, 628, 630, 632; 528/205,  171  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  4,394,497  4,914,246  4,927,905  4,973,764  5,281,675  5,338,828  5,491,201  5,521,260  5,607,890  5,663,470  5,739,377  7/1983 Nelson et al. ....................... 528/101  4/1990 Oswald et al. ....................... 568/793  5/1990 Bogan .................................. 528/205  11/1990 Oswald et al. ....................... 568/649  1/1994 Hefner, Jr. et al. .................. 525/410  8/1994 Hefner, Jr. et al. .................. 528/179  2/1996 Hefner, Jr. et al. .................. 525/420  5/1996 Futaesaku et al. ................... 525/502  3/1997 Chen et al. .......................... 502/202  9/1997 Chen et al. .......................... 585/520  4/1998 Ohsawa et al. ........................ 560/75  05156134  *  6/1993 (JP) .  3M Fluorad, FC24, Product Information Bulletin, Jun. 1995.  "Reaction of Phenol with Endo-Dicyclopentadiene" V.  Isagulyants et al. Neftekhimia (1974) 14(2), 280---3 -With  English Translation.  Beilstein,  RN  52062-67-6 Registry, Phenol, 4-(3a4,5,6,7,  7 a-hexahydro-4, 7-methano-lH-inden-6-y l)-(9CI)  (1998).  "Reaction of Phenol with Alkyl- and Alkenylcycloalkenes  in the Presence of KU 23 Catalyst" Sadykhov, Sh. et al.  Neftekhimiya (1996), 36(2), 158-168.  "Reaction of Phenol with Alkylcycloalkenes on a Zeolite› -Containing Aluminosilicate Catalyst" Soldatove, V. et al.  Neftekhimiya (1988), 28(2), 189-99.  "Catalytic Alkylation of Phenol by Isoprene Dimers"  Sadykhov. Sh. et al. Azerb. Neft. Khoz, (1984), (3), 46-9.  "Study of the O-Cycloalkylation of Phenol with Alkylcy› cloalkenes" Sadykhov, Sh. et al. Azerb, Khim Zh. (1978),  (2), 35-7.  "Use of Ion Exchange Resins in Catalysis, Reaction of  Dicyclopentadiene  with  phenol  on  a  KU  2  Cation  Exchanger" Isagulyants, V. et al., Zh. Prikl. Khim. (Lennin› grad) (1974) 47 (3), 684.  H.  A Bruson, et al.;  J.  Am. Chem. Soc. 68, 8 (1946) pp.  8-10.  *  cited by examiner  Primary Examiner-Sreeni  Padmanabhan  (74)  Attorney, Agent, or Firm-George  P. Maskas; Kenneth  P. Van Wyck  A catalyst composition comprising trifluoromethanesulfonic  acid ( also referred to as triflic acid) and a sufficient quantity  of a substance ( also referred to as a retarder) to decrease but  not eliminate the catalytic activity of the acid is disclosed.  Also disclosed, is a method and composition for condensing  a hydroxyaryl with a diene by use of the catalyst composi› tion. The method is capable of producing condensates hav› ing: a mole ratio of 1 mole of the diene to one mole of the  hydroxyaryl; one mole of diene to two moles of the  hydroxyaryl as well as higher molecular weight products  such as resins by changes in temperature, time of reaction,  type and quantity of retarder and other variables.  (57)  ABSTRACT  33 Claims, No Drawings 