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# (12) United States Patent 

# Gerber 

# (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 

<img src='content_image/936956.jpg'>

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. 

## U.S. PATENT DOCUMENTS 

## FOREIGN PATENT DOCUMENTS 

## OTHER PUBLICATIONS 

<img src='content_image/936937.jpg'>

# (10) Patent No.: US 6,291,723 Bl 

# (45) Date of Patent: Sep.18,2001 

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 

## (57) ABSTRACT 

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. 

US006291723Bl 

## 33 Claims, No Drawings 

