1  US 6,291,723  Bl  2  DIOLEFIN/HYDROXYARYL CONDENSATES  AND CATALYST THEREFOR  FIELD OF INVENTION  BACKGROUND OF THE INVENTION  SUMMARY OF THE INVENTION  In a further aspect, this invention relates to condensing a  hydroxyaryl with a non-conjugated diene in the presence of  In yet another aspect, this invention relates to a method  for condensing a hydroxyaryl with a non-conjugated diene  in the presence of a catalyst system comprising trifluo› romethanesulfonic acid and a substance in a quantity which  decreases without eliminating the catalytic activity of the  acid and which does not react with a double bond of the  diene to prepare condensates having one mole of diene  bound with one mole of a hydroxyaryl, condensates having  two moles of the hydroxyaryl bound with one mole of the  diene, as well as higher molecular weight products, includ› ing resins.  U.S. Pat. No. 5,663, 470 of Sep. 2, 1997 to  F. Chen et al  discloses a heterogeneous catalyst system comprising a solid  state insoluble salt catalyst for polymerization and alkylation  of olefinic monomers in the presence of a polar or non-polar  reaction medium which comprises: (a) a solid state catalyst  component of at least one salt of a strong acid and certain  transition metals wherein the salt is insoluble in the reaction  medium; and (b) a cocatalyst for promoting the polymer- ization. The salt of a strong acid includes that of triflic acid.  Monomers include a wide variety of olefins and carbocyclic  In still a further aspect, this invention relates to a com› position comprising a hydroxyaryl, a non-conjugated diene,  trifloromethanesulfonic acid and a substance in a quantity  which decreases without eliminating the catalytic activity of  the acid and which does not react with a double bond of the  diene.  In another aspect, this invention relates to a catalyst  composition comprising triflic acid and a substance in a  quantity which decreases without eliminating the catalytic  activity of the acid and which does not react with a double  bond of a non-conjugated diene.  U.S. Pat. No. 5,607,890 of Mar. 4, 1997 to  F. J. Chen et  al discloses heterogeneous catalysts having certain insoluble  triflic acid salts on an inorganic oxide support for catalyzing  hydrocarbon conversion reactions including alkylation and  polymerization.  As  suitable monomers for the conversion  reactions a wide variety of olefins and carbocyclic aromatic  compounds are mentioned. Monomer feed streams for poly› merization are substantially free of impurities which may  adversely affect polymerization such as basic and nitrogen  materials. Lower alcohols along with organic acids are  mentioned as catalyst promoters.  U.S. Pat. No. 5,521,260 of May 28, 1996 to N. Futaesaku  et al discloses the use of triflic acid as a polymerization  catalyst for thermosetting resins.  U.S. Pat. No. 4,973,764 of Nov. 27,1990 to  A Oswald et  al discloses the use of triflic acid as an alkoxylation catalyst. 40  In one aspect, this invention relates to a method for  condensing a hydroxyaryl with a non-conjugated diene in  the presence of a catalyst composition comprising trifluo› romethanesulfonic acid (triflic acid) and a substance in a  quantity which decreases without eliminating the catalytic  activity of the acid .  The prior art shows the use of trifluoromethanesulfonic  acid (triflic) acid as a catalyst for various hydrocarbon  conversion processes but such prior art fails to suggest the  instant invention. Some prior art patents involving the use of  triflic acid as a catalyst or the preparation of condensation  products from a diene and a hydroxyaryl are set forth below.  H. A Bruson, et al., J. Amer. Chem. Soc. 68, 8 (1946), pp  8-10, shows the preparation of aryloxy-dicyclopentadiene  compounds from hydroxyaryls and dicyclopentadiene in the  presence of various acids.  Neftekhimiya, 1974, Volume  XIV,  No. 2, 280-283  (Russian) discloses the reaction of phenol with clicyclopen› tadiene in the presence of about 10% to 50% by weight,  based on the weight of both monomers, of a cation exchange  resin catalyst for the preparation of compounds, such as  prepared in the instant invention, including some resin.  It has now been found that the reaction of a hydroxyaryl  with a non-conjugated diene in the presence of both triflic  acid and a retarder will produce products which are sub› stantially different from such reaction without the use of the  retarder. Broadly, the use of the retarder provides products  which have lower molecular weights such as solids, crys› talizable and non-crystalizable liquids having a wide range  of viscosities. The retarder is a material which at certain  concentrations in relation to the triflic acid decreases, with› out eliminating, the catalytic activity of the triflic acid. The  retarders are generally about neutral to slightly basic in pH.  The retarder acts as a base in relation to the triflic acid.  3M Product Information Bulletin of 6-95 entitled "Fluo- rochem" discloses various properties and uses of triflic acid,  e.g., the use of triflic acid as a catalyst in alkylation and  polymerization reactions as well as some physical or chemi› cal properties of mixtures of triflic acid with water or ethers.  aromatic compounds. The enumeration of cocatalyst  includes water, alcohols such as the lower alkanols, e.g.,  methanol, and Bronsted acids such as triflic acid or Lewis  acids. This 470 patent of Chen et al describes triflic acid,  water and methanol as catalyst reaction promoters.  However, in, the catalyst system of the instant invention,  water and alcohols, e.g., methanol are catalyst suppressors in  that water and methanol both act as catalyst retarders instead  of promoters. Although the applicant does not wish to be  held to any theory, it is believed that water as well as  methanol in contact with the insoluble catalyst salts of Chen  et al cause dissociation of the salts which in turn promote the  catalytic reaction.  This invention relates to condensation products of a  hydroxyaryl and a diolefin, the method for preparation of  such products as well as a catalyst system used for their  preparation. More particularly, this invention relates to such  condensation products and their method of manufacture in  the presence of a catalyst composition containing trifluo› romethanesulfonic acid ( triflic acid) and a substance in an  amount which decreases without eliminating the catalytic  activity of the acid, said substance is also simply referred to  as a retarder. 