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(’ffhe calculated % of OH: for the bis(hydroxyaryl)-non-conjugated diene is 10.6; for the aryloxy-non-conjugated-diene compound is 0.0 and hydroxyaryl-non-conjugated-diene compounds is 7.5; and for the polycon- densate is 7.5. The polycondensate is a chain of self polymerized units and polymerized mixture of units. (b)Contains traces of methanol and hydroxyphenyl-dicyclopentadiene com› 

pound. 

A determination of the hydroxyl number (and equivalent) is made as follows: A solution of 2.0 g sample is refluxed for 2 hours with 25 ml of pyridine/acetic anhydride solution (from 250 ml pyridine plus 60 ml of the anhydride). The reflux condenser is rinsed with 5 ml water and the contents heated for an additional 5 minutes. Heat is removed and the condenser rinsed with 25 ml methanol. After cooling to room temperature, the contents are titrated with 1.0 N sodium hydroxide to pH of 9 by using the pH meter. The titre is expressed as "A". For the blank ("B"), a mixture of the same volume of acetic anhydride, pyridine and water as used above is mixed and allowed to stand for 15 minutes shortly before titration, the same amount of methanol as was used above as a rinse is added. "B" is expressed in mls (milliliters). The calculation for "%OH" is: 

The calculation for hydroxyl equivalent is: 

Example 1 of U.S. Pat. No. 4,927,905 was essentially followed but at a mole ratio of 0.077 of dicyclopentadiene to phenol. Thus, dicyclopentadiene (132 g., 1.0 mole) was added over one hour under nitrogen blanket to a solution of phenol (1,223.3 g ,13 moles) and boron trifluoride etherate ( 6.8 g, 0.5% on phenol) at 70° C. The reaction was then heated over 4 hours to 150° C. and maintained at this temperature for 1.5 hours. Reaction was then cooled to 60° C. and catalyst neutralized with 6.5 g of 45% KOH. Phenol was recovered by vacuum distillation to 190° C. at 26 inches 

(B-A)(IN)(0.017)(100) divided by Sample Weight, in grams. 

17x100 divided by %OH. 

## COMPARATIVE EXAMPLE 50 

Preparation of Dicycloperitadiene/Phenol Resin Using Boron Trifluoride Catalyst and at a Mole Ratio of 0.077 of Dicyclopentadiene to Phenol 

of vacuum and then the residue steam sparged with 100 ml water at 185-190° C. under 26 inches of vacuum. Product (312 g) was characterized as follows: viscosity of 1210 cps at 125° C. Mw/Mn 322/262; phenol of <0.05%; boron of 0.027%; fluorine of 1.06%; phenol-dicyclopentadiene com› pound of trace ( <1 %). Also no phenoxy-dicyclopentadiene compound (ether) was detected. 

Dicyclopentadiene (198.5 g, 1.5 moles) was added over one hour under nitrogen blanket to a solution of phenol (565 g, 6.0 moles) and boron trifluoride etherate (2.25 g, 0.4% on phenol) at 70° C. Reaction mixture was further heated and phenol and product recovered as in Example 50. Product (317 g) was characterized as follows: viscosity of 20,900 cps at 125° C.; 942 cps at 150° C.; Mw/Mn of 580/318; and phenol-dicyclopentadiene compound of about 3%. 

The procedure of Example 38A was followed except that an equimolar amount of methanesulfonic acid(l.3:3g of 10% acid in phenol) replaced 2.08 g of 10% triflic acid in phenol. Essentially, no reaction occurred after one hour at 45° C. after diene addition at 45° C. (refractive index of 1.5314 at 27.7° C.). Very little reaction occurred after another 4 hours at 70° C. when the refractive index was 1.5344 (27.6° C.). This is versus a refractive index of 1.5548 (26.1 ° C.) for Example 38A at this time and 1.5569 after 7 hours at 70° C. The reaction was then heated to 90° C. wherein the refractive index changed as shown in Table 52 below wherein R. I. is refractive index at 25–0.5° C. 

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After 11 hours at 90° C., as shown in Table 52 above, the reaction mixture was neutralized and then analyzed. The analysis showed: 14.9% of unreacted dicyclopentadiene which translates to but a 61 % conversion of the diene; and a ratio of about 3.4 of phenoxy-dicyclopentadiene com- pound to hydroxyphenyl-dicyclopentadiene compound. 

From the above Comparative Example 52 and Table 52 it can be seen that the very strong methanesulfonic acid (about 0.5 times the acidity of sulfuric acid and about twice the strength of HCI measured by conductivity in acetic acid at 25° C.) is relatively ineffective in comparison to triflic acid. 

Example 48 was followed using 9. 9 moles phenol (instead of 8.8) and 3.0 moles of the diene but after the one hour at 

## COMPARATIVE EXAMPLE 51 

Comparative Example for Preparation of Dicyclopentadiene/Phenol Resin Using Boron Trifluoride Catalyst and Mole Ratio of 0.25 of Dicyclopentadiene to Phenol 

## COMPARTIVE EXAMPLE 52 

Dicyclopentadiene/Phenol Condensate Using Methanesulfonic Acid Catalyst and Acetanilide Retarder 

Dicyclopentadiene/Phenol Condensate at Mole Ratio of 0.30 

## EXAMPLE 53 

