15  US 6,291,723 Bl  16  EXAMPLE 1  EXAMPLES 1-27  TABLE A  Material  Mw/Mn (theory)  Mw/Mn via SEC Mn via VPO  Dicyclopentadiene  d-Limonene  4-Cyclopentyl› phenol  Tetrahydrodicylclo› pentadiene  132/132  136/136  162/162  89/89  122/121  88/88  143  171  136/136  Table lA below, shows reactants and reaction conditions  for Examples (Ex) 1 through 27 whereas Table lB shows  properties of the reaction products for each of the individual  examples (Ex). The method for production of the conden› sates in Examples 2-27 are the same as that for Example 1  given below, except as may be indicated on Table lA and for  a two hour addition of diene instead of one hour.  The weight average molecular weight (Mw) and number  average molecular weight (Mn) herein are measured using  size exclusion gel permeation chromatography and phenolic  compounds and polystyrene standards. The sample molecu- lar weight to be measured is prepared as follows: the sample  is dissolved in tetrahydrofuran and the solution is run  through a gel permeation chromatograph. For Examples  1-27 and lx-8x, the SEC peak at 95–1 was excluded from  the calculation of molecular weight. This would exclude  phenol and the hydroxyphenyl-non-conjugated-diene com- pound.  It  can be seen from Table A that the number average  molecular weights via vapor phase osmometry  (VPO) is  more in line with theory.  Definitions or explanations for abbreviations, headings  and subscripts shown in Table lA and lB below as well as  in examples and other tables herein are as follows unless the  context indicates otherwise:  A solid could be isolated from the original 115 g by  adding slightly to less than equal weight of n-heptane,  cooling to about -10°  C. and quickly suction filtering,  rinsing with pre-cooled n-heptane and vacuum drying.  Molecular weight of the liquid and solid products were  (Mw/Mn) 170/152 and 166/155, respectively.  The weight average molecular weight(Mw) and number  average molecular weight (Mn) values obtained by size  exclusion chromatography (SEC) reflect the average hydro› dynamic volume of the molecules and usually (except for  simple hydroxyaryl, phenol, cresol, bisphenol-A and  bisphenol-F) do not reflect an accurate molecular weight.  For example SEC molecular weight for the following pure  materials as shown in Table A below are significantly lower  than theoretical. The abbreviation "VPO" in Table A stands  for vapor phase osmometry and is more in line with theory  as compared to SEC. The VPD was performed in toluene.  A multi-neck 500 ml flask with stir bar and fitted with a  thermometer and condenser was charged under nitrogen  with: 150 g (grams) of phenol (1.59 moles); 5 g of _ti-methyl  pyrrolidone(NMP) (3.33% based on the weight of phenol);  and 0.9 g of triflic acid (0.6% based on the weight of  phenol). The stirred solution was heated to 95°  C. and over  the course of 1.5 hours 70 g (0.53 moles) of dicyclopenta› diene (Ultrene 97 of B.F. Goodrich Co.) was added at 95°  C.–1 °  C. This provided a diene/phenol mole ratio of 0.33.  The reaction mixture, over the course of about ten minutes,  was heated to 119°  C. and held at 119°  C. for one hour. The  reaction mixture was then cooled slightly and 100 ml  (milliliters) of warm water was added and stirred well. Upon  standing, about 88 ml clear aqueous layer was removed and  the organic layer returned to the reaction flask for distilla› tion. After 62 g of atmospheric distillate was collected,  vacuum distillation was continued over about 45 minutes  with final temperature of 153°  C. at slightly less than 30  inches vacuum. Yield of the dark amber liquid was 115 g,  vacuum distillate was 99 g and contained 90.5% phenol and  6.8% water. Twenty grams of the dicyclopentadiene/phenol  condensate was dissolved in 20 g of toluene and 15 g of  n-heptane and extracted with 40 g water. The organic layer  was evaporated at ambient temperature to about 22 g and  then dried at 125°  C. to 130°  C. to give 19.3 g liquid with  a viscosity of 340 centistokes (about 400 cps).  It  needs to be pointed out that the molecular weights  shown in the examples are far short of the theoretical values.  The size exclusion chromatography readings (SEC) of  molecular weights used in this case are highly dependant on  hydrodynamic volume which causes the discrepancy.  Nevertheless, although such molecular weights are well  below theoretical and therefore erroneous on an absolute  basis, such molecular weights discern differences between  higher molecular weight and lower molecular weight mate› rials and can thus be used on a comparative basis.  A  Low Viscosity Phenol/Dicyclopentadiene Condensate  The following examples are illustrative of the invention  and its advantageous properties. In the examples as well as  elsewhere in this application, all parts and percentages are  by weight unless otherwise indicated.  hydroxyaryl can also be an individual hydroxyaryl or a  mixture of hydroxyaryls.  "Ex." means an example such as for the example num› bers;  "Diene" such as used in headings refers to the specific  diene employed in the example involved wherein:  "D-97" is dicyclopentadiene (Ultrene 97 of BF Goo› drich of Akron, Ohio), "D-99" is dicyclopentadiene  (Ultrene 99 of BF Goodrich), "L-99" is D-limonene  (Limonene  HP  of T2 Labs of Jacksonville, Fla.)  wherein the "99" indicates 99% purity;  the "Triflic Acid Cat. %" heading is the percent of  trifluoromethanesulfonic acid, by weight, based on the  weight of phenol in the reaction mixture of the example  involved:  NMP is _ti-methyl pyrrolidone; NC$_{6}$P is _ti-cyclohexyl  pyrrolidone; MeOH is methanol; H$_{2}$ 0  is water; and  PVP is poly(2-vinyl pyrrolidone);  the "Catalyst Modifier %" heading is the percent of the  retarder by weight, based on the weight of phenol in the  reaction mixture for the example involved;  the "Mole Ratio is the mole ratio of diene to phenol;  the "Reaction Conditions" heading provides the  beginning, "Start" temperature in degrees centigrade"( 0  C.)"; and the "Final"(°  C./hr)" for the Final temperature  and time of reaction before neutralization of the trif› luoromethanesulfonic acid catalyst and removal of phe› nol from the reactior mixture; 