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1. (WO2019006431) LIGHT COLOR ROSIN ESTER COMPOSITIONS AND METHODS OF MAKING SAME
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CLAIMS

1. A method for producing a light color rosin comprising:

contacting one or more rosins with a co-catalyst to produce a mixture;

heating the mixture to a temperature to produce a light color rosin;

wherein the co-catalyst comprises compounds represented by formula:


wherein n = 0, 1 or 2;

X represents oxygen, sulphur, nitrogen, or carbon;

Zi, Z2, Z3, Z4, Z5, Z6, Z7 and Z8 are the same or different and each represents carbon or nitrogen;

Ri , R2, R3, R4, R5, R6, R7 and R8 are the same or different and each is independently selected from the group of hydrogen, an alkyl group, an aryl group, an arylalkyl, an alkenyl group, an arylalkenyl group, an alkynyl group, an arylalkynyl group, a cycloalkyl group, a cycloalkylalkyl group, an alkylene group, a cycloalkylalkylene group, an alkynylene group, a phenyl group, a tolyl group, a naphtyl group, a pyridyl group, a furyl group, an acyl group, a propionyl group, a formyl group, a benzoyl group, a acetoxy group, a halogen, an alkoxy group, an amino group, a benzyl, halogen substituted benzyl group, a alkyl substituted benzyl group, a alkoxy substituted benzyl group, a halogen substituted aryl group, an alkyl substituted aryl group, an alkoxy substituted aryl group, a dialkylamino group, a monoalkylamino group, a monoalkylamido group, a dialkylamido group, a cyano group, a hydroxymethyl group, a hydroxy alkyl group, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a trifluoromethylsulfonyl group, a nitro group, a carboxyl group, a hydroxyl group, an alkoxyalkyl group, an aryloxyalkyl group, a sulfamoyl group, a dimethylsulfamido group, a sulfhydryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfanyl group, an arylsulfanyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, a carbamoyl group, a carbonyl chloride group, a phosphine group, a phosphate group, a phosphodiester group, a phosphonic acid group, an oxiranylalkyl group, a carboxyalkyl group, a carboxyalkyl group, a glucopyranosyl group or a glucopyranosyloxy group.

2. The method of claim 1, wherein the co-catalyst has a triplet formation quantum yield (φτ) of greater than 0.5 and a triplet lifetime (τχ) of greater than 0.5 microseconds.

3. The method of claim 1, wherein the co-catalyst is selected from the group of acridone, anthrone, 9-fluorenone, thioxanthone, xanthone, derivatives, and combinations thereof.

4. The method of any of claims 1-3 for producing a light color rosin, wherein the light color rosin has an initial (neat) Gardner color, as determined according to ASTM D 1544-04 (2010), of less than 10.

5. The method of any of claims 1-3, further comprising contacting the mixture with a disproportionation catalyst,

wherein the disproportionation catalyst is selected from 2,2'thiobisphenols, 3,3'-thiobisphenols, 4,4'-thiobis(resorcinol), l,l'-thiobis(pyrogallol), 4,4'-thiobis(6-t-butyl-m-cresol),

4,4'-thiobis(6-t-butyl-o-cresol) thiobisnaphthols, 2,2'-thio-bisphenols, 3,3'-thio-bis phenols, palladium, nickel, platinum, iodines, iodides, sulfides, poly-t-butylphenoldisulfide, 4,4'thiobis(2-i-butyl-5-methylphenol, nonylphenol disulfide oligomers, amylphenol disulfide polymer, and combinations thereof;

wherein the disproportionation catalyst is present in an amount of from 0.01 wt. % to 5.0 wt. %, and the co-catalyst is present in an amount of from 0.01 wt.% to 5.0 wt.%, based on the total weight of the rosin or rosin ester.

6. The method of any of claims 1-3 for producing a light color rosin,

wherein the one or more rosins comprise any of a tall oil rosin, a gum rosin, a wood rosin, a disproportionated rosin, a fortified rosin and combinations thereof, and

wherein the one or more rosins have an acid number ranging from 120 mg KOH/ gram to 190 mg KOH/gram.

7. A method for producing a light color rosin ester, the method comprising:

contacting one or more rosins with a co-catalyst, one or more polyhydric alcohols, optionally one or more of a monocarboxylic acid, and optionally one or more of a

polycarboxylic acid to produce a mixture;

heating the mixture to a temperature to produce a light color rosin ester;

wherein the co-catalyst comprises compounds represented by formula:

wherein n = 0, 1 or 2;

X represents oxygen, sulphur, nitrogen, or carbon;

Zi,Z2, Z3, Z4, Z5, Z6, Z7 and Z8 are the same or different and each represents carbon or nitrogen;

Ri , R2, R3, R4, R5, R6, R7 and R8 are the same or different and each is independently selected from the group of hydrogen, an alkyl group, an aryl group, an arylalkyl, an alkenyl group, an arylalkenyl group, an alkynyl group, an arylalkynyl group, a cycloalkyl group, a cycloalkylalkyl group, an alkylene group, a cycloalkylalkylene group, an alkynylene group, a phenyl group, a tolyl group, a naphtyl group, a pyridyl group, a furyl group, an acyl group, a propionyl group, a formyl group, a benzoyl group, a acetoxy group, a halogen, an alkoxy group, an amino group, a benzyl, halogen substituted benzyl group, a alkyl substituted benzyl group, a alkoxy substituted benzyl group, a halogen substituted aryl group, an alkyl substituted aryl group, an alkoxy substituted aryl group, a dialkylamino group, a monoalkylamino group, a monoalkylamido group, a dialkylamido group, a cyano group, a hydroxymethyl group, a hydroxy alkyl group, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a trifluoromethylsulfonyl group, a nitro group, a carboxyl group, a hydroxyl group, an alkoxyalkyl group, an aryloxyalkyl group, a sulfamoyl group, a dimethylsulfamido group, a sulfhydryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfanyl group, an arylsulfanyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, a carbamoyl group, a carbonyl chloride group, a phosphine group, a phosphate group, a phosphodiester group, a phosphonic acid group, an oxiranylalkyl group, a carboxyalkyl group, a carboxyalkyl group, a glucopyranosyl group or a glucopyranosyloxy group.

8. The method of claim 7, further comprising contacting the mixture with a disproportionation catalyst selected from the group of 2,2'-thiobisphenols, 3,3'-thiobisphenols, 4,4'-thiobis(resorcinol), l,l'-thiobis(pyrogallol), 4,4'-thiobis(6-t-butyl-m-cresol), 4,4'-thiobis(6-t- butyl-o-cresol) thiobisnaphthols, 2,2'-thio-bisphenols, 3,3'-thio-bis phenols, palladium, nickel, platinum, iodine, iodides, sulfides, poly-t-butylphenoldisulfide, 4,4'-thiobis(2-i-butyl-5-methylphenol, nonylphenol disulfide oligomers, palladium, amylphenol disulfide polymer and combinations thereof.

9. The method of any of claim 7-8, wherein the one or more rosins comprise any of a tall oil rosin; a gum rosin; a wood rosin; a disproportionated rosin; a rosin fortified with any of fumaric acid, maleic acid, acrylic acid, maleic anhydride, citraconic acid, mesaconic acid, itaconic acid and esters derived therefrom; and combinations thereof.

10. The method of any of claim 7-8,

wherein the one or more polyhydric alcohols comprise an average hydroxyl functionality from 2 to 10, wherein the one or more polyhydric alcohols are present in an amount of from 5 wt.% to 40 wt.% based on the total weight of the rosin ester;

wherein the one or more polyhydric alcohols comprise at least one of glycol, propylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, neopentylglycol, trimethylene glycol, glycerol, trimethylolpropane, trimethylolethane, pentaerythritol, pentaerythritol technical grade, dipentaerythritol, tripentaerythritol, 1,4-cyclohexanediol, polyethylene glycol, polyglycerol, polyglycerol technical grade, polyglycerol-3, polyglycerol-4, cyclohexane-1,4-dimethanol, tricyclo[5.2.1.0(2.6)]decane-4,8-dimethanol, hydrogenated bisphenol A (4,4'-Isopropylidenedicyclohexanol), mannitol, sorbitol, xylitol, maltitol, lactitol, and combinations thereof;

wherein the one or more monocarboxylic acids comprise any of formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, cerotic acid, benzoic acid, cyclopropanecarboxylic acid, cyclopentanecarboxylic acid, cyclohexanecarboxylic acid, linoleic acid, alpha-linolenic acid, elaidic acid, sapienic acid, arachidonic acid, myristoleic acid, palmitoleic acid, oleic acid, myristic acid, isostearic acid, or combinations thereof, and wherein the one or more monocarboxylic acids are present in an amount of from 15 wt.% to 90 wt.% based on the total weight of the rosin ester, and

wherein the one or more polycarboxylic acids comprise from 2 to 54 carbon atoms. 11. The method of any of claim 7-8, further comprising contacting the mixture with an esterification catalyst, wherein the esterification catalyst comprises any of acetic acid, p- toluenesulfonic acid, methanesulfonic acid, hypophosphorous acid, sulfuric acid, alkaline metal hydroxides, calcium hydroxide, metal oxides, calcium oxide, magnesium oxide, aluminum oxide, calcium bis-monoethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate and combinations thereof.

12. A method to provide a light color rosin ester, the method comprising:

contacting one or more rosins with a co-catalyst, a disproportionation catalyst, one or more polyhydric alcohols and, optionally one or more monocarboxylic acids, and optionally one or more polycarboxylic acids, to produce a mixture;

wherein the co-catalyst has a triplet formation quantum yield (φτ) of greater than 0.5 and a triplet lifetime (ττ) of greater than 0.5 microseconds; and

wherein the rosin ester composition exhibits a change of 5.0 or less Gardner color units when heated to a temperature of 177°C for a period of 96 hours;

wherein the rosin ester has a PAN number of equal to or less than 25; and

wherein the rosin ester has at least 30 wt. dehydroabietic acid

13. A rosin ester produced by the method of claim 12.

14. A composition comprising the rosin ester of claim 13, wherein the composition is any of a road marking composition, an adhesive composition, and a pressure sensitive adhesive composition.