Light-colored rosin and rosin ester compositions

Patent metadata

Field	Value
Publication number	US-11034858-B2
Application number	US-201916687761-A
Country	US
Kind code	B2
Filing date	Nov 19, 2019
Priority date	Dec 21, 2018
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

A three-step method to prepare a light-colored rosin ester is disclosed wherein at least in one of the steps (a) and (c) a co-catalyst is applied and wherein at least in one of the steps (a) and (c) a disproportionation catalyst is applied. In the second step, a distilled rosin is obtained which is esterified with a polyol into a light-colored rosin ester. In one embodiment, the co-catalyst has a triplet formation quantum yield (ϕT) of greater than 0.5 and a triplet lifetime (τT) of greater than 0.5 microseconds. In another embodiment, the co-catalyst is selected from acridone, anthrone, 9-fluorenone, thioxanthone, xanthone, derivatives and combinations thereof.

First claim

The invention claimed is:

1. A rosin ester prepared by reacting a rosin composition with one or more polyhydric alcohols and, optionally one or more monocarboxylic acids, and optionally one or more polycarboxylic acids in the presence of 0.001 wt. % to 5.0 wt. % of a co-catalyst and 0.001 wt. % to 5.0 wt. % of a disproportionation catalyst, wherein the co-catalyst comprises a compound represented by the formula:

wherein n=0, 1 or 2;
X represents oxygen, sulphur, nitrogen, or carbon;
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 and Z 8 are the same or different and each represents carbon or nitrogen;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 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 hydroxyalkyl 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, and a glucopyranosyloxy group,

wherein the rosin ester has a neat Gardner color of less than 3, an acid number value less than 30 mg KOH/gram, a PAN value less than 30%, and a hydroxyl number less than 30 mg KOH/g; and
wherein the rosin ester contains a residual amount of co-catalyst ranging from >0.00001% to <100% of the co-catalyst used initially for the reaction.

2. The rosin ester of claim 1 , wherein the reaction further comprises 0.001 wt. % to 5.0 wt. % of a disproportionation catalyst, and wherein the disproportionation catalyst is selected from the group of 2,2′thiobisphenols, 3,3′-thiobisphenols, 4,4′-thiobis(resorcinol), 1,1′-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, Pd/C, iodine, iodides, sulfides, poly-t-butylphenoldisulfide, 4,4′thiobis(2-t-butyl-5-methylphenol, nonylphenol disulfide oligomers, amylphenol disulfide polymer, and combinations thereof.

3. A method for preparing a rosin ester comprising:
a) heating a rosin in a substantially inert environment;
b) distilling the resulting rosin composition under a reduced pressure; and
c) reacting the distilled rosin composition with one or more polyhydric alcohols and, optionally one or more monocarboxylic acids, and optionally one or more polycarboxylic acids,
wherein at least in one of the steps (a) and (c) a co-catalyst and a disproportionation catalyst are applied, and
wherein the co-catalyst comprises a compound represented by the formula:

wherein n=0, 1 or 2;
X represents oxygen, sulphur, nitrogen, or carbon;
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 and Z 8 are the same or different and each represents carbon or nitrogen;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 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 hydroxyalkyl 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, and a glucopyranosyloxy group,

wherein the disproportionation catalyst is present in an amount of from 0.001 wt. % to 5.0 wt. %, based on the total weight of chemical substances applied in steps (a) and (c);
wherein the co-catalyst is present in an amount of from 0.001 wt. % to 5.0 wt. %, based on the total weight of chemical substances applied in steps (a) and (c) and wherein the co-catalyst has a triplet formation quantum yield (ϕT) of greater than 0.5 and a triplet lifetime (τT) of greater than 0.5 microseconds; and
wherein the rosin ester contains a residual amount of the co-catalyst ranging from >0.00001% to <100% of the co-catalyst used in the at least one of the steps (a) and (c).

4. The method of claim 3 , wherein the co-catalyst comprises at least one of acridone, anthrone, 9-fluorenone, thioxanthone, xanthone, derivatives, and combinations thereof.

5. The method of claim 3 , wherein the disproportionation catalyst is selected from the group of 2,2′thiobisphenols, 3,3′-thiobisphenols, 4,4′-thiobis(resorcinol), 1,1′-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, Pd/C, iodine, iodides, sulfides, poly-t-butylphenoldisulfide, 4,4′thiobis(2-t-butyl-5-methylphenol, nonylphenol disulfide oligomers, amylphenol disulfide polymer, and combinations thereof.

6. The method of claim 3 , wherein the rosin in step (a) comprises a tall oil rosin, a gum rosin, a wood rosin, a hydrogenated rosin, a dehydrogenated rosin, a rosin purified by distillation or crystallization, and combinations thereof.

7. The method of claim 3 , wherein the one or more polyhydric alcohols has an average hydroxyl functionality from 2 to 10 and wherein the polyhydric alcohol comprises from 2 to 30 carbon atoms.

Assignees

• Kraton Polymers Llc

Inventors

• Schaapman Mark C
• Lange Jos H M

Classifications

• C08L93/04 Primary

  Rosin · CPC title

• C09F1/02

  Purification · CPC title

• C09D5/004

  Reflecting paints; Signal paints · CPC title

• C09D193/04

  Rosin · CPC title

• C09F1/04 Primary

  Chemical modification, e.g. esterification (resin soaps C11D) · CPC title