Polyol acrylates for use in energy curable inks

Patent metadata

Field	Value
Publication number	US-9394401-B2
Application number	US-201213479051-A
Country	US
Kind code	B2
Filing date	May 23, 2012
Priority date	Nov 24, 2009
Publication date	Jul 19, 2016
Grant date	Jul 19, 2016

Abstract

Polyol acrylates are disclosed that are the reaction products of a modified polyol and a (meth)acrylic acid or derivative thereof. The modified polyols used in preparing the polyol acrylates are the reaction product of a natural oil or fatty carboxylic acid or derivative thereof with a polyol selected from the group consisting of polyester polyols, polyether polyols, polyester ether polyols and polyalcohols such that the natural oil or fatty carboxylic acid or derivative thereof is incorporated into the backbone of the polyol. The polyol acrylates are used to prepare pigment dispersions that are useful in formulating energy curable ink compositions.

First claim

What is claimed is:

1. A pigment dispersion comprising:
at least one polyol acrylate having a surface tension of less than 40 dynes/cm, wherein the polyol acrylate is the reaction product of a modified polyol and an equal or excess molar amount of a (meth)acrylic acid or a derivative thereof, wherein the modified polyol has an Acid Value in the range of 0.22 mg KOH/g to 2.48 mg KOH/g, a viscosity in the range of 51 cps to 1,955 cps at 25° C., and is a reaction product of a natural oil or fatty carboxylic acid or derivative thereof reacted with a polyol selected from the group consisting of polyether polyols, polyester polyols, polyester ether polyols, and polyalcohols, such that the natural oil or fatty carboxylic acid or derivative thereof is incorporated into the backbone of the polyol in an amount, based on the weight of the polyol, of about 5% to about 90% by weight for the natural oil or 10% to 90% by weight for the fatty carboxylic acid or derivative; and
from 15% to about 75% by weight of at least one pigment;
wherein the pigment dispersion has a yield stress of less than about 400 Pa.

2. The pigment dispersion of claim 1 , wherein the polyol is at least one polyester polyol that is a reaction product of a polyacid or derivative thereof, and a polyalcohol.

3. The pigment dispersion of claim 2 , wherein the polyacid or derivative thereof is selected from the group consisting of phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, methyl esters of phthalic acid, dimethyl phthalate, polyethylene terephthalate, trimellitic anhydride, pyromellitic dianhydride, pyromellitic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, adipic acid, glutaric acid, azealic acid, sebacic acid, dimer acid, and cyclohexanedicarboxylic acid and mixtures thereof.

4. The pigment dispersion of claim 2 , wherein the polyalcohol is selected from the group consisting of C2-C20 aliphatic and aromatic diols, 1,2-propane-diol, 1,3-propanediol, dipropylene glycol, tripropylene glycol, ethylene glycol, diethylene glycol, triethyleneglycol, tetraethylene glycol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, dihydroxymethyl cyclohexane, 2-butyl-2-ethyl-1,3 propandiol, polyethylene glycol, polypropylene glycol, glycerol, trimethylolpropane, pentaerythritol, higher functional polyalcohols and mixtures thereof.

5. The pigment dispersion of claim 2 , wherein the polyester polyol is the reaction product of a phthalic anhydride and a glycol selected from the group consisting of dipropylene glycol, tripropylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol, and mixtures thereof.

6. The pigment dispersion of claim 1 , wherein the polyol is at least one polyester ether polyol that is a reaction product of a polyacid or derivative thereof, a polyalcohol, and ethylene oxide, propylene oxide, butylene oxide, and mixtures thereof.

7. The pigment dispersion of claim 1 , wherein the polyol is a polyalcohol selected from the group consisting of diethylene glycol, triethylene glycol, glycerin, dipropylene glycol, tripropylene glycol, polyethylene glycol, polypropylene glycol, pentaerythritol, higher functional polyalcohols and mixtures thereof.

8. The pigment dispersion of claim 1 , wherein the polyol is at least one polyether polyol that is a reaction product of a polyalcohol and an alkylene oxide.

9. The pigment dispersion of claim 1 , wherein the polyol is end-capped with a molecule selected from the group consisting of lactides, C2 to C25 aliphatic hydroxycarboxylic acids, maleic anhydride, isocyanates, C2 to C3 alkyl carbonates, and mixtures thereof.

10. The pigment dispersion of claim 1 , wherein the polyol further comprises a chain-extension agent selected from group consisting of δ-valerolactone, ε-caprolactone and alkyl substituted ε-caprolactone.

11. The pigment dispersion of claim 1 , wherein the (meth)acrylic acid or derivative thereof has the following structural formula:

wherein R 2 is hydrogen, methyl or ethyl, aromatic, or C3 to C20 straight or branched alkyl, and Z is chloride, bromide, hydroxyl, ester or a mixture thereof.

12. The pigment dispersion of claim 1 , wherein the modified polyol has an iodine value of 0 to about 175.

13. The pigment dispersion of claim 1 , wherein the polyol acrylate has a molecular weight of about 100 to about 50,000 Daltons.

14. An energy curable ink composition comprising:
(a) a pigment dispersion comprising
(i) at least one polyol acrylate having a surface tension of less than 40 dynes/cm, wherein the polyol acrylate is the reaction product of a modified polyol and an equal or excess molar amount of a (meth)acrylic acid or derivative thereof, wherein the modified polyol has an Acid Value in the range of 0.22 mg KOH/g to 2.48 mg KOH/g, a viscosity in the range of 51 cps to 1.955 cps at 25° C., and is a reaction product of a natural oil or fatty carboxylic acid or derivative thereof reacted with a polyol selected from the group consisting of polyester polyols, polyether polyols, polyester ether polyols and polyalcohols, such that the natural oil or carboxylic acid or derivative thereof is incorporated into the backbone of the polyol in an amount, based on the weight of the polyol, of about 5% to about 90% by weight for the natural oil or about 10% to about 90% by weight for the fatty carboxylic acid or derivative; and
(ii) from 15% to about 75% by weight of the dispersion of at least one pigment;

wherein the pigment dispersion has a yield stress of less than about 400 Pa;
(b) an optional liquid resin; and
(c) optionally, at least one photoinitiator;
wherein the energy curable ink composition has a shortness index of about 5 or less.

15. The ink composition of claim 14 , wherein the liquid resin is selected from the group consisting of polyol acrylates, epoxy acrylates, polyurethane acrylates, acrylic acrylates, silicone acrylates, and mixtures thereof.

16. The ink composition of claim 15 , wherein the liquid resin comprises a polyol acrylate that has the same composition as the at least one polyol acrylate in the pigment dispersion.

17. The energy curable ink composition of claim 14 , wherein the pigment dispersion comprises about 15% to about 95% by weight of the ink composition.

18. The energy curable ink composition of claim 14 , wherein the amount of polyol acrylate in the pigment dispersion is about 10% to about 70% by weight of the pigment dispersion.

19. An energy curable ink composition comprising:
(a) at least one polyol acrylate having a surface tension of less than 40 dynes/cm, wherein the polyol acrylate is the reaction product of a modified polyol and an equal or excess molar amount of a (meth)acrylic acid or derivative thereof, wherein the modified polyol has an Acid Value in the range of 0.22 mg KOH/g to 2.48 mg KOH/g, a viscosity in the range of 51 cps to 1,955 cps at 25° C., and is a reaction product of a natural oil or fatty carboxylic acid or derivative thereof reacted with a polyol selected from the group consisting of polyester polyols, polyether polyols, polyester ether polyols and polyalcohol, such that the natural oil or carboxylic acid or derivative thereof is incorporated into the backbone of the polyol in an amount, based on the weight of the polyol, of about 5% to about 90% by weight for the natural oil or about 10% to about 90% by weight for the fatty carboxylic acid or derivative, and
(b) optiona

Assignees

• Yin Scott
• O'Brien Michael E
• Wang Mingzhe
• Stepan Co

Inventors

• Yin Scott
• O'Brien Michael E
• Wang Mingzhe

Classifications

• C08G63/48 Primary

  by unsaturated higher fatty oils or their acids; by resin acids · CPC title

• C09D167/08

  Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids · CPC title

• C08F283/01

  on to unsaturated polyesters {(C08F283/004 takes precedence)} · CPC title

• C08G63/676

  in which at least one of the two components contains aliphatic unsaturation · CPC title

• C08F283/02

  on to polycarbonates or saturated polyesters {(C08F283/004 takes precedence)} · CPC title