Granted Patent B2

US 9,193,883 · App. 13/920,831 · Granted Nov 24, 2015

Abstract

Claims (71)

1. A phase change ink composition comprising:

an amorphous compound;

a crystalline compound;

a polyester polymer, wherein the polyester has a molecular weight of from about 500 to about 8,000 and a polydispersity index of from about 1.0 to about 8.0;

an optional synergist;

an optional dispersant; and

a colorant.

2. The phase change ink composition of claim 1 , wherein the polyester is comprised of large monomers prepared from monomers selected from the group consisting of 1,2-propylene glycol, naphthalene dicarboxylic acid, 1,3-propanediol, azelaic acid, abietic acid, glycerol, isophthalic acid, hexanediol, DL-mandelic acid, lactic acid, succinic acid, citric acid, and mixtures and combinations thereof.

3. The phase change ink composition of claim 1 , wherein the polyester is a bio-based polyester selected from the group consisting of poly(dimerized rosin-co-1,2-propylene glycol-co-naphthalene dicarboxylic acid-co-1,3-propanediol-co-azelaic acid-co-rosin fumarate) copolymer, poly(2-(2-hydroxy-2-((1R,4aR,4bR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carbonyl)oxy)ethyl) 6-(2-hydroxy-3-(((1R,4aR,4bR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carbonyl)oxy)propyl) naphthalene-2,6-dicarboxylate-co-isophthalic acid-co-1,6-hexanediol) co polymer, poly(mandelic acid-co-lactic acid) copolymer, and mixtures and combinations thereof.

4. The phase change ink composition of claim 1 , wherein the polyester is a bio-based, branched polyester resin comprising:

(i) the condensation product of:

(a) a hydroxyl donor;

(b) a cyclic polyhydroxyl acceptor; and

(c) an optional catalyst, and

(ii) a polyacid,

wherein said bio-based, branched polyester resin is greater than about 90% bio-based.

5. The phase change ink composition of claim 1 , wherein the polyester is a bio-based, branched polyester resin comprising:

(i) the condensation product of:

(a) a hydroxyl donor selected from the group consisting of glycerol, glycerol carbonate, trimethylolpropane, trimethylolethane and hexane triol;

(b) a cyclic polyhydroxyl acceptor selected from the group consisting of abietic acid, neoabietic acid, palustric acid, levopimaric acid, dihydroabietic acid, pimaric acid, isopimaric acid and combinations thereof;

(c) an optional catalyst; and

(ii) a polyacid selected from the group consisting of fumaric acid, maleic acid, succinic acid, itaconic acid, dodecylsuccinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, dodecane diacid and combinations thereof; wherein said bio-based, branched polyester resin is greater than about 90% bio-based.

6. The phase change ink composition of claim 1 , wherein the polyester is a bio-based, branched polyester resin comprising:

(i) the polycondensation product of:

(a) glycerine carbonate and/or glycerol; and

(b) a rosin acid selected from the group consisting of abietic acid, neoabietic acid, palustric acid, levopimaric acid, dihydroabietic acid, pimaric acid, isopimaric acid and combinations thereof; and

(ii) a polyacid selected from the group consisting of succinic acid, fumaric acid, maleic acid, itaconic acid, dodecylsuccinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid and azelaic acid.

7. The phase change ink composition of claim 1 , wherein the polyester is 1-decyl-12-methyl dodecanedioate of the formula

wherein n is an integer from 1 to 1,000.

8. The phase change ink composition of claim 1 , wherein the polyester is polymer is a branched polyester comprising a compound of the formula:

wherein R is an alkylene group, and wherein the alkylene group can be selected from linear and branched, saturated and unsaturated, cyclic and acyclic, and substituted and unsubstituted alkylene groups, and wherein heteroatoms either may or may not be present in the alkylene group;

wherein R′ is an alkylene group, and wherein the alkylene group can be selected from linear and branched, saturated and unsaturated, cyclic and acyclic, and substituted and unsubstituted alkylene groups, and wherein heteroatoms either may or may not be present in the alkylene group;

wherein all carbonyl carbons adjacent to R′ are separated by at least two atoms if the two atoms are separated by a single bond; or

wherein all carbonyl carbons adjacent to R′ are separated by at least 3 atoms covalently linked in series;

wherein m is an integer from about 1 to about 1,000; and

wherein n is an integer from about 1 to about 1,000.

9. The phase change ink of claim 1 , wherein the amorphous compound comprises a first ester of tartaric acid of the formula

wherein each of R 1 , R 2 , R 3 , R 4 , and R 5 is independently selected from an alkyl group, wherein the alkyl is straight, branched or cyclic, saturated or unsaturated, substituted or unsubstituted, having from about 1 to about 40 carbon atoms, or a substituted or unsubstituted aromatic or heteroaromatic group; and

wherein the crystalline compound comprises a second ester of tartaric acid of the formula

wherein each of R 6 and R 7 is independently selected from an aryl or a heteroaryl optionally substituted with a lower alkyl group, an alkoxy group, or a combination thereof, and wherein each n is independently selected from an integer from 0 to 3.

10. The phase change ink of claim 1 , wherein the crystalline compound is selected from the group consisting of dibenzyl L-tartrate, diphenethyl L-tartrate, bis(3-phenyl-1-propyl) L-tartrate, bis(2-phenoxyethyl) L-tartrate, diphenyl L-tartrate, bis-4-methylphenyl) L-tartrate, bis(4-methoxylphenyl) L-tartrate, bis(4-methylbenzyl) L-tartrate, bis(4-methoxybenzyl) L-tartrate, and stereoisomers and mixtures thereof; and wherein the amorphous compound is selected from the group consisting of bis(2-isopropyl-5-methylcyclohexyl) L-tartrate, (4-t-butylcyclohexyl)(cyclohexyl)-L-tartrate, stereoisomers and mixtures thereof.

11. The phase change ink of claim 1 , wherein the amorphous compound is a compound of the formula

12. The phase change ink of claim 1 , wherein the crystalline compound is a compound of the formula

13. A process comprising:

(1) incorporating into an ink jet printing apparatus a phase change ink composition comprising an amorphous compound; a crystalline compound; a polyester polymer, wherein the polyester has a molecular weight of from about 500 to about 8,000 and a polydispersity index of from about 1.0 to about 8.0; an optional synergist; an optional dispersant; and a colorant;

(2) melting the ink; and

(3) causing droplets of the melted ink to be ejected in an imagewise pattern onto a substrate.

14. The process of claim 13 , wherein the polyester is a bio-based, branched polyester resin comprising:

(i) the condensation product of:

(a) a hydroxyl donor selected from the group consisting of glycerol, glycerol carbonate, trimethylolpropane, trimethylolethane and hexane triol;

(b) a cyclic polyhydroxyl acceptor selected from the group consisting of abietic acid, neoabietic acid, palustric acid, levopimaric acid, dihydroabietic acid, pimaric acid, isopimaric acid and combinations thereof;

(c) an optional catalyst; and

(ii) a polyacid selected from the group consisting of fumaric acid, maleic acid, succinic acid, itaconic acid, dodecylsuccinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, dodecane diacid and combinations thereof;

wherein said bio-based, branched polyester resin is greater than about 90% bio-based.

15. The process of claim 13 , wherein the polyester wherein the polyester is 1-decyl-12-methyl dodecanedioate of the formula

wherein n is an integer from 1 to 1,000.

16. An ink jet printer stick or pellet containing a phase change ink composition comprising an amorphous compound; a crystalline compound; a polyester polymer, wherein the polyester has a molecular weight of from about 500 to about 8,000 and a polydispersity index of from about 1.0 to about 8.0; an optional synergist; an optional dispersant; and a colorant.

17. The ink jet printer stick or pellet of claim 16 , wherein the polyester is a bio-based, branched polyester resin comprising:

(i) the condensation product of:

(a) a hydroxyl donor selected from the group consisting of glycerol, glycerol carbonate, trimethylolpropane, trimethylolethane and hexane triol;

(b) a cyclic polyhydroxyl acceptor selected from the group consisting of abietic acid, neoabietic acid, palustric acid, levopimaric acid, dihydroabietic acid, pimaric acid, isopimaric acid and combinations thereof;

(c) an optional catalyst; and

(ii) a polyacid selected from the group consisting of fumaric acid, maleic acid, succinic acid, itaconic acid, dodecylsuccinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, dodecane diacid and combinations thereof;

wherein said bio-based, branched polyester resin is greater than about 90% bio-based.

18. The ink jet printer stick or pellet of claim 16 , wherein the polyester wherein the polyester is 1-decyl-12-methyl dodecanedioate of the formula

wherein n is an integer from 1 to 1,000.

19. The ink jet printer stick or pellet of claim 16 , wherein the amorphous compound comprises a first ester of tartaric acid of the formula

wherein each of R 1 , R 2 , R 3 , R 4 , and R 5 is independently selected from an alkyl group, wherein the alkyl is straight, branched or cyclic, saturated or unsaturated, substituted or unsubstituted, having from about 1 to about 40 carbon atoms, or a substituted or unsubstituted aromatic or heteroaromatic group; and

wherein the crystalline compound comprises a second ester of tartaric acid of the formula

wherein each of R 6 and R 7 is independently selected from an aryl or a heteroaryl optionally substituted with a lower alkyl group, an alkoxy group, or a combination thereof, and wherein each n is independently selected from an integer from 0 to 3.

20. The ink jet printer stick or pellet of claim 16 , wherein the polyester is wherein the polyester is comprised of large monomers prepared from monomers selected from the group consisting of 1,2-propylene glycol, naphthalene dicarboxylic acid, 1,3-propanediol, azelaic acid, abietic acid, glycerol, isophthalic acid, hexanediol, DL-mandelic acid, lactic acid, succinic acid, citric acid, and mixtures and combinations thereof.

Assignments (10)