US 7,449,515 B2 · Phase change inks containing compounds derived from isocyanate, unsaturated alcohol, and polyol

A phase change ink comprising a colorant, an initiator, and a phase change ink carrier, said carrier comprising (A) a first isocyanate-derived compound which is the reaction product of a mixture comprising (1) an isocyanate;

and (2) a component comprising (a) an alcohol having at least one ethylenic unsaturation;
(b) an amine having at least one ethylenic unsaturation;
(c) an acid having at least one ethylenic unsaturation;
or (d) mixtures thereof, (B) a second isocyanate-derived compound which is the reaction product of (1) a diisocyanate;
(2) a monoalcohol having exactly one hydroxyl group and having at least one ethylenic unsaturation;
and (3) a polyol having two or more hydroxyl groups, (C) an optional phase change inducing component, said phase change inducing component containing at least one hydroxyl group, said phase change inducing component having a melting point of about 40° or higher, and (D) an optional curable viscosity modifying ester, said ink being curable upon exposure to ultraviolet radiation, provided that at least one of (I) or (II) is true;
(I) the monoalcohol having exactly one hydroxyl group and having at least one ethylenic unsaturation is a vinyl ether of the formula
wherein R33 is (i) an alkyl group, including linear and branched, saturated and unsaturated, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an aryl group, including substituted and unsubstituted aryl group, and wherein hetero atoms either may or may not be present in the aryl group, (iii) an arylalkyl group, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group, or (iv) an alkylaryl group including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the alkylaryl group, or (II) the ink contains a curable viscosity modifying ester of the formula
wherein Ra is (i) an alkyl group, including linear and branched, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an arylalkyl group, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either aryl or the alkyl portion of the arylalkyl group, or (iii) an alkylaryl group, including substituted and unsubstituted alkylaryl group, wherein the alkyl group portion of the alkylaryl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or alkyl portion of the alkylaryl group, and herein Rb is (i) an alkyl group having at least one ethylenic unsaturation therein, including linear and branched, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an arylalkyl group having at least one ethylenic unsaturation therein, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group, or (iii) an alkylaryl group having at least one ethylenic unsaturation therein, including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either aryl or alkyl portion of the alkylaryl group.

6 more elements

A phase change ink comprising a colorant, an initiator, and a phase change ink carrier, said carrier comprising (A) a first isocyanate-derived compound which is the reaction product of a mixture comprising (1) an isocyanate;

and (2) a component comprising (a) an alcohol having at least one ethylenic unsaturation;
(b) an amine having at least one ethylenic unsaturation;
(c) an acid having at least one ethylenic unsaturation;
or (d) mixtures thereof, (B) a second isocyanate-derived compound which is the reaction product of (1) a diisocyanate;
(2) a monoalcohol having exactly one hydroxyl group and having at least one ethylenic unsaturation;
and (3) a polyol having two or more hydroxyl groups, (C) an optional phase change inducing component, said phase change inducing component containing at least one hydroxyl group, said phase change inducing component having a melting point of about 40° or higher, and (D) an optional curable viscosity modifying ester, said ink being curable upon exposure to ultraviolet radiation, wherein the second isocyanate-derived compound is (a) of the formula
(b) of the formula
(c) of the formula
wherein each branch of the compound has the following four possibilities:
(1) R1, R2, and R5═CH3;
R3, R4, R6, R7, and R8═H;
(2) R1, R5, and R6═CH3;
R2, R3, R4, R7, and 8═H;
(3) R3, R7, and R8═CH3;
R1, R2, R4, R5, and R6═H;
(4) R3, R4, and R7═CH3;
R1, R2, R5, R6, and R8═H;
(5) R9, R10, and R13═CH3;
R11, R12, R14, R15, and R16═H;
(6) R9, R13, and R14═CH3;
R10, R11, R12, R15, and R16═H;
(7) R11, R15, and R16═CH3;
R9, R10, R12, R13, and R14═H;
(8) R11, R12, and R15═CH3;
R9, R10, R13, R14, and R16═H;
(9) R17, R18, and R21═CH3;
R19, R20, R22, R23, and R24═H;
(10) R17, R21, and R22═CH3;
R18, R19, R20, R23, and R24═H;
(11) R19, R23, and R24═CH3;
R17, R18, R20, R21, and R22═H;
(12) R19, R20, and R23═CH3;
R17, R18, R21, R22, and R24═H;
(d) of the formula
wherein each branch of the compound has the following four possibilities:
(1) R1, R2, and R5═CH3;
R3, R4, R6, R7, and R8═H;
(2) R1, R5, and R6═CH3;
R2, R3, R4, R7, and R8═H;
(3) R3, R7, and R8═CH3;
R1, R2, R4, R5, and R6═H;
(4) R3, R4, and R7═CH3;
R1, R2, R5, R6, and R8═H;
(5) R9, R10, and R13═CH3;
R11, R12, R14, R15, and R16═H;
(6) R9, R13, and R14═CH3;
R10, R11, R12, R15, and R16═H;
(7) R11, R15, and R16═CH3;
R9, R10, R12, R13, and R14═H;
(8) R11, R12, and R15═CH3;
R9, R10, R13, R14, and R16═H;
(9) R1′, R2′, and R5′═CH3;
R3′, R4′, R6′, R7′, and R8′═H;
(10) R1′, R5′, and R6′═CH3;
R2′, R3′, R4′, R7′, and R8′═H;
(11) R3′, R7′, and R8′═CH3;
R1′, R2′, R4′, R5′, and R6′═H;
(12) R3′, R4′, and R7′═CH3;
R1′, R2′, R5′, R6′, and R8′═H;
(13) R9′, R10′, and R13′═CH3;
R11′, R12′, R14′, R15′, and R16′═H;
(14) R9′, R13′, and R14′═CH3;
R10′, R11′, R12′, R15′, and R16′═H;
(15) R11′, R15′, and R16′═CH3;
R9′, R10′, R12′, R13′, and R14′═H;
(16) R11′, R12′, and R15′═CH3;
R9′, R10′, R13′, R14′, and R16′═H, and wherein R1′, R2′, R3′, R4′, R5′, R6′, R7′, R8′, R9′, R10′, R11′, R12′, R13′, R14′, R1g, and R16′ represent the second occurrence of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16;
or (e) mixtures thereof.

65 more elements

A phase change ink comprising a colorant, an initiator, and a phase change ink carrier, said carrier comprising (A) a first isocyanate-derived compound which is the reaction product of a mixture comprising (1) an isocyanate;

and (2) a component comprising (a) an alcohol having at least one ethylenic unsaturation;
(b) an amine having at least one ethylenic unsaturation;
(c) an acid having at least one ethylenic unsaturation;
or (d) mixtures thereof, (B) a second isocyanate-derived compound which is the reaction product of (1) a diisocyanate;
(2) a monoalcohol having exactly one hydroxyl group and having at least one ethylenic unsaturation;
and (3) a polyol having two or more hydroxyl groups, (C) an optional phase change inducing component, said phase change inducing component containing at least one hydroxyl group, said phase change inducing component having a melting point of about 40° or higher, and (D) an optional curable viscosity modifying ester, said ink being curable upon exposure to ultraviolet radiation, wherein the monoalcohol having exactly one hydroxyl group and having at least one ethylenic unsaturation is a vinyl ether of the formula
wherein R33 is (i) an alkyl group, including and branched, saturated and unsaturated, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an aryl group, including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group, (iii) an arylalkyl group, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group, or (iv) an alkylaryl group, including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the alkylaryl group.

4 more elements

A phase change ink comprising a colorant, an initiator, and a phase change ink carrier, said carrier comprising (A) a first isocyanate-derived compound which is the reaction product of a mixture comprising (1) an isocyanate;

and (2) a component comprising (a) an alcohol having at least one ethylenic unsaturation;
(b) an amine having at least one ethylenic unsaturation;
(c) an acid having at least one ethylenic unsaturation;
or (d) mixtures thereof, (B) a second isocyanate-derived compound which is the reaction product of (1) a diisocyanate;
(2) a monoalcohol having exactly one hydroxyl group and having at least one ethylenic unsaturation;
and (3) a polyol having two or more hydroxyl groups, (C) an optional phase change inducing component, said phase change inducing component containing at least one hydroxyl group, said phase change inducing component having a melting point of about 40° or higher, and (D) an optional curable viscosity modifying ester, said ink being curable upon exposure to ultraviolet radiation, wherein the ink contains a curable viscosity modifying ester, wherein the curable viscosity modifying ester is of the formula
wherein Ra is (i) an alkyl group, including linear and branched, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an arylalkyl group, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group, or (iii) an alkylaryl group, including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the alkylaryl group, and wherein Rb is (i) an alkyl group having at least one ethylenic unsaturation therein, including linear and branched, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an arylalkyl group having at least one ethylenic unsaturation therein, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group, or (iii) an alkylaryl group having at least one ethylenic unsaturation therein, including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the alkylaryl group.

4 more elements

A process which comprises (I) incorporating into an ink jet printing apparatus a phase change ink comprising a colorant, an initiator, and a phase change ink carrier, said carrier comprising (A) a first isocyanate-derived compound which is the reaction product of a mixture comprising (1) an isocyanate;

and (2) a component comprising (a) an alcohol having at least one ethylenic unsaturation;
(b) an amine having at least one ethylenic unsaturation;
(c) an acid having at least one ethylenic unsaturation;
or (d) mixtures thereof, (B) a second isocyanate-derived compound which is the reaction product of (1) a diisocyanate;
(2) a monoalcohol having exactly one hydroxyl group and having at least one ethylenic unsaturation;
and (3) a polyol having two or more hydroxyl groups, (C) an optional phase change inducing component, said phase change inducing component containing at least one hydroxyl group, said phase change inducing component having a melting point of about 40° or higher, and (D) an optional curable viscosity modifying ester, said ink being curable upon exposure to ultraviolet radiation, provided that at least one of (α) or (β) is true;
(α) the monoalcohol having exactly one hydroxyl group and having at least one ethylenic unsaturation is a vinyl ether of formula
wherein R33 is (i) an alkyl group, including and branched, saturated and unsaturated, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an aryl group, including substituted and unsubstituted aryl groups, and wherein hetero atoms either may or may not be present in the aryl group, (iii) an arylalkyl group, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group, or (iv) an alkylaryl group, including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, saturated or unsaturated, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the alkylaryl group, or (β) the ink contains a curable viscosity modifying ester of the formula
wherein Ra is (i) an alkyl group, including linear and branched, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an arylalkyl group, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either aryl or the alkyl portion of the arylalkyl group, or (iii) an alkylaryl group, including substituted and unsubstituted alkylaryl group, wherein the alkyl group portion of the alkylaryl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or alkyl portion of the alkylaryl group, and herein Rb is (i) an alkyl group having at least one ethylenic unsaturation therein, including linear and branched, cyclic and acyclic, and substituted and unsubstituted alkyl groups, and wherein hetero atoms either may or may not be present in the alkyl group, (ii) an arylalkyl group having at least one ethylenic unsaturation therein, including substituted and unsubstituted arylalkyl groups, wherein the alkyl portion of the arylalkyl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either the aryl or the alkyl portion of the arylalkyl group, or (iii) an alkylaryl group having at least one ethylenic unsaturation therein, including substituted and unsubstituted alkylaryl groups, wherein the alkyl portion of the alkylaryl group can be linear or branched, cyclic or acyclic, and substituted or unsubstituted, and wherein hetero atoms either may or may not be present in either aryl or alkyl portion of the alkylaryl group, (II) melting the ink;
(III) causing droplets of the melted ink to be ejected in an imagewise pattern onto a substrate;
and (IV) exposing the imagewise pattern to ultraviolet radiation.

8 more elements

Phase change inks containing compounds derived from isocyanate, unsaturated alcohol, and polyol

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Phase change inks containing compounds derived from isocyanate, unsaturated alcohol, and polyol

Life of this patent

Abstract

Claims28