Phase change ink compositions comprising crystalline sulfone compounds and derivatives thereof
View Patent ↗A phase change ink composition comprising an amorphous component, a crystalline component comprises a sulfone compound or derivatives thereof, and optionally, a colorant, which are suitable for ink jet printing, including printing on coated paper substrates.
1. A phase change ink comprising:
an amorphous component comprises an ester of tartaric acid of Formula II or an ester of citric acid of Formula III
wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently an alkyl group, wherein the alkyl can be straight, branched or cyclic, saturated or unsaturated, substituted or unsubstituted, having from about 1 to about 40 carbon atoms, or an substituted or unsubstituted aromatic or heteroaromatic group, and mixtures thereof; and
a crystalline component being a sulfone compound having the following
R 6 —SO 2 —R 7 Formula I
wherein R 6 and R 7 can be the same or different, and wherein R 6 and R 7 each, independently of the other is selected from the group consisting of (i) an alkyl group, which can be a linear or branched, cyclic or acyclic, substituted or unsubstituted, saturated or unsaturated, alkyl group, and wherein heteroatoms may optionally be present in the alkyl group having from about 1 to about 40 carbon atoms; (ii) an arylalkyl group, which can be a substituted or unsubstituted arylalkyl group, wherein the alkyl portion of arylalkyl group can be linear or branched, cyclic or acyclic, substituted or unsubstituted, saturated or unsaturated, and wherein heteroatoms may optionally be present in either the aryl portion or the alkyl portion of the arylalkyl group having from about 4 to about 40 carbon atoms; and (iii) an aromatic group, which can be a substituted or unsubstituted aromatic group, wherein the substituent can be a linear, branched, cyclic or acyclic alkyl group and wherein heteroatoms may optionally be present in the aromatic group having from about 3 to about 40 carbon atoms, and mixtures thereof; wherein the phase change ink crystallizes in less than 15 seconds.
2. The phase change ink of claim 1 , wherein the tartaric acid backbone is selected from L-(+)-tartaric acid, D-(−)-tartaric acid, DL-tartaric acid, or mesotartaric acid, and mixtures thereof.
3. A phase change ink comprising:
an amorphous component comprises an ester of tartaric acid of Formula II or an ester of citric acid of Formula III
wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently an alkyl group, wherein the alkyl can be straight, branched or cyclic, saturated or unsaturated, substituted or unsubstituted, having from about 1 to about 40 carbon atoms, or an substituted or unsubstituted aromatic or heteroaromatic group, and mixtures thereof; and
a crystalline component being a sulfone compound having the following Formula I
R 6 —SO 2 —R 7 Formula I
each R 6 and R 7 is independently alkyl, or aryl, optionally substituted with one or more halo, amino, hydroxy, or cyano groups and combinations thereof, or R 6 and R 7 taken together with the S atom to which they are attached form a heterocyclic ring; wherein the crystalline and amorphous component are present in a crystalline/amorphous weight ratio of from about 60:40 to about 95:5.
4. The phase change ink of claim 3 , wherein the crystalline component is selected from the group consisting of diphenyl sulfone, dimethyl sulfone, bis(4-hydroxyphenyl) sulfone, bis(4-aminophenyl) sulfone, bis(3-aminophenyl) sulfone, bis(4-chlorophenyl) sulfone, bis(4-fluorophenyl) sulfone, 2-hydroxyphenyl-4-hydroxyphenyl sulfone, phenyl-4-chlorophenyl sulfone, phenyl-2-aminophenyl sulfone, bis(3-amino-4-hydroxyphenyl) sulfone, dibenzyl sulfone, methylethyl sulfone, diethyl sulfone, methylisopropyl sulfone, ethylisopropyl sulfone, di-n-butyl sulfone, divinyl sulfone, methyl-2-hydroxyethyl sulfone, methylchloromethyl sulfone, sulfolane, 3-sulfolene, and mixtures thereof.
5. The phase change ink of claim 3 being in solid state at room temperature.
6. The phase change ink of claim 3 having a jetting temperature of from about 100 to about 140° C.
7. The phase change ink of claim 3 , wherein the amorphous and crystalline components are miscible in the liquid state.
8. A phase change ink comprising:
an amorphous component comprises an ester of tartaric acid of Formula II or an ester of citric acid of Formula III
wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently an alkyl group, wherein the alkyl can be straight, branched or cyclic, saturated or unsaturated, substituted or unsubstituted, having from about 1 to about 40 carbon atoms, or an substituted or unsubstituted aromatic or heteroaromatic group, and mixtures thereof; and
a crystalline component being a sulfone compounds having the following Formula I
R 6 —SO 2 —R 7 Formula I
wherein R 6 and R 7 can be the same or different, and wherein R 6 and R 7 each, independently of the other is selected from the group consisting of (i) an alkyl group, which can be a linear or branched, cyclic or acyclic, substituted or unsubstituted, saturated or unsaturated, alkyl group, and wherein heteroatoms may optionally be present in the alkyl group having from about 1 to about 40 carbon atoms; (ii) an arylalkyl group, which can be a substituted or unsubstituted arylalkyl group, wherein the alkyl portion of arylalkyl group can be linear or branched, cyclic or acyclic, substituted or unsubstituted, saturated or unsaturated, and wherein heteroatoms may optionally be present in either the aryl portion or the alkyl portion of the arylalkyl group having from about 4 to about 40 carbon atoms; and (iii) an aromatic group, which can be a substituted or unsubstituted aromatic group, wherein the substituent can be a linear, branched, cyclic or acyclic alkyl group and wherein heteroatoms may optionally be present in the aromatic group having from about 3 to about 40 carbon atoms and mixtures thereof.
9. The phase change ink of claim 8 , wherein each R 6 and R 7 is independently phenyl or benzyl optionally substituted with one or more halo, amino, hydroxy, cyano or combinations thereof.
10. The phase change ink of claim 8 , wherein each R 6 and R 7 is independently methyl, ethyl, isopropyl, n-butyl, or vinyl optionally substituted with one or more hydroxyl, cyano, or combinations thereof.
11. The phase change ink of claim 8 , wherein the crystalline component is present in an amount of from about 60 percent to about 95 percent by weight of the total weight of the phase change ink.
12. The phase change ink of claim 8 , wherein the amorphous component is present in an amount of from about 5 percent to about 40 percent by weight of the total weight of the phase change ink.
13. The phase change ink of claim 8 further comprising a colorant selected from the group consisting of a pigment, dye or mixtures thereof.
14. The phase change ink of claim 8 , wherein the crystalline/amorphous ratio is from about 60:40 to about 95:5.
15. The phase change ink of claim 8 , wherein the crystalline component has a viscosity of less than 10 cps at a temperature of about 140° C.
16. The phase change ink of claim 8 , wherein the crystalline component has T melt of less than 150° C.
17. The phase change ink of claim 8 , wherein the crystalline component has T crys of greater than 60° C.
18. The phase change ink of claim 8 having a viscosity of from about 1 to about 22 cps in a jetting range of from about 100 to about 140° C.
19. The phase change ink of claim 8 having a viscosity of greater than about 1×10 6 cps at room temperature.