Cyclic bisamides useful in formulating inks for phase-change printing
View Patent ↗Cyclic bisamides may be used to formulate inks for jet ink printing. The cyclic bisamide may be prepared from a cyclic diamine and acylic monocarboxylic acids. Conversely, the cyclic bisamide may be prepared from a cyclic diacid and acylic monoamines. The performance properties of the product may be enhanced by adding some additional difunctional reactant(s), e.g., diacid or diamine. A blend of bisamides may provide better performance properties than either of the component bisamides alone, where the blend includes at least one cyclic bisamide. The bisamides, in combination with an image-forming material, and optionally in combination with other materials, is taken to a molten form and the applied to a substrate to provide a printed substrate.
1. A process of making a cyclic bisamide of structure I
comprising reacting under amidification conditions reactants comprising a diamine of structure (IV)
and a monocarboxylic acid of the formula R 1 —COOH, wherein at least one n is an integer from 1 to 2, and at least one n is 0 or an integer from 1 to 2, m is 0 or 1 to provide a cyclopentyl ring or cyclohexyl ring, and R 1 is a C1-C75 alkyl group, the reactants further comprising a difunctional reactant selected from (a) H 2 N—R 2 —NH 2 where R 2 is selected (i) from a polyether group having a plurality of —OR 3 — groups where R 3 is a C3-C10 aliphatic hydrocarbyl, and (ii) a C2-C36 hydrocarbyl group and (b) HOOC—R 4 —COOH where R 4 is a C2-C34 hydrocarbyl group, where the composition has a melt viscosity at 130° C. of less than 100 cPs.
2. The process of claim 1 wherein the diamine of structure (IV) is 1,2-diaminocyclohexane.
3. The process of claim 1 wherein the reactants comprise HOOC—R 4 —COOH, which represents dimer acid.
4. The process of claim 1 wherein the reactants comprise H 2 N—R 2 —NH 2 where R 2 is a polyether group having a plurality of —OR 3 — groups where R 3 is a C2-C3 aliphatic hydrocarbyl.
5. The process of claim 4 wherein the difunctional reactant of formula H 2 N—R 2 —NH 2 has a formula weight of less than 3,000 g/mol.
6. The process of claim 1 wherein the reactants comprise H 2 N—R 2 —NH 2 where R 2 is a C2-C36 hydrocarbyl group.
7. The process of claim 6 wherein the reactants comprise H 2 N—R 2 —NH 2 and H 2 N—R 2 —NH 2 represents a second cyclic diamine of structure (IV)
wherein n is 0 or an integer from 1 to 2, m is 0 or 1 to provide a cyclopentyl ring or cyclohexyl ring.
8. The process of claim 1 wherein the reactants comprise both a difunctional reactant of formula H 2 N—R 2 —NH 2 where R 2 is selected (i) from a polyether group having a plurality of —OR 3 — groups where R 3 is a C2-C10 aliphatic hydrocarbyl, and (ii) a C2-C36 hydrocarbyl group, and a difunctional reactant of formula HOOC—R 4 —COOH where R 4 is a C2-C34 hydrocarbyl group.
9. The process of claim 8 wherein the difunctional reactant of formula H 2 N—R 2 —NH 2 represents a second cyclic diamine of structure (IV)
10. The process of claim 9 wherein the difunctional reactant of formula HOOC—R 4 —COOH represents dimer acid.
11. The process of claim 1 wherein the difunctional reactant comprises carboxylic acid groups, and carboxylic acid groups from the difunctional reactant constitute less than 25 equivalent percent of the total of the carboxylic acid groups present in the reactants.
12. The process of claim 1 wherein the difunctional reactant comprises amine groups, and the amine groups from the difunctional reactant constitute less than 25 equivalent percent of the total of the amine groups present in the reactants.
13. The process of claim 1 having a clarity that is greater than the corresponding composition prepared without the difunctional reactant(s).
14. A process of making a cyclic bisamide of structure (I)
comprising reacting under amidification conditions reactants comprising a diamine of structure (IV)
and a monocarboxylic acid of the formula R 1 —COOH, wherein n is 0 or an integer from 1 to 2, m is 0 or 1 to provide a cyclopentyl ring or cyclohexyl ring, and R 1 is selected from the group consisting of C1-C10 and C15-C30 alkyl groups, the reactants further comprising a difunctional reactant selected from (a) H 2 N—R 2 —NH 2 where R 2 is selected (i) from a polyether group having a plurality of —OR 3 — groups where R 3 is a C3-C10 aliphatic hydrocarbyl, and (ii) a C2-C36 hydrocarbyl group and (b) HOOC—R 4 —COOH where R 4 is a C2-C34 hydrocarbyl group, where the composition has a melt viscosity at 130° C. of less than 100 cPs.
15. The process of claim 14 wherein the diamine of structure (IV) is 1,2-diaminocyclohexane.
16. The process of claim 14 wherein the reactants comprise HOOC—R 4 —COOH, which represents dimer acid.
17. The process of claim 14 wherein the reactants comprise H 2 N—R 2 —NH 2 where R 2 is a polyether group having a plurality of —OR 3 — groups where R 3 is a C2-C3 aliphatic hydrocarbyl.
18. The process of claim 17 wherein the difunctional reactant of formula H 2 N—R 2 —NH 2 has a formula weight of less than 3,000 g/mol.
19. The process of claim 14 wherein the reactants comprise H 2 N—R 2 —NH 2 where R 2 is a C2-C36 hydrocarbyl group.
20. The process of claim 19 wherein the reactants comprise H 2 N—R 2 —NH 2 and H 2 N—R 2 —NH 2 represents a second cyclic diamine of structure (IV)
wherein n is 0 or an integer from 1 to 2, m is 0 or 1 to provide a cyclopentyl ring or cyclohexyl ring.
21. The process of claim 14 wherein the reactants comprise both a difunctional reactant of formula H 2 N—R 2 —NH 2 where R 2 is selected (i) from a polyether group having a plurality of —OR 3 — groups where R 3 is a C2-C10 aliphatic hydrocarbyl, and (ii) a C2-C36 hydrocarbyl group, and a difunctional reactant of formula HOOC—R 4 —COOH where R 4 is a C2-C34 hydrocarbyl group.
22. The process of claim 21 wherein the difunctional reactant of formula H 2 N—R 2 —NH 2 represents a second cyclic diamine of structure (IV)
23. The process of claim 22 wherein the difunctional reactant of formula HOOC—R 4 —COOH represents dimer acid.
24. The process of claim 14 wherein the difunctional reactant comprises carboxylic acid groups, and carboxylic acid groups from the difunctional reactant constitute less than 25 equivalent percent of the total of the carboxylic acid groups present in the reactants.
25. The process of claim 14 wherein the difunctional reactant comprises amine groups, and the amine groups from the difunctional reactant constitute less than 25 equivalent percent of the total of the amine groups present in the reactants.
26. The process of claim 14 having a clarity that is greater than the corresponding composition prepared without the difunctional reactant(s).
27. A process of making a cyclic bisamide of structure (II)
comprising reacting under amidification conditions reactants comprising a diamine of structure (IV)
and a monocarboxylic acid of the formula R 1 —COOH, wherein n is 0 or an integer from 1 to 2, m is 0 to provide a cyclopentyl ring, and R 1 is a C1-C75 alkyl group, the reactants further comprising a difunctional reactant selected from (a) H 2 N—R 2 —NH 2 where R 2 is selected (i) from a polyether group having a plurality of —OR 3 — groups where R 3 is a C3-C10 aliphatic hydrocarbyl, and (ii) a C2-C36 hydrocarbyl group and (b) HOOC—R 4 —COOH where R 4 is a C2-C34 hydrocarbyl group, where the composition has a melt viscosity at 130° C. of less than 100 cPs.
28. The process of claim 27 wherein the diamine of structure (IV) is 1,2-diaminocyclopentane.
29. The process of claim 27 wherein the reactants comprise HOOC—R 4 —COOH, which represents dimer acid.
30. The process of claim 27 wherein the reactants comprise H 2 N—R 2 —NH 2 where R 2 is a polyether group having a plurality of —OR 3 — groups where R 3 is a C2-C3 aliphatic hydrocarbyl.
31. The process of claim 30 wherein the difunctional reactant of formula H 2 N—R 2 —NH 2 has a formula weight of less than 3,000 g/mol.
32. The process of claim 27 wherein the reactants comprise H 2 N—R 2 —NH 2 where R 2 is a C2-C36 hydrocarbyl group.
33. The process of claim 32 wherein the reactants comprise H 2 N—R 2 —NH 2 and H 2 N—R 2 —NH 2 represents a second cyclic diamine of structure (IV)
wherein n is 0 or an integer from 1 to 2, m is 0 or 1 to provide a cyclopentyl ring or cyclohexyl ring.
34. The process of claim 27 wherein the reactants comprise both a difunctional reactant of formula H 2 N—R 2 —NH 2 where R 2 is selected (i) from a polyether group having a plurality of —OR 3 — groups where R 3 is a C2-C10 aliphatic hydrocarbyl, and (ii) a C2-C36 hydrocarbyl group, and a difunctional reactant of formula HOOC—R 4 —COOH where R 4 is a C2-C34 hydrocarbyl group.
35. The process of claim 34 wherein the difunctional reactant of formula H 2 N—R 2 —NH 2 represents a second cyclic diamine of structure (IV)
36. The process of claim 35 wherein the difunctional reactant of formula HOOC—R 4 .COOH represents dimer acid.
37. The process of claim 27 wherein the difunctional reactant comprises carboxylic acid groups, and carboxylic acid groups from the difunctional reactant constitute less than 25 equivalent percent of the total of the carboxylic acid groups present in the reactants.
38. The process of claim 27 wherein the difunctional reactant comprises amine groups, and the amine groups from the difunctional reactant constitute less than 25 equivalent percent of the total of the amine groups present in the reactants.
39. The process of claim 27 having a clarity that is greater than the corresponding composition prepared without the difunctional reactant(s).
40. A process of making a cyclic bisamide of structure (I)
comprising reacting under amidification conditions reactants comprising diamine of structure (IV)
and a monocarboxylic acid of the formula R 1 —COOH, wherein n is 0 or an integer from 1 to 2, m is 0 or 1 to provide a cyclopentyl ring or cyclohexyl ring, and R 1 is a C1-C75 alkyl group, the reactants further comprising a difunctional reactant selected from (a) H 2 N—R 2 —NH 2 where R 2 is selected (i) from a polyether group having a plurality of —OR 3 — groups where R 3 is a C3-C10 aliphatic hydrocarbyl, and (ii) a C2-C36 hydrocarbyl group and (b) HOOC—R 4 —COOH where R 4 is a C2-C34 hydrocarbyl group, where the composition has a melt viscosity at 130° C. of less than 100 cPs; and wherein the diamine of structure (IV) is a 1,3 diamine when m is 0, and a 1,3 or 1,4 diamine when m is 1.
41. The process of claim 40 wherein the diamine of structure (IV) is 1,3-diaminocyclohexane.
42. The process of claim 40 wherein the reactants comprise HOOC—R 4 —COOH, which represents dimer acid.
43. The process of claim 40 wherein the reactants comprise H 2 N—R 2 —NH 2 where R 2 is a polyether group having a plurality of —OR 3 — groups where R 3 is a C2-C3 aliphatic hydrocarbyl.
44. The process of claim 43 wherein the difunctional reactant of formula H 2 N—R 2 —NH 2 has a formula weight of less than 3,000 g/mol.
45. The process of claim 40 wherein the reactants comprise H 2 N—R 2 —NH 2 where R 2 is a C2-C36 hydrocarbyl group.
46. The process of claim 45 wherein the reactants comprise H 2 N—R 2 —NH 2 , and H 2 N—R 2 —NH 2 represents a second cyclic diamine of structure (IV)
wherein n is 0 or an integer from 1 to 2, m is 0 or 1 to provide a cyclopenty 1 ring or cyclohexy 1 ring.
47. The process of claim 40 wherein the reactants comprise both a difunctional reactant of formula H 2 N—R 2 —NH 2 where R 2 is selected (i) from a polyether group having a plurality of —OR 3 — groups where R 3 is a C2-C10 aliphatic hydrocarbyl, and (ii) a C2-C36 hydrocarbyl group, and a difunctional reactant of formula HOOC—R 4 —COOH where R 4 is a C2-C34 hydrocarbyl group.
48. The process of claim 47 wherein the difunctional reactant of formula H 2 N—R 2 —NH 2 represents a second cyclic diamine of structure (IV)
49. The process of claim 48 wherein the difunctional reactant of formula HOOC—R 4 —COOH represents dimer acid.
50. The process of claim 40 wherein the difunctional reactant comprises carboxylic acid groups, and carboxylic acid groups from the difunctional reactant constitute less than 25 equivalent percent of the total of the carboxylic acid groups present in the reactants.
51. The process of claim 40 wherein the difunctional reactant comprises amine groups, and the amine groups from the difunctional reactant constitute less than 25 equivalent percent of the total of the amine groups present in the reactants.
52. The process of claim 40 having a clarity that is greater than the corresponding composition prepared without the difunctional reactant(s).