Phase change solid imaging material

• US 6,133,353 A
• Filed: 11/11/1999
• Issued: 10/17/2000
• Est. Priority Date: 11/11/1999
• Status: Expired due to Fees

• Current Assignee: 3D Systems, Inc. (3D Systems Corporation)
• Original Assignee: 3D Systems, Inc. (3D Systems Corporation)
• Inventors: Nguyen, My T., Bui, Loc V.
• Primary Examiner(s): Szekely, Peter A.
• Application Number:
  US09/439,263
• Time in Patent Office: 341 Days
• Field of Search: 523/160, 523/161, 524/198, 524/270, 524/272, 524/311, 524/312, 524/230, 524/487, 524/507
• US Class Current: 524/198
• CPC Class Codes: C08G 18/2825 having at least 6 carbon atoms
• CPC Class Codes: C08G 18/3821 Carboxylic acids; Esters thereof with monohydroxyl compounds
• CPC Class Codes: C08G 18/71 Monoisocyanates or monoisothiocyanates
• CPC Class Codes: C08G 69/34 using polymerised unsaturated fatty acids
• CPC Class Codes: C08K 5/0008 Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• CPC Class Codes: C08K 5/205 Compounds containing groups, e.g. carbamates
• CPC Class Codes: C08K 5/29 Compounds containing one or more carbon-to-nitrogen double bonds
• CPC Class Codes: C08L 77/00 Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 11/34 Hot-melt inks

Abstract

A solubilizing agent and a compound made by reacting selected nucleophiles, including fatty acid reactants and amines with an isocyanate are disclosed. The addition of the isocyanate and the different nucleophiles will create a di-urethane tetra-amide solubilizing agent product. The polyamide-solubilizing agent is useful as an ingredient in a phase change solid imaging material and as carrier compositions used to make phase change ink jet inks.

Claims

1. A formulation for use in jetting from a print head comprising:

(a) a viscosity modifying agent;

(b) a tackifier;

(c) a polyamide resin; and

(d) a solubilizing agent for the polyamide resin, the agent being selected from the group consisting of monourethane monoamide a diurethane monoamide, a diurethane tri-amide, a diurethane tetra-amide and combinations thereof.

2. A formulation according to claim 1 wherein the viscosity modifying agent is selected from the group consisting of a urethane wax, an amide wax, alkyl wax and combinations thereof.

3. The formulation according to claims 2 wherein the urethane wax is a linear alkyl carbamate.

4. The formulation according to claim 3 wherein the linear alkyl carbamate is selected from the group consisting of octadecyl octadecyl carbamate;

dodecyl octadecyl carbamate;

hexadecyl octadecyl carbamate; and

hexyl octadecyl carbamate.

5. The formulation according to claim 1 wherein the tackifier is selected from the group consisting of a rosin carbamate, a rosin ester, glycerin rosin ester, hydrogenated pentaerythritol ester, hydrogenated glycerin ester, modified tall oil rosin, a polymerized rosin, an aromatic hydrocarbon rosin, an aliphatic hydrocarbon rosin.

6. The formulation according to claim 1 wherein the tackifier is a rosin carbamate tackifier selected from the group consisting of butyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenantbrenyl)methoxy]carbonyl}amino)-1 4,4-trimethylcyclohexyl]methyl carbamate;

hexyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy)carbonyl}amino)-14,4-trimethylcyclohexyl]methyl carbamate;

octyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy]carbonyl}amino)-1,4,4-trimethylcyclohexyl]methyl] carbamate;

dodecyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy]carbonyl}amino)-1,4,4-trimethylcyclohexyl]methyl carbamate; and

octadecyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy]carbonyl}amino)-1,4,4-trimethylcyclohexyl]methy) carbamate.

7. The formulation according to claim 1 wherein the solubilizing agent is the reaction product of a fatty acid, an amine, and an isocyanate.

8. The formulation according to claim 7 wherein the fatty acid is selected from the group consisting of a fatty acid, a hydroxy fatty acid, and combinations thereof.

9. The formulation according to claim 7 wherein the reaction product further includes an alcohol as an additional reactant.

10. The formulation according to claim 7 wherein the isocyanate is selected from the group consisting of a monoisocyanate, a diisocyanate, a triisocyanate, a copolymer of a diisocyanate and a copolymer of a triisocyanate and combinations thereof.

11. The formulation according to claim 10 wherein the isocyanate is a diisocyanate selected from the group consisting of 1,6-dicyanatohexane, isophorone diisocyanate, and 4,4'"'"'-methylene bis(phenylisocyanate).

12. The formulation according to claim 7 wherein the amine is a diamine.

13. The formulation according to claim 12 wherein the diamine is selected from the group consisting of ethylenediamine, 1,3-propylenediamine;

2-butyl-2 ethyl-1.5-pentylenediamine; and

1,2-diaminocyclohexane.

14. The formulation according to claim 7 wherein the amine is a monoamine.

15. The formulation according to claim 14 above wherein the monoamine is 2-hydroxy ethylamine.

16. The formulation according to claim 7 wherein the fatty acid reactant is selected from the group consisting of stearic acid, decanoic acid, myristic acid, and docasanic acid.

17. The formulation according to claim 2 wherein the urethane wax is the reaction product of a monohydric alcohol and amono-isocyanate.

18. The formulation according to claim 17 wherein the monohydric alcohol is selected from the group consisting of an aliphatic alcohol, an aliphatic/aromatic alcohol, an aromatic alcohol, and a fused ring alcohol and combinations thereof.

19. A solid imaging material for use in three-dimensional model rapid prototyping comprising:

(a) a viscosity modifying agent;

(b) a tackifier;

(c) a polyamide resin; and

(d) a solubilizing agent for the polyamide resin, the agent being a diurethane tetra-amide.

20. The material according to claim 19 wherein the viscosity modifying agent is a urethane wax.

21. The compound according to claim 20 wherein the urethane is a linear alkyl urethane wax.

22. The compound according to claim 21 wherein the linear alkyl urethane is selected from the group consisting of octadecyl, octadecyl carbamate;

dodecyl octadecyl carbamate;

hexadecyl octadecyl carbamate; and

hexyl octadecyl carbamate.

23. The compound according to claim 19 wherein the tackifier is a rosin urethane wax.

24. The compound according to claim 19 wherein the tackifier is selected from the group consisting of butyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy]carbonyl}amino)-1,4,4-trimethylcyclohexyl]methyl carbamate;

hexyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy]carbonyl}amino)-1,4,4-trimethylcyclohexyl]methyl carbamate;

octyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy]carbonyl}amino)-1,4,4-trimethylcyclohexyl]methyl carbamate;

dodecyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy]carbonyl}amino)-1,4,4-trimethylcyclohexyl]methyl carbamate; and

octadecyl [3-({[(7-isopropyl-1,4a-dimethyltetradecahydro-1-phenanthrenyl)methoxy]carbonyl}amino)-1,4,4-trimethylcyclohexyl]methyl carbamate.

25. The compound according to claim 19 wherein the diurethane tetra-amide is the reaction product of a fatty acid reactant, an amine, and an isocyanate.

26. The reaction product according to claim 25 wherein the isocyanate is selected from the group consisting of a monoisocyanate, a diisocyanate, a triisocyanate, a copolymer of a triisocyanate and a copolymer of a triisocyanate and combinations thereof.

27. The material according to claim 19 wherein the isocyanate is a diisocyanate selected from the group consisting of 1,6-dicyanatohexane, isophorone diisocyanate, and 4,4'"'"'-methylene bis(phenylisocyanate).

28. The material according to claim 19 wherein the amine is a diamine.

29. The material according to claim 28 wherein the diamine is selected from the group consisting of ethylenediamine, 1,3-propylenediamine;

and 2-butyl-2-ethyl-1,5-pentylenediamine.

30. The material according to claim 25 wherein the fatty acid reactant is selected from the group consisting of stearic acid, decanoic acid, myristic acid, and docasanic acid.

31. The material according to claim 20 wherein the urethane wax is the reaction product of a monohydric alcohol and a mono-isocyanate.

32. The formulation according to claim 31 wherein the monohydric alcohol is selected from the group consisting of an aliphatic alcohol, an aliphatic/aromatic alcohol, an aromatic alcohol, and a fused ring alcohol and combinations thereof.