Method and composition for textile printing

• US 6,291,023 B1
• Filed: 03/31/1999
• Issued: 09/18/2001
• Est. Priority Date: 04/22/1998
• Status: Expired due to Fees

• Current Assignee: SRI International, Inc.
• Original Assignee: SRI International, Inc.
• Inventors: Nigam, Asutosh
• Primary Examiner(s): CAMERON, ERMA C
• Application Number:
  US09/282,753
• Time in Patent Office: 902 Days
• Field of Search: 427/389.9, 427/412
• US Class Current: 427/389.9
• CPC Class Codes: B41M 5/508 Supports
• CPC Class Codes: B41M 5/52 Macromolecular coatings
• CPC Class Codes: B41M 5/5227 characterised by organic non-macromolecular additives, e.g. UV-absorbers, plasticisers, surfactants
• CPC Class Codes: B41M 5/5236 characterised by the use of natural gums, of proteins, e.g. gelatins, or of macromolecular carbohydrates, e.g. cellulose
• CPC Class Codes: B41M 5/5245 characterised by the use of polymers containing cationic or anionic groups, e.g. mordants
• CPC Class Codes: B41M 5/5254 characterised by the use of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
• CPC Class Codes: C08G 73/00 Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00 polycarbodiimides prepared from isocyanates C08G18/025, C08G18/797
• CPC Class Codes: C08G 73/06 Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
• CPC Class Codes: D06P 1/5242 Polymers of unsaturated N-containing compounds
• CPC Class Codes: D06P 1/5264 Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
• CPC Class Codes: D06P 1/5278 Polyamides; Polyimides; Polylactames; Polyalkyleneimines
• CPC Class Codes: D06P 1/5285 Polyurethanes; Polyurea; Polyguanides
• CPC Class Codes: D06P 5/001 Special chemical aspects of printing textile materials
• CPC Class Codes: D06P 5/30 Ink jet printing
• CPC Class Codes: D21H 17/54 obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
• CPC Class Codes: D21H 19/62 Macromolecular organic compounds or oligomers thereof obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: D21H 21/16 Sizing or water-repelling agents
• CPC Class Codes: Y10T 442/2246 Nitrogen containing

Abstract

The present invention features novel methods and compositions for coating textile substrates, wherein the coating compositions are composed of a coating agent selected from one of (a) an azetidinium polymer, (b) a guanidine polymer, (c) a mixture of an azetidinium polymer and a guanidine polymer, and (d) a copolymer of an azetidinium monomer and a guanidine monomer. Textile substrates coated with the compositions provide high quality printed images when printed with an ink containing a reactive dye having ionizable and/or nucleophilic groups capable of reacting with the coating agent in the textile coating composition. Images printed on a textile substrate coated with a coating composition of the invention are bleed-resistant, water-resistant (e.g., water-fast), detergent-resistant (e.g., detergent-fast), and/or are characterized by an enhanced chroma and hue.

Claims

1. A process for producing a treated textile substrate, comprising the step of applying to the surface of a textile substrate a coating composition containing a coating agent selected from the group consisting of (a) a mixture of an azetidinium polymer and a guanidine polymer, (b) a copolymer of an azetidinium monomer and a guanidine monomer, and (c) a poly(aminoamide)-epichlorohydrin resin.

2. The process of claim 1, wherein the coating agent comprises a mixture of an azetidinium polymer and a guanidine polymer.

3. The process of claim 2, wherein the azetidinium polymer is comprised of monomer units having the structural fornulla

in which R¹ and R² are independently C_1-6 alkylene, X⁻

is an anionic, organic or inorganic counterion, and Y¹, Y² and Y³ are selected from the group consisting of hydrogen, hydroxyl, halo, alkoxy, alkyl, amino, carboxy, acetoxy, cyano, and suilfhydryl.

4. The process of claim 3, wherein the guanidine polymer is comprised of monomer units having the structural formula

wherein R³ is hydrogen or C_1-6 alkyl and R⁴ is hydrogen, alkyl, alkoxy, or hydroxyl-substituted alkoxy.

5. The process of claim 4, wherein, in the guanidine polymer, R³ and R⁴ are hydrogen.

6. The process of claim 3, wherein the guanidine polymer is comprised of monomer units having the structural formula

wherein n is an integer in the range of 1 to 10 inclusive, R³ is hydrogen or C_1-6 alkyl and R⁴ is hydrogen, alkyl, alkoxy, or hydroxyl-substituted alkoxy.

7. The process of claim 6, wherein, in the guanidine polymer, R³ and R⁴ are hydrogen.

8. The process of claim 3, wherein, in the azetidinium polymer, R¹ and R² are methylene, X⁻

is selected from the group consisting of halide, acetate, methane sulfonate, succinate, citrate, malonate, fumarate, oxalate, and hydrogen sulfate, Y¹ and Y³ are independently hydrogen or C_1-6 alkyl, and Y² is hydrogen or hydroxyl.

9. The process of claim 8, wherein the guanidine polymer is comprised of monomer units having the structural formula

wherein R³ is hydrogen or C_1-6 alkyl and R⁴ is hydrogen, alkyl, alkoxy, or hydroxyl-substituted alkoxy.

10. The process of claim 9, wherein, in the guanidine polymer, R³ and R⁴ are hydrogen.

11. The process of claim 8, wherein the guanidine polymer is comprised of monomer units having the structural formula

wherein n is an integer in the range of 1 to 10 inclusive, R³ is hydrogen or C_1-6 alkyl and R⁴ is hydrogen, alkyl, alkoxy, or hydroxyl-substituted alkoxy.

12. The process of claim 11, wherein, in the guanidine polymer, R³ and R⁴ are hydrogen.

13. The process of claim 8, wherein, in the azetidinium polymer, Y¹ and Y³ are hydrogen and Y² is hydroxyl.

14. The process of claim 13, wherein the guanidine polymer is comprised of monomer units having the structural formula

wherein R³ is hydrogen or C_1-6 alkyl and R⁴ is hydrogen, alkyl, alkoxy, or hydroxyl-substituted alkoxy.

15. The process of claim 14, wherein, in the guanidine polymer, R³ and R⁴ are hydrogen.

16. The process of claim 13, wherein the guanidine polymer is comprised of monomer units having the structural formula

wherein n is an integer in the range of 1 to 10 inclusive, R³ is hydrogen or C_1-6 alkyl and R⁴ is hydrogen, alkyl, alkoxy, or hydroxyl-substituted alkoxy.

17. The process of claim 16, wherein, in the guanidine polymer, R³ and R⁴ are hydrogen.

18. The process of claim 1, wherein the coating agent is comprised of a copolymer of an azetidinium monomer unit and a guanidine monomer unit.

19. The process of claim 18, wherein the azetidinium monomer unit has the structural formula

in which R¹ and R² are independently C_1-6 alkylene, X⁻

is an anionic, organic or inorganic counterion, and Y¹, Y², and Y³ are selected from the group consisting of hydrogen, hydroxyl, halo, alkoxy, alkyl, amino, carboxy, acetoxy, cyano, and sulfhydryl, and the guanidine monomer unit has the structural formula

wherein n is an integer in the range of 1 to 10 inclusive, R³ is hydrogen or C_1-6 alkyl and R⁴ is hydrogen, alkyl, alkoxy, or hydroxyl-substituted alkoxy.

20. The process of claim 19, wherein, in the azetidinium monomer unit, R¹ and R² are methylene, X⁻

is selected from the group consisting of halide, acetate, methane sulfonate, succinate, citrate, malonate, fumarate, oxalate, and hydrogen sulfate, Y¹ and Y³ are independently hydrogen or C_1-6 alkyl, and Y² is hydrogen or hydroxyl.

21. The process of claim 1, wherein the coating composition is aqueous.

22. The process of claim 1, wherein the coating composition further comprises a colorant.

23. The process of claim 22, wherein the colorant is a pigment.

24. The process of claim 23, wherein the pigment is selected from the group consisting of silica, titanium dioxide and calcium carbonate.

25. The process of claim 22, wherein the colorant is a dye.

26. The process of claim 1, wherein the coating composition is applied in an amount that results in a coating representing approximately 0.5 wt. % to 20 wt. % of the textile substrate after drying.

27. The process of claim 1, wherein the coating agent represents approximately 1 wt. % to 100 wt. % of the coating composition, based upon total solids weight of the coating composition after drying.

28. A textile substrate treated by the process of claim 1.

29. A textile substrate treated by the process of claim 2.

30. A textile substrate treated by the process of claim 18.

34. The process of claim 1, wherein the coating agent is a poly(aminoamide)-epichlorohydrin resin.

36. The process of claim 1, further including, prior to application of the coating composition, pretreating the substrate with a pretreatment agent.

37. The process of claim 36, wherein the pretreatment agent is a resin.

38. The process of claim 36, wherein the pretreatment agent is a sizing agent.

31. A method for providing a water-resistant printed image on a textile substrate, comprising:

applying to a textile substrate a coating composition comprised of a coating agent selected from the group consisting of (a) a mixture of an azetidinium polymer and a guanidine polymer, (b) a copolymer of an azetidinium monomer and a guanidine monomer, and (c) a poly(aminoamide)-epichlorolhydrin resin, thereby producing a treated textile substrate; and

applying a colorant composition to the treated textile substrate, wherein the colorant composition contains a coating agent reactive colorant having ionizable and/or nucleophilic groups.

32. A printed textile product prepared by the method of claim 31.

33. The printed textile product of claim 32, wherein the printed image is water-resistant and detergent-resistant.

35. The method of claim 31, wherein the coating agent is a poly(aminoamide)-epichlorohydrin resin.

39. The process of claim 31, further including, prior to application of the coating composition, pretreating the substrate with a pretreatment agent.

40. The process of claim 39, wherein the pretreatment agent is a resin.

41. The process of claim 39, wherein the pretreatment agent is a sizing agent.