IP Library Granted Patent US 9,821,589
Granted Patent B2
US 9,821,589 · App. 14/779,419 · Granted Nov 21, 2017

Coating compositions for forming toner receptive coatings

Inventors: David K. Hood (Basking Ridge, NJ); Charles J. Wasserman (Waukesha, WI); Karyn B. Visscher (Morris Plains, NJ); Sounak Sarkar (Lodi, NJ)
Assignee: ISP INVESTMENTS LLC
B41M5/5254C08F218/08C08F226/06C08F226/08C08F226/10C09D139/04C09D139/06C08F2220/283
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Quick Facts
Patent No.
US 9,821,589
App. No.
14/779,419
Granted
Nov 21, 2017
Kind
B2
Abstract

The present invention provides coating composition for forming a toner receptive coating on a substrate containing a polymer comprising: (a) a N-vinyl amide monomer, (b) a vinyl acetate monomer, (c) a substituted or unsubstituted monomer comprising a cyclic ether, and (d) a solvent. The coating compositions may further comprise a (e) non-reactive hydrophobic monomer. The invention also provides substrates coated with the toner receptive coatings.

Claims (29)

1. A toner receptive coating composition on a substrate containing a polymer comprising: (a) a N-vinyl amide monomer, (b) a vinyl acetate monomer, (c) a reactive monomer comprising an acetoacetate moiety, and (d) a solvent.

2. The coating composition according to claim 1 , wherein (a) the N-vinyl amide monomer is selected from the group consisting of N-vinyl pyrrolidone, N-vinyl valerolactam, N-vinyl caprolactam, hydroxyethylpyrrolidone methacrylate, and N-vinyl formamide.

3. The coating composition according to claim 1 , wherein (a) and (b) are N-vinyl pyrrolidone-co-vinyl acetate or n-vinyl caprolactam-co-vinyl acetate.

4. The coating composition according to claim 3 , wherein (a) and (b) are N-vinyl pyrrolidone-co-vinyl acetate.

5. The coating composition according to claim 1 , wherein the monomer in (c) the reactive monomer comprising an acetoacetate moiety is selected from the group consisting of amide, alkyl, carboxyl, carbonyl, and ether groups.

6. The coating composition according to claim 5 , wherein (c) the reactive monomer comprising an acetoacetate moiety is selected from the group consisting of acetoacetoxyethyl methacrylate, acetoacetoxyethyl acrylate, and allyl acetoacetate.

7. The coating composition according to claim 1 , wherein (a) is 0.1-80%, (b) is 1-80%, (c) is 1-80%, and (d) is to 100%, by weight.

8. A toner receptive coating composition on a substrate containing a polymer comprising: (a) a N-vinyl amide monomer, (b) a vinyl acetate monomer, (c) a reactive monomer comprising an acetoacetate moiety, and (d) a solvent; wherein the composition has a solids content of about 15-50% and a viscosity of about 200-3000 cps.

9. The coating composition according to claim 1 , wherein the polymer comprising: (a) a N-vinyl amide monomer, (b) a vinyl acetate monomer, (c) a reactive monomer comprising an acetoacetate moiety, and (d) a solvent is selected from the group consisting of vinyl pyrrolidone/vinyl acetate/acetoacetoxyethyl methacrylate, vinyl caprolactam/vinyl acetate/acetoacetoxyethyl methacrylate, vinyl pyrrolidone/vinyl acetate/allyl acetoacetate, and vinyl caprolactam/vinyl acetate/allyl acetoacetate.

10. The coating composition according to claim 1 , further comprising (e) a non-reactive hydrophobic monomer.

11. The coating composition according to claim 10 , wherein (e) the non-reactive hydrophobic monomer comprises a non-reactive C 1 -C 20 alkyl acrylate monomer.

12. The coating composition according to claim 11 , wherein (e) the non-reactive C 1 -C 20 alkyl acrylate monomer is selected from the group consisting of stearyl acrylate, butyl acrylate, octyl acrylate, decyl acrylate, and lauryl (meth)acrylate.

13. A toner receptive coating composition on a substrate containing a polymer comprising: (a) a N-vinyl amide monomer, (b) a vinyl acetate monomer, (c) a reactive monomer comprising an acetoacetate moiety, and (d) a solvent; further comprising (f) a binder, (g) a pigment, and (h) a surfactant.

14. The coating composition according to claim 10 , wherein the polymer is selected from the group consisting of vinyl caprolactam/vinyl acetate/acetoacetoxyethyl methacrylate/stearyl acrylate and vinyl caprolactam/vinyl acetate/allyl acetoacetoacetate/stearyl acrylate.

15. The coating composition according to claim 1 , wherein the composition is in the form of an aqueous dispersion.

16. The coating composition according to claim 1 , wherein the polymer further comprises an additive selected from the group consisting of adhesives, aerosols, agricultural agents, anti-soil redeposition agents, batteries agents, beverages, biocides, block copolymers, branch/comb copolymers, cementing agents, cleaning agents, coating agents, conductive materials, cosmetic agents, cross-linkers, dental agents, decorated pigments, detergents, dispersants, drugs, electronics, encapsulations, foods, hair sprays, household-industrial-institutional, inks and coatings, interlaminate adhesives, lithographic solutions, membrane additive agents, metal working fluids, oilfield agents, paints, paper, paper sizing agents, personal care agents, pharmaceuticals, pigment additives, plasters, plastics, printing, reactive biocides, reactive rheology modifiers, refractive index modifiers, sequestrants, soil release agents, static control agents, and wood-care agents.

17. The coating composition according to claim 10 , wherein the polymer further comprises an additive selected from the group consisting of adhesives, aerosols, agricultural agents, anti-soil redeposition agents, batteries agents, beverages, biocides, block copolymers, branch/comb copolymers, cementing agents, cleaning agents, coating agents, conductive materials, cosmetic agents, cross-linkers, dental agents, decorated pigments, detergents, dispersants, drugs, electronics, encapsulations, foods, hair sprays, household-industrial-institutional, inks and coatings, interlaminate adhesives, lithographic solutions, membrane additive agents, metal working fluids, oilfield agents, paints, paper, paper sizing agents, personal care agents, pharmaceuticals, pigment additives, plasters, plastics, printing, reactive biocides, reactive rheology modifiers, refractive index modifiers, sequestrants, soil release agents, static control agents, and wood-care agents.

18. A toner substrate coated with a coating composition containing a polymer comprising: a polymer comprising: (a) a N-vinyl amide monomer, (b) a vinyl acetate monomer, (c) a reactive monomer comprising an acetoacetate moiety, and (d) a solvent.

19. The toner substrate coated with a coating composition according to claim 18 , further comprising (e) a non-reactive hydrophobic monomer.

20. A flexible food package substrate coated with a coating composition containing a polymer comprising: (a) a N-vinyl amide monomer, (b) a vinyl acetate monomer, (c) a reactive monomer comprising an acetoacetate moiety, and (d) a solvent.

21. A flexible food package substrate coated with a coating composition according to claim 20 , further comprising (e) a non-reactive hydrophobic monomer.

22. The coating composition according to claim 1 , wherein the polymer has the following structure:

23. The coating composition according to claim 1 , wherein the polymer has the following structure:

24. A toner receptive coating composition containing a polymer comprising: (a) a N-vinyl amide monomer, (b) a vinyl acetate monomer, (c) a reactive monomer comprising an acetoacetate moiety, and (d) a solvent.

25. The coating composition according to claim 24 , wherein (a) the N-vinyl amide monomer is selected from the group consisting of N-vinyl pyrrolidone, N-vinyl valerolactam, N-vinyl caprolactam, hydroxyethylpyrrolidone methacrylate, and N-vinyl formamide.

26. The coating composition according to claim 24 , wherein (a) and (b) are N-vinyl pyrrolidone-co-vinyl acetate or n-vinyl caprolactam-co-vinyl acetate.

27. The coating composition according to claim 26 , wherein (a) and (b) are N-vinyl pyrrolidone-co-vinyl acetate.

28. The coating composition according to claim 24 , wherein the monomer in (c) the reactive monomer comprising an acetoacetate moiety is selected from the group consisting of amide, alkyl, carboxyl, carbonyl, and ether groups.

29. The coating composition according to claim 24 , wherein the toner receptive coating composition is on a substrate.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Jan 10, 2020
From: THE BANK OF NOVA SCOTIA
To: AVOCA LLC; HERCULES LLC; ISP INVESTMENTS LLC; PHARMACHEM LABORATORIES LLC
Reel/Frame 051557/0504 →
SECURITY AGREEMENT Recorded Jul 3, 2017
From: AVOCA, INC.; HERCULES LLC; ISP INVESTMENTS LLC; PHARMACHEM LABORATORIES, INC.
To: THE BANK OF NOVA SCOTIA, AS ADMINISTRATIVE AGENT
Reel/Frame 043084/0753 →
CHANGE OF NAME Recorded May 24, 2017
From: ISP INVESTMENTS INC.
To: ISP INVESTMENTS LLC
Reel/Frame 042560/0842 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2015
From: HOOD, DAVID K.; WASSERMAN, CHARLES J.; VISSCHER, KARYN B.; SARKAR, SOUNAK
To: ISP INVESTMENTS INC.
Reel/Frame 036634/0625 →
Continuity (3)
Provisional Application 61805307 · Mar 26, 2013
Provisional Application 61827195 · May 24, 2013
Related Publication 20160059607A1 · Mar 3, 2016