Additive and vehicle for inks, paints, coatings and adhesives

• US 20060128831A1
• Filed: 12/10/2004
• Published: 06/15/2006
• Est. Priority Date: 12/10/2004
• Status: Active Grant

• Current Assignee: Omnitech Environmental, LLC
• Original Assignee: Omnitech Environmental, LLC
• Inventors: Skov, Richard T., Cook, Leroy John
• Granted Patent: US 7,863,485 B2
• Time in Patent Office: Days
• US Class Current: 523/160
• CPC Class Codes: C07C 211/00 Compounds containing amino groups bound to a carbon skeleton
• CPC Class Codes: C08F 8/00 Chemical modification by after-treatment graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C
• CPC Class Codes: C09J 133/04 Homopolymers or copolymers of esters C09J143/04 takes precedence

Abstract

An environmentally safe additive and vehicle system are provided for water-based and oil-based printing inks, paints, coatings and adhesives which can be rapidly transferred, dispersed, dispensed, spread, dried and cured. The low cost, stable additive and vehicle system enhance multiple color, high speed printing with sharp, highly defined images and superior quality, and can be used on many different types of substrates, such as paper, paperboard, cardboard, clay coated board, foil, plastic, glass, metal, wood and composites. The additive may be formed by the reaction product of a photoinitiator, such as an UV-activated polyelectrolyte, and a monomer, such as an acrylate or a methacrylate in an aqueous solution. In other embodiments, the additive is formed from a carboxylic acid or anhydride and alkylalkanolamine monomer or a dialkylaminoalkyl acrylate or methacrylate monomer in an aqueous solution.

Claims

1. An additive, comprising an aqueous solution of the reaction product of:

(i) a first reagent comprising at least one material selected from the group consisting of a carboxylic acid and an anhydride; and

(ii) a second reagent comprising at least one material selected from the group consisting of an alkyl alkanolamine monomer, a dialkylaminoalkyl acrylate monomer, and a dialkylaminoalkyl methacrylate monomer.

2. The additive of claim 1, wherein first reagent is selected from the group consisting of formic acid, acetic acid, benzoic acid, propionic acid, glycolic acid, oxalic acid, lactic acid, chloroacetic acid, fumaric acid, acrylic acid, methacrylic acid, itaconic acid, gluconic acid, acetylsalicylic acid, adipic acid, malonic acid, maleic acid, stearic acid, oleic acid, sebacic acid, succinic acid, citric acid, tartaric acid, abietic acid, palmitic acid, ricinoleic acid, protocatechuic acid, maleic anhydride, glutaric anhydride, 3,3′

4,4′

-benzophenone-tetracarboxylic acid;

4,4′

-carbonyldiphthalic acid;

benzophenonetetracarboxylic dianhydride;

orthobenzoylbenzoic acid, methanone benzoic acid, and succinic anhydride.

3. The additive of claim 1, wherein the second reagent is an alkyl alkanolamine monomer selected from the group consisting of N,N-diethylethanolamine, N,N-dimethylethanolamine, N-methyl-N-ethyl-ethanolamine, N-methyl-ethanolamine, and N-methyl-diethanolamine.

4. A material selected from the group consisting of a paint, an ink, and a coating, comprising the additive of claim 1, and further comprising at least one of a surfactant in an amount of about 0.05 to 0.5 weight percent, a defoamer in an amount of about 0.05 to 0.5 weight percent, and an inhibitor in an amount of about 0.05 to 2.0 weight percent.

5. An ink, paint or coating, or a vehicle for an ink, paint or coating, further comprising the additive of claim 1.

6. An additive comprising an aqueous solution of the reaction product of:

(i) a first reagent comprising at least one material selected from the group consisting of a carboxylic acid containing a benzene ring and an anhydride containing a benzene ring; and

(ii) a second reagent comprising at least one material selected from the group consisting of a dialkylaminoalkyl acrylate monomer and a dialkylaminoalkyl methacrylate monomer.

7. The additive of claim 6, wherein the first reagent is selected from the group consisting of benzoic acid;

4,4′

-bis(dimethylamino)benzophenone;

2,2′

4,6′

-tetrahydroxybenzophenone, isoeuxanthonic acid;

2,2′

,5,6′

-tetrahydroxybenzophenone;

euxanthonic acid;

benzenecarboxylic acid;

1,4-benzenedicarboxaldehyde;

terephthalaldehyde;

1,2-benzenedicarboxylic acid;

1,3-benzenedicarboxylic acid;

isophthalic acid;

1,4-benzenedicarboxylic acid;

terephthalic acid;

2-aminobenzeneboronic acid;

2-amino-1,3-benzenedicarboxylic acid;

1,3-benzenedicarboxylic acid;

4-bromo-1,3-benzenedicarboxylic acid;

2-chloro-1,3-benzenedicarboxylic acid;

4,6-dichloro-1,3 benzenedicarboxylic acid;

2,5-dichloro-1,3-benzenedicarboxylic acid;

4,5-dimethoxy-1,3 benzenedicarboxylic acid;

2-nitro-1,3-benzenedicarboxylic acid;

tetrabromo-1,3-benzenedicarboxylic acid;

benzenepentacarboxylic acid;

4,4′

-carbonylbis (1,2-benzene dicarboxylic acid);

3,3′

,4,4′

-tetracarboxybenzophenone;

3,3′

4,4′

-benzophenone-tetracarboxylic acid;

4,4′

-carbonyldiphthalic acid;

benzophenonetetracarboxylic dianhydride;

orthobenzoylbenzoic acid, and methanone benzoic acid.

8. The additive of claim 6, wherein the second reagent is selected from the group consisting of dialkylaminoalkyl acrylate or methacrylate monomer is selected from the group consisting of N,N-dimethylaminoethyl acrylate, N,N-dimethylaminoethyl methacrylate;

N,N-diethylaminoethyl acrylate, N,N-diethylaminopropyl acrylate, N,N-dimethylaminoethyl methacrylate, N,N-diethylaminoethyl methacrylate, N,N-diethylaminopropyl methacrylate, N,N-diethylaminopropyl acrylate;

N,N-diethylaminobutyl methacrylate; and

N,N-diethylaminobutyl acrylate.

9. The additive of claim 6, further comprising sufficient alcohol or amine to raise the pH of the additive to a pH in the range of about 7 to about 10.

10. An ink, paint or coating, or a vehicle for an ink, paint or coating, further comprising the additive of claim 6.

11. A method of forming an additive, the method comprising:

forming an aqueous solution of a first reagent or a second reagent; and

adding the other of the first reagent and the second reagent to the aqueous solution, wherein the first reagent comprises at least one material selected from the group consisting of a carboxylic acid and an anhydride, and the second reagent comprises at least one material selected from the group consisting of an alkylalkanolamine monomer, a dialkylaminoalkyl acrylate monomer, and a dialkylaminoalkyl methacrylate monomer, and wherein the first reagent and the second reagent react to form the additive.

12. The method of claim 11, wherein the first reagent is in stoichiometric proportion with the second reagent.

13. The method of claim 11, wherein the additive comprises about 40 to 85 weight percent water.

14. The method of claim 11, further comprising testing the pH of the additive, and if the pH is below about 8.5, adding an alcohol or an amine to adjust the pH of the additive to a level of from about 7 to about 10.

15. The method of claim 11, wherein the first reagent is selected from the group consisting of formic acid, acetic acid, propionic acid, glycolic acid, oxalic acid, lactic acid, chloroacetic acid, fumaric acid, acrylic acid, methacrylic acid, itaconic acid, gluconic acid, acetylsalicylic acid, adipic acid, malonic acid, maleic acid, stearic acid, oleic acid, sebacic acid, succinic acid, citric acid, tartaric acid, abietic acid, palmitic acid, ricinoleic acid, protocatechuic acid, maleic anhydride, glutaric anhydride, and succinic anhydride.

16. The method of claim 11, wherein the second reagent is selected from the group consisting of N,N-diethylethanolamine, N,N-dimethylethanol-amine, N-methyl-N-ethylethanolamine, N-methyl-ethanolamine, N-methyldiethanolamine, N,N-dimethylaminoethyl acrylate, N,N-dimethylaminoethyl methacrylate;

N,N-diethylaminoethyl acrylate, N,N-diethylaminopropyl acrylate, N,N-dimethylaminoethyl methacrylate, N,N-diethylaminoethyl methacrylate, N,N-diethylaminopropyl methacrylate, N,N-diethylaminopropyl acrylate;

N,N-diethylaminobutyl methacrylate; and

N,N-diethylaminobutyl acrylate.

17. The method of claim 11, wherein the additive comprises about 40 to 85 weight percent water.

18. A method of forming a vehicle, the method comprising:

a) adding the additive of claim 11 in an amount up to about 10 weight percent of the vehicle;

b) adding about 4-45% of a first component, the first component comprising at least one material selected from the group consisting of an acrylic resin solution, a latex resin solution, urethane resin solution, and a vegetable oil; and

c) adding about 50-90% of a second component, the second component comprising at least one material selected from the group consisting of fumaric resin solution and acrylic resin emulsion.

19. A method of forming an ink, a paint, a coating, or an adhesive, the method comprising:

a) providing about 4-45 weight percent of a first component, the first component comprising at least one material selected from the group consisting of an acrylic resin solution, a latex resin solution, urethane resin solution and a vegetable oil;

b) adding about 50-90 weight percent of a second component, the second component comprising at least one material selected from the group consisting of fumaric resin solution and acrylic resin emulsion;

c) adding about 0.5 to 10 weight percent of the additive of claim 11 to form a vehicle; and

d) mixing the vehicle with a formulation for an ink, a paint, a coating or an adhesive.

20. The method of claim 19, wherein the first component comprises acrylic resin solution, the second component comprises fumaric resin, and the weight ratio of fumaric resin to acrylic resin solution is from about 2:

1 to about 4;

1.

21. A method of forming an oil based ink or ink vehicle, the method comprising:

providing a refined vegetable oil; and

adding from about 1 to about 6 weight percent of the additive of claim 11.

22. A method of forming an oil based paint, the method comprising:

providing a refined vegetable oil; and

adding from about 5 to about 10 weight percent of the additive of claim 11.

23. A method of forming a water-based coating, the method comprising:

adding about 5 weight percent of the additive of claim 11;

adding about 10 weight percent high T_g acrylic resin;

adding about 40 weight percent high T_g acrylic emulsion;

adding about 30 weight percent low T_g acrylic emulsion; and

adding about 3 weight percent wax dispersion.

24. A method of forming an ink, paint, coating, or adhesive, or a vehicle suitable for an ink, paint, coating or adhesive, the method comprising:

adding the additive of claim 11 to a water-based resin solution or resin emulsion; and

mixing the additive and the solution with a formulation for an ink, a paint, a coating or an adhesive, or with a vehicle for an ink, a paint, a coating, or an adhesive.

25. A vehicle system, comprising by weight:

(a) about 4-45% of a first component, the first component comprising at least one material selected from the group consisting of an acrylic resin solution, a latex solution, a urethane solution, a microcrystalline wax solution, and a vegetable oil;

(b) about 50-90% of a second component, the second component comprising at least one material selected from the group consisting of a fumaric resin solution and an acrylic resin emulsion; and

(c) about 0.5-10% of an aqueous solution of an additive comprising the reaction product of

(i) a first reagent comprising at least one material selected from the group consisting of a carboxylic acid and an anhydride; and

(ii) a second reagent comprising at least one material selected from the group consisting of an alkyl alkanolamine monomer, a dialkylaminoalkyl acrylate monomer, and a dialkylaminoalkyl methacrylate monomer.

26. The vehicle system of claim 25, wherein the additive is capable of being activated by heat to cause phase separation of the vehicle system.

27. The vehicle system of claim 25, wherein the additive is capable of being cured photochemically.

28. The vehicle system of claim 25, wherein the first reagent is selected from the group consisting of formic acid, acetic acid, propionic acid, glycolic acid, oxalic acid, lactic acid, chloroacetic acid, dichlorophenoxyacetic acid, fumaric acid, acrylic acid, methacrylic acid, itaconic acid, gluconic acid, 2-hydroxy benzoic acid, acetylsalicylic acid, adipic acid, malonic acid, maleic acid, stearic acid, oleic acid, sebacic acid, succinic acid, citric acid, tartaric acid, abietic acid, naphthenic acid, palmitic acid, ricinoleic acid, protocatechuic acid, benzoic acid, hydroxybenzoic acid, cinnamic acid, hydroxycinnamic acid, caffeic acid, bile acid, maleic anhydride, glutaric anhydride, trimellitic anhydride, phthalic anhydride, succinic anhydride, 4,4′

bis(dimethylamino)-benzophenone;

2,2′

4,6′

-tetrahydroxybenzophenone, isoeuxanthonic acid;

2,2′

,5,6′

-tetrahydroxybenzophenone;

euxanthonic acid;

benzenecarboxylic acid;

1,4-benzenedicarboxaldehyde;

terephthalaldehyde;

1,2-benzenedicarboxylic acid;

1,3-benzenedicarboxylic acid;

isophthalic acid;

1,4-benzenedicarboxylic acid;

terephthalic acid;

2-aminobenzeneboronic acid;

2-amino-1,3-benzenedicarboxylic acid;

1,3-benzenedicarboxylic acid;

4-bromo-1,3-benzenedicarboxylic acid;

2-chloro-1,3-benzenedicarboxylic acid;

4,6-dichloro-1,3 benzenedicarboxylic acid;

2,5-dichloro-1,3-benzenedicarboxylic acid;

4,5-dimethoxy-1,3 benzenedicarboxylic acid;

2-nitro-1,3-benzenedicarboxylic acid;

tetrabromo-1,3-benzenedicarboxylic acid;

benzenepentacarboxylic acid;

4,4′

-carbonylbis (1,2-benzene dicarboxylic acid);

3,3′

,4,4′

-tetracarboxybenzophenone;

3,3′

4,4′

-benzophenone-tetracarboxylic acid;

4,4′

-carbonyldiphthalic acid;

benzophenonetetracarboxylic dianhydride;

orthobenzoylbenzoic acid, and methanone benzoic acid; and

the second reagent is an alkyl alkanolamine monomer selected from the group consisting of N,N-diethylethanolamine, N,N-dimethylethanolamine, N-methyl-N-ethyl-ethanolamine, N-methyl-ethanolamine, and N-methyl-diethanolamine.

29. The vehicle system of claim 25, wherein the first component comprises acrylic resin solution, the second component comprises fumaric resin, and the weight ratio of fumaric resin to acrylic resin solution is from about 2:

1 to about 4;

1.

30. The vehicle system of claim 25, wherein the first component comprises about 2-50% acrylic resin, water up to about 75%, and about 0-20% diluting agent.

31. The vehicle system of claim 30, wherein the diluting agent is selected from the group consisting of monoethanolamine, dimethanolamine, triethanolamine, ammonia, morpholine, propylene glycol, and polypropylene glycol.

32. The vehicle system of claim 25, wherein the second component comprises about 2-50% fumaric resin, water up to about 75%, and about 0-30% diluting agent.

33. The vehicle system of claim 25, wherein the first component comprises a urethane dispersion of about 25 percent to about 50 percent solids in an aqueous solution.

34. The vehicle system of claim 25, wherein the first component comprises a microcrystalline wax in an aqueous dispersion or emulsion.

35. The vehicle system of claim 25, wherein the first component is selected from the group consisting of corn oil, cottonseed oil, olive oil, palm oil, palm kernel oil, peanut oil, linseed oil, soybean oil, tall oil, and tung oil.

36. The vehicle system of claim 25, wherein the second component comprises about 50-100% acrylic emulsion resin and water up to about 30%.

37. A paint, ink, or coating comprising the vehicle system of claim 25.

38. A paint, ink, or coating comprising the vehicle system of claim 25, further comprising at least one of

i) a surfactant in an amount of about 0.05 to 0.5 weight percent;

ii) a defoamer in an amount of about 0.05 to 0.5 weight percent; and

iii) an inhibitor in an amount of about 0.05 to 2.0 weight percent.

39. A vehicle system, comprising by weight:

(a) about 4-45% of a first component comprising at least one material selected from the group consisting of an acrylic resin solution, a latex resin solution, a paraffin solution, a paraffin emulsion, a urethane resin solution, and a vegetable oil;

(b) about 50-90% of a second component comprising at least one material selected from the group consisting of a fumaric resin solution and an acrylic resin emulsion; and

(c) about 0.5-10% additive in aqueous solution comprising the reaction product of

(i) a first reagent comprising at least one material selected from the group consisting of a carboxylic acid containing a benzene ring and an anhydride containing a benzene ring; and

(ii) a second reagent comprising at least one material selected from the group consisting of an alkylaminoalkyl acrylate monomer and an alkylaminoalkyl methacrylate monomer.

40. The vehicle system of claim 39, wherein the second reagent is selected from the group consisting of N-methyl-ethanolamine, N,N-diethylethanolamine, N,N-dimethylethanolamine, N-methyl-N-ethyl-ethanolamine, and N-methyl-diethanolamine.

41. The vehicle system of claim 39, wherein the first component is selected from the group consisting of a urethane resin solution, a paraffin solution, a paraffin emulsion, and linseed oil.

42. An ink, coating, or adhesive made with the vehicle according to claim 39.

43. A vehicle system, comprising by weight:

(a) about 80-99% of a first component comprising at least one material selected from the group consisting of an acrylic resin solution, a urethane resin solution, a latex resin solution, a latex resin emulsion, a wax dispersion or emulsion, a fumaric resin solution, and a vegetable oil; and

(b) about 1-20% additive comprising in aqueous solution the reaction product of

(i) a first reagent comprising at least one material selected from the group consisting of a carboxylic acid and an anhydride; and

(ii) a second component comprising at least one material selected from the group consisting of a dialkylaminoalkyl acrylate monomer, a dialkylaminoalkyl methacrylate monomer, and an alkyl alkanolamine monomer.

44. The vehicle system of claim 43, wherein the second component is selected from the group consisting of N,N-dimethylaminoethyl acrylate, N,N-dimethylaminoethyl methacrylate;

N,N-diethylaminoethyl acrylate, N,N-diethylaminopropyl acrylate, N,N-dimethylaminoethyl methacrylate, N,N-diethylaminoethyl methacrylate, N,N-diethylaminopropyl methacrylate, N,N-diethylaminopropyl acrylate;

N,N-diethylaminobutyl methacrylate; and

N,N-diethylaminobutyl acrylate.

45. The vehicle system of claim 43, wherein the additive comprises the reaction product of 3,3′

,4,4′

-benzophenonetetracarboxylic acid and N,N-dimethylaminoethyl-methacrylate.

46. The vehicle system of claim 43, wherein the additive comprises the reaction product of benzophenone carboxylic acid or orthobenzoylbenzoic acid, and N,N-dimethylaminoethyl methacrylate.

47. The vehicle system of claim 43, wherein the first component comprises about 2-50% acrylic resin, water up to about 75%, and about 0-20% diluting agent.

48. The vehicle system of claim 47, wherein the diluting agent is selected from the group consisting of monoethanolamine, dimethanolamine, triethanolamine, ammonia, morpholine, propylene glycol and polypropylene glycol.

49. The vehicle system of claim 43, wherein the second component comprises about 2-50% fumaric resin, water up to about 75%, and about 0-30% diluting agent.

50. The vehicle system of claim 49, wherein the diluting agent is selected from the group consisting of monoethanolamine, dimethanolamine, triethanolamine, ammonia, propylene glycol, and polypropylene glycol.

51. The vehicle system of claim 43, wherein the first component is selected from the group consisting of a waterborne urethane dispersion and a microcrystalline wax dispersion.

52. The vehicle system of claim 43, wherein the first component is selected from the group consisting of corn oil, cottonseed oil, olive oil, palm oil, palm kernel oil, peanut oil, linseed oil, soybean oil, tall oil, and tung oil.

53. The vehicle system of claim 43, wherein the first component comprises about 50-100% acrylic emulsion resin and water up to about 30%.

54. An ink, coating, or adhesive made with the vehicle according to claim 43.

55. The paint, ink, or coating of claim 43, further comprising at least one of an inhibitor in an amount of about 0.05 to 2.0 weight percent, a surfactant in an amount of about 0.05 to 0.5 percent, and a defoamer in an amount of about 0.05 to 0.5 percent.