Ink jet ink and recording material

• US 20040126510A1
• Filed: 12/12/2003
• Published: 07/01/2004
• Est. Priority Date: 12/20/2002
• Status: Active Grant

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: CIBA Specialty Chemicals
• Inventors: Kondracki, Paul, Wood, Mervin G., Suhadolnik, Joseph
• Granted Patent: US 7,018,454 B2
• Time in Patent Office: Days
• US Class Current: 428/32.1
• 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: C09D 11/38 characterised by non-macromolecular additives other than solvents, pigments or dyes

Abstract

The present invention relates to an ink jet ink, an ink jet recording material or an ink jet system comprising at least one sterically hindered N-hydroxylamine strong acid salt, for example 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium chloride or bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate dihydrochloride; or comprising at least one dialkyl N-hydroxylamine salt, for example chloride, bisulfate, sulfate, phosphate, nitrate, ascorbate, formate, acetate, benzoate, oxalate, citrate, a carboxylate of ethylenediaminetetraacetic acid or of diethylenetriaminepentaacetic acid or polyacrylate salts of N,N-diethylhydroxylamine, N,N-bis(2-hydroxypropyl)hydroxylamine, N,N-bis(3-hydroxypropyl)hydroxylamine, N,N-dibenzylhydroxylamine or the N,N-di(alkyl)hydroxylamine produced by the direct oxidation of N,N-di(hydrogenated tallow)amine.

Claims

1. An ink jet ink or ink jet recording material comprising at least one sterically hindered N-hydroxylamine strong acid salt of the formula

2. An ink jet ink or ink jet recording material according to claim 1 comprising at least one sterically hindered N-hydroxylamine strong acid salt.

3. An ink jet ink or ink jet recording material according to claim 2 where the strong acid is a mineral acid, sulfuric acid, methanesulfonic acid or phosphoric acid.

4. An ink jet ink or ink jet recording material according to claim 2 where the sterically hindered N-hydroxylamine strong acid salts are selected from the group consisting of

5. An ink jet ink or ink jet recording material according to claim 4 where the sterically hindered N-hydroxylamine strong acid salts are selected from the group consisting of formulae A*, B*, C*, D*, S*, X*, Y* and Z*,

wherein

R is hydrogen,

in formula A*,

n is 1 or 2,

when n is 1,

R₁ is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2-6 carbon atoms, propargyl, glycidyl, alkyl of 2 to 20 carbon atoms interrupted by one to ten oxygen atoms, said alkyl substituted by one to five hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or R₁ is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —

COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,

when n is 2,

R₁ is alkylene of 1 to 8 carbon atoms, alkenylene of 4 to 8 carbon atoms, alkylene of 1 to 20 carbon atoms interrupted by one to ten oxygen atoms, substituted by one to five hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,

in formula B*,

m is 1 or 2,

when m is 1,

R₂ is alkyl of 1 to 4 carbon atoms or R₂ is CH₂(OCH₂CH₂)_nOCH₃ where n is 1 to 12, or R₂ is phenyl, or said phenyl substituted by one to three methyl groups, or R₂ is —

NHR₃ where R₃ is alkyl of 1 to 4 carbon atoms or phenyl, or said phenyl substituted by one or two methyl groups,

when m is 2,

R₂ is alkylene of 1 to 8 carbon atoms, alkenylene of 4 to 8 carbon atoms, or R₂ is —

CH₂(OCH₂CH₂)_nOCH₂—

where n is 1 to 12, or R₂ is NHR₄NH where R₄ is of 2 to 6 carbon atoms, aralkylene of 8 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or R₂ is —

CO—

or —

NHCONH,

in formula C*,

R₁₀ is hydrogen or, alkanoyl of 1 to 3 carbon atoms,

x is 1 or 2,

when x is 1,

R₁₁ is hydrogen, alkyl of 1 to 6 carbon atoms or glycidyl, or R₁₁ is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,

when x is 2,

R₁₁ is alkylene of 1 to 6 carbon atoms,

in formula D*,

R₁₀ is hydrogen,

y is 1 or 2,

R₁₂ is defined as R₂ above,

in formula Y* and Z*,

x is 1 or 2,

when x is 1,

R₁ and R₂ are independently alkyl of 1 to 4 carbon atoms or R₁ and R₂ are together tetramethylene, or pentamethylene, R₂ is hydrogen or alkyl of 1 to 4 carbon atoms, said alkyl group substituted by a hydroxyl group,

when x is 2,

R₁ is hydrogen, alkyl of 1 to 4 carbon atoms, said alkyl substituted by a hydroxyl group,

R₂ is alkylene of 2 to 6 carbon atoms, and

R₃ is as defined above.

6. An ink jet ink or ink jet recording material according to claim 4 where the sterically hindered N-hydroxylamine strong acid salts are selected from the group consisting of formulae A*, B*, C* and D*,

wherein

R is hydrogen,

in formula A*,

n is 1,

R₁ is hydrogen, alkyl of 1 to 4 carbon atoms, glycidyl, alkyl of 2 to 4 carbon atoms interrupted by one or two oxygen atoms, said alkyl substituted by one or two hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or R₁ is alkyl of 1 to 4 carbon atoms substituted by —

COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,

in formula B*,

m is 1 or 2,

R₂ is alkyl of 1 to 4 carbon atoms or R₂ is CH₂(OCH₂CH₂)_nOCH₃ where n is 1 to 4,

when m is 2,

R₂ is alkylene of 1 to 8 carbon atoms,

in formula C*,

R₁₀ is hydrogen or alkanoyl of 1 or 2 carbon atoms,

x is 1 or 2,

when x is 1,

R₁₁ is hydrogen, alkyl of 1 to 4 carbon atoms or glycidyl,

R₁₁ is alkyl of 1 to 4 carbon atoms substituted by COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,

when x is 2,

R₁₁ is alkylene of 1 to 6 carbon atoms,

in formula D*,

R₁₀ is hydrogen,

y is 1 or 2,

R₁₂ is defined as R₂ above.

7. An ink jet ink or ink jet recording material according to claim 4 where the sterically hindered N-hydroxylamine strong acid salts are selected from the group consisting of formula B* where X is chloride or bromide.

8. An ink jet ink or ink jet recording material according to claim 4 where the sterically hindered N-hydroxylamine strong acid salts are 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium chloride or bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate dihydrochloride.

9. An ink jet ink or ink jet recording material according to claim 1 comprising at least one dialkyl N-hydroxylamine salt.

10. An ink jet ink or ink jet recording material according to claim 9 where Y is phosphate, phosphonate, carbonate, bicarbonate, nitrate, chloride, bromide, bisulfite, sulfite, bisulfate, sulfate, borate, formate, acetate, benzoate, citrate, oxalate, tartrate, acrylate, polyacrylate, fumarate, maleate, itaconate, glycolate, gluconate, malate, mandelate, tiglate, ascorbate, polymethacrylate, a carboxylate of nitrilotriacetic acid, hydroxyethylethylenediaminetriacetic acid, ethylenediaminetetraacetic acid or of diethylenetriaminepentaacetic acid, a diethylenediaminetetraacetic acid or of diethylenetriaminepentaacetic acid, an alkylsulfonate or an arylsulfonate.

11. An ink jet ink or ink jet recording material according to claim 9 where Y is chloride, bisulfate, sulfate, phosphate, nitrate, ascorbate, formate, acetate, benzoate, oxalate, citrate, a carboxylate of ethylenediaminetetraacetic acid or of diethylenetriaminepentaacetic acid or polyacrylate.

12. An ink jet ink or ink jet recording material according to claim 9 where the dialkyl N-hydroxylamine salts are salts of N,N-dibenzylhydroxylamine, N,N-dimethylhydroxylamine, N,N-diethylhydroxylamine, N,N-bis(2-hydroxypropyl)hydroxylamine, N,N-bis(3-hydroxypropyl)hydroxylamine, N,N-bis(2-carboxyethyl)hydroxylamine, N,N-bis(benzylthiomethyl)-hydroxylamine, N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-didodecylhydroxylamine, N,N-ditetradecylhydroxylamine, N,N-dihexadecylhydroxylamine, N,N-dioctadecylhydroxylamine, N-hexadecyl-N-tetradecylhydroxylamine, N-hexadecyl-N-heptadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N-methyl-N-octadecylhydroxylamine or N,N-di(hydrogenated tallow)hydroxylamine,

13. An ink jet ink or ink jet recording material according to claim 9 where the dialkyl N-hydroxylamine salts are salts of N,N-diethylhydroxylamine, N,N-bis(2-hydroxypropyl)-hydroxylamine, N,N-bis(3-hydroxypropyl)hydroxylamine, N, N-dibenzylhydroxylamine or the N,N-di(alkyl)hydroxylamine produced by the direct oxidation of N,N-di(hydrogenated tallow)amine.

14. An ink jet ink or ink jet recording material according to claim 9 where the dialkyl N-hydroxylamine salt is tris(N,N-diethylhydroxylammonium) citrate.

15. An ink jet ink according to claim 1 which comprises about 0.01 to about 30% by weight of at least one sterically hindered N-hydroxylamine strong acid salt or at least one dialkyl N-hydroxylamine salt, based on the weight of the ink jet ink.

16. An ink jet recording material according to claim 1 which comprises about 1 to about 10000 mg/M² of at least one sterically hindered N-hydroxylamine strong acid salt or at least one dialkyl N-hydroxylamine salt.

17. An ink jet ink or ink jet recording material according to claim 1 further comprising a UV absorber selected from the group consisting of the hydroxyphenylbenzotriazoles, the tris-aryl-s-triazines, the benzophenones, the a-cyanoacrylates, the oxanilides, the benzoxazinones, the benzoates and the a-alkyl cinnamates.

18. An ink jet ink or ink jet recording material according to claim 1 further comprising a UV absorber selected from the group consisting of the hydroxyphenylbenzotriazoles, the tris-aryl-s-triazines and the benzophenones.

19. An ink jet ink or ink jet recording material according to claim 1 further comprising a UV absorber selected from the group consisting of

5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;

2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;

2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole;

2-(2-hydroxy-3,5-di-α

-cumylphenyl)-2H-benzotriazole;

2-(2-hydroxy-3-α

-cumyl-5-tert-octylphenyl)-2H-benzotriazole;

2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole;

2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole;

2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole-5-sulfonic acid, sodium salt;

3-tert-butyl-4-hydroxy-5-(2H-benzotriazol-2-yl)-hydrocinnamic acid;

12-hydroxy-3,6,9-trioxadodecyl 3-tert-butyl-4-hydroxy-5-(2H-benzotriazol-2-yl)-hydrocinnamate;

octyl 3-tert-butyl-4-hydroxy-5-(2H-benzotriazol-2-yl)-hydrocinnamate;

2-(3-t-butyl-2-hydroxy-5-(2-(ω

-hydroxy-octa-(ethyleneoxy)carbonyl-ethyl)-phenyl)-2H-benzotriazole;

4,6-bis(2,4-dimethylphenyl)-2-(4-octyloxy-2-hydroxyphenyl)-s-triazine;

2,4-bis(2-hydroxy-4-butyloxyphenyl)-6-(2,4-bis-butyloxyphenyl)-1,3,5-triazine;

2-[4-(dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)1,3,5-triazine;

the reaction product of tris(2,4-dihydroxyphenyl)-1,3,5-triazine with the mixture of α

-chloropropionic esters (made from isomer mixture of C₇-C₉alcohols);

2,4-dihydroxybenzophenone;

2,2′

, 4,4′

-tetrahydroxy-5,5′

-disulfobenzophenone, disodium salt;

2-hydroxy-4-octyloxybenzophenone;

2-hydroxy-4-dodecyloxybenzophenone;

2,4-dihydroxybenzophenone-5-sulfonic acid and salts thereof;

2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and salts thereof;

2,2′

-dihydroxy-4,4′

dimethoxybenzophenone-5,5′

-disodium sulfonate;

3-(2H-benzotriazol-2-yl)-4-hydroxy-5-sec-butylbenzenesulfonic acid, sodium salt; and

2-(2′

-hydroxy-3′

-tert-butyl-5′

-polyglycolpropionate-phenyl)benzotriazole.

20. An ink jet system, comprising a recording material and at least one colored ink to be applied to the recording material by means of an ink jet nozzle, wherein at least either the recording material or at least one colored ink comprises at least one sterically hindered N-hydroxylamine strong acid salt or at least one dialkyl N-hydroxylamine salt according to claim 1.

21. A process for stabilizing ink jet prints,

which process comprises applying to a recording material for ink jet printing an ink composition comprising

an aqueous or an organic solvent dye solution and

at least one sterically hindered N-hydroxylamine strong acid salt or at least one dialkyl N-hydroxylamine salt according to claim 1 and

drying said recording material.

22. A process for stabilizing ink jet prints,

which process comprises applying to a recording material for ink jet printing

a casting or coating dispersion or an aqueous or organic solution comprising

at least one sterically hindered N-hydroxylamine strong acid salt or at least one dialkyl N-hydroxylamine salt according to claim 1 and

further applying either an ink composition comprising

an aqueous or an organic solvent dye solution, or an ink composition comprising an aqueous or an organic solvent dye solution and at least one sterically hindered N-hydroxylamine strong acid salt or at least one dialkyl N-hydroxylamine salt according to claim 1 and

drying said recording material.