Penetrants for aqueous ink jet inks

• US 5,141,556 A
• Filed: 06/13/1991
• Issued: 08/25/1992
• Est. Priority Date: 06/13/1991
• Status: Expired due to Fees

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Matrick, Howard
• Primary Examiner(s): Dixon, Jr., William R.
• Assistant Examiner(s): Klemanski, Helene
• Application Number:
  US07/714,879
• Time in Patent Office: 439 Days
• Field of Search: 106/20, 106/22, 106/23
• US Class Current: 524/385
• CPC Class Codes: C09D 11/30 Inkjet printing inks

Abstract

An ink for ink jet printers which comprises an aqueous carrier medium, pigment dispersion or dye and a diol penetrant. The latter is an aliphatic diol having at least 6 carbon atoms, a solubility in water of at least 4.5 parts in 100 parts of water at 25° C. and is selected from the group consisting essentially of:

(1) compounds wherein at least 2 carbon atoms are attached as substituents to the main chain, and

(2) Hexene [1,2-]diols.

The pigment dispersion consists of pigment particles and a dispersant, preferably a polymeric dispersant having a hydrophilic segment and a segment that links to the pigment. These inks exhibit rapid drying, are storage stable, have reliable performance and give images having good print quality.

Claims

1. An aqueous ink jet ink composition comprising:

(a) an aqueous carrier medium,

(b) a pigment dispersion or dye; and

(c) an aliphatic diol penetrant compound having at least 6 carbon atoms, a solubility in water of at least 4.5 parts in 100 parts of water at 25°

C., and selected from the group consisting of

(1) compounds wherein at least 2 carbon atoms are attached as substituents to the main chain and represented by the general formula

space="preserve" listing-type="equation">C.sub.n H.sub.2n (OH).sub.2

wherein n is at least 6; and

(2) Hexene[1,2]diols.

2. The ink composition of claim 1 wherein the pigment dispersion comprises a pigment and a polymeric dispersant.

3. The ink composition of claim 1 wherein n is 6-8.

4. The ink composition of claim 1 wherein at least 2 side chain or branched carbon atoms are attached to the same main chain carbon atom.

5. The ink composition of claim 1 wherein the diol penetrant is a 1,3-diol having the general formula:

##STR2## wherein R is H or alkyl of 1-2 carbon atoms and R'"'"' is alkyl of 2-6 carbon atoms.

6. The ink composition of claim 5 wherein R is --CH₃ or --C₂ H₅, and R'"'"' is C₂ H₅ or C₃ H₇.

7. The ink composition of claim 6 wherein the diol penetrant is 2-ethyl-2-methyl-1,3-propanediol.

8. The ink composition of claim 6 wherein the diol penetrant is 2,2-diethyl-1,3-propanediol.

9. The ink composition of claim 6 wherein the diol penetrant is 2-methyl2-propyl-1,3-propanediol.

10. The ink of claim 1 wherein the diol penetrant is a 2,4- or 2,5-diol having the general formula:

space="preserve" listing-type="equation">(CH.sub.3).sub.2 COH(CH.sub.2).sub.n COH(CH.sub.3).sub.2

wherein n=1-2.

11. The ink composition of claim 10 wherein the diol penetrant is 2,4-dimethyl-2,4-pentanediol.

12. The ink composition of claim 10 wherein the diol penetrant is 2,5-dimethyl-2,5-hexanediol.

13. The ink composition of claim 4 wherein the diol penetrant is 3,3-dimethyl-1,2-butanediol.

14. The ink composition of claim 1 or 2 wherein the diol penetrant is 5-hexene-1,2-diol.

15. The ink composition of claim 2 wherein the polymeric dispersant is an AB or BAB block copolymer wherein

(a) the A segment is a hydrophobic homopolymer or copolymer of an acrylic monomer having the formula:

space="preserve" listing-type="equation">CH.sub.2 =C(X)(Y)

wherein X is H or CH₃ ; and

Y is C(O)OR₁, C(O)NR₂ R₃, or CN, wherein R₁ is an alkyl, aryl, or alkylaryl group having 1 to 20 carbon atoms, and R₂ and R₃ are hydrogen or an alkyl, aryl, or alkylaryl group having 1 to 9 carbon atoms;

said A segment having an average molecular weight of at least approximately 300 and being water insoluble; and

(b) the B segment is a hydrophilic polymer, or salt thereof, of

(1) an acrylic monomer having the formula

space="preserve" listing-type="equation">CH.sub.2 =C(X)(Y.sub.1),

wherein X is H or CH₃ ; and

Y₁ is C(O)OH, C(O)NR₂ R₃, C(O)OR₄ NR₂ R₃ or C(OR₅);

wherein R₂ and R₃ are hydrogen or an alkyl, aryl, or alkylaryl group having 1 to 9 carbon atoms;

R₄ is an alkyl diradical having 1 to 5 carbon atoms; and

R₅ is an alkyl diradical having 1 to 20 carbon atoms and optionally containing one or more hydroxyl or ether groups;

or

(2) a copolymer of the acrylic monomer of (1) with an acrylic monomer having the formula;

space="preserve" listing-type="equation">CH.sub.2 =C(X)(Y)

where X and Y are the substituent groups defined for the A segment;

the B segment having an average molecular weight of at least approximately 300,and being water soluble.

16. The pigmented ink of claim 15 wherein the polymeric dispersant is an AB or BAB block copolymer wherein the A segment of said block copolymer is a homopolymer or copolymer prepared from at least one monomer selected from the group consisting of methyl methacrylate, ethylmethacrylate, propyl methacrylate, butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, lauryl methacrylate, stearyl methacrylate, phenyl methacrylate, benzyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-ethoxyethyl methacrylate, methacrylonitrile, 2-trimethylsiloxyethyl methacrylate, glycidyl methacrylate, p-tolyl methacrylate, sorbyl methacrylate, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, lauryl acrylate, stearyl acrylate, phenyl acrylate, benzyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, acrylonitrile, 2-trimethyl-siloxyethyl acrylate, glycidyl acrylate, p-tolyl acrylate, and sorbyl acrylate.

17. The ink composition of claim 16 wherein the A segment of said block copolymer is a homopolymer or copolymer prepared from methyl methacrylate, n-butyl methacrylate, 2-ethylhexyl methacrylate or a copolymer ethyl methacrylate with butyl methacrylate.

18. The ink composition of claim 17 wherein the A segment is n-butyl methacrylate.

19. The ink composition of claim 15 wherein the B segment of said block copolymer is a homopolymer or copolymer prepared from at least one monomer selected from the group consisting essentially of methacrylic acid, acrylic acid, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, t-butylaminoethyl methacrylate, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, dimethylaminopropyl methacrylamide, methacrylamide, acrylamide, and dimethylacrylamide.

20. The ink composition of claim 19 wherein the B segment of said block copolymer is a polymer of methacrylic acid or dimethylaminoethyl methacrylate.

21. The ink composition of claim 20 wherein the B segment of said block copolymer is a homopolymer polymer of methacrylic acid.

22. The ink composition of claim 20 wherein said ink contains approximately 0.1 to 15% pigment, 0.1 to 30% block copolymer, and 70 to 99.8% aqueous carrier medium plus penetrant, based on the weight of the total ink composition.

23. The ink composition of claim 22 wherein the aqueous carrier medium comprises water and at least one water soluble organic solvent.

24. The ink composition of claim 23 wherein aqueous carrier medium plus penetrant contains from 30% water/70% solvent/penetrant mixture to 95% water/5% solvent/penetrant mixture, based on the total weight of the aqueous carrier medium plus penetrant.

25. The ink composition of claim 24 wherein the solvent/penetrant mixture contains 15-95% penetrant, based on the weight of the solvent/penetrant mixture.

26. The ink composition of claim 25 wherein the solvent/penetrant mixture contains 25-75% penetrant, based on the weight of the solvent/penetrant mixture.

27. The ink composition of claim 22 wherein said ink contains approximately 0.1 to 8% pigment, 0.1 to 8% block copolymer, and 94 to 99.8% aqueous carrier medium plus penetrant, based on the weight of the total ink composition.

28. The ink composition of claim 15 wherein the A segment of said block copolymer is a polymer of methyl methacrylate, butyl methacrylate, or 2-ethylhexyl methacrylate and the B segment is a polymer of methacrylic acid or dimethylaminoethyl methacrylate.

29. The ink composition of claim 15 wherein the B segment(s) constitute approximately 25 to 65%, by weight, of said block copolymer.

30. The ink composition of claim 1 wherein said ink contains approximately 0.2 to 20% dye, and 80 to 99.8% aqueous carrier medium plus penetrant, based on the weight of the total ink composition.

31. The ink composition of claim 30 wherein said aqueous carrier medium plus penetrant contains 15-95% penetrant based on the weight of the aqueous carrier medium plus penetrant.

32. The ink of claims 1 or 2 wherein the aqueous carrier medium is a mixture of water and at least one water soluble organic solvent having at least 2 hydroxyl groups.

33. The ink composition of claim 2 wherein the pigment particles have a median particle size of approximately 0.01 to 1 micron.

34. The ink composition of claim 2 wherein the polymeric dispersant is neutralized with a neutralizing agent selected from the group consisting of organic bases, alkanolamines, alkali metal hydroxides, and mixtures thereof.

35. An ink composition of claims 1 or 2 wherein a surfactant is present.

36. An ink composition of claim 35 wherein the surfactant is a polyalkyleneoxide modified polydimethylsiloxane.