Boronic acid dyes

• US 5,108,502 A
• Filed: 08/28/1991
• Issued: 04/28/1992
• Est. Priority Date: 03/16/1990
• Status: Expired due to Fees

• Current Assignee: Hewlett-Packard Company (HP Inc.)
• Original Assignee: Hewlett-Packard Company (HP Inc.)
• Inventors: Pawlowski, Norman E., Robotti, Karla M., Russell, Dale D.
• Primary Examiner(s): Dixon, Jr., William R.
• Assistant Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US07/751,457
• Time in Patent Office: 244 Days
• Field of Search: 106/22, 8/662, 534/726, 568/1, 568/6
• US Class Current: 106/31.48
• CPC Class Codes: C09B 29/0007 containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
• CPC Class Codes: C09B 31/057 containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
• CPC Class Codes: C09B 31/072 containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
• CPC Class Codes: C09D 11/328 characterised by dyes

Abstract

Boronic dyes corresponding to the formula ##STR1## wherein D is an organic dye moiety, and n is 1 or 2 are described. Inks which are formulated for ink-jet printing and contain such a dye provide excellent images when printed on paper.

Claims

1. An azo dye of the formula ##STR32## wherein Ar is a phenylene or substituted phenylene, Ar₁ is an arylene or substituted arylene free of sulfonate groups, Ar₂ is an aryl or substituted aryl free of sulfonate groups, m is 0 or an integer from 1 to about 4, and n is an integer from 1 to 2.

2. The azo dye of claim 1 wherein Ar₁ is an arylene or substituted arylene selected from the group consisting of hydroxyphenylene, aminophenylene, N,N-di(lower alkyl)-aminophenylene, bromophenylene, chlorophenylene, lower alkylphenylene, nitrophenylene, naphthalene, hydroxynaphthylene, chloronaphthylene, bromonaphthylene, nitronaphthylene, aminonaphthylene, N,N-di-(lower alkyl)aminonaphthylene, methoxyphenylene, and lower alkyl naphthylene, Ar₂ is an aryl or substituted aryl selected from the group consisting of hydroxyphenyl, aminophenyl, hydroxyaminophenyl, N,N-di(lower alkyl)-aminophenyl, N,N-di(lower alkyl)-aminocarboxyphenyl, bromophenyl, chlorophenyl, lower alkylphenyl, nitrophenyl, hydroxynitrophenyl, hydroxycarboxylphenyl, carboxylacrylamidophenyl, succinimidophenyl, tetrahydrocarboxylmethylphthalimidophenyl, naphthyl, hydroxynaphthyl, chloronaphthyl, bromonaphthyl, nitronaphthyl, hydroxynitronaphthyl, aminonaphthyl, N,N-di(lower alkyl)aminonaphthyl, lower alkyl naphthyl, hydroxyaminonaphthyl, dihydroxyaminonaphthyl, hydroxydiaminonaphthyl, hydroxycarboxylnaphthyl, hydroxyaminoquinolyl, and aminomethoxydibenzofuranyl.

3. The dye of claim 1 wherein n is 1.

4. The dye of claim 1 wherein m is 0.

5. The dye of claim 1 wherein m is 1.

6. The dye of claim 1 wherein m is 2.

7. The dye of claim 1 wherein Ar₂ is substituted by ##STR33##

8. The dye of claim 1 wherein Ar is phenylene, Ar₂ is hydroxyphenyl, m is 0 and n is 1.

9. The dye of claim 1 wherein Ar is phenylene, Ar₂ is 4-(N,N-dimethyl)aminophenyl, m is 0, and n is 1.

10. The dye of claim 1 wherein Ar is phenylene, Ar₂ is 2-hydroxynaphthyl, m is 0, and n is 1.

11. The dye of claim 1 wherein Ar is phenylene, Ar₂ is aminohydroxyphenyl, m is 0 and n is 1.

12. The dye of claim 1 wherein Ar is phenylene, Ar₁ is naphthylene, Ar₂ is 2-aminophenyl-4-boronic acid, m is 1 and n is 1.

13. An ink-jet ink for use in an ink-jet printer comprising:

(a) from about 0.05% to about 10% of a water soluble organic dye which has at least one boronic acid group on an aryl radical,

(b) a pH adjuster to maintain the formulation at a pH from about 6 to about 9, and

(c) the balance water.

14. The ink of claim 13 wherein the dye is azo, triphenyl, anthraquinone, methine, xanthene, azine, oxazine, thiazine, thiazole, quinolinone, aminoketone, nitro, nitroso, phthalocyanine, acridine, indamine and indophenol.

15. The ink of claim 14 wherein

(a) the dye corresponds to the formula:

##STR34## wherein Ar and Ar₁ are each arylene or substituted arylene, Ar₂ is aryl or substituted aryl, m is 0 or an integer from 1 to about 4, and n is 1 or 2;

(b) pH adjuster to maintain the resultant formulation at a pH from about 6 to about 9; and

(c) the balance water.

16. The ink of claim 15 wherein n is 1.

17. The ink of claim 15 wherein m is 1.

18. The ink of claim 15 wherein m is 2.

19. The ink of claim 15 wherein Ar₁ is an arylene or substituted arylene selected from the group consisting of hydroxyphenylene, aminophenylene, N,N-di(lower alkyl)-aminophenylene, bromophenylene, chlorophenylene, lower alkylphenylene, nitrophenylene, naphthalene, hydroxynaphthylene, chloronaphthylene, bromonaphthylene, nitronaphthylene, aminonaphthylene, N,N-di-(lower alkyl)aminonaphthylene, methoxyphenylene, and lower alkyl naphthylene, Ar₂ is an aryl or substituted aryl selected from the group consisting of hydroxyphenyl, aminophenyl, hydroxyaminophenyl, N,N-di(lower alkyl)-aminophenyl, N,N-di(lower alkyl)-aminocarboxyphenyl, bromophenyl, chlorophenyl, lower alkylphenyl, nitrophenyl, hydroxynitrophenyl, hydroxycarboxylphenyl, carboxylacrylamidophenyl, succinimidophenyl, tetrahydrocarboxylmethylphthalimidophenyl, naphthyl, hydroxynaphthyl, chloronaphthyl, bromonaphthyl, nitronaphthyl, hydroxynitronaphthyl, aminonaphthyl, N,N-di(lower alkyl)aminonaphthyl, lower alkyl naphthyl, hydroxyaminonaphthyl, dihydroxyaminonaphthyl, hydroxydiaminonaphthyl, hydroxycarboxylnaphthyl, hydroxyaminoquinolyl, and aminomethoxydibenzofuranyl.

20. The ink of claim 19 wherein Ar₂ is substituted by ##STR35##