Soluble chromophores containing solubilising groups which can be easily removed

• US 6,063,924 A
• Filed: 07/22/1996
• Issued: 05/16/2000
• Est. Priority Date: 07/28/1995
• Status: Expired due to Term

• Current Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Original Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Inventors: Hall-Goulle, Veronique
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): RAO, DEEPAK R
• Application Number:
  US08/681,204
• Time in Patent Office: 1,394 Days
• Field of Search: 548/453, 548/457, 548/471, 548/479, 548/482, 546/256, 546/276.7, 546/49, 546/56, 546/36, 546/41, 546/57, 544/296, 544/333, 544/99, 544/300, 544/380, 540/122, 540/135, 540/136, 534/618, 534/624, 534/634, 534/732, 534/733, 534/790, 552/213
• US Class Current: 546/49
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C09B 1/005 Di-anthraquinonyl and derivative compounds
• CPC Class Codes: C09B 19/02 Bisoxazines prepared from aminoquinones
• CPC Class Codes: C09B 29/0037 containing a five-membered heterocyclic ring with two nitrogen atoms
• CPC Class Codes: C09B 47/16 having alkyl radicals substituted by nitrogen atoms
• CPC Class Codes: C09B 47/26 Amide radicals
• CPC Class Codes: C09B 48/00 Quinacridones
• CPC Class Codes: C09B 5/62 Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
• CPC Class Codes: C09B 57/004 Diketopyrrolopyrrole dyes
• CPC Class Codes: C09B 57/04 Isoindoline dyes
• CPC Class Codes: C09B 68/443 Carboxylic acid derivatives, e.g. carboxylic acid amides, carboxylic acid esters or CN groups
• CPC Class Codes: C09B 68/46 Aromatic cyclic groups
• CPC Class Codes: C09B 69/08 Dyes containing a splittable water solubilising group dyes containing an onium group attached to the dye molecule via a bridge are to be considered as cationic dyes and are classified with the respective dyes such as C09B44/02 - C09B44/08; C09B69/001 - C09B69/005
• CPC Class Codes: C09B 7/02 Bis-indole indigos
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials

Abstract

Compounds of formula

A(B).sub.x                                                 (I),

wherein x is an integer from 1 to 4,

A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, isoindolinone, isoindoline, dioxazine, phthalocyanine, diketopyrrolopyrrole or azo series, which radical A contains x N-atoms linked with B, preferably with at least one immediately adjacent or conjugated carbonyl group.

B is a group of formula ##STR1## and, if x=2, 3 or 4, can also be one, two or three hydrogen atom(s), and wherein Q is a group of formula ##STR2## These soluble chromophores can be readily converted to the corresponding pigments by heating, even in the substrate into which they can be incorporated without any difficulty in dissolved form.

R₁ -R₉ are as defined herein.

Claims

1. A compound of formula

View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)

2. A compound according to claim 1 of formula I, wherein R₁ is C₁ -C₂₄ alkyl, C₃ -C₂₄ alkenyl, C₃ -C₂₄ alkynyl, phenyl which is unsubstituted or substituted by C₁ -C₆ alkyl, C₁ -C₆ alkoxy, halogen, cyano or nitro, and R₆ is C₁ -C₂₄ alkyl or C₃ -C₂₄ alkenyl.

3. A compound according to claim 1 of formula I, wherein

R₁ and R₂ are methyl,

R₃, R₄ and R₅ are each independently of one another hydrogen or C₁ -C₁₂ alkyl, and

R₆ is C₁ -C₆ alkyl.

4. A compound according to claim 3 of formula I, wherein

B is a group of formula ##STR54## R₁ and R₂ are methyl, and R₃, R₄ and R₅ are each independently of one another hydrogen or C₁ -C₁₂ alkyl.

5. A compound according to claim 1 selected from the group consisting of

a) perylenecarboximides of formula ##STR55## wherein D is hydrogen, C₁ -C₆ alkyl;

unsubstituted or halogen- or C₁ -C₆ alkyl-substituted phenyl, benzyl or phenethyl, or B,

b) quinacridones of formula ##STR56## wherein R₁₃ and R₁₄ are each independently of the other hydrogen, halogen, C₁ -C₂₄ alkyl, C₁ -C₆ alkoxy or phenyl,

c) dioxazines of formula ##STR57## wherein R₁₅ is hydrogen, halogen or C₁ -C₂₄ alkyl, or of formula ##STR58## wherein R and R'"'"' are each independently of the other C₁ -C₄ alkyl,

d) isoindolines of formulae ##STR59## wherein R₁₆ is a group of formula ##STR60## R₁₇ is hydrogen, C₁ -C₂₄ alkyl, benzyl or a group of formula ##STR61## R₁₈ has the same meaning as R₁₆, R₁₉, R₂₀, R₂₁ and R₂₂ are each independently of one another hydrogen, C₁ -C₂₄ alkyl, C₁ -C₆ alkoxy, halogen or trifluoromethyl,

e) indigo derivatives of formula ##STR62## wherein R₂₃ is hydrogen, CN, C₁ -C₆ alkyl, C₁ -C₆ alkoxy or halogen,

f) azobenzimidazolones of formula ##STR63## wherein R₂₄ and R₂₅ are each independently of the other hydrogen, halogen, C₁ -C₆ alkyl or C₁ -C₆ alkoxy,

g) anthraquinoid compounds of formula ##STR64## h) phthalocyanines of formula ##STR65## wherein X₁ is H₂, a divalent metal selected from the group consisting of Cu(II), Zn(II), Fe(II), Ni(II), Ru(II), Rh(II), Pd(II), Pt(II), Mn(II), Mg(II), Be(II), Ca(II), Ba(II), Cd(II), Hg(II), Sn(II), Co(II) and Pb(II), or a divalent oxo metal selected from the group consisting of V(O), Mn(O) and TiO,

X₂ is --CH(R₂₄)--, --CO-- or --SO₂ --,

R₂₆ is hydrogen, C₁ -C₆ alkyl, --N(E)R₂₇, --NHCOR₂₈, --COR₂₈ or ##STR66## R₂₇ is hydrogen or C₁ -C₆ alkyl, R₂₈ is C₁ -C₆ alkyl, and R₂₉ is hydrogen, halogen, C₁ -C₆ alkyl or C₁ -C₆ alkoxy,

z is 0 or 1, and y is an integer from 1 to 4, and

i) isoindolinones of formula ##STR67## wherein R" is hydrogen or C₁ -C₄ alkyl, E in the above formulae being hydrogen or B, with the proviso that E in each formula is at least once B, and B is as claimed in claim 1.

6. A compound according to claim 5 selected from the group consisting of

quinacridones of formula III, wherein R₁₃ and R₁₄ are each independently of the other hydrogen, chloro or methyl, or

anthraquinoid compounds of formula XI

wherein E in formulae III and XI is defined as in claim 5.

7. A compound according to claim 4, of formula ##STR68## wherein E is hydrogen or B, with the proviso that E in each formula is at least once B, and B is as claimed in claim 4.

8. A compound according to claim 1 of formula I, wherein the N-atoms linked to B are directly adjacent to or conjugated with at least one carbonyl group.

9. A compound according to claim 4, of formula ##STR69## wherein E is hydrogen or B, with the proviso that E is at least once B, and B is as claimed in claim 4.