Pigmented vitreous material
AssigneeCiba Specialty Chemicals Corporation
InventorsPatrice Bujard, Veronique Hall-Goulle, Zhimin Hao, Hitoshi Nagasue, Gerardus De Keyzer
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Abstract
The present application relates to a process for the manufacture of pigmented vitreous materials, as well as to pigmented vitreous materials, characterized by the use of soluble pigment precursors and preferably the absence of significant amounts of dispersants. These pigmented vitreous materials can be used as coloured materials for any known purposes. Soluble pigment precursors comprising a partial structure 1 are also claimed, wherein X1 is an aromatic or heteroaromatic ring, B is hydrogen or a group of the formula 2 but at least one group B is not hydrogen, and L is a solubilizing group.
Claims13
A process for making a pigmented vitreous material from a liquid or dissolved transition metal compound, wherein the liquid or dissolved transition metal compound reacts to form crosslinks between the liquid or dissolved transition metal atoms in the pigmented vitreous material, characterized in that the solution also comprises a dissolved compound of the formula
- A(B)x (I),
- in which x is an integer from 1 to 8,
- A is the radical of a chromophor of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine, diketopyrrolopyrrole or 3-methylidene-2,3-dihydro-indol-2-on series which is attached to x groups B via one or more heteroatoms selected from the group consisting of N, O and S and forming part of the radical A,
- B is hydrogen or a group of the formula
- 30
- where at least one group B is not hydrogen and, if x is from 2 to 8, the groups B can be identical or different, and
- L is any suitable solubilizing group,
- and the vitreous material is heated so that the compound of the formula (I) is transformed into a pigment of the formula A(H)x (II), in which x has the same meaning as in formula (I).
A 2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione of the formula
- 35
- in which X1 and X2 independently of one another are a divalent aromatic radical of the formula
- 36
- R3 is a radical CN, COR6, CO2R6, CON(R6)2, NO2, SO2R6, SOR6, SO2N(R6)2 or PO(OR7)2,
- R4 and R5 independently of one another are hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,
- R7 is C1-C6alkyl or phenyl,
- R1, R2, R1′, R2′ and Re independently of one another are hydrogen, C1-C18alkyl or C1-C18alkenyl which is unsubstituted or substituted by hydroxy, mercapto, C1-C6alkoxy or C1-C6alkylmercapto, or phenyl which is unsubstituted or substituted by chlorine, bromine, hydroxy, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylmercapto, CN, NO2 or CF3,
- or R1 and R2 or R1′ and R2′, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic radical which is unsubstituted or substituted by C1-C6alkyl or phenyl and is selected from the group consisting of pyrrolidinyl, piperidyl, pyrrolyl, triazolyl, imidazolyl, pyrazolyl, piperazinyl, morpholinyl, thiomorpholinyl, carbazol-1-yl, indol-1-yl, indazol-1-yl, benzimidazol-1-yl, tetrahydroquinol-1-yl and tetrahydroquinol-2-yl, or,
- if R1 or R1′ is hydrogen, R2 or R2′ is a radical of the formula
- 37
- in which X3 and X4 independently of one another are hydrogen, chlorine, bromine, NO2, methyl, methoxy or ethoxy and X5 and X6 form a 5- or 6-membered heterocyclic ring which together with A produces a benzimidazolonyl, dihydroxyquinazolinyl, quinolonyl, benzoxazolonyl, phenmorpholonyl, quinazolinonyl or phthalimidyl radical or a radical of the formula
- 38
- in which R8 is C1-C6alkyl or phenyl,
- or X2-R3 can be a radical
- 39
- and
- E1 is hydrogen and E2 is a group B, E1 is a group B and E2 is hydrogen, or E1 and E2 are both a group B,
- with the proviso that when said 2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione is of formula (IIIb), R1 is not C1-C18alkylamino.
A vitreous material comprising a matrix of crosslinked liquid or dissolved transition metal atoms and an effective pigmenting amount of a pigment selected from from Colour Index Pigment Yellow 13, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 93, Pigment Yellow 94, Pigment Yellow 95, Pigment Yellow 109, Pigment Yellow 120, Pigment Yellow 128, Pigment Yellow 139, Pigment Yellow 151, Pigment Yellow 154, Pigment Yellow 175, Pigment Yellow 180, Pigment Yellow 181, Pigment Yellow 185, Pigment Yellow 194, Pigment Orange 31, Pigment Orange 71, Pigment Orange 73, Pigment Red 144, Pigment Red 166, Pigment Red 184, Pigment Red 185, Pigment Red 202, Pigment Red 214, Pigment Red 220, Pigment Red 221, Pigment Red 222, Pigment Red 242, Pigment Red 248, Pigment Red 255, Pigment Red 262, Pigment Red 264, Pigment Brown 23, Pigment Brown 41, Pigment Brown 42, Pigment Blue 25, Pigment Blue 26, Pigment Blue 60, Pigment Blue 64, Pigment Violet 29, Pigment Violet 32, Pigment Violet 37, 3,6-di(4′-cyano-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione or 3-phenyl-6-(4′-tert-butyl-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione.
Dependencies are inferred from the claim text.