Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Patent
1998-10-05
2000-10-03
Green, Anthony
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
106494, 524 89, 544251, C09B 1700, C09B 5700, C08K 534, C07D48714
Patent
active
06126735&
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for mass colouring high molecular weight organic material with pyrimidopteridines as well as to novel pyrimidopteridines.
Pyrimidopteridines are known compounds. In Ann., 545, 209 (1940), H. Wieland et al. mention hydroxy-substituted pyrimidopteridines as reaction products of wing pigments of butterflies. JACS, 77, 2243-2248 (1955), an article devoted to the synthesis of amino- and hydroxy-substituted pyrimidopteridines, describes these products as sparingly soluble yellow substances. Pyrimidopteridines which are substituted at at least two nitrogen atoms of the ring system are disclosed as fluorescent pigments in JP-A 93-202046, JP-A 93-202053, JP-A 94-41135 and JP-A 95-278456. DE-A 4415656 discloses pyrimidopteridine salts as pigments. The known mixtures of pyrimidopteridine compounds with high molecular organic materials normally already have good lightfastness properties which, however, are still not sufficiently good for a number of applications, especially when used as automotive lacquers.
High requirements are placed on pigments which are suitable for a wide range of applications in high molecular weight organic material, such as high chroma, high colour strength, excellent fastness properties, such as fastness to light, weathering, migration and heat, good dispersibility and easy accessibility.
Accordingly, it is the object of this invention to provide a high molecular weight organic material coloured with pyrimidopteridine compounds and having improved fastness to light. In particular, a cumulation of the above-mentioned advantages was to be attained with the pyrimidopteridines which are unsubstituted at the nitrogen atoms of the ring system and which are not saline.
An improved process has accordingly been found for mass colouring high molecular weight organic material with pyrimidopteridines in a manner known per se by using a pyrimidopteridine of formula I and/or II. ##STR3## wherein A, B, C and D are each independently of one another --NH.sub.2, --OH, hydrogen, C.sub.1 -C.sub.4 -alkyl; phenyl, biphenyl or naphthyl which are unsubstituted or substituted by halogen, --OH, --NH.sub.2, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; --NHR.sub.1, --N(R.sub.1).sub.2 or ##STR4## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl; phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 -alkoxy, or --COXR.sub.2, substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 -alkoxy, with the proviso that at least two of the radicals A, B, C and D are --NH.sub.2 or --OH.
The compounds of formulae I and II can also be obtained in another tautomeric form, i.e. those tautomeric forms are also included under formulae I and II.
Should some substituents be halogen, then they are typically fluoro, bromo or chloro, in particular bromo or chloro and, preferably, chloro.
C.sub.1 -C.sub.4 Akyl is typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl or tert-butyl, and C.sub.1 -C.sub.4 alkoxy is typically methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-, i- or tert-butoxy.
A special embodiment of this invention relates to a process for colouring high molecular weight organic materials by using pyrimidopteridines of formulae I or II or a mixture thereof, wherein hydrogen, methyl, ethyl; phenyl which is unsubstituted or substituted by --OH or --NH.sub.2, typically p-hydroxyphenyl and p-aminophenyl, or NHCOXR.sub.2, wherein substituted by chloro, methyl, ethyl, methoxy or ethoxy, with the proviso that at least two of the radicals A, B, C and D are --NH.sub.2 or --OH.
A particularly preferred embodiment of this invention relates to a process for colouring high molecular weight organic material by using pyrimidopteridines of formula I or II or a mixture thereof, wherein A, B, C and D are each independently of one another --NH.sub.2, --OH, hydrogen, methyl; phenyl which is unsubstituted or substituted by --NH.sub.2, or --NHCOR.sub.2, and R.sub.2 is methyl, ethyl or phenyl, and wherein A and D, and B and C, are i
REFERENCES:
patent: 5525152 (1996-06-01), Roschger et al.
Chem. Abst. 120:772289e of JP 5,202,053[93-202,053] (Aug. 1993).
Patent abst. Of Japan of JP 06-041135 (Feb. 1994).
Derw. Abst. 95-401177/51 of JP 07-278456 (Apr. 1994).
J. of Amer. Chem. Soc. vol. 77 (1955) pp.2243-2248 (No Month).
Ann. 545 (1940) pp. 209-219, Wieland et al. "Uberdie Flugelpigmente der Schmetterlinge" (No Month).
Derw. Abst. 93-290580 of Jp 5202046 (Jan. 1992).
Chemical Abstract No. 121:83370, abstract of Japanese Patent Specification No. 06-041134. Feb. 1994.
Eichenberger Thomas
Hugin Max
Ciba Specialty Chemicals Corporation
Crichton David R.
Green Anthony
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