Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Patent
1997-03-10
1998-03-10
Bell, Mark L.
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
106495, 25230116, 313504, 428690, 546 56, 546 57, C09B 4800
Patent
active
057256519
DESCRIPTION:
BRIEF SUMMARY
The instant invention relates to mono-N-alkyl-quinacridone pigments. Quinacridones are well known as valuable organic pigments, in particular as colouring materials for high molecular weight organic materials (see, for example, S.S. Labena et al, Chem. Rev., 67, 1 (1967).
On the other hand, Carmichael et al, J. Phys. Chem. Ref. Data, 16, 239 (1987) describes spectral properties of N-methyl-quinacridone in solution.
However, Carmichael et al neither disclose nor suggest the properties and the method of production of N-methyl-quinacridone pigment.
Accordingly, nothing is known about N-alkyl-quinacridone pigments, in particular that they exhibit the following surprising properties: stability over 400.degree. C. and migration fastness, enabling the application of these pigments as colouring materials for high molecular weight organic materials, such as natural or synthetic resins, e.g. polyolefins, polyesters and polyamides; quinacridones; taking place under irradiation with visible light (around 490 nm wavelength), enabling the application of the pigments as fluorescent pigments as well as light emitting materials of organic electroluminescent elements; quinacridones, taking place under irradiation with light of 400-600 nm wavelength, enabling the application of the pigments as photoreceptors for electrophotography and solar cells.
The invention relates to:
a N-alkyl-quinacridone pigment possessing the above mentioned properties represented by formula ##STR1## wherein Z is C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by F, Cl, Br, --OH, --O--C.sub.1 -C.sub.18 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, phenyl or naphthyl; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of the other (i) H, (ii) F, Cl or Br, (iii) --OH, (iv) --CN, (v) --NO.sub.2, (vi) C.sub.1 -C.sub.18 -alkyl, phenyl or naphthyl, which alkyl, phenyl or naphthyl is unsubstituted or substituted by F, Cl, Br, --OH, --CN, --NO.sub.2, pheny or naphthyl, which phenyl or naphthyl is unsubstituted or substituted by F, Cl, Br, C.sub.1 -C.sub.18 -alkyl or --O--C.sub.1 -C.sub.18 -alkyl, a heterocyclic aromatic residue, --OCOR.sub.5, --OR.sub.6, --COOR.sub.5, --N(R.sub.6)(R.sub.7) or --CON(R.sub.6)(R.sub.7), in which R.sub.5 is C.sub.1 -C.sub.18 -alkyl, phenyl, naphthyl or benzyl, which alkyl, phenyl, naphthyl or benzyl is unsubstituted or substituted by F, Cl, Br, C.sub.1 -C.sub.18 -alkyl or --O13 C.sub.1 -C.sub.18 -alkyl, and in which R.sub.6 and R.sub.7 are each independently of the other C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by --CN or --OH; C.sub.3 -C.sub.7 -cycloalkyl, phenyl or naphthyl, which cycloalkyl, phenyl or naphthyl is unsubstituted or substituted by F, CI, Br, C.sub.1 -C.sub.18 -alkyl or --O--C.sub.1 -C.sub.18 -alkyl, or R.sub.6 and R.sub.7 together with the N atom form a 5-membered or 6-membered hetero ring; (vii) --OR.sub.8, in which R.sub.8 is C.sub.1 -C.sub.18 -alkyl, phenyl, naphthyl or C.sub.3 -C.sub.7 -cycloalkyl, which alkyl, phenyl, naphthyl or cycloalkyl is unsubstituted or substituted by F, Cl, Br, C.sub.1 -C.sub.18 -alkyl or --O--C.sub.1 -C.sub.18 -alkyl, or benzyl, (viii) --SR.sub.8, (ix) --N(R.sub.6)(R.sub.7), (x) --COOR.sub.5, (xi) --N(R.sub.9)COR.sub.5, in which R.sub.9 is C.sub.1 -C.sub.18 -alkyl, phenyl, naphthyl or C.sub.3 -C.sub.7 -cycloalkyl, which alkyl, phenyl, naphthyl or cycloalkyl is unsubstituted or substituted by F, Cl, Br, C.sub.1 -C.sub.18 -alkyl or --O--C.sub.1 -C.sub.18 -alkyl, benzyl or the residue --COR.sub.5, or in which R.sub.9 together with the N atom form a heterocyclic ring, (xii) --N(R.sub.8)COOR.sub.5, (xiii) --NR.sub.8 CON(R.sub.6)(R.sub.7), (xiv) --SO.sub.2 R.sub.5 or --SOR.sub.5, (xv) --SO.sub.2 OR.sub.5, (xvi) --CON(R.sub.6)(R.sub.7), (xvii) --SO.sub.2 N(R.sub.6)(R.sub.7), (xviii) --N=N-R.sub.10, in which R.sub.10 is the residue of a coupling component, or phenyl which is unsubstituted or substituted by F, CI, Br, C.sub.1 -C.sub.18 -alkyl or --O--C.sub.1 -C.sub.18 -alkyl, or (xix) --OCOR.sub.5, in which substituents (ix)-(xiv) R.sub.5, R.sub.6 and
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Mizuguchi Jin
Zambounis John
Bell Mark L.
Ciba Specialty Chemicals Corporation
Hertzog Scott L.
Mansfield Kevin T.
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