Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-02-02
2001-05-01
Aulakh, Charanjit S. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S056000
Reexamination Certificate
active
06225472
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel compounds which can direct and control the growth and/or crystal phase of pigment particles. Such compounds are particularly useful when present during the synthesis or finishing of an organic pigment.
BACKGROUND OF THE INVENTION
Dihydroquinacridones are intermediates for the production of the well known quinacridone pigments like C.I. Pigment Violet 19, C.I. Pigment Red 202 and C.I. Pigment Red 122.
A number of patents describe processes for the direct synthesis of pigments in a pigmentary form to avoid the additional expensive and oftentimes environmentally unfriendly pigment finishing processes (e.g. processes for particle size reduction and/or crystal-form modification). For example, European Patent No.643,110 and U.S. Pat. No. 5,424,429 describe a direct synthesis of quinacridone solid solutions and 2,9-dichloroquinacridone in pigmentary form, respectively, in the presence of quinacridone phthalimidomethyl derivatives. European Patent No. 685,530 describes the direct synthesis of pigmentary grade dioxazine in the presence of a dioxazine derivative.
It is also known that sulfonic acid derivatives of certain pigments can effectively diminish the crystal growth during the isolation of the pigment from a reaction mixture. Such sulfonic acid derivatives are described, for example, in U.S. Pat. No. 3,386,843. Other patents describe the use of sulfonic acid derivatives of pigments to stabilize against recrystallization and change of crystal modification as, for example, in G.B. Patent No. 1,544,839 which is directed to phthalocyanine pigments.
U.S. Pat. No. 5,755,873 describes a method for the preparation of quinacridone pigments in which a quinacridone derivative is incorporated during synthesis and copending provisional application Serial No. 60/087,773 describes a direct synthesis of pigmentary diketopyrrolopyrrole pigments in the presence of quinacridone or diketopyrrolopyrrole derivatives.
Although the addition of such known pigment derivatives can be advantageous, pigment synthesis in the presence of such derivatives in many cases does not provide the favored pigmentary crystal size, shape or crystal modification.
Copending U.S. Provisional Patent Application entitled “PIGMENT PARTICLE GROWTH AND/OR CRYSTAL PHASE DIRECTORS”, of the present inventor filed Feb. 2, 1999, discloses pigment particle growth and/or crystal phase directors which in many cases allow for the direct synthesis of pigmentary pigments without requiring a finishing step. However, these compounds themselves have coloristic properties and when used with certain pigments can behave as colored impurities and/or can reduce the saturation of the final pigment.
Japanese Patent No. 061 45 546 describes phthalimidomethyl dihydroquinacridones and the use thereof as pigment dispersants.
SUMMARY OF THE INVENTION
The present invention is based on the discovery that new, colorless or only slightly colored compounds derived from 6,13-dihydroquinacridone are effective pigment particle growth controller and crystal phase directors when present during the pigment synthesis or a pigment finishing step. They are particularly effective for quinacridone and diketopyrrolo pyrrole pigments.
Such 6,13-dihydroquinacridone derivatives can be prepared by simple synthesis procedures and offer the pigment manufacturer a means to prepare a pigment providing the preferred color characteristic without requiring an additional pigment finishing step.
Since other known particle growth inhibitors which are derived from pigment derivatives are strongly colored and often can behave as an impurity, the present 6,13-dihydroquinacridone derivatives are only slightly colored. Their presence will not particularly change the hue of the pigment. Furthermore, the present 6,13-dihydroquinacridones derivatives are non planar molecules. Based on the state of the art it is unexpected that non planar molecules can act as particle growth inhibitors and crystal phase directors for pigment crystals composed of planar organic pigment molecules. Thus, the inventive compounds allow the manufacturer to produce high performance, high chroma organic pigments in an economical and environmentally friendly manner and therefore, are of extreme commercial importance.
DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT
The present invention relates to novel compounds of formula I:
(MO
3
S)
m
—Q—[CH
2
—(X)—(Y)
n
]
o
(I)
wherein Q represents a 6,13-dihydroquinacridone moiety of formula II:
wherein A and B each independently represent a substituent selected from H, F, Cl, C
1
-C
3
alkyl and C
1
-C
3
alkoxy. Preferably, substituents A and B each represent hydrogen.
M of formula I represents a metal cation, quaternary N cation or hydrogen, X represents an aromatic group or a cyclo hetero aliphatic group with at least one 5 or 6 atom ring or a hetero aromatic group with at least one 5 or 6 atom ring and which is not a phthalimido group; Y is a sulfonic or carboxylic acid or salt thereof, m and n independent of one of the other each are numbers from zero to 2.5, and o is a number from zero to 4, wherein m and o are not zero simultaneously.
The present invention is further directed to a process for the preparation of compounds of formula (I) and to the use thereof.
Preferably, m in formula I represents a number from zero to 2 and most preferably zero to 1; n represents preferably a number from zero to 2 and most preferably from zero to 1.2, and o represents preferably a number from zero to 2 and most preferably from zero to 1.5, wherein m and o are not zero simultaneously. The values for m, n and o are determined by analytical methods like mass spectrometry such as LCMS, GCMS or the matrix-assisted laser desorption ionization technique (MALDI).
The metal cation M of formula I is preferably sodium, potassium, calcium, magnesium or aluminum, and the quaternary N cation of formula 1 is an ammonium or an alkyl ammonium group.
Typically, the group X of the inventive compound of formula I is an aromatic group with a 5 carbon or a 6 carbon ring or a polycyclic group containing two to six fused 5 carbon and/or 6 carbon rings; a cyclo-hetero aliphatic group including at least one 5 or 6 atom ring or fused 5 and/or 6 atom rings, or a hetero aromatic group which is not a phthalimido group, containing a 5 or 6 atom ring or fused 5 and/or 6 atom rings, and in which there are 1 to 4 hetero atoms of N, S and/or O.
Suitable aromatic groups include, for example, phenylene, naphthalene, acenaphthylene, anthracene, phenanthrene, naphthacene, chrysene, pyrene or perylene. Preferably the aromatic group is phenylene, naphthalene, anthracene or pyrene, and most preferably the aromatic group is phenylene or naphthalene.
Cyclo-hetero aliphatic groups are, for example, pyrrolidine, imidazolidine, piperidine, piperazine or morpholine.
Appropriate hetero aromatic groups are, for instance, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, quinoline, isoquinoline, carbazole, phenothiazine, benzimidazolone, benzothiazole, pyrrolo, imidazole or pyrazole.
The above exemplified aromatic, cyclo hetero aliphatic or hetero aromatic groups can optionally be substituted with one or more halogen, oxy, hydroxy, imino, amino and/or C
1
-C
18
alkyl groups, preferably C
1
-C
3
alkyl or C
1
-C
3
alkoxy groups.
Examples of the large number of such substituted cyclo hetero aliphatic or hetero aromatic groups are, for instance, toluene, ortho-, meta- or para-xylene, chlorobenzene, 1- or 2-methylnaphthalene or anthraquinone, barbituric acid, melamine, 1,3,7-trimethylxanthin, hydantoin, 2-methylbenzimidazole, 2,6,8trihydroxypurine, 1,8-naphtosultam, o-benzoic acid sulfimide or 2,4-dihydroxyprimidine.
Commonly, the group Y is a carboxylic acid or a sulfonic acid group. Most preferably the group Y is a free sulfonic acid or a sodium, potassium, magnesium, calcium, aluminum, quaternary ammonium or alkyl ammonium salt thereof.
A further embodiment, as described more fully below, of the present invention is a process for the preparation of compoun
Aulakh Charanjit S.
Ciba Specialty Chemicals Corporation
Crichton David R.
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