Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2001-08-27
2002-12-03
Green, Anthony J. (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S493000, C106S499000, C106S031750, C106S031800, C524S190000
Reexamination Certificate
active
06488759
ABSTRACT:
FIELD OF THE INVENTION
The present invention generally relates to monoarylide pigment compositions. In particular, the present invention relates to monoarylide pigments coupled in the presence of hydrocarbyl polyamines which provide pigment compositions having increased tinctorial strength.
BACKGROUND OF THE INVENTION
Azo pigments are a class of colorants that are relatively strong tinctorially and relatively inexpensive. Azo pigments are generally either monoazo or disazo pigments. Azo pigments can also be classified by the type of coupler used (e.g., acetoacetarylide or arylide, pyrazolone, or 2-naphthol). Monoazo pigments made by coupling into an acetoacetarylide are called monoarylide pigments.
Monoarylide pigments generally show good lightfastness/weathering resistance and are particularly useful as coloring agents for paints. One particular use of reddish yellow monoarylide pigments includes replacement for medium chrome yellow pigments in paints used to make traffic stripes. Although monoarylide pigments are relatively strong tinctorially, they are not as tinctorially strong as diarylide pigments. For example, monoarylide yellow C.I. (Colour Index) P.Y. (Pigment Yellow) 65 is not as tinctorially strong as diarylide yellow C.I. P.Y. 83. W. Herbst and K. Hunger,
Industrial Organic Pigments
, Second Edition, VCH, New York, 1997, p. 228, state: “Tinctorially, however, P.Y. 65 is considerably inferior, which precludes its application in printing inks. Opaque varieties of the slightly more greenish diarylide yellow pigment P.Y. 83, for instance, are more than three times as strong as P.Y. 65, yet provide similar lightfastness.”
A patent which describes coupling monoarylide yellow pigments in the presence of monoamine salts, followed by addition of rosin solutions, is German Offenlegungsschrift 2526872 (1976, Ciba-Geigy AG); this process gives pigments with increased dispersibility and transparency in lithographic inks.
Several patents describe coupling diarylide yellow pigments in the presence of amine salts. U.S. Pat. No. 5,672,202 to Stirling et al relates to coupling diarylide yellow C.I. P.Y. 12 in the presence of a long chain aliphatic primary amine and ethylene polyamine, then post-adding (adding after coupling) quaternary ammonium chloride and a long chain aliphatic dipropylenetriamine to improve strength, gloss and transparency. U.S. Pat. No. 5,145,997 to Schwartz et al relates to co-coupling P.Y. 12 with a (acetoacet) derivative of a polyoxyalkylene mono-, di- or tri-amine, which gave gravure inks with less color deterioration than inks containing P.Y. 12 modified with tallowalkyl dipropylenetriamine. U.S. Pat. No. 4,885,033 to Blackburn et al relates to coupling P.Y. 12 in the presence of 2,2′-disulfobenzidine dyes and rosin salts, then mixing it with a P.Y. 13/tallowalkyl propylenediamine mixture to improve rheology and printing properties of inks. European Patent 567,918 (1994, Hoechst AG) relates to coupling P.Y. 12 in the presence of an amide of tallowalkyl propylenediamine and caprolactam along with bis(4-aminocyclohexyl)methane and a long chain aliphatic amine to improve gloss, strength and holdout. European Patent 62,304 (1982, Hoechst AG) relates to coupling diarylide yellows in the presence of a long chain aliphatic amine or a quaternary ammonium chloride phase transfer catalyst, then post-adding a polyethyleneamine to increase strength and gloss. U.S. Pat. No. 4,462,833 to Hays et al relates to post-adding tallowalkyl tripropylenetetramine to P.Y. 12 slurries to increase holdout of publication gravure inks.
SUMMARY OF THE INVENTION
The present invention provides monoarylide pigments with excellent tinctorial strength. Since monoarylide pigments tend to be less expensive and have better lightfastness/weathering resistance than diarylide pigments, increasing the tinctorial strength of monoarylide pigments is a very attractive benefit associated with the present invention.
One aspect of the invention relates to pigment composition containing a monoarylide pigment and a hydrocarbyl polypropyleneamine compound. Another aspect of the invention relates to making an monoarylide pigment involving coupling a substituted or unsubstituted acetoacetanilide with at least one diazotized aromatic amine in a solution containing a hydrocarbyl polypropyleneamine. Yet another aspect of the invention relates to paint, ink, electrostatic toner, powder coating, and paper compositions containing the pigment composition or monoarylide pigment made in accordance with the invention.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to a monoarylide pigment made using one or more hydrocarbyl polypropyleneamine compounds. In this connection, monoarylide pigments in accordance with the present invention are made, in part, by coupling a diazotized aromatic amine with a substituted or unsubstituted acetoacetanilide in the presence of at least one hydrocarbyl polypropyleneamine. Pigment compositions contain the monoarylide pigment and the hydrocarbyl polypropyleneamine. Although not limited thereto, monoarylide pigments in accordance with the present invention typically have yellow and/or orange color.
The pigments of the present invention are made using or pigment compositions of the present invention contain a hydrocarbyl polypropyleneamine having Formula (I):
RNH(CH
2
CH
2
CH
2
NH)
x
H (I)
wherein R is a saturated or unsaturated hydrocarbyl group containing about 10 or more carbon atoms and about 24 or less carbon atoms and x is about 1 or more and about 5 or less. In another embodiment, R is a saturated or unsaturated hydrocarbyl group containing about 12 or more carbon atoms and about 22 or less carbon atoms and x is about 2 or more and about 4 or less. In yet another embodiment, R is a saturated or unsaturated hydrocarbyl group containing about 14 or more carbon atoms and about 20 or less carbon atoms.
As used herein, the term “hydrocarbyl” means that the group being described has predominantly hydrocarbon character within the context of this invention. These include groups that are not only purely hydrocarbon in nature (containing only carbon and hydrogen), but also groups containing substituents or hetero atoms which do not alter the predominantly hydrocarbon character of the group. Such substituents may include halo-, carbonyl-, ester-, ether-, alkoxy-, nitro-, etc. These groups also may contain hetero atoms. Suitable hetero atoms will be apparent to those skilled in the art and include, for example, sulfur, nitrogen and particularly oxygen.
In one embodiment, the hydrocarbyl polypropyleneamine is a saturated alkyl polypropyleneamine, wherein the alkyl group contains about 10 or more carbon atoms and about 24 or less carbon atoms. In another embodiment, the hydrocarbyl polypropyleneamine is an unsaturated alkyl polypropyleneamine, wherein the alkyl group contains about 10 or more carbon atoms and about 24 or less carbon atoms.
General examples of hydrocarbyl polypropyleneamines include stearyl poly(propyleneamine), oleyl poly(propyleneamine), lauryl poly(propyleneamine), decyl poly(propyleneamine), myristyl poly(propyleneamine), palmyl poly(propyleneamine), isodecyl poly(propyleneamine), tallowalkyl poly(propyleneamine), and cocoalkyl poly(propyleneamine).
Specific examples of hydrocarbyl polypropyleneamines include tallowalkyl tetrapropylenepentamine, tallowalkyl tripropylenetetramine, tallowalkyl dipropylenetriamine, cocoalkyl tetrapropylenepentamine, cocoalkyl tripropylenetetramine, cocoalkyl dipropylenetriamine, stearyl tetrapropylenepentamine, stearyl tripropylenetetramine, stearyl dipropylenetriamine, oleyl tetrapropylenepentamine, oleyl tripropylenetetramine, oleyl dipropylenetriamine, lauryl tetrapropylenepentamine, lauryl tripropylenetetramine, lauryl dipropylenetriamine, decyl tetrapropylenepentamine, decyl tripropylenetetramine, decyl dipropylenetriamine, myristyl tetrapropylenepentamine, myristyl tripropylenetetramine, myristyl dipropylenetriamine, palmyl tetrapropylenepentamine, palmyl tripropylenetetramine, palmyl dipropylenetria
Engelhard Corporation
Green Anthony J.
Keller Raymond F.
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