Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2000-09-19
2002-08-27
Green, Anthony J. (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S217500, C106S493000, C106S498000, C524S104000, C524S111000
Reexamination Certificate
active
06440206
ABSTRACT:
The present invention relates to a composition comprising
(a) from 1 to 20, preferably from 1 to 10% by weight of a sorbitan ester of the formula I
wherein R
1
and R
2
, independently from each other, stand for C
1
-C
20
alkyl or C
2
-C
20
alkenyl, and
(b) from 99 to 80, preferably from 99 to 90% by weight of a metal or ammonium laked monoazo pigment of formula 11
wherein
R
3
, R
4
, R
5
, R
6
, R
7
and R
8
independently from each other stand for hydrogen, C
1
-C
20
alkyl C
1
-C
20
alkoxy, C
2
-C
20
alkenyl, C
1
-C
20
alkylthiol, C
1
-C
20
alkoxycarbonyl, hydroxyC
1
-C
4
alkoxy, phenyl, benzyl, phenylthio, fluoro, chloro, bromo, iodo, —CN, —NO
2
, —CF
3
, —COR
9
, —COOR
9
, —CONR
9
R
10
, —SO
2
R
9
, —SO
2
NR
9
R
10
, —NR
9
NR
10
in which each R
9
and R
10
are each independently from each other hydrogen, —OH, C
1-4
-alkyl or phenyl, where at least one of R
3
, R
4
, R
5
, R
6
, R
7
and R
8
is either —COOH or —SO
3
H, and M may be NH
4
+
, or a cation of an alkali metal, an alkaline earth metal, such as Na, K, Mg, Ca, Sr, Ba, or a cation of a transition metal such as Mn, Co, Ni, Cu, Fe or Al,
as well as a process for its preparation and its use as well as the use of the sorbitan ester I as an additive to improve color strength and dispersion properties.
WO 9851160 describes a pigment or dyestuff composition comprising 2 to 10% by weight of a pigment or dyestuff, 3 to 30% by weight of a polyoxyethylene sorbitan fatty acid ester, 1 to 10% by weight of another sorbitan fatty acid ester and dispersing agents.
JP-A2 10204243 describes vinylidene chloride-based polymer compositions with improved dispersibility for coloration of polymers comprising the polymer, 30% by weight Pigment Red 208, 2% by weight sorbitan trioleate and other additives.
U.S. Pat. No. 4,177,082 describes nondusting, easily dispersible pigment or dye granules, wherein a pigment is treated with a mixture of hydroxyethylcellulose, an amine, sorbitan tristearate and dicyclohexyl phthalate under elevated temperature, then pH adjusting and finally mixing with a polymer such as polyvinylchloride (“PVC”) or polyethylene (“PE”).
JP-A2 50101427 describes compositions comprising a pigment, PVC, diphenol derivatives and polyethylene glycol sorbitan monolaurate. According to this document the addition of bisphenol A is essential for a good dispersibility.
However, the dispersibility and color strength of the abovementioned compositions is not good enough for todays demands. Further, in all cases the pigments and the additives, inter alia sorbitan fatty acid esters, are mixed together at the same time. In addition, compositions consisting of just a pigment and sorbitan fatty acid esters are not known, rather, always additional additives have to be used, too.
Hence, the object of this invention was to provide compositions consisting of a metal or ammonium laked monoazo pigments with improved color strength and dispersion properties. Especially, an object was to improve the color strength and dispersion properties of Pigment Yellow 191:1 by the addition of an appropriate additive. In addition, the inventive composition should be used in food contact applications.
Accordingly, the above defined composition was found.
Metal or ammonium laked monoazo pigments such as Pigment Yellow 61, Pigment Yellow 62:1, Pigment Yellow 100, Pigment Yellow 133, Pigment Yellow 168, Pigment Yellow 169, Pigment Yellow 183 (e.g. Paliotol®Yellow K-2270 from BASF), Pigment Yellow 190 (e.g. PV Fast yellow HGR from Hoechst), and Pigment Yellow 191:1 are well known to the person skilled in the art, e.g. from Herbst/Hunger, “Industrielle Organische Pigmente”, 2nd edition, VCH 1995, p. 240-243.
A preferred embodiment of the present invention relates to a composition consisting essentially of
(a) from 1 to 10% by weight of sorbitan ester I, preferably wherein R
1
=R
2
=C
8
-C
20
alkyl or C
8
-C20alkenyl, and
(b) from 99 to 90% by weight of compound II or compound III, preferably wherein R
3
, R
4
, R
5
, R
6
, R
7
and R
8
independently from each other stand for hydrogen, methyl, methoxy, fluoro, chloro, bromo, iodo, —NO
2
, —CF
3
, —COOR
9
, —SO
2
R
9
, in which R
9
preferably stands for hydrogen or —OH, and more preferred, wherein at least one of R
3
, R
4
, R
5
, R
6
, R
7
and R
8
independently from each other, stand for —COOH or —SO
3
H, and wherein M stands for ammonium, or a cation of Ca, Sr or Al.
Another preferred embodiment of the instant invention relates to a composition consisting essentially of
(a) from 1 to 10% by weight of a sorbitan ester I, wherein R
1
stands for n-undecyl, and
(b) from 90 to 99% by weight of a laked monoazo derivative of formula IIIa
A particularly preferred embodiment relates to a composition consisting of
(a) 95% by weight of monoazo derivative IIIa and
(b) 5% by weight of sorbitan monolaurate.
A further particularly preferred embodiment relates to a composition consisting of
(a) 95% by weight of
(b) 5% by weight of sorbitan monostearate.
C
1
-C
20
alkyl stands for methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, preferably C
8
-C
20
alkyl such as n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl;
C
1
-C
4
alkyl stands for methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.-butyl;
C
1
-C
20
alkoxy stands for methoxy, ethoxy, n-, i-propoxy, n-, i-, sec.-, tert.-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, n-tridecoxy, n-tetradecoxy, n-pentadecoxy, n-hexadecoxy, n-heptadecoxy, n-octadecoxy, n-nonadecoxy, n-eicosoxy;
C
2
-C
20
alkenyl stands for ethenyl, n-, i-propenyl, n-, i-, sec.-, tert.-butenyl, n-pentenyl, n-hexenyl, n-heptenyl, n-octenyl, n-nonenyl, n-decenyl, n-undecenyl, n-dodecenyl, n-tridecenyl, n-tetradecenyl, n-pentadecenyl, n-hexadecenyl, n-heptadecenyl, n-octadecenyl, n-nonadecenyl, n-eicosenyl;
C
1
-C
20
alkylthiol stands for methylthio, ethylthio, n-, i-propylthio, n-, i-, sec.-, tert.-butylthio, n-pentylthio, n-hexylthio, n-heptylthio, n-octylthio, n-nonylthio, n-decylthio, n-undecylthio, n-dodecylthio, n-tridecylthio, n-tetradecylthio, n-pentadecylthio, n-hexadecylthio, n-heptadecylthio, n-octadecylthio, n-nonadecylthio, n-eicosylthio;
C
1
-C
20
alkoxycarbonyl stands for methoxycarbonyl, ethoxycarbonyl, n-, i-propoxycarbonyl, n-, i-, sec.-, tert.-butoxycarbonyl, n-pentoxycarbonyl, n-hexoxycarbonyl, n-heptoxycarbonyl, n-octoxycarbonyl, n-nonoxycarbonyl, n-decoxycarbonyl, n-undecoxycarbonyl, n-dodecoxycarbonyl, n-tridecoxycarbonyl, n-tetradecoxycarbonyl, n-pentadecoxycarbonyl, n-hexadecoxycarbonyl, n-heptadecoxycarbonyl, n-octadecoxycarbonyl, n-nonadecoxycarbonyl, n-eicosoxycarbonyl;
hydroxyC
1
-C
4
alkoxy hydroxymethoxy, hydroxyethoxy, hydroxy-n-, -i-propoxy, hydroxy-n-, -i-, -sec.-, -tert.-butoxy;
M may be NH
4
+
, or a cation of an alkali metal, an alkaline earth metal, such as Na, K, Mg, Ca, Sr, Ba, or a cation of a transition metal such as Mn, Co, Ni, Cu, Fe or from Al.
Another embodiment of the present invention is directed to a process for the preparation of the inventive compositions, wherein
(a) a mixture of a pigment of formula II or III, sorbitan ester I and water is heated to a temperature in the range of 70 to 100° C., preferably to reflux, for 1 to 60 minutes, then
(b) cooling the obtained mixture to a temperature in the range of from 30 to 70° C., then
(c) separation of the solid parts from the liquid parts,
(d) drying the obtained solid parts at a temperature in the range of from 50 to 90° C., and
(e) optionally sieving the thus dried pigment composition to the desired particle size.
Another preferred embodiment relates to a process for the preparation of the inventive composition characterized in
(a) reacting an amino compound of formula IV
with sodium nitrite,
(b) reacting the thus obtained diazo componen
Chisholm Greig
Hay Barry William
Ciba Specialty Chemicals Corporation
Crichton David R.
Green Anthony J.
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