Thermally stable, anthraquinone colorants containing...

Details Thermally stable, anthraquinone colorants containing... Thermally stable, anthraquinone colorants containing...

2003-11-21

2004-09-07

Badio, Barbara P. (Department: 1616)

Organic compounds -- part of the class 532-570 series

Organic compounds

Polycyclo ring system containing anthracene configured ring...

C552S235000, C008S675000

Reexamination Certificate

active

06787658

ABSTRACT:

FIELD OF THE INVENTION
This invention pertains to certain thermally-stable, anthraquinone colorant compounds (dyes) which contain one or more vinyl groups which render the compounds copolymerizable with reactive vinyl monomers to produce colored, polymeric compositions such as acrylate and methacrylate polymeric materials. The compounds possess good fastness (stability) to ultraviolet (UV) light, good solubility in vinyl monomers, good color strength and excellent thermal stability. The present invention includes acrylic polymeric materials, i.e., polymers derived from acrylic acid esters, methacrylic acid esters and/or other copolymerizable vinyl compounds, having copolymerized therein one or more of the dye compounds of the present invention.
BACKGROUND AND PRIOR ART
It is known (J.S.D.C., April 1977, pp 114-125) to produce colored polymeric materials by combining a reactive polymer such terepolymers having epoxy groups or polyacryloyl chloride with anthraquinone dyes containing nucleophilic reactive groups such as amino or hydroxy groups; to graft acryloylaminoanthraquinone dyes to the backbone of vinyl or divinyl polymers; and to polymerize anthraquinone dyes containing certain olefinic groups to produce polymeric dyes/pigments. U.S. Pat. No. 4,115,056 describes the preparation of blue, substituted 1,4-diaminoanthraquinone dyes containing one acryloyloxy group and and the use of the dyes in coloring various fibers, especially polyamide fibers. U.S. Pat. No. 4,943,617 discloses liquid crystalline copolymers containing certain blue, substituted 1,5-diamino-4,8-dihydroxyanthraquinone dyes containing an olefinic group copolymerized therein to provide liquid crystal copolymers having high dichromism. U.S. Pat. No. 5,055,602 describes the preparation of certain substituted 1,4-diaminoanthraquinone dyes containing polymerizable acryloyl and methacryloyl groups and their use in coloring polyacrylate contact lens materials by copolymerizing.
U.S. Pat. No. 5,362,812 discloses the conversion of a variety of dye classes, including anthraquinones, into polymeric dyes by (a) polymerizing 2-alkenylazlactones and reacting the polymer with dyes containing nucleophilic groups and by (b) reacting a nucleophilic dye with an alkenylazlactone and then polymerizing the free radically polymerizable dyes thus produced. The polymeric dyes are reported to be useful for photoresist systems and for colorproofing. U.S. Pat. No. 5,367,039 discloses a process for preparing colored vinyl polymers suitable for inks, paints, toners and the like by emulsion polymerization of a vinyl monomer with reactive anthraquinone dyes prepared by functionalizing certain anthraquinone dyes with methacryloyl groups.
The preparation of a variety of dyes, including some anthraquinones, which contain photopolymerizable groups and their use for color filters suitable for use in liquid crystal television sets, color copying machines, photosensitive resist resin compositions, and the like are described in U.S. Pat. No. 5,578,419.
BRIEF SUMMARY OF THE INVENTION
One embodiment of the present invention concerns anthraquinone dye or colorant compounds represented by general Formulae I-XXI set forth below. The dyes having Formulae I-VII are blue-cyan colorants, the dyes having Formulae VIII-XVIII are red-magenta colorants, and the dyes having Formulae XIX-XXI are yellow colorants.
wherein:
R is selected from hydrogen or 1-3 groups selected from C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy and halogen;
R
1
is selected from C
1
-C
6
-alkyl, substituted C
1
-C
6
-alkyl, C
3
-C
8
-alkenyl, C
3
-C
8
-cycloalkyl, aryl and —L
1
—Z—Q; R
2
=selected from hydrogen, C
1
-C
6
-alkyl, substituted C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl and aryl;
R
3
and R
4
are independently selected from C
1
-C
6
-alkyl and bromine;
R
5
is selected from C
1
-C
6
-alkyl, substituted C
1
-C
6
alkyl, C
3
-C
8
-cycloalkyl, aryl, heteroaryl, —L
1
—Z—Q,
R
6
is selected from
R
7
is selected from hydrogen, substituted or unsubstituted C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogen, hydroxy, substituted or unsubstituted C
1
-C
6
-alkylthio, sulfamoyl and substituted sulfamoyl;
R
8
is selected from hydrogen and C
1
-C
6
-alkyl;
R
9
is selected from the groups represented by R
1
and —L—Z—Q;
R
10
is selected from hydrogen and halogen;
X is a covalent bond or a divalent linking group selected from —O—, —S—, —SO
2
—, —CO
2
—, —CON(Y)— and —SO
2
N(Y)—, wherein Y is selected from hydrogen, C
1
-C
6
-alkyl, substituted C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-alkenyl, aryl and —L—Z—Q;
X
1
is selected from —O—, —S—, —SO
2
— and —SO
2
N(Y)—;
X
2
is selected from —CO
2
— and —SO
2
N(Y
1
), wherein Y
1
is a group selected from hydrogen, C
1
-C
6
-alkyl, substituted C
1
-C
6
-alkyl, C
3
-C
8
-alkenyl, C
3
-C
8
-cycloalkyl, aryl heteroaryl and —CH
2
-p-C
6
H
4
—C(R
8
)═CH
2
;
X
3
is selected from —CO
2
—, —SO
2
N(Y)—;
X
4
is selected from —CO
2
—, —O— and —SO
2
N(Y
1
)—;
L is a divalent linking group selected from C
1
-C
8
-alkylene, C
1
-C
6
-alkylene-arylene, arylene, C
1
-C
6
-alkylene-arylene-C
1
-C
6
-alkylene, C
3
-C
8
-cycloalkylene, C
1
-C
6
-alkylene-C
3
-C
8
-cycloalkylene-C
1
-C
6
-alkylene, C
1
-C
6
-alkylene-Z
1
-arylene-Z
1
-C
1
-C
6
-alkylene and C
2
-C
6
-alkylene-[-Z
1
-C
2
-C
6
-alkylene-]
n
- wherein Z
1
is selected from —O—, —S— and —SO
2
, and n is 1-3;
L
1
is a divalent linking group selected from C
2
-C
6
-alkylene, C
1
-C
6
-alkylene-C
3
-C
8
-cycloalkylene-C
1
-C
6
-alkylene, C
1
-C
6
-alkylene-arylene, C
3
-C
8
-cycloalkylene, and C
2
-C
6
-alkylene-[-Z
1
-C
2
-C
6
-alkylene-]
n
-;
L
2
is selected from C
2
-C
6
-alkylene, C
1
-C
6
-alkylene-arylene-C
1
-C
6
alkylene and C
1
-C
6
-alkylene-C
3
-C
8
-cycloalkylene-C
1
-C
6
-alkylene;
Z is a divalent group selected from —O—, —S—, —NH—, —N(C
1
-C
6
-alkyl)-, —N(C
3
-C
8
alkenyl)-, —N(C
3
-C
8
cycloalkyl)-, —N(aryl)-, —N(SO
2
C
1
-C
6
-alkyl) and —N(SO
2
aryl)-, provided that when Q is a photopolymerizable optionally substituted maleimide radical, Z represents a covalent bond; Q is an ethylenically-unsaturated, photosensitive polymerizable group; and
m and m
1
each is 0 or 1.
—CONH—C
1
-C
6
-alkylene OCOC(R
11
)—CH═CH—R
12
  IIIa
—CONH—C
1
-C
6
-alkylene OCOC(R
11
)—CH═CH—R
12
  IIIa
The ethylenically-unsaturated, photosensitive copolymerizable groups represented by Q are selected from the following organic radicals:
wherein:
R
11
is selected from hydrogen and C
1
-C
6
-alkyl;
R
12
is selected from hydrogen; C
1
-C
6
-alkyl; phenyl and phenyl substituted with one or more groups selected from C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —N(C
1
-C
6
-alkyl), nitro, cyano, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkanoyloxy and halogen; 1- and 2-naphthyl which may be substituted with C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy; 2- and 3-thienyl which may be substituted with C
1
-C
6
-alkyl or halogen; 2- or 3-furyl which may be substituted with C
1
-C
6
-alkyl;
R
13
and R
14
are selected from hydrogen, C
1
-C
6
-alkyl, substituted C
1
-C
6
-alkyl, aryl or may be combined to represent a —[—CH
2
—]
3-5
— radical;
R
15
is selected from hydrogen, C
1
-C
6
-alkyl, substituted C
1
-C
6
-alkyl, C
3
-C
8
-alkenyl, C
3
-C
8
-cycloalkyl and aryl;
R
16
is selected from hydrogen, C
1
-C
6
-alkyl and aryl.
The term “C
1
-C
6
-alkyl” is used herein to denote a straight or branched chain, saturated, aliphatic hydrocarbon radical containing one to six carbon atoms. The term “substituted C
1
-C
6
-alkyl” is used to denote a C
1
-C
6
-alkyl group substituted with one or more groups, preferably one to three groups, selected from the group consisting of hydroxy, halogen, cyano, aryl, aryloxy, arylthio, C
1
-C
6
alkylthio, C
3
-C
8
-cycloalkyl, C
1
-C
6
-alkanoyloxy and —[—O—R
17
—)—R
18
, wherein R
17
is selected from the group consisting of C
1
-C
6
alkylene, C
1
-C
6
-alkylene-arylene, cyclohexylene, arylene, C
1
-C
6
-alkylene-cyclohexylene and C
1
-C
6
-alkylene-cyclohexylene-C
1
-C
6
-alkylene;
R
18
is selected from the group consisting of hydroge

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