Colorants containing copolymerizable vinyl groups and...

Details Colorants containing copolymerizable vinyl groups and... Colorants containing copolymerizable vinyl groups and...

2001-08-01

2003-09-16

Berman, Susan W. (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Compositions to be polymerized by wave energy wherein said...

C522S103000, C522S107000, C522S167000, C522S173000, C564S080000, C564S082000, C564S084000, C564S088000, C564S095000, C564S098000, C564S099000, C526S328000, C526S328500, C552S234000, C552S236000, C552S208000

Reexamination Certificate

active

06620858

ABSTRACT:

FIELD OF THE INVENTION
This invention pertains to thermally-stable, colored, photopolymerizable compounds containing a vinyl group which are capable of being copolymerized with reactive vinyl monomers to produce colored compositions such as polyacrylates, polymethacrylates, polystyrene, etc. The compounds exhibit good thermal stability, fastness (stability) to UV-light, good solubility in the reactive monomers and good color strength.
BACKGROUND AND PRIOR ART
It is known (J.S.D.C., Apr. 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 thermally-stable, photopolymerizable dye or colorant compounds having having Formula I:
wherein
A is a mono-, di-, tri- or tetravalent chromophore;
R
1
is selected from hydrogen, C
1
-C
6
alkyl, substituted C
1
-C
6
alkyl, C
3-
C
8
cycloalkyl, aryl and —R
2
—OQ;
R
2
is selected from C
2
-C
8
alkylene, arylene, C
3
-C
8
cycloalkylene, arylene-C
1
-C
6
alkylene, arylene-oxy-C
1
-C
6
alkylene, arylenethio-C
1
-C
6
alkylene, 1,4-cyclohexylenedimethylene and —(—CH
2
CH
2
O)
m
—CH
2
CH
2
—;
m is 1-3;
n is 1-4;
Q is an ethylenically-unsaturated, photopolymerizable group selected from the following organic radicals:
wherein
R
3
is selected from hydrogen or C
1
-C
6
alkyl;
R
4
is selected from hydrogen, C
1
-C
6
alkyl; phenyl; 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)
2
, nitro, cyano, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkanoyloxy and halogen; 1- and 2-naphthyl; 1- and 2-naphthyl substituted with C
1
-C
6
alkyl and C
1
-C
6
alkoxy; 2- and 3-thienyl; 2- and 3-thienyl substituted with C
1
-C
6
alkyl or halogen; 2- and 3-furyl; 2- and 3-furyl substituted with C
1
-C
6
alkyl;
R
5
and R
6
are independently 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
7
is hydrogen or a group selected from C
1
-C
6
alkyl, substituted C
1
-C
6
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
cycloalkyl and aryl;
R
9
is selected from hydrogen, C
1
-C
6
alkyl and aryl.
A second embodiment of the present invention pertains to a coating composition comprising (i) one or more polymerizable vinyl compounds, (ii) one or more of the thermally-stable, photopolymerizable dye or colorant compounds of Formula I, and (iii) a photoinitiator. A third embodiment of the present invention pertains to a polymeric composition, typically a coating, comprising a polymer of one or more acrylic acid esters, one or more methacrylic acid esters and/or other polymerizable vinyl compounds, having copolymerized therein one or more of the dye compounds of Formula I.
DETAILED DESCRIPTION OF THE INVENTION
In formula I, A represents a mono-, di-, tri- or tetravalent residue of a chromophore, i.e., a colored compound. Examples of the chromophoric residues which A may represent include anthraquinone, anthrapyridone (3H-dibenz-[f, ij]-isoquinoline-2,7-dione), anthrapyrimidine (7H-benzo-[e]-perimidine-7-one), anthrapyridine (7H-dibenz-[f, ij]-isoquinoline-7-one), anthrapyrazole, anthraisothiazole, 14H-naptho[2,3-a]-phenothiazine-8,13-dione (phthaloylphenothiazine), phthalocyanine, metal phthalocyanine, methine, bis-methine, perinone, coumarin, quinophthalone, 3-aryl-2,5-dioxypyrroline, and 3-aryl-5-dicyanomethylene-2-oxypyrroline.
The terms “C
1
-C
6
-alkyl” and “C
1
-C
8
-alkyl” are used herein to denote a straight or branched chain saturated aliphatic hydrocarbon radical containing one to six or one to eight 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
2
-C
6
-alkanoyloxy and —(—OR
9
—)
p
—R
10
wherein R
9
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
10
is selected from the group consisting of hydrogen, hydroxy, carboxy, C
2
-C
6
-alkanoyloxy, C
2
-C
6
-alkoxycarbonyl, aryl and C
3
-C
8
-cycloalkyl; and p is 1, 2, or 3.
The terms “C
1
-C
6
-alkylene”, “C
2
-C
6
-alkylene” and “C
2
-C
8
alkylene” are used to denote straight or branched chain divalent aliphatic hydrocarbon radicals containing one to six, two to six, and two to eight carbons, respectively, which optionally may be substituted with one to three groups selected from C
1
-C
6
-alkoxy, C
2
-C
6
-alkoxycarbonyl, C
2
-C
6
-alkanoyloxy, hydroxy, aryl and halogen. The term “C
3
-C
8
-alkenyl” is used to denote an aliphatic hydrocarbon radical containing at least one double bond. The term “C
3
-C
8
-alkynyl” is used to denote an aliphatic hydrocarbon radical containing at least one triple bond and three to eight carbon atoms. The term “C
3
-C
8
-cycloalkyl” is used to denote a saturated cyclic hydrocarbon radical having three to eight carbon optionally substituted with one to three C
1
-C
6
-alkyl group(s). The term “C
3
-C
8
-cycloalkylene” is used to denote a cyclic divalent hydrocarbon radical which contains three to eight carbon atoms, preferably five or six carbons.
The term “aryl” as used herein denotes phenyl and phenyl substituted with one to three substituents selected from C
1
-C
6
-alkyl, substituted C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogen, carboxy, cyano, C
2
-C
6
-alkanoyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfonyl, trifluoromethyl, hydroxy, optionally substituted sulfamoyl, C
2
-C
6
-alkoxycarbonyl, C
2
-C
6
-alkanoylamino and —O—R
11
, S—R
11
, —SO
2
—R
11
, —NHSO
2
R
11
and —NHCO
2
R
11
, wherein R
11
is phenyl or phenyl substituted with one to three groups selected from C
1
-C
6
-alkyl, C
1
-C
6
-

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