Anthraquinone colorants containing copolymerizable vinyl groups

Details Anthraquinone colorants containing copolymerizable vinyl groups Anthraquinone colorants containing copolymerizable vinyl groups

2001-11-13

2003-10-07

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...

C522S018000, C522S028000, C522S016000, C522S026000, C522S096000, C522S103000, C522S107000, C522S181000, C522S182000, C552S236000, C552S237000, C526S328000, C526S328500, C526S284000

Reexamination Certificate

active

06630521

ABSTRACT:

FIELD OF THE INVENTION
This invention pertains to certain thermally-stable, red, anthraquinone colorants which contain one or more ethylenically-unsaturated (vinyl), photopolymerizable radicals which may be copolymewrized (or cured) with ethylenically-unsaturated monomers to produce colored compositions such as colored acrylic polymers, e.g., polymers produced from acrylate and methacrylate esters, colored polystyrenes, and similar colored polymeric materials derived from other ethylenically-unsaturated monomers. The compounds possess good fastness (stability) to ultraviolet (UV) light, good solubility in vinyl monomers, good color strength and thermal stability. The invention also 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 colorant 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 thermally-stable, photopolymerizable dye or colorant compounds having Formula I:
wherein R is hydrogen or methyl, n is 2-3 and Q is a photopolymerizable group selected from organic radicals 1-9:
—COC(R
1
)═CH—R
2
,  1
—CONHCOC(R
1
)═CH—R
2
,  2
—CONH-C
1
-C
6
-alkylene OCOC(R
1
)═CH—R
2
,  3
wherein
R
1
is selected from hydrogen or C
1
-C
6
-alkyl;
R
2
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
1
-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 or 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; and 2- and 3-furyl substituted with C
1
-C
6
-alkyl;
R
3
and R
4
are independently selected from hydrogen, C
1
-C
6
-alkyl, substituted C
1
-C
6
-alkyl and aryl; or R
3
and R
4
may be combined to represent a —(CH
2
—)
3-5
— radical;
R
5
is selected from 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; and
R
6
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
The thermally-stable, photopolymerizable colorant compounds having Formula I constitutes the first embodiment of the present invention. 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 groups consisting of hydroxy, halogen, cyano, aryl, aryloxy, arylthio, C
1
-C
6
-alkylthio, C
3
-C
8
-cycloalkyl, C
2
-C
6
-alkanoyloxy and —(—O—R
7
—)
p
—R
8
, wherein R
7
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; and R
8
is selected from the group consisting of hydrogen, C
1
-C
6
-alkoxy, halogen 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 term “C
1
-C
6
-alkylene” is used to denote a straight- or branched-chain, divalent, hydrocarbon radical containing one to six carbon atoms which may be optionally substituted with one or two groups selected from C
1
-C
6
-alkoxy, C
2
-C
6
-alkanoyloxy, hydroxy, aryl and halogen. The terms “C
1
-C
6
-alkoxy”, “C
2
-C
6
-alkoxycarbonyl” and “C
2
-C
6
-alkanoyloxy” are used to denote radicals corresponding to the structures —OR
9
, —CO
2
R
9
, and —OCOR
9
, respectively, wherein R
9
is C
1
-C
6
-alkyl or substituted C
1
-C
6
-alkyl. The term “C
3
-C
8
-alkenyl” is used to denote an aliphatic hydrocarbon radical containing at least one double bond and having three to eight carbon atoms.
The term “C
3
-C
8
-cycloalkyl” is used to denote a saturated, carbocyclic, hydrocarbon radical having three to eight carbon atoms, optionally substituted with at least one C
1
-C
6
-alkyl group. The term “halogen” is used to denote fluorine, chlorine, bromine and iodine. The term “aryl” is used to denote phenyl and phenyl substituted with one to three substituents selected from C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkoxycarbonyl and halogen.
The vinyl functionalized red colorants of Formula I are prepared by reacting the intermediate diol colorants of Formula II with acylating agents 1′-9′:
CICOC(R
1
)═CH—R
2
ORO[COC(R
1
)═CH—R
2
]
2
,  1′
 O═C═N—COC(R
1
)═CH—R
2
,  2′
O═C═N—C
1
-C
6
alkylene OCOC(R
1
)═CH—R
2
,  3′
wherein R
1
, R
2
, R
3
, R
4
, and R
6
are as defined previously. Q preferably is a group having the formula —COC(R
1
)═CH
2
or
wherein R
1
is hydrogen or methyl.
Intermediate diol compounds having formula II preferably are prepared by reacting either 1,5-dichloro- or 1,8-dichloroanthraquinone with intermediate amino-et

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