Light-absorbing polyurethane compositions and thermoplastic polymers colored therewith
AssigneeEastman Kodak Company
InventorsJames J. Krutak, Max A. Weaver, William W. Parham, Wayne P. Pruett
Life of this patent
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Abstract
Provided are novel light-absorbing polyurethane compositions and blends of said polyurethane compositions with other thermoplastic polymers. Also provided are shaped or formed articles comprised of the light-absorbing polyurethane compositions and light-absorbing thermoplastic polymer blends.
Claims33
A light-absorbing polyurethane composition comprising repeating units of Formula (I) ##STR498## wherein R is a divalent radical selected from C.sub.2 -C.sub.10 -alkylene, C.sub.3 -C.sub.8 -cycloalkylene, arylene, C.sub.1 -C.sub.4 -alkylene-arylene-C.sub.1 -C.sub.4 -alkylene, C.sub.1 -C.sub.4 -alkylene-C.sub.3 -C.sub.8 -cycloalkylene-C.sub.1 -C.sub.4 -alkylene or C.sub.1 -C.sub.4 -alkylene-1,2,3,4,5,6,7-octahydronaphthalene-2,6-diyl-C.sub.1 -C.sub.4 -alkylene, and such radicals substitued by one or more groups selected from C.sub.1 -C.sub.4 alkoxy, halogen, aryl, cyano, C.sub.1 -C.sub.4 alkanoyloxy, C.sub.1 -C.sub.4 alkoxycarbonyl, or hydroxy;
- R.sup.1 is a divalent organic radical comprised of about 1 to about 75 mole percent of the residue of one or more light-absorbing organic diols,
- wherein the light-absorbing diol is selected from the following chromophoric types:
- azo, metallized azo, disazo, methine, or arylidene, polymethine, azo-methine, anthraquinone, azamethine, anthrapyridone (3H-dibenz [f,ij] isoquinoline-2,7-dione, anthrapyridine (7H-dibenz [f,ij] isoquinoline-7-one), phthaloylphenothiazine (14H-naphtho [2,3-a] phenothiazine-8,13-dione, benzanthrone (7H(de)anthracene-7-one), anthrapyrimidine (7H-benzo [e] perimidine-7-one), anthrapyrazole, anthraisothiazole, triphenodioxazine, thiaxanthene-9-one, flourindine (5, 12-dihydroquinoxaline [2,3-b] phenazine), quinophthalone, phthalocyanine, naphthalocyanine, nickel dithiolenes, coumarin (2H-1-benzopyran-2-one), coumarin imine (2H-1-benzopyran-2-imine), indophenol, perinone, nitroarylamine, benzodifuran, phthaloylphenoxazine (14H -naphtho[2,3-a]phenoxazine-8,13-dione), phthaloylacridone (13H-naphtho[2,3-c] acridine 5,8,14-trione), anthraquinonethioxanthone (8H-naphtho[2,3-c]thioxanthene-5,8,13-trione), anthrapyridazone, naphtho[1',2',3':4,5]quino[2,1-b] quinazoline-5,10-dione, 1H-anthra(2,1-b)(1, 4) thiazin-7,12-dione, indigo, thioindigo, xanthene, acridine, azine, oxazine, 1,4- and 1,5-naphthoquinones, pyromellitic acid diimide, naphthalene-1,4,5,8-tetracarboxylic acid diimide, 3,4,9,10-perylenetetracarboxylic acid diimide, naphthoquinone, diminoisoindoline, naphthopyran (3H-naphtho[2,1-b]pyran-3-ones and 3-imines) and aminonaphthalimide;
- wherein the hydroxy groups of said diols are bonded via alkylene moieties to the remainder of the light-absorbing organic compound, with any remainder of R.sup.1 comprised of the residue of organic diols of the formula HO--R.sup.2 --OH;
- wherein R.sup.2 is a divalent radical selected from C.sub.2 -C.sub.18 alkylene, C.sub.3 -C.sub.8 -cycloalkylene, C.sub.1 -C.sub.4 alkylene-1,2,3,4,5,6,7,8-octahydronaphthalen-2,6-diyl-C.sub.1 -C.sub.4 alkylene, C.sub.1 -C.sub.4 -alkylene-C.sub.3 -C.sub.8 -cycloalkylene-C.sub.1 -C.sub.4 -alkylene, C.sub.1 -C.sub.4 alkylene-arylene-C.sub.1 -C.sub.4 -alkylene, C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkylene-S--C.sub.2 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene;
- and
- n is equal to or greater than 2.
A light-absorbing polyurethane composition comprising repeating units for Formula (I) ##STR499## wherein R is a divalent radical selected from C.sub.2 -C.sub.10 -alkylene, C.sub.3 -C.sub.8 -cycloalkylene, arylene, C.sub.1 -C.sub.4 -alkylene-arylene-C.sub.1 -C.sub.4 -alkylene, C.sub.1 -C.sub.4 -alkylene-C.sub.3 -C.sub.8 -cycloalkylene-C.sub.1 -C.sub.4 -alkylene or C.sub.1 -C.sub.4 -alkylene-1,2,3,4,5,6,7-octahydronaphthalene-2,6-diyl-C.sub.1 -C.sub.4 -alkylene, and such radicals substitued by one or more groups selected from C.sub.1 -C.sub.4 alkoxy, halogen aryl, cyano, C.sub.1 -C.sub.4 alkanoyloxy, C.sub.1 -C.sub.4 alkoxycarbonyl, or hydroxy;
- R.sup.1 is a divalent organic radical comprised of about 5 to about 50 mole percent of the residue of one or more light-absorbing organic diols,
- wherein the light-absorbing diol is selected from the following chromophoric types:
- azo, metallized azo, disazo, methine, or arylidene, polymethine, azo-methine, anthraquinone, azamethine, anthrapyridone (3H-dibenz [f,ij] isoquinoline-2,7-dione, anthrapyridine (7H-dibenz [f,ij] isoquinoline-7-one), phthaloylphenothiazine (14H-naphtho [2,3-a] phenothiazine-8,13-dione, benzanthrone (7H(de)anthracene-7-one), anthrapyrimidine (7H-benzo [e] perimidine-7-one), anthrapyrazole, anthraisothiazole, triphenodioxazine, thiaxanthene-9-one, flourindine (5, 12-dihydroquinoxaline [2,3-b] phenazine), quinophthalone, phthalocyanine, naphthalocyanine, nickel dithiolenes, coumarin (2H-1-benzopyran-2-one), coumarin imine (2H-1-benzopyran-2-imine), indophenol, perinone, nitroarylamine, benzodifuran, phthaloylphenoxazine (14H -naphtho[2,3-a]phenoxazine-8,13-dione), phthaloylacridone (13H-naphtho[2,3-c] acridine 5,8,14-trione), anthraquinonethioxanthone (8H-naphtho[2,3-c]thioxanthene-5,8,13-trione), anthrapyridazone, naphtho[1',2',3':4,5]quino[2,1-b] quinazoline-5,10-dione, 1H-anthra(2,1-b)(1, 4) thiazin-7,12-dione, indigo, thioindigo, xanthene, acridine, azine, oxazine, 1,4- and 1,5-naphthoquinones, pyromellitic acid diimide, naphthalene-1,4,5,8-tetracarboxylic acid diimide, 3,4,9,10-perylenetetracarboxylic acid diimide, naphthoquinone, diminoisoindoline, naphthopyran (3H-naphtho[2,1-b]pyran-3-ones and 3-imines) and aminonaphthalimide;
- wherein the hydroxy groups of said diols are bonded via alkylene moieties to the remainder of the light-absorbing organic compound, with any remainder of R.sup.1 comprised of the residue of organic diols of the formula HO--R.sup.2 --OH;
- wherein R.sup.2 is a divalent radical selected from C.sub.2 -C.sub.18 alkylene, C.sub.3 -C.sub.8 -cycloalkylene, C.sub.1 -C.sub.4 alkylene-1,2,3,4,5,6,7,8-octahydronaphthalen-2,6-diyl-C.sub.1 -C.sub.4 alkylene, C.sub.1 -C.sub.4 -alkylene-C.sub.3 -C.sub.8 -cycloalkylene-C.sub.1 -C.sub.4 -alkylene, C.sub.1 -C.sub.4 alkylene-arylene-C.sub.1 -C.sub.4 -alkylene, C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkylene-S--C.sub.2 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene;
- and
- n is equal to or greater than 2.
- wherein the hydroxy groups of said diols are bonded via alkylene moieties to the remainder of the light-absorbing organic compound, with any remainder of R.sup.1 comprised of the residue of organic diols of the formula HO--R.sup.2 --OH;
- wherein
- R.sup.2 is a divalent radical selected from C.sub.2 -C.sub.18 alkylene, C.sub.3 -C.sub.8 -cycloalkylene, C.sub.1 -C.sub.4 alkylene-1,2,3,4,5,6,7,8-octahydronaphthalen-2,6-diyl-C.sub.1 -C.sub.4 alkylene, C.sub.1 -C.sub.4 -alkylene-C.sub.3 -C.sub.8 -cycloalkylene-C.sub.1 -C.sub.4 -alkylene, C.sub.1 -C.sub.4 alkylene-arylene-C.sub.1 -C.sub.4 -alkylene, C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkylene-S--C.sub.2 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene-O--C.sub.2 -C.sub.4 alkylene;
- and
- n is equal to or greater than 2.
Dependencies are inferred from the claim text.