Silicone polyurethane copolymers containing oxygen sensitive phosphorescent dye compounds
First Claim
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1. A silicone polyurethane copolymer containing a phosphorescent dye compound wherein the copolymer is represented by the formula:
- ##STR7## wherein n is an integer ranging from 1 to about 30, and y, z, and w are integers ranging from 0 to about 40, wherein one of y, z, and w is at least one; and
(a) A is a diamide group having the formula;
space="preserve" listing-type="equation">--COHN--R.sub.1 --NHCO-- wherein R1 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R1 group containing from 1 to about 30 carbon atoms;
(b) B is a silicone block copolymer having the formula;
space="preserve" listing-type="equation">(--XR.sub.3 O).sub.u (Si(R.sub.2).sub.2 O).sub.v (R.sub.3 X--).sub.u wherein R2 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R2 group being the same or different and having from 1 to about 18 carbon atoms;
R3 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R3 group having from 1 to about 18 carbon atoms;
X is selected from the group consisting of oxygen and nitrogen;
u is an integer ranging from about 5 to about 15; and
v is an integer ranging from about 5 to about 50;
(c) D is a chain extender having the formula;
space="preserve" listing-type="equation">--X'"'"'--R.sub.4 --X'"'"'-- wherein R4 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R4 group having from 1 to about 12 carbon atoms; and
X'"'"' is selected from the group consisting of oxygen and nitrogen; and
(d) E is a phosphorescent dye compound having the formula;
##STR8## wherein R5 is a phosphorescent compound selected from the group consisting of porphyrin and compounds selected from the group consisting of porphyrin and compounds containing the basic cyclic tetrapyrrolic ring structure of porphyrin which compound has an absorption spectrum in the region of 400-800 nm, said compound being chelated with a metal ion selected from the group consisting of platinum, palladium, rhodium, and gadolinium, and X'"'"''"'"' is selected from the group consisting of oxygen and nitrogen.
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Abstract
The present invention is directed to silicone polyurethane copolymers containing phosphorescent dye compounds wherein the copolymers are represented by the formula: ##STR1## wherein n is an integer ranging from 1 to about 30, and y, z, and w are integers ranging from 0 to about 40, wherein one of y, z, and w is at least one; and A is a diamide, B is a silicone block copolymer, D is a chain extender, and E is a phosphorescent porphyrin-type compound.
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Citations
12 Claims
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1. A silicone polyurethane copolymer containing a phosphorescent dye compound wherein the copolymer is represented by the formula:
- ##STR7## wherein n is an integer ranging from 1 to about 30, and y, z, and w are integers ranging from 0 to about 40, wherein one of y, z, and w is at least one; and
(a) A is a diamide group having the formula;
space="preserve" listing-type="equation">--COHN--R.sub.1 --NHCO--wherein R1 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R1 group containing from 1 to about 30 carbon atoms; (b) B is a silicone block copolymer having the formula;
space="preserve" listing-type="equation">(--XR.sub.3 O).sub.u (Si(R.sub.2).sub.2 O).sub.v (R.sub.3 X--).sub.uwherein R2 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R2 group being the same or different and having from 1 to about 18 carbon atoms;
R3 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R3 group having from 1 to about 18 carbon atoms;
X is selected from the group consisting of oxygen and nitrogen;
u is an integer ranging from about 5 to about 15; and
v is an integer ranging from about 5 to about 50;(c) D is a chain extender having the formula;
space="preserve" listing-type="equation">--X'"'"'--R.sub.4 --X'"'"'--wherein R4 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R4 group having from 1 to about 12 carbon atoms; and
X'"'"' is selected from the group consisting of oxygen and nitrogen; and(d) E is a phosphorescent dye compound having the formula;
##STR8## wherein R5 is a phosphorescent compound selected from the group consisting of porphyrin and compounds selected from the group consisting of porphyrin and compounds containing the basic cyclic tetrapyrrolic ring structure of porphyrin which compound has an absorption spectrum in the region of 400-800 nm, said compound being chelated with a metal ion selected from the group consisting of platinum, palladium, rhodium, and gadolinium, and X'"'"''"'"' is selected from the group consisting of oxygen and nitrogen. - View Dependent Claims (2, 3, 4, 6, 9, 10, 11)
- ##STR7## wherein n is an integer ranging from 1 to about 30, and y, z, and w are integers ranging from 0 to about 40, wherein one of y, z, and w is at least one; and
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5. The silicone copolymer according to wherein R3 is selected from the group consisting of alkyl groups and aryl groups, each R3 group having from 1 to about 6 carbon atoms.
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7. The silicone copolymer according to wherein R4 is an alkyl group having from 1 to about 6 carbon atoms.
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8. The silicone copolymer according to wherein R5 is selected from the group consisting of platinum tetra(p-aminophenyl)porphine, platinum tetra(p-hydroxyphenyl)porphine, platinum tetra(p-carboxyphenyl)porphine, and mixtures thereof.
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12. A method for preparing a silicone polyurethane copolymer containing a phosphorescent dye compound which comprises the steps of:
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(1) providing the following ingredients; (a) a diisocyanate having the formula;
space="preserve" listing-type="equation">OCN--R.sub.1 --NCOwherein R1 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R1 group containing from 1 to about 30 carbon atoms; (b) a silicone block copolymer having the formula;
space="preserve" listing-type="equation">(HXR.sub.3 O).sub.u (Si(R.sub.2).sub.2 O).sub.v (R.sub.3 XH).sub.uwherein R2 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R2 group being the same or different and having from 1 to about 18 carbon atoms;
R3 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R3 groups having from 1 to about 18 carbon atoms;
X is selected from the group consisting of oxygen and nitrogen;
u is an integer ranging from about 5 to about 15; and
v is an integer ranging from about 5 to about 50;(c) a chain extender having the formula;
space="preserve" listing-type="equation">HX'"'"'--R.sub.4 --XC'"'"'Hwherein R4 is selected from the group consisting of substituted and unsubstituted alkyl groups, cycloalkyl groups, and aryl groups, each R4 group having from 1 to about 12 carbon atoms; and
X'"'"' is selected from the group consisting of oxygen and nitrogen; and(d) a phosphorescent dye compound having the formula;
##STR9## wherein R5 is a phosphorescent compound selected from the group consisting of prophyrin and compounds containing the basic cyclic tetrapyrrolic ring structure of prophyrin which compound has an absorption spectrum, in the region of 400-800 nm, said compound being chelated with a metal ion selected from the group consisting of platinum, palladium, rhodium, and gadolinium, and X'"'"''"'"' is selected from the group consisting of oxygen and nitrogen; and(2) admixing the silicone block copolymer, the chain extender, and the phosphorescent dye compound in a solvent; (3) reacting the diisocyanate from step (1)(a) with the admixture from step (2) to form the silicone polyurethane copolymer containing a phosphorescent dye compound.
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Specification