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US5286803A
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Coumarin dyes and side-chain coumarin dye-substituted polymers which exhibit nonlinear optical properties
Assignee: United States Department of the Navy
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Filing: 1990-11-26
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Granted: 1994-02-15
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Expires: 2010-11-26
Abstract
Abstract Coumarin dyes such as alkylaminocoumarincarboxamides which have functional hydroxyl groups or which are chemically attached to vinyl monomers such as methacrylic acid. The dyes which are chemically attached to vinyl monomers can be copolymerized, e.g. with acrylic monomers to produce a coumarin dye-containing polymer. The dyes which have functional hydroxyl groups can be reacted with an existing polymer or copolymer, e.g. a copolymer of styrene and acrylic acid to esterify the acid groups of the polymer to form a coumarin dye-containing polymer. Such coumarin dye-containing polymers are formed into films and fibers which when poled in an electric field yield a film or fiber with nonlinear optical properties.
Inventors
- 👤 Geoffrey Lindsay
- 👤 Ronald A. Henry
- 👤 James M. Hoover
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 07:35
CPC Classifications
C; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; C09; C09B; C09B69/00; C09B69/10; C09B69/109; G; G02; G02F; G02F1/00; G02F1/35; G02F1/355; G02F1/361; G02F1/3615; G02F1/3617
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
127 words
Coumarin dye-containing polymers which are water insoluble, having second-order nonlinear optical properties, which are characterized by a recurring monomeric unit corresponding to the formula: ##STR10## where P is a polymer main chain unit; and, where D is a coumarin dye selected from the group consisting of: ##STR11## where R and R 2 are independently selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, and alkenyl of 1 to 22 carbon atoms; where G is selected from the group consisting of H, --CH 3 , and --CF 3 ; where A and B are independently selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, and the atoms necessary to complete a 6-membered ring; and, where n=2 to 18.
Claim 2
Dependent Claim
127 words
Coumarin dye-containing polymers which are water insoluble, having second-order nonlinear optical properties, which are characterized by a recurring monomeric unit corresponding to the formula: ##STR10## where P is a polymer main chain unit; and, where D is a coumarin dye selected from the group consisting of: ##STR11## where R and R 2 are independently selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, and alkenyl of 1 to 22 carbon atoms; where G is selected from the group consisting of H, --CH 3 , and --CF 3 ; where A and B are independently selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, and the atoms necessary to complete a 6-membered ring; and, where n=2 to 18.
Claim 3
Dependent Claim
24 words
Coumarin dye-containing polymers as defined in claim 1, where P is selected from the group consisting of a styrenic unit and an acrylic funit.
Claim 4
Dependent Claim
14 words
Coumarin dye-containing polymers as defined in claim 1, where P is an acrylic unit.
Claim 5
Dependent Claim
14 words
Coumarin dye-containing polymers as defined in claim 1, where P is a styrenic unit.
Claim 6
Dependent Claim
62 words
Coumarin dye-containing polymers as defined in claim 1, where P is selected from the group consisting of: ##STR12## where R 1 is selected from the group consisting of H or alkyl of 1 to 22 carbon atoms; where R 7 is selected from the group consisting of H and --COOR 1 ; and, where F is --O--, --NH--, or --CH 2 --O--.
Claim 7
Dependent Claim
105 words
Coumarin dye-containing polymers as defined in claim 1, where D is selected from the group consisting of: ##STR13## where R and R 2 are independently selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, and alkenyl of 1 to 22 carbon atoms; where G is selected from the group consisting of H, --CH 3 , and --CF 3 ; where A and B are independently selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, alkenyl of 1 to 22 carbon atoms, and the atoms necesary to complete a 6-membered ring; and, where n=2 to 18.
Claim 8
Dependent Claim
104 words
Coumarin dye-containing polymers as defined in claim 1, further comprising non-coumarin containing main chain units, which can be illustrated by the formula: ##STR14## where R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of alkyl, alkenyl, aryl, substituted aryl, cyano, amide, halogen, alkoxy, or --COOR 8 , where R 8 is is selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, and alkenyl of 1 to 22 carbon atoms; and, where y is at least 3, (x+y+z) ranges from 3 to about 3000, and y/(x+y+z) is 0.10 to 1.0.
Claim 9
Dependent Claim
26 words
Coumarin dye-containing polymers as defined in claim 7, where P is selected from the group consisting of a styrenic functional unit and an acrylate functional unit.
Claim 10
Dependent Claim
12 words
Coumarin dye-containing polymers as defined in claim 7, where n=2 to 6.
Claim 11
Dependent Claim
105 words
Coumarin dye-containing polymers as defined in claim 7, where D is selected from the group consisting of: ##STR15## where R and R 2 are independently selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, and alkenyl of 1 to 22 carbon atoms: where A and B are independently selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, alkenyl of 1 to 22 carbon atoms, and the atoms necessary to complete a 6-membered ring; where G is selected from the group consisting of H, --CH 3 , and --CF 3 ; and, where n=2 to 18.
Claim 12
Dependent Claim
27 words
Coumarin dye-containing polymers as defined in claim 10 wherein R is H; R 1 and R 3 are methyl; R 4 is --COOCH 3 ; and, z=0.
Claim 13
Dependent Claim
27 words
Coumarin dye-containing polymers as defined in claim 10, where R is H, R 1 and R 3 are CH 3 , R 4 is aryl, and z=0.
Claim 14
Dependent Claim
10 words
Coumarin dye-containing polymers as defined in claim 12, where n=2.
Claim 15
Dependent Claim
34 words
Coumarin dye-containing polymers as defined in claim 10, where R 3 is H, R 4 is t-butyl phenyl, D is ##STR16## where both A and B are ethyl; G is H; n=2-6; and, z=0.
Claim 16
Dependent Claim
10 words
Coumarin dye-containing polymers as defined in claim 11, where n=2.
Claim 17
Dependent Claim
10 words
Coumarin dye-containing polymers as defined in claim 11, where n=5.
Claim 18
Dependent Claim
23 words
Coumarin dye-containing polymers as defined in claim 11, where both A and B are the atoms necessary to complete a 6-membered heterocyclic ring.
Claim 19
Dependent Claim
89 words
Coumarin dye-containing polymers as defined in claim 7, where D is ##STR17## where R is selected from the group consisting of H, and alkyl of 1 to 22 carbon atoms; where G is selected from the group consisting of H, --CH 3 , and --CF 3 : where n=2 to 18; and where both A and B are selected from the group consisting of H, alkyl of 1 to 22 carbon atoms, alkenyl of 1 to 22 carbon atoms, and the atoms necessary to complete a 6-membered heterocyclic ring.
Claim 20
Dependent Claim
23 words
Coumarin dye-containing polymers as defined in claim 18 wherein both A and B are the atoms necessary to complete a 6-membered heterocyclic ring.
Claim 21
Dependent Claim
10 words
Coumarin dye-containing polymers as defined in claim 19, where n=2-6.
Claim 22
Dependent Claim
15 words
Coumarin dye-containing polymers as defined in claim 18 wherein both A and B are ethyl.
Claim 23
Dependent Claim
10 words
Coumarin dye-containing polymers as defined in claim 21, where n=2-6.
Claim 24
Dependent Claim
10 words
Coumarin dye-containing polymers as defined in claim 21, where n=2.
Claim 25
Dependent Claim
13 words
An optically nonlinear polymer film comprising the coumarin dye-containing polymer of claim 1.
Claim 26
Dependent Claim
13 words
An optically nonlinear polymer film comprising the coumarin dye-containing polymer of claim 11.
Claim 27
Dependent Claim
13 words
An optically nonlinear polymer film comprising the coumarin dye-containing polymer of claim 23.
Claim 28
Dependent Claim
10 words
A device comprising a film in accordance with claim 24.
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