US4052282A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Photocurable flexible orthopedic bandage
Assignee: Mitsubishi Chemical Corp
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Filing: 1975-10-08
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Granted: 1977-10-04
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Expires: 1995-10-08
Abstract
Abstract A photocurable bandage or splint consisting of a flexible fabric, a photosensitizer and a reaction product of a hydroxyalkyl acrylate or methacrylate, a diisocyanate and a polyhydric alcohol. The photocurable bandage or splint can be produced without using a solvent and a volatile monomer by using a process which comprises impregnating the flexible fabric with a reaction mixture obtained by adding the polyhydric alcohol to a reaction product of the hydroxyalkyl acrylate or methacrylate and the diisocyanate which contains free isocyanate groups, and reacting the polyhydric alcohol with the isocyanate groups on the fabric to form a photocurable composition.
Inventors
- 👤 Kanemitsu Kubushiro
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-22 23:20
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/81; C08G18/8141; C08G18/815; C08G18/8158; C08G18/8175; A; A61; A61L; A61L15/00; A61L15/07; A61L15/12; C08L; C08L75/00; C08L75/04; C08L75/14; C08L75/16; Y; Y10; Y10T; Y10T442/00; Y10T442/20; Y10T442/2369
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
229 words
A storage-stable flexible photocurable orthopedic material such as bandage or splint for application to a body member, said orthopedic material comprising a flexible fabric, a photosensitizer and a photocurable tacky composition impregnated in the fabric, said tacky composition being a reaction product obtained by reacting a reaction product (D) of A. at least one hydroxyalkyl acrylate or hydroxyalkyl methacrylate, wherein said hydroxyalkyl portion contains 2 or 3 atoms and B. 0.55 to 3 moles, per mole of said acrylate, of at least one diisocyanate of the following formula OCN--R.sub.1 --NCO wherein R 1 represents (CH 2 ) 6 , ##STR3## C. at least one polyhydric alcohol of the following formula R.sub.2 (OOH).sub.m wherein R 2 represents a straight-chain or branched chain saturated aliphatic hydrocarbon group containing 2 to 8 carbon atoms, a cycloaliphatic hydrocarbon group, or the group ##STR4## in which n is a number of 1 to 4 and R 3 is a hydrocarbon atom or a methyl group, and m is 2, wherein the amount of the polyhydric alcohol (C) is one which affords 1.05 to 1.50 equivalents, of hydroxyl groups based on the isocyanate groups remaining in the reaction product (D), said reaction product of (D) and (C) containing at least one compound having at least two carbon-carbon double bonds capable of being polymerized and crosslinked by light and being substantially free from free isocyanate groups.
Claim 2
Dependent Claim
229 words
A storage-stable flexible photocurable orthopedic material such as bandage or splint for application to a body member, said orthopedic material comprising a flexible fabric, a photosensitizer and a photocurable tacky composition impregnated in the fabric, said tacky composition being a reaction product obtained by reacting a reaction product (D) of A. at least one hydroxyalkyl acrylate or hydroxyalkyl methacrylate, wherein said hydroxyalkyl portion contains 2 or 3 atoms and B. 0.55 to 3 moles, per mole of said acrylate, of at least one diisocyanate of the following formula OCN--R.sub.1 --NCO wherein R 1 represents (CH 2 ) 6 , ##STR3## C. at least one polyhydric alcohol of the following formula R.sub.2 (OOH).sub.m wherein R 2 represents a straight-chain or branched chain saturated aliphatic hydrocarbon group containing 2 to 8 carbon atoms, a cycloaliphatic hydrocarbon group, or the group ##STR4## in which n is a number of 1 to 4 and R 3 is a hydrocarbon atom or a methyl group, and m is 2, wherein the amount of the polyhydric alcohol (C) is one which affords 1.05 to 1.50 equivalents, of hydroxyl groups based on the isocyanate groups remaining in the reaction product (D), said reaction product of (D) and (C) containing at least one compound having at least two carbon-carbon double bonds capable of being polymerized and crosslinked by light and being substantially free from free isocyanate groups.
Claim 3
Dependent Claim
36 words
The orthopedic material of claim 1 wherein the hydroxyalkyl acrylate or hydroxyalkyl methacrylate as component (A) is at least one member selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.
Claim 4
Dependent Claim
30 words
The orthopedic material of claim 1 wherein the diisocyanate as component (B) is at least one member selected frm the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, and hexamethylene diisocyanate.
Claim 5
Dependent Claim
35 words
The orthopedic material of claim 1 wherein the polyhydric alcohol as component (C) is at least one member selected from the group consisting of diethylene glycol, dipropylene glycol, tetraethylene glycol, 1,2-propylene glycol, 1,4-butanediol and 1,6-hexanediol.
Claim 6
Independent Claim
67 words
A method for producing a storage-stable flexible photocurable orthopedic material such as a bandage or splint for application to a body member, comprising a flexible fabric, a photosensitizer and a photocurable tacky composition containing at least one compound containing at least two carbon-carbon double bonds capable of being polymerized and crosslinked by light and being substantially free from free isocyanate groups, said method comprising the steps of:
Claim 7
Independent Claim
67 words
A method for producing a storage-stable flexible photocurable orthopedic material such as a bandage or splint for application to a body member, comprising a flexible fabric, a photosensitizer and a photocurable tacky composition containing at least one compound containing at least two carbon-carbon double bonds capable of being polymerized and crosslinked by light and being substantially free from free isocyanate groups, said method comprising the steps of:
Claim 8
Dependent Claim
69 words
a first step of reacting (A) at least one hydroxyalkyl acrylate or hydroxyalkyl methacrylate wherein said hydroxyalkyl portion contains 2 or 3 carbon atoms, with (B) 0.55 to 3 moles, per mole of the hydroxyalkyl acrylate or hydroxyalkyl methacrylate, of at least one diisocyanate of the formula OCN--NCO wherein R 1 is (CH 2 ) 6 , ##STR5## to form a reaction product (D) containing remaining free isocyanate groups,
Claim 9
Dependent Claim
69 words
a first step of reacting (A) at least one hydroxyalkyl acrylate or hydroxyalkyl methacrylate wherein said hydroxyalkyl portion contains 2 or 3 carbon atoms, with (B) 0.55 to 3 moles, per mole of the hydroxyalkyl acrylate or hydroxyalkyl methacrylate, of at least one diisocyanate of the formula OCN--NCO wherein R 1 is (CH 2 ) 6 , ##STR5## to form a reaction product (D) containing remaining free isocyanate groups,
Claim 10
Dependent Claim
107 words
a second step of adding (C) at least one polyhydric alcohol of the following formula R.sub.2 (OH).sub.m wherein R 2 represents a straight-chain or branched chain aliphatic hydrocarbon group containing 2 to 8 carbon atoms, a cycloaliphatic hydrocarbon group or the group ##STR6## in which n is a number of 1 to 4, and R 3 is a hydrogen atom or a methyl group, and m is 2, wherein the amount of the polyhydric alcohol (C) is one which affords 1.05 to 1.5 equivalents, of hydroxyl groups based on the remaining isocyanate groups in the reaction product (D) of the first step, to form a reactive composition,
Claim 11
Dependent Claim
107 words
a second step of adding (C) at least one polyhydric alcohol of the following formula R.sub.2 (OH).sub.m wherein R 2 represents a straight-chain or branched chain aliphatic hydrocarbon group containing 2 to 8 carbon atoms, a cycloaliphatic hydrocarbon group or the group ##STR6## in which n is a number of 1 to 4, and R 3 is a hydrogen atom or a methyl group, and m is 2, wherein the amount of the polyhydric alcohol (C) is one which affords 1.05 to 1.5 equivalents, of hydroxyl groups based on the remaining isocyanate groups in the reaction product (D) of the first step, to form a reactive composition,
Claim 12
Dependent Claim
52 words
a third step of impregnating the flexible fabric with the reactive composition in the absence of a solvent, 4. adding photosensitizer either in the first, second or third step, and 5. a fourth step of completing the reacton of the free isocyanate groups in the impregnated composition with the polyhydric alcohol (C).
Claim 13
Dependent Claim
52 words
a third step of impregnating the flexible fabric with the reactive composition in the absence of a solvent, 4. adding photosensitizer either in the first, second or third step, and 5. a fourth step of completing the reacton of the free isocyanate groups in the impregnated composition with the polyhydric alcohol (C).
Claim 14
Dependent Claim
25 words
The method of claim 5 wherein said reactive composition is impregnated in the flexible fabric while it has a viscosity of 5 to 30 poises.
Claim 15
Dependent Claim
33 words
The method of claim 5 wherein the hydroxyalkyl acrylate or hydroxyalkyl methacrylate (A) is at least one member selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.
Claim 16
Dependent Claim
27 words
The method of claim 5 wherein the diisocyanate (B) is at least one member selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, and hexamethylene diisocyanate.
Claim 17
Dependent Claim
32 words
The method of claim 5 wherein the polyhydric alcohol (C) is at least one member selected from the group consisting of diethylene glycol, dipropylene glycol, tetraethylene glycol, 1,2-propylene glycol, 1,4-butanediol and 1,6-hexanediol.
Claim 18
Independent Claim
137 words
A method for producing a storage-stable flexible photocurable orthopedic material such as a bandage or splint for application to a body member, comprising a flexible fabric, a photosensitizer and a photocurable tacky composition containing at least one compound containing at least two carbon-carbon double bonds capable of being polymerized and crosslinked by light and being substantially free from free isocyanate groups, said method comprising the steps of: 1. a first step of reacting (A) at least one hydroxyalkyl acrylate or hydroxyalkyl methacrylate wherein said hydroxyalkyl portion contains 2 or 3 carbon atoms with (B) 0.55 to 3 moles, per mole of the hydroxyalkyl acrylate or methacrylate, of at least one diisocyanate of the formula OCN--R.sub.1 --NCO wherein R 1 represents (CH 2 ) 6 , ##STR7## to form a reaction product (D) containing remaining free isocyanate groups,
Claim 19
Independent Claim
137 words
A method for producing a storage-stable flexible photocurable orthopedic material such as a bandage or splint for application to a body member, comprising a flexible fabric, a photosensitizer and a photocurable tacky composition containing at least one compound containing at least two carbon-carbon double bonds capable of being polymerized and crosslinked by light and being substantially free from free isocyanate groups, said method comprising the steps of: 1. a first step of reacting (A) at least one hydroxyalkyl acrylate or hydroxyalkyl methacrylate wherein said hydroxyalkyl portion contains 2 or 3 carbon atoms with (B) 0.55 to 3 moles, per mole of the hydroxyalkyl acrylate or methacrylate, of at least one diisocyanate of the formula OCN--R.sub.1 --NCO wherein R 1 represents (CH 2 ) 6 , ##STR7## to form a reaction product (D) containing remaining free isocyanate groups,
Claim 20
Dependent Claim
113 words
a second step of adding (C) at least one polyhydric alcohol of the following formula R.sub.2 (OH).sub.m wherein R 2 represents a straight-chain or branched chain aliphatic hydrocarbon group containing 2 to 8 carbon atoms, a cycloaliphatic hydrocarbon group, or the group ##STR8## in which n is a number of 1 to 4 and R 3 is a hydrogen atom or a methyl group, and m is 2, wherein the amount of the polyhydric alcohol is one which affords 1.05 to 1.5 equivalents, of hydroxyl groups based on the isocyanate groups remaining in the reaction product (D) of the first step, to form a reaction product (D) containing substantially no free isocyanate groups,
Claim 21
Dependent Claim
113 words
a second step of adding (C) at least one polyhydric alcohol of the following formula R.sub.2 (OH).sub.m wherein R 2 represents a straight-chain or branched chain aliphatic hydrocarbon group containing 2 to 8 carbon atoms, a cycloaliphatic hydrocarbon group, or the group ##STR8## in which n is a number of 1 to 4 and R 3 is a hydrogen atom or a methyl group, and m is 2, wherein the amount of the polyhydric alcohol is one which affords 1.05 to 1.5 equivalents, of hydroxyl groups based on the isocyanate groups remaining in the reaction product (D) of the first step, to form a reaction product (D) containing substantially no free isocyanate groups,
Claim 22
Dependent Claim
48 words
a third step of impregnating the flexible fabric with a solution of the reaction product of the second step, 4. adding a photosensitizer and a solvent inert to the isocyanate groups either in the first, second or third step, and 5. volatilizing the solvent form the impregnated solution.
Claim 23
Dependent Claim
48 words
a third step of impregnating the flexible fabric with a solution of the reaction product of the second step, 4. adding a photosensitizer and a solvent inert to the isocyanate groups either in the first, second or third step, and 5. volatilizing the solvent form the impregnated solution.
Claim 24
Dependent Claim
24 words
The method of claim 10 wherein the reaction in the first and/or second step is carried out in the presence of a urethanization catalyst.
Claim 25
Dependent Claim
33 words
The method of claim 10 wherein the hydroxyalkyl acrylate or hydroxyalkyl methacrylate (A) is at least one member selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.
Claim 26
Dependent Claim
27 words
The method of claim 10 wherein the diisocyanate (V) is at least one member selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, and hexamethylene diisocyanate.
Claim 27
Dependent Claim
32 words
The method of claim 10 wherein the polyhydric alcohol (C) is at least one member selected from the group consisting of diethylene glycol, dipropylene glycol, tetraethylene glycol, 1,2-propylene glycol, 1,4-butanediol and 1,6-hexanediol.
Claim 28
Dependent Claim
80 words
The orthopedic material of claim 1 wherein the hydroxyalkyl acrylate or hydroxyalkyl methacrylate (A) is at least one member selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate and 2-hydroxyethyl methacrylate; said diisocyanate (B) is at least one member selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and hexamethylene diisocyanate; and the polyhydric alcohol (C) is at least one member selected from the group consisting of diethylene glycol, dipropylene glycol, tetraethylene glycol, 1,2-propylene glycol, 1,4-butanediol and 1,6-hexanediol.
Claim 29
Dependent Claim
79 words
The method of claim 5 wherein the hydroxyalkyl acrylate or hydroxyalkyl methacrylate (A) is at least one member selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate and 2-hydroxyethyl methacrylate; said diisocyanate (B) is at least one member selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and hexamethylene diisocyanate; and the polyhydric alcohol (C) is at least one member selected from the group consisting of diethylene glycol, dipropylene glycol, tetraethylene glycol, 1,2-propylene glycol, 1,4-butanediol and 1,6-hexanediol.
Claim 30
Dependent Claim
79 words
The method of claim 10 wherein the hydroxyalkyl acrylate or hydroxyalkyl methacrylate (A) is at least one member selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate and 2-hydroxyethyl methacrylate; said diisocyanate (B) is at least one member selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and hexamethylene diisocyanate; and the polyhydric alcohol (C) is at least one member selected from the group consisting of diethylene glycol, dipropylene glycol, tetraethylene glycol, 1,2-propylene glycol, 1,4-butanediol and 1,6-hexanediol.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-10-03 | 1981-04-04 | 1981-10-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-03 | 1985-04-04 | 1985-10-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-03 | 1989-04-04 | 1989-10-04 | $7700.00 | Window Closed / Lapsed |