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US4038456A Expired / Lapsed US ⏱️ 0.0 years remaining

Azido-silane compositions

Assignee: OSI Specialties Inc
•
Filing: 1975-10-28
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Granted: 1977-07-26
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Expires: 1995-10-28
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Abstract

Abstract Azido-containing silane compositions of matter useful as coupling agents in the production of polymer composite articles.

Inventors

  • 👤 James Glenn Marsden
  • 👤 Peter Joseph Orenski

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 10:47
CPC Classifications
B; B32; B32B; B32B7/00; B32B7/04; B32B7/12; B32B27/00; B32B27/12; B32B27/32; C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C08; C08K; C08K9/00; C08K9/04; C08K9/06; C09; C09C; C09C3/00; C09C3/12; B32B2262/00; B32B2262/10; B32B2262/101; B32B2323/00; B32B2323/10; C01; C01P; C01P2004/00; C01P2004/80; Y; Y10; Y10T; Y10T428/00; Y10T428/29; Y10T428/2904; Y10T428/2907; Y10T428/2913; Y10T428/2933; Y10T428/2962; Y10T428/31504; Y10T428/31551; Y10T428/31609; Y10T428/31612; Y10T428/31652; Y10T428/31663; Y10T428/31667

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 212 words
An article of manufacture comprising a material selected from the group consisting of siliceous materials, metals, metal oxides and organic polymers coated with a solubilized azido-containing silane composition of matter produced by a process which comprises reacting in the presence of a non-aqueous solvent a. An azido-containing carboxylic acid halide of the formula (N.sub.3 X).sub.a --Ar--(R).sub.n --COHal wherein X is a radical selected from the group consisting of sulfonyl and formyl radicals, a is an integer of from 1 to 2, Ar is an aryl radical, R is a divalent akylene radical having from 1 to 17 atoms, wherein n has a value of 0 or 1; and Hal represents a halogen radical, with (b) an amino-containing silane having the formula ##STR7## wherein R 2 is a monovalent hydrocarbon radical, b has a value of 0 to 2, Y is a hydrolyzable group selected from the class consisting of alkoxy and aryloxy radicals and wherein R' is an organic radical directly bonded to the silicon atom of said silane through a carbon to silicon bond, said organic radical further containing at least one nitrogen atom which has a hydrogen atom bonded directly to it, said solvent being present in an amount sufficient to solubilize the azido-containing silane product of (a) and (b).
Claim 2
Dependent Claim 212 words
An article of manufacture comprising a material selected from the group consisting of siliceous materials, metals, metal oxides and organic polymers coated with a solubilized azido-containing silane composition of matter produced by a process which comprises reacting in the presence of a non-aqueous solvent a. An azido-containing carboxylic acid halide of the formula (N.sub.3 X).sub.a --Ar--(R).sub.n --COHal wherein X is a radical selected from the group consisting of sulfonyl and formyl radicals, a is an integer of from 1 to 2, Ar is an aryl radical, R is a divalent akylene radical having from 1 to 17 atoms, wherein n has a value of 0 or 1; and Hal represents a halogen radical, with (b) an amino-containing silane having the formula ##STR7## wherein R 2 is a monovalent hydrocarbon radical, b has a value of 0 to 2, Y is a hydrolyzable group selected from the class consisting of alkoxy and aryloxy radicals and wherein R' is an organic radical directly bonded to the silicon atom of said silane through a carbon to silicon bond, said organic radical further containing at least one nitrogen atom which has a hydrogen atom bonded directly to it, said solvent being present in an amount sufficient to solubilize the azido-containing silane product of (a) and (b).
Claim 3
Dependent Claim 14 words
An article of manufacture as defined in claim 1, wherein the material is glass.
Claim 4
Dependent Claim 15 words
An article of manufacture as defined in claim 2, wherein the material is fiber glass.
Claim 5
Dependent Claim 67 words
An article of manufacture comprising a material selected from the group consisting of siliceous materials, metals, metal oxides and organic polymers coated with an aqueous composition comprising from about 0.1 parts by weight to about 20 parts by weight of a solubilized azido-containing silane composition of matter as defined in claim 1, and from about 99.9 parts by weight to about 80 parts by weight of water.
Claim 6
Dependent Claim 14 words
An article of manufacture as defined in claim 4, whrein the material is glass.
Claim 7
Dependent Claim 15 words
An article of manufacture as defined in claim 5, wherein the material is fiber glass.
Claim 8
Dependent Claim 175 words
An article of manufacture comprising a material selected from the group consisting of siliceous materials, metals, metal oxides and organic polymers coated with an aqueous solution comprising from about 0.1 parts by weight to about 20 parts by weight of a solubilized azido-containing silane composition as defined in claim 1, wherein the non-aqueous solvent is selected from the group consisting of alcohols, ethers, ketones and esters; wherein X is a sulfonyl radical; a is 1; Ar is phenylene; x is 0; Hal is chlorine; b is 0; Y is a lower alkoxy radical having from 1 to 4 carbon atoms and R' is an amino radical of the formula ##STR8## wherein R 3 , R 4 and R 6 individually represent a radical selected from the group consisting of hydrogen and a methyl radical; y has a value of 1 to 4; and each R 5 group individually represents a divalent alkylene radical having from 2 to 6 carbon atoms; and from about 99.9 parts by weight to about 80 parts by weight of water.
Claim 9
Dependent Claim 14 words
An article of manufacture as defined in claim 7, wherein the material is glass.
Claim 10
Dependent Claim 15 words
An article of manufacture as defined in claim 8, wherein the material is fiber glass.
Claim 11
Dependent Claim 21 words
An article of manufacture as defined in claim 7, wherein R 3 , R 4 and R 6 are hydrogen atoms.
Claim 12
Dependent Claim 24 words
An article of manufacture as defined in claim 10, wherein the azido-containing compound is 3-(azidosulfonyl) benzoyl chloride and the amino-containing silane is N-beta-(aminoethyl)-gamma-aminopropyltrimethoxy silane.
Claim 13
Dependent Claim 197 words
An article of manufacture comprising an organic polymer bonded to a substrate through a coupling agent, said coupling agent being the reaction product of an azido-containing carboxylic acid halide of the formula (N.sub.3 X).sub.a --Ar--(R).sub.n --COHal wherein X is a radical selected from the group consisting of sulfonyl and formyl radicals, a is an integer of from 1 to 2, Ar is an aryl radical, R is a divalent alkylene radical having from 1 to 17 carbon atoms, wherein n has a value of 0 or 1; and Hal represents a halogen radical, with an amino-containing silane having the formula ##STR9## wherein R 2 is a monovalent hydrocarbon radical, b has a value of 0 to 2, Y is a hydrolyzable group selected from the class consisting of alkoxy and aryloxy radicals and wherein R' is an organic radical directly bonded to the silicon atom of said silane through a carbon to silicon bond, said organic radical further containing at least one nitrogen atom which has a hydrogen atom bonded directly to it, their hydrolyzates and the condensates thereof, said substrate being selected from the group consisting of siliceous materials, metals, metal oxides, and other organic polymers.
Claim 14
Dependent Claim 197 words
An article of manufacture comprising an organic polymer bonded to a substrate through a coupling agent, said coupling agent being the reaction product of an azido-containing carboxylic acid halide of the formula (N.sub.3 X).sub.a --Ar--(R).sub.n --COHal wherein X is a radical selected from the group consisting of sulfonyl and formyl radicals, a is an integer of from 1 to 2, Ar is an aryl radical, R is a divalent alkylene radical having from 1 to 17 carbon atoms, wherein n has a value of 0 or 1; and Hal represents a halogen radical, with an amino-containing silane having the formula ##STR9## wherein R 2 is a monovalent hydrocarbon radical, b has a value of 0 to 2, Y is a hydrolyzable group selected from the class consisting of alkoxy and aryloxy radicals and wherein R' is an organic radical directly bonded to the silicon atom of said silane through a carbon to silicon bond, said organic radical further containing at least one nitrogen atom which has a hydrogen atom bonded directly to it, their hydrolyzates and the condensates thereof, said substrate being selected from the group consisting of siliceous materials, metals, metal oxides, and other organic polymers.
Claim 15
Dependent Claim 14 words
An article of manufacture as defined in claim 12, wherein the substrate is glass.
Claim 16
Dependent Claim 16 words
An article of manufacture as defined in claim 12, wherein the organic polymer is a polyolefin.
Claim 17
Dependent Claim 21 words
An article of manufacture as defined in claim 13, wherein the substrate is fiber glass and the organic polymer is polypropylene.

References Cited (Backward Citations)

US3507829A Cited
US3585103A Cited
US3697551A Cited
US3657047A Cited
US3706592A Cited
US3705911A Cited
US3900683A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-07-25 1981-01-24 1981-07-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-07-25 1985-01-24 1985-07-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-07-25 1989-01-24 1989-07-26 $7700.00 Window Closed / Lapsed

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