US4532185A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antistatic films
Assignee: 3M Co
•
Filing: 1984-05-09
•
Granted: 1985-07-30
•
Expires: 2004-05-09
Abstract
Abstract A hydroxyorganosilane composition which upon curing provides a polymer that is an electrical conductor is disclosed. The composition comprises 1 to 95 weight percent of a hydrolyzate of a hydroxyorganosilane and optionally up to 50 weight percent of a silanol-sulfonate compound. When the cured polymer, which has a siloxane backbone, is a film in a composite structure, the resultant article has antistatic properties.
Inventors
- 👤 Robert J. Balchunis
- 👤 Frank T. Sher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 18:07
CPC Classifications
C; C09; C09K; C09K3/00; C09K3/16; C09D; C09D4/00; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31652; Y10T428/31663
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
290 words
A composite structure comprising: (a) a substrate, and (b) a cured film on at least one surface of said substrate, said film comprising the cured reaction product of 1 to 95 weight percent of a hydrolyzate of a hydroxyorganosilane and 5 to 99 weight percent of an aqueous solvent, said hydroxyorganosilane having the general formula: R.sup.1 --Si(OR.sup.2).sub.3 wherein R 1 is a di-hydroxy- or polyhydroxy-substituted organic group selected from: (1) alkyl groups containing from 2 to about 8 carbon atoms and substituted by 2 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (2) alkyl groups and cyclic alkyl groups having 2 to 20 carbon atoms, which carbon chain may be interrupted by one or more oxygen atoms and containing at least two hydroxyl groups per 8 carbon atoms with any single carbon atom having at most one hydroxy group attached; (3) aralkyl or alkaryl groups containing 7 to 10 carbon atoms, said aralkyl or alkaryl group having 2 to 8 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (4) alkenyl groups containing 4 to 8 carbon atoms and 2 to 5 hydroxy groups with any single carbon atom having at most one hydroxy group attached; (5) cyclic or alkyl-substituted cyclic groups having 3 to 8 carbon atoms and substituted by 2 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; and (6) those groups selected from the group consisting of epoxy, ketal, acetal and ester which, on exhaustive hydrolysis, provide the aforementioned dihydroxy or polyhydroxyalkyl groups, and R 2 is selected from (1) hydrogen, and (2) any organic group such that the --Si(OR 2 ) 3 moiety is hydrolyzable.
Claim 2
Dependent Claim
290 words
A composite structure comprising: (a) a substrate, and (b) a cured film on at least one surface of said substrate, said film comprising the cured reaction product of 1 to 95 weight percent of a hydrolyzate of a hydroxyorganosilane and 5 to 99 weight percent of an aqueous solvent, said hydroxyorganosilane having the general formula: R.sup.1 --Si(OR.sup.2).sub.3 wherein R 1 is a di-hydroxy- or polyhydroxy-substituted organic group selected from: (1) alkyl groups containing from 2 to about 8 carbon atoms and substituted by 2 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (2) alkyl groups and cyclic alkyl groups having 2 to 20 carbon atoms, which carbon chain may be interrupted by one or more oxygen atoms and containing at least two hydroxyl groups per 8 carbon atoms with any single carbon atom having at most one hydroxy group attached; (3) aralkyl or alkaryl groups containing 7 to 10 carbon atoms, said aralkyl or alkaryl group having 2 to 8 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (4) alkenyl groups containing 4 to 8 carbon atoms and 2 to 5 hydroxy groups with any single carbon atom having at most one hydroxy group attached; (5) cyclic or alkyl-substituted cyclic groups having 3 to 8 carbon atoms and substituted by 2 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; and (6) those groups selected from the group consisting of epoxy, ketal, acetal and ester which, on exhaustive hydrolysis, provide the aforementioned dihydroxy or polyhydroxyalkyl groups, and R 2 is selected from (1) hydrogen, and (2) any organic group such that the --Si(OR 2 ) 3 moiety is hydrolyzable.
Claim 3
Dependent Claim
408 words
A process for preparing a conductive composite structure comprising the steps of: (a) providing a substrate (b) coating said substrate on at least one surface with a composition comprising the reaction product of (1) 1 to 95 weight percent of a hydrolyzate of an organosilane and 5 to 99 weight percent of an aqueous solvent, said organosilane having the general formula: R.sup.1 Si(OR.sup.2).sub.3 wherein R 1 is a hydroxy or polyhydroxy-substituted organic group selected from: (a) alkyl groups containing from 2 to about 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (b) alkyl groups and cyclic alkyl groups having up to 20 carbon atoms, which carbon chain may be interrupted by one or more oxygen atoms and containing at least one hydroxyl group per 8 carbon atoms with any single carbon atom having at most one hydroxy group attached; (c) aralkyl or alkaryl groups containing 7 to 10 carbon atoms, said aralkyl or alkaryl group having 1 to 8 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (d) alkenyl groups containing up to 8 carbon atoms and 1 to 5 hydroxy groups with any single carbon atom having at most one hydroxy group attached; (e) cyclic or alkyl-substituted cyclic groups having 3 to 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; and (f) those groups selected from the group consisting of epoxy, ketal, acetal and ester which, on exhaustive hydrolysis, provide the aforementioned hydroxy or polyhydroxyalkyl groups, and R 2 is selected from: (a) hydrogen, and (b) any organic group such that the --Si(OR 2 ) 3 moiety is hydrolyzable; and (2) 0.001 to 50 weight percent of a silanol-sulfonate compound having the general formula ##STR13## wherein Q is selected from hydroxyl, alkyl groups containing from 1 to about 4 l carbon atoms and alkoxy groups containing from 1 to 4 carbon atoms; X is an organic linking group containing up to 10 carbon atoms; Y is an organic or inorganic cation; r is equal to the valence of Y; and n is 1 or 2; with proviso that the mole ratio of silanol-sulfonate compound to organosilane is less than 5 to 1; and (c) curing said coating composition in situ with at least one curing means selected from heat and radiation.
Claim 4
Dependent Claim
408 words
A process for preparing a conductive composite structure comprising the steps of: (a) providing a substrate (b) coating said substrate on at least one surface with a composition comprising the reaction product of (1) 1 to 95 weight percent of a hydrolyzate of an organosilane and 5 to 99 weight percent of an aqueous solvent, said organosilane having the general formula: R.sup.1 Si(OR.sup.2).sub.3 wherein R 1 is a hydroxy or polyhydroxy-substituted organic group selected from: (a) alkyl groups containing from 2 to about 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (b) alkyl groups and cyclic alkyl groups having up to 20 carbon atoms, which carbon chain may be interrupted by one or more oxygen atoms and containing at least one hydroxyl group per 8 carbon atoms with any single carbon atom having at most one hydroxy group attached; (c) aralkyl or alkaryl groups containing 7 to 10 carbon atoms, said aralkyl or alkaryl group having 1 to 8 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (d) alkenyl groups containing up to 8 carbon atoms and 1 to 5 hydroxy groups with any single carbon atom having at most one hydroxy group attached; (e) cyclic or alkyl-substituted cyclic groups having 3 to 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; and (f) those groups selected from the group consisting of epoxy, ketal, acetal and ester which, on exhaustive hydrolysis, provide the aforementioned hydroxy or polyhydroxyalkyl groups, and R 2 is selected from: (a) hydrogen, and (b) any organic group such that the --Si(OR 2 ) 3 moiety is hydrolyzable; and (2) 0.001 to 50 weight percent of a silanol-sulfonate compound having the general formula ##STR13## wherein Q is selected from hydroxyl, alkyl groups containing from 1 to about 4 l carbon atoms and alkoxy groups containing from 1 to 4 carbon atoms; X is an organic linking group containing up to 10 carbon atoms; Y is an organic or inorganic cation; r is equal to the valence of Y; and n is 1 or 2; with proviso that the mole ratio of silanol-sulfonate compound to organosilane is less than 5 to 1; and (c) curing said coating composition in situ with at least one curing means selected from heat and radiation.
Claim 5
Dependent Claim
297 words
A process for preparing a conductive composite structure comprising the steps of: (a) providing a substrate; (b) coating said substrate on at least one surface with a composition comprising the reaction product of (1) 1 to 95 weight percent of a hydrolyzate of an organosilane and 5 to 99 weight percent of an aqueous solvent, said organosilane having the general formula: R.sup.1 Si(OR.sup.2).sub.3 ps wherein R 1 is a dihydroxy or polyhydroxy-substituted organic group selected from: (a) alkyl groups containing from 2 to about 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (b) alkyl groups and cyclic alkyl groups having up to 20 carbon atoms, which carbon chain may be interrupted by one or more oxygen atoms and containing at least one hydroxyl group per 8 carbon atoms with any single carbon atom having at most one hydroxy group attached; (c) aralkyl or alkaryl groups containing 7 to 10 carbon atoms, said aralkyl or alkaryl group having 1 to 8 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (d) alkenyl groups containing up to 8 carbon atoms and 1 to 5 hydroxy groups with any single carbon atom having at most one hydroxy group attached; (e) cyclic or alkyl-substituted cyclic groups having 3 to 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; and (f) those groups selected from the group consisting of epoxy, ketal, acetal and ester which, on exhaustive hydrolysis, provide the aforementioned hydroxy or polyhydroxyalkyl groups, and R 2 is selected from: (a) hydrogen, and (b) any organic group such that the --Si(OR 2 ) 3 moiety is hydrolyzable.
Claim 6
Dependent Claim
297 words
A process for preparing a conductive composite structure comprising the steps of: (a) providing a substrate; (b) coating said substrate on at least one surface with a composition comprising the reaction product of (1) 1 to 95 weight percent of a hydrolyzate of an organosilane and 5 to 99 weight percent of an aqueous solvent, said organosilane having the general formula: R.sup.1 Si(OR.sup.2).sub.3 ps wherein R 1 is a dihydroxy or polyhydroxy-substituted organic group selected from: (a) alkyl groups containing from 2 to about 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (b) alkyl groups and cyclic alkyl groups having up to 20 carbon atoms, which carbon chain may be interrupted by one or more oxygen atoms and containing at least one hydroxyl group per 8 carbon atoms with any single carbon atom having at most one hydroxy group attached; (c) aralkyl or alkaryl groups containing 7 to 10 carbon atoms, said aralkyl or alkaryl group having 1 to 8 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (d) alkenyl groups containing up to 8 carbon atoms and 1 to 5 hydroxy groups with any single carbon atom having at most one hydroxy group attached; (e) cyclic or alkyl-substituted cyclic groups having 3 to 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; and (f) those groups selected from the group consisting of epoxy, ketal, acetal and ester which, on exhaustive hydrolysis, provide the aforementioned hydroxy or polyhydroxyalkyl groups, and R 2 is selected from: (a) hydrogen, and (b) any organic group such that the --Si(OR 2 ) 3 moiety is hydrolyzable.
Claim 7
Dependent Claim
20 words
The process according to claim 3 further comprising overcoating said composite structure on any exposed surface with a compatible film.
Claim 8
Dependent Claim
45 words
The composite structure according to claim 1 wherein said substrate is selected from the group consisting of ceramic materials, metals, metal oxides, thermoplastic resins, polyesters, polycarbonates, polyamides polyolefins, acrylic resins, polyvinyl chloride, polysilanes, polysiloxanes, thermoset resins, epoxy resins, paper, wood, natural resins, textiles, and foams.
Claim 9
Dependent Claim
12 words
The composite structure according to claim 1 wherein said substrate is primed.
Claim 10
Dependent Claim
22 words
The composite structure according to claim 1 wherein said cured film has a thickness in the range of 0.1 to 25 microns.
Claim 11
Dependent Claim
22 words
The composite structure according to claim 1 wherein said cured film has a thickness in the range of 1 to 10 microns.
Claim 12
Dependent Claim
21 words
The composite structure according to claim 1 further comprising a second continuous or discontinuous film adhered on any exposed surface thereof.
Claim 13
Dependent Claim
383 words
A composite structure comprising: (a) a substrate, and (b) a cured film on at least one surface of said substrate, said film comprising the cured reaction product of (1) 1 to 95 weight percent of a hydrolyzate of an organosilane and 5 to 99 weight percent of an aqueous solvent, said organosilane having the general formula: R.sup.1 Si(OR.sup.2).sub.3 wherein R 1 is a hydroxy or polyhydroxy-substituted organic group selected from: (a) alkyl groups containing from 2 to about 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (b) alkyl groups and cyclic alkyl groups having up to 20 carbon atoms, which carbon chain may be interrupted by one or more oxygen atoms and containing at least one hydroxyl group per 8 carbon atoms with any single atom having at most one hydroxy group attached; (c) aralkyl or alkaryl groups containing 7 to 10 carbon atoms, said aralkyl or alkaryl group having 1 to 8 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (d) alkenyl groups containing up to 8 carbon atoms and 1 to 5 hydroxy groups with any single carbon atom having at most one hydroxy group attached; (e) cyclic or alkyl-substituted cyclic groups having 3 to 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; and (f) those groups selected from the group consisting of epoxy, ketal, acetal and ester which, on exhaustive hydrolysis, provide the aforementioned hydroxy or polyhydroxyalkyl groups, and R 2 is selected from: (a) hydrogen, and (b) any organic group such that the --Si(OR 2 ) 3 moiety is hydrolyzable, and; (2) 0.001 to 50 weight percent of a silanol-sulfonate compound having the general formula ##STR14## wherein Q is selected from hydroxyl, alkyl groups containing from 1 to about 4 carbon atoms and alkoxy groups containing from 1 to 4 carbon atoms; X is an organic linking group containing up to 10 carbon atoms; Y is an organic or inorganic cation; r is equal to the valence of Y; and n is 1 or 2; with the proviso that the mole ratio of silanol-sulfonate compound to organosilane is less than 5 to 1.
Claim 14
Dependent Claim
383 words
A composite structure comprising: (a) a substrate, and (b) a cured film on at least one surface of said substrate, said film comprising the cured reaction product of (1) 1 to 95 weight percent of a hydrolyzate of an organosilane and 5 to 99 weight percent of an aqueous solvent, said organosilane having the general formula: R.sup.1 Si(OR.sup.2).sub.3 wherein R 1 is a hydroxy or polyhydroxy-substituted organic group selected from: (a) alkyl groups containing from 2 to about 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (b) alkyl groups and cyclic alkyl groups having up to 20 carbon atoms, which carbon chain may be interrupted by one or more oxygen atoms and containing at least one hydroxyl group per 8 carbon atoms with any single atom having at most one hydroxy group attached; (c) aralkyl or alkaryl groups containing 7 to 10 carbon atoms, said aralkyl or alkaryl group having 1 to 8 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; (d) alkenyl groups containing up to 8 carbon atoms and 1 to 5 hydroxy groups with any single carbon atom having at most one hydroxy group attached; (e) cyclic or alkyl-substituted cyclic groups having 3 to 8 carbon atoms and substituted by 1 to 7 hydroxy groups, with any single carbon atom having at most one hydroxy group attached; and (f) those groups selected from the group consisting of epoxy, ketal, acetal and ester which, on exhaustive hydrolysis, provide the aforementioned hydroxy or polyhydroxyalkyl groups, and R 2 is selected from: (a) hydrogen, and (b) any organic group such that the --Si(OR 2 ) 3 moiety is hydrolyzable, and; (2) 0.001 to 50 weight percent of a silanol-sulfonate compound having the general formula ##STR14## wherein Q is selected from hydroxyl, alkyl groups containing from 1 to about 4 carbon atoms and alkoxy groups containing from 1 to 4 carbon atoms; X is an organic linking group containing up to 10 carbon atoms; Y is an organic or inorganic cation; r is equal to the valence of Y; and n is 1 or 2; with the proviso that the mole ratio of silanol-sulfonate compound to organosilane is less than 5 to 1.
Claim 15
Dependent Claim
21 words
The composite structure according to claim 10 wherein said film further comprises 1 to 5 weight percent of an acid catalyst.
Claim 16
Dependent Claim
21 words
The composite structure according to claim 10 further comprising a second continuous or discontinuous film adhered to any exposed surface thereof.
Claim 17
Dependent Claim
24 words
The composite structure according to claim 12 wherein said overcoating film is derived from at least one silane monomer, oligomer, polymer, or its hydrolyzate.
Claim 18
Dependent Claim
28 words
The composite structure according to claim 12 wherein said overcoating film is derived from heat or radiation curable silane monomers, or oligomers or hydrolyzates thereof selected from: ##STR15##
Claim 19
Dependent Claim
31 words
The composite structure according to claim 12 wherein said overcoating film is selected from the group consisting of adhesives, gelatin containing layers, photoemulsions, photoconductive coatings, abrasion resistant coatings, and dielectric materials.
Claim 20
Dependent Claim
69 words
The composite structure according to claim 10 wherein Y is selected from hydrogen, alkali metals, alkaline earth metals, transition metals, heavy metals, organic cations of protonated weak bases having an average molecular weight of less than 400 and a pK a of less than 11, and organic cations of strong organic bases having an average molecular weight of less than 400 and a pK a of greater than 11.
Claim 21
Dependent Claim
11 words
The composite structure according to claim 16 wherein Y is hydrogen.
Claim 22
Dependent Claim
37 words
The composite structure according to claim 10 wherein said silanol-sulfonate compound is replaced by a monomeric or polymeric alkyl-, aryl-, alkaryl-, and aralkyl-sulfonic acid, or salt thereof, having up to 20 carbon atoms per sulfonic acid group.
Claim 23
Dependent Claim
20 words
The process according to claim 2 further comprising overcoating said composite structure on any exposed surface with a compatible film.
Claim 24
Dependent Claim
17 words
The process according to claim 2 wherein said cured coating composition is subjected to a cation-exchange procedure.
Claim 25
Dependent Claim
13 words
The process according to claim 20 wherein said cation-exchange procedure employs cationic dyes.
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