Patent US1817381A successfully refreshed from Google Patents.
Patent US4525541A successfully refreshed from Google Patents.
US4525541A
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Method for modifying rubbers
Assignee: Zeon Corp
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Filing: 1983-06-22
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Granted: 1985-06-25
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Expires: 2003-06-22
Abstract
Abstract A method for modifying a rubber having an unsaturated carbon bond which comprises reacting the rubber with an organic compound represented by the general formula ##STR1## wherein --R represents a hydrocarbon group, and --X is --H, --CN or ##STR2## in which --Y represents an organic atomic grouping, in the presence of a Lewis acid to introduce an ester group. Optionally, the ester group introduced is converted into a carboxyl group by chemically treating the reaction product.
Inventors
- 👤 Shizuo Kitahara
- 👤 Nagatoshi Sugi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 21:38
CPC Classifications
C; C08; C08C; C08C19/00
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
93 words
A method for modifying a rubber, which comprises reacting a rubber having an unsaturated carbon bond with an organic compound represented by the general formula ##STR11## wherein --R represents a hydrocarbon group and --X represents --H, --CN or ##STR12## in which Y represents --R 1 , --OR 2 or --NR 3 R 4 , in which R 1 , R 2 , R 3 and R 4 are hydrocarbon groups, in the presence of a Lewis acid to introduce an ester group of the organic compound into the rubber by an addition reaction.
Claim 2
Independent Claim
93 words
A method for modifying a rubber, which comprises reacting a rubber having an unsaturated carbon bond with an organic compound represented by the general formula ##STR11## wherein --R represents a hydrocarbon group and --X represents --H, --CN or ##STR12## in which Y represents --R 1 , --OR 2 or --NR 3 R 4 , in which R 1 , R 2 , R 3 and R 4 are hydrocarbon groups, in the presence of a Lewis acid to introduce an ester group of the organic compound into the rubber by an addition reaction.
Claim 3
Dependent Claim
16 words
The method of claim 1 wherein the rubber having an unsaturated carbon bond is polyisoprene rubber.
Claim 4
Dependent Claim
25 words
The method of claim 1 wherein the Lewis acid is SnCl 4 , BF 3 O(C 2 H 5 ) 2 or TiCl 4 .
Claim 5
Dependent Claim
19 words
The method of claim 1 wherein --R in the general formula represents an aliphatic, alicyclic or aromatic hydrocarbon group.
Claim 6
Dependent Claim
13 words
The method of claim 1 wherein --X in the general formula is ##STR13##
Claim 7
Independent Claim
110 words
A method for modifying a rubber, which comprises reacting a rubber having an unsaturated carbon bond with an organic compound represented by the general formula ##STR14## wherein --R represents a hydrocarbon group, and --X is --H, --CN or ##STR15## in which --Y represents --R 1 , --OR 2 or --NR 3 R 4 , in which R 1 , R 2 , R 3 and R 4 are hydrocarbon groups, in the presence of a Lewis acid to introduce an ester group of the organic compound into the rubber by an addition reaction, and thereafter converting the ester group either partly or wholly into a carboxyl group by chemical treatment.
Claim 8
Independent Claim
110 words
A method for modifying a rubber, which comprises reacting a rubber having an unsaturated carbon bond with an organic compound represented by the general formula ##STR14## wherein --R represents a hydrocarbon group, and --X is --H, --CN or ##STR15## in which --Y represents --R 1 , --OR 2 or --NR 3 R 4 , in which R 1 , R 2 , R 3 and R 4 are hydrocarbon groups, in the presence of a Lewis acid to introduce an ester group of the organic compound into the rubber by an addition reaction, and thereafter converting the ester group either partly or wholly into a carboxyl group by chemical treatment.
Claim 9
Dependent Claim
16 words
The method of claim 6 wherein the rubber having an unsaturated carbon bond is polyisoprene rubber.
Claim 10
Dependent Claim
26 words
The method of claim 6 wherein the Lewis acid is SnCl 4 , BF 3 O(C 2 H 5 ) 2 , or TiCl 4 .
Claim 11
Dependent Claim
19 words
The method of claim 6 wherein --R in the general formula is an aliphatic, alicyclic or aromatic hydrocarbon group.
Claim 12
Dependent Claim
13 words
The method of claim 6 wherein --X in the general formula is ##STR16##
Claim 13
Dependent Claim
24 words
The method of claim 6 wherein the chemical treatment is carried out in the presence of an acid, an alkali, or a radical generator.
Claim 14
Dependent Claim
30 words
The method of claim 1 wherein the rubber is reacted with 0.0001 to 20 parts by weight per 100 parts by weight of the unsaturated rubber of the organic compound.
Claim 15
Dependent Claim
37 words
The method of claim 1 wherein the addition reaction between the rubber and the organic compound is carried out in the presence of 0.01 to 5 moles, per mole of the organic compound, of the Lewis acid.
Claim 16
Dependent Claim
25 words
The method of claim 1 wherein the addition reaction is carried out in a solvent, or in the absence of a solvent in a kneader.
Claim 17
Dependent Claim
22 words
The method of claim 1 wherein the addition reaction is carried out at a temperature of from -20° C. to 100° C.
Claim 18
Dependent Claim
19 words
The method of claim 1 wherein the addition reaction is carried out for from 10 seconds to 10 hours.
Claim 19
Dependent Claim
71 words
The method of claim 1 wherein the rubber having an unsaturated carbon bond is selected from the group consisting of natural rubber, quayule gum, polyisoprene rubber, polybutadiene rubber, styrene-butadiene copolymer rubber, butadiene-isoprene copolymer rubber, isoprene-styrene copolymer rubber, butadiene-isoprene-styrene copolymer rubber, butadiene-piperylene copolymer rubber, butadiene-propylene alternate copolymer rubber, polypentenamer, ethylene propylene-diene copolymer rubber, butyl rubber, butadiene-acrylonitrile copolymer rubber, butadiene-isoprene-acrylonitrile copolymer rubber, polychloroprene rubber, styrene-butadiene-styrene block copolymer rubber and styrene-isoprene-styrene block copolymer rubber.
Claim 20
Dependent Claim
10 words
The method of claim 1 in which --X is --H--.
Claim 21
Dependent Claim
34 words
The method of claim 18 wherein the organic compound is selected from the group consisting of methyl glyoxylate, ethyl glyoxylate, isopropyl glyoxylate, tertiary butyl glyoxylate, benzyl glyoxylate, phenyl glyoxylate, octyl glyoxylate and stearyl glyoxylate.
Claim 22
Independent Claim
209 words
A method for introducing an ester group by an addition reaction into a rubber having an unsaturated carbon bond which comprises reacting 100 parts by weight of the unsaturated rubber with 0.0001 to 20 parts by weight of an organic compound represented by the general formula ##STR17## wherein --R represents an aliphatic, alicyclic or aromatic hydrocarbon group, and --X represents --H, --CN or ##STR18## in which Y represents --R 1 , --OR 2 or --NR 3 R 4 , in which R 1 , R 2 , R 3 and R 4 are hydrocarbon groups in the presence of 0.01 to 5 moles, per mole of the organic compound, of a Lewis acid selected from the group consisting of BF 3 , BF 3 O(C 2 H 5 ) 2 , (CH 2 ) 2 BF, BCl 3 , AlCl 3 , AlBr 3 , (C 2 H 5 )AlCl 2 , POCl 3 , TiCl 4 , VCl 4 , MoCl 6 , SnCl 4 , (CH 3 )SnCl 3 , SbCl 5 , TeCl 4 , TeBr 4 , FeCl 3 , WCl 6 and (CF 3 COO) 2 Hg at a temperature of from -20° C. to 100° C. for from 10 seconds to 10 hours.
Claim 23
Independent Claim
209 words
A method for introducing an ester group by an addition reaction into a rubber having an unsaturated carbon bond which comprises reacting 100 parts by weight of the unsaturated rubber with 0.0001 to 20 parts by weight of an organic compound represented by the general formula ##STR17## wherein --R represents an aliphatic, alicyclic or aromatic hydrocarbon group, and --X represents --H, --CN or ##STR18## in which Y represents --R 1 , --OR 2 or --NR 3 R 4 , in which R 1 , R 2 , R 3 and R 4 are hydrocarbon groups in the presence of 0.01 to 5 moles, per mole of the organic compound, of a Lewis acid selected from the group consisting of BF 3 , BF 3 O(C 2 H 5 ) 2 , (CH 2 ) 2 BF, BCl 3 , AlCl 3 , AlBr 3 , (C 2 H 5 )AlCl 2 , POCl 3 , TiCl 4 , VCl 4 , MoCl 6 , SnCl 4 , (CH 3 )SnCl 3 , SbCl 5 , TeCl 4 , TeBr 4 , FeCl 3 , WCl 6 and (CF 3 COO) 2 Hg at a temperature of from -20° C. to 100° C. for from 10 seconds to 10 hours.
Claim 24
Dependent Claim
16 words
The method of claim 20 wherein in the formula of the organic compound --X represents --H.
Claim 25
Dependent Claim
25 words
The method of claim 20 wherein the Lewis acid is SnCl 4 , BF 3 O(C 2 H 5 ) 2 or TiCl 4 .
Claim 26
Dependent Claim
38 words
The method of claim 20 which further comprises converting the ester group introduced into the rubber either partly or wholly into a carboxyl group by contacting the modified rubber with an acid, an alkali or a radical generator.
Claim 27
Dependent Claim
30 words
The method of claim 1 wherein the rubber is reacted with 0.01 to 5 parts by weight, per 100 parts by weight of the unsaturated rubber, of the organic compound.
Claim 28
Dependent Claim
30 words
The method of claim 6 wherein the rubber is reacted with 0.01 to 5 parts by weight, per 100 parts by weight of the unsaturated rubber, of the organic compound.
Claim 29
Dependent Claim
30 words
The method of claim 20 wherein the rubber is reacted with 0.01 to 5 parts by weight, per 100 parts by weight of the unsaturated rubber, of the organic compound.
Claim 30
Dependent Claim
24 words
The method of claim 1 wherein the organic compound is selected from the group consisting of methyl oxocyanoacetate, ethyl oxocyanoacetate and tertiary butyl oxocyanoacetate.
Claim 31
Dependent Claim
40 words
The method of claim 1 wherein the organic compound is selected from the group consisting of methyl oxoacetoacetate, butyl oxoacetoacetate, methyl oxobenzoylacetate, butyl oxobenzoylacetate, dimethyl oxomalonate, diethyl oxomalonate, diisopropyl oxomalonate, di-tertiary butyl oxomalonate, dibenzyl oxomalonate, ethyl 2,3-dioxo-3-(dimethylamino)propionate and methyl 2,3-dioxo-3-(diethylamino)propionate.
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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) | 1988-06-24 | 1988-12-24 | 1989-06-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-06-24 | 1992-12-24 | 1993-06-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-06-24 | 1996-12-24 | 1997-06-25 | $7700.00 | Window Closed / Lapsed |