US4070340A
Expired / Lapsed
US
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Amine modified polymers reacted with halogen compounds
Assignee: Polysar Ltd
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Filing: 1976-03-26
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Granted: 1978-01-24
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Expires: 1996-03-26
Abstract
Abstract Synthetic rubber compositions of improved green strength are prepared by incorporating in a synthetic rubber polymer, such as NBR or SBR, a small number of tertiary amine groups, and reacting this polymer with a halogen compound of general formula X-CH2-R-CH2-Y where X and Y represent chlorine, bromine or iodine, and R represents an aromatic group, and where X and Y are capable of forming quaternary ammonium salts with the tertiary amine groups on the polymer.
Inventors
- 👤 Evalds Lasis
- 👤 Ernest Jack Buckler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 19:27
CPC Classifications
C; C08; C08C; C08C19/00; C08C19/30
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
208 words
An improved process of preparing a synthetic rubber composition of improved green strength which comprises reacting a rubbery polymer of a C 4 -C 6 conjugated diolefin or a rubbery polymer thereof with a C 8 -C 10 vinyl or vinylidene substituted aromatic hydrocarbon or with a C 3 -C 5 vinyl compound having a nitrile group, the rubbery polymer having from about 0.5 millimoles to about 10 millimoles per 100 grams of polymer of bound tertiary amine groups therein, with a halogen compound, the improvement being that the halogen compound is of general formula X -- CH.sub.2 --R--CH.sub.2 --Y wherein X and Y each represent chlorine, bromine, or iodine, and R represents a mononuclear aromatic group containing one CH 2 --X group or a methoxy group substituted or a polynuclear aromatic group selected from diphenyl, diphenyl ether, diphenyl thioether, diphenyl alkane in which the alkane residue has from 1-4 carbon atoms, and naphthalene, the aromatic groups of the polynuclear aromatic group being unsubstituted or substituted by one or more groups selected from lower alkyl, lower alkyl halide, aryl or lower alkenyl, the groups X--CH 2 and CH 2 --Y being associated with a different nucleus of the polynuclear aromatic group, and being linked directly to said nucleus
Claim 2
Dependent Claim
208 words
An improved process of preparing a synthetic rubber composition of improved green strength which comprises reacting a rubbery polymer of a C 4 -C 6 conjugated diolefin or a rubbery polymer thereof with a C 8 -C 10 vinyl or vinylidene substituted aromatic hydrocarbon or with a C 3 -C 5 vinyl compound having a nitrile group, the rubbery polymer having from about 0.5 millimoles to about 10 millimoles per 100 grams of polymer of bound tertiary amine groups therein, with a halogen compound, the improvement being that the halogen compound is of general formula X -- CH.sub.2 --R--CH.sub.2 --Y wherein X and Y each represent chlorine, bromine, or iodine, and R represents a mononuclear aromatic group containing one CH 2 --X group or a methoxy group substituted or a polynuclear aromatic group selected from diphenyl, diphenyl ether, diphenyl thioether, diphenyl alkane in which the alkane residue has from 1-4 carbon atoms, and naphthalene, the aromatic groups of the polynuclear aromatic group being unsubstituted or substituted by one or more groups selected from lower alkyl, lower alkyl halide, aryl or lower alkenyl, the groups X--CH 2 and CH 2 --Y being associated with a different nucleus of the polynuclear aromatic group, and being linked directly to said nucleus
Claim 3
Dependent Claim
28 words
The process of claim 1 wherein the halogen compound is selected from 4,4'-bis(chloromethyl)diphenyl ether, 4,4'-bis(bromomethyl)diphenyl ether, 2,6-bis (bromomethyl)-naphthalene, 4,4'-bis(bromomethyl)diphenyl methane, 4,4'-bis(bromomethyl)diphenyl, tribromo mesitylene, 2,2',4,4'-tetrakis(bromomethyl)diphenyl ether, and di(bromomethyl) anisole.
Claim 4
Dependent Claim
36 words
The process of claim 2 wherein the rubbery polymer contains from 70-82 parts by weight of bound butadiene, from 30-18 parts by weight of bound styrene and from 0.1-1.2 parts by weight of bound dimethylaminoethyl methacrylate.
Claim 5
Dependent Claim
28 words
The process of claim 2 wherein the rubbery polymer contains from 50-80 parts by weight of bound acrylonitrile and from 0.1-1.2 parts by weight of bound dimethylaminoethyl methacrylate.
Claim 6
Dependent Claim
29 words
The process of claim 2 wherein the amount of halogen compound is such that it contains from 0.1 to 10 millimoles of halogen groups per 100 grams of polymer.
Claim 7
Dependent Claim
19 words
The process of claim 5 wherein the rubbery polymer is reacted with the halogen compound in the polymerization latex.
Claim 8
Dependent Claim
22 words
The process of claim 5 wherein the rubbery polymer is recovered from the polymerization latex and then reacted with the halogen compound.
Claim 9
Dependent Claim
203 words
An improved synthetic rubber composition of improved green strength which comprises a rubbery polymer of a C 4 -C 6 conjugated diolefin or a rubbery polymer thereof with a C 8 -C 10 vinyl or vinylidene substituted aromatic hydrocarbon or with a C 3 -C 5 vinyl compound having a nitrile group, the rubbery polymer having therein from 0.5 to 10 millimoles, per 100 grams of polymer, of bound tertiary amine groups, the rubbery polymer having been reacted with a halogen compound, the improvement being that the halogen compound is of general formula X--CH.sub.2 --CH.sub.2 --Y wherein X and Y each represent chlorine, bromine or iodine, and R represents a mononuclear aromatic group containing one CH 2 --X group or methoxy group substituent, or a polynuclear aromatic group selected from diphenyl, diphenyl ether, diphenyl thioether, diphenyl alkane in which the alkane residue has from 1-4 carbon atoms, and naphthalene, the aromatic groups of the polynuclear aromatic group being unsubstituted or substituted by one or more groups selected from lower alkyl, lower alkyl halide, aryl or lower alkenyl, the groups X-CH 2 and CH 2 -Y being associated with a different nucleus of the polynuclear aromatic group, and being linked directly to said nucleus.
Claim 10
Dependent Claim
203 words
An improved synthetic rubber composition of improved green strength which comprises a rubbery polymer of a C 4 -C 6 conjugated diolefin or a rubbery polymer thereof with a C 8 -C 10 vinyl or vinylidene substituted aromatic hydrocarbon or with a C 3 -C 5 vinyl compound having a nitrile group, the rubbery polymer having therein from 0.5 to 10 millimoles, per 100 grams of polymer, of bound tertiary amine groups, the rubbery polymer having been reacted with a halogen compound, the improvement being that the halogen compound is of general formula X--CH.sub.2 --CH.sub.2 --Y wherein X and Y each represent chlorine, bromine or iodine, and R represents a mononuclear aromatic group containing one CH 2 --X group or methoxy group substituent, or a polynuclear aromatic group selected from diphenyl, diphenyl ether, diphenyl thioether, diphenyl alkane in which the alkane residue has from 1-4 carbon atoms, and naphthalene, the aromatic groups of the polynuclear aromatic group being unsubstituted or substituted by one or more groups selected from lower alkyl, lower alkyl halide, aryl or lower alkenyl, the groups X-CH 2 and CH 2 -Y being associated with a different nucleus of the polynuclear aromatic group, and being linked directly to said nucleus.
Claim 11
Dependent Claim
26 words
The composition of claim 8 wherein the halogen compound is selected from 4,4'-bis(chloromethyl)diphenyl ether, 4,4'-bis(bromomethyl)diphenyl ether, 2,6-bis(bromomethyl)-naphthalene, 4,4'-bis(bromomethyl)diphenyl methane, 4,4'-bis(bromomethyl)diphenyl, tribromomesitylene, 2,2',4,4'-tetrakis(bromomethyl)diphenyl ether, and di(bromomethyl) anisole.
Claim 12
Dependent Claim
29 words
The composition of claim 9 wherein the amount of halogen compound is such that it contains from 0.1 to 10 millimoles of halogen groups per 100 grams of polymer.
Claim 13
Dependent Claim
36 words
The composition of claim 10 wherein the rubber polymer contains from 70-82 parts by weight of bound butadiene, from 30-18 parts by weight of bound styrene and from 0.1-1.2 parts by weight of bound dimethylaminoethyl methacrylate.
Claim 14
Dependent Claim
36 words
The composition of claim 10 wherein the rubber polymer contains from 50-80 parts by weight of bound butadiene, from 20-50 parts by weight of bound acrylonitrile and from 0.1-1.2 parts by weight of bound dimethylaminoethyl methacrylate.
References Cited (Backward Citations)
US3085074A
Cited
US3752780A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-23 | 1981-07-25 | 1982-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-23 | 1985-07-25 | 1986-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-23 | 1989-07-25 | 1990-01-24 | $7700.00 | Window Closed / Lapsed |