US3876590A
Expired / Lapsed
US
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Cross-linked polymer of an epihalohydrin and a process for producing the same
Assignee: Osaka Soda Co Ltd
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Filing: 1973-09-28
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Granted: 1975-04-08
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Expires: 1993-09-28
Abstract
Abstract A cross-linked polymer of an epihalohydrin prepared by heating a polymer of an epihalohydrin in the presence of a metal salt of ethylene-bisdithiocarbamic acid having the following formula: Wherein symbol M stands for a divalent metal atom in the amount of from 0.1 to 10 parts by weight based on 100 parts by weight of the polymer of epihalohydrin, said epihalohydrin polymer being selected from the group consisting of polymers of epihalohydrin, copolymers of epihalohydrin with alkylene oxides, and mixtures containing other sulphur vulcanizable rubbers of not more than 50 percent by weight based on the weight of the mixture of the sulphur-vulcanizable rubbers with these homo- or co-polymers, and a process for preparation said polymer.
Inventors
- 👤 Sachio Shimogawa
- 👤 Nobuo Yamada
- 👤 Takashi Fujio
- 👤 Takashi Kodama
- 👤 Tetsuya Nakata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:47
CPC Classifications
C; C08; C08L; C08L21/00; C08K; C08K3/00; C08K3/18; C08K3/20; C08K3/22; C08K5/00; C08K5/16; C08K5/20; C08K5/36; C08K5/37; C08K5/372; C08K5/39; C08L7/00; C08L71/00; C08L71/02; C08L71/03; C08L9/00
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
154 words
A CROSS-LINKED POLYMER OF EPIHALOHYDRIN PREPARED BY HEATING AT 120* TO 200*C. A POLYMER OF AN EPIHALOHYDRIN IN THE PRESENCE OF A METAL SALT OF ETHYLENE-BISDITHIOCARBAMIC ACID HAVING THE FOLLOWING FORMULA: M<(-S-C(=S)-NH-CH2-CH2-NH-C(=S)-S-) WHEREIN M IS A BARIUM, ZINC, COPPER, CADMIUM, LEAD, IRON, NICKEL OR MANGANESE ION IN THE AMOUNT OF FROM 0.1 TO 10 PARTS BY WEIGHT BASED ON 100 PARTS BY WEIGHT OF THE POLYMER OF EPIHALOHYDRIN, SAID EPIHALOHYDRIN POLYMER BEING SELECTED FROM THE GROUP CONSISTING OF POLYMERS OF EPIHALOHYDRIN, COPOLYMERS OF EPIHALOHYDRIN WITH ALKYLENE OXIDES, AND MIXTURES CONTAINING THE POLYMERS OR THE COPOLYMERS AND SULPHURVULCANIZABLE RUBBERS SELECTED FROM AT LEAST ONE OF THE GROUP CONSISTING OF NATURAL RUBBER, STYRENE-BUTADIENE RUBBER, BUTADIENE RUBBER, ISOPRENE RUBBER, ISOPRENE-ISOBUTYLENE RUBBER, ACRYLONITRILE-BUTADIENE RUBBER, ETHYLENE-PROPYLENE-DIENE RUBBER AND PREPYLENE OXIDE-ALLYL GLYCIDYL ETHER COPOLYMERIZED RUBBER, AND PRESENT IN NOT MORE THAN 50% BY WEIGHT BASED ON THE WEIGHT OF THE MIXTURE OF THE SULPHUR-VULCANIZABLE RUBBERS WITH THE POLYMERS OR COPOLYMERS.
Claim 2
Dependent Claim
154 words
A CROSS-LINKED POLYMER OF EPIHALOHYDRIN PREPARED BY HEATING AT 120* TO 200*C. A POLYMER OF AN EPIHALOHYDRIN IN THE PRESENCE OF A METAL SALT OF ETHYLENE-BISDITHIOCARBAMIC ACID HAVING THE FOLLOWING FORMULA: M<(-S-C(=S)-NH-CH2-CH2-NH-C(=S)-S-) WHEREIN M IS A BARIUM, ZINC, COPPER, CADMIUM, LEAD, IRON, NICKEL OR MANGANESE ION IN THE AMOUNT OF FROM 0.1 TO 10 PARTS BY WEIGHT BASED ON 100 PARTS BY WEIGHT OF THE POLYMER OF EPIHALOHYDRIN, SAID EPIHALOHYDRIN POLYMER BEING SELECTED FROM THE GROUP CONSISTING OF POLYMERS OF EPIHALOHYDRIN, COPOLYMERS OF EPIHALOHYDRIN WITH ALKYLENE OXIDES, AND MIXTURES CONTAINING THE POLYMERS OR THE COPOLYMERS AND SULPHURVULCANIZABLE RUBBERS SELECTED FROM AT LEAST ONE OF THE GROUP CONSISTING OF NATURAL RUBBER, STYRENE-BUTADIENE RUBBER, BUTADIENE RUBBER, ISOPRENE RUBBER, ISOPRENE-ISOBUTYLENE RUBBER, ACRYLONITRILE-BUTADIENE RUBBER, ETHYLENE-PROPYLENE-DIENE RUBBER AND PREPYLENE OXIDE-ALLYL GLYCIDYL ETHER COPOLYMERIZED RUBBER, AND PRESENT IN NOT MORE THAN 50% BY WEIGHT BASED ON THE WEIGHT OF THE MIXTURE OF THE SULPHUR-VULCANIZABLE RUBBERS WITH THE POLYMERS OR COPOLYMERS.
Claim 3
Dependent Claim
29 words
The method of claim 1 in which said alkali metal bisulfide is selected from the group consisting of lithium bisulfide, sodium bisulfide, potassium bisulfide, rubidium bisulfide and cesium bisulfide.
Claim 4
Dependent Claim
138 words
A cross-linked polymer according to claim 1 in which in addition to said metal salts of ethylene-bisdithiocarbamic acid, said epihalohydrin polymer is incorporated with at least one accelerator selected from the group consisting of oxides and hydroxides of Group IIA metals of the Periodic Table, sulphur, thiuram sulfide, morpholine disulfide, secondary amines, tertiary amines, guanidines and mono- or di-carboxylates of these amines, with the proviso that: in the case of said metal oxides, said metal hydroxides and said amines or salts thereof they are contained in the amount of 0.1 - 20 parts by weight based on 100 parts by weight of the epihalohydrin polymer; and in the case of said sulphur and said sulfides, they are contained in the amount of 0.05 - 5 parts by weight based on 100 parts by weight of the epihalohydrin polymer.
Claim 5
Dependent Claim
31 words
A cross-linked polymer according to claim 1 in which said epihalohydrin is epichlorohydrin and said alkylene oxide is a member selected from the group consisting of ethylene oxides and propylene oxides.
Claim 6
Dependent Claim
32 words
The method of claim 1 in which said organic amide is selected from the group consisting of formamide, acetamide, N-methylformamide, N,N-dimethylformamide N,N-dimethylacetamide, N-ethylpropionamide, N,N-dipropylbutyramide, 2-pyrrolidone, N-methyl-2-pyrrolidone, .epsilon.-caprolactam, N-methyl-.epsilon.-caprolactam, N,N''-ethylenedi-2-pyrrolidone, hexamethylphosphoramide and teramethylurea.
Claim 7
Dependent Claim
31 words
A cross-linked polymer of an epihalohydrin prepared by heating at 120.degree. to 200.degree.C. a polymer of epihalohydrin in the presence of a metal salt of ethylene-bisdithiocarbamic acid having the following formula:
Claim 8
Dependent Claim
31 words
A cross-linked polymer of an epihalohydrin prepared by heating at 120.degree. to 200.degree.C. a polymer of epihalohydrin in the presence of a metal salt of ethylene-bisdithiocarbamic acid having the following formula:
Claim 9
Dependent Claim
22 words
The method of claim 1 in which said polyhalo-substituted aromatic compound is selected from the group consisting of 1,2-dichlorobenzene, 1,3-dichlorobenzene and 1,4-dichlorobenzene.
Claim 10
Dependent Claim
26 words
The method of claim 1 in which said alkali metal bisulfide is sodium bisulfide, said organic amide is N-methyl-2-pyrrolidone and said polyhalo-substituted aromatic compound is 1,4-dichlorobenzene.
Claim 11
Dependent Claim
37 words
A process for production of a cross-linked polymer of an epihalohydrin, characterized by heating at 120.degree. to 200.degree.C. a polymer of an epihalohydrin in the presence of a metal salt of ethylene-bisdithiocarbamic acid having the following formula:
Claim 12
Dependent Claim
37 words
A process for production of a cross-linked polymer of an epihalohydrin, characterized by heating at 120.degree. to 200.degree.C. a polymer of an epihalohydrin in the presence of a metal salt of ethylene-bisdithiocarbamic acid having the following formula:
Claim 13
Dependent Claim
21 words
The method of claim 1 in which water is removed from said composition prior to maintaining said composition at polymerization conditions.
Claim 14
Independent Claim
108 words
A method of producing a polymer which comprises: a. contacting at least one organic amide with at least one alkali metal bisulfide to form a first composition; b. contacting at least a portion of said first composition with at least one polyhalo-substituted aromatic compound wherein the halogen atoms are attached to aromatic ring carbon atoms to form a second composition, said polyhalo-substituted aromatic compound being employed in an amount to provide an alkali metal bisulfide to polyhalo-substituted aromatic compound molar ratio within the rrange of from about 0.8 to 1 to about 1.5 to 1; and, c. maintaining said second composition at polymerization conditions to form said polymer.
Claim 15
Independent Claim
108 words
A method of producing a polymer which comprises: a. contacting at least one organic amide with at least one alkali metal bisulfide to form a first composition; b. contacting at least a portion of said first composition with at least one polyhalo-substituted aromatic compound wherein the halogen atoms are attached to aromatic ring carbon atoms to form a second composition, said polyhalo-substituted aromatic compound being employed in an amount to provide an alkali metal bisulfide to polyhalo-substituted aromatic compound molar ratio within the rrange of from about 0.8 to 1 to about 1.5 to 1; and, c. maintaining said second composition at polymerization conditions to form said polymer.
Claim 16
Dependent Claim
29 words
The method of claim 7 in which said alkali metal bisulfide is selected from the group consisting of lithium bisulfide, sodium bisulfide, potassium bisulfide, rubidium bisulfide and cesium bisulfide.
Claim 17
Dependent Claim
32 words
The method of claim 7 in which said organic amide is selected from the group consisting of formamide, acetamide, N-methylformamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-ethylpropionamide, N,N-dipropylbutyramide, 2-pyrrolidone, N-methyl-2-pyrrolidone, .epsilon.-caprolactam, N-methyl-.epsilon.-caprolactam, N,N''-ethylenedi-2-pyrrolidone, hexamethylphosphoramide and tetramethylurea.
Claim 18
Dependent Claim
22 words
The method of claim 7 in which said polyhalo-substituted aromatic compound is selected from the group consisting of 1,2-dichlorobenzene, 1,3-dichlorobenzene and 1,4-dichlorobenzene.
Claim 19
Dependent Claim
26 words
The method of claim 7 in which said alkali metal bisulfide is sodium bisulfide, said organic amide is N-methyl-2-pyrrolidone and said polyhalo-substituted aromatic compound is 1,4-dichlorobenzene.
Claim 20
Dependent Claim
23 words
The method of claim 7 in which water is removed from said first composition prior to maintaining said second composition at polymerization conditions.
References Cited (Backward Citations)
US3700650A
Cited
US3708461A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-04-07 | 1978-10-07 | 1979-04-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-04-07 | 1982-10-07 | 1983-04-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-04-07 | 1986-10-07 | 1987-04-08 | $7700.00 | Window Closed / Lapsed |