US4287322A
Expired / Lapsed
US
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Epichlorohydrin elastomer compositions
Assignee: Dyneon LLC
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Filing: 1979-10-23
•
Granted: 1981-09-01
•
Expires: 1999-10-23
Abstract
Abstract A gum stock composition comprising polyepichlorohydrin gum, polyphenol, organo-onium compound, and acid acceptor is shaped and cured to form shaped elastomeric articles.
Inventors
- 👤 Allan T. Worm
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 10:07
CPC Classifications
C; C08; C08L; C08L71/00; C08L71/02; C08L71/03; C08K; C08K5/00; C08K5/0008; C08K5/0025
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
206 words
A polyepichlorohydrin gum stock composition, comprising: (a) polyepichlorohydrin gum; (b) polyphenol curing agent; (c) organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (X.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m or (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; which composition in reactive association with an acid acceptor will, upon exposure to heat, cure into an elastomer.
Claim 2
Dependent Claim
206 words
A polyepichlorohydrin gum stock composition, comprising: (a) polyepichlorohydrin gum; (b) polyphenol curing agent; (c) organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (X.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m or (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; which composition in reactive association with an acid acceptor will, upon exposure to heat, cure into an elastomer.
Claim 3
Dependent Claim
68 words
A composition according to claim 1, wherein said curing agent is selected from the class consisting of: (i) polyhydroxy benzenes, naphthalenes, anthracenes, chromones, xanthones, and anthraquinones; and (ii) polyphenols of the formula ##STR3## wherein p is 0 or 1; the sum (q+r) is 2 or more; and A is a thio, oxy, sulfinyl, sulfonyl or carbonyl radical or a divalent organic radical containing 1 to 13 carbon atoms.
Claim 4
Dependent Claim
11 words
A composition according to claim 1, further comprising a heat stabilizer.
Claim 5
Dependent Claim
13 words
A composition according to claim 1, wherein said curing agent is Bisphenol S.
Claim 6
Dependent Claim
14 words
A composition according to claim 1, wherein said cocuring agent is a tetraorganophosphonium salt.
Claim 7
Dependent Claim
38 words
A composition according to claim 1, wherein said composition contains, per 100 grams of said polyepichlorohydrin gum, from about 0.3 to 15 millimoles of said curing agent, and from about 0.2 to 7.5 millimoles of said cocuring agent.
Claim 8
Dependent Claim
31 words
A composition according to claim 6, wherein said composition contains, per 100 parts by weight of said polyepichlorohydrin gum, from about 0.1 to 20 parts by weight of a heat stabilizer.
Claim 9
Dependent Claim
21 words
A composition according to claim 6, wherein said curing agent is Bisphenol S, and said cocuring agent is a tetraorganophosphonium salt.
Claim 10
Dependent Claim
193 words
A curable polyepichlorohydrin gum stock composition comprising: (a) polyepichlorohydrin gum; (b) polyphenol curing agent; (c) organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (X.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; and (d) an acid acceptor.
Claim 11
Dependent Claim
193 words
A curable polyepichlorohydrin gum stock composition comprising: (a) polyepichlorohydrin gum; (b) polyphenol curing agent; (c) organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (X.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; and (d) an acid acceptor.
Claim 12
Dependent Claim
68 words
A composition according to claim 9, wherein said curing agent is selected from the class consisting of (a) polyhydroxy benzenes, naphthalenes, anthracenes, chromones, xanthones, and anthraquinones; and (b) polyphenols of the formula ##STR4## wherein p is 0 or 1; the sum (q+r) is 2 or more; and A is a thio, oxy, sulfinyl, sulfonyl, or carbonyl radical or a divalent organic radical containing 1 to 13 carbon atoms.
Claim 13
Dependent Claim
11 words
A composition according to claim 9, further comprising a heat stabilizer.
Claim 14
Dependent Claim
13 words
A composition according to claim 9, wherein said curing agent is Bisphenol S.
Claim 15
Dependent Claim
14 words
A composition according to claim 9, wherein said cocuring agent is a tetraorganophosphonium salt.
Claim 16
Dependent Claim
14 words
A composition according to claim 9, wherein said acid acceptor is an inorganic base.
Claim 17
Dependent Claim
17 words
A composition according to claim 9, wherein said acid acceptor is dibasic lead phosphite or white lead.
Claim 18
Dependent Claim
48 words
A composition according to claim 9, wherein said composition contains, per 100 grams of said polyepichlorohydrin gum, from about 0.3 to 15 millimoles of said curing agent, from about 0.2 to 7.5 millimoles of said cocuring agent, and from about 0.5 to 40 grams of said acid acceptor.
Claim 19
Dependent Claim
28 words
A composition according to claim 16, wherein said curing agent is Bisphenol S, said cocuring agent is a tetraorganophoshonium salt, and said acid acceptor is an inorganic base.
Claim 20
Dependent Claim
217 words
A composition comprising: (a) polyepichlorohydrin gum; (b) polyphenol curing agent; and (c) organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (X.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m or (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; said composition containing, per 100 parts of said polyepichlorohydrin gum, from about 100 to 900 parts of said curing agent, and from about 100 to 900 parts of said cocuring agent.
Claim 21
Dependent Claim
217 words
A composition comprising: (a) polyepichlorohydrin gum; (b) polyphenol curing agent; and (c) organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (X.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m or (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; said composition containing, per 100 parts of said polyepichlorohydrin gum, from about 100 to 900 parts of said curing agent, and from about 100 to 900 parts of said cocuring agent.
Claim 22
Dependent Claim
44 words
A masterbatch useful in making curable polyepichlorohydrin gumstock, said masterbatch comprising a combination of 100 parts by weight of a polyepichlorohydrin gum as the carrier of said masterbatch and 100-900 parts by weight of a polyphenol as a curing agent for said polyepichlorohydrin gumstock.
Claim 23
Dependent Claim
44 words
A masterbatch useful in making curable polyepichlorohydrin gumstock, said masterbatch comprising a combination of 100 parts by weight of a polyepichlorohydrin gum as the carrier of said masterbatch and 100-900 parts by weight of a polyphenol as a curing agent for said polyepichlorohydrin gumstock.
Claim 24
Dependent Claim
199 words
A composition comprising: (a) polyepichlorohydrin gum; and (b) organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (S.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m or (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; said composition containing 100 to 900 parts of said cocuring agent per 100 parts of said gum.
Claim 25
Dependent Claim
199 words
A composition comprising: (a) polyepichlorohydrin gum; and (b) organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (S.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m or (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; said composition containing 100 to 900 parts of said cocuring agent per 100 parts of said gum.
Claim 26
Independent Claim
249 words
A method for curing a polyepichlorohydrin gum, comprising the steps of: (a) admixing therewith, per one hundred grams of said polyepichlorohydrin gum, from about 0.3 to 15 millimoles of polyphenol curing agent; from about 0.2 to 7.5 millimoles of organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (X.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m or (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; and from about 0.5 to 40 grams of an acid acceptor; (b) shaping said admixture by molding or extruding; and (c) subjecting said shaped admixture to sufficient heat and pressure to form a vulcanized shaped article.
Claim 27
Independent Claim
249 words
A method for curing a polyepichlorohydrin gum, comprising the steps of: (a) admixing therewith, per one hundred grams of said polyepichlorohydrin gum, from about 0.3 to 15 millimoles of polyphenol curing agent; from about 0.2 to 7.5 millimoles of organo-onium cocuring agent selected from compounds of the formulas (R.sup.1).sub.4 Q.sup.+1 (X.sup.-m).sub.1/m (R.sup.1).sub.3 QR.sup.2 Q(R.sup.1).sub.3.sup.+2 (X.sup.-m).sub.2/m wherein Q is a nitrogen, arsenic or phosphorus atom; X is an anion of valence m; each R 1 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 1 , and can combine with another R 1 to form a cyclic structure containing a Q atom; and R 2 is a divalent organic radical containing 2 to 12 carbon atoms; (R.sup.3).sub.3 S.sup.+1 (X.sup.-m).sub.1/m or (R.sup.3).sub.2 SR.sup.4 S(R.sup.3).sub.2.sup.+2 (X.sup.-m).sub.2/m wherein S is sulfur; X is an anion of valence m; each R 3 is a monovalent organic radical containing 1 to 20 carbon atoms, is the same as or different from any other R 3 , and can combine with another R 3 to form a cyclic structure containing an S atom; R 4 is a divalent organic radical containing 2 to 12 carbon atoms; and at least one R 3 or R 4 group is aromatic; and from about 0.5 to 40 grams of an acid acceptor; (b) shaping said admixture by molding or extruding; and (c) subjecting said shaped admixture to sufficient heat and pressure to form a vulcanized shaped article.
Claim 28
Dependent Claim
37 words
A method according to claim 21, wherein said admixing step further comprises the addition of from about 0.1 to 20 parts by weight of a heat stabilizer per one hundred parts by weight of said polyepichlorohydrin gum.
Claim 29
Dependent Claim
28 words
A method according to claim 21, wherein said curing agent is Bisphenol S, said cocuring agent is a tetraorganophosphonium salt, and said acid acceptor is an inorganic base.
Claim 30
Dependent Claim
8 words
A shaped article made according to claim 21.
Claim 31
Dependent Claim
8 words
A shaped article made according to claim 22.
Claim 32
Dependent Claim
8 words
A shaped article made according to claim 23.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1984-08-31 | 1985-03-02 | 1985-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-31 | 1989-03-02 | 1989-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-31 | 1993-03-02 | 1993-09-01 | $7700.00 | Window Closed / Lapsed |