US4439600A
Expired / Lapsed
US
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Cure to elastomers compositions
Assignee: Henkel Loctite Corp
•
Filing: 1983-06-03
•
Granted: 1984-03-27
•
Expires: 2003-06-03
Abstract
Abstract Disclosed are cure-to-elastomer compositions comprising: (A) a moderate-to-long chain di or polyfunctional prepolymer having vinyl reactive ends, (B) a cross-link controlling material which is (i) reactive with said moderate-to-long chain di or polyfunctional prepolymer, and (ii) soluble in or miscible with the moderate-to-long chain prepolymer; and (C) a free radical polymerization initiator. The polymerizable compositions of the present invention can be rapidly cured at room or moderate temperature to produce elastomeric materials of high flexibility and appropriate tensile strength.
Inventors
- 👤 James P. Moran, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 20:53
CPC Classifications
C; C08; C08L; C08L75/00; C08L75/04; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/81; C08G18/8141; C08G18/815; C08G18/8158; C08G18/8175; C08F; C08F290/00; C08F290/02; C08F290/06; C08F290/067; C08F290/08; C08F290/14; C08G18/28; C08G18/67; C08G18/671; C08G18/672; Y; Y10; Y10S; Y10S525/00; Y10S525/92
Claims Analysis
Total Claims: 76
Claim 1
Independent Claim
53 words
A cure-to-elastomer composition comprising, in combination: (a) a moderate-to-long chain di or polyfunctional prepolymer having vinyl reactive ends; (b) a cross-link controlling material which is (i) reactive with said moderate-to-long chain di or polyfunctional prepolymer, and (ii) soluble in or miscible with said moderate-to-long chain prepolymer; and (c) a free radical polymerization initiator.
Claim 2
Dependent Claim
53 words
A cure-to-elastomer composition comprising, in combination: (a) a moderate-to-long chain di or polyfunctional prepolymer having vinyl reactive ends; (b) a cross-link controlling material which is (i) reactive with said moderate-to-long chain di or polyfunctional prepolymer, and (ii) soluble in or miscible with said moderate-to-long chain prepolymer; and (c) a free radical polymerization initiator.
Claim 3
Dependent Claim
26 words
The composition of claim 1, wherein said cross-link controlling material comprises a monofunctional short chain monomer, a polymerization chain transfer coupling agent, or a mixture thereof.
Claim 4
Dependent Claim
27 words
The composition of claim 1, wherein said moderate-to-long chain polyfunctional prepolymer comprises a polyether-urethane-acrylate, a polyether-urethane-methacrylate, a polyester-urethane-acrylate, a polyester-urethane methacrylate, or an allyl alcohol derivative thereof.
Claim 5
Dependent Claim
18 words
The composition of claim 3, wherein the polyester portion of said polyester-urethane-acrylate or -methacrylate comprises a polyester diol.
Claim 6
Dependent Claim
19 words
The composition of claim 4, wherein said polyester diol comprises the reaction product of diethylene glycol and adipic acid.
Claim 7
Dependent Claim
22 words
The composition of claim 4, wherein said polyester diol comprises the reaction product of neopentyl glycol and 1,6-hexane diol with adipic acid.
Claim 8
Dependent Claim
18 words
The composition of claim 3, wherein the polyether portion of said polyether-urethane-acrylate or -methacrylate comprises a polyether diol.
Claim 9
Dependent Claim
19 words
The composition of claim 7, wherein said polyether diol comprises a polyether with a 1,4 butylene oxide repeat unit.
Claim 10
Dependent Claim
36 words
The composition of claim 1, wherein said moderate-to-long chain polyfunctional prepolymer comprises a difunctional monomer selected from the group consisting of a dimaleate half ester of polydiethylene glycol adipate and a dimethacrylate of polydiethylene glycol adipate.
Claim 11
Dependent Claim
21 words
The composition according to claim 1, wherein said moderate-to-long chain polyfunctional prepolymer comprises a diallyl urethane of polydiethylene glycol adipate polyester.
Claim 12
Dependent Claim
22 words
A composition according to claim 1, wherein said free radical catalyst system comprises a free-radical initiator and an accelerator of free-radical polymerization.
Claim 13
Dependent Claim
22 words
A composition of claim 11, wherein said free-radical initiator is selected from the group consisting of organic peroxides, hydroperoxides, peresters and peracids.
Claim 14
Dependent Claim
14 words
The composition of claim 12, wherein said perester free radical initiator comprises t-butyl perbenzoate.
Claim 15
Dependent Claim
13 words
The composition of claim 12, wherein said free radical initiator comprises cumene hydroperoxide.
Claim 16
Dependent Claim
13 words
The composition of claim 1, wherein said free-radical initiator is of the photoinitiator-type.
Claim 17
Dependent Claim
26 words
The composition of claim 1, wherein said polymerization initiator comprises 0.1 to 10 percent by weight of the combination of said polymerizable monomers and said initiator.
Claim 18
Dependent Claim
30 words
A composition of claim 1, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of monomethacrylate and monoacrylate esters of aryl, alkyl and arylalkyl alcohols.
Claim 19
Dependent Claim
29 words
The composition of claim 1, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of arylamino, alkylamino and arylalkyl amino methacrylate and acrylate esters.
Claim 20
Dependent Claim
38 words
The composition of claim 1, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of the reaction products of phenyl glycidyl ether and methacrylic acid or acrylic acid, 3-phenoxy-2-hydroxypropyl methacrylate and 3-phenoxy-2-hydroxypropyl acrylate.
Claim 21
Dependent Claim
49 words
The composition of claim 1, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of the reaction products of methacrylic acid or acrylic acid with para-tertiary butyl phenyl glycidyl ether, ortho-cresyl glycidyl ether, butyl glycidyl ether and the glycidyl ethers of decane to octadecane.
Claim 22
Dependent Claim
47 words
The composition of claim 1, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of glycidyl acrylate and methacrylate esters, mixed esters of glycerol 1-(2-ethyl) hexanoate-3-methacrylate and glycerol 1-(2-ethyl) hexanoate-3-acrylate prepared by reacting glycidyl methacrylate or glycidyl acrylate and 2-ethyl hexanoic acid.
Claim 23
Dependent Claim
32 words
The composition of claim 1, wherein said cross-link controlling material comprises a co-reactive monomer selected from a group consisting of the reaction products of 1-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, 2-hydroxypropylmethacrylate and 2-hydroxypropylacrylate and an isocyanate.
Claim 24
Dependent Claim
49 words
The composition of claim 1, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of the reaction products of 2-hydroxyethylmethacrylate and methanol with toluene diisocyanate, 2-hydroxypropyl methacrylate and methanol with toluene diisocyanate; 2-hdyroxyethylmethacrylate and isopentyl alcohol with 2,4 toluenediisocyanate; and 2-hydroxyethyl methacrylate with phenylisocyanate.
Claim 25
Dependent Claim
36 words
The composition of claim 2, wherein said cross-link controlling material comprises a polymerization chain transfer and coupling agent selected from the group consisting of the dimercaptoacetates and substituted dimercaptocarboxycylic acid esters of glycol polyethers and polyesters.
Claim 26
Dependent Claim
17 words
The composition of claim 24, wherein said polymerization chain transfer and coupling agent comprises triethylene glycol dimercaptoacetate.
Claim 27
Dependent Claim
17 words
The composition of claim 22, wherein said polymerization chain transfer and coupling agent comprises triethylene glycol dimercaptopropionate.
Claim 28
Dependent Claim
20 words
The composition of claim 24, wherein said polymerization chain transfer and coupling agent comprises the dimercaptoproprionate of polydiethylene glycol adipate.
Claim 29
Dependent Claim
13 words
The composition of claim 2, wherein said mono-functional short-chain monomer comprises 4-methoxycarbonylamino-2-(2-methacryloxy) ethoxycarbonylaminotoluene.
Claim 30
Dependent Claim
13 words
The composition of claim 2, wherein said mono-functional short-chain monomer comprises 4-isopentoxycarbonylamino-2-(2-methacryloxy) ethoxycarbonylaminotoluene.
Claim 31
Dependent Claim
18 words
The composition of claim 2, wherein said mono-functional short-chain monomer comprises 3(p-tertiary butyl) phenoxy-2-hydroxy propyl methacrylate or acrylate.
Claim 32
Dependent Claim
18 words
The composition of claim 2, wherein said polyfunctional prepolymer comprises the dimaleate half ester of polydiethylene glycol adipate.
Claim 33
Dependent Claim
16 words
The composition of claim 1, wherein said polyfunctional prepolymer comprises the diallylurethane of polydiethylene glycol adipate.
Claim 34
Dependent Claim
16 words
The composition of claim 2, wherein said polyfunctional prepolymer comprises the dimethacrylate of polydiethylene glycol adipate.
Claim 35
Dependent Claim
13 words
The composition of claim 2, wherein said monofunctional monomer comprises 2-methacryloxyethyl phenyl urethane.
Claim 36
Dependent Claim
12 words
The composition according to claim 1, an optionally including a chelating agent.
Claim 37
Dependent Claim
19 words
The composition of claim 1, and comprising from about 50 to about 98 mole percent of cross-link controlling material.
Claim 38
Dependent Claim
19 words
The composition of claim 36, and comprising from about 91 to about 95 mole percent of cross-link controlling material.
Claim 39
Independent Claim
78 words
A method of forming an elastomeric material, comprising the steps of (1) providing a cure-to-elastomer composition which comprises at least one moderate-to-long chain di or polyfunctional prepolymer having vinyl reactive ends; and at least one cross-link controlling material which is (i) reactive with said moderate-to-long chain di or polyfunctional prepolymer, and (ii) soluble in or miscible with said moderate-to-long chain prepolymer; and (2) curing the composition of step (1) in the presence of a free radical polymerization initiator.
Claim 40
Independent Claim
78 words
A method of forming an elastomeric material, comprising the steps of (1) providing a cure-to-elastomer composition which comprises at least one moderate-to-long chain di or polyfunctional prepolymer having vinyl reactive ends; and at least one cross-link controlling material which is (i) reactive with said moderate-to-long chain di or polyfunctional prepolymer, and (ii) soluble in or miscible with said moderate-to-long chain prepolymer; and (2) curing the composition of step (1) in the presence of a free radical polymerization initiator.
Claim 41
Dependent Claim
26 words
The method of claim 38, wherein said cross-link controlling material comprises a monofunctional short chain monomer, a polymerization chain transfer coupling agent, or a mixture thereof.
Claim 42
Dependent Claim
28 words
The method of claim 38, wherein said moderate-to-long chain polyfunctional prepolymer comprises a polyether-urethane-acrylate, a polyether-urethane methacrylate, a polyester-urethane acrylate, a polyester-urethane-methacrylate, or an allyl alcohol derivative thereof.
Claim 43
Dependent Claim
17 words
The method of claim 40, wherein the polyester portion of said polyester-urethane methacrylate comprises a polyester diol.
Claim 44
Dependent Claim
19 words
The method of claim 41, wherein said polyester diol comprises the reaction product of diethylene glycol and adipic acid.
Claim 45
Dependent Claim
22 words
The method of claim 41, wherein said polyester diol comprises the reaction product of neopentyl glycol and 1,6-hexane diol with adipic acid.
Claim 46
Dependent Claim
18 words
The composition of claim 40, wherein the polyether portion of said polyether-urethane-acrylate or -methacrylate comprises a polyether diol.
Claim 47
Dependent Claim
19 words
The composition of claim 44, wherein said polyether diol comprises a polyether with a 1,4 butylene oxide repeat unit.
Claim 48
Dependent Claim
36 words
The method of claim 38, wherein said moderate-to-long chain polyfunctional prepolymer comprises a difunctional monomer selected from the group consisting of a dimaleate half ester of polydiethylene glycol adipate and a dimethacrylate of polydiethylene glycol adipate.
Claim 49
Dependent Claim
20 words
The method of claim 36, wherein said moderate-to-long chain polyfunctional prepolymer comprises a diallyl urethane of polydiethylene glycol adipate polyester.
Claim 50
Dependent Claim
21 words
A method of claim 36, wherein said free radical catalyst system comprises a free-radical initiator and an accelerator of free-radical polymerization.
Claim 51
Dependent Claim
22 words
A method of claim 48, wherein said free-radical initiator is selected from the group consisting of organic peroxides, hydroperoxides, peresters and peracids.
Claim 52
Dependent Claim
14 words
The method of claim 49, wherein said perester free radical initiator comprises t-butyl perbenzoate.
Claim 53
Dependent Claim
13 words
The method of claim 49, wherein said free radical initiator comprises cumene hydroperoxide.
Claim 54
Dependent Claim
34 words
The method of claim 38, wherein said free-radical initiator is of the photoinitiator-type, and including the step of exposing said compositions to light of wave length and intensity to effect cure of said composition.
Claim 55
Dependent Claim
26 words
The method of claim 38, wherein said polymerization initiator comprises 0.1 to 10 percent by weight of the combination of said polymerizable monomers and said initiator.
Claim 56
Dependent Claim
30 words
A method of claim 38, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of monomethacrylate and monoacrylate esters of aryl, alkyl and arylalkyl alcohols.
Claim 57
Dependent Claim
29 words
The method of claim 38, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of arylamino, alkylamino and arylalkyl amino methacrylate and acrylate esters.
Claim 58
Dependent Claim
38 words
The method of claim 38, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of the reaction products of phenyl glycidyl ether and methacrylic acid or acrylic acid, 3-phenoxy-2-hydroxypropyl methacrylate and 3-phenoxy-2-hydroxypropyl acrylate.
Claim 59
Dependent Claim
49 words
The method of claim 38, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of the reaction products of methacrylic acid or acrylic acid with para-tertiary butyl phenyl glycidyl ether, ortho-cresyl glycidyl ether, butyl glycidyl ether and the glycidyl ethers of decane to octadecane.
Claim 60
Dependent Claim
47 words
The method of claim 38, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of glycidyl acrylate and methacrylate esters, mixed esters of glycerol 1-(2-ethyl) hexanoate-3-methacrylate and glycerol 1-(2-ethyl) hexanoate-3-acrylate prepared by reacting glycidyl methacrylate or glycidyl acrylate and 2-ethyl hexanoic acid.
Claim 61
Dependent Claim
32 words
The method of claim 38, wherein said cross-link controlling material comprises a co-reactive monomer selected from a group consisting of the reaction products of 1-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, 2-hydroxypropylmethacrylate and 2-hydroxypropylacrylate and an isocyanate.
Claim 62
Dependent Claim
49 words
The method of claim 38, wherein said cross-link controlling material comprises a co-reactive monomer selected from the group consisting of the reaction products of 2-hydroxyethylmethacrylate and methanol with toluene diisocyanate, 2-hydroxypropyl methacrylate and methanol with toluene diisocyanate; 2-hydroxyethylmethacrylate and isopentyl alcohol with 2,4 toluenediisocyanate; and 2-hydroxyethyl methacrylate with phenylisocyanate.
Claim 63
Dependent Claim
36 words
The method of claim 38, wherein said cross-link controlling material comprises a polymerization chain transfer and coupling agent selected from the group consisting of the dimercaptoacetates and substituted dimercaptocarboxycylic acid esters of glycol polyethers and polyesters.
Claim 64
Dependent Claim
17 words
The method of claim 61, wherein said polymerization chain transfer and coupling agent comprises triethylene glycol dimercaptoacetate.
Claim 65
Dependent Claim
17 words
The method of claim 61, wherein said polymerization chain transfer and coupling agent comprises triethylene glycol dimercaptopropionate.
Claim 66
Dependent Claim
20 words
The method of claim 61, wherein said polymerization chain transfer and coupling agent comprises the dimercaptoproprionate of polydiethylene glycol adipate.
Claim 67
Dependent Claim
13 words
The method of claim 39, wherein said mono-functional short-chain monomer comprises 4-methoxycarbonylamino-2-(2-methacryloxy) ethoxycarbonylaminotoluene.
Claim 68
Dependent Claim
13 words
The method of claim 39, wherein said mono-functional short-chain monomer comprises 4-isopentoxycarbonylamino-2-(2-methacryloxy) ethoxycarbonylaminotoluene.
Claim 69
Dependent Claim
16 words
The method of claim 39, wherein said mono-functional short-chain monomer comprises 3(p-tertiary butyl) phenoxy-2-hydroxy propyl methacrylateacrylate.
Claim 70
Dependent Claim
18 words
The method of claim 38, wherein said polyfunctional prepolymer comprises the dimaleate half ester of polydiethylene glycol adipate.
Claim 71
Dependent Claim
16 words
The method of claim 38, wherein said polyfunctional prepolymer comprises the diallylurethane of polydiethylene glycol adipate.
Claim 72
Dependent Claim
16 words
The method of claim 38, wherein said polyfunctional prepolymer comprises the dimethacrylate of polydiethylene glycol adipate.
Claim 73
Dependent Claim
13 words
The method of claim 39, wherein said monofunctional monomer comprises 2-methacryloxyethyl phenyl urethane.
Claim 74
Dependent Claim
13 words
The method of claim 38 and including a chelating agent in said composition.
Claim 75
Dependent Claim
26 words
The method of claim 38, wherein said composition comprises from about 50 to about 98 mole percent of cross-link controlling material for each mole of prepolymer.
Claim 76
Dependent Claim
26 words
The method of claim 73, wherein said composition comprises from about 91 to about 95 mole percent of cross-link controlling material for each mole of prepolymer.
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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) | 1987-03-27 | 1987-09-26 | 1988-03-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-27 | 1991-09-26 | 1992-03-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-27 | 1995-09-26 | 1996-03-27 | $7700.00 | Window Closed / Lapsed |