US4207238A
Expired / Lapsed
US
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Hydroxyl-terminated liquid polymers and process for preparation thereof using a mixture of at least one hydroxyl-containing disulfide and at least one hydroxyl-containing trisulfide
Assignee: Goodrich Corp
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Filing: 1977-09-01
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Granted: 1980-06-10
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Expires: 1997-09-01
Abstract
Abstract Hydroxyl-terminated liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one vinylidene monomer having at least one terminal CH 2 ═C< group per monomer molecule, together with (2) a mixture of at least one hydroxyl-containing disulfide and at least one hydroxyl-containing trisulfide. Use of the above disulfide-trisulfide mixture permits viscosity control during polymerization with substantially less disulfide required than if the disulfide alone were used, and the resulting polymers have less odor and discolor less upon heating than if the disulfide alone were used.
Inventors
- 👤 Jack C. Gilles
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 19:58
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/38; C08F36/00
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
231 words
A process for preparing a hydroxyl-terminated liquid polymer having an aliphatic polymeric backbone, said process comprising thermal polymerization in a single step of (1) at least one vinylidene monomer having at least one terminal CH 2 ═C< group, together with (2) at least one hydroxyl-containing disulfide having the formula HO(C.sub.n H.sub.2n O).sub.m (C.sub.n H.sub.2n).sub.p --(S).sub.g --(C.sub.n H.sub.2n).sub.p (OC.sub.n H.sub.2n).sub.m OH or ##STR9## wherein m is an integer from 0 to 10, n and p are integers from 1 to 10, and g is 2, and (3) at least one hydroxyl-containing trisulfide having the formulas above, except that g is 3, the amount of said trisulfide constituting from about 1 wt.% to about 25 wt.% of the total amount of said trisulfide and disulfide, wherein (4) said vinylidene monomer is selected from the group consisting of (a) monoolefins containing 2 to 14 carbon atoms, (b) dienes containing 4 to 10 carbon atoms, (c) vinyl and allyl esters of carboxylic acids containing 2 to 8 carbon atoms, (d) vinyl and allyl ethers of alkyl radicals containing 1 to 8 carbon atoms, and (e) acrylic acids and acrylates having the formula ##STR10## said R being hydrogen or an alkyl radical containing 1 to 3 carbon atoms, and R 1 being hydrogen or an alkyl radical containing 1 to 18 carbon atoms, or an alkoxyalkyl, alkylthioalkyl or cyanoalkyl radical containing 2 to 12 carbon atoms.
Claim 2
Dependent Claim
231 words
A process for preparing a hydroxyl-terminated liquid polymer having an aliphatic polymeric backbone, said process comprising thermal polymerization in a single step of (1) at least one vinylidene monomer having at least one terminal CH 2 ═C< group, together with (2) at least one hydroxyl-containing disulfide having the formula HO(C.sub.n H.sub.2n O).sub.m (C.sub.n H.sub.2n).sub.p --(S).sub.g --(C.sub.n H.sub.2n).sub.p (OC.sub.n H.sub.2n).sub.m OH or ##STR9## wherein m is an integer from 0 to 10, n and p are integers from 1 to 10, and g is 2, and (3) at least one hydroxyl-containing trisulfide having the formulas above, except that g is 3, the amount of said trisulfide constituting from about 1 wt.% to about 25 wt.% of the total amount of said trisulfide and disulfide, wherein (4) said vinylidene monomer is selected from the group consisting of (a) monoolefins containing 2 to 14 carbon atoms, (b) dienes containing 4 to 10 carbon atoms, (c) vinyl and allyl esters of carboxylic acids containing 2 to 8 carbon atoms, (d) vinyl and allyl ethers of alkyl radicals containing 1 to 8 carbon atoms, and (e) acrylic acids and acrylates having the formula ##STR10## said R being hydrogen or an alkyl radical containing 1 to 3 carbon atoms, and R 1 being hydrogen or an alkyl radical containing 1 to 18 carbon atoms, or an alkoxyalkyl, alkylthioalkyl or cyanoalkyl radical containing 2 to 12 carbon atoms.
Claim 3
Dependent Claim
102 words
A process of claim 1 wherein m is an integer from 0 to 4, n and p are integers from 1 to 4, and said vinylidene monomer is selected from the group consisting of (a) monoolefins containing 2 to 8 carbon atoms, (b) dienes containing 4 to 8 carbon atoms, and (e) acrylic acids and acrylates having the formula ##STR11## said R being hydrogen or an alkyl radical containing 1 to 3 carbon atoms, and said R 1 being hydrogen, an alkyl radical containing 1 to 8 carbon atoms, or an alkoxyalkyl, alkylthioalkyl or cyanoalkyl radical containing 2 to 8 carbon atoms.
Claim 4
Dependent Claim
55 words
A process of claim 2 wherein said hydroxyl-containing disulfide and trisulfide having the formula HO(C.sub.n H.sub.2n O).sub.m (C.sub.n H.sub.2n).sub.p --(S).sub.g --(C.sub.n H.sub.2n).sub.p (OC.sub.n H.sub.2n).sub.m OH wherein m is an integer from 0 to 4, n and p are integers from 1 to 4, and g is 2 and 3 for the disulfide and trisulfide respectively.
Claim 5
Dependent Claim
25 words
A process of claim 3 wherein said vinylidene monomer has copolymerized therewith from 0 to about 40 wt.% of at least one copolymerizable ethylenic monomer.
Claim 6
Dependent Claim
89 words
A process of claim 4 wherein said copolymerizable ethylenic monomer is selected from the group consisting of (f) vinyl aromatics having the formula ##STR12## wherein R 2 is hydrogen, halogen or an alkyl radical containing 1 to 4 carbon atoms, (g) vinyl nitriles having the formula ##STR13## wherein R 3 is hydrogen or an alkyl radical containing 1 to 3 carbon atoms (h) divinyls and diacrylates, (i) amides of α,β-olefinically unsaturated carboxylic acids containing 2 to 8 carbon atoms, (j) hydroxyl-containing vinylidene monomers, and (k) N-vinyl-2-pyrrolidone and diacetone acrylamide.
Claim 7
Dependent Claim
43 words
A process of claim 5 wherein said vinylidene monomer is selected from the group consisting of n-butyl acrylate, ethyl acrylate and butadiene, and said ethylenic comonomer is selected from the group consisting of acrylonitrile, N-vinyl-2-pyrrolidone, diacetone acrylamide and hydroxyl-containing esters of acrylic acid.
Claim 8
Dependent Claim
18 words
A process of claim 6 wherein said hydroxyl-containing disulfide and trisulfide are 2-hydroxyethyl disulfide and 2-hydroxyethyl trisulfide respectively.
Claim 9
Dependent Claim
28 words
A process of claim 7 wherein the backbone of said alkyl acrylate liquid polymer contains polymerized therein n-butyl acrylate, butadiene, N-vinyl-2-pyrrolidone and a hydroxyl-containing ester of acrylic acid.
Claim 10
Dependent Claim
15 words
A process of claim 8 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
Claim 11
Dependent Claim
27 words
A process of claim 7 wherein the backbone of said alkyl acrylate liquid polymer contains polymerized therein n-butyl acrylate, N-vinyl-2-pyrrolidone and a hydroxyl-containing ester of acrylic acid.
Claim 12
Dependent Claim
15 words
A process of claim 10 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
Claim 13
Dependent Claim
29 words
A process of claim 7 wherein the backbone of said alkyl acrylate liquid polymer contains polymerized therein n-butyl acrylate, ethyl acrylate, N-vinyl-2-pyrrolidone, and a hydroxyl-containing ester of acrylic acid.
Claim 14
Dependent Claim
15 words
A process of claim 12 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
Claim 15
Dependent Claim
28 words
A process of claim 7 wherein the backbone of said alkyl acrylate liquid polymer contains polymerized therein n-butyl acrylate, acrylonitrile, N-vinyl-2-pyrrolidone, and a hydroxyl-containing ester of acrylic acid.
Claim 16
Dependent Claim
15 words
A process of claim 14 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
Claim 17
Dependent Claim
29 words
A process of claim 7 wherein the backbone of said alkyl acrylate liquid polymer contains polymerized therein n-butyl acrylate, ethyl acrylate, acrylonitrile and a hydroxyl-containing ester of acrylate acid.
Claim 18
Dependent Claim
15 words
A process of claim 16 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
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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) | 1983-06-10 | 1983-12-10 | 1984-06-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-06-10 | 1987-12-10 | 1988-06-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-06-10 | 1991-12-10 | 1992-06-10 | $7700.00 | Window Closed / Lapsed |