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US4238397A Expired / Lapsed US ⏱️ 0.0 years remaining

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
•
Filing: 1979-05-18
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Granted: 1980-12-09
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Expires: 1999-05-18
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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 2026-10-25 10:50
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/38; C08F36/00

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 223 words
A product of 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 ##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 formula 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 223 words
A product of 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 ##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 formula 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 product 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 product of claim 2 wherein said hydroxyl-containing disulfide and trisulfide have 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 24 words
A product of claim 3 wherein said vinylidene monomer has copolymerized therewith from 0 about 40 wt.% of at least one copolymerizable ethylenic monomer.
Claim 6
Dependent Claim 89 words
A product 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 product 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 product 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 product 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 product of claim 8 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
Claim 11
Dependent Claim 27 words
A product 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 product of claim 10 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
Claim 13
Dependent Claim 29 words
A product 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 product of claim 12 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
Claim 15
Dependent Claim 28 words
A product 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 product of claim 14 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.
Claim 17
Dependent Claim 29 words
A product 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 acrylic acid.
Claim 18
Dependent Claim 15 words
A product of claim 16 wherein said hydroxyl-containing ester of acrylic acid is 2-hydroxyethyl acrylate.

References Cited (Backward Citations)

US3470146A Cited
US3712916A Cited
US3699153A Cited
US3910992A Cited
US4013710A Cited
US4122056A Cited
US4120766A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-12-09 1984-06-09 1984-12-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-12-09 1988-06-09 1988-12-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-12-09 1992-06-09 1992-12-09 $7700.00 Window Closed / Lapsed

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