US5493041A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Lightly crosslinked poly(n-alkylmethylsiloxanes) and methods of producing same
Assignee: Dow Silicones Corp
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Filing: 1995-07-21
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Granted: 1996-02-20
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Expires: 2015-07-21
Abstract
Abstract The crosslinking and simultaneous alkylation of poly(hydridomethylsiloxanes) form crosslinked siloxanes having n-alkylmethyl groups. Without changing the chain length of the poly(hydridomethylsiloxane) starting material, a family of lightly crosslinked siloxanes having n-alkylmethyl groups, with a range of viscosities, can be produced using one or more alpha-olefins along with a small amount of an unconjugated alpha, omega-diene added as a crosslinker. The poly(hydridomethyl siloxanes) are made from highly pure silanol-free hexamethyldisiloxane and highly pure mixtures of silanol-free tetramethylcyclotetrasiloxane (D H 4) and pentamethylcyclopentasiloxane D H 5 containing no more than about 100 parts per million (ppm) water, with anhydrous trifluoromethane sulfonic acid (triflic acid, CF 3 SO 3 H), at room temperature, to provide linear poly(hydridomethylsiloxanes) having degrees of polymerization of up to about 250.
Inventors
- 👤 Timothy N. Biggs
- 👤 Gary E. Legrow
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:13
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C08G77/12; C08G77/48; C08G77/50
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
60 words
A method of making crosslinked siloxanes having n-alkylmethyl groups comprising the steps of (i) forming a reaction mixture containing at least one alpha-olefin, a crosslinker, and a catalyst, (i) contacting the reaction mixture with at least one substantially pure poly(hydridomethylsiloxane), and (iii) agitating the mixture and the catalyst at below 150° C. to form a crosslinked siloxane having n-alkylmethyl groups.
Claim 2
Independent Claim
60 words
A method of making crosslinked siloxanes having n-alkylmethyl groups comprising the steps of (i) forming a reaction mixture containing at least one alpha-olefin, a crosslinker, and a catalyst, (i) contacting the reaction mixture with at least one substantially pure poly(hydridomethylsiloxane), and (iii) agitating the mixture and the catalyst at below 150° C. to form a crosslinked siloxane having n-alkylmethyl groups.
Claim 3
Dependent Claim
17 words
A method according to claim 1 in which the alpha-olefin is 1-hexene and the crosslinker is 1,5-hexadiene.
Claim 4
Dependent Claim
17 words
A method according to claim 1 in which the alpha-olefin is 1-octadecene and the crosslinker is 1,5-hexadiene.
Claim 5
Dependent Claim
22 words
A method according to claim 1 in which the alpha-olefin is a mixture of 1-hexene and 1-octadecene and the crosslinker is 1,5-hexadiene.
Claim 6
Dependent Claim
69 words
A method according to claim 1 in which the substantially pure poly(hydridomethylsiloxane) is made by the method comprising (i) forming a reaction mixture containing a silanol-free hexaorganodisiloxane, one or more silanol-free methylhydrogen cyclosiloxanes, and less than about 100 parts per million water, (ii) contacting the reaction mixture with anhydrous trifluoromethane sulfonic acid catalyst, and (iii) agitating the mixture and the catalyst at below 100° C. to form a poly(hydridomethylsiloxane).
Claim 7
Dependent Claim
22 words
A method according to claim 1 in which the substantially pure poly(hydridomethylsiloxane) has a degree of polymerization of about 8 to 250.
Claim 8
Dependent Claim
20 words
A method according to claim 6 in which the substantially pure poly(hydridomethylsiloxane) has a degree of polymerization of about 9.6.
Claim 9
Dependent Claim
20 words
A method according to claim 6 in which the substantially pure poly(hydridomethylsiloxane) has a degree of polymerization of about 60.
Claim 10
Dependent Claim
56 words
A method according to claim 1 in which the alpha-olefin is an alkene selected from the group consisting of ethylene, propene, 1-butene, isobutylene (2-methylpropene), 1-pentene (C5), 2-methyl-1-butene, 3-methyl-1-butene, 1-hexene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 1-heptene, 2-methyl-1-hexene, 1-octene, 2-methyl-1-heptene, 1-nonene, 1-decene (C10), 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene (C15), 1-hexadecene, 1-octadecene, 1-nonadecene, 1-eicosene (C20), and alpha-olefin fractions containing C22-C30+ alpha-olefins.
Claim 11
Dependent Claim
11 words
A crosslinked siloxane prepared according to the method in claim 1.
Claim 12
Dependent Claim
19 words
A crosslinked siloxane comprising at least one substantially pure poly(hydridomethylsiloxane), at least one alpha-olefin, a crosslinker, and a catalyst.
Claim 13
Dependent Claim
19 words
A crosslinked siloxane comprising at least one substantially pure poly(hydridomethylsiloxane), at least one alpha-olefin, a crosslinker, and a catalyst.
Claim 14
Dependent Claim
17 words
The crosslinked siloxane of claim 11 in which the alpha-olefin is 1-hexene and the crosslinker is 1,5-hexadiene.
Claim 15
Dependent Claim
17 words
The crosslinked siloxane of claim 11 in which the alpha-olefin is 1-octadecene and the crosslinker is 1,5-hexadiene.
Claim 16
Dependent Claim
22 words
The crosslinked siloxane of claim 11 in which the alpha-olefin is a mixture of 1-hexene and 1-octadecene and the crosslinker is 1,5-hexadiene.
Claim 17
Dependent Claim
70 words
The crosslinked siloxane of claim 11 in which the substantially pure poly(hydridomethylsiloxane) is made by the method comprising (i) forming a reaction mixture containing a silanol-free hexaorganodisiloxane, one or more silanol-free methylhydrogen cyclosiloxanes, and less than about 100 parts per million water, (ii) contacting the reaction mixture with anhydrous trifluoromethane sulfonic acid catalyst, and (iii) agitating the mixture and the catalyst at below 100° C. to form a poly (hydridomethylsiloxane).
Claim 18
Dependent Claim
22 words
The crosslinked siloxane of claim 11 in which the substantially pure poly(hydridomethylsiloxane) has a degree of polymerization of about 8 to 250.
Claim 19
Dependent Claim
20 words
The crosslinked siloxane of claim 16 in which the substantially pure poly(hydridomethylsiloxane) has a degree of polymerization of about 9.6.
Claim 20
Dependent Claim
20 words
The crosslinked siloxane of claim 16 in which the substantially pure poly(hydridomethylsiloxane) has a degree of polymerization of about 60.
Claim 21
Dependent Claim
56 words
The crosslinked siloxane claim 11 in which the alpha-olefin is an alkene selected from the group consisting of ethylene, propene, 1-butene, isobutylene (2-methylpropene), 1-pentene (C5), 2-methyl-1-butene, 3-methyl-1-butene, 1-hexene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 1-heptene, 2-methyl-1-hexene, 1-octene, 2-methyl-1-heptene, 1-nonene, 1-decene (C10), 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene (C15), 1-hexadecene, 1-octadecene, 1-nonadecene, 1-eicosene ( C20), and alpha-olefin fractions containing C22-C30+ alpha-olefins.
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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) | 1999-02-19 | 1999-08-21 | 2000-02-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-02-19 | 2003-08-21 | 2004-02-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-02-19 | 2007-08-21 | 2008-02-20 | $7700.00 | Window Closed / Lapsed |