US4387177A
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Room temperature curable organopolysiloxane compositions and methods for their preparation
Assignee: DuPont Toray Specialty Materials KK
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Filing: 1982-02-02
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Granted: 1983-06-07
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Expires: 2002-02-02
Abstract
Abstract A low modulus silicone rubber which cures at room temperature can be obtained by exposing a composition made from a hydroxyl endblocked polydiorganosiloxane, an aminoxy silicon compound having two aminoxy groups per molecule, such as, methylvinyldi-(N,N-diethylaminoxy)silane, and a hydrolyzable organosilicon compound which has at least three hydrolyzable groups per molecule including oxime, alkoxy, amino, vinyloxy, amide, imide, and lactam such as methyltri(N-methylacetamido)silane or methyltrimethoxysilane. The compositions can be packaged in a single container and, if sealed, remain stable until exposed to moisture. The compositions can be made by a two-step method comprising mixing the aminoxy silicon compound and the hydroxyl endblocked polydiorganosiloxane and thereafter blending in the hydrolyzable organosilicon compound.
Inventors
- 👤 Katsutoshi Mine
- 👤 Tadao Tamaki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:25
CPC Classifications
C; C08; C08L; C08L83/00; C08L83/04; C08G; C08G77/00; C08G77/04; C08G77/045; C08G77/14; C08G77/16; C08G77/22; C08G77/24; C08G77/26
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
184 words
A room temperature curable organopolysiloxane composition comprising the product obtained by mixing (A) 100 parts by weight of a hydroxyl endblocked polydiorganosiloxane having a viscosity at 25° C. in the range 0.00005 to 0.5 m 2 /s inclusive and in which the organic radicals are monovalent radicals selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, (B) an amount of an aminoxy organosilicon compound sufficient to provide at least one mol aminoxy group per one mol hydroxyl group in (A), the aminoxy organosilicon compound having a general formula ##STR23## in which each R, R', and R 2 is a monovalent radical selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, n has a value of from 1 to 50 inclusive, and p has a value of from 1 to 5 inclusive, (C) from 0.5 to 20 parts by weight of a hydrolyzable organosilicon compound containing at least three silicon-bonded hydrolyzable groups per molecule, said hydrolyzable groups being selected from the group consisting of oxime groups, alkoxy groups, amino groups, vinyloxy groups, amide groups, imide groups, and lactam groups.
Claim 2
Dependent Claim
184 words
A room temperature curable organopolysiloxane composition comprising the product obtained by mixing (A) 100 parts by weight of a hydroxyl endblocked polydiorganosiloxane having a viscosity at 25° C. in the range 0.00005 to 0.5 m 2 /s inclusive and in which the organic radicals are monovalent radicals selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, (B) an amount of an aminoxy organosilicon compound sufficient to provide at least one mol aminoxy group per one mol hydroxyl group in (A), the aminoxy organosilicon compound having a general formula ##STR23## in which each R, R', and R 2 is a monovalent radical selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, n has a value of from 1 to 50 inclusive, and p has a value of from 1 to 5 inclusive, (C) from 0.5 to 20 parts by weight of a hydrolyzable organosilicon compound containing at least three silicon-bonded hydrolyzable groups per molecule, said hydrolyzable groups being selected from the group consisting of oxime groups, alkoxy groups, amino groups, vinyloxy groups, amide groups, imide groups, and lactam groups.
Claim 3
Dependent Claim
30 words
The room temperature curable organopolysiloxane composition according to claim 1 in which (A), (B), and (C) are mixed and stored under conditions excluding moisture, but cure when exposed to moisture.
Claim 4
Dependent Claim
12 words
The composition according to claim 1 in which a filler is present.
Claim 5
Dependent Claim
12 words
The composition according to claim 2 in which a filler is present.
Claim 6
Dependent Claim
68 words
The composition according to claim 2 in which the hydroxyl endblocked polydiorganosiloxane of (A) has a viscosity at 25° C. in the range of 0.00005 to 0.05 m 2 /s inclusive, the amount of aminoxy silicon compound in (B) is sufficient to provide from 2 to 15 inclusive mols of aminoxy group per one mol of hydroxyl group in (A), and a catalyst, (D), for curing, is present.
Claim 7
Dependent Claim
60 words
The composition according to claim 4 in which the hydroxyl endblocked polydiorganosiloxane of (A) has a viscosity at 25° C. in the range of 0.00005 to 0.05 m 2 /s inclusive, the amount of aminoxy silicon compound in (B) is sufficient to provide from 2 to 15 inclusive mols of aminoxy group per one mol of hydroxyl group in (A).
Claim 8
Dependent Claim
27 words
The composition according to claim 6 in which the hydrolyzable organosilicon compound of (C) is present in an amount of 2 to 10 parts by weight inclusive.
Claim 9
Dependent Claim
20 words
The composition according to claim 7 in which the organic radicals of the hydroxyl endblocked polydiorganosiloxane in (A) are methyl.
Claim 10
Dependent Claim
45 words
The composition according to claim 8 in which the aminoxy silicon compound of (B) is a compound of the formula (CH.sub.3)(CH.sub.2 ═CH)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is the compound of the formula CH.sub.2 ═CHSi[ON═C(CH.sub.3)(CH.sub.2 CH.sub.3)].sub.3, and the filler is calcium carbonate.
Claim 11
Dependent Claim
15 words
The composition according to claim 6 in which a catalyst, (D), for curing, is present.
Claim 12
Dependent Claim
27 words
The composition according to claim 10 in which the hydrolyzable organosilicon compound of (C) is present in an amount of 2 to 10 parts by weight inclusive.
Claim 13
Dependent Claim
20 words
The composition according to claim 11 in which the organic radicals of the hydroxyl endblocked polydiorganosiloxane in (A) are methyl.
Claim 14
Dependent Claim
43 words
The composition according to claim 12 in which the aminoxy silicon compund of (B) is the compound of the formula (CH.sub.3)(CH.sub.2 ═CH)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is methyltrimethoxysilane, the catalyst, (D), is tetrabutyltitanate, and the filler is calcium carbonate.
Claim 15
Dependent Claim
53 words
The composition according to claim 12 in which the aminoxy silicon compound of (B) is the compound of the formula (CH.sub.3)(CH.sub.2 ═CH)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is a compound represented by the formula CH.sub.3 Si[N(CH.sub.3)(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3)].sub.3, the catalyst, (D), is dibutyltindioctoate, and the filler is calcium carbonate.
Claim 16
Dependent Claim
49 words
The composition according to claim 12 in which the aminoxy silicon compound of (B) is the compound of the formula (CH.sub.3)(CH.sub.2 ═CH)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is a compound represented by the formula ##STR24## the catalyst, (D), is dibutylindioctoate, and the filler is calcium carbonate.
Claim 17
Dependent Claim
49 words
The composition according to claim 12 in which the aminoxy silicon compound of (B) is the compound of the formula (CH.sub.3)(CH.sub.2 ═CH)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is a compound represented by the formula ##STR25## the catalyst, (D), is dibutyltindilaurate, and the filler is calcium carbonate.
Claim 18
Dependent Claim
50 words
The composition according to claim 12 in which the aminoxy silicon compound of (B) is the compound of the formula (CH.sub.3)(CH.sub.2 ═CH)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is a compound represented by the formula CH.sub.3 Si[N═C(CH.sub.3)(OCH.sub.3)].sub.3, the catalyst, (D), is dibutyltindilaurate, and the filler is calcium carbonate.
Claim 19
Dependent Claim
49 words
The composition according to claim 12 in which the aminoxy silicon compound of (B) is the compound of the formula (CH.sub.3)(CH.sub.2 ═CH)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is a compound represented by the formula ##STR26## the catalyst, (D), is dibutyltindilaurate, and the filler is calcium carbonate.
Claim 20
Dependent Claim
22 words
The composition according to claim 11 in which the organic radicals of the hydroxyl endblocked polydiorganosiloxane in (A) are methyl and phenyl.
Claim 21
Dependent Claim
52 words
The composition according to claim 19 in which the aminoxy silicon compound of (B) is the compound of the formula (C.sub.6 H.sub.5)(CH.sub.3)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is a compound represented by the formula CH.sub.2 ═CHSi[ON═C(CH.sub.2 CH.sub.3).sub.2 ].sub.3, the catalyst, (D), is dibutyltindilaurate, and the filler is calcium carbonate.
Claim 22
Dependent Claim
54 words
The composition according to claim 19 in which the aminoxy silicon compound of (B) is the compound of the formula (CH.sub.3 CH.sub.2).sub.2 NO[(CH.sub.3).sub.2 SiO].sub.4 N(CH.sub.2 CH.sub.3).sub.2, the hydrolyzable organosilicon compound of (C) is a compound represented by the formula (CH.sub.2 ═CH)Si[ON═C(CH.sub.2 CH.sub.3).sub.2 ].sub.3, the catalyst, (D), is dibutyltindilaurate, and the filler is calcium carbonate.
Claim 23
Dependent Claim
43 words
The composition according to claim 19 in which the aminoxy silicon compound of (B) is the compound of the formula (C.sub.6 H.sub.5)(CH.sub.3)Si[ON(CH.sub.2 CH.sub.3).sub.2 ].sub.2, the hydrolyzable organosilicon compound of (C) is methyltrimethoxysilane, the catalyst, (D), is tetrabutyltitanate, and the filler is calcium carbonate.
Claim 24
Dependent Claim
45 words
The composition according to claim 19 in which the aminoxy silicon compound of (B) is the compound of the formula (CH.sub.3 CH.sub.2).sub.2 NO[(CH.sub.3).sub.2 SiO].sub.4 N(CH.sub.2 CH.sub.3).sub.2, the hydrolyzable organsilicon compound of (C) is methyltrimethoxysilane, the catalyst, (D), is tetrabutyltitanate, and the filler is calcium carbonate.
Claim 25
Independent Claim
228 words
A method of making a room temperature curable organopolysiloxane composition comprising (I) mixing under essentially anhydrous conditions to form a homogeneous blend (A) 100 parts by weight of a hydroxyl endblocked polydiorganosiloxane having a viscosity at 25° C. in the range of 0.00005 to 0.5 m 2 /s inclusive and in which the organic radicals are monovalent radicals selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, and (B) an amount of an aminoxy organosilicon compound sufficient to provide 2 to 15 mols of aminoxy group per mol of hydroxyl group in (A), the aminoxy organosilicon compound having a general formula ##STR27## in which each R, R', and R 2 is a monovalent radical selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, n has a value of from 1 to 50 inclusive, and p has a value of from 1 to 5 inclusive, (II) blending with the homogeneous blend of (I) under essentially anhydrous conditions, (C) from 0.5 to 20 parts by weight of a hydrolyzable organosilicon compound containing at least three silicon-bonded hydrolyzable groups per molecule, said hydrolyzable groups being selected from the group consisting of oxime groups, alkoxy groups, amino groups, vinyloxy groups, amide groups, imide groups, and lactam groups, and thereafter (III) placing the resulting product of (II) in a storage container which provides essentially anhydrous storage conditions.
Claim 26
Independent Claim
228 words
A method of making a room temperature curable organopolysiloxane composition comprising (I) mixing under essentially anhydrous conditions to form a homogeneous blend (A) 100 parts by weight of a hydroxyl endblocked polydiorganosiloxane having a viscosity at 25° C. in the range of 0.00005 to 0.5 m 2 /s inclusive and in which the organic radicals are monovalent radicals selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, and (B) an amount of an aminoxy organosilicon compound sufficient to provide 2 to 15 mols of aminoxy group per mol of hydroxyl group in (A), the aminoxy organosilicon compound having a general formula ##STR27## in which each R, R', and R 2 is a monovalent radical selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, n has a value of from 1 to 50 inclusive, and p has a value of from 1 to 5 inclusive, (II) blending with the homogeneous blend of (I) under essentially anhydrous conditions, (C) from 0.5 to 20 parts by weight of a hydrolyzable organosilicon compound containing at least three silicon-bonded hydrolyzable groups per molecule, said hydrolyzable groups being selected from the group consisting of oxime groups, alkoxy groups, amino groups, vinyloxy groups, amide groups, imide groups, and lactam groups, and thereafter (III) placing the resulting product of (II) in a storage container which provides essentially anhydrous storage conditions.
Claim 27
Independent Claim
192 words
A method of making a room temperature curable organopolysiloxane composition comprising (I) mixing (B) an amount of aminoxy organosilicon compound sufficient to provide at least one mol aminoxy group per one mol hydroxyl group in (A), the aminoxy organosilicon compound having a general formula ##STR28## in which each R, R', and R 2 is a monovalent radical selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, n has a value of from 1 to 50 inclusive, and p has a value of from 1 to 5 inclusive, (C) from 0.5 to 20 parts by weight of a hydrolyzable organosilicon compound containing at least three silicon-bonded hydrolyzable groups per molecule, said hydrolyzable groups being selected from the group consisting of oxime groups, alkoxy groups, amino groups, vinyloxy groups, amide groups, imide groups, and lactam groups, (II) blend the resulting product of (I) with (A) 100 parts by weight of a hydroxyl endblocked polydiorganosiloxane having a viscosity at 25° C. in the range 0.00005 to 0.5 m 2 /s inclusive and in which the organic radicals are monovalent radicals selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals.
Claim 28
Independent Claim
192 words
A method of making a room temperature curable organopolysiloxane composition comprising (I) mixing (B) an amount of aminoxy organosilicon compound sufficient to provide at least one mol aminoxy group per one mol hydroxyl group in (A), the aminoxy organosilicon compound having a general formula ##STR28## in which each R, R', and R 2 is a monovalent radical selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals, n has a value of from 1 to 50 inclusive, and p has a value of from 1 to 5 inclusive, (C) from 0.5 to 20 parts by weight of a hydrolyzable organosilicon compound containing at least three silicon-bonded hydrolyzable groups per molecule, said hydrolyzable groups being selected from the group consisting of oxime groups, alkoxy groups, amino groups, vinyloxy groups, amide groups, imide groups, and lactam groups, (II) blend the resulting product of (I) with (A) 100 parts by weight of a hydroxyl endblocked polydiorganosiloxane having a viscosity at 25° C. in the range 0.00005 to 0.5 m 2 /s inclusive and in which the organic radicals are monovalent radicals selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-06-06 | 1986-12-06 | 1987-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-06-06 | 1990-12-06 | 1991-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-06-06 | 1994-12-06 | 1995-06-07 | $7700.00 | Window Closed / Lapsed |