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EP0342518A2
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Method and Intermediates for Preparation of bis(Aminoalkyl)Polydiorganosiloxanes
Assignee: General Electric Co
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Filing: 1989-05-11
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Granted: —
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Expires: 2009-05-11
Abstract
Abstract Silicon-nitrogen compounds are prepared by the reaction of an olefinic amine such as allylamine with a polydiorganosiloxane such as 1,1,3,3-tetramethyldisiloxane, in the presence of a platinum-containing hydrosilation catalyst, preferably a specifically defined platinum complex of 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane. Depending on the reaction conditions, the product may be any of several compounds including bis(aminoalkyl)polydiorganosiloxanes and alkenylaminodisiloxanes which are spontaneously converted to cyclic disiloxazanes. The cyclic disiloxazanes may in turn be converted by hydrolysis to bis(aminoalkyl)octaorganotetrasiloxanes.
Inventors
- 👤 Jimmy Lynn Webb
- 👤 Hans Victor Ritschard
- 👤 James Michael Lambert
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 03:33
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C08G77/382; C08G77/388; C08G77/48; C08G77/54
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
105 words
A method for preparing a silicon-nitrogen compound which comprises effecting reaction between the components of a mixture comprising (A) at least one olefinic amine of the formula wherein each R¹ is independently hydrogen, C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl, and (B) at least one polydiorganosiloxane of the formula wherein R² is C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl and x has an average value from 1 to about 300, in the presence of a catalytic amount of (C) a platinum-containing hydrosilation catalyst; said mixture containing titratable acid, if any, in an amount up to 0.5 equivalent per gram-atom of platinum.
Claim 2
Independent Claim
105 words
A method for preparing a silicon-nitrogen compound which comprises effecting reaction between the components of a mixture comprising (A) at least one olefinic amine of the formula wherein each R¹ is independently hydrogen, C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl, and (B) at least one polydiorganosiloxane of the formula wherein R² is C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl and x has an average value from 1 to about 300, in the presence of a catalytic amount of (C) a platinum-containing hydrosilation catalyst; said mixture containing titratable acid, if any, in an amount up to 0.5 equivalent per gram-atom of platinum.
Claim 3
Dependent Claim
31 words
A method according to claim 1 wherein reagent C is a platinum complex of 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane containing halogen, if any, in an amount no greater than 1 gram-atom per gram-atom of platinum.
Claim 4
Dependent Claim
15 words
A method according to claim 2 wherein the reaction is conducted in an inert atmosphere.
Claim 5
Dependent Claim
14 words
A method according to claim 3 wherein reagent A is the only amine present.
Claim 6
Dependent Claim
28 words
A method according to claim 4 wherein the proportion of catalyst is about 5-150 ppm. of platinum by weight based on the total of reagents A and B.
Claim 7
Dependent Claim
20 words
A method according to claim 5 wherein the reaction is conducted at a temperature in the range of about 80-125°C.
Claim 8
Dependent Claim
20 words
A method according to claim 6 wherein x is 1, a diluent is employed and the product is a bis(aminoalkyl)tetraorganodisiloxane.
Claim 9
Dependent Claim
25 words
A method according to claim 7 wherein reagent C contains halogen, if any, in an amount less than about 0.1 gram-atom per gram-atom of platinum.
Claim 10
Dependent Claim
16 words
A method according to claim 8 wherein each R¹ is hydrogen and each R² is methyl.
Claim 11
Dependent Claim
44 words
A method according to claim 9 wherein reagents A and B and a portion of reagent C are added incrementally or continuously to diluent and remaining reagent C, the mole ratio of A to B is about 2.2-2.5:1 and the reaction pressure is atmospheric.
Claim 12
Dependent Claim
13 words
A method according to claim 10 wherein the diluent is toluene or xylene.
Claim 13
Dependent Claim
26 words
A method according to claim 11 wherein the final concentration of combined reagents A and B in the solution is up to about 85% by weight.
Claim 14
Dependent Claim
33 words
A method according to claim 6 wherein x is greater than 1, contact between reagents A, B and C is effected in a system free from diluents and the product is a bis(aminoalkyl)polydiorganosiloxane.
Claim 15
Dependent Claim
25 words
A method according to claim 13 wherein reagent C contains halogen, if any, in an amount less than about 0.1 gram-atom per gram-atom of platinum.
Claim 16
Dependent Claim
16 words
A method according to claim 14 wherein each R¹ is hydrogen and each R² is methyl.
Claim 17
Dependent Claim
23 words
A method according to claim 15 wherein the mole ratio of A to B is about 2.2-2.5:1 and the reaction pressure is atmospheric.
Claim 18
Dependent Claim
49 words
A method according to claim 5 wherein x is 1 and contact between reagents A, B and C is effected in a system free from extraneous diluents and at a temperature initially in the range of about 30-75°C, to afford a product initially comprising an alkenylaminodisilazane of the formula
Claim 19
Dependent Claim
25 words
A method according to claim 17 wherein reagent C contains halogen, if any, in an amount less than about 0.1 gram-atom per gram-atom of platinum.
Claim 20
Dependent Claim
20 words
A method according to claim 18 wherein said product undergoes intramolecular hydrosilation to form a cyclic disiloxazane of the formula
Claim 21
Dependent Claim
16 words
A method according to claim 19 wherein each R¹ is hydrogen and each R² is methyl.
Claim 22
Dependent Claim
19 words
A method according to claim 20 wherein the molar ratio of reagent A to reagent B is about 2-4:1.
Claim 23
Dependent Claim
24 words
A method according to claim 21 wherein the mixture contains titratable acid in an amount less than about 10 milliequivalents per gram-atom of platinum.
Claim 24
Dependent Claim
31 words
A method according to claim 22 wherein the product is subsequently hydrolyzed to a bis(aminoalkyl)octaorganotetrasiloxane by contact with an excess of water at a temperature in the range of about 25-120°C.
Claim 25
Dependent Claim
32 words
An alkenylaminodisiloxane having the formula wherein each R¹ is independently hydrogen, C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl and R² is C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl.
Claim 26
Dependent Claim
32 words
An alkenylaminodisiloxane having the formula wherein each R¹ is independently hydrogen, C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl and R² is C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl.
Claim 27
Dependent Claim
15 words
An alkenylaminodisiloxane according to claim 24 wherein each R¹ is hydrogen and R² is methyl.
Claim 28
Dependent Claim
33 words
A cyclic disiloxazane having the formula wherein each R¹ is independently hydrogen, C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl and R² is C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl.
Claim 29
Dependent Claim
33 words
A cyclic disiloxazane having the formula wherein each R¹ is independently hydrogen, C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl and R² is C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl.
Claim 30
Dependent Claim
16 words
A cyclic disiloxazane according to claim 26 wherein each R¹ is hydrogen and R² is methyl.
Claim 31
Dependent Claim
36 words
An alkoxyaminoalkyltetraorganodisiloxane having the formula wherein each R¹ is independently hydrogen, C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl; R² is C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl; and R³ is C₁₋₄ alkyl.
Claim 32
Dependent Claim
36 words
An alkoxyaminoalkyltetraorganodisiloxane having the formula wherein each R¹ is independently hydrogen, C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl; R² is C₁₋₄ primary or secondary alkyl, phenyl or substituted phenyl; and R³ is C₁₋₄ alkyl.
Claim 33
Dependent Claim
19 words
A disiloxane according to claim 28 wherein each R¹ is hydrogen, each R² is methyl and R³ is methyl.
References Cited (Backward Citations)
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