US4587320A
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US
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Method for making carboxyfunctional silicone glycols
Assignee: Dow Silicones Corp
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Filing: 1984-12-21
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Granted: 1986-05-06
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Expires: 2004-12-21
Abstract
Abstract Carboxyfunctional silicone glycols are made by equilibration at elevated temperatures of silicone glycols in which the glycol radical or radicals are bonded to silicon with an Si--C linkage and carboxyfunctional siloxanes in which the carboxy radical or radicals are bonded to silicon with an Si--C linkage in the presence of an acid catalyst which is capable of breaking Si--O linkages but not Si--C linkages. The carboxyfunctional silicone glycols so produced are of the type which are useful as profoamers, surfactants, spreading agents for active chemicals, such as pesticides, hydrophilizing treatments for fabrics and hair, as emollients in cosmetic formulations and as chelates.
Inventors
- 👤 Terence J. Swihart
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 14:37
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/72; A61K8/84; A61K8/89; A61K8/891; A61K8/894; A61K8/896; A61K8/899; A61Q; A61Q19/00; C; C08; C08G; C08G77/00; C08G77/04; C08G77/06; C08G77/10; C08G77/14; C08G77/42; C08G77/46
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
150 words
A method for making a carboxyfunctional silicone glycol which method comprises the steps of: (1) mixing together (a) a silicone glycol or a mixture of silicone glycols in which at least one of the glycol radicals is bonded to silicon with an Si--C linkage; (b) a carboxyfunctional siloxane, or a mixture of carboxyfunctional siloxanes in which at least one of the carboxy radicals is bonded to silicon with an Si--C linkage wherein at least one of (a) and (b) also includes non-glycol-containing and non-carboxyfunctional-containing diorganosiloxane units; and (c) a catalytic amount of an acid catalyst capable of breaking Si--O linkages in (a) and (b) but incapable of breaking Si--C linkaqes therein; (2) heating the mixture to an elevated temperature; and (3) maintaining the mixture at said elevated temperature for at least about 4 hours, whereby equilibration of (a) and (b) occurs to produce an equilibration product containing carboxyfunctional silicone glycol.
Claim 2
Independent Claim
150 words
A method for making a carboxyfunctional silicone glycol which method comprises the steps of: (1) mixing together (a) a silicone glycol or a mixture of silicone glycols in which at least one of the glycol radicals is bonded to silicon with an Si--C linkage; (b) a carboxyfunctional siloxane, or a mixture of carboxyfunctional siloxanes in which at least one of the carboxy radicals is bonded to silicon with an Si--C linkage wherein at least one of (a) and (b) also includes non-glycol-containing and non-carboxyfunctional-containing diorganosiloxane units; and (c) a catalytic amount of an acid catalyst capable of breaking Si--O linkages in (a) and (b) but incapable of breaking Si--C linkaqes therein; (2) heating the mixture to an elevated temperature; and (3) maintaining the mixture at said elevated temperature for at least about 4 hours, whereby equilibration of (a) and (b) occurs to produce an equilibration product containing carboxyfunctional silicone glycol.
Claim 3
Dependent Claim
14 words
The method of claim 1 wherein the mixing and heating steps are performed simultaneously.
Claim 4
Dependent Claim
32 words
The method of claim 1 wherein (c) is trifluoromethane sulfonic acid and wherein, in step (2), the mixture is heated to a temperature of from about 40° C. to about 65° C.
Claim 5
Dependent Claim
21 words
The method of claim 3 where (c) is present in the mixture in an amount of about 200 parts per million.
Claim 6
Dependent Claim
20 words
The method of claim 1 which includes the additional subsequent step of neutralizing acid catalyst (c) with a suitable base.
Claim 7
Dependent Claim
28 words
The method of claim 5 which includes the further subsequent step of filtering the treated equilibration product to remove salts produced by the neutralization of the acid catalyst.
Claim 8
Dependent Claim
20 words
The method of claim 3 which includes the additional subsequent step of neutralizing the trifluoromethane sulfonic acid with dimethyl formamid.
Claim 9
Dependent Claim
29 words
The method of claim 7 which includes the further subsequent step of filtering the equilibration product to remove salts produced by the neutralization of the trifluoromethane sulfonic acid catalyst.
Claim 10
Dependent Claim
33 words
The method of claim 1 including the additional subsequent step of reacting the carboxyfunctional silicone glycol in the equilibration product with a metal hydroxide to form the carboxylic acid salt of said glycol.
Claim 11
Dependent Claim
13 words
The method of claim 9 wherein the metal hydroxide is NaOH or KOH.
Claim 12
Dependent Claim
44 words
The method of claim 1 wherein (a) and (b) are present in amounts which will result in an equilibration product comprising from about 0.5 to about 20 mole percent carboxyfunctional siloxane units, and from about 0.5 to about 20 mole percent silicone glycol units.
Claim 13
Dependent Claim
216 words
The method of claim 1 wherein (a) is R 3 O(R 2 O) c (R'O) b (CH 2 ) a SiR 2 (OSiR 2 ) y (CH 2 ) a (OR') b (OR 2 ) c OR 3 wherein "y" is a positive integer, "R" is a substituted or unsubstituted hydrocarbon radical "R'" is --CH 2 CH 2 --, "R 2 " is "R'" or ##STR14## "R 3 " is hydrogen or a substituted or unsubstituted hydrocarbon radical, "a" is a positive integer and "b" plus "c" either of which may be 0, are from about 1 to about 50, inclusive; or mixtures thereof, or ##STR15## wherein "w" and "z" are positive integers, and "R", "R'", "R 2 ", "R 3 ", "a", "b", and "c" are as described above, and (b) is ##STR16## wherein each "R" is as described above, "A" is hydrogen or any monovalent substituted or unsubstituted hydrocarbon radical, "R 4 " is any divalent hydrocarbon radical or hetero-atom-containing hydrocarbon radical which provides Si--C linkage, "e" is 1 or 0, "f" is 3 to 6, inclusive, when "e" is 0, and "f" is a positive integer when "e" is 1; or ##STR17## wherein "R", "R 4 " and "A" are as defined above and "j" and "h" are positive integers; or mixtures thereof.
Claim 14
Dependent Claim
77 words
The method of claim 12 wherein the carboxyfunctional silicone glycol in the equilibration product has the general formula: ##STR18## wherein "R", "R'", "R 2 ", "R 3 ", "R 4 ", "a", "b", "c" and "A" are as set out in claim 12 and the average molar ratio of "d" and "g" are selected such that the mole percent silicone glycol units and the mole percent carboxyfunctional siloxane units each varies from about 0.5 to about 20.
Claim 15
Dependent Claim
78 words
The method of claim 12 wherein the carboxyfunctional silicone glycol in the equilibration product has the general formula: ##STR19## wherein "R", "R'", "R 2 ", "R 3 ", "R 4 ", "A", "a", "b", and "c" are as set out in claim 12 and wherein the average molar ratios of "i", "k" and "l" are selected such that the mole percent silicone glycol units and the mole percent carboxyfunctional siloxane units each varies from about 0.5 to 20.
Claim 16
Dependent Claim
52 words
The method of claim 13 wherein "A" is hydrogen and wherein the method includes the additional subsequent step of reacting the carboxyfunctional silicone glycol in the equilibration product with sodium hydroxide or potassium hydroxide whereby "A" is replaced by potassium or sodium to form the metal salt of the carboxyfunctional silicone glycol.
Claim 17
Dependent Claim
52 words
The method of claim 14 wherein "A" is hydrogen and wherein the method includes the additional subsequent step of reacting the carboxyfunctional silicone glycol in the reaction product with sodium hydroxide or potassium hydroxide whereby "A" is replaced by potassium or sodium to form the metal salt of the carboxyfunctional silicone glycol.
Claim 18
Dependent Claim
16 words
The method of claim 12 wherein R 4 is --CH 2 CH 2 SCH 2 --.
Claim 19
Dependent Claim
16 words
The method of claim 13 wherein R 4 is --CH 2 CH 2 SCH 2 --.
Claim 20
Dependent Claim
16 words
The method of claim 14 wherein R 4 is --CH 2 CH 2 SCH 2 --.
References Cited (Backward Citations)
US3965150A
Cited
US4081410A
Cited
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