US4093642A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Surface active silicones
Assignee: OSI Specialties Inc
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Filing: 1976-12-20
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Granted: 1978-06-06
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Expires: 1996-12-20
Abstract
Abstract This invention relates to ion-pair-containing siloxane compounds that are extremely effective as surface tension depressants. The compounds of the present invention contain both anionic and cationic substituents and can be formed by metathesis reactions between metallic salts of anionic silicone or organic surface-active compounds and halide salts of quaternary ammonium silicone or organic surface-active compounds. The compounds of the invention are relatively pH insensitive when compared to siloxanes bearing anionic and cationic substituents that are formed by proton transfer. Thus, the organosilicon compounds of the invention will remain stable despite changes in pH of the mixture in which they are present.
Inventors
- 👤 Curtis L. Schilling
- 👤 Bela Prokai
- 👤 Bernard Kanner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 02:07
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/045; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0834; C07F7/0838; C08G77/38; C08G77/382
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
292 words
A composition of matter selected from the group consisting of: A. siloxane compounds having the structural formula: ##STR9## where (1) R is a monovalent hydrocarbon group having from 1 to 18 carbon atoms, (2) R' is a divalent organic group whose valences are provided by carbon atoms and having from 1 to 18 carbon atoms, (3) XX - is a divalent anionic group covalently bonded to R' and ionically bonded to Y + , (4) y + is a monovalent cation that has at least 8 carbon atoms and that is derived from a cationic surfactant having a halogen counterion by removal of the halogen and that is free of ionically-bonded hydrogen, (5) m is an integer having a value from 1 to 100, (6) n is an integer having a value from 0 to 200, (7) the ratio of m to (n+2) being from 0.1 to 20, and B. siloxane compounds having the structural formula: ##STR10## where (1) R is a monovalent hydrocarbon group having from 1 to 18 carbon atoms, (2) R' is a divalent organic group whose valences are provided by carbon atoms and having from 1 to 18 carbon atoms, (3) YY + is a divalent cationic group that is free of ionically-bonded hydrogen and that is covalently bonded to R' and ionically bonded to X - , (4) x - is a monovalent anion that has at least 8 carbon atoms and that is derived from an anionic surfactant having a monovalent metal counterion by removal of the metal, (5) m is an integer having an average value from 1 to 100, (6) n is an integer having a value from 0 to 200, and (7) the ratio of m to (n+2) being from 0.1 to 20.
Claim 2
Dependent Claim
292 words
A composition of matter selected from the group consisting of: A. siloxane compounds having the structural formula: ##STR9## where (1) R is a monovalent hydrocarbon group having from 1 to 18 carbon atoms, (2) R' is a divalent organic group whose valences are provided by carbon atoms and having from 1 to 18 carbon atoms, (3) XX - is a divalent anionic group covalently bonded to R' and ionically bonded to Y + , (4) y + is a monovalent cation that has at least 8 carbon atoms and that is derived from a cationic surfactant having a halogen counterion by removal of the halogen and that is free of ionically-bonded hydrogen, (5) m is an integer having a value from 1 to 100, (6) n is an integer having a value from 0 to 200, (7) the ratio of m to (n+2) being from 0.1 to 20, and B. siloxane compounds having the structural formula: ##STR10## where (1) R is a monovalent hydrocarbon group having from 1 to 18 carbon atoms, (2) R' is a divalent organic group whose valences are provided by carbon atoms and having from 1 to 18 carbon atoms, (3) YY + is a divalent cationic group that is free of ionically-bonded hydrogen and that is covalently bonded to R' and ionically bonded to X - , (4) x - is a monovalent anion that has at least 8 carbon atoms and that is derived from an anionic surfactant having a monovalent metal counterion by removal of the metal, (5) m is an integer having an average value from 1 to 100, (6) n is an integer having a value from 0 to 200, and (7) the ratio of m to (n+2) being from 0.1 to 20.
Claim 3
Dependent Claim
12 words
A composition of matter as defined in Part A of claim 1.
Claim 4
Dependent Claim
12 words
A composition of matter as defined in Part B of claim 1.
Claim 5
Dependent Claim
44 words
A composition of matter as claimed in Part A of claim 1 wherein R is methyl, R' has the formula --(CH 2 ) 3 OCH 2 CHOHCH 2 --, m has a value from 1 to 50 and n has a value of 0.
Claim 6
Dependent Claim
44 words
A composition of matter as claimed in Part B of claim 1 wherein R is methyl, R' has the formula --(CH 2 ) 3 OCH 2 CHOHCH 2 --, m has a value from 1 to 50 and n has a value of 0.
Claim 7
Dependent Claim
35 words
A composition of matter as defined in claim 2 having the structural formula: (Me 3 SiO) 2 MeSi(CH 2 ) 3 OCH 2 CHOHCH 2 SO 3 - Me 3 + NC 12 H 25
Claim 8
Dependent Claim
44 words
A composition of matter as defined in claim 2 having the structural formula: (Me 3 SiO) 2 MeSi(CH 2 ) 3 OCH 2 CHOHCH 2 SO 3 - Me 3 + NCH 2 CHOHCH 2 O-- (CH 2 ) 3 MeSi(Me 3 SiO) 2
Claim 9
Dependent Claim
51 words
A composition of matter as defined in claim 3 having the structural formula: (Me 3 SiO) 2 MeSi (CH 2 ) 3 OCH 2 CHOHCH.sub. 2 + NMe 3 - O 3 SCH 2 CH 2 N-- (CH 3 )CH 2 CHOHCH 2 O(CH 2 ) 3 SiMe(OSiMe 3 ) 2
Claim 10
Dependent Claim
35 words
A composition of matter as defined in claim 3 having the structural formula: (Me 3 SiO) 2 MeSi(CH 2 ) 3 OCH 2 CHOHCH 2 + NMe 3 - O 4 SC 10 H 21
Claim 11
Dependent Claim
14 words
A composition of matter as defined in claim 3 having the structural formula: ##STR11##
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) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |