Patent US4093663A successfully refreshed from Google Patents.
US4093663A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel onium surfactants
Assignee: Dow Chemical Co
•
Filing: 1973-11-15
•
Granted: 1978-06-06
•
Expires: 1993-11-15
Abstract
Abstract Novel onium surfactants are described which correspond to the formula X[(CH 2 CH 2 O) m CH 2 --R--CHR'--Q.sup.⊕ A.sup.⊖ ] n , wherein X is an n-valent hydrophobic radical derived by the removal of n-atoms of active hydrogen from an organic compound; m is one or more; R is a divalent aromatic radical of from 6 to about 14 carbon atoms, the chain-length of which may be interrupted by oxygen or sulfur atoms; R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; Q + is a quaternized atom of nitrogen or phosphorus or a tertiary atom of sulfur; A - is a compatible anion; and n is from 1 to 5. The following compound is an example C 9 H 19 --C 6 H 4 --O--CH 2 CH 2 O-- 15 CH 2 --C 6 H 4 --CH 2 --S.sup.⊕ --(CH 3 ) 2 Cl.sup.⊖ . The novel surfactants are prepared in two steps. In step 1, various nonionic surfactants are reacted with certain chloromethylated aromatics in the presence of a strong base to give novel intermediates which are subsequently reacted in step 2 with tertiary amines, pyridines, tertiary phosphines, sulfides, thiourea etc. to give the onium surfactants.
Inventors
- 👤 Robert F. Harris
- 👤 Earl H. Wagener
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 18:54
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/329; C08G65/337; C07; C07C; C07C323/00; C07C335/00; C07C335/30; C07C335/32; C07C381/00; C07C381/12; C07C43/00; C07C43/02; C07C43/20; C07C43/225; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/20; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5456; Y; Y10; Y10S; Y10S516/00; Y10S516/01; Y10S516/07
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
169 words
An onium surfactant corresponding to the formula X[(CH 2 CH 2 O-- m CH 2 --R--CHR'--Q + A - n wherein X is a hydrophobic n-valent radical derived by the removal of n-atoms of active hydrogen from an organic compound and corresponding to the hydrophobic portion of a nonionic surfactant having a hydrophilic-lipophilic-balance of from 1 to about 30 and having the structural formula X[(CH 2 CH 2 O-- m H] n ; m is an integer of at least 1 and is the same in each of the above formulas; R is a divalent aromatic hydrocarbon radical of from 6 to about 14 carbon atoms, the chain length of which can be interrupted by oxygen or sulfur atoms; R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; Q + is a tertiary atom of sulfur; A - is a compatible anion; and n is an integer of from 1 l to 5 and is the same in each of the above formulas.
Claim 2
Dependent Claim
169 words
An onium surfactant corresponding to the formula X[(CH 2 CH 2 O-- m CH 2 --R--CHR'--Q + A - n wherein X is a hydrophobic n-valent radical derived by the removal of n-atoms of active hydrogen from an organic compound and corresponding to the hydrophobic portion of a nonionic surfactant having a hydrophilic-lipophilic-balance of from 1 to about 30 and having the structural formula X[(CH 2 CH 2 O-- m H] n ; m is an integer of at least 1 and is the same in each of the above formulas; R is a divalent aromatic hydrocarbon radical of from 6 to about 14 carbon atoms, the chain length of which can be interrupted by oxygen or sulfur atoms; R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; Q + is a tertiary atom of sulfur; A - is a compatible anion; and n is an integer of from 1 l to 5 and is the same in each of the above formulas.
Claim 3
Dependent Claim
16 words
The surfactant defined by claim 1 wherein n is an integer of from 1 to 3.
Claim 4
Dependent Claim
10 words
The surfactant defined by claim 2 wherein n is 1.
Claim 5
Dependent Claim
22 words
The surfactant defined by claim 1 wherein R is m- or p-phenylene or a divalent radical of diphenyl oxide or diphenyl sulfide.
Claim 6
Dependent Claim
12 words
The surfactant defined by claim 1 wherein R is m- or p-phenylene.
Claim 7
Dependent Claim
17 words
The surfactant defined by claim 1 wherein m is an integer of from 1 to about 200.
Claim 8
Dependent Claim
17 words
The surfactant defined by claim 6 wherein m is an integer of from 4 to about 50.
Claim 9
Dependent Claim
184 words
An onium surfactant corresponding to the formula X[(CH 2 CH 2 O-- m CH 2 --R--CHR'--Q + A - ] n , wherein X is a hydrophobic n-valent radical derived by removal of active hydrogen from an aliphatic alcohol, a phenol, an organic carboxylic acid or carboxamide, or a polymer of propylene oxide and/or butylene oxide and corresponding to the hydrophobic portion of a nonionic surfactant having a hydrophilic-lipophilic-balance of from 1 to about 30 and having the structural formula X[(CH 2 CH 2 O-- m H] n ; m is an integer of at least 1 and is the same in each of the above formulas; R is a divalent aromatic hydrocarbon radical of from 6 to about 14 carbon atoms, the chain length of which can be interrupted by oxygen or sulfur atoms; R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; Q + is a tertiary atom of sulfur; A - is a compatible anion; and n is an integer of from 1 to 5 and is the same in each of the above formulas.
Claim 10
Dependent Claim
184 words
An onium surfactant corresponding to the formula X[(CH 2 CH 2 O-- m CH 2 --R--CHR'--Q + A - ] n , wherein X is a hydrophobic n-valent radical derived by removal of active hydrogen from an aliphatic alcohol, a phenol, an organic carboxylic acid or carboxamide, or a polymer of propylene oxide and/or butylene oxide and corresponding to the hydrophobic portion of a nonionic surfactant having a hydrophilic-lipophilic-balance of from 1 to about 30 and having the structural formula X[(CH 2 CH 2 O-- m H] n ; m is an integer of at least 1 and is the same in each of the above formulas; R is a divalent aromatic hydrocarbon radical of from 6 to about 14 carbon atoms, the chain length of which can be interrupted by oxygen or sulfur atoms; R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; Q + is a tertiary atom of sulfur; A - is a compatible anion; and n is an integer of from 1 to 5 and is the same in each of the above formulas.
Claim 11
Dependent Claim
47 words
The surfactant defined by claim 8 wherein said radical is derived by the removal of active hydrogen from an alkanol, an alkenol, an alkylphenol, an alkanoic acid or amide of from about 10 to about 24 carbon atoms or a polymer of propylene oxide and/or butylene oxide.
Claim 12
Dependent Claim
20 words
The surfactant defined by claim 9 wherein said radical is derived by the removal of active hydrogen from an alkylphenol.
Claim 13
Dependent Claim
11 words
The surfactant defined by claim 10 wherein said alkylphenol is nonylphenol.
Claim 14
Dependent Claim
51 words
The surfactant defined by claim 11 wherein m is an integer of from 1 to about 200; R is a m- or p-phenylene; Q + is a sulfonium, thiophenium, tetrahydrothiophenium or an isothiouronium radical; A - is halide, nitrate, sulfate, bisulfate, methylsulfate, lower alkanoate, benzoate, or tosylate; and n is 1.
Claim 15
Dependent Claim
54 words
The surfactant defined by claim 12 wherein Q + is --S + R 5 R 6 wherein R 5 and R 6 are alkyl and the total aggregate carbon content of R 5 and R 6 is up to about 24 carbon atoms or Q + is tetrahydrothiophenium, isothiouronium or N,N,N',N'-tetramethyl or tetraethyl isothiouronium.
Claim 16
Dependent Claim
151 words
A compound corresponding to the formula X[(CH 2 CH 2 O-- m CH 2 --R--CHR'Cl] n wherein X is a hydrophobic n-valent radical derived by the removal of n-atoms of active hydrogen from an organic compound and corresponds to the hydrophobic portion of a nonionic surfactant having a hydrophilic-lipophilic-balance of from 1 to about 30 and having the structural formula X[(CH 2 CH 2 O-- m H] n ; m is an integer of at least 1 and is the same in each of the above formulas; R is a divalent aromatic hydrocarbon radical of from 6 to about 14 carbon atoms, the chain length of which can be interrupted by oxygen or sulfur atoms; and R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; and n is an integer of from 1 to 5 and is the same in each of the above formulas.
Claim 17
Dependent Claim
151 words
A compound corresponding to the formula X[(CH 2 CH 2 O-- m CH 2 --R--CHR'Cl] n wherein X is a hydrophobic n-valent radical derived by the removal of n-atoms of active hydrogen from an organic compound and corresponds to the hydrophobic portion of a nonionic surfactant having a hydrophilic-lipophilic-balance of from 1 to about 30 and having the structural formula X[(CH 2 CH 2 O-- m H] n ; m is an integer of at least 1 and is the same in each of the above formulas; R is a divalent aromatic hydrocarbon radical of from 6 to about 14 carbon atoms, the chain length of which can be interrupted by oxygen or sulfur atoms; and R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; and n is an integer of from 1 to 5 and is the same in each of the above formulas.
Claim 18
Dependent Claim
19 words
A compound which corresponds to the structural formula ##STR16## where m is an integer of from 4 to 80.
Claim 19
Dependent Claim
19 words
A compound which corresponds to the structural formula ##STR16## where m is an integer of from 4 to 80.
References Cited (Backward Citations)
CA890943A
Cited
US2309691A
Cited
US2395336A
Cited
US2832795A
Cited
US3234230A
Cited
US3409660A
Cited
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 |