US4228096A
Expired / Lapsed
US
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Method of preparing quaternary ammonium salts from various morpholinones
Assignee: Dow Chemical Co
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Filing: 1979-04-16
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Granted: 1980-10-14
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Expires: 1999-04-16
Abstract
Abstract Quaternary ammonium salts of the formula ##STR1## where R, R', R" and R'" are typically individually alkyl or inertly-substituted alkyl radicals and Y.sup.⊖ is a neutralizing anion, are facilely prepared by amidating the carbonyl carbon and subsequently quaternizing the ring nitrogen of an N-alkyl morpholinone. These quaternary ammonium salts demonstrate biological, antistatic and surfactant activity.
Inventors
- 👤 John W. Bozzelli
- 👤 Nancy J. Morris
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:46
CPC Classifications
C; C07; C07C; C07C237/00
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
113 words
A method for preparing a compound of the formula ##STR17## where R, R' and R"' are individually hydrogen, an aliphatic, alicyclic, aryl or an inertly-substituted aliphatic, alicyclic or aryl radical; R" is a C 1 -C 5 alkyl radical; and Y.sup.⊖ is a neutralizing anion, the method comprising: (a) contacting at a temperature of about 50° C. to about 250° C. a morpholinone of the formula ##STR18## with an amidating agent of the formula ##STR19## and (b) contacting at a temperature of about 25° C. to about 150° C. the reaction product of (a) with a quaternizing agent of the formula R"'Y where R, R', R", R"' and Y are as previously defined.
Claim 2
Independent Claim
113 words
A method for preparing a compound of the formula ##STR17## where R, R' and R"' are individually hydrogen, an aliphatic, alicyclic, aryl or an inertly-substituted aliphatic, alicyclic or aryl radical; R" is a C 1 -C 5 alkyl radical; and Y.sup.⊖ is a neutralizing anion, the method comprising: (a) contacting at a temperature of about 50° C. to about 250° C. a morpholinone of the formula ##STR18## with an amidating agent of the formula ##STR19## and (b) contacting at a temperature of about 25° C. to about 150° C. the reaction product of (a) with a quaternizing agent of the formula R"'Y where R, R', R", R"' and Y are as previously defined.
Claim 3
Independent Claim
113 words
A method for preparing a compound of the formula ##STR20## where R, R' and R"' are individually hydrogen, an aliphatic, alicyclic, aryl or an inertly-substituted aliphatic, alicyclic or aryl radical; R" is a C 1 -C 5 alkyl radical; and Y.sup.⊖ is a neutralizing anion, the method comprising: (a) contacting at a temperature of about 25° C. to about 150° C. a morpholinone of the formula ##STR21## with a quaternizing agent of the formula R"'Y; and (b) contacting at a temperature of about 50° C. to about 250° C. the reaction product of (a) with an amidating agent of the formula ##STR22## where R, R', R", R"' and Y are as previously defined.
Claim 4
Independent Claim
113 words
A method for preparing a compound of the formula ##STR20## where R, R' and R"' are individually hydrogen, an aliphatic, alicyclic, aryl or an inertly-substituted aliphatic, alicyclic or aryl radical; R" is a C 1 -C 5 alkyl radical; and Y.sup.⊖ is a neutralizing anion, the method comprising: (a) contacting at a temperature of about 25° C. to about 150° C. a morpholinone of the formula ##STR21## with a quaternizing agent of the formula R"'Y; and (b) contacting at a temperature of about 50° C. to about 250° C. the reaction product of (a) with an amidating agent of the formula ##STR22## where R, R', R", R"' and Y are as previously defined.
Claim 5
Dependent Claim
26 words
The method of claim 1 or 2 where the aliphatic and alicyclic radicals of R, R' and R''' are of 1 to about 30 carbon atoms.
Claim 6
Dependent Claim
18 words
The method of claim 1 or 2 where the aryl radical of R, R' and R''' is phenyl.
Claim 7
Dependent Claim
25 words
The method of claim 1 or 2 where R and R' are individually hydrogen or an alkyl radical of 8 to about 20 carbon atoms.
Claim 8
Dependent Claim
25 words
The method of claim 5 where R''' is an aliphatic, alicyclic or an inertly-substituted aliphatic or alicyclic radical of 8 to about 20 carbon atoms.
Claim 9
Dependent Claim
12 words
The method of claim 6 where Y is methylsulfate, bisulfate or halogen.
Claim 10
Dependent Claim
19 words
The method of claim 1 or 2 where the amidating agent is undecyl-, octyl-, nonyl-, tridecyl-, octadecyl- or oleylamine.
Claim 11
Dependent Claim
16 words
The method of claim 8 where the quaternizing agent is dimethyl sulfate, 3-bromo-1,1-dichloropropene, 1,3-dichloropropene or α-bromo-4-nitrotoluene.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-14 | 1984-04-14 | 1984-10-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-14 | 1988-04-14 | 1988-10-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-14 | 1992-04-14 | 1992-10-14 | $7700.00 | Window Closed / Lapsed |