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US4429096A
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Quaternary amine carbamate or urea compounds based on isopropenyl-α,α-dimethylbenzyl isocyanate
Assignee: Wyeth Holdings LLC
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Filing: 1983-06-01
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Granted: 1984-01-31
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Expires: 2003-06-01
Abstract
Abstract A meta- or para-compound of the formula: ##STR1## wherein: X⊖ is an anion selected from the group consisting of R 4 OSO 3 ⊖, Cl⊖, Br⊖ and I⊖; A is -O- or ##STR2## wherein: n is 2 or 3; R 1 , R 2 and R 3 which may be the same or different, are lower alkyl; and R 4 is lower alkyl or allyl. Also disclosed is a method of making the compound by reacting meta- or para-isopropenyl-α,α-dimethylbenzyl isocyanate with either an amino alcohol or a dialkylaminoethyleneamine, and quaternzing the reaction product with an alkylating agent. The compound may be polymerized with a co-monomer such as acrylamide to yield water-soluble cationic polymers for use in water clarification, flocculation, and hair spray applications.
Inventors
- 👤 Frederic C. Schaefer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 16:03
CPC Classifications
C; C07; C07C; C07C275/00; C07C275/28; C07C275/40; D; D21; D21H; D21H17/00; D21H17/20; D21H17/33; D21H17/34; D21H17/41; D21H17/44; D21H17/45; D21H17/455; A; A61; A61K; A61K8/00; A61K8/18; A61K8/72; A61K8/84; A61K8/87; A61Q; A61Q5/00; A61Q5/06; C02; C02F; C02F1/00; C02F1/52; C02F1/54; C07C273/00; C07C273/18; C07C273/1809; C07C273/1818; C07C273/1854; C07C275/04; C07C275/20; C07C275/24; C08; C08F; C08F12/00; C08F12/02; C08F12/04; C08F12/14; C08F12/26; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/728
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
67 words
A meta- or para-compound of the formula; ##STR16## wherein: X - is an anion selected from the group consisting of R 4 OSO 3 .sup.⊖, Cl.sup.⊖, Br.sup.⊖ and I.sup.⊖ ; A is --O-- or ##STR17## wherein: n is 2 or 3; R 1 , R 2 and R 3 which may be the same or different, are lower alkyl; and R 4 is lower alkyl or allyl.
Claim 2
Dependent Claim
67 words
A meta- or para-compound of the formula; ##STR16## wherein: X - is an anion selected from the group consisting of R 4 OSO 3 .sup.⊖, Cl.sup.⊖, Br.sup.⊖ and I.sup.⊖ ; A is --O-- or ##STR17## wherein: n is 2 or 3; R 1 , R 2 and R 3 which may be the same or different, are lower alkyl; and R 4 is lower alkyl or allyl.
Claim 3
Dependent Claim
20 words
A compound according to claim 1 wherein R 1 , R 2 , R 3 and R 4 are methyl.
Claim 4
Dependent Claim
14 words
A compound according to claim 2 wherein n is 2 and A is --O--.
Claim 5
Independent Claim
128 words
A method of making a compound of the formula ##STR18## wherein: X - is an anion selected from the group consisting of R 4 OSO 3 .sup.⊖, Cl.sup.⊖, Br.sup.⊖ and I.sup.⊖ ; wherein: n is 2 or 3; R 1 , R 2 , R 3 , which may be the same or different, are lower alkyl; and R 4 is lower alkyl or allyl, comprising: (a) reacting ameta- or para-monoene-monoisocyanate of the formula: ##STR19## with an amino alcohol selected from the group consisting of dimethylaminoethano, diethylaminoethanol, dimethylaminopropanol, diethylaminopropanol, and 2-dimethylamino-isobutanol to yield a tertiary amino-carbamate of the formula: ##STR20## (b) quaternizing said tertiary amino-carbamate, with an alkylating agent selected from the group consisting of dimethylsulfate, methyl chloride, allyl chloride, ethylene oxide and epichlorohydrin, to yield said compound.
Claim 6
Independent Claim
128 words
A method of making a compound of the formula ##STR18## wherein: X - is an anion selected from the group consisting of R 4 OSO 3 .sup.⊖, Cl.sup.⊖, Br.sup.⊖ and I.sup.⊖ ; wherein: n is 2 or 3; R 1 , R 2 , R 3 , which may be the same or different, are lower alkyl; and R 4 is lower alkyl or allyl, comprising: (a) reacting ameta- or para-monoene-monoisocyanate of the formula: ##STR19## with an amino alcohol selected from the group consisting of dimethylaminoethano, diethylaminoethanol, dimethylaminopropanol, diethylaminopropanol, and 2-dimethylamino-isobutanol to yield a tertiary amino-carbamate of the formula: ##STR20## (b) quaternizing said tertiary amino-carbamate, with an alkylating agent selected from the group consisting of dimethylsulfate, methyl chloride, allyl chloride, ethylene oxide and epichlorohydrin, to yield said compound.
Claim 7
Dependent Claim
23 words
A method according to claim 4 wherein n is 2,and R 1 , R 2 , R 3 and R 4 are methyl.
Claim 8
Independent Claim
118 words
A method of making a meta- or para-compound of the formula: ##STR21## wherein: X - is an anion selected from the group consisting of R 4 OSO 3 .sup.⊖, Cl.sup.⊖, Br.sup.⊖, and I.sup.⊖ wherein: R 1 , R 2 and R 3 , which may be the same or different, are lower alkyl; and R 4 is lower alkyl or allyl, comprising: (a) reacting a meta- or para-monoene-monoisocyanate of the formula ##STR22## with a dialkylaminoalkyleneamine of the formula ##STR23## to yield a tertiary amino-urea of the formula: ##STR24## and (b) quaternizing said tertiary amino-urea, with an alkylating agent selected from the group consisting of dimethyl sulfate, methyl chloride, allyl chloride, ethylene oxide and epichlorohydrin, to yield said compound.
Claim 9
Independent Claim
118 words
A method of making a meta- or para-compound of the formula: ##STR21## wherein: X - is an anion selected from the group consisting of R 4 OSO 3 .sup.⊖, Cl.sup.⊖, Br.sup.⊖, and I.sup.⊖ wherein: R 1 , R 2 and R 3 , which may be the same or different, are lower alkyl; and R 4 is lower alkyl or allyl, comprising: (a) reacting a meta- or para-monoene-monoisocyanate of the formula ##STR22## with a dialkylaminoalkyleneamine of the formula ##STR23## to yield a tertiary amino-urea of the formula: ##STR24## and (b) quaternizing said tertiary amino-urea, with an alkylating agent selected from the group consisting of dimethyl sulfate, methyl chloride, allyl chloride, ethylene oxide and epichlorohydrin, to yield said compound.
Claim 10
Dependent Claim
27 words
A method of making a compound according to claim 1 comprising reacting the corresponding quaternary amino-alcohol or amine with a meta- or para-monoene-monoisocyanate of the formula ##STR25##
Claim 11
Dependent Claim
10 words
A copolymer of the compound of claim 1 and acrylamide.
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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) | 1987-01-30 | 1987-08-01 | 1988-01-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-01-30 | 1991-08-01 | 1992-01-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-01-30 | 1995-08-01 | 1996-01-31 | $7700.00 | Window Closed / Lapsed |