US4091113A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Randomly terminated capped polymers
Assignee: MILLMASTER ONYX GROUP LP
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Filing: 1977-04-20
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Granted: 1978-05-23
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Expires: 1997-04-20
Abstract
Abstract Anti-microbial polymeric quaternary ammonium compounds and mixtures thereof, having linear chains which terminate in quaternary ammonium moieties, such compounds being formed by polymerization which is carried out in such a manner that the linear chains thereof are terminated in random fashion, the reaction resulting in the formation of the compounds being a one-step reaction between 1,4-dihalo-2-butene and a mixture of a difunctional tertiary amine and a monofunctional tertiary amine wherein the molar quantity of the difunctional amine is greater than the molar quantity of the monofunctional amine. These products are especially effective hair conditioning agents.
Inventors
- 👤 Harold A. Green
- 👤 John J. Merianos
- 👤 Alfonso N. Petrocci
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 23:03
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/02; C08G73/0206; C08G73/0213; C08G73/0226; A; A01; A01N; A01N31/00; A01N31/08; A01N31/12; A61; A61K; A61K8/00; A61K8/18; A61K8/72; A61K8/84; A61Q; A61Q5/00; A61Q5/12
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
371 words
A polymeric quaternary ammonium compound and mixtures thereof of formula: ##STR3## wherein Z represents either (1) a divalent aliphatic radical of from 2 to 10 carbon atoms containing from 0 to 2 hydroxyl substituents and from 0 to 2 ethylenic double bonds, and R I and R II may either be (A) the same or different and may be either (a) an alkyl group of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has one alkyl substituent of from 2 to 20 carbon atoms, or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents; (B) R I and R II , taken together with N, form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms; or (C) R I and R II , taken together with N, and combined with an oxygen atom form a N-moropholino group; or (2) Z represents two divalent ethylene radicals, in which case R II is absent and R I represents (a) an aliphatic radical of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has an alkyl substituent of from 2 to 20 carbon atoms; or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents; or (3) Z represents three divalent ethylene radicals in which case R I and R II are both absent; where (1) R III is an aliphatic radical of from 1 to 20 carbon atoms, having from 0 to 2 hydroxyl substituents, and R IV and R V may either be (a) the same or different and represent an aliphatic radical having from 1 to 4 carbon atoms with from 0 to 1 hydroxyl substituents (b) taken together with N to form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms; (c) taken together with N, and combined with an oxygen atom to form a N-morpholino group; or where (2) R III , R IV , R V and N, taken together, represent quinoline, isoquinoline or hexamethylene tetramine; and n is a number of from 1 to 15.
Claim 2
Dependent Claim
371 words
A polymeric quaternary ammonium compound and mixtures thereof of formula: ##STR3## wherein Z represents either (1) a divalent aliphatic radical of from 2 to 10 carbon atoms containing from 0 to 2 hydroxyl substituents and from 0 to 2 ethylenic double bonds, and R I and R II may either be (A) the same or different and may be either (a) an alkyl group of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has one alkyl substituent of from 2 to 20 carbon atoms, or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents; (B) R I and R II , taken together with N, form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms; or (C) R I and R II , taken together with N, and combined with an oxygen atom form a N-moropholino group; or (2) Z represents two divalent ethylene radicals, in which case R II is absent and R I represents (a) an aliphatic radical of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has an alkyl substituent of from 2 to 20 carbon atoms; or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents; or (3) Z represents three divalent ethylene radicals in which case R I and R II are both absent; where (1) R III is an aliphatic radical of from 1 to 20 carbon atoms, having from 0 to 2 hydroxyl substituents, and R IV and R V may either be (a) the same or different and represent an aliphatic radical having from 1 to 4 carbon atoms with from 0 to 1 hydroxyl substituents (b) taken together with N to form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms; (c) taken together with N, and combined with an oxygen atom to form a N-morpholino group; or where (2) R III , R IV , R V and N, taken together, represent quinoline, isoquinoline or hexamethylene tetramine; and n is a number of from 1 to 15.
Claim 3
Dependent Claim
22 words
The mixture of claim 1 wherein at least 50% of the mixture consists of compounds in which n is 2 to 5.
Claim 4
Independent Claim
395 words
The method of conditioning hair which comprises applying to the hair a conditioningly effective amount of an anti-microbial polymeric quaternary ammonium compound or of a mixture of such compounds, said compound having the formula: ##STR4## wherein Z represents either (1) a divalent aliphatic radical of from 2 to 10 carbon atoms containing from 0 to 2 hydroxyl substituents and from 0 to 2 ethylenic double bonds, and R I and R II may either be (A) the same or different and may be either (a) an alkyl group of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has one alkyl substituent of from 2 to 20 carbon atoms, or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents; (B) R I and R II , taken together with N, form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms; or (C) R I and R II , taken together with N, and combined with an oxygen atom, form a N-moropholino group; or (2) Z represents two divalent ethylene radicals, in which case R II is absent and R I represents (a) an aliphatic radical of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has an alkyl substituent of from 2 to 20 carbon atoms; or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents; or (3) Z represents three divalent ethylene radicals in which case R I and R II are both absent; where (1) R III is an aliphatic radical of from 1 to 20 carbon atoms, having from 0 to 2 hydroxyl substituents, and R IV and R V may either be (a) the same or different and represent an aliphatic radical having from 1 to 4 carbon atoms with from 0 to 1 hydroxyl substituents (b) taken together with N to form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms; (c) taken together with N, and combined with an oxygen atom, to form a N-morpholino group; or where (2) R III , R IV , R V and N, taken together, represent quinoline, isoquinoline or hexamethylene tetramine; and n is a number of from 1 to 15.
Claim 5
Independent Claim
395 words
The method of conditioning hair which comprises applying to the hair a conditioningly effective amount of an anti-microbial polymeric quaternary ammonium compound or of a mixture of such compounds, said compound having the formula: ##STR4## wherein Z represents either (1) a divalent aliphatic radical of from 2 to 10 carbon atoms containing from 0 to 2 hydroxyl substituents and from 0 to 2 ethylenic double bonds, and R I and R II may either be (A) the same or different and may be either (a) an alkyl group of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has one alkyl substituent of from 2 to 20 carbon atoms, or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents; (B) R I and R II , taken together with N, form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms; or (C) R I and R II , taken together with N, and combined with an oxygen atom, form a N-moropholino group; or (2) Z represents two divalent ethylene radicals, in which case R II is absent and R I represents (a) an aliphatic radical of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has an alkyl substituent of from 2 to 20 carbon atoms; or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents; or (3) Z represents three divalent ethylene radicals in which case R I and R II are both absent; where (1) R III is an aliphatic radical of from 1 to 20 carbon atoms, having from 0 to 2 hydroxyl substituents, and R IV and R V may either be (a) the same or different and represent an aliphatic radical having from 1 to 4 carbon atoms with from 0 to 1 hydroxyl substituents (b) taken together with N to form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms; (c) taken together with N, and combined with an oxygen atom, to form a N-morpholino group; or where (2) R III , R IV , R V and N, taken together, represent quinoline, isoquinoline or hexamethylene tetramine; and n is a number of from 1 to 15.
Claim 6
Dependent Claim
31 words
The method of claim 3 wherein a mixture of said compounds is used and wherein at least 50% of the mixture consists of compounds in which n is 2 to 5.
Claim 7
Dependent Claim
33 words
The compound of claim 1 wherein R I ═R II ═--CH 3 , R III ═R IV ═R V ═ --CH 2 --CH 2 OH, and Z is --CH 2 CH═CH--CH 2 --.
Claim 8
Dependent Claim
33 words
The method of claim 3 wherein R I ═R II ═--CH 3 , R III ═R IV ═R V ═ --CH 2 --CH 2 OH, and Z is --CH 2 CH═CH--CH 2 --.
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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) | 1981-05-22 | 1981-11-21 | 1982-05-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-22 | 1985-11-21 | 1986-05-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-22 | 1989-11-21 | 1990-05-23 | $7700.00 | Window Closed / Lapsed |