IP Library Granted Patent US 9,138,398
Granted Patent B2
US 9,138,398 · App. 13/765,235 · Granted Sep 22, 2015

Cationic alcohols and uses thereof

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Quick Facts
Patent No.
US 9,138,398
App. No.
13/765,235
Granted
Sep 22, 2015
Kind
B2
Abstract

Compositions are disclosed comprising novel fluorinated cationic alcohols in a cosmetically acceptable vehicle. The fluorinated compounds alter a surface property of the hair to provide hair conditioning, for example. In embodiments, the compounds have improved water solubility and deposition properties.

Claims (53)

1. A compound prepared by reacting a tertiary amine with a fluorinated epoxide,

wherein the tertiary amine has the structure

wherein R 2′ , R 3′ , R 4′ , R 5′ , R 6′ and R 7′ are the same or different C 1-6 alkyl group, which may be substituted with hydroxyl, carboxy, alkoxy or acyloxy groups,

o is an integer from 1 to 20,

wherein the fluorinated epoxide has the structure

wherein R f is a fluorinated organic group with a terminal CHF 2 group,

wherein the fluorinated organic group is a branched or straight chain fluorinated aliphatic group, a straight or branched chain fluorinated heteroaliphatic group, a fluorinated acyl group, a fluorinated aryl or fluorinated heteroaryl group, and

the compound contains at least one quaternary ammonium moiety, at least one hydroxyl group, at least two fluorine atoms, and a terminal CHF 2 group,

or a cosmetically acceptable salt thereof,

wherein the compound has the structure

wherein,

X 1 is O or —(CH 2 ) m —;

R 11 , R 12 and R 13 are independently C 1-6 alkyl or C 1-6 hydroxyalkyl;

m is an integer from 1 to 20; and

n is an integer from 1 to 20;

or a cosmetically acceptable salt thereof.

2. The compound of claim 1 , wherein the compound has the structure

3. A compound prepared by reacting a tertiary amine with a fluorinated epoxide,

wherein the tertiary amine has the structure

wherein R 2′ , R 3′ , R 4′ , R 5′ , R 6′ and R 7′ are the same or different C 1-6 alkyl group, which may be substituted with hydroxyl, carboxy, alkoxy or acyloxy groups,

o is an integer from 1 to 20,

wherein the fluorinated epoxide has the structure

wherein R f is a fluorinated organic group with a terminal CHF 2 group,

wherein the fluorinated organic group is a branched or straight chain fluorinated aliphatic group, a straight or branched chain fluorinated heteroaliphatic group, a fluorinated acyl group, a fluorinated aryl or fluorinated heteroaryl group, and

the compound contains at least one quaternary ammonium moiety, at least one hydroxyl group, at least two fluorine atoms, and a terminal CHF 2 group,

or a cosmetically acceptable salt thereof,

wherein the compound has the structure

wherein,

X 1 is —(CH 2 —CH 2 —O) p —;

R 11 , R 12 and R 13 are independently C 1-6 alkyl or C 1-6 hydroxyalkyl;

p is an integer from 1 to 10,000; and

n is an integer from 1 to 20;

or a cosmetically acceptable salt thereof.

4. A compound prepared by reacting a tertiary amine with a fluorinated epoxide,

wherein the tertiary amine is a diamine with the structure

wherein R 4′ , R 5′ , R 6′ and R 7′ are the same or different C 1-6 alkyl group, which may be substituted with hydroxyl, carboxy, alkoxy or acyloxy groups,

o is an integer from 1 to 20,

wherein the fluorinated epoxide has the structure

wherein R f is a fluorinated organic group with a terminal CHF 2 group,

wherein the fluorinated organic group is a branched or straight chain fluorinated aliphatic group, a straight or branched chain fluorinated heteroaliphatic group, a fluorinated acyl group, a fluorinated aryl or fluorinated heteroaryl group, and

the compound contains at least one quaternary ammonium moiety, at least one hydroxyl group, at least two fluorine atoms, and a terminal CHF 2 group,

or a cosmetically acceptable salt thereof,

wherein the compound has the structure

wherein,

A′ and A″ are independently CH 2 , CHF or CF 2 ;

X′ and X″ are independently O, CF 2 , or —(CH 2 ) m —;

R 5 and R 10 are the same or different organic groups, each substituted with at least two fluorine atoms;

R 6 and R 9 are independently substituted or unsubstituted C 1-6 alkyl, and R 6 and R 9 may join to form a ring;

R 7 and R 8 are independently substituted or unsubstituted C 1-6 alkyl, and R 7 and R 8 may join to form a ring;

n is an integer from 1 to 6; and

m is an integer from 1 to 20,

or a cosmetically acceptable salt thereof.

5. The compound of claim 4 , wherein the compound has the structure

Assignments (2)
RELEASE OF SECURITY INTEREST Recorded Jan 31, 2017
From: PACIFIC WESTERN BANK
To: LIVING PROOF, INC.
Reel/Frame 041131/0464 →
SECURITY INTEREST Recorded Apr 6, 2016
From: LIVING PROOF, INC.
To: PACIFIC WESTERN BANK
Reel/Frame 038206/0301 →