# US 4,395,541 A · Ionene polymer and preparation thereof

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- Number: US 4,395,541 A
- Document ID: US4395541A
- Status: Granted
- Kind: A
- Application number: 06/217,402
- Filed: 1980-12-17
- Granted: 1983-07-26
- Earliest claimed: 1979-12-21
- Assignees: Societe Anonyme dite: L'Oreal
- Inventors: Bernard Jacquet; Gerard Lang; Alain Malaval; Serge Forestier; Do Le Trung
- Web page: https://patentgrep.com/patent/US4395541A

## CPC

- A61K 8/84: obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/12: Preparations containing hair conditioners
- C08G 73/0253: {Polyamines containing sulfur in the main chain}
- C08G 73/0293: {Quaternisation of polyamidoamines}
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Ionene polymers have been prepared and have been found to be useful in cosmetic compositions for the treatment of the hair and skin, or in the treatment of natural or synthetic textile fibers. These polymers comprise units of the formula ##STR1##

## Claims

### Claim 1

A polymer having units of the formula ##STR24## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, each independently represent a hydrocarbon group containing up to 20 carbon atoms, or at least one pair selected from the group consisting of R.sub.1, R.sub.2 and R.sub.3, R.sub.4, together with the nitrogen atom to which it is attached, forms a heterocycle selected from the group consisting of a heterocycle wherein the heteroatom is nitrogen and a heterocycle containing nitrogen as a first heteroatom and a second heteroatom selected from the group consisting of oxygen and sulfur;
A.sub.1 and A.sub.2 each independently represents a linear or branched alkylene, or aryl, containing up to 20 carbon atoms;
X represents --SO.sub.2 -- or --CO--;
R.sub.5 and R.sub.6 represent hydrogen or lower alkyl when X represents --SO.sub.2 --;
or R.sub.5 and R.sub.6, together, represent ##STR25## when X represents --CO--; R.sub.7 and R.sub.8 represent hydrogen or lower alkyl;
A.sub.3 represents alkylene, cycloalklene, alkenylene or cycloalkenylene, containing 2 to 20 carbon atoms, or at least one or said alkylene, cycloalkylene, alkenylene and cycloalkylene, interrupted by at least one heteroatom or by at least one of an arylene or cycloalkylene group, or
A.sub.3 represents polyoxyalkylene or --B.sub.1 --D--B.sub.2 -- wherein B.sub.1 and B.sub.2 represent alkylene having from 1 to 12 carbon atoms, or arylene, and D represents a member selected from the group consisting of ##STR26## --CONH--, --CO--O--, --O--CONH--, --CO--D.sub.2 --CO-- and --O--CO--D.sub.3 --CO--O--,
wherein
D.sub.1 represents alkylene, alkylene interrupted by a --S--S-- group, alkenylene, arylene, diaminoalkylene, diaminoarylene, dioxyalkylene, polyoxyalkylene or dioxyarylene, or
D.sub.1 represents a direct covalent bond,
y is a number equal to 0 or 1,
R.sub.10 and R.sub.11 represent hydrogen or lower alkyl, or when y is 0, R.sub.10 and R.sub.11, together, represent ##STR27## D.sub.2 represents diaminoalkylene, dioxyalkylene, polyoxyalkylene or dithioalkylene,
D.sub.3 represents alkylene, arylene, diaminoalkylene, diaminocycloalkylene or diaminoarylene, or
A.sub.3, together with the two nitrogens to which it is attached and with at least one of the pairs R.sub.1, R.sub.3 and R.sub.2, R.sub.4, represents a cyclic or polycyclic group having from 4 to 6 carbon atoms; and
Z.sup..crclbar. represents an anion.

### Claim 2 (depends on 1)

The polymer of claim 1 wherein, when A.sub.3 represents alkylene or cycloalkylene, A.sub.3 represents a member selected from the group consisting of ##STR28## wherein R.sub.12 and R.sub.13 represent hydrogen, lower alkyl, lower hydroxyalkyl, halogen, carboxy, alkoxycarbonyl or phenyl,
Y represents a direct covalent bond, or Y represents --O--, --CO--, --CHOH--, --SO.sub.2 -- or alkylene,
n is a number ranging from 1 to 6; and
p is a number ranging from 1 to 3.

### Claim 3 (depends on 1)

The polymer of claim 1 wherein, when A.sub.3 represents a cyclic or polycyclic group, A.sub.3 represents a member selected from the group consisting of ##STR29## where R.sub.2 and R.sub.4 are defined in claim 1.

### Claim 4 (depends on 1)

The polymer of claim 1 wherein Z.sup.- represents an anion derived from a mineral acid or low molecular weight organic acid.

### Claim 5 (depends on 4)

The polymer of claim 4 wherein Z.sup.- represents a halide, nitrate, sulfate, acetate or paratoluene sulfonate anion.

### Claim 6 (depends on 1)

The polymer of claim 1 wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each independently, represent an aryl, aliphatic, alicyclic or arylaliphatic group containing a maximum of 20 carbon atoms.

### Claim 7 (depends on 6)

The polymer of claim 6 wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each independently represent alkyl or hydroxyalkyl containing 1-8 carbon atoms, cycloalkyl-alkyl having less than 20 carbon atoms, cycloalkyl having 5 or 6 carbon atoms or aralkyl wherein the alkyl group contains 1-3 carbon atoms.

### Claim 8 (depends on 1)

The polymer of claim 1 wherein, when at least one of the pairs R.sub.1, R.sub.2 and R.sub.3, R.sub.4 together with the nitrogen atom to which it is attached forms a ring, said pair represents a polymethylene group having 2 to 6 carbon atoms.

### Claim 9 (depends on 1)

The polymer of claim 1 wherein A.sub.1 and A.sub.2 each independently represents linear or branched alkylene having 1-12 carbon atoms or linear or branched alkylene having 1-12 carbon atoms substituted by 1-4 branched alkyl substituents wherein said alkyl contains 1-10 carbon atoms.

### Claim 10 (depends on 1)

The polymer of claim 1 wherein A.sub.3 represents --B.sub.1 --D--B.sub.2 -- wherein D represents --N(R.sub.10)--(CO--D.sub.1).sub.y CO--N(R.sub.11)-- wherein D.sub.1 represents linear or branched alkylene having 1-12 carbon atoms, linear or branched alkylene having 1-12 carbon atoms and having at least one branched alkyl substituent having 1-10 carbon atoms, linear or branched alkylene having 1-12 carbon atoms and being interrupted by a --S--S-- group or linear or branched alkylene having 1-12 carbon atoms and including an --NH-- or --O-- group at each end thereof, or D.sub.1 represents arylene having 6-20 carbon atoms, arylene having 6-20 carbon atoms and being substituted by at least one allyl group having 1-3 carbon atoms or arylene having 6-20 carbon atoms and including an --NH-- or --O-- group at each end.

### Claim 11 (depends on 1)

The polymer of claim 1 wherein D.sub.2 represents --NH--alkylene--NH--, --O--alkylene--O-- or --S--alkylene-S- wherein the alkylene moiety has 1-12 carbon atoms.

### Claim 12 (depends on 1)

The polymer of claim 1 wherein D.sub.3 is linear or branched alkylene having 1-12 carbon atoms, linear or branched alkylene having 1-12 carbon atoms and having at least one branched alkyl substituent having 1-10 carbon atoms or linear or branched alkylene having 1-12 carbon atoms and having an --NH-- group at each end thereof or D.sub.3 is arylene having 6-20 carbon atoms, arylene having 6-20 carbon atoms and being substituted by at least one alkyl group, or arylene having 6-20 carbon atoms and having an --NH-- group at each end thereof.

### Claim 13 (depends on 1)

The polymer of claim 1 wherein D.sub.3 represents cycloalkylene or --NH--cycloalkylene--NH-- wherein said cycloalkylene has from 5 to 20 carbon atoms.

### Claim 14 (depends on 8)

The polymer of claim 8 wherein said ring contains a heteroatom selected from the group consisting of oxygen and sulfur.

### Claim 15

A polymer having units of the formula ##STR30## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each independently represent alkyl having up to 20 carbon atoms;
A.sub.1 and A.sub.2 each independently represent alkylene containing up to 20 carbon atoms;
X represents --CO--;
R.sub.5 and R.sub.6, together, represent ##STR31## wherein R.sub.7 and R.sub.8 represent hydrogen or lower alkyl, A.sub.3 represents alkylene containing 2 to 20 carbon atoms, and
Z.sup.- represents an anion.

### Claim 16 (depends on 15)

The polymer of claim 15, wherein A.sub.1 equals A.sub.2 equals --(CH.sub.2).sub.3 --; R.sub.1 equals R.sub.2 equals R.sub.3 equals R.sub.4 equals CH.sub.3 ; R.sub.5 and R.sub.6, together, represent --CH.sub.2 --O--CH.sub.2 --; A.sub.3 equals --(CH.sub.2).sub.6 -- and Z.sup.- equals Cl.sup.-.

### Claim 17 (depends on 1, 39)

A process for preparing the polymer of claim 1 comprising polycondensing at least one amine selected from the group consisting of an amine of the formula R.sub.1 R.sub.2 N--A.sub.1 --N(R'.sub.5)--X--N(R'.sub.6)--A.sub.2 --N--R.sub.3 R.sub.4 (II) wherein R'.sub.5 and R'.sub.6 have the meanings given for R.sub.5 and R.sub.6 in claim 39 or R'.sub.5 and R'.sub.6 also represent hydrogen when X represents --CO-- and an amine of the formula R.sub.1 R.sub.2 N--A.sub.3 --NR.sub.3 R.sub.4 (III) with at least one dihalide selected from the group consisting of Z--A.sub.3 --Z and Z--A.sub.1 --N(R.sub.5)--X--N(R.sub.6)--A.sub.2 --Z, wherein R.sub.1, R.sub.2, A.sub.1, X, A.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and A.sub.3 have the meanings given in claim 1, with the proviso that when R'.sub.5 equals R'.sub. 6 equals H and X equals --CO--, the resulting intermediate polymer is reacted in the presence of an acid catalyst with an aldehyde having the formula R.sub.7 --CHO wherein said aldehyde is present in an amount of two moles thereof per --NH--CO--NH-- group present in said intermediate polymer so as to produce the polymer of claim 1.

### Claim 18 (depends on 17)

The process of claim 17 wherein said amine of formula II for which X represents --CO-- and R.sub.5 and R.sub.6, together, represent --CH(R.sub.7)--O--CH(R.sub.8)-- is prepared by reacting at least one amine of the formula R.sub.1 R.sub.2 N--A.sub.1 --NHCONH--A.sub.2 --NR.sub.3 R.sub.4 with at least one aldehyde selected from the group consisting of R.sub.7 CHO and R.sub.8 CHO in an acid environment so as to form the salt of the resulting amine and thereafter transforming said salt into the free amine by reaction with a base.

### Claim 19 (depends on 17)

The process of claim 17 wherein said amine of formula II for which X represents --SO.sub.2 -- is prepared by reacting at least one amine selected from the group consisting of R.sub.1 R.sub.2 N--A.sub.1 --NHR.sub.5 and R.sub.1 R.sub.2 N--A.sub.1 --NHR.sub.6 with sulfuryl chloride wherein said amine is present in an amount of two moles thereof per mole of sulfuryl chloride so as to form the salt of the resulting amine and thereafter transforming said salt into the free amine by reaction with a base.