Compositions comprising carbamate functionalized organopolysiloxanes and cationic surfactants

Patent metadata

Field	Value
Publication number	US-10675230-B2
Application number	US-201716096150-A
Country	US
Kind code	B2
Filing date	Apr 24, 2017
Priority date	Apr 26, 2016
Publication date	Jun 9, 2020
Grant date	Jun 9, 2020

Abstract

Emulsions of carbamato-functional organopolysiloxanes emulsified with the aid of cationic emulsifiers are useful for treating textiles to provide good haptic properties, and also in hair care products.

First claim

The invention claimed is:

1. An aqueous composition, comprising:
(A) at least 0.1% by weight and at most 10.0% by weight of at least one carbamato-functionalized organopolysiloxane comprising, on average, per molecule, at least one carbamato-functionalized group Y of the formula:
—R 4 —[NX—R 5 —] n NX—H

where
X is the same or different and is a hydrogen atom or a Z radical of the formula:
—CO—O—CHR 6 —CH 2 —OH or —CO—O—CH 2 —CHR 6 —OH

wherein in the carbamato-functionalized organopolysiloxane (A), at least 5 mol % and less than 50 mol % of the N-bonded X radicals in the Y groups are not a hydrogen,
where on average at least one X radical per molecule is a Z radical,
where R 4 is the same or different and is a divalent, Si—C-bonded hydrocarbyl radical having 1 to 18 carbon atoms,
R 5 is the same or different and is a divalent hydrocarbyl radical having 1 to 6 carbon atoms,
R 6 is the same or different and is a hydrogen atom or a monovalent hydrocarbyl radical having 1 to 36 carbon atoms, where one or more —CH 2 — groups may be replaced by a heteroatom,
n is 1, 2, 3 or 4,
(B) at least 1% by weight of one or more cationic surfactants, and
(C) at least 30% by weight and at most 97% by weight of water,
the weight percentages based in each case on the total weight of the aqueous composition.

2. The composition of claim 1 , wherein at least one carbamato-functionalized organopolysiloxane (A) comprises a carbamato-functionalized polydiorganosiloxane of the formula
[R 1 2 R 2 SiO 1/2 ] 2 [R 2 (Y)SiO 2/2 ] k [R 1 2 SiO 2/2 ] m   (I)

where
R 1 is the same or different and is a monovalent Si—C-bonded hydrocarbyl radical having 1 to 18 carbon atoms,
R 2 is the same or different and is a R 1 radical or a hydroxyl group —OH or alkoxy group of the formula —O—R 3 where R 3 is an optionally substituted alkyl radical having 1-8 carbon atoms, where on average at least one Y group per molecule contains a Z radical of the formula
—CO—O—CHR 6 —CH 2 —OH or —CO—O—CH 2 —CHR 6 —OH,

where
m is an integer and is at least 40 and at most 1000,
k is an integer and is at least 1 and at most 40,
where the ratio of m to k is at least 25 and at most 1000.

3. The composition of claim 1 , wherein in the carbamato-functionalized organopolysiloxane (A), at least 15 mol % and less than 40 mol % of the N-bonded X radicals in the Y groups are not a hydrogen, but are defined as a Z radical of the formula:
—CO—O—CHR 6 —CH 2 —OH or —CO—O—CH 2 —CHR 6 —OH

4. The composition of claim 1 , wherein R 6 is a methyl radical.

5. The composition of claim 1 , the carbamato-functionalized organopolysiloxane(s) (A) are in the form of aqueous emulsions thereof comprising carbamato-functionalized organopolysiloxane (A), nonionic and/or cationic emulsifiers and water.

6. The composition of claim 1 , wherein the cationic surfactants comprises:
(B1) quaternary ammonium surfactants of the formula

where R is independently a hydrogen atom, an alkyl group, a hydroxyalkyl group, a benzyl group or a group of the formula —(C p H 2p O) q —H where p is an integer from 1 to 4 and q is an integer from 2 to 5, and
X − is a halide, a sulfate, a sulfonate, a nitrate, a methylsulfate or an ethylsulfate anion,
or
(B2) ester/amido-containing quaternary ammonium surfactants of the formula

where at least one R 20 radical is a monovalent hydrocarbyl radical containing a G group of the formula
—O—(O)C—, —C(O)—O—, —NR—C(O)—, or —C(O)—NR— or

CR═NR,

and the further R 20 radicals are independently an R group
or a radical of the formula —R 20 ′—N+R 20 3 X −
where R 20′ is an alkylene group,
the two ammonium groups R 20 3N + X − are joined to one another to form an R 20 3 N-alkylene-NR 20 3 2X − compound,
or two R 20 radicals form an optionally unsaturated ring, and
R and X − are as defined above.

7. The composition of claim 6 , wherein the ester/amido-containing quaternary ammonium surfactants (B2) used comprise those selected from the group consisting of (B2-1) surfactants of the formula
R 25 (4-f) (R 26 -G 1 -R 27 ) r N + X −   (B2-1)

where
R 25 is independently a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group having 1 to 3 carbon atoms, a benzyl group or a group of the formula —(C p H 2p O) q —H where p is an integer from 1 to 4, preferably 2, and q is an integer from 2 to 5,
R 26 is a monovalent hydrocarbyl radical, preferably an alkyl or alkenyl radical having 12 to 24 carbon atoms,
R 27 is a divalent linear or branched alkylene radical having 1 to 6 carbon atoms,
G 1 is a —O—(O)C—, —C(O)—O—, —NR—C(O)—, or —C(O)NR-group,
r is 2 or 3 and
X − is a halide, a sulfate, a sulfonate, a nitrate, a methylsulfate or an ethylsulfate anion,
(B2-2) surfactants of the formula

where
R 25 , R 26 , G 1 and X − are as defined above,
(B2-3) surfactants of the formula

where
G 2 is an oxygen atom or the NR 25 group,
R 25 , R 26 , R 27 and X − are as defined above,
(B2-4) surfactants of the formula

where
R 25 , R 26 , R 27 and X − are as defined above,
(B2-5) surfactants of the formula

where
R 25 , R 26 , R 27 and X − are as defined above,
and mixtures thereof.

8. The composition of claim 1 , wherein the carbamato-functionalized organopolysiloxanes (A) are prepared by reaction of amino-functionalized organopolysiloxanes (A′) containing on average per molecule at least one Y′ group of the formula
—R 4 —[NH—R 5 -] n NH 2

with cyclic carbonates of the formula

9. The composition of claim 8 , wherein the amino-functionalized organopolysiloxanes (A′) comprise amino-functionalized polydiorganosiloxanes (A′) of the formula
[R 1 2 R 2 SiO 1/2 ] 2 [R 2 (Y′)SiO 2/2 ] k [R 1 2 SiO 2/2 ] m   (I′)

where
R 1 is the same or different and is a monovalent Si—C-bonded hydrocarbyl radical having 1 to 18 carbon atoms,
R 2 is the same or different and is an R 1 radical or a hydroxyl group —OH or an alkoxy group of the formula —O—R 3 where R 3 is an optionally substituted alkyl radical having 1-8 carbon atoms, where on average at least one Y group per molecule contains a Z radical of the formula
—CO—O—CHR 6 —CH 2 —OH or —CO—O—CH 2 —CHR 6 —OH,

where
m is an integer and is at least 40 and at most 1000,
k is an integer and is at least 1 and at most 40, and
Y′ group of the formula
—R 4 —[NH—R 5 -] n NH 2 .

10. The composition of claim 9 , wherein the amino-functionalized organopolysiloxanes (A′) have an amine value of at most 0.4 mmol/g.

11. The composition of claim 8 , wherein the amino-functionalized organopolysiloxanes (A′) have an amine value of at most 0.4 mmol/g.

12. A washing or cleaning composition comprising a composition of claim 1 .

13. A method of fiber

Assignees

• Wacker Chemie Ag

Inventors

• Brehm Christof
• Becker Richard
• Hoelzlwimmer Elisabeth
• Stalleicher Christine

Classifications

• A61Q5/02

  Preparations for cleaning the hair · CPC title

• A61Q5/12

  Preparations containing hair conditioners · CPC title

• C11D3/0015 Primary

  liquid · CPC title

• C11D3/3742

  Nitrogen containing silicones · CPC title

• A61K8/898

  containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine · CPC title