Ester-modified organosilicon-based surfactants, methods of making same and applications containing the same

Patent metadata

Field	Value
Publication number	US-9988404-B2
Application number	US-201615092751-A
Country	US
Kind code	B2
Filing date	Apr 7, 2016
Priority date	Apr 7, 2016
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

There is provided herein a polyalkylene-oxide-free surfactant composition comprising an ester-modified organosilicon having the general formula (I)

AO a R 4 b (BO c R 11 d ) e (C) f D g .

There is also provided methods for making the ester-modified organosilicon (I) and agricultural, coating, personal care and home care applications containing the polyalkylene-oxide-free surfactant composition.

First claim

What is claimed is:

1. A polyalkylene-oxide-free surfactant composition comprising an ester-modified organosilicon having the formula (I):
AO a R 4 b (BO c R 11 d ) e (C) f D g   (I)

where
A=R 1 R 2 R 3 Si—
B=—Si(R 5 )(R 6 )—
C=R 7 R 8 R 9 Si—
D=—O(R 14 ) p R 19
where R 4 and R 11 are each independently selected from a branched or linear divalent hydrocarbon radical of 1 to 12 carbons, subscripts a, b, c, d, e, f, g and p are each 0 or 1 and subject to the following provisos:
a+b=1; when e=1, c+d=1; and, when g=1, then a+e+f=0;
R 1 R 2 R 3 R 5 R 7 R 8 are each independently selected from the group consisting of monovalent hydrocarbon radicals having from 1 to 8 carbon atoms, and an aryl or alkaryl hydrocarbon radical of from 6 to 12 carbon atoms, and R 10 ;
where each R 10 is independently selected from the group consisting of branched monovalent hydrocarbon radicals of from 3 to 6 carbon atoms;
R 6 and R 9 are each independently selected from the group consisting of linear or branched monovalent hydrocarbon radicals containing from 1 to 8 carbon atoms, and R 12 , provided that in formula (I) R 6 and R 9 are different and one of R 6 and R 9 is R 12 ,
wherein R 12 is —R 13 O(R 14 ) p R 19 or a cyclohexyl group of the formula (Q):

where R 13 is selected from a branched or linear divalent hydrocarbon radical containing from 3 to 12 carbon atoms, which is optionally —OH substituted;
R 14 is selected from —CH 2 CH(R 20 )CH 2 O—, —CH 2 (CH 2 ) x CH(R 20 )CH 2 O—, and a bridging group of the formula (Y):
—[C 2 H 4 O] h —[C 3 H 6 O] i —[C 4 H 8 O] j —[C 2 H 4 O] k —[CH 2 CH(R 20 )CH 2 O] n —  (Y);

wherein subscripts h, i, j, and k are zero or one and satisfy the following relationships:
0≤h+i+j+≤1, and 0≤h+k≤1
R 20 is H, OH or —OR 19 ,
subscript x is from 1 to 9,
subscripts p and n are 0 or 1, and
R 15 and R 16 are each independently selected from H or methyl;
R 17 and R 18 are each independently OH or —OR 19 ; provided that in formula (Q) R 17 and R 18 are the same or different, and at least one of R 17 and R 18 is OR 19 ,
where R 19 is derived from the esterification of the corresponding hydroxy carboxylic acid or a mixture of corresponding hydroxy carboxylic acids, which hydroxy carboxylic acid(s) contain(s) from 2 to 8 carbon atoms,
and where R 19 is of the formula (Z):
—C(═O)—CR 21 R 22 R 23   (Z)

where R 21 , R 22 , R 23 are each independently selected from H, —OH, —CH 2 OH, —OZ, —(R 24 ) m O—R 27 , —CH 3 , —CH 2 CH 3 , and —(R 24 ) m O—C(═O)(CR 25 R 26 ) t CH 2 OR 27
where R 24 is a divalent hydrocarbon radical of 1 to 3 carbon atoms,
R 25 and R 26 are each independently selected from H, —OH, —CH 2 OH, —OZ, —(R 24 ) m O—R 27 , —CH 3 , —CH 2 CH 3 , and —(R 24 ) m O—C(═O)—(CR 25 R 26 ) t CH 2 OR 27
R 27 is independently selected from H, Z, —CH 2 OH, —CH 3 , —CH 2 CH 3 , and [—C(═O)(CR 25 R 26 ) t CH 2 O] w —R 29 ,
R 29 is independently selected from H, —CH 2 OH, —CH 3 , and —CH 2 CH 3
subscript m is 0 to 3, t is 1 to 5 and w is 1 to 5; the number of Z groups in R 19 is between 1 and 10; and, provided that when any one or more of R 21 , R 22 and R 23 are of the formula —(R 24 ) m O—C(═O)—(CR 25 CR 26 ) t CH 2 OR 27 that R 21 , R 22 or R 23 group contains from 1 to 10 —(R 24 ) m O—C(═O)—(CR 25 CR 26 ) t CH 2 OR 27 groups; and
provided that ester-modified organosilicon having the formula (I) contains an R 19 group.

2. The composition of claim 1 wherein the ester-modified organosilicon is of the formula (II):
AOC  (II)

wherein:
A=R 1 R 2 R 3 Si—
C=R 7 R 8 R 9 Si—
wherein each of R 2 , R 3 , R 7 and R 8 are methyl,
R 1 is a neo-hexyl group containing six carbon atoms,
R 9 is R 12 , where R 12 is —R 13 O(R 14 ) p R 19
where —R 13 is a divalent hydrocarbon radical having 3 carbon atoms,
R 14 is —CH 2 CH(R 20 )CH 2 O—,
R 20 is OH,
R 19 is —C(═O)—CR 21 R 22 R 23 formula (Z),
where R 22 is methyl
R 21 and R 23 are —(R 24 ) m O—R 27 ,
where R 24 is a divalent hydrocarbon of 1 to 3 carbon atoms,
R 27 is Z or H, providing that

the number of Z groups in R 19 is about 3 to 4,
subscripts m and p are 1; and,

the hydroxy acid is selected from dimethylol propionic acid, glycolic acid, gluconic acid and lactic acid.

3. The composition of claim 1 wherein the ester-modified organosilicon is of the formula (III):
AR 4 C  (III)

wherein
A=R 1 R 2 R 3 Si—
C=R 7 R 8 R 9 Si—
where R 1 , R 2 , R 3 , R 7 and R 8 are methyl,
R 4 is —CH 2 CH 2 —,
R 9 is R 12 , where R 12 is —R 13 O(R 14 ) p R 19
where —R 13 is a divalent hydrocarbon radical having 3 carbon atoms,
R 14 is —CH 2 CH(R 20 )CH 2 O—,
R 20 is OH,
R 19 is —C(═O)—CR 21 R 22 R 23 formula (Z),
where R 22 is methyl
R 21 and R 23 are —(R 24 ) m O—R 27 ,
where R 24 is a divalent hydrocarbon of 1 to 3 carbon atoms,
R 27 is Z or H, providing that the number of Z groups in R 19 is about 3 to 4;
subscripts m and p are 1; and,
the hydroxy acid is selected from dimethylol propionic acid, glycolic acid, gluconic acid and lactic acid.

4. The composition of claim 1 wherein the ester-modified organosilicon is of the formula (IV):
AR 4 BOC  (IV)

wherein
A=R 1 R 2 R 3 Si—
B=—Si(R 5 )(R 6 )—
C=R 7 R 8 R 9 Si—
R 1 , R 2 , R 3 , R 7 and R 8 are methyl,
R 4 is —CH 2 CH 2 —, R 5 is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 8 carbon atoms, and an aryl or alkaryl hydrocarbon radical of from 6 to 12 carbon atoms, and R 10 , where R 10 is selected from the group consisting of branched monovalent hydrocarbon radicals of from 3 to 6 carbon atoms, R 6 is selected from the group consisting of linear or branched monovalent hydrocarbon radicals containing from 1 to 8 carbon atoms,
R 9 is R 12 , where R 12 is —R 13 O(R 14 ) p R 19
where —R 13 is a divalent hydrocarbon radical having 3 carbon atoms,
R 14 is —CH 2 CH(R 20 )CH 2 O—,
R 20 is OH,
R 19 is —C(═O)—CR 21 R 22 R 23 formula (Z),
where R 22 is methyl,
R 21 and R 23 are —(R 24 ) m O—R 27 ,
where R 24 is a divalent hydrocarbon of 1 to 3 carbon atoms,
R 27 is Z or H, providing that the number of Z units in R 19 is about 4 to 6,
subscripts m and p are 1; and,
the hydroxy acid is selected from dimethylol propionic acid, glycolic acid, gluconic acid and lactic acid.

5. The composition of claim 1 wherein the ester-modified organosilicon is of the formula (V):
AR 4 C  (V)

wherein
A=R 1 R 2 R 3 Si—
C=R 7 R 8 R 9 Si—
R 1 , R 2 , R 3 , R 7 and R 8 are methyl,
R 4 is —CH 2 CH 2 —,
R 9 is R 12 , where R 12 is —R 13 OR 19
where —R 13 is a divalent hydrocarbon radical having 3 carbon atoms,
R 19 is —C(═O)—CR 21 R 22 R 23 formula (Z),
wherein R 21 and R 23 are H,
R 22 is —(R 24 ) m O—R 27 ,
where R 24 is a divalent hydrocarbon of 1 to 3 carbon atoms,
R 27 is Z or H providing that the number of Z groups in R 19 is about 4 to 5,
subscript m is 1; and,
the hydroxy acid is selected from dimethylol propionic acid, glycolic acid, gluconic acid and lactic acid.

6. The composition of claim 1 wherein the ester-modified organosilicon is of the formula (VI):
AOBOC  (VI)

wherein,
A=R 1 R 2 R 3 Si—
B=—Si(R 5 )(R 6 )—
C=R 7 R 8 R 9 Si—
R 1 , R 2 , R 3 , R 7 , R 8 and R 9 are methyl R 5 is selected from the group consisting of a monovalent hydrocarbon radical having from 1 to 8 carbon atoms, and an aryl or alkaryl

Assignees

• Momentive Performance Mat Inc

Inventors

• Policello George A
• Mukherjee Narayan
• Wagner Roland
• Leatherman Mark D

Classifications

• A01N57/20 Primary

  containing acyclic or cycloaliphatic radicals · CPC title

• A61Q3/02

  Nail coatings · CPC title

• C07F7/0827

  Syntheses with formation of a Si-C bond · CPC title

• A01N25/30

  characterised by the surfactants · CPC title

• A61Q3/04

  Nail coating removers · CPC title