Quaternary organosilicon surfactants, methods of making same and applications containing the same

Patent metadata

Field	Value
Publication number	US-2016100573-A1
Application number	US-201414524430-A
Country	US
Kind code	A1
Filing date	Oct 27, 2014
Priority date	Oct 10, 2014
Publication date	Apr 14, 2016
Grant date	—

Abstract

There is provided herein a surfactant composition comprising quaternary organosilicons having the general formula (I)
AO a R 4 b (BO c R 11 d ) e C.
There is also provided methods for making the quaternary organosilicons (I) and agricultural, coating, personal care and home care applications containing the quaternary organosilicons.

First claim

What is claimed is:

1 . A surfactant composition comprising a quaternary organosilicon salt having the general formula (I):
AO a R 4 b (BO c R 11 d ) e C  (I)

wherein:
A=R 1 R 2 R 3 Si—;
B=—Si(R 5 )(R 6 )—;
C=R 7 R 8 R 9 Si—;
subscripts a, b, c, d and e are 0 or 1 and subject to the following relationships: a+b=1 and when e=1, c+d=1;
R 1 , R 2 , R 3 , R 5 , R 7 , R 8 are each independently selected from the group consisting of monovalent hydrocarbon groups containing from 1 to 8 carbon atoms, monovalent aryl and alkaryl hydrocarbon groups containing from 6 to 12 carbon atoms, and R 10 ,
where R 10 is selected from the group consisting of branched monovalent hydrocarbon groups containing from 3 to 6 carbon atoms;
R 4 and R 11 are each independently a divalent hydrocarbon group containing from 1 to 4 carbon atoms;
R 6 and R 9 are each independently selected from the group consisting of linear or branched monovalent hydrocarbon groups containing from 1 to 8 carbon atoms, and R 12 , provided that R 6 and R 9 are different and one of R 6 or R 9 is R 12 ,
wherein R 12 is selected from R* or —R 13 R 14 N ⊕ (R 15 )(R 16 )R 17 X {grave over (Y)} ,
wherein R* is

Wherein R 19 and R 20 are independently selected from H or Methyl,
R 21 and R 22 are different, and selected from OH or R 23 ;
R 23 is —N ⊕ (R 15 )(R 16 )R 17 X {grave over (Y)} ,
wherein R 13 is a divalent hydrocarbon group containing from 3 to 12 carbon atoms, and optionally substituted by one or more hydroxyl groups,
R 14 is selected from the group consisting of —OCH 2 CH(OH)CH 2 — and an alkyleneoxide group of the general formula (II):
—[OC 2 H 4 ] h —[OC 3 H 6 ] i —[OC 4 H 8 ] k —OCH 2 CH(OH)CH 2 —  (II)

wherein subscripts h, i and k are zero or positive and satisfy the following relationships: 1≦h+i+k≦15, more specifically, 1≦h+i+k≦10, even more specifically h is from 0 to 8, i is from 0 to 5 and k is from 0 to 4,
R 15 and R 16 are independently selected from the group consisting of a monovalent hydrocarbon group containing from 1 to 2 carbon atoms,
R 17 is selected from the group consisting of linear or branched hydrocarbon groups containing from 1 to 6 carbon atoms, which may each be optionally substituted with one or more hydroxyl groups, and an alkyleneoxide group of the general formula (III):
[OC 2 H 4 ] m —[OC 3 H 6 ] n −[OC 4 H 8 ] p —R 18   (III)

wherein subscripts m, n and p are zero or positive and satisfy the following relationships: 1≦m+n+p≦15,
R 18 is selected from the group consisting of —OH and monovalent hydrocarbon groups containing from 1 to 4 carbon atoms; and
X {grave over (Y)} is R 34 , or a more biodegradable group R PE ,
R 34 is selected from the group consisting of carboxylic acid anion moiety containing from 2 to 22 carbon atoms, and has the general formula:
{grave over (Y)} O—C(═O)—C(R 35 )(R 36 )(R 37 )

wherein subscripts q, r and s are 0 or 1,
R 35 and R 36 are selected from H, OH, a hydrocarbon group of 1-3 carbon atoms or CH 2 OH,
R 37 is selected from H, OH, a hydrocarbon group of 1-3 carbon atoms, CH 2 OH or —(CH R 38 ) f —CH 2 R 39 ,
wherein R 38 is H, OH, a hydrocarbon group of 1-3 carbon atoms or CH 2 OH; R 39 is H or OH,
subscript f is 0 to 3,
where R PE is a polyester moiety derived from the esterification of the corresponding hydroxy carboxylic acid or a mixture of corresponding hydroxy carboxylic acids and carboxylic acids, wherein the hydroxy carboxylic acid(s) contain(s) from 2 to 8 carbon atoms, and R PE is of the general formula (Z):
{grave over (Y)} O—C(═O)—CH (3-[q+r+s]) (R 24 ) q (R 25 ) r (R 26 ) s   (Z)

subscripts q, r and s are 0 or 1,
where R 24 , R 25 , R 26 are independently selected from —OH, —CH 2 OH, —(CH 2 ) m OR 27 , —CH 3 , —CH 2 CH 3 , —(CH 2 ) m O—C(═O)(CR 30 R 31 ) t CH 2 OR 32 , or R 28 ,
where R 27 is —C(═O)—CH (3-[q+r+s]) (R 24 ) q (R 25 ) r (R 26 ) s
R 28 is —R 29 OR 27 , where R 29 is a divalent hydrocarbon radical of 2 to 6 carbon atoms,
R 30 and R 31 are independently selected from H, —OH, —CH 2 OH, —(CH 2 ) m O—R 27 , —CH 3 , —CH 2 CH 3 , or —(CH 2 ) m O—C(═O)—(CR 30 R 31 ) t CH 2 OR 32 ,
R 32 is independently selected from H, —CH 2 OH, —CH 3 , —CH 2 CH 3 , R 27 , or [—C(═O)(CR 30 R 31 ) t CH 2 O] w —R 33 ,
R 33 is independently selected from H, —CH 2 OH, —CH 3 , or —CH 2 CH 3 ,
where,
subscript m is 0 to 3,
subscript t is 1 to 5,
subscript w is 1 to 5, and
the number of ester linkages in R PE is between 1 and 10,
provided that when any one or more of R 24 , R 25 and R 26 are of the formula —(CH 2 ) m O—C(═O)(CR 30 R 31 ) t CH 2 OR 32 that R 24 , R 25 and R 26 group contains from 1 to 10 —(CH 2 ) m O—C(═O)(CR 30 R 31 ) t CH 2 OR 32 groups.

2 . The composition of claim 1 wherein X {grave over (Y)} is selected from the group consisting of anions of monocarboxylic acids, dicarboxylic acids, alpha-hydroxyl acids, beta-hydroxyl acids, dihydroxy acids and saturated and unsaturated fatty acids.

3 . The composition of claim 1 wherein the quaternary organosilicon has the general formula (IV):
AR 4 C  (IV)

wherein:
A=R 1 R 2 R 3 Si—; and
C=R 7 R 8 R 9 Si—;
wherein R′, R 2 , R 3 , R 7 and R 8 are methyl;
R 4 is —CH 2 CH 2 —;
R 9 is R 12 ,
wherein R 12 is —R 13 R 14 N ⊕ (R 15 )(R 16 )R 17 X {grave over (Y)} ,
wherein R 13 is —CH 2 CH 2 CH 2 —;
R 14 is —OCH 2 CH(OH)CH 2 —;
R 15 and R 16 are methyl;
R 17 is —CH 2 CH(OH)CH 2 —OH; and
X {grave over (Y)} is CH 3 C(CH 2 OH) 2 COO—.

4 . The composition of claim 1 wherein the quaternary organosilicon has the general formula (V):
AR 4 BOC  (V)

wherein:
A=R 1 R 2 R 3 Si—;
B=—Si(R 5 )(R 6 )—; and
C=R 7 R 8 R 9 Si—;
wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are methyl;
R 9 is R 12 ;
wherein R 12 is —R 13 R 14 N ⊕ (R 15 )(R 16 )R 17 X {grave over (Y)} ,
wherein R 13 is —CH 2 CH 2 CH 2 —;
R 14 is —OCH 2 CH(OH)CH 2 —;
R 15 and R 16 are methyl;
R 17 is —CH 2 CH 2 CH 2 OH; and)
X {grave over (Y)} is CH 3 C(CH 2 OH) 2 COO—.

5 . The composition of claim 1 wherein the quaternary organosilicon has the general formula (V-B):
AOBOC  (V-B)

wherein:
A=R 1 R 2 R 3 Si—;
B=—Si(R 5 )(R 6 )—; and
C=R 7 R 8 R 9 Si—;
wherein R 1 , R 2 , R 3 , R 5 , R 7 , R 8 and R 9 are methyl;
R 6 is R 12 ;
wherein R 12 is —R 13 R 14 N ⊕ (R 15 )(R 16 )R 17 X {grave over (Y)} ,
wherein R 13 is —CH 2 CH 2 CH 2 —;
R 14 is —OCH 2 CH(OH)CH 2 —;
R 15 and R 16 are methyl;
R 17 is —CH 2 CH 2 CH 2 OH; and
X {grave over (Y)} is CH 3 C(CH 2 OH) 2 COO—.

6 . A method of making quaternary organosilicon having the general formula (I) of claim 1 comprising:
(a) reacting a hydride intermediate with an olefinically-modified intermediate in the presence of a catalyst,

wherein:
the hydride intermediate has the general formula (VI):
AO a R 4 b (B H O c R 11 d ) e C H   (VI)

wherein:
A=R 1 R 2 R 3 Si—;
B H =—Si(R 5 )(R 6H )—;
C H =R 7 R 8 R 9H Si—;
subscripts a, b, c, d and e are 0 or 1 and subject to the following relationships: a+b=1 and c+d=1 (when e=1);
R 1 , R 2 , R 3 , R 5 , R 7 , R 8 are independently selected from the group consisting of monovalent hydrocarbon groups containing from 1 to 8 carbon atoms, monovalent aryl and alkaryl hydrocarbon groups containing from 6 to 12 carbon atoms, and R 10 ,
wherein

Assignees

• Momentive Performance Mat Inc

Inventors

• Policello George A
• Mukherjee Narayan

Classifications

• A01N25/30 Primary

  characterised by the surfactants · CPC title

• C07F7/0854

  Chemistry & Metallurgy · mapped topic

• C07F7/0872

  Preparation and treatment thereof · CPC title

• A01N57/20

  containing acyclic or cycloaliphatic radicals · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title