Silicon-containing zwitterionic linear copolymer composition

Patent metadata

Field	Value
Publication number	US-9200119-B2
Application number	US-201213673094-A
Country	US
Kind code	B2
Filing date	Nov 9, 2012
Priority date	Nov 9, 2012
Publication date	Dec 1, 2015
Grant date	Dec 1, 2015

Abstract

A silicon-containing copolymer which includes zwitterionic linking groups with the general structures —N + (Y − )(Z)— or —N(Z*)— and repeating groups which can be divalent silicone moieties, divalent hydrocarbons or divalent polyethers. The copolymer can be used in personal care products, fertilizers and other agricultural products, pesticides, antifouling agents, and various waterborne coating formulations.

First claim

What is claimed is:

1. A silicon-containing linear copolymer comprising repeating units in a backbone of the copolymer and at least one zwitterionic linking group linking units in the backbone of the copolymer, the linking group having the general structures:

wherein:
Y − is an anionic radical, independently chosen from:

—(CR 1 R 2 ) b COO − ,
—(CR 3 R 4 ) c SO 3− ,
and
—(CR 5 R 6 ) d P(O)(OR 7 )O − ,
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are independently selected from hydrogen, monovalent organic radical containing 1 to 60 carbon atoms and may contain heteroatoms, the subscript b is 1 to 60, c is 3 to 60 and d is 3 to 60;
Z of formula (I) is a monovalent radical independently chosen from:
a) organic radical containing 1 to 200 carbon atoms and may contain heteroatoms,
b) hydrogen, and
c) an organosilicone radical given by—
M e M A f M S g M D h D i D D j T k T D l Q o   (III)

wherein
M=R 8 R 9 R 10 SiO 1/2 ,
M A =R 11 R 12 R 13 SiR 14 ,
M S =R 15 p (R 16 O) q SiR 17 ,
M D =R 18 R 19 R 20 SiO 1/2 ,
D=R 21 R 22 SiO 2/2 ,
D D =R 23 R 24 SiO 2/2 ,
T=R 25 SiO 3/2 ,
T D =R 26 SiO 3/2 and
Q=SiO 4/2 ;
where
R 8 , R 9 , R 10 , R 18 , R 19 , R 21 , R 22 , R 23 , R 24 and R 25 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 60 carbon atoms, may optionally contain heteroatoms;
R 11 , R 12 , R 13 , R 15 and R 16 are independently selected from the group of monovalent hydrocarbon radicals having 1-20 carbons;
R 14 , R 17 , R 20 and R 26 are linear or branched divalent radicals containing 1 to 60 carbon atoms and may contain heteroatoms;
the subscript f is 0 or 1 subject to the limitation if h is 1 then e+g+i+j+k+l+o=0,
the subscripts e, g, h, i, j, k, and l are zero or positive and have values ranging from about 0 to 10,
the subscripts p and q are zero or positive subject to the limitation that if g is positive p+q=3;
Z* of formula (II) is a monovalent zwitterionic group with the general structure
—XN + (R 27 R 28 )Y − ,

wherein
X is a divalent organic radical with 2 to 20 carbon atoms and optionally containing heteroatoms,
R 27 and R 28 are monovalent radicals with 1 to 20 carbon atoms and optionally having heteroatoms.

2. The copolymer of claim 1 wherein the repeating units comprise a silicone moiety with the general structure:
R 29 {Si(R 30 R 31 )O} a SiR 32 R 33 R 34 ;
wherein:
R 29 and R 34 are divalent branched or linear organic radicals containing 1 to 60 carbon atoms and may contain heteroatoms;
R 30 , R 31 , R 32 and R 33 are monovalent organic radicals containing 1 to 200 C atom and may contain heteroatoms and a is a positive number ranging from 1 to 500.

3. The copolymer of claim 1 wherein the repeating units comprise a divalent hydrocarbon radical containing linear, branched or cyclic alkyl, aryl, aralkyl hydrocarbon radical of 1 to 200 carbons.

4. The copolymer of claim 1 wherein the repeating units comprise a divalent polyether having the formula:
R 35 O(C 2 H 4 O) w (C 3 H 6 O) x (C 4 H 8 O) y R 36
where
R 35 and R 36 are independently a divalent hydrocarbon radical containing one or more heteroatoms and having from 2 to 20 carbon atoms,
the subscript w is zero or positive and has a value ranging from 0 to about 200,
the subscript x is zero or positive and has a value ranging from 0 to about 200 and
the subscript y is zero or positive and has a value ranging from 0 to about 200 such that (w+x+y)>0.

5. The copolymer of claim 1 wherein the Z group comprises a silicone moiety with the structure:
M e M A f M S g M D h D i D D j T k T D l Q o
with
M=R 8 R 9 R 10 SiO 1/2 ,
M A =R 11 R 12 R 13 SiR 14 ,
M S =R 15 p (R 16 O) q SiR 17 ,
M D =R 18 R 19 R 20 SiO 1/2 ,
D=R 21 R 22 SiO 2/2 ,
D D =R 23 R 24 SiO 2/2 ,
T=R 25 SiO 3/2 ,
T D =R 26 SiO 3/2 and
Q=SiO 4/2 ;
where
R 8 , R 9 , R 10 , R 18 , R 19 , R 21 , R 22 , R 23 , R 24 and R 25 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 60 carbon atoms, may optionally contain heteroatoms;
R 11 , R 12 , R 13 , R 15 and R 16 are independently selected from the group of monovalent hydrocarbon radicals having 1-20 carbons; R 14 , R 17 , R 20 and R 26 are linear or branched divalent radicals containing 1 to 60 carbon atoms and may contain heteroatoms;

the subscript f is 0 or 1 subject to the limitation if h is 1 then e+g+i+j+k+l+o=0;
the subscripts e, g, h, i, j, k, and l are zero or positive and have values ranging from about 0 to 10;
the subscripts p and q are zero or positive subject to the limitation that if g is positive p+q=3.

6. The copolymer of claim 1 wherein the groups R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 15 , R 16 , R 18 , R 19 , R 21 , R 22 , R 23 , R 24 , R 25 , R 30 , R 31 , R 32 and R 33 are independently selected from methyl, ethyl, propyl, isopropyl, phenyl and fluoro-containing hydrocarbons.

7. The copolymer of claim 1 comprising the structure:

where: a+c is greater than 1, a is greater than or equal to 0, b is greater than or equal to 0, n is 3 to 6, d is 0 to about 500 and X is greater than 1.

8. The copolymer of claim 1 comprising the structure:

where: a is 0 to about 100, b is 0 to about 100, c is 0 to about 500, X is greater than or equal to zero and Y is greater than equal to zero such that X+Y is greater than one,
R′ is independently selected from the group consisting of an alkyl radical with 1 to 20 carbon atoms which may contain heteroatoms, —R″Si(OSiR 3 ) 3 , —R″Si(OSiR 3 ) 2 R, —R″Si(OSiR 3 )R 2 , —R″Si(OR) 3 , —R″Si(OR) 2 R and —R″Si(OR)R 2 , wherein R is a monovalent hydrocarbon radical with 1 to 20 carbon atoms and optionally having hetero atoms, and R″ is a divalent hydrocarbon radical with 2 to 20 carbon atoms, optionally with heteroatoms, with the proviso that if Y is zero then at least one of R′ is a silicon containing group.

9. The copolymer of claim 1 comprising a random copolymer of the following general structure:

where: a is 0 to about 100, b is 0 to about 100, c is 0 to about 500, X is greater than or equal to zero and Y is greater than zero,

R′ is independently selected from hydrogen, an alkyl radical with 1 to 20 carbon atoms and a polyether-containing radical with the structure
—R″O(C 2 H 4 O) u (C 3 H 6 O) v (C 4 H 8 O) w Z

wherein: R″ is a divalent hydrocarbon radical with 2 to 20 carbon atoms, optionally with heteroatoms; u+v+w is 1 to about 200 and Z is hydrogen or a monovalent radical with 1 to 10 carbon atoms and may contain heteroatoms.

10. A composition comprising a silicon-containing linear copolymer and at least one active agent
wherein the linear copolymer comprises repeating units in a backbone of the copolymer and at least one zwitterionic linking group linking units in the backbone of the copolymer, the linking group having the general structures:

wherein:
Y − is an anionic radical, independently chosen from:

Assignees

• Momentive Performance Mat Inc

Inventors

• Phukan Monjit
• Saxena Anubhav
• Kodagahally Ravikumar
• Leatherman Mark

Classifications

• A61K8/898

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

• C08G77/452

  containing nitrogen-containing sequences · CPC title

• C08L83/10

  Block- or graft-copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00) · CPC title

• C08L83/12

  containing polyether sequences · CPC title

• C08G77/46

  containing polyether sequences · CPC title