Aminosiloxane polymer and method of forming

Patent metadata

Field	Value
Publication number	US-10059806-B2
Application number	US-201515311653-A
Country	US
Kind code	B2
Filing date	May 20, 2015
Priority date	May 21, 2014
Publication date	Aug 28, 2018
Grant date	Aug 28, 2018

Abstract

An aminosiloxane polymer includes at least one Si-bonded functional group. This functional group has the chemical formula: —(R—NH) a R 1 —N(R 2 )—CH(—COOH)(—R 3 —C(═O)—NR 4 2 ) (I). In Formula (I), R is a C 1 -C 10 hydrocarbon group. R 1 is a C 1 -C 10 hydrocarbon group. R 2 is a hydrogen atom, a C 1 -C 12 hydrocarbon group, or a phenyl group. R 3 is a C 1 -C 4 hydrocarbon group. Each R 4 is independently a hydrogen atom, a C 1 -C 12 hydrocarbon group, a C 1 -C 12 hydroxyl-hydrocarbon group, or a phenyl group. Moreover, “a” is 0 or 1, such that (R—NH) is optional. The aminosiloxane polymer can be formed using the method of this disclosure and can be formed in, and/or included in, the emulsion of this disclosure.

First claim

What is claimed is:

1. An aminosiloxane polymer comprising at least one Si-bonded functional group having the chemical formula:
—(R—NH) a —R 1 —N(R 2 )—CH(—COOH)(—R 3 —C(═O)—NR 4 2 )  (I)

wherein R is a C 1 -C 10 hydrocarbon group; R 1 is a C 1 -C 10 hydrocarbon group; R 2 is a hydrogen atom, a C 1 -C 12 hydrocarbon group, or a phenyl group; R 3 is a C 1 -C 4 hydrocarbon group; each R 4 is independently a hydrogen atom, a C 1 -C 12 hydrocarbon group, a C 1 -C 12 hydroxyl-hydrocarbon group, or a phenyl group; and “a” is 0 or 1.

2. The aminosiloxane polymer of claim 1 that is the reaction product of:
(A) a polyorganosiloxane having an amino group; and
(B) a reaction product of; i) an alkylamine and/or alkanolamine, and ii) an alkenyl cyclic anhydride.

3. The aminosiloxane polymer of claim 2 , wherein said (A) polyorganosiloxane having the amino group has the chemical structure:

wherein each of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 is independently OH, R′(OR″) m or R′OH, where “m” is 1 to 3, and each of R′ and R″ is independently an alkyl group, a C 1 -C 12 hydrocarbon group, a C 2 -C 30 alkenyl group, a C 6 -C 12 aromatic group, or a polyalkyleneoxy group; “x” is from 1 to 3,000; “y” is from 1 to 100; and R 14 comprises the amino group.

4. The aminosiloxane polymer of claim 2 , wherein said amino group of component (A) comprises:
i) a NH 2 moiety bonded to a linear, branched, or cyclic hydrocarbon having 1 to 6 carbon atoms and said linear, branched, or cyclic hydrocarbon is bonded to a Si atom of component (A); or
ii) one or more NH 2 , NH, or NHR′, moieties, where R′ is an alkyl group.

5. The aminosiloxane polymer of claim 2 , wherein:
i) said alkylamine of component (B) comprises at least one NH moiety and at least one carbon chain having 3 to 12 carbon atoms;
ii) said alkanolamine of component (B) comprises one or two hydroxyl groups; or
iii) both i) and ii).

6. The aminosiloxane polymer of claim 1 , wherein said Si-bonded functional group has the chemical structure:

7. The aminosiloxane polymer of claim 1 , having the chemical structure:

wherein each of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 is independently OH, R′(OR″) m , or R′OH, where “m” is 1 to 3, and each of R′ and R″ is independently an alkyl group, a C 1 -C 12 hydrocarbon group, a C 2 -C 30 alkenyl group, a C 6 -C 12 aromatic group, or a polyalkyleneoxy group; “x” is from 1 to 3,000; “y” is from 1 to 100; and “A” is said Si-bonded functional group.

8. An emulsion comprising:
I) a liquid continuous phase; and
II) a dispersed phase comprising an aminosiloxane polymer comprising at least one Si-bonded functional group having the chemical formula:
—(R—NH) a —R 1 —N(R 2 )—CH(—COOH)(—R 3 —C(═O)—NR 4 2 )  (I)

wherein R is a C 1 -C 10 hydrocarbon group; R 1 is a C 1 -C 10 hydrocarbon group; R 2 is a hydrogen atom, a C 1 -C 12 hydrocarbon group, or a phenyl group; R 3 is a C 1 -C 4 hydrocarbon group; each R 4 is independently a hydrogen atom, a C 1 -C 12 hydrocarbon group, a C 1 -C 12 hydroxyl-hydrocarbon group, or a phenyl group; and “a” is 0 or 1.

9. The emulsion of claim 8 , wherein said aminosiloxane polymer of said dispersed phase:
i) is a liquid; and/or
ii) is present as particles dispersed in said continuous phase and said dispersed particles have a size of less than about 15 μm; and/or
iii) is present in said emulsion in an amount of from 10 to 90 parts by weight per 100 parts by weight of said emulsion.

10. The emulsion of claim 8 , further comprising a polydialkylsiloxane having a weight average molecular weight (M w ) of up to 1,000,000 g/mol, and wherein a ratio of said polydialkylsiloxane to said aminosiloxane polymer is from about 0.1 to 100.

11. A composition comprising the aminosiloxane polymer as set forth in claim 1 , said composition chosen from personal care compositions, cosmetic compositions, fabric treating compositions, fiber treating compositions, hair care compositions, fiber care compositions, and combinations thereof.

12. A method of forming an aminosiloxane polymer comprising at least one Si-bonded functional group, said method comprising the steps of:
providing a polyorganosiloxane having an amino group;
providing an alkylamine and/or an alkanolamine;
providing an alkenyl cyclic anhydride;
reacting i) the alkylamine and/or alkanolamine and ii) the alkenyl cyclic anhydride to form an intermediate; and
reacting the intermediate and the polyorganosiloxane having the amino group to form the aminosiloxane polymer;
the Si-bonded functional group having the chemical formula:
—(R—NH) a —R 1 —N(R 2 )—CH(—COOH)(—R 3 —C(═O)—NR 4 2 )  (I)

wherein R is a C 1 -C 10 hydrocarbon group; R 1 is a C 1 -C 10 hydrocarbon group; R 2 is a hydrogen atom, a C 1 -C 12 hydrocarbon group, or a phenyl group, R 3 is a C 1 -C 4 hydrocarbon group; each R 4 is independently a hydrogen atom, C 1 -C 12 hydrocarbon group, a C 1 -C 12 hydroxyl-hydrocarbon group, or a phenyl group; and “a” is 0 or 1.

13. The method of claim 12 , wherein the step of providing the polyorganosiloxane having the amino group is further defined as:
providing a first emulsion comprising a first continuous phase and a first dispersed phase comprising the polyorganosiloxane having the amino group;
wherein the step of reacting the intermediate and the polyorganosiloxane having the amino group is further defined as:
adding the intermediate to the first emulsion to form a second emulsion and heating the second emulsion to a temperature of about 20° C. to 80° C. to form the aminosiloxane polymer in-situ in the second emulsion; and
wherein the second emulsion comprises a second continuous phase and a second dispersed phase comprising the aminosiloxane polymer.

14. The method of claim 13 , wherein the first dispersed phase and/or the second dispersed phase further comprise a polydialkylsiloxane having a weight average molecular weight (M w ) of up to 1,000,000 g/mol and a ratio of the polydialkylsiloxane to the aminosiloxane polymer is from about 0.1 to 100.

15. The method of claim 13 , wherein:
i) the polyorganosiloxane having the amino group is present in the first dispersed phase of the first emulsion in an amount of from about 10 to 70 parts by weight per 100 parts by weight of the first emulsion; and/or
ii) the polyorganosiloxane having the amino group is present in the second dispersed phase of the second emulsion in an amount of from about 10 to 70 parts by weight per 100 parts by weight of the second emulsion; and/or
iii) the intermediate is present in the second dispersed phase of the second emulsion in an amount of from about 0.1 to 30 parts by weight per 100 parts by weight of the second emulsion.

16. The aminosiloxane polymer of claim 2 , wherein:
i) said alkylamine of component (B) comprises at least one NH moiety and at least one carbon chain having 3 to 12 carbon atoms;
ii) said alkanolamine of component (B) comprises a single NH moiety and 2 to 5 hydroxyl groups; or
iii) both i) and ii).

17. The aminosiloxane polymer of claim 6 , having the chemical structure:

Assignees

• Dow Corning
• Dow Silicones Corp

Inventors

• Feng Qian
• Ferritto Michael Salvatore
• Fryfogle Patrick J
• Johnson Bethany K
• Nguyen Kimmai Thi
• Zimmerman Brett Lee
• Zimmerman Kenneth Edward

Classifications

• C08K5/1539

  Cyclic anhydrides · CPC title

• C08L83/08 Primary

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen · CPC title

• C08G77/388

  containing nitrogen · CPC title

• C08L2203/02

  for biomedical use · CPC title

• A61K8/898

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