Fluorochemical piperazine carboxamides

Patent metadata

Field	Value
Publication number	US-10947348-B2
Application number	US-201716099200-A
Country	US
Kind code	B2
Filing date	Jun 9, 2017
Priority date	Jun 27, 2016
Publication date	Mar 16, 2021
Grant date	Mar 16, 2021

Abstract

The disclosure provides partially fluorinated piperazine carboxamide compounds having terminal fluoroaliphatic groups and polysiloxane groups. This invention also relates to polymer compositions comprising the fluorochemical composition and shaped articles made from the thermoplastic composition. See Formula (I).

First claim

What is claimed is:

1. A fluorochemical compound of the formula:

where
R f is a perfluorinated group; and
R Sil is a polysiloxane group;
subscript x is at least one.

2. The fluorochemical compound of claim 1 wherein R f is a perfluorinated group of having an average of 3 to 5 carbon atoms.

3. The fluorinated compound of claim 1 wherein R f is of the formula C a F 2a+1 —, where a is at least one.

4. The fluorochemical compound of claim 1 wherein R f contains at least 95% linear C 3 -C 5 groups.

5. The fluorochemical compound of claim 1 wherein R Sil is represented by the formula:

wherein
each R 6 is independently an alkyl or aryl;
a is 1 to 2000;
b is equal to zero or a positive integer;
a+b is at least one;
R 7 is alkyl, aryl or R 10 ˜,
R 10 is a (hetero)hydrocarbyl group;
with the proviso that there is at least one R 10 ˜.

6. The fluorochemical compound of claim 1 wherein subscript x is 1-6.

7. The fluorochemical compound of claim 1 prepared by the reaction of a perfluoroalkylsulfonylpiperazine with an oxalate adduct of an amino silicone.

8. The fluorochemical compound of claim 1 prepared the reaction of a perfluoroalkylsulfonylpiperazine with an oxalate to yield the mono-piperazine product, followed by reaction with an amine-functional silicone.

9. The fluorochemical compound of claim 1 derived from an aminosilicone of the formula:

wherein
each R 6 is independently an alkyl or aryl;
R NH2 is an amine-substituted (hetero)hydrocarbyl group;
a is 1 to 2000; preferably 3 to 100;
b is equal to zero or a positive integer;
a+b is at least one;
R 7 is alkyl, aryl or R NH2
wherein amine-functional silicone has at least one R NH2 group.

10. A composition comprising a thermoplastic polymer and an additive a fluorochemical compound of claim 1 .

11. The composition of claim 10 wherein the thermoplastic polymer is selected from the group consisting of polyamides, polyesters, polyurethanes, epoxides, epoxy resins, (meth)acrylates, polystyrenes, silicones and polyolefins.

12. The composition of claim 10 wherein the fluorochemical compound is present at from 0.1 to 5 weight percent of said composition.

13. A shaped article comprising the composition of claim 1 .

14. The shaped article of claim 13 selected from the group of films, sheets, fibers, woven and nonwoven fabrics.

15. The fluorochemical compound of claim 1 wherein R Sil is represented by the formula:

wherein
each R 6 is independently an alkyl or aryl;
a is 3 to 100;
b is equal to zero or a positive integer;
a+b is at least one;
R 7 is alkyl, aryl or R 10 ˜,
R 10 is a (hetero)hydrocarbyl group;
with the proviso that there is at least one R 10 ˜.

16. The fluorochemical compound of claim 1 derived from an aminosilicone of the formula:

wherein
each R 6 is independently an alkyl or aryl;
R NH2 is an amine-substituted (hetero)hydrocarbyl group;
a is 3 to 100;
b is equal to zero or a positive integer;
a+b is at least one;
R 7 is alkyl, aryl or R NH2
wherein amine-functional silicone has at least one R NH2 group.

Assignees

• 3M Innovative Properties Co

Inventors

• Teverovskiy Georgiy
• Jariwala Chetan P
• Hays David S
• Appeaning Maria A
• Boulos Marie A

Classifications

• C08G77/385 Primary

  containing halogens · CPC title

• C08G77/388 Primary

  containing nitrogen · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title