Polydiorganosiloxane polyoxamide copolymers

Patent metadata

Field	Value
Publication number	US-9434821-B2
Application number	US-201514933543-A
Country	US
Kind code	B2
Filing date	Nov 5, 2015
Priority date	Dec 23, 2005
Publication date	Sep 6, 2016
Grant date	Sep 6, 2016

Abstract

Polydiorganosiloxane polyoxamide, linear, block copolymers and methods of making the copolymers are provided. The method of making the copolymers involves reacting a diamine with a precursor having at least one polydiorganosiloxane segment and at least two oxalyamino groups. The polydiorganosiloxane polyoxamide block copolymers are of the (AB) n type.

First claim

The invention claimed is:

1. A compound of Formula II:

wherein
each R 1 is independently an alkyl, haloalkyl, aralkyl, alkenyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;
each R 2 is independently a phenyl or a phenyl substituted with an alkyl having 1 to 4 carbon atoms, with an alkoxy having 1 to 4 carbon atoms, with a halo, or with an alkoxycarbonyl having 2 to 5 carbon atoms;
each Y is independently an alkylene, aralkylene, or a combination thereof;
each n is independently an integer of 0 to 1500; and
p is an integer of 1 to 10.

2. The compound of claim 1 , wherein R 1 is methyl.

3. The compound of claim 1 , wherein at least 50 percent of the R 1 groups are methyl.

4. The compound of claim 1 , wherein each Y is an alkylene having 1 to 10 carbon atoms, phenylene bonded to an alkylene having 1 to 10 carbon atoms, or phenylene bonded to a first alkylene having 1 to 10 carbon atoms and to a second alkylene having 1 to 10 carbon atoms.

5. The compound of claim 1 , wherein n is an integer of 0 to 500.

6. The compound of claim 1 , wherein p is an integer of 1 to 4.

7. A composition comprising:
a) at least one first compound of Formula IIa; and

b) at least one second compound of Formula II

wherein
Formula IIa is the compound of Formula II wherein p=1, and wherein
each R 1 is independently an alkyl, haloalkyl, aralkyl, alkenyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;
each R 2 is independently an alkyl, haloalkyl, aryl, or aryl substituted with an alkyl, alkoxy, halo, or alkoxycarbonyl;
each Y is independently an alkylene, aralkylene, or a combination thereof;
each n is independently an integer of 0 to 1500; and
p is an integer of 2 to 10.

8. The composition of claim 7 , wherein R 1 is methyl.

9. The composition of claim 7 , wherein each R 2 is an alkyl having 1 to 4 carbon atoms or a haloalkyl having 1 to 4 carbon atoms, the alkyl or haloalkyl having a primary carbon atom or secondary carbon atom bonded to the adjacent oxy group.

10. The composition of claim 7 , wherein each R 2 is a phenyl or a phenyl substituted with an alkyl having 1 to 4 carbon atoms, with an alkoxy having 1 to 4 carbon atoms, with a halo, or with an alkoxycarbonyl having 2 to 5 carbon atoms.

11. The composition of claim 7 , wherein each Y is an alkylene having 1 to 10 carbon atoms, phenylene bonded to an alkylene having 1 to 10 carbon atoms, or phenylene bonded to a first alkylene having 1 to 10 carbon atoms and to a second alkylene having 1 to 10 carbon atoms.

12. The composition of claim 7 , wherein the composition comprises at least 50 weight percent of the first compound of Formula II and no greater than 50 weight percent of the second compound of Formula III based on the sum of the weight of the first and second compounds in the mixture.

13. A method of making a composition comprising:
a) at least one first compound of Formula IIa, and

b) at least one second compound of Formula II

the method comprising mixing a polydiorganosiloxane diamine of Formula III

with a molar excess of an oxalate of Formula IV,

wherein
Formula IIa is the compound of Formula II wherein p=1, and wherein
each R 1 is independently an alkyl, haloalkyl, aralkyl, alkenyl, awl, or aryl substituted with an alkyl, alkoxy, or halo;
each R 2 is independently an alkyl, haloalkyl, awl, or aryl substituted with an alkyl, alkoxy, halo, or alkoxycarbonyl;
each Y is independently an alkylene, aralkylene, or a combination thereof;
each n is independently an integer of 0 to 1500; and
p is an integer of 2 to 10.

14. The method of claim 13 , wherein each R 2 is an alkyl having 1 to 4 carbon atoms or a haloalkyl having 1 to 4 carbon atoms, the alkyl or haloalkyl having a primary carbon atom or secondary carbon atom bonded to the adjacent oxy group.

15. The method of claim 13 , wherein each R 2 is a phenyl or a phenyl substituted with an alkyl having 1 to 4 carbon atoms, with an alkoxy having 1 to 4 carbon atoms, with a halo, or with an alkoxycarbonyl having 2 to 5 carbon atoms.

16. The method of claim 13 , further comprising removing the excess oxalate after reaction of the polydiorganosiloxane diamine and the oxalate.

17. The method of claim 13 , wherein the two R 2 groups of the oxalate of Formula IV are different.

18. The method of claim 13 , wherein R 1 is methyl.

Assignees

• 3M Innovative Properties Co

Inventors

• Leir Charles M
• Benson Karl E
• Hansen Richard G
• Purgett Mark D
• Everaerts Albert I

Classifications

• C08G77/54

  Nitrogen-containing linkages · CPC title

• Y10S526/935

  Hot melt adhesive · CPC title

• C23C14/12

  Organic material · CPC title

• C08G77/388

  containing nitrogen · CPC title

• C08G69/00

  Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule (products obtained from isocyanates or isothiocyanates C08G18/00; polyamide-imides C08G73/14) · CPC title