Phosphorus-containing polymer, article, and processes for producing the same

Patent metadata

Field	Value
Publication number	US-9453112-B2
Application number	US-201414292144-A
Country	US
Kind code	B2
Filing date	May 30, 2014
Priority date	Jun 4, 2013
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

Abstract

A phosphorus-containing polymer comprises a plurality of phosphorus atoms, wherein about 75% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties. An article comprises a textile material having at least one surface and a phosphorus-containing polymer disposed on a least a portion of the surface, wherein the phosphorus-containing polymer comprises a plurality of phosphorus atoms, and wherein about 75% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties.

First claim

What is claimed is:

1. A phosphorus-containing polymer comprising a plurality of phosphorus atoms, wherein about 75% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties conforming to a structure selected from the group consisting of Formula (X), Formula (XI), and Formula (XII)

wherein, in each structure, R 1 is independently selected from the group consisting of hydrogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, and C 2 -C 3 haloalkenyl; T 1 and T 2 are independently selected from the group consisting of a hydroxy group and univalent moieties comprising at least one nitrogen atom; and L is a polyvalent linking group comprising at least one nitrogen atom.

2. The phosphorus-containing polymer of claim 1 , wherein about 80% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties conforming to the structure of Formula (X).

3. The phosphorus-containing polymer of claim 2 , wherein about 85% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties conforming to the structure of Formula (X).

4. The phosphorus-containing polymer of claim 1 , wherein the remaining phosphorus atoms in the phosphorus-containing polymer are present in moieties selected from the group consisting of phosphine moieties and phosphonium moieties.

5. The phosphorus-containing polymer of claim 1 , wherein R 1 is hydrogen.

6. The phosphorus-containing polymer of claim 1 , wherein L is a polyvalent linking group produced by a reaction with a compound selected from the group consisting of ammonia, urea, alkylene urea compounds, melamine, guanidine, guanidine derivatives, dicyandiamide, and mixtures thereof.

7. A process for producing a phosphorus-containing polymer, the process comprising the steps of:
(a) providing a phosphonium compound comprising at least one phosphonium moiety, the phosphonium moiety conforming to the structure of Formula (I)

wherein R 1 is selected from the group consisting of hydrogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, and C 2 -C 3 haloalkenyl;
(b) providing a nitrogen-containing cross-linking compound, the nitrogen-containing cross-linking compound comprising two or more nitrogen-hydrogen bonds;
(c) reacting the phosphorus-containing compound and the nitrogen-containing cross-linking compound in a condensation reaction to produce a first intermediate polymer;
(d) exposing the first intermediate polymer to a Brønsted base under conditions sufficient to convert at least a portion of the phosphonium moieties to phosphine moieties thereby producing a second intermediate polymer;
(e) oxidizing the second intermediate polymer by exposing the second intermediate polymer to a suitable oxidizing agent under conditions sufficient to oxidize at least a portion of the phosphorus atoms in the polymer to a pentavalent state thereby producing a phosphorus-containing polymer; and
(f) exposing the phosphorus-containing intermediate polymer to a Brønsted base to neutralize at least a portion of acid generated by the preceding oxidation step.

8. The process of claim 7 , wherein about 75% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties conforming to a structure selected from the group consisting of Formula (X), Formula (XI), and Formula (XII)

wherein, in each structure, R 1 is independently selected from the group consisting of hydrogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, and C 2 -C 3 haloalkenyl; T 1 and T 2 are independently selected from the group consisting of a hydroxy group and univalent moieties comprising at least one nitrogen atom; and L is a polyvalent linking group comprising at least one nitrogen atom.

9. The process of claim 8 , wherein about 80% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties conforming to a structure selected from the group consisting of Formula (X), Formula (XI), and Formula (XII).

10. The process of claim 9 , wherein about 85% or more of the phosphorus atoms in the polymer are present in phosphine oxide moieties conforming to a structure selected from the group consisting of Formula (X), Formula (XI), and Formula (XII).

11. The process of claim 7 , wherein the remaining phosphorus atoms in the phosphorus-containing polymer are present in moieties selected from the group consisting of phosphine moieties and phosphonium moieties.

12. The process of claim 7 , wherein R 1 is hydrogen.

13. The process of claim 7 , wherein the nitrogen-containing cross-linking compound is selected from the group consisting of ammonia, urea, alkylene urea compounds, melamine, guanidine, guanidine derivatives, dicyandiamide, and mixtures thereof.

14. An article comprising a textile material having at least one surface and a phosphorus-containing polymer disposed on a least a portion of the surface, wherein the phosphorus-containing polymer comprises a plurality of phosphorus atoms, and wherein about 75% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties conforming to a structure selected from the group consisting of Formula (X), Formula (XI), and Formula (XII)

wherein, in each structure, R 1 is independently selected from the group consisting of hydrogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, and C 2 -C 3 haloalkenyl; T 1 and T 2 are independently selected from the group consisting of a hydroxy group and univalent moieties comprising at least one nitrogen atom; and L is a polyvalent linking group comprising at least one nitrogen atom.

15. The article of claim 14 , wherein the textile material is a fabric selected from the group consisting of woven fabrics and knit fabrics.

16. The article of claim 14 , wherein the textile material comprises cellulosic fibers.

17. The article of claim 14 , wherein about 80% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties conforming to a structure selected from the group consisting of Formula (X), Formula (XI), and Formula (XII).

18. The article of claim 17 , wherein about 85% or more of the phosphorus atoms in the phosphorus-containing polymer are present in phosphine oxide moieties conforming to a structure selected from the group consisting of Formula (X), Formula (XI), and Formula (XII).

19. The article of claim 14 , wherein R 1 is hydrogen.

20. The article of claim 14 , wherein L is a polyvalent linking group produced by a reaction with a compound selected from the group consisting of ammonia, urea, alkylene urea compounds, melamine, guanidine, guanidine derivatives, dicyandiamide, and mixtures thereof.

21. The article of claim 14 , wherein the remaining phosphorus atoms in the phosphorus-containing polymer are present in moieties selected from the group consisting of phosphine moieties and phosphonium moieties.

22. A process for producing an article,

Assignees

• Milliken & Co

Inventors

• Gerhardt Warren W
• Spruell Jason M
• Mcbride Daniel T
• Valenta Petr
• Mondal Rajib
• Lucas Stephen D

Classifications

• C08G79/04 Primary

  Phosphorus linked to oxygen or to oxygen and carbon · CPC title

• B05D3/02

  by baking {(B05D3/04 takes precedence)} · CPC title

• C09K3/00

  Materials not provided for elsewhere · CPC title

• Y10T442/277

  Coated or impregnated cellulosic fiber fabric · CPC title

• C09K21/14

  Macromolecular materials · CPC title