Cross-linked impact modified polyphosphazenes

Patent metadata

Field	Value
Publication number	US-11059960-B2
Application number	US-201715784656-A
Country	US
Kind code	B2
Filing date	Oct 16, 2017
Priority date	Oct 16, 2017
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

A flame retardant composition and a method of making a flame retardant composition is provided. In an embodiment, the method includes reacting a phosphazene material with an acrylamide monomer material to form a functionalized phosphazene material; initiating a polymerization reaction on a reaction mixture comprising a functionalized phosphazene material and one or more monomers to form a first impact-modified phosphazene material; and reacting the first impact-modified phosphazene material with a poly(dichlorophosphazene) monomer material, and a reactant selected from the group consisting of R 1 OH, HNR 2 R 3 , or a combination thereof, to form a second impact-modified phosphazene material.

First claim

What is claimed is:

1. A method of forming an impact-modified phosphazene material comprising:
reacting a phosphazene material with an acrylamide monomer material to form a functionalized phosphazene material;
initiating a polymerization reaction on a reaction mixture comprising the functionalized phosphazene material and one or more monomers to form a first impact-modified phosphazene material; and
reacting the first impact-modified phosphazene material with a poly(dichlorophosphazene) monomer material, and a reactant selected from the group consisting of R 1 OH, HNR 2 R 3 , or a combination thereof, wherein R 1 is C 1 to C 40 unsubstituted hydrocarbyl, C 1 to C 40 substituted hydrocarbyl, unsubstituted aryl, substituted aryl, fused aryl, perfluoroalkyl, partially fluorinated alkyl, epoxy, silylcarbyl, siloxyl, anhydride, maleimide, cyanurate, or isocyanurate; and each of R 2 and R 3 is independently hydrogen, C 1 to C 40 unsubstituted hydrocarbyl, C 1 to C 40 substituted hydrocarbyl, unsubstituted aryl, substituted aryl, fused aryl, perfluoroalkyl, partially fluorinated alkyl, epoxy, silylcarbyl, siloxyl, anhydride, maleimide, cyanurate, or isocyanurate, to form a second impact-modified phosphazene material.

2. The method of claim 1 , further comprising heating a mixture comprising the second impact-modified phosphazene material to form a third impact-modified phosphazene material.

3. The method of claim 2 , wherein the second impact-modified phosphazene material is represented by formula (I)

and the third impact-modified phosphazene material is represented by formula (II),

wherein:
each of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 is independently an impact modifier material;
each of X 1 , X 2 , and X 3 is independently an —OR 1 radical or an —NR 2 R 3 radical, wherein R 1 is C 1 to C 40 unsubstituted hydrocarbyl, C 1 to C 40 substituted hydrocarbyl, unsubstituted aryl, substituted aryl, fused aryl, perfluoroalkyl, partially fluorinated alkyl, epoxy, silylcarbyl, siloxyl, anhydride, maleimide, cyanurate, or isocyanurate; and each of R 2 and R 3 is independently hydrogen, C 1 to C 40 unsubstituted hydrocarbyl, C 1 to C 40 substituted hydrocarbyl, unsubstituted aryl, substituted aryl, fused aryl, perfluoroalkyl, partially fluorinated alkyl, epoxy, silylcarbyl, siloxyl, anhydride, maleimide, cyanurate, or isocyanurate;
m is about 1-200;
n is about 1-200; and
p is about 1-100.

4. The method of claim 1 , wherein the one or more monomers are selected from the group consisting of an acrylate monomer material, acrylamide monomer material, styrenic monomer material, other vinylic monomer material, or a combination thereof.

5. The method of claim 1 , wherein the reaction mixture further comprises a phosphorous-containing monomer.

6. The method of claim 5 , wherein the phosphorous-containing monomer includes a phosphorous-containing styrenic monomer.

7. The method of claim 5 , wherein the phosphorous-containing monomer is

or combinations thereof,
wherein:
each of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently unsubstituted hydrocarbyl, substituted hydrocarbyl, unsubstituted aryl, substituted aryl, unsubstituted alkoxy, substituted alkoxy, unsubstituted aryloxy, or substituted aryloxy.

8. The method of claim 1 , wherein the first impact-modified phosphazene material is represented by the formula:

wherein:
PG is a protecting group; and
each of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 is independently an impact modifier material.

9. A method of forming an impact-modified phosphazene material comprising:
reacting a phosphazene material with an acrylamide monomer material to form a functionalized phosphazene material;
initiating a polymerization reaction on a reaction mixture comprising the functionalized phosphazene material and one or more monomers to form a first impact-modified phosphazene material, the one or more monomers selected from the group consisting of an acrylate monomer material, acrylamide monomer material, styrenic monomer material, other vinylic monomer material, or a combination thereof; and
reacting the first impact-modified phosphazene material with a poly(dichlorophosphazene) monomer material, and a reactant selected from the group consisting of R 1 OH, HNR 2 R 3 , or a combination thereof, wherein R 1 is C 1 to C 40 unsubstituted hydrocarbyl, C 1 to C 40 substituted hydrocarbyl, unsubstituted aryl, substituted aryl, fused aryl, perfluoroalkyl, partially fluorinated alkyl, epoxy, silylcarbyl, siloxyl, anhydride, maleimide, cyanurate, or isocyanurate; and each of R 2 and R 3 is independently hydrogen, C 1 to C 40 unsubstituted hydrocarbyl, C 1 to C 40 substituted hydrocarbyl, unsubstituted aryl, substituted aryl, fused aryl, perfluoroalkyl, partially fluorinated alkyl, epoxy, silylcarbyl, siloxyl, anhydride, maleimide, cyanurate, or isocyanurate, to form a second impact-modified phosphazene material.

10. The method of claim 9 , further comprising heating a mixture comprising the second impact-modified phosphazene material to form a third impact-modified phosphazene material.

11. The method of claim 10 , wherein the second impact-modified phosphazene material is represented by formula (I)

and the third impact-modified phosphazene material is represented by formula (II),

wherein:
each of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 is independently an impact modifier material;
each of X 1 , X 2 , and X 3 is independently an —OR 1 radical or an —NR 2 R 3 radical, wherein R 1 is C 1 to C 40 unsubstituted hydrocarbyl, C 1 to C 40 substituted hydrocarbyl, unsubstituted aryl, substituted aryl, fused aryl, perfluoroalkyl, partially fluorinated alkyl, epoxy, silylcarbyl, siloxyl, anhydride, maleimide, cyanurate, or isocyanurate; and each of R 2 and R 3 is independently hydrogen, C 1 to C 40 unsubstituted hydrocarbyl, C 1 to C 40 substituted hydrocarbyl, unsubstituted aryl, substituted aryl, fused aryl, perfluoroalkyl, partially fluorinated alkyl, epoxy, silylcarbyl, siloxyl, anhydride, maleimide, cyanurate, or isocyanurate;
m is about 1-200;
n is about 1-200; and
p is about 1-100.

12. The method of claim 9 , wherein the reaction mixture further comprises a phosphorous-containing monomer.

13. The method of claim 8 , wherein the first impact-modified phosphazene material is represented by the formula:

wherein:
PG is a protecting group; and
each of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 is independently an impact modifier material.

14. A method of forming an impact-modified phosphazene material comprising:
reacting a phosphazene material with an acrylamide monomer material to form a functionalized phosphazene material;
initiating a polymerization reaction on a reaction mixture comprising the functionalized phosphazene material and one or more monomers to form a first impact-modified phosphazene material, the one or more m

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Kuczynski Joseph
• Porter Jacob T
• Wertz Jason T

Classifications

• C09K21/14 Primary

  Macromolecular materials · CPC title

• C08C19/34

  reacting with oxygen or oxygen-containing groups · CPC title

• C08C19/24

  Incorporating phosphorus atoms into the molecule · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title

• C08F2438/03

  Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX] · CPC title