Flame retardant block copolymers from renewable feeds

Patent metadata

Field	Value
Publication number	US-9346922-B2
Application number	US-201314090022-A
Country	US
Kind code	B2
Filing date	Nov 26, 2013
Priority date	Nov 26, 2013
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

A flame retardant block copolymer is prepared from renewable content. In an exemplary synthetic method, a bio-derived flame retardant block copolymer is prepared by a ring opening polymerization of a biobased cyclic ester and a phosphorus-containing polymer. In some embodiments, the biobased cyclic ester is lactide. In some embodiments, the phosphorus-containing polymer is a hydroxyl-telechelic flame retardant biopolymer prepared by a polycondensation reaction of a biobased diol (e.g., isosorbide) and a phosphorus-containing monomer (e.g., phenylphosphonic dichloride). In other embodiments, the phosphorus-containing polymer is synthesized from a dioxaphospholane monomer.

First claim

What is claimed is:

1. A method of making a flame retardant block copolymer, comprising the steps of:
providing a biobased cyclic ester and a phosphorus-containing polymer;
preparing a ring opening polymerization reaction product of the phosphorus-containing polymer and the biobased cyclic ester.

2. The method as recited in claim 1 , wherein the phosphorus-containing polymer comprises a hydroxyl-telechelic flame retardant biopolymer prepared by a polycondensation reaction of a biobased diol and a phosphorus-containing monomer, wherein at least 50% of the mass of the biobased diol is obtained directly from a biological product.

3. The method as recited in claim 2 , wherein the hydroxyl-telechelic flame retardant biopolymer is a cyclic phosphonate.

4. The method as recited in claim 3 , wherein the cyclic phosphonate is represented by the following formula:

5. The method as recited in claim 1 , wherein the biobased cyclic ester comprises lactide.

6. The method as recited in claim 1 , wherein the biobased cyclic ester comprises lactide, wherein the phosphorus-containing polymer comprises a hydroxyl-telechelic flame retardant biopolymer, and the ring opening polymerization reaction product is represented by the following formula:

7. The method as recited in claim 1 , wherein the phosphorus-containing polymer comprises a polyphosphoester synthesized from a ring opening polymerization of a dioxaphospholane initiated from a diol.

8. The method as recited in claim 3 , wherein the cyclic phosphonate is represented by the following formula:

9. The method as recited in claim 1 , wherein the biobased cyclic ester comprises lactide, wherein the phosphorus-containing polymer comprises a hydroxyl-telechelic flame retardant biopolymer, and the ring opening polymerization reaction product is represented by the following formula:

10. The method as recited in claim 7 , wherein the polyphosphoester is represented by the following formula:

11. The method as recited in claim 1 , wherein the biobased cyclic ester comprises lactide, wherein the phosphorus-containing polymer comprises a hydroxyl-telechelic flame retardant biopolymer, and the ring opening polymerization reaction product is represented by the following formula:

12. A method of making a flame retardant block copolymer, comprising the steps of:
providing a biobased cyclic ester and a phosphorus-containing polymer, wherein the biobased cyclic ester is selected from a group consisting of lactide, glycolide, and combinations thereof, wherein the phosphorus-containing polymer comprises a hydroxyl-telechelic flame retardant biopolymer prepared by a polycondensation reaction of a biobased diol and a phosphorus-containing monomer, wherein the biobased diol is selected from a group consisting of 1,4:3,6-dianhydrohexitols (DAHs), 2,5-bis(hydroxymethyl)furan, ethylene glycol, propylene glycol, 1,3-propanediol, glycerol, 2,3-butanediol, and combinations thereof, and wherein the phosphorus-containing monomer is selected from a group consisting of phenylphosphonic dichloride, ethylphosphonic dichloride, methylphosphonic dichloride, methylenebis(phosphonic dichloride), phenyl dichlorophosphate (PDCP), ethyl dichlorophosphate, methyl dichlorophosphate, and combinations thereof;
preparing a ring opening polymerization reaction product of the phosphorus-containing polymer and the biobased cyclic ester.

13. A method of making a flame retardant block copolymer, comprising the steps of:
providing a biobased cyclic ester and a phosphorus-containing polymer, wherein the biobased cyclic ester is selected from a group consisting of lactide, glycolide, and combinations thereof, wherein the phosphorus-containing polymer comprises a polyphosphoester synthesized from a ring opening polymerization of a dioxaphospholane initiated from a diol, wherein the dioxaphospholane is selected from a group consisting of 2-ethoxy-2-oxy-1,3,2-dioxaphospholane, 2-methyl-2-oxy-1,3,2-dioxaphospholane, 2-ethoxy-4-methyl-2-oxy-1,3,2-dioxaphospholane, and combinations thereof;
preparing a ring opening polymerization reaction product of the phosphorus-containing polymer and the biobased cyclic ester.

Assignees

• IBM

Inventors

• Boday Dylan J
• Kuczynski Joseph
• Mauldin Timothy C

Classifications

• C08K3/00

  Use of inorganic substances as compounding ingredients · CPC title

• C08K5/00

  Use of organic ingredients · CPC title

• C08K7/00

  Use of ingredients characterised by shape · CPC title

• C08G79/04 Primary

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

• H01R13/527

  Flameproof cases (H01R13/70 takes precedence) · CPC title