IP Library Granted Patent US 9,695,278
Granted Patent B2
US 9,695,278 · App. 13/932,270 · Granted Jul 4, 2017

Polyester co-phosphonates

Inventors: Lawino Kagumba (Cambridge, MA); Marc-Andre Lebel (Boxborough, MA); Jan-Pleun Lens (Boston, MA); Youmi Jeong (Boxborough, MA)
Assignee: FRX POLYMERS, INC.
C08G63/916C08G63/6926C08L67/02D03D15/00D10B2331/04
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Quick Facts
Patent No.
US 9,695,278
App. No.
13/932,270
Granted
Jul 4, 2017
Kind
B2
Abstract

Polyester co-polyphosphonates including of phosphonates covalently incorporated with polyesters and methods for making such polyester co-polyphosphonates are described herein. The polyester co-phosphonates and compositions prepared from these compounds exhibit an excellent combination of processing characteristics, mechanical and fire resistant properties.

Claims (27)

1. A method for preparing a polyester co-phosphonate comprising:

combining at least one diol, at least one dicarboxylic acid or at least one di-ester, and at least one oligomeric phosphonate of Formula II:

wherein:

—O—Ar—O— is derived from bisphenol A, bisphenol F, 4,4′-biphenol, phenolphthalein, 4,4′-thiodiphenol, 4,4′-sulfonyldiphenol, 3,3,5-trimethylcyclohexyldiphenol, or combinations thereof;

R is a C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 5-20 cycloalkyl, or C 6-20 aryl; and

n is an integer from 2 to about 10,

to form a reaction mixture; and

reacting the reaction mixture;

wherein the phosphonate is incorporated into a polyester to form the polyester co-phosphonate.

2. The method of claim 1 , wherein the method is carried out in a batch process or a continuous process.

3. The method of claim 1 , further comprising adding at least one AB monomer into the reaction mixture.

4. The method of claim 1 , further comprising introducing a catalyst into the reaction mixture.

5. The method of claim 1 , wherein the oligomeric phosphonate comprises about 1 wt. % to about 80 wt. % of the reaction mixture.

6. The method of claim 1 , wherein the diol is selected from the group consisting of 1,4-cyclohexyldimethanol, 1,4-butane diol, 1,3-propane diol, ethylene diol, and combinations thereof.

7. The method of claim 1 , wherein the diol is ethylene glycol.

8. The method of claim 1 , wherein the diol is selected from the group consisting of 4,4′-dihydroxybiphenyl, hydroquinone, resorcinol, methyl hydroquinone, chlorohydroquinone, acetoxyhydroquinone, nitrohydroquinone, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-chlorophenyl)propane, bis(4-hydroxyphenyl)methane, bis(4-hydroxy-3,5-dimethyl phenyl)methane, bis(4-hydroxy-3,5-dichlorophenyl)methane, bis(4-hydroxy-3,5-dibromophenyl)methane, bis(4-hydroxy-3-methylphenyl)methane, bis(4-hydroxy-3-chlorophenyl)methane, 1,1-bis(4-hydroxyphenyl)cyclohexane, bis(4-hydroxyphenyl)ketone, bis(4-hydroxy-3,5-dimethylphenyl)ketone, bis(4-hydroxy-3,5-dichlorophenyl)ketone, bis(4-hydroxyphenyl) sulfide, and bis(4-hydroxyphenyl) sulfone.

9. The method of claim 1 , wherein the at least one dicarboxylic acid or at least one di-ester is selected from the group consisting of adipic acid, terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, and combinations thereof.

10. The method of claim 1 , wherein the at least one dicarboxylic acid or at least one di-ester is selected from the group consisting of dimethyl terephthalate, dimethyl isophthalate, dimethyl naphthalate, and combinations thereof.

11. The method of claim 1 , further comprising introducing one or more additives into the polyester co-phosphonate.

12. The method of claim 11 , wherein introducing the one or more additives into the polyester co-phosphonate is carried out during or after reacting.

13. The method of claim 1 , further comprising pelletizing the polyester co-phosphonate.

14. The method of claim 1 , further comprising spinning the polyester co-phosphonate into fibers.

15. The method of claim 14 , further comprising heat setting the fibers.

16. The method of claim 14 , further comprising weaving the fibers into fabric or twisting the fibers into yarn.

17. The method of claim 1 , further blending the polyester co-phosphonate and one or more engineering polymers.

18. The method of claim 17 , wherein the one or more engineering polymer comprises a polyester.

19. The method of claim 17 , further comprising spinning the blended polyester co-phosphonate and one or more engineering polymer into fibers.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 13, 2025
From: PLUTO OPCO (CAYMAN), LLC
To: DOSKOCIL MANUFACTURING COMPANY, INC.
Reel/Frame 070207/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2013
From: KAGUMBA, LAWINO; LEBEL, MARC-ANDRE; LENS, JAN-PLEUN; JEONG, YOUMI
To: FRX POLYMERS, INC.
Reel/Frame 031273/0489 →
Continuity (2)
Provisional Application 61666005 · Jun 29, 2012
Related Publication 20140000751A1 · Jan 2, 2014