IP Library Granted Patent US 8,952,102
Granted Patent B2
US 8,952,102 · App. 14/297,990 · Granted Feb 10, 2015

Alkyl ether compositions and methods of use

Inventors: William B. Carlson (Seattle, WA); Gregory D. Phelan (Cortland, NY)
Assignee: Empire Technology Development LLC
C07C43/115C07C43/10C08G65/00C08L71/02C07C43/04
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Quick Facts
Patent No.
US 8,952,102
App. No.
14/297,990
Granted
Feb 10, 2015
Kind
B2
Abstract

A polymer includes a linker represented by Formula I ([OR 1 OCH 2 OR 2 OCH 2 ] m ), where R 1 and R 2 are, independently, alkylene, alkenylene, arylene, heteroarylene, or alkylarylalkylene; and the polymer has a weight average molecular weight of about 500 g/mol to about 2,000,000 g/mol, and m is 1 to 1000.

Claims (43)

1. A polymer comprising a linker represented by Formula II:

wherein:

R 1 , R 2 , and R 3 are, independently, alkylene, alkenylene, arylene, heteroarylene, or alkylarylalkylene;

R 1 and R 3 are different;

the polymer has a weight average molecular weight of about 500 g/mol to about 2,000,000 g/mol; and

m is 1 to 1000.

2. The polymer of claim 1 , wherein:

R 1 and R 3 are alkylene; and

R 2 is alkylarylalkylene.

3. The polymer of claim 1 , wherein:

R 1 and R 3 are alkylarylalkylene; and

R 2 is alkylene.

4. The polymer of claim 1 , wherein each alkylarylalkylene is a mixture of at least two of p-xylenyl, m-xylenyl, and o-xylenyl.

5. The polymer of claim 1 , wherein each alkylarylalkylene is, independently, a mixture of p-xylenyl and m-xylenyl having a p-xylenyl:m-xylenyl ratio of about 2:1 to about 20:1.

6. The polymer of claim 1 , wherein each alkylarylalkylene is, independently, a mixture of p-xylenyl and o-xylenyl having a p-xylenyl:o-xylenyl ratio of about 2:1 to about 20:1.

7. The polymer of claim 1 , wherein each alkylene is C 1 -C 10 alkylene.

8. The polymer of claim 7 , wherein each alkylene is (CH 2 ) 2 ; (CH 2 ) 4 ; (CH 2 ) 6 ; or (CH 2 ) 8 .

9. The polymer of claim 1 , wherein m is 1 to 50.

10. A polymer represented by Formula IV:

wherein:

A is hydrogen, alkyl, or —C(O)R 4 ;

R 1 and R 2 are, independently, alkylene, alkenylene, arylene, heteroarylene, or alkylarylalkylene;

R 4 is hydrogen, alkyl, or phenyl;

R 5 is hydrogen, CN, alkyl, or phenyl;

the polymer has a weight average molecular weight of about 500 g/mol to about 2,000,000 g/mol;

m is 1 to 1000; and

q is 1 to 1000.

11. The polymer of claim 10 , wherein:

R 1 is (CH 2 ) 2 ; (CH 2 ) 4 ; (CH 2 ) 6 ; or (CH 2 ) 8 ; and

R 2 is a mixture of at least two of p-xylenyl, m-xylenyl, and o-xylenyl.

12. The polymer of claim 10 , wherein m is 1 to 50.

13. The polymer of claim 10 , wherein q is 1 to 50.

14. A method of degrading a polymer, the method comprising:

providing a polymer comprising a linker represented by Formula I:

contacting the polymer with an acid; and

obtaining a composition including HOR 1 OH and HOR 2 OH;

wherein:

R 1 and R 2 are, independently, alkylene, alkenylene, arylene, heteroarylene, or alkylarylalkylene; and

m is 1 to 1000.

15. The method of claim 14 , further comprising converting the composition including HOR 1 OH and HOR 2 OH to a recycled polymer comprising the linker represented by Formula I.

16. The method of claim 14 , wherein the acid is selected from the group consisting of HCl, HBr, H 2 SO 4 , acetic acid, trifluoroacetic acid, phosphoric acid, and nitric acid.

17. The method of claim 14 , wherein the contacting further comprises contacting at a temperature of from about 20° C. to about 120° C.

18. The method of claim 14 , wherein the providing the polymer includes the linker having a value of m from about 1 to about 50, inclusive.

Assignments (4)
RELEASE OF SECURITY INTEREST IN PATENTS, RECORDED ON JANUARY 29, 2019 AT REEL 048373 FRAME 0217 Recorded Sep 22, 2025
From: CRESTLINE DIRECT FINANCE, L.P., AS COLLATERAL AGENT
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 072936/0464 →
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2015
From: CARLSON, WILLIAM BRENDEN; PHELAN, GREGORY DAVID
To: SEATTLE POLYMER COMPANY
Reel/Frame 034641/0765 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2015
From: SEATTLE POLYMER COMPANY
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 034641/0884 →
Continuity (2)
Continuation 13761512 · Feb 7, 2013
Related Publication 20140288332A1 · Sep 25, 2014