IP Library Granted Patent US 8,779,070
Granted Patent B2
US 8,779,070 · App. 13/761,512 · Granted Jul 15, 2014

Alkyl ether compositions and methods of use

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Quick Facts
Patent No.
US 8,779,070
App. No.
13/761,512
Granted
Jul 15, 2014
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 (51)

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

wherein:

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

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 is C 2 -C 10 alkylene; and

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

3. The polymer of claim 2 , wherein R 2 is a mixture of p-xylenyl and m-xylenyl having a p-xylenyl:m-xylenyl ratio of about 2:1 to about 20:1.

4. The polymer of claim 2 , wherein R 2 is a mixture of p-xylenyl and o-xylenyl having a p-xylenyl:o-xylenyl ratio of about 2:1 to about 20:1.

5. The polymer of claim 1 , wherein R 1 is (CH 2 ) 2 ; (CH 2 ) 4 ; (CH 2 ) 6 ; or (CH 2 ) 8 .

6. A polymer represented by Formula III:

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;

PG 1a is the polymerization product of a polymerization group PG 1 ;

PG 1 is selected from the group consisting of acrylyl, methacrylyl, isocycanyl, styrenyl, epoxyl, vinyl, oxetanyl, DL-lactidyl, and bicyclo[2.2.1]hept-2-enyl;

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.

7. The polymer of claim 6 , 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.

8. The polymer of claim 6 , wherein m is 1 to 50.

9. The polymer of claim 6 , wherein q is 1 to 50.

10. A method of preparing polymer represented by Formula III, the method comprising:

contacting XCH 2 OR 2 OCH 2 X with HOR 10 H, HOR 1 OA, and a base to form a polymer represented by Formula V:

contacting the polymer represented by Formula V with a compound represented by PG 1 -L and a base to form a polymer represented by Formula VI:

and

polymerizing PG 1 of the polymer represented by Formula VI to form the polymer represented by Formula III:

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;

X is a leaving group;

PG 1 is a polymerizable group selected from the group consisting of acrylyl, methacrylyl, isocycanyl, styrenyl, epoxyl, vinyl, oxetanyl, DL-lactidyl, and bicyclo[2.2.1]hept-2-enyl;

PG 1a is the polymerization product of the polymerizable group PG 1 ;

L is a leaving group;

m is 1 to 1000; and

q is 1 to 1000.

11. The method of claim 10 , wherein the polymer represented by Formula III is a polymer represented by Formula IV:

wherein:

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

12. The method of claim 10 , further comprising forming XCH 2 OR 2 OCH 2 X by contacting R 6 OCH 2 OR 2 OCH 2 OR 6 with HX, wherein R 6 is alkyl.

13. The method of claim 12 , wherein R 6 is methyl.

14. The method of claim 10 , wherein X Cl, Br, I,

and L, Cl, Br, I,

15. The method of claim 14 , wherein X and L are Cl.

16. The method of claim 10 , wherein the base is a tertiary amine, secondary amine, pyridine, or a carbonate salt.

17. The method of claim 16 , wherein the base is morpholine, N-methylmorpholine, piperidine, N-methypiperidine, piperazine, N-methylpiperazine, N,N-dimethylpiperazine, triethylamine, diisopropylethylamine, or pyridine.

Assignments (3)
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 Feb 7, 2013
From: CARLSON, WILLIAM BRENDEN; PHELAN, GREGORY DAVID
To: SEATTLE POLYMER COMPANY
Reel/Frame 029774/0939 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2013
From: SEATTLE POLYMER COMPANY
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 029775/0014 →