IP Library Granted Patent US 9,290,598
Granted Patent B2
US 9,290,598 · App. 13/749,291 · Granted Mar 22, 2016

Dioxaborinane co-polymers and uses thereof

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Quick Facts
Patent No.
US 9,290,598
App. No.
13/749,291
Granted
Mar 22, 2016
Kind
B2
Abstract

A co-polymer includes a polymerization product of: a first monomer: and a second monomer represented by (R 1 O)(R 2 O)B-L-X 1 —PG 2 where: L is absent, or is alkylenyl, alkenylenyl, or arylene, wherein the alkylenyl and alkenylenyl are optionally interrupted with one or more oxygen or sulfur atoms; X 1 is absent, or is amino, oxo, thio, or phosphino; PG 2 is a polymerizable group; R 1 and R 2 are independently H, alkyl, alkenyl, aryl, C(O)R 3 , C(O)OR 3 , C(O)NHR 3 , or R 1 and R 2 together with the oxygen atoms to which they are bonded join to form a 5- or 6-membered ring; and R 3 is H, alkyl, alkenyl, or aryl, wherein the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms.

Claims (36)

1. A co-polymer comprising a polymerization product of:

a first monomer: and

a second monomer represented by Formula I:

wherein:

L is absent, or is alkylenyl, alkenylenyl, or arylene, wherein the alkylenyl and alkenylenyl are optionally interrupted with one or more oxygen or sulfur atoms;

X 1 is absent, or is amino, oxo, thio, or phosphino;

PG 2 is a polymerizable group;

R 1 and R 2 are independently H, alkyl, alkenyl, aryl, C(O)R 3 , C(O)OR 3 , or C(O)NHR 3 , or R 1 and R 2 together with the oxygen atoms to which they are bonded join to form a 5- or 6-membered ring; and

R 3 is H, alkyl, alkenyl, or aryl, wherein the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms;

with the proviso that if L and X 1 are both absent, and R 1 and R 2 form a 5- or 6-membered ring, then PG 2 is not a vinyl group.

2. The co-polymer of claim 1 , comprising between 0.1% and 25% of the polymerization product of the second monomer.

3. The co-polymer of claim 1 , wherein PG 2 is acrylyl, methacrylyl, epoxyl, isocycanyl, styrenyl, vinyl, oxyvinyl, thiovinyl, ketovinyl, ketoalkyl, ketoalkoxy, ketoaryl, or cycloalkenyl.

4. The co-polymer of claim 1 , wherein PG 2 is C(O)C(R 5 )═CH 2 , C(O)CH═CH 2 , O—CH═CH 2 , S—CH═CH 2 , N═C═O,

and R 5 is a C 1 -C 8 alkyl.

5. The co-polymer of claim 4 , wherein PG 2 is C(O)C(R 5 )═CH 2 and R 5 is H; C 1 -C 8 alkyl, aryl, or CN.

6. The co-polymer of claim 1 , wherein PG 2 is C(O)CH═CH 2 .

7. The co-polymer of claim 1 , wherein X 1 is NH, O, or S.

8. The co-polymer of claim 1 , wherein L is C 1 -C 10 alkylene or arylene.

9. The co-polymer of claim 1 , wherein L is:

10. The co-polymer of claim 1 , wherein R 1 is H and R 2 is H.

11. The co-polymer of claim 1 , wherein R 1 is C 1 -C 6 alkyl and R 2 is C 1 -C 6 alkyl.

12. The co-polymer of claim 1 , wherein R 1 and R 2 together with the oxygen atoms to which they are bonded join to form a group of formula:

13. The co-polymer of claim 1 , wherein the first monomer comprises a polymerizable group, PG 1 , which is configured to polymerize with PG 2 .

14. The co-polymer of claim 13 , wherein PG 1 is acrylyl, methacrylyl, epoxyl, isocycanyl, styrenyl, vinyl, oxyvinyl, thiovinyl, ketovinyl, ketoalkyl, ketoalkoxy, ketoaryl, or cycloalkenyl.

15. The co-polymer of claim 1 , wherein the first monomer is an acrylate or a methacrylate.

16. The co-polymer of claim 15 , wherein the first monomer is represented as a group of Formula VI:

wherein:

R 7 is H; C 1 -C 22 alkyl; aryl; or a metal ion; and

R 8 is H; CN; CF 3 ; CH 3 ; or phenyl.

17. The co-polymer of claim 1 represented by Formula II:

wherein:

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

R 6 is an alkylene or arylene group; and

n and n′ represent the repeat units of the co-polymer.

18. An article comprising the co-polymer of claim 1 , wherein the article bends with a diameter of at least 1.8 inches (4.8 cm) upon conical mandrel testing.

19. An article comprising the co-polymer of claim 1 , wherein the length of the article stretches by at least 5% upon tensiometer testing.

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 Jan 24, 2013
From: PHELAN, GREGORY DAVID; CARLSON, WILLIAM BRENDEN
To: SEATTLE POLYMER COMPANY
Reel/Frame 029689/0495 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2013
From: SEATTLE POLYMER COMPANY
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 029689/0518 →