IP Library Granted Patent US 11,111,334
Granted Patent B1
US 11,111,334 · App. 16/925,130 · Granted Sep 7, 2021

Polymerizable compositions comprising nitro substituted polyester diols

Inventors: Cody James Higginson (Fremont, CA); Katrina Marie Knauer (Redwood City, CA); Jennifer Le Roy (Sunnyvale, CA); Russell Clayton Pratt (San Mateo, CA); David Samuel Pilsk (San Jose, CA)
Assignee: BioCellection Inc.
C08G63/6856B33Y10/00B33Y70/00C08G18/463C08G63/78C08G63/916C08L67/07C08L2312/06
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Quick Facts
Patent No.
US 11,111,334
App. No.
16/925,130
Granted
Sep 7, 2021
Kind
B1
Abstract

This invention relates to the field of polymers. More specifically, the invention comprises photopolymerizable polyesters and polyester urethane oligomers comprising nitro-substituted dicarboxylic acids that are products obtained by decomposition of polyethylene. The composition described herein are useful for 3D printing, coatings and other uses.

Claims (30)

1. A composition comprising a compound of the formula:

wherein n is 0-14, y is 1-100, X is either H or NO 2 , R is an aliphatic, cycloaliphatic, aromatic, or oligoether linker, and R′ is H or a photopolymerizable group, wherein at least one X is NO 2 ; and further comprising a compound of the formula:

wherein n is 0-14, y is 1-100, R is an aliphatic, cycloaliphatic, aromatic, or oligoether linker, and R′ is H or a photopolymerizable group.

2. The composition of claim 1 wherein R is an alkylenyl group.

3. The composition of claim 2 , wherein R is ethylenyl, propylenyl, isopropylenyl, butylenyl, pentylenyl, hexylenyl, heptylenyl, or octylenyl.

4. The composition of claim 1 , wherein R is an oligoether linker.

5. The composition of claim 1 , wherein R is alkylenyl, wherein one or more CH 2 groups are substituted by —O—.

6. The composition of claim 5 , wherein R is —(CH 2 ) o —O—(CH 2 ) o —, —CH(CH 3 )CH 2 —O—CH 2 CH(CH 3 )—, or —CH 2 —O—(CH 2 ) o —O—(CH 2 ) o —CH 2 —, wherein o is 2-8.

7. The composition of claim 1 , wherein R is arylenyl or aralkylenyl.

8. The composition of claim 1 , wherein R′ is H.

9. A composition comprising a compound of the formula:

wherein n is 0-14, y is 1-100, z is 1-100, X is either H or NO 2 , R is an aliphatic, cycloaliphatic, aromatic, or oligoether linker, Ar is an aromatic linker, and R′ is H or a photopolymerizable group, wherein at least one X is NO 2 .

10. The composition of claim 9 comprising a compound of the formula:

wherein n is 0-14, y is 1-100, z is 1-100, X is either H or NO 2 , R is an aliphatic, cycloaliphatic, aromatic, or oligoether linker, and R′ is H or a photopolymerizable group, wherein at least one X is NO 2 .

11. The composition of claim 1 , wherein R′ is a photopolymerizable group comprising an ethylenically unsaturated free radical polymerizable group.

12. The composition of claim 1 , wherein R′ is a photopolymerizable group comprising a cationically polymerizable group.

13. The composition of claim 1 , wherein R′ is a photopolymerizable group comprising an acrylate ester.

14. The composition of claim 1 , wherein R′ is a photopolymerizable group comprising a methacrylate ester.

15. The composition of claim 1 , comprising a compound of the formula:

wherein n is 0-14, y is 1-100, X is either H or NO 2 , R is an aliphatic, cycloaliphatic, aromatic, or oligoether linker, R 2 is an aliphatic, cycloaliphatic or aromatic linker, R 3 is an aliphatic, cycloaliphatic, or aromatic, or oligoether linker, and R 4 is either H or methyl, wherein at least one X is NO 2 .

16. The composition of claim 1 , wherein the composition is a radiation curable liquid further comprising one or more resins, reactive diluents, photoinitiator systems, or additives.

17. The composition of claim 16 , wherein reactive diluents comprise one or more monomers containing at least one ethylenically unsaturated radically polymerizable group.

18. The composition of claim 16 , wherein reactive diluents further comprise at least one cationically polymerizable group.

19. The composition of claim 16 , wherein photoinitiator systems comprise one or more free radical photoinitiators or cationic photoinitiators.

20. A composition comprising a cured polymer obtained by the treatment of the composition claim 1 with actinic radiation.

21. The composition of claim 20 , wherein the actinic radiation is electron beams, X-rays, UV or visible light.

22. The composition of claim 20 comprising multiple layers, obtained by depositing successive layers of the composition of claim 1 according to a predetermined pattern, and then curing the layers with actinic radiation.

23. The composition of claim 20 , wherein the composition is obtained by depositing by ink jet printing, extrusion, vat polymerization, stereolithography or digital light processing.

24. The composition of claim 23 , further comprising curing the composition by actinic radiation to give a 3D composition.

25. The composition of claim 23 , wherein the actinic radiation is electron beams, X-rays, UV, or visible light.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 9, 2021
From: HIGGINSON, CODY JAMES; KNAUER, KATRINA MARIE; LE ROY, JENNIFER; PRATT, RUSSELL CLAYTON; PILSK, DAVID SAMUEL
To: BIOCELLECTION INC.
Reel/Frame 055202/0591 →
Continuity (1)
Provisional Application 62989122 · Mar 13, 2020
Cited By (1)
US 12,365,782