Unsaturated deoxybenzoin compound, polymer prepared therefrom, and articles comprising the polymer

Patent metadata

Field	Value
Publication number	US-10106630-B2
Application number	US-201715472508-A
Country	US
Kind code	B2
Filing date	Mar 29, 2017
Priority date	Apr 1, 2016
Publication date	Oct 23, 2018
Grant date	Oct 23, 2018

Abstract

An unsaturated deoxybenzoin compound has the structure (I)

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and n are defined herein. A polymer including at least one group derived from a deoxybenzoin compound having structure (I), (II), or a combination thereof

is also described, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and n are defined herein.

First claim

The invention claimed is:

1. A polymer comprising at least one group derived from a deoxybenzoin compound having structure (I), (II), or a combination thereof

wherein
R 1 and R 2 are independently at each occurrence hydrogen, a halogen, a nitrile group, a C 1-6 alkyl group, a C 2-13 alkenyl group, a C 2-13 alkynyl group, a C 6-20 aryl group, a C 7-13 arylalkyl group, or a C 7-13 alkylaryl group;
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently at each occurrence hydrogen, a halogen, a hydroxyl group, a nitrile group, a C 1-6 alkyl group, a C 2-13 alkenyl group, a C 2-13 alkynyl group, a C 1-6 alkoxy group, a C 6-20 aryl group, a C 7-13 arylalkyl group, a C 7-13 alkylaryl group, or a C 4-12 cycloalkyl group; and
n is independently at each occurrence an integer from 1 to 12.

2. The polymer of claim 1 , wherein the polymer is derived from the deoxybenzoin compound having structure (I), (II), or a combination thereof, and one or more ethylenically unsaturated monomers.

3. The polymer of claim 2 , wherein the ethylenically unsaturated monomer is a styrenic monomer, a C 1-12 alkyl (meth)acrylate monomer, a C 6-20 aryl (meth)acrylate monomer, a (meth)acrylic acid, an acrylonitrile, an alpha olefin, a vinyl ester, a vinyl alkyl ether, or a combination thereof.

4. The polymer of claim 1 , wherein the polymer is derived from a polymer having in-chain unsaturation and the deoxybenzoin compound having structure (I), (II), or a combination thereof.

5. The polymer of claim 4 , wherein the polymer having in-chain unsaturation is an unsaturated polyolefin, an unsaturated aliphatic polyester, an unsaturated elastomer, an unsaturated aliphatic polyurethane, or a combination thereof.

6. The polymer of claim 1 , wherein the polymer is derived from the deoxybenzoin compound having structure (I), (II), or a combination thereof, and a polymer having one or more unsaturated pendent groups, one or more unsaturated end-groups, or both.

7. The polymer of claim 1 , wherein each occurrence of R 1 and R 2 is hydrogen.

8. The polymer of claim 1 , wherein each occurrence of n is 1.

9. The polymer of claim 1 , wherein each occurrence of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 is hydrogen.

10. The polymer of claim 1 , wherein
the polymer comprises at least one group derived from a deoxybenzoin compound having structure (I);
each occurrence of R 1 and R 2 is hydrogen;
each occurrence of n is 1; and
each occurrence of R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is hydrogen.

11. The polymer of claim 1 , wherein
the polymer comprises at least one group derived from a deoxybenzoin compound having structure (II);
each occurrence of R 1 and R 2 is hydrogen;
each occurrence of n is 1; and
each occurrence of R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , R 9 , and R 10 is hydrogen.

12. The polymer of claim 1 , wherein the polymer exhibits one or more of the following properties:
a char yield of at least 30 percent after 60 minutes at 750° C., as determined by thermogravimetric analysis;
a heat release capacity of less than or equal to 150 joules per gram-Kelvin determined using a pyrolysis combustion flow calorimeter; and
a total heat release of less than 20 kilojoules per gram determined using a pyrolysis combustion flow calorimeter.

13. The polymer of claim 1 , wherein the polymer is at least partially crosslinked.

14. An article comprising the polymer of claim 1 .

Assignees

• Univ Massachusetts

Inventors

• Emrick Todd
• Coughlin E Bryan
• Szyndler Megan
• Mir Aabid A
• Timmons Justin C

Classifications

• C08F12/34

  Monomers containing two or more unsaturated aliphatic radicals · CPC title

• C07C49/84 Primary

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C08F112/34

  Monomers containing two or more unsaturated aliphatic radicals · CPC title

• C08F236/22

  the radical having three or more carbon-to-carbon double bonds · CPC title

• C08F36/22 Primary

  the radical having three or more carbon-to-carbon double bonds · CPC title