Monomers and polymers derived from natural phenols

• US 9,630,897 B2
• Filed: 03/11/2014
• Issued: 04/25/2017
• Est. Priority Date: 03/11/2013
• Status: Expired due to Fees

• Current Assignee: Ndsu-Research Foundation
• Original Assignee: Ndsu-Research Foundation
• Inventors: Chisholm, Bret Ja, Alam, Samim
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): Miller, David L
• Application Number:
  US14/774,628
• Publication Number:
  US 20160023980A1
• Time in Patent Office: 1,141 Days
• CPC Class Codes: C07C 43/2055 containing more than one ether bond
• CPC Class Codes: C07C 43/215 having unsaturation outside the six-membered aromatic rings
• CPC Class Codes: C07C 67/24 by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
• CPC Class Codes: C07C 69/007 Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
• CPC Class Codes: C08F 116/08 Allyl alcohol
• CPC Class Codes: C08F 116/38 by a acetal or ketal radical
• CPC Class Codes: C08F 14/14 Monomers containing three or more carbon atoms
• CPC Class Codes: C08F 16/08 Allyl alcohol
• CPC Class Codes: C08F 16/32 Monomers containing two or more unsaturated aliphatic radicals
• CPC Class Codes: C08F 16/38 by an acetal or ketal radical
• CPC Class Codes: C08F 216/085 Allyl alcohol alkoxylate
• CPC Class Codes: C08F 216/12 by an ether radical
• CPC Class Codes: C08F 216/125 Monomers containing two or more unsaturated aliphatic radicals, e.g. trimethylolpropane triallyl ether or pentaerythritol triallyl ether
• CPC Class Codes: C08F 216/1416 Monomers containing oxygen in addition to the ether oxygen, e.g. allyl glycidyl ether
• CPC Class Codes: C08F 216/38 by an acetal or ketal radical
• CPC Class Codes: C08F 24/00 Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen cyclic esters of polyfunctional acids C08F18/00; cyclic anhydrides of unsaturated acids C08F20/00, C08F22/00

Abstract

Monomers, polymers and copolymers are provided that incorporate at least one naturally occurring phenolic compound, such as a plant phenol.

Claims

1. A compound comprising 1-(2-(4-allyl-2-methoxyphenoxy)ethoxy)ethyl acetate.

2. A method for making the compound of claim 1, the method comprising

contacting 4-allyl-2-methoxy-1-(2-(vinyloxy)ethoxy)benzene with acetic acid under conditions and for a time sufficient to yield the compound of claim 1.

3. A method for making a functionalized polymer or copolymer comprising:

contacting at least one vinyl ether monomer with the compound of claim 1 under conditions and for a time sufficient to yield the functionalized polymer or copolymer, wherein the functionalized polymer or copolymer comprises a terminal allyl group.

4. The method of claim 3 comprising contacting at least one vinyl ether monomer and at least one additional monomer with the 1-(2-(4-allyl-2-methoxyphenoxy)ethoxy)ethyl acetate under conditions and for a time sufficient to yield the allyl-functionalized polymer or copolymer.

5. The method of claim 3 further comprising reacting the allyl-functionalized polymer or copolymer with at least one second polymer or copolymer, to yield a block or graft copolymer produced through a reaction at the terminal allyl group of the functionalized polymer or copolymer.

6. The method of claim 5 wherein the block or graft copolymer comprises a poly(dimethylsiloxane) (PDMS).