Methods of using phenolic fatty acid compound on a non-phenolic polymer

Patent metadata

Field	Value
Publication number	US-10030332-B2
Application number	US-201515125532-A
Country	US
Kind code	B2
Filing date	Mar 13, 2015
Priority date	Mar 14, 2014
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

This invention relates to a process for making phenolic fatty acid compounds having a reduced phenolic ester content. The invention also relates to method for chemically bonding a phenolic resin with a non-phenolic polymer (e.g., a synthetic fabric). The method comprises contacting a phenolic fatty acid compound with a non-phenolic polymer to introduce a hydroxy phenyl functional group into the non-phenolic polymer; and reacting the hydroxy phenyl functional group contained in the non-phenolic polymer with a phenolic resin or a phenolic crosslinker composition capable of forming a phenolic resin, to chemically bond the phenolic resin with the non-phenolic polymer. The invention is particularly useful for making a synthetic fabric-reinforced article, such as synthetic fabric-reinforced rubber article, circuit board substrate, or fiberglass.

First claim

We claim:

1. A method for chemically bonding a phenolic resin with a non-phenolic polymer, comprising:
contacting a phenolic fatty acid compound with a non-phenolic polymer having a functional group reactive to a carboxylic acid group of a fatty acid, to react the carboxylic acid-reactive functional group of the non-phenolic polymer with the carboxylic acid group of the phenolic fatty acid compound, thereby attaching a hydroxy phenyl functional group to the non-phenolic polymer; and
reacting the hydroxy phenyl functional group of the non-phenolic polymer with a phenolic resin or a phenolic crosslinker composition capable of forming a phenolic resin, to chemically bond the phenolic resin with the non-phenolic polymer,
wherein the non-phenolic polymer is an acrylic compound prepared from an ethylenically unsaturated monomer component comprising butyl acrylate, methyl methacrylate, hydroxy propyl methacrylate, hydroxy ethyl acrylate, glycidyl methacrylate, acrylic acid, methacrylic acid, acetoacetoxy ethyl methacrylate, a phosphate ester of monomethacrylate, or combinations thereof.

2. The method of claim 1 , wherein, without the presence of the phenolic fatty acid compound, the non-phenolic polymer does not react, or reacts minimally, with the phenolic resin.

3. The method of claim 1 , wherein the contacting occurs in the presence of a metal-based catalyst selected from the group consisting of antimony-based catalyst, tin-based catalyst, titanium-based catalyst, and co-catalyst of phosphorus and a metal element, and combinations thereof; or an acidic catalyst selected from the group consisting of a lewis acid, a sulfonic acid, a triflic acid, a triflate salt of a metal of Group IIA, IIB, IIIA, TIM, or VIIIA, a mixture of triflate salts, and combinations thereof.

4. The method of claim 1 , wherein the reaction of the hydroxy phenyl functional group with the phenolic resin or the phenolic crosslinker occurs in the presence of a basic catalyst selected from the group consisting of ammonium hydroxide, tertiary amines, alkali and alkaline earth metal oxides and hydroxides, and combinations thereof.

5. The method of claim 1 , wherein the phenolic resin is a monohydric, dihydric, or polyhydric phenol-aldehyde resin, wherein the monohydric, dihydric, or polyhydric phenol of the phenol-aldehyde resin is unsubstituted or substituted with one or more linear, branched, or cyclic C 1 -C 30 alkyl groups.

6. The method of claim 1 , wherein the phenolic resin is a solution in water or an organic solvent.

7. The method of claim 1 , wherein the phenolic fatty acid compound is selected from the group consisting of hydroxyphenyl stearic acid, hydroxyphenyl oleic acid, hydroxyphenyl linoleic acid, and combinations thereof.

8. The method of claim 1 , wherein the phenolic fatty acid compound comprises [9,10]-(p-hydroxyphenyl)-octadecanoic acid.

9. The method of claim 1 , wherein the phenolic fatty acid compound ranges from about 0.1 wt % to about 50 wt % of the non-phenolic polymer.

Assignees

• Si Group Inc
• Akzo Nobel Coatings Int Bv

Inventors

• Banach Timothy Edward
• Bode Daniel
• Stella Guy
• Craun Gary

Classifications

• D06M13/224

  Esters of carboxylic acids; Esters of carbonic acid · CPC title

• C08J5/06

  using pretreated fibrous materials · CPC title

• C08G81/024

  Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G · CPC title

• D06M13/207

  Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof · CPC title

• D01F1/10

  Other agents for modifying properties · CPC title