Methods of using a phenolic fatty acid compound on a synthetic fabric material

Patent metadata

Field	Value
Publication number	US-11390987-B2
Application number	US-201515125534-A
Country	US
Kind code	B2
Filing date	Mar 13, 2015
Priority date	Mar 14, 2014
Publication date	Jul 19, 2022
Grant date	Jul 19, 2022

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 synthetic fabric material, comprising:
contacting a phenolic fatty acid compound with a synthetic fabric material having a functional group reactive to a carboxylic acid group of a fatty acid, to react the carboxylic acid-reactive functional group of the synthetic fabric material with the carboxylic acid group of the phenolic fatty acid compound, to introduce a hydroxy phenyl functional group into the synthetic fabric material; and
reacting the hydroxy phenyl functional group contained in the synthetic fabric material with a phenolic resin or a phenolic crosslinker composition capable of forming a phenolic resin, to chemically bond the phenolic resin with the synthetic fabric material.

2. The method of claim 1 , wherein the contacting step comprises:
liquefying the synthetic fabric material into a molten state; and
mixing the molten synthetic fabric material with the phenolic fatty acid compound.

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, IIIB, or VIIIA, a mixture of triflate salts, and combinations thereof.

4. The method of claim 1 , wherein the reacting step comprises:
dipping the synthetic fabric material in an aqueous solution of the phenolic resin or the phenolic crosslinker composition, thereby facilitating the chemical bonding of the phenolic resin with the synthetic fabric material.

5. The method of claim 1 , wherein the reaction of the hydroxy phenyl functional group with the phenolic resin or the phenolic crosslinker composition 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.

6. The method of claim 1 , wherein the synthetic fabric material is selected from the group consisting of nylon, rayon, polyester, aramid, polysulfone, and combinations thereof.

7. The method of claim 1 , wherein the phenolic resin is a monohydric, dihydric, or polyhydric phenol-aldehyde resin, wherein 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.

8. The method of claim 1 , wherein the phenolic resin further comprises an elastomeric latex.

9. The method of claim 8 , wherein the phenolic resin is a resorcinol-formaldehyde-latex solution.

10. The method of claim 1 , wherein the phenolic fatty acid compound comprises hydroxyphenyl stearic acid, hydroxyphenyl oleic acid, hydroxyphenyl linoleic acid, and combinations thereof.

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

12. The method of claim 1 , wherein the phenolic fatty acid compound ranges about 0.1 wt % to about 20 wt % of the synthetic fabric material.

13. The method of claim 1 , further comprising:
combining the phenolic resin on or in a circuit board substrate, a fiberglass, or a rubber composition, prior to or after the reacting step to chemically bond the phenolic resin with the synthetic fabric material.

14. A synthetic-fabric reinforced rubber composition, comprising:
a synthetic fabric phase that has been (a) modified by a phenolic fatty acid compound to contain a hydroxy phenyl functional group, and (b) coated with a phenolic resin, wherein the synthetic fabric phase and the coated phenolic resin are chemically bonded through the hydroxy phenyl functional group; and
a rubber composition.

15. The synthetic-fabric reinforced rubber composition of claim 14 , wherein the synthetic fabric-reinforced rubber composition is a component of a composition selected from the group consisting of a tire, belt, hose, printing roll, rubber shoe heel, rubber shoe sole, rubber wringer, automobile floor mat, mud flap for trucks, ball mill liner, and weather strip.

16. A synthetic-fabric reinforced article, comprising:
a synthetic fabric phase modified by a phenolic fatty acid compound to contain a hydroxy phenyl functional group, and
an article comprising a phenolic resin,
wherein the synthetic fabric phase and the article are chemically bonded through the hydroxy phenyl functional group.

17. The synthetic fabric-reinforced article of claim 16 , wherein the article is a rubber article.

18. The synthetic fabric-reinforced article of claim 16 , wherein the article is a circuit board substrate.

19. The synthetic fabric-reinforced article of claim 16 , wherein the article is a fiberglass.

Assignees

• Si Group Inc

Inventors

• Banach Timothy Edward
• Robideau Gary
• Howard L Scott
• Barbiero Gennaro

Classifications

• C07C51/367

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• D06M13/207 Primary

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

• C08J5/06

  using pretreated fibrous materials · CPC title

• D10B2101/06

  Glass · CPC title

• D06M15/37

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title