IP Library Granted Patent US 11,390,987
Granted Patent B2
US 11,390,987 · App. 15/125,534 · Granted Jul 19, 2022

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

Inventors: Timothy Edward Banach (Scotia, NY); Gary Robideau (Niskayuna, NY); L. Scott Howard (Ballston Spa, NY); Gennaro Barbiero (Niskayuna, NY)
Assignee: SI GROUP, INC.
D06M13/207C07C51/367C08J5/046C08J5/06D01F1/10D06M13/152D06M15/37D06M15/693C08J2321/00C08J2321/02C08J2461/12D06M2400/01D10B2101/06
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Quick Facts
Patent No.
US 11,390,987
App. No.
15/125,534
Granted
Jul 19, 2022
Kind
B2
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.

Claims (30)

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.

Assignments (7)
RELEASE OF SECURITY INTEREST Recorded Dec 30, 2025
From: ALTER DOMUS (US) LLC, AS COLLATERAL AGENT
To: SI GROUP, INC.
Reel/Frame 074136/0039 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS [REEL 068968/FRAME 0001] Recorded Dec 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS (US) LLC
Reel/Frame 069770/0736 →
RELEASE OF SECURITY INTEREST Recorded Nov 1, 2024
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: SI GROUP, INC.; ADDIVANT USA, LLC; SI GROUP USA (USAA), LLC (F/K/A ADDIVANT USA, LLC)
Reel/Frame 069290/0057 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 068968/0001 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 068968/0024 →
SECURITY INTEREST Recorded Nov 16, 2018
From: SI GROUP, INC.; ADDIVANT USA, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 048822/0965 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2017
From: BANACH, TIMOTHY EDWARD; ROBIDEAU, GARY; HOWARD, L. SCOTT; BARBIERO, GENNARO
To: SI GROUP, INC.
Reel/Frame 041263/0543 →
Continuity (2)
Provisional Application 61953462 · Mar 14, 2014
Related Publication 20170073884A1 · Mar 16, 2017