IP Library Granted Patent US 12,012,500
Granted Patent B2
US 12,012,500 · App. 17/135,594 · Granted Jun 18, 2024

Low free 2-mercaptoethanol ester and uses thereof

Inventors: Kevin John Ross (Rockwood, CA); Gene Kelly Norris (West Chester, OH); Jeremy Dunlap (Walton, KY)
Assignee: PMC Organometallix, Inc.
C08K5/58C07C319/12C07C319/28C07C323/12C08K5/0016C08K5/36C08K5/37C08K5/57C08L27/06C08L2201/08
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Quick Facts
Patent No.
US 12,012,500
App. No.
17/135,594
Granted
Jun 18, 2024
Kind
B2
Abstract

A novel Low Free 2-MercaptoEthanol Ester has been used to prepare Alkyl Tin Reverse Ester Stabilizers as well as used to enhance the thermal performance of those Alkyl Tin Reverse Ester Stabilizers or Alkyl Tin Thioglycolate Stabilizers or Alkyl Tin Mercaptides for PVC applications where odor during PVC compounding, processing, or of the final PVC article has prevented widespread use of Alkyl Tin Reverse Ester Stabilizers.

Claims (16)

1. A method of using a Low Free 2-MercaptoEthanol Ester (LFMEE) that is obtained through removal of 2-MercaptoEthanol from a standard 2-MercaptoEthanol Ester, wherein the resulting LFMEE have residual 2-Mercaptoethanol below 1.0 wt % to enhance thermal performance of alkyl tin thioglycolate ester stabilizers, wherein the standard 2-MercaptoEthanol Ester is formed by a reaction of 2-mercaptoethanol with C16-C18 fatty acid, the method comprising:

blending LFMEE with the alkyl tin thioglycolate ester stabilizer,

wherein the LFMEE and stabilizer are combined in a ratio ranging from 5 wt % LFMEE:95 wt % stabilizer to 25 wt % LFMEE:75 wt % stabilizer.

2. A method of using a Low Free 2-MercaptoEthanol Ester (LFMEE) that is obtained through removal of 2-MercaptoEthanol from a standard 2-MercaptoEthanol Ester, wherein the resulting LFMEE have residual 2-Mercaptoethanol below 1.0 wt % to enhance thermal performance of alkyl tin reverse ester stabilizers, wherein the standard 2-MercaptoEthanol Ester is formed by a reaction of 2-mercaptoethanol with C16-C18 fatty acid, the method comprising steps of:

blending LFMEE with the alkyl tin reverse ester stabilizer,

wherein the LFMEE and stabilizer are combined in a ratio ranging from 5 wt % LFMEE:95 wt % stabilizer to 25 wt % LFMEE:75 wt % stabilizer.

3. A method of using a Low Free 2-MercaptoEthanol Ester (LFMEE) that is obtained through removal of 2-MercaptoEthanol from a standard 2-MercaptoEthanol Ester, wherein the resulting LFMEE have residual 2-Mercaptoethanol below 1.0 wt % to enhance thermal performance of alkyl tin mercaptide and carboxylate stabilizers, wherein the standard 2-MercaptoEthanol Ester is formed by a reaction of 2-mercaptoethanol with C16-C18 fatty acid, the method comprising steps of:

combining LFMEE with the alkyl tin mercaptide and carboxylate stabilizer,

wherein the LFMEE and stabilizer are combined in a ratio ranging from 5 wt % LFMEE:95 wt % stabilizer to 25 wt % LFMEE: 75 wt % stabilizer.

4. The method of claim 3 wherein the mercaptide is chosen from the group consisting of dodecylmercaptan or carboxylates.

5. The method of claim 3 wherein the carboxylate is Maleates.

6. The method of claim 3 wherein the stabilizer further includes sulfide bridging for alkyl groups ranging of C1-C8.

7. The method of claim 3 wherein the alkyl tin stabilizers comprise alkyl tin groups, and the alkyl tin groups can include monooctyl tin and dioctyl tin components, wherein the monooctyl tin and dioctyl tin components of the alkyl tin groups are in ranges from 0 wt % to 100 wt % dioctyl tin and 0 wt % to 100 wt % monooctyl tin and all combinations between.

8. The method of claim 1 wherein the resulting stabilizer composition further comprises a booster, the booster chosen from the group consisting of: Ca/Zn-based boosters, organic-based stabilizers, BHT, polyols, metallic salts or other co-stabilizers.

9. The method of claim 1 wherein the LFMEE and stabilizer are combined in a ratio ranging from 0 wt % LFMEE:90 wt % stabilizer to 15 wt % LFMEE:85 wt % stabilizer.

10. The method of claim 3 wherein the LFMEE and stabilizer are combined in a ratio ranging from 0 wt % LFMEE:90 wt % stabilizer to 15 wt % LFMEE:85 wt % stabilizer.

Assignments (2)
SECURITY INTEREST Recorded Jun 27, 2025
From: PMC ORGANOMETALLIX, INC.; CRYSTAL, INC. - PMC
To: PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 071545/0315 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2021
From: ROSS, KEVIN JOHN; NORRIS, GENE KELLY; DUNLAP, JEREMY
To: PMC ORGANOMETALLIX, INC.
Reel/Frame 056700/0568 →
Continuity (4)
Continuation 16554275 · Aug 28, 2019
Provisional Application 62878040 · Jul 24, 2019
Provisional Application 62723943 · Aug 28, 2018
Related Publication 20210188768A1 · Jun 24, 2021