IP Library Granted Patent US 11,725,122
Granted Patent B2
US 11,725,122 · App. 16/775,999 · Granted Aug 15, 2023

Processes for making low volatile tackifier compositions

Inventors: Bing Yuan (Methuen, MA); James Palmer Dickerson (Kingsport, TN); Bee Kim Liew (Kingsport, TN); Christopher Wayne Osborne (Johnson City, TN); Jacobus Siera (Hoogerheide, NL)
Assignee: Synthomer Adhesive Technologies LLC
C09J7/35A61L15/20A61L15/225A61L15/585C08K3/013C08K5/0016C08K5/13C08K5/1345C08K5/17C08K5/3435C08K5/3492C08K5/372C08K5/375C08K5/52C08K5/5393C08L23/0853C08L23/26C08L53/02C08L91/06C09J7/381C09J11/06C09J11/08C09J123/0815C09J123/0853C09J123/26C09J153/00C09J153/02C08K5/005C08K5/105C08K5/12C08K5/34926C09J2301/408C09J2301/414C09J2453/00
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Quick Facts
Patent No.
US 11,725,122
App. No.
16/775,999
Granted
Aug 15, 2023
Kind
B2
Abstract

A tackifier composition comprising at least one thermoplastic hydrocarbon resin and an antioxidant composition is provided; wherein a portion of the volatile organic compounds in the thermoplastic hydrocarbon resin has been removed; wherein the antioxidant composition comprises at least one primary antioxidant and at least one secondary antioxidant; and wherein the levels of individual volatile organic compound monitored in the tackifier composition are less than about 0.5 ppm as measured by GC/MS headspace analysis. Processes for producing the tackifier composition are also provided as well as adhesives comprising the tackifier compositions.

Claims (24)

1. A process for making a tackifier composition, said process comprising the following steps performed in the following order:

(a) polymerization of one or more monomers to form at least one partially or fully hydrogenated thermoplastic hydrocarbon resin;

(b) removing at least a portion of volatile organic compounds from the at least one thermoplastic hydrocarbon resin; and

(c) adding an antioxidant composition to said at least one thermoplastic hydrocarbon resin;

wherein the antioxidant composition comprises at least one primary antioxidant, at least one secondary antioxidant, and at least one hindered amine light stabilizer (HALS);

wherein said primary antioxidant is a hindered phenolic antioxidant or a secondary arylamine, and wherein said primary antioxidant is present in an amount of about 0.1% to about 1% based on the weight of the thermoplastic hydrocarbon resin;

wherein said secondary antioxidant is an organo-phosphite or a hydroxyl-amine, and wherein said secondary antioxidant is present in an amount of about 0.1% to about 1% based on the weight of said thermoplastic hydrocarbon resin;

wherein when said primary antioxidant is a hindered phenolic antioxidant, said secondary antioxidant is a hydroxyl-amine;

wherein when said secondary antioxidant is an organo-phosphite, then said primary antioxidant is a secondary arylamine;

wherein the antioxidant composition is added to the at least one thermoplastic resin both before and after step (b) to produce the tackifier composition;

wherein the levels of individual volatile organic compound in the tackifier composition are less than about 0.5 ppm as measured by GC/MS headspace analysis; and

wherein the amount of said HALS ranges from about 0.05% to about 0.5% by weight based on the weight of said at least one thermoplastic hydrocarbon resin.

2. The process according to claim 1 , wherein said primary antioxidant is the sterically hindered phenol and is selected from one or more of the group consisting of (CI)-(CXIX):

3. The process according to claim 1 , wherein said primary antioxidant is the secondary arylamine.

4. The process according to claim 1 , wherein said secondary antioxidant is the organo-phosphite and is selected from the group consisting of: 2,2′,T-Nitrilo[triethyl-[3,3,5,5-tetra-tert.-butyl-1,1-biphenyl-2,2-diyl] phosphite (CAS 80410-33-9); Bis(2,4-di-tert.-butyl-6-methylphenyl)-ethyl-phosphite (CAS 145650-60-8); Tris(2,4-di-tert.butylphenyl) phosphite (CAS 31570-04-4); Tetrakis(2,4-di-tert-butylphenyl)[1,1-biphenyl]-4,4′-diylbisphosphonite (CAS 119345-01-6); and Tri-(nonylphenol)-phosphite.

5. The process according to claim 1 , wherein said HALS is at least one selected from the group consisting of: (AII)-(AX):

6. The process according to claim 1 , wherein said volatile organic compounds are removed from said thermoplastic hydrocarbon resin by at least one process selected from the group consisting of: membrane separation, selective precipitation, selective polymerization conditions, evaporation and distillation, and preparative gel permeation chromatography.

7. The process according to claim 6 wherein said evaporation and distillation comprises steam stripping.

8. The process according to claim 7 wherein said steam stripping is conducted in a counter current contacting device.

9. The process according to claim 8 , wherein said contacting device is operated under vacuum at about 10 mbar to about 1000 mbar.

10. The process according to claim 8 , wherein said contacting device is operated at a temperature of about 180° C. to about 280° C.

11. The process according to claim 6 , wherein a rotary film evaporator is utilized to remove the volatile organic compounds from said thermoplastic hydrocarbon resin.

12. The process according to claim 1 , wherein said primary antioxidant is pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate), wherein said HALS is bis(2,2,6,6,-tetramethyl-4-piperidyl) sebacate, and wherein said thermoplastic hydrocarbon resin is C9 thermoplastic resin.

13. The process according to claim 1 , wherein said thermoplastic hydrocarbon resin is C9 thermoplastic resin.

Assignments (5)
SECURITY INTEREST Recorded May 1, 2026
From: SYNTHOMER ADHESIVE TECHNOLOGIES LLC
To: GLAS TRUST CORPORATION LIMITED, AS SECURITY AGENT
Reel/Frame 075312/0405 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 25, 2022
From: EASTMAN CHEMICAL COMPANY
To: SYNTHOMER ADHESIVE TECHNOLOGIES LLC
Reel/Frame 059701/0508 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2020
From: EASTMAN CHEMICAL MIDDELBURG B.V.
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 053159/0021 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2020
From: YUAN, BING; DICKERSON, JAMES PALMER; LIEW, BEE KIM; OSBORNE, CHRISTOPHER WAYNE
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 052011/0756 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2020
From: SIERA, JACOBUS
To: EASTMAN CHEMICAL MIDDELBURG B. V.
Reel/Frame 052011/0803 →
Continuity (6)
Provisional Application 62799383 · Jan 31, 2019
Provisional Application 62841498 · May 1, 2019
Provisional Application 62841507 · May 1, 2019
Provisional Application 62841511 · May 1, 2019
Provisional Application 62841515 · May 1, 2019
Related Publication 20200248047A1 · Aug 6, 2020