IP Library Granted Patent US 11,753,566
Granted Patent B2
US 11,753,566 · App. 16/775,932 · Granted Sep 12, 2023

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 11,753,566
App. No.
16/775,932
Granted
Sep 12, 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 (41)

1. A tackifier composition, comprising:

at least one partially or fully hydrogenated thermoplastic hydrocarbon resin, and

an antioxidant composition;

wherein a portion of volatile organic compounds in the at least one thermoplastic hydrocarbon resin has been removed;

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 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 tackifier composition 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):

wherein R═C 8 H 17 or C 18 H 37

wherein R═C 8 H 17 or C 12 H 25 ;

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

4. The tackifier composition 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-(nonylphenyl)-phosphite.

5. The tackifier composition according to claim 1 , wherein said HA-LS is at least one selected from the group consisting of: (A1)-(AX):

wherein R═H, CH 3 or OC 8 H 17

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

7. An adhesive composition comprising at least one base polymer and the at least one tackifier composition of claim 1 .

8. The adhesive composition according to claim 7 , wherein said base polymer is selected from the group consisting of: ethylene vinyl acetate copolymer, ethylene n-butyl acrylate copolymer, ethylene methyl acrylate copolymer, polyester, neoprene, acrylics, urethane, poly(acrylate), ethylene acrylic acid copolymer, polyether ether ketone, polyamide, styrenic block copolymers, random styrenic copolymers, hydrogenated styrenic block copolymers, styrene butadiene copolymers, natural rubber, polyisoprene, polyisobutylene, atactic polypropylene, polyethylene including atactic polypropylene, ethylene-propylene polymers, propylene-hexene polymers, ethylene-butene polymers, ethylene octene polymers, propylene-butene polymers, propylene-octene polymers, metallocene-catalyzed polypropylene polymers, metallocene-catalyzed polyethylene polymers, ethylene-propylene-butylene terpolymers, copolymers produced from propylene, ethylene, and various C4-C10 alpha-olefin monomers, polypropylene polymers, functional polymers, butyl rubber, polyester copolymers, copolyester polymers, isoprene, the terpolymer formed from the monomers ethylene, propylene, and a bicyclic olefin, isoprene-based block copolymers, butadiene-based block copolymers, acrylate copolymers, butadiene acrylonitrile rubber, and polyvinyl acetate.

9. The adhesive composition of claim 7 , wherein said primary antioxidant is pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate), and wherein said HALS is bis(2,2,6,6,-tetramethyl-4-piperidyl) sebacate.

10. An adhesive composition, wherein said adhesive composition is a pressure sensitive adhesive (PSA), wherein said PSA comprises:

about 5 parts to about 90 parts by weight of at least one base polymer;

about 5 parts to about 90 parts by weight of at least one tackifier composition;

wherein the tackifier composition comprises at least one thermoplastic hydrocarbon resin and an antioxidant composition;

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, 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 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; and

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

0 to about 50 parts by weight of at least one plasticizer;

0 to about 50 parts by weight of at least one wax;

0 to about 1 part by weight of at least one additional antioxidant; and

0 to about 80 parts by weight of at least one filler.

11. An article comprising the adhesive composition of claim 7 .

12. The tackifier composition 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 tackifier composition 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 053159/0041 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2020
From: SIERA, JACOBUS
To: EASTMAN CHEMICAL MIDDELBURG B. V.
Reel/Frame 052173/0422 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2020
From: YUAN, BING; DICKERSON, JAMES PALMER; LIEW, BEE KIM; OSBORNE, CHRISTOPHER WAYNE
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 052173/0429 →