IP Library Granted Patent US 11,787,978
Granted Patent B2
US 11,787,978 · App. 16/775,948 · Granted Oct 17, 2023

Product assembly adhesives comprising 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 11,787,978
App. No.
16/775,948
Granted
Oct 17, 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 (27)

1. A product assembly hot melt adhesive composition, comprising:

about 5 parts to about 90 parts of at least at least one base polymer comprising at least one amorphous polyolefin,

about 5 parts to about 90 parts of at least one tackifier composition comprising 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,

about 0 parts to about 50 parts of at least one plasticizing oil,

about 0 parts to about 50 parts of at least one wax,

about 0 parts to about 80 parts of at least one filler, and

at least one additional antioxidant;

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, then 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 said thermoplastic hydrocarbon resin is a fully hydrogenated or partially hydrogenated C9 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.

2. The product assembly hot melt adhesive composition according to claim 1 , wherein said thermoplastic hydrocarbon resin has a Rolling Ball softening point between about 70° C. and about 150° C.

3. The product hot melt adhesive 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):

4. The product assembly hot melt adhesive composition according to claim 1 , wherein said secondary antioxidant is the hydroxyl-amine.

5. The product assembly hot melt adhesive 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-ditert.-butylphenol)pentaerythritol diphosphate (CAS 26741-53-7); Tris(2,4-di-tert.butyl phenyl) 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.

6. The product assembly hot melt adhesive composition according to claim 1 , wherein said secondary antioxidant is at least one selected from the group consisting of didodecyl-3,3′-thiodipropionate (CAS 123-28-4) and 3,3′-Thiodipropionic acid dioctadecylester (CAS 693-36-7).

7. The product assembly hot melt adhesive composition according to claim 4 , wherein said hydroxyl-amine are oxidized bis(hydrogenated tallow alkyl) amine (CAS: 143925-92-2).

8. The product assembly hot melt adhesive composition according to claim 1 , wherein said HALS is at least one selected from the group consisting of (A1)-(AX):

9. The product assembly hot melt adhesive composition according to claim 1 , wherein said HALS is present in an amount of about 0.05% to about 0.5% by weight based on the weight of said thermoplastic hydrocarbon resin.

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

11. An article comprising the product assembly hot melt adhesive composition of claim 1 .

12. The product assembly hot melt adhesive composition according to claim 1 , wherein said at least one additional antioxidant is present in an amount of at least about 1 part by weight.

13. The product assembly hot melt adhesive composition according to claim 1 , wherein said at least one additional antioxidant is present in an amount of about 0.2 to 1 part by weight.

14. The product assembly hot melt adhesive 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.

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 053159/0038 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2020
From: SIERA, JACOBUS
To: EASTMAN CHEMICAL MIDDELBURG B. V.
Reel/Frame 052173/0419 →
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 052173/0425 →