IP Library Granted Patent US 11,613,675
Granted Patent B2
US 11,613,675 · App. 16/775,962 · Granted Mar 28, 2023

Packaging 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
C09J7/35C08K3/013C08K5/0016C08K5/12C08K5/17C08K5/3435C08K5/372C08L91/06C09J123/0815C09J123/0853C09J153/00C09J2301/414
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Quick Facts
Patent No.
US 11,613,675
App. No.
16/775,962
Granted
Mar 28, 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 (54)

1. A hot melt packaging adhesive composition, comprising:

at least one base polymer, wherein:

(a) the at least one base polymer comprises an olefinic polymer, wherein the base polymer is present at about 10 to about 90 parts by weight, and wherein the olefinic polymer is one or more selected from: ethylene vinyl acetate (EVA), metallocene, and olefin block copolymer (OBC),

(b) the at least one base polymer comprises at least one amorphous polyolefin (APO) polymer, wherein the at least one base polymer is present at about 40 to about 90 parts by weight, and wherein the APO is one or more selected from: amorphous propylene (APP), amorphous propylene/ethylene (APE), amorphous propylene/butene (APB), amorphous propylene/hexene (APH), amorphous propylene/ethylene/butene, and amorphous poly alpha olefin (APAO),

(c) the at least one base polymer comprises at least one styrenic block copolymer (SBC), wherein the at least one base polymer is present at about 10 to about 90 parts by weight, and wherein the SBC is one or more selected from: styrene-butadiene-styrene (SBS), styrene-isoprene-styrene (SIS), styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene/propylene-styrene (SEPS) block copolymers, styrene-vinylbutadiene-styrene (SVS), styrene-butadiene diblock polymers (SB), and styrene-isoprene diblock polymers (SI),

and/or

(d) the at least one base polymer comprises at least one polyolefin (PO) polymer, wherein the at least one base polymer is present at about 10 to about 90 parts by weight, and wherein the PO is one or more selected from: linear low density polyethylene (LDPE), high density polyethylene (HDPE), atactic polypropylene (APP), polybutene-1, and oxidized polyethylene,

about 10 to about 80 parts by weight of at least one tackifier composition, which comprises at least one thermoplastic hydrocarbon resin and an antioxidant composition,

optionally at least one plasticizing oil,

optionally at least one wax,

optionally at least one filler, and

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

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

wherein the at least one tackifier composition comprises at least one fully hydrogenated or partially hydrogenated C9 resin; and

wherein a portion of the volatile organic compounds in the C9 resin has been removed.

2. The hot melt packaging adhesive composition according to claim 1 , further comprising:

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

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

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

3. The hot melt packaging adhesive composition according to claim 1 , wherein said packaging adhesive composition comprises about 50 to about 90 parts by weight of the at least one EVA polymer; and about 10 to about 50 parts by weight of the at least one tackifier composition.

4. The hot melt packaging adhesive composition according to claim 1 , wherein said packaging adhesive composition comprises about 10 to about 50 parts by weight of the at least one EVA polymer; about 10 to about 50 parts by weight of the at least one tackifier composition; and about 10 to about 50 parts by weight of the at least one wax.

5. The hot melt packaging adhesive composition according to claim 1 , wherein said packaging adhesive composition comprises about 30 to about 80 parts by weight of the at least one EVA polymer; and about 10 to about 50 parts by weight of the at least one tackifier composition.

6. The hot melt packaging adhesive composition according to claim 1 , wherein said packaging adhesive composition comprises:

about 20 to about 90 parts by weight of the at least one metallocene polymer;

about 10 to about 50 parts by weight of the at least one tackifier composition;

0 to about 40 parts by weight of the at least one plasticizing oil; and

0 to about 40 parts by weight of the at least one wax.

7. The hot melt packaging adhesive composition according to claim 1 , wherein said packaging adhesive composition comprises:

about 10 to about 50 parts by weight of the at least one olefin block copolymer (OBC)

about 30 to about 80 parts by weight of the at least one tackifier composition;

0 to about 40 parts by weight of the at least one oil; and

0 to about 20 parts by weight of the at least one wax.

8. The hot melt packaging adhesive composition according to claim 1 , wherein said packaging adhesive composition comprises:

about 40 to about 90 parts by weight of at least one amorphous poly alpha olefin (APAO) polymer;

about 10 to about 50 parts by weight of the at least one tackifier composition;

0 to about 20 parts by weight of the at least one oil; and

0 to about 20 parts by weight of the at least one wax.

9. The hot melt packaging adhesive composition according to claim 1 , wherein the thermoplastic hydrocarbon resin is at least one selected from the group consisting of: pure monomer thermoplastic resin (PMR), C5 thermoplastic resin, C5/C9 thermoplastic resin, C9 thermoplastic resin, terpene thermoplastic resin, indene-coumarone (IC) thermoplastic resin, dicyclopentadiene (DCPD) thermoplastic resin, hydrogenated or partially hydrogenated pure monomer (PMR) thermoplastic resin, hydrogenated or partially hydrogenated C5 thermoplastic resin, hydrogenated or partially hydrogenated C5/C9 thermoplastic resin, hydrogenated or partially hydrogenated C9 thermoplastic resin, hydrogenated or partially hydrogenated dicyclopentadiene (DCPD) thermoplastic resin, modified indene-coumarone (IC) thermoplastic resin, and mixtures thereof.

10. The hot melt packaging adhesive composition according to claim 1 , wherein said primary antioxidant is at least one sterically hindered phenol selected from 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 ;

11. The hot melt packaging adhesive composition according to claim 1 , wherein said secondary antioxidant is at least one selected from the group consisting of organo-phosphites, thioethers, and hydroxyl-amines.

12. The hot melt packaging adhesive composition according to claim 1 , wherein said second antioxidant 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); 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.

13. The hot melt packaging 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).

14. The hot melt packaging adhesive composition according to claim 11 , wherein said hydroxyl-amines are oxidized bis(hydrogenated tallow alkyl) amines (CAS: 143925-92-2).

15. The hot melt packaging adhesive composition according to claim 1 , wherein said hindered amine light stabilizer (HALS) is at least one selected from the group consisting of (A1)-(AX):

wherein R=H, CH 3 or OC 3 H 17

16. The hot melt packaging adhesive composition according to claim 1 , 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.

17. The hot melt packaging adhesive composition according to claim 1 , 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.

18. The hot melt packaging adhesive composition according to claim 15 , 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.

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

20. An article comprising the hot melt packaging adhesive composition of claim 15 .

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 053159/0032 →
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 052173/0404 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2020
From: SIERA, JACOBUS
To: EASTMAN CHEMICAL MIDDELBURG B. V.
Reel/Frame 052173/0416 →