IP Library Granted Patent US 8,921,464
Granted Patent B2
US 8,921,464 · App. 13/785,296 · Granted Dec 30, 2014

Adhesive compositions and use thereof

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Quick Facts
Patent No.
US 8,921,464
App. No.
13/785,296
Granted
Dec 30, 2014
Kind
B2
Abstract

The invention provides hot melt adhesives that comprise a templating agent, a polymer and a wax. It has been discovered that hot melt adhesives with an effective amount of templating agent have improved heat resistance than adhesives. The adhesives find particular use as case, carton, and tray forming, and as sealing adhesives, including heat sealing applications, for example in the packaging of cereals, cracker and beer products.

Claims (68)

1. A hot melt adhesive composition comprising:

a. an ethylene vinyl acetate copolymer or ethylene n-butyl acrylate copolymer;

b. a wax; and

c. a templating agent; and

wherein the copolymer has a melt index greater than 330 grams/10 minutes at 190° C/2.16 kg, measured in accordance with ASTM D1238;

wherein the templating agent is provided in an effective amount such that the ΔH of the adhesive is increased by at least 5% over the adhesive composition without the templating agent;

wherein the average crystal size in the adhesive composition is increased by at least 10% over the adhesive composition without the templating agent; and

wherein the heat resistance of the adhesive is increased by at least 5° F. over the adhesive composition without the templating agent.

2. The adhesive of claim 1 , comprising a templating agent in an amount of about 0.01 wt % to less than about 0.5 wt %, based on the total weight of the adhesive.

3. The adhesive of claim 1 wherein the templating agent is a sugar and sugar alcohol derivatives, or has a structure of:

Ar-L1-X-L2-R

wherein X is a sugar or a sugar alcohol;

Ar is a substituted or unsubstituted aryl-containing functional group;

R is H, alky, alkenyl, hydroxyl, alkoxy and alkyl-halide, or a substituted or unsubstituted aryl-containing functional group; and

L1 and L2, independently, are acetal or ether functional group.

4. The adhesive of claim 3 , wherein the X of the templating agent is selected from the group consisting of allose, altrose, fructose, galactose, glucose, gulose, idose, mannose, sorbose, talose, tagatose, arabinose, ribose, ribulose, xylose, xylulose, lyxose, erythrose, threose sorbitol and xylitol.

5. The adhesive of claim 4 wherein the templating agent is selected from the group consisting of 1,3:2,4 dibenzylidene sorbitol, 1,3:2,4 (4-methyldibenzylidene) sorbitol, bis(3,4dimethylbenzvlidene) sorbitol and bis(4-propylbenzylidene)propyl sorbitol.

6. The adhesive of claim 1 wherein the templating agent is selected form the group consisting of Li-12 OH stearate, Al stearate, Mg stearate, Ca stearate, 12-hydroxy stearic acid and mixtures thereof.

7. The adhesive of claim 1 wherein the templating agent is selected from the group consisting of phenyl esters, aliphatic amines, perfluoroalkanes, n-alkaneamides, arylamides, mono-amides, di-amides, tris-amides, polyamides, ammonium and phosphonium salts, amino acids, peptides, urea and thiourea, urethanes, ureido-pyrimidones, aminopyrimidones and their corresponding derivatives.

8. The adhesive of claim 1 wherein the wax is a petroleum-based wax, a synthetic wax, a naturally occurring wax or mixtures thereof.

9. The adhesive of claim 8 wherein the wax is a paraffin wax, a polyethylene wax, a polypropylene wax, a Fischer-Tropsch wax or mixtures thereof.

10. The adhesive of claim 1 further comprising a tackifier.

11. The adhesive of claim 10 optionally comprising a stabilizer, a plasticizer, an additive, or mixtures thereof.

12. An article comprising the adhesive of claim 1 .

13. The article of claim 12 which is a case, a tray or a carton.

14. A process for forming wax crystals in the adhesive of claim 1 comprising:

a) heating a first component until molten;

b) adding a templating agent to the first component until a homogenous first mixture is formed;

c) adding a second component to the first mixture to form a second mixture; and

d) cooling the second mixture to room temperature;

wherein the first and the second components are either the wax or the polymer;

wherein the first component has a lower crystallization temperature than that of the second component; and

wherein the second component is the remaining wax or polymer.

15. The process of claim 14 wherein the templating agent is a fatty acid or salt, or has a structure of:

Ar-L1-X-L2-R

wherein X is a sugar or a sugar alcohol;

Ar is a substituted or unsubstituted aryl-containing functional group;

R is H, alkys, alkenyls, hydroxyl, alkoxy and alkyl-halides or substituted or unsubstituted aryl-containing functional group; and

L1 and L2, independently, are acetal or ether functional group.

16. The process of claim 14 wherein the fatty acid or salt is selected from the group consisting of Li-12 OH stearate, Al stearate, Mg stearate, Ca stearate and 12-hydroxy stearate.

17. The process of claim 14 wherein the templating agent is selected from phenyl esters, aliphatic amines, perfluoroalkanes, n-alkaneamides, ammonium and phosphonium salts, amino acids, peptides, urea and thiourea, urethanes and corresponding derivatives and mixtures thereof.

18. A process for forming wax crystals in the adhesive of claim 1 further comprising a tackifier, wherein the process comprises:

e) heating a first component until molten;

f) adding a templating agent to the first component until a homogenous first mixture is formed;

g) adding a second component to the first mixture to form a second mixture; and

h) adding a third component to the second mixture to form a third mixture; and

i) cooling the third mixture to room temperature;

wherein the first, the second and the third components are either the wax, the tackifier or the polymer;

wherein the templating agent has the highest solubility in the first component than that of the second and third components;

wherein the second component has a lower crystallization temperature than that of the third component; and

wherein the third component is the remaining wax, tackifier or polymer.

19. A process for forming wax crystals in the adhesive of claim 1 further comprising a tackifier, wherein the process comprises:

a) heating a first component until molten;

b) adding a templating agent to the first component until a homogenous first mixture is formed;

c) adding a second component to the first mixture to form a second mixture; and

d) adding a third component to the second mixture to form a third mixture; and

e) cooling the third mixture to room temperature;

wherein the first, the second and the third components are either the wax, the tackifier or the polymer;

wherein the first component has the lowest melting temperature than that of the second and third components;

wherein the second component has a lower crystallization temperature than that of the third component; and

wherein the third component is the remaining wax, tackifier or polymer.

20. A hot melt adhesive composition comprising:

a. an ethylene vinyl acetate, ethylene n-butyl acrylate, ethylene-butene, ethylene-propylene, ethylene-hexene or ethylene-octene copolymer;

b. a wax; and

c. from about 0.01 wt % to less than about 0.5 wt %, a templating agent selected from the group consisting of fatty acid, fatty acid salt, n-alkeneamides, arylamides, mono polyamide, polydiamides, polytriamides, ureido-pyrimidone or aminopyrimidone;

wherein the ΔH of the adhesive is increased by at least 5% over an adhesive composition without the templating agent;

wherein the average crystal size in the adhesive is increased by at least 10% over the adhesive composition without the templating agent; and

wherein the heat resistance of the adhesive is increased by at least 5° F. over an adhesive composition without the templating agent.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059357/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2015
From: HENKEL US IP LLC
To: HENKEL IP & HOLDING GMBH
Reel/Frame 035101/0856 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2014
From: HENKEL CORPORATION
To: HENKEL US IP LLC
Reel/Frame 034186/0588 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2014
From: LIU, YAYUN; PAUL, CHARLES W.; XIAO, ALLISON; EODICE, ANDREA
To: HENKEL CORPORATION
Reel/Frame 032289/0317 →