IP Library Granted Patent US 8,765,851
Granted Patent B2
US 8,765,851 · App. 13/529,269 · Granted Jul 1, 2014

Free radical initiator modified hot melt adhesive composition including functionalized polyethylene and propylene-alpha-olefin polymer

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Quick Facts
Patent No.
US 8,765,851
App. No.
13/529,269
Granted
Jul 1, 2014
Kind
B2
Abstract

A hot melt adhesive composition that includes a first copolymer that includes the reaction product of a functionalized polyethylene, a propylene-alpha-olefin polymer that includes at least 50 mole % propylene and has a viscosity of no greater than 10,000 centipoise at 190° C., a ratio of z average molecular weight (Mz) to number average molecular weight (Mn) (Mz/Mn) of greater than 20, and a ratio of Mz to weight average molecular weight (Mw) (Mz/Mw) of greater than 3.0, and a free radical initiator.

Claims (55)

1. A hot melt adhesive composition comprising:

a first copolymer comprising the reaction product of

a functionalized polyethylene,

a propylene-alpha-olefin polymer comprising at least 50 mole % propylene and having a viscosity of no greater than 10,000 centipoise at 190° C., a ratio of z average molecular weight (Mz) to number average molecular weight (Mn) (Mz/Mn) of greater than 20, and a ratio of Mz to weight average molecular weight (Mw) (Mz/Mw) of greater than 3.0, and

a free radical initiator.

2. The adhesive composition of claim 1 having a viscosity of no greater than 2,000 centipoise at 177° C.

3. The adhesive composition of claim 1 having a viscosity of from about 400 to about 2,000 centipoise at 177° C.

4. The adhesive composition of claim 1 , wherein the adhesive composition exhibits a fiber tearing bond at −29° C. and at +60° C.

5. The adhesive composition of claim 1 , wherein the adhesive composition exhibits at least about 50% fiber tear at −29° C. and at +60° C.

6. The adhesive composition of claim 1 , wherein the first copolymer is formed from of at least 2% by weight of the functionalized polyethylene based on the weight of the first copolymer.

7. The adhesive composition of claim 1 , wherein the first copolymer is formed from at least about 10% by weight of the functionalized polyethylene based on the weight of the first copolymer.

8. The adhesive composition of claim 1 , wherein the first copolymer comprises the reaction product of at least about 2% by weight of maleated polyethylene and at least about 80% by weight of the propylene-alpha-olefin polymer.

9. The adhesive composition of claim 1 , wherein the first copolymer comprises the reaction product of at least about 10% by weight maleated polyethylene and at least about 85% by weight of the propylene-alpha-olefin polymer.

10. The adhesive composition of claim 1 , wherein the adhesive composition is homogeneous after aging for 96 hours at 177° C.

11. The adhesive composition of claim 1 exhibiting a single thermal melt transition temperature when tested using differential scanning calorimetry.

12. The adhesive composition of claim 1 exhibiting an initial Gardner color of no greater than 3.

13. The adhesive composition of claim 1 exhibiting a Gardner color after aging for 72hours at 177° C. of no greater than 5.

14. The adhesive composition of claim 1 , wherein the free radical initiator comprises peroxide.

15. The adhesive composition of claim 1 , wherein the propylene-alpha-olefin polymer comprises ethylene, butene, pentene, hexene, heptene, octene, nonene, decene, dodecene, or a combination thereof.

16. The adhesive composition of claim 1 , wherein the propylene-alpha-olefin polymer comprises at least 25 mole % butene.

17. The adhesive composition of claim 1 further comprising Fischer Tropsch wax, polyethylene wax, polypropylene wax, maleated polypropylene wax, or a combination thereof.

18. The adhesive composition of claim 1 , wherein the functionalized polyethylene comprises maleated polyethylene wax and the composition further comprises Fischer Tropsch wax, polyethylene wax, maleated polypropylene wax, or a combination thereof.

19. The adhesive composition of claim 1 , wherein the functionalized polyethylene comprises maleated polyethylene wax and the composition further comprises Fischer Tropsch wax.

20. The adhesive composition of claim 18 , further comprising an olefin polymer.

21. The adhesive composition of claim 1 further comprising at least about 5% by weight wax.

22. The adhesive composition of claim 1 further comprising at least about 5% by weight wax selected from the group consisting of polyethylene wax, maleated polypropylene wax, and Fischer Tropsch wax.

23. The adhesive composition of claim 1 , wherein the adhesive composition exhibits a set time of less than 15 seconds.

24. The adhesive composition of claim 1 , wherein the adhesive composition exhibits a set time of less than 10 seconds.

25. The adhesive composition of claim 1 , wherein the first copolymer comprises the reaction product of at least about 2% by weight maleated polyethylene and at least about 80% by weight propylene-alpha-olefin polymer, the adhesive composition further comprising at least about 5% by weight wax and having a viscosity no greater than 2,000 centipoise at 177° C.

26. The adhesive composition of claim 1 , exhibiting a Mz/Mn of greater than 18, and a Mz/Mw of from 2.3 to no greater than 6.

27. The adhesive composition of claim 1 , exhibiting a Mz/Mn of at least 27 and a Mz/Mw of from 2.3 to no greater than 4.

28. The adhesive composition of claim 1 further comprising tackifying agent.

29. The adhesive composition of claim 1 further comprising from at least 15% by weight to about 30% by weight tackifying agent.

30. The adhesive composition of claim 1 , wherein the first copolymer is formed from a reaction mixture comprising a polyfunctional acid.

31. The adhesive composition of claim 1 comprising at least about 55% by weight of the copolymer and further comprising a tackifying agent and a wax comprising Fischer Tropsch wax, polyethylene wax, polypropylene wax, maleated polypropylene wax, or a combination thereof.

32. The adhesive composition of claim 1 comprising at least about 70% by weight of the copolymer and further comprising a tackifying agent and a wax comprising Fischer Tropsch wax, polyethylene wax, polypropylene wax, maleated polypropylene wax, or a combination thereof.

33. A method of making a hot melt adhesive composition, the method comprising:

heating a mixture comprising

at least 80% by weight propylene-alpha-olefin polymer comprising at least 50 mole % propylene, the propylene-alpha-olefin polymer having a viscosity of no greater than 10,000 centipoise at 190° C., a ratio of z average molecular weight (Mz) to number average molecular weight (Mn) (Mz/Mn) of greater than 20, and a ratio of Mz to weight average molecular weight (Mw) (Mz/Mw) of greater than 3.0,

functionalized polyethylene, and

a free radical initiator.

34. The method of claim 33 , wherein the functionalized polyethylene comprises functionalized polyethylene wax.

35. The method of claim 33 , wherein the functionalized polyethylene comprises maleated polyethylene wax and the mixture comprises at least about 2% by weight of the maleated polyethylene wax.

36. The method of claim 33 , wherein the hot melt adhesive composition exhibits a fiber tearing bond at −29° C. and at +60° C.

37. The method of claim 33 , wherein the mixture further comprises a polyfunctional acid.

38. A hot melt adhesive composition comprising:

a copolymer comprising the reaction product of

a functionalized polyethylene,

a propylene-alpha-olefin polymer comprising at least 50 mole % propylene, and

a free radical initiator,

the hot melt adhesive composition exhibiting a ratio of z average molecular weight (Mz) to number average molecular weight (Mn) (Mz/Mn) of greater than 18, and a ratio of Mz to weight average molecular weight (Mw) (Mz/Mw) of from 2.3 to no greater than 6.

39. The hot melt adhesive composition of claim 38 , wherein the Mz/Mn is at least 27 and the Mz/Mw is from 2.5 to no greater than 6.

40. The hot melt adhesive composition of claim 38 , wherein the adhesive composition exhibits at least about 50% fiber tear at −29° C. and at +60° C.

41. The hot melt adhesive composition of claim 38 , wherein the functionalized polyethylene comprises functionalized polyethylene wax.

42. The hot melt adhesive composition of claim 1 further comprising filler.

Assignments (4)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) Recorded Feb 15, 2023
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
Reel/Frame 062761/0884 →
TERM LOAN SECURITY AGREEMENT Recorded Oct 25, 2017
From: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 044616/0671 →
RCF SECURITY AGREEMENT Recorded Oct 25, 2017
From: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 044616/0700 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2012
From: MILLER, RICHARD A.; DAVIS, KEVIN; WILLGING, STEPHEN M.; AHMED, SHARF U; ROSKA, TIMOTHY W
To: H. B. FULLER COMPANY
Reel/Frame 028906/0334 →