IP Library Granted Patent US 9,267,060
Granted Patent B2
US 9,267,060 · App. 13/768,887 · Granted Feb 23, 2016

Reaction product of propylene polymer and wax, graft copolymers derived from polypropylene polymer and wax, hot melt adhesive compositions including the same, and methods of using and making the same

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Quick Facts
Patent No.
US 9,267,060
App. No.
13/768,887
Granted
Feb 23, 2016
Kind
B2
Abstract

A reaction product and hot melt adhesive compositions that include the reaction product are disclosed. The reaction product includes the reaction product of a first polymer that includes at least one of polypropylene homopolymer and polypropylene-alpha-olefin copolymer, a first wax that includes at least one of polyethylene wax, Fischer Tropsch wax and paraffin wax, and a free radical initiator and has a viscosity of no greater than 12,000 centipoise at 177° C.

Claims (61)

1. A propylene-wax copolymer comprising:

the reaction product of components comprising

a first polymer comprising polypropylene homopolymer, polypropylene-alpha-olefin copolymer, or a combination thereof,

a first wax comprising polyethylene wax, Fischer Tropsch wax, or a combination thereof, and

a free radical initiator, and

being free of an unsaturated compound that includes at least one functional group and has a molecular weight no greater than 1000 g/mole,

the reaction product having a number average molecular weight greater than 5000 g/mole, a polydispersity index of no greater than 5, and a viscosity of no greater than 12,000 centipoise at 177° C.

2. A propylene-wax copolymer comprising:

the reaction product of components comprising

a first polymer comprising polypropylene homopolymer, polypropylene-alpha-olefin copolymer, or a combination thereof,

a first wax comprising polyethylene wax, and

a free radical initiator,

the reaction product having a number average molecular weight greater than 5000 g/mole, a polydispersity index no greater than 5, and a viscosity of no greater than 12,000 centipoise at 177° C.

3. A propylene-wax copolymer comprising:

the reaction product of components comprising

a first polymer having a polydispersity index of no greater than 5 and comprising polypropylene homopolymer, polypropylene-alpha-olefin copolymer, or a combination thereof,

a first wax comprising polyethylene wax, Fischer Tropsch wax, paraffin wax, or a combination thereof,

a free radical initiator, and

being free of an unsaturated compound comprising at least one functional group and having a molecular weight no greater than 1000 g/mole,

the reaction product exhibiting a viscosity of no greater than 12,000 centipoise at 177° C.

4. The copolymer of claim 1 , wherein the reaction product exhibits a set time of no greater than 10 seconds.

5. The copolymer of claim 1 , wherein the reaction product exhibits a set time of no greater than 5 seconds.

6. A composition comprising the copolymer of claim 1 .

7. A hot melt adhesive composition comprising the copolymer of claim 1 .

8. The hot melt adhesive composition of claim 7 , wherein the hot melt adhesive composition exhibits an initial Gardner color of no greater than 3.

9. The hot melt adhesive composition of claim 7 , further comprising tackifying agent, plasticizer, wax, or a combination thereof.

10. The hot melt adhesive composition of claim 7 , wherein the composition is free of gelling after aging for 96 hours at 177° C.

11. The hot melt adhesive composition of claim 7 , wherein the composition exhibits an energy to break of at least 0.15 Joules.

12. The hot melt adhesive composition of claim 7 , wherein the composition exhibits a heat stress resistance of at least 60° C.

13. The hot melt adhesive composition of claim 7 , wherein the composition exhibits a tensile strength of at least 1.38 MPa.

14. The hot melt adhesive composition of claim 7 , wherein the composition exhibits a strain at break of at least about 100%.

15. The hot melt adhesive composition of claim 7 , wherein the composition exhibits an energy to break of at least 0.15 Joules and a strain at break of at least 100%.

16. The hot melt adhesive composition of claim 7 , wherein the composition exhibits an energy to break of at least 0.15 Joules and a heat stress resistance of at least 60° C.

17. The hot melt adhesive composition of claim 7 , wherein the composition exhibits an energy to break of at least 0.15 Joules and a strain at break of at least 100%, and further comprises a second wax selected from the group consisting of polyethylene wax, polypropylene wax, Fischer Tropsch wax, paraffin, maleated polypropylene wax, and maleated polyethylene wax.

18. The hot melt adhesive composition of claim 7 , wherein the composition exhibits an energy to break of at least 0.15 Joules and a heat stress resistance of at least 60° C., and further comprises a second wax selected from the group consisting of polyethylene wax, polypropylene wax, Fischer Tropsch wax, paraffin, maleated polypropylene wax, and maleated polyethylene wax.

19. The hot melt adhesive composition of claim 7 , wherein the hot melt adhesive composition exhibits an energy to break of at least 0.15 Joules, a tensile strength of at least 3.28 MPa, a heat stress resistance of at least 65° C., or a combination thereof.

20. The hot melt adhesive composition of claim 7 further comprising a nucleating agent.

21. The copolymer of claim 1 , wherein the first wax comprises a non-functionalized wax, and the components further comprise a second wax, the second wax comprising a functionalized wax.

22. A method of making a graft copolymer, the method comprising:

blending a first polymer and a first wax in the presence of a free radical initiator for a period of time and under sufficient conditions to achieve a reaction product having a number average molecular weight greater than 5000 g/mole and a polydispersity index of no greater than 5,

the first polymer comprising polypropylene homopolymer, polypropylene-alpha-olefin copolymer, or a combination thereof, and

the first wax comprising polyethylene wax.

23. A method of making a graft copolymer, the method comprising:

blending a first polymer and a first wax in the presence of a free radical initiator and in the absence of an unsaturated compound comprising at least one functional group and having a molecular weight no greater than 1000 g/mole for a period of time and under sufficient conditions to achieve a reaction product having a number average molecular weight greater than 5000 g/mole and a polydispersity index of no greater than 5,

the first polymer comprising polypropylene homopolymer, polypropylene-alpha-olefin copolymer, or a combination thereof, and

the first wax comprising polyethylene wax, paraffin wax, Fischer Tropsch wax, or a combination thereof.

24. An article comprising:

a first substrate; and

a composition comprising the copolymer of claim 1 disposed on the substrate.

25. The article of claim 24 , wherein the first substrate comprises cardboard.

26. The propylene-wax copolymer of claim 2 , wherein the components further comprise an unsaturated compound that includes at least one functional group.

27. The propylene-wax copolymer of claim 26 , wherein the unsaturated compound comprises maleic acid, maleic anhydride, fumaric acid, or a combination thereof.

28. A hot melt adhesive composition comprising the copolymer of claim 2 .

29. A hot melt adhesive composition comprising the copolymer of claim 3 .

30. A propylene-wax copolymer comprising:

a reaction product of components comprising

a first polymer comprising polypropylene homopolymer, polypropylene-alpha-olefin copolymer, or a combination thereof,

a first wax comprising polyethylene wax, Fischer Tropsch wax, or a combination thereof, and

a free radical initiator,

the reaction product having a viscosity at 177° C. that is less than the viscosity of a blend of the components of the reaction product other than the free radical initiator,

the reaction product having a number average molecular weight greater than 5000 g/mole, a polydispersity index of no greater than 5, and a viscosity of no greater than 12,000 centipoise at 177° C. greater than 5000 g/mole, a polydispersity index of no greater than 5, and a viscosity of no greater than 12,000 centipoise at 177° C.

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 Nov 20, 2013
From: DAVIS, KEVIN P.; AHMED, SHARF U.; CHASE, CHERYL L.; MANSOUR, AMEARA S.; LAWRENCE, MAYNARD R.; SCHMIDT, SCOTT C.
To: H. B. FULLER COMPANY
Reel/Frame 031640/0249 →