IP Library Granted Patent US 9,023,929
Granted Patent B2
US 9,023,929 · App. 11/053,682 · Granted May 5, 2015

Tackifier dispersion

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Quick Facts
Patent No.
US 9,023,929
App. No.
11/053,682
Granted
May 5, 2015
Kind
B2
Abstract

The invention relates to a tackifier dispersion comprising a resinous material and an emulsifier, the emulsifier being obtainable by a method comprising providing an ester of one or more fatty acids containing at least two conjugated double bonds, reacting the ester with a dienophile containing an acid or anhydride group, to form an intermediate product A, and, reacting the intermediate product A with one or more polyalkylene glycols. The invention also relates to a method for the production of a tackifier dispersion, its use as a tackifier, and an adhesive composition comprising the tackifier dispersion. The invention further relates to an emulsifier, a method of producing the same and its use for emulsifying resinous materials.

Claims (82)

1. A tackifier dispersion comprising:

a resinous material;

an emulsifier;

wherein:

the resinous material is a hydrocarbon resin or a rosin, or a mixture of any two or more thereof;

the emulsifier comprises a reaction product of an intermediate product A with one or more polyalkylene glycols, said intermediate product A being a reaction product of an ester of one or more fatty acids containing at least two conjugated double bonds and a dienophile containing an acid or anhydride group;

the one or more polyalkylene glycols have a number average molecular weight from 3000 to 8000; and

the emulsifier has a number average molecular weight of about 4000 to about 12,000.

2. The tackifier of claim 1 , wherein a weight ratio of intermediate product A to the one or more polyalkylene glycols, based on total amount of the intermediate product A and the one or more polyalkylene glycols, is from about 0.05:1 to about 5:1.

3. The tackifier of claim 1 , wherein a weight ratio of the ester of one or more fatty acids to the dienophile is less than about 25:1.

4. The tackifier of claim 1 , wherein a weight ratio of the ester of one or more fatty acids to the dienophile is from about 1:1 to about 8:1.

5. The tackifier of claim 1 , wherein the ester of one or more fatty acids has an iodine number of more than about 60.

6. The tackifier of claim 1 , wherein the ester of one or more fatty acids is a triglyceride of one or more fatty acids.

7. The tackifier of claim 6 , wherein the triglyceride is linseed oil, soybean oil or sunflower oil.

8. The tackifier of claim 1 , wherein the dienophile is an alpha-beta ethylenically unsaturated carboxylic acid or anhydride.

9. The tackifier of claim 8 , wherein the dienophile is maleic acid, maleic anhydride or fumaric acid.

10. The tackifier of claim 1 , wherein the one or more polyalkylene glycols are C 2 -C 5 polyalkylene glycols or C 2 -C 5 polyalkylene glycol mono alkyl ethers.

11. The tackifier of claim 1 , wherein the one or more polyalkylene glycols are a mixture of a polyalkylene glycol having an average molecular weight, determined by hydroxyl number analysis, from about 500 to about 2500, with a polyalkylene glycol having an average molecular weight from 3000 to 5000.

12. The tackifier of claim 1 , wherein at least one of the one or more polyalkylene glycols is a polyethylene glycol.

13. The tackifier of claim 1 , wherein at least one of the one or more polyalkylene glycols is a methoxy polyethylene glycol or a butoxy polyethylene glycol.

14. The tackifier of claim 1 , wherein the emulsifier has an iodine number from about 0 to about 20 g iodine per 100 g of emulsifier.

15. The tackifier of claim 1 , wherein the resinous material is a hydrocarbon resin.

16. The tackifier of claim 1 , wherein the resinous material is a rosin.

17. The tackifier of claim 1 , wherein the emulsifier is present in an amount from about 5 to about 8% by weight, based on the weight of resinous material.

18. The tackifier of claim 1 , having a solids content of at least 50% by weight.

19. An emulsifier comprising:

a reaction product of an intermediate product A with one or more polyalkylene glycols, said intermediate product A being a reaction product of an ester of one or more fatty acids containing at least two conjugated double bonds and a dienophile, the dienophile comprising an acid or anhydride group;

wherein:

the one or more polyalkylene glycols have a number average molecular weight from 3000 to 8000; and

wherein:

the emulsifier has a number average molecular weight of about 4000 to about 12,000.

20. The emulsifier of claim 19 , wherein a weight ratio the intermediate product A to the one or more polyalkylene glycols, based on total amount of the intermediate product A and the one or more polyalkylene glycols, is from about 0.05: 1 to about 5:1.

21. The emulsifier of claim 19 , wherein a weight ratio of the ester of one or more fatty acids to the dienophile is less than about 25:1.

22. The emulsifier of claim 19 , wherein a weight ratio of the ester of one or more fatty acids to the dienophile is from about 1:1 to about 8:1.

23. The emulsifier of claim 19 , wherein the ester of one or more fatty acids has an iodine number of more than about 60.

24. The emulsifier of claim 19 , wherein the ester of one or more fatty acids is a triglyceride of one or more fatty acids.

25. The emulsifier of claim 24 , wherein the triglyceride is linseed oil, soybean oil or sunflower oil.

26. The emulsifier of claim 19 , wherein the dienophile is an alpha-beta ethylenically unsaturated carboxylic acid or anhydride.

27. The emulsifier of claim 19 , wherein the dienophile is maleic acid, maleic anhydride or fumaric acid.

28. The emulsifier of claim 19 , wherein the one or more polyalkylene glycols are C 2 -C 5 polyalkylene glycols or C 2 -C 5 polyalkylene glycol mono alkyl ethers.

29. The emulsifier of claim 19 , wherein the one or more polyalkylene glycols are a mixture of a polyalkylene glycol having an average molecular weight, determined by hydroxyl number analysis, from about 500 to about 2500, with a polyalkylene glycol having a number average molecular weight from 3000 to 5000.

30. The emulsifier of claim 19 , wherein at least one of the one or more polyalkylene glycols is a polyethylene glycol.

31. The emulsifier of claim 19 , wherein at least one of the one or more polyalkylene glycols is a methoxy polyethylene glycol or a butoxy polyethylene glycol.

32. The emulsifier of claim 19 , wherein the emulsifier has an iodine number from about 0 to about 20 g iodine per 100 g of emulsifier.

33. A process for the production of a tackifier dispersion, the process comprising:

dispersing a resinous material in an aqueous phase in the presence of an emulsifier;

wherein:

the resinous material is a hydrocarbon resin or a rosin, or a mixture of any two or more thereof;

the emulsifier being obtainable by a method comprising:

providing an ester of one or more fatty acids containing at least two conjugated double bonds;

reacting the ester of one or more fatty acids with a dienophile containing an acid or anhydride group to form an intermediate product A; and

reacting the intermediate product A with one or more polyalkylene glycols;

wherein:

the one or more polyalkylene glycols have a number average molecular weight of 3000 to 8000; and

the emulsifier has a number average molecular weight of about 4000 to about 12,000.

34. The process of claim 33 , wherein a weight ratio the intermediate product A to the one or more polyalkylene glycols, based on total amount of the intermediate product A and the one or more polyalkylene glycols, is from about 0.05:1 to about 5:1.

35. The process of claim 33 , wherein a weight ratio of the ester of one or more fatty acids to the dienophile is from about 1:1 to about 8:1.

36. A process for the production of an emulsifier, the process comprising:

providing an ester of one or more fatty acids containing at least two conjugated double bonds;

reacting the ester with a dienophile containing an acid or anhydride group to form an intermediate product A;

reacting the intermediate product A with one or more polyalkylene glycols having a number average molecular weight of more than 3000; and

wherein:

the emulsifier has a number average molecular weight of about 4000 to about 12,000.

37. The process of claim 36 , wherein a weight ratio intermediate product A to one or more polyalkylene glycols, based on total amount of the intermediate product A and the one or more polyalkylene glycols, is from about 0.05:1 to about 5:1.

38. The process of claim 36 , wherein a weight ratio of the ester of one or more fatty acids to the dienophile is from about 1:1 to about 8:1.

39. A composition comprising:

one or more polymers; and

a tackifier dispersion;

wherein:

said tackifier dispersion comprises:

a resinous material; and

an emulsifier comprising a reaction product of an intermediate product A with one or more polyalkylene glycols;

the resinous material is a hydrocarbon resin or a rosin, or a mixture of any two or more thereof;

said intermediate product A comprising:

a reaction product of an ester of one or more fatty acids containing at least two conjugated double bonds; and

a dienophile containing an acid or anhydride group;

the one or more polyalkylene glycols have a number average molecular weight of 3000 to 8000; and

the emulsifier has a number average molecular weight of about 4000 to about 12,000.

40. The tackifier of claim 1 , wherein the one or more polyalkylene glycols have an average molecular weight from 3500 to 4500.

41. The emulsifier of claim 19 , wherein the one or more polyalkylene glycols have an average molecular weight from 3500 to 4500.

42. The process of claim 33 , wherein the one or more polyalkylene glycols have an average molecular weight from 3500 to 4500.

43. The composition of claim 39 , wherein the one or more polyalkylene glycols have an average molecular weight from 3500 to 4500.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Feb 23, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION (SUCCESSOR BY MERGER TO WILMINGTON TRUST FSB), AS COLLATERAL AGENT
To: HEXION INC. (FORMERLY KNOWN AS HEXION SPECIALTY CHEMICALS INC.); BORDEN CHEMICAL FOUNDRY, LLC; HEXION INVESTMENTS INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INVESTMENTS, INC.); HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; HEXION INTERNATIONAL INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INTERNATIONAL INC.); OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
Reel/Frame 041793/0001 →
CHANGE OF NAME Recorded Mar 16, 2011
From: HEXION SPECIALTY CHEMICALS, INC.
To: MOMENTIVE SPECIALTY CHEMICALS INC.
Reel/Frame 025967/0012 →
SECURITY AGREEMENT Recorded Feb 5, 2010
From: HEXION LLC; HEXION SPECIALTY CHEMICALS, INC.; BORDEN CHEMICAL FOUNDRY, LLC; BORDEN CHEMICAL INVESTMENTS, INC.; HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; BORDEN CHEMICAL INTERNATIONAL, INC.; OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 023905/0451 →
SECURITY INTEREST Recorded Jan 29, 2010
From: HEXION SPECIALTY CHEMICALS, INC.; BORDEN CHEMICAL FOUNDRY, LLC; BORDEN CHEMICAL INVESTMENTS, INC.; HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; BORDEN CHEMICAL INTERNATIONAL, INC.; OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
To: WILMINGTON TRUST FSB, AS COLLATERAL AGENT
Reel/Frame 023963/0038 →