Farnesene-based tackifying resins and adhesive compositions containing the same

Patent metadata

Field	Value
Publication number	US-11512234-B2
Application number	US-202016739924-A
Country	US
Kind code	B2
Filing date	Jan 10, 2020
Priority date	Jan 10, 2020
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

An adhesive composition made from an elastomer and a tackifying resin. The tackifying resin includes a farnesene polymer or copolymer having the following properties: i) less than 10 weight percent of volatile organic compounds; ii) Mn between 300 Da and 1000 Da; iii) Mw between 400 Da and 3000 Da; iv) Mw/Mn between 1.00 and 3.00; v) Tg between −50° C. and 20° C.; and vi) viscosity between 400,000 cP and 1,000,000 cP at 25° C. A method of making the farnesene-based polymer or copolymer includes combining a farnesene monomer and a solvent and optionally adding one or more co-monomers selected from dienes, branched mono-olefins, and vinyl aromatics, to provide a monomer feed, and polymerizing the monomer feed by combining it with a Friedel-Crafts initiator in a vessel. The farnesene-based polymer or copolymer tackifier may be combined with one or more elastomers and one or more other tackifiers to form an adhesive composition.

First claim

We claim:

1. An adhesive composition comprising an elastomer and a tackifying resin, wherein the tackifying resin comprises a farnesene polymer or copolymer having the following properties:
i) less than 10 weight percent of volatile organic compounds (VOC), as measured by thermogravimetric analysis (TGA) as percent weight loss during 1 hour at 110° C.;
ii) a number average molecular weight (Mn) between 300 Da and 500 Da;
iii) a weight average molecular weight (Mw) between 400 Da and 800 Da;
iv) Mw/Mn between 1.00 and 3.00;
v) a glass transition temperature (Tg) between −50° C. and 20° C.; and
vi) a viscosity between 400,000 cP and 1,000,000 cP at 25° C.

2. The adhesive composition according to claim 1 , wherein the farnesene comprises β-farnesene.

3. The adhesive composition according to claim 1 , wherein the glass transition temperature of the farnesene polymer or copolymer is between −50° C. and 0° C.

4. The adhesive composition according to claim 1 , wherein the elastomer is selected from the group consisting of styrene-isoprene block copolymers, polyacrylate resins, poly ethylene vinyl acetate (EVA) resins, polystyrene butadiene resins, random styrene butadiene (SBR) copolymers, styrene-butadiene block copolymers, styrene-isoprene-butadiene-styrene (SIBS) copolymers, styrene-ethylene-propylene-styrene (SEPS) copolymers, styrene-ethylene-butylene-styrene (SEBS) block copolymers, amorphous poly-olefin (APO) resins, and mixtures thereof.

5. The adhesive composition according to claim 1 , wherein the farnesene polymer or copolymer further comprises, as polymerized monomers, no more than 90 weight percent of at least one co-monomer.

6. The adhesive composition according to claim 1 , wherein the farnesene polymer or copolymer further comprises, as polymerized monomers, no more than 40 weight percent of at least one co-monomer.

7. The adhesive composition according to claim 5 , wherein the at least one co-monomer is selected from the group consisting of aromatic olefins, non-aromatic olefins, aromatic diolefins, non-aromatic diolefins, and mixtures thereof.

8. The adhesive composition according to claim 5 , wherein the at least one co-monomer is selected from the group consisting of styrene; alpha-methylstyrene; cis-1,3-pentadiene; trans-1,3pentadiene; 2-methyl-1-butene; 2-methyl-2-butene; pinene; limonene; myrcene; 2-methyl-1-pentene; 2-methyl-2-pentene; p-methyl styrene; indene; 3-methylindene; cyclopentadiene; 1-methylcyclopentadiene; and mixtures thereof.

9. The adhesive composition according to claim 5 , wherein the at least one co-monomer is selected from the group consisting of cis-1,3-pentadiene; trans-1,3-pentadiene; 2-methyl-1-butene; 2-methyl-2-butene; styrene; alpha-methyl styrene; and mixtures thereof.

10. A farnesene polymer comprising one or more polymerized monomers, wherein the one or more polymerized monomers comprises farnesene; wherein the farnesene polymer has the following properties:
i) less than 10 weight percent of volatile organic compounds (VOC), as measured by thermogravimetric analysis (TGA) as percent weight loss during 1 hour at 110° C.;
ii) a number average molecular weight (Mn) between 300 Da and 500 Da;
iii) a weight average molecular weight (Mw) between 400 Da and 800 Da;
iv) a Mw/Mn of not more than 3.00;
v) a glass transition temperature (Tg) between −50° C. and 20° C.; and
vi) a viscosity between 400,000 cP and 1,000,000 cP at 25° C.

11. The farnesene polymer according to claim 10 , wherein the farnesene comprises β-farnesene.

12. The farnesene polymer according to claim 10 , wherein the glass transition temperature of the farnesene polymer is between −50° C. and 0° C.

13. The farnesene polymer according to claim 10 , wherein the farnesene polymer further comprises, as polymerized monomers, no more than 90 weight percent, limits included, of at least one co-monomer.

14. The farnesene polymer according to claim 13 , wherein the at least one co-monomer is selected from the group consisting of aromatic olefins, non-aromatic olefins, aromatic diolefins, non-aromatic diolefins, and mixtures thereof.

15. The farnesene polymer according to claim 13 , wherein the at least one co-monomer is selected from the group consisting of styrene; alpha-methylstyrene; cis-1,3-pentadiene; trans-1,3-pentadiene; 2-methyl-1-butene; 2-methyl-2-butene; pinene; limonene; myrcene; 2-methyl-1-pentene; 2-methyl-2-pentene; p-methyl styrene; indene; 3-methylindene; cyclopentadiene; 1-methyl cyclopentadiene; and mixtures thereof.

16. The farnesene polymer according to claim 13 , wherein the at least one co-monomer is selected from the group consisting of cis-1,3-pentadiene; trans-1,3-pentadiene; 2-methyl-1-butene; 2-methyl-2-butene; styrene; alpha-methylstyrene; and mixtures thereof.

17. A method of preparing the farnesene polymer according to claim 10 , the method comprising the steps of:
a) combining a farnesene monomer, an organic solvent, between 300 ppm weight and 3000 ppm by weight of a proton source, and an optional at least one co-monomer, to form a monomer feed;
b) combining the monomer feed with a Friedel-Crafts polymerization initiator in a vessel to form a polymerization mixture; and
c) allowing the polymerization mixture to polymerize the farnesene monomer and the optional at least one co-monomer to form the farnesene polymer.

18. The method according to claim 17 , wherein the farnesene monomer comprises β-farnesene.

19. The method according to claim 17 , wherein the monomer feed comprises between 0 weight percent and 90 weight percent, limits included, of the at least one co-monomer based on the total amount of farnesene monomer and the at least one co-monomer.

20. The method according to claim 17 , wherein the monomer feed comprises between 0 weight percent and 40 weight percent, limits included, of the at least one co-monomer based on the total amount of farnesene monomer and the at least one co-monomer.

21. The method according to claim 19 , wherein the at least one co-monomer is selected from the group consisting of styrene; alpha-methylstyrene; cis-1,3-pentadiene; trans-1,3-pentadiene; 2-methyl-1-butene; 2-methyl-2-butene; pinene; limonene; myrcene; 2-methyl-1-pentene; 2-methyl-2-pentene; p-methyl styrene; indene; 3-methylindene; cyclopentadiene; 1-methyl cyclopentadiene; and mixtures thereof.

22. The method according to claim 17 , wherein the Friedel-Crafts polymerization initiator comprises boron trifluoride.

23. A method of preparing the adhesive composition according to claim 1 , the method comprising the steps of:
a) combining a farnesene monomer, an organic solvent, between 300 ppm weight and 3000 ppm weight of a proton source, and an optional at least one co-monomer, to form a monomer feed;
b) combining the monomer feed with a Friedel-Crafts polymerization initiator in a vessel to form a polymerization mixture;
c) allowing the polymerization mixture to polymerize the farnesene monomer and the optional at least one co-monomer to form the farnesene polymer; and
d) combining the farnesene polymer with the elastomer and optionally, one or more further additives to form the adhesive composition, wherein the farnesene polymer is used in an amount effective to impart tackiness to the adhesive composition.

24. The method according to claim 23 , wherein the farnesene monomer comprises β-farnesene.

Assignees

• Fina Technology

Inventors

• Nelson Keith A
• Keefe Violeta N
• Hansen Nestor

Classifications

• C08F136/22 Primary

  the radical having three or more carbon-to-carbon double bonds · CPC title

• C08F236/22

  the radical having three or more carbon-to-carbon double bonds · CPC title

• C08L9/00

  Compositions of homopolymers or copolymers of conjugated diene hydrocarbons · CPC title

• C09J147/00 Primary

  Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Adhesives based on derivatives of such polymers (C09J145/00 takes precedence; based on conjugated diene rubbers C09J109/00 - C09J121/00) · CPC title

• C08F210/14

  Monomers containing five or more carbon atoms · CPC title