Terpene resin-and hydrocarbon resin-based surfactants and aqueous dispersion of tackifier resins
View Patent ↗A process for preparing a surfactant, useful for dispersing tackifier resins in aqueous media, comprises reacting an αβ-unsaturated carboxylic acid or anhydride, or an ester thereof, with a terpene- or hydrocarbon-based resin to form an adduct, then reacting the adduct with a polyalkylene polyol to yield the surfactant. In a related embodiment, the surfactant is subsequently functionalized. Also disclosed are surfactants prepared using a disclosed process; compositions comprising a disclosed surfactant and a tackifier resin; aqueous dispersions comprising a disclosed surfactant; tackifier resin and water; adhesive compositions comprising a disclosed aqueous dispersion and a polymer latex; and pressure sensitive adhesive overlays prepared using a disclosed adhesive composition.
1. A process for preparing a surfactant comprising:
reacting an α,β-unsaturated carboxylic acid or anhydride, or an ester thereof, with a resin comprising hydrocarbon monomeric residues, to provide an adduct;
reacting the adduct with either alkylene oxide or a carboxyl-reactive poly(alkylene oxide) to provide the surfactant; and
modifying the surfactant by either phosphorylation or sulfonation to provide a functionalized hydrophilic surfactant.
2. The process of claim 1 wherein the resin is selected from the group consisting of a polyterpene resin, a terpene-phenol resin, a terpene-hydrocarbon resin, a terpene-vinyl aromatic resin, a hydrocarbon resin, and a vinyl aromatic-modified hydrocarbon resin.
3. The process of claim 1 wherein the α,β-unsaturated carboxylic acid is maleic acid, and the α,β-unsaturated carboxylic anhydride is maleic anhydride.
4. The process of claim 1 wherein the resin is a polyterpene resin having a softening point of about 10° C. to about 150° C.
5. The process of claim 1 wherein the resin comprises one or more monomeric residues independently selected from the group consisting of α-pinene, β-pinene, limonene, dipentene, β-phellandrene, δ-3-carene, and δ-2-carene.
6. The process of claim 5 wherein the resin further comprises one or more monomeric residues independently selected from the group consisting of isobutylene, a 1-alkene, a 2-alkene, a trisubstituted alkene, and vinylcyclohexene.
7. The process of claim 5 wherein the resin further comprises one or more monomeric residues independently selected from the group consisting of piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-bytene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
8. The process of claim 1 wherein the resin is a terpene-phenol resin and comprises one or more monomeric residues independently selected from the group consisting of α-pinene, β-pinene, δ-3-carene and limonene.
9. The process of claim 8 wherein the terpene-phenal resin further comprises one or more monomeric residues independently selected from the group consisting of styrene, indene, α-methylstyrene, an alkyl aromatic styrene, divinylbenzene, a divinylbenzene with one or more alkyl groups, isobutylene, dilsobutylene, a 1-alkene, a 2-alkene, a trisubstituted alkene, vinylcyclohexene, piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-butene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
10. The process of claim 8 wherein the phenol is independently selected from the group consisting of phenol, a monosubstituted phenol, a disubstituted phenol, a trisubstituted phenol and a hydroxyl-substituted naphthalene compound.
11. The process of claim 1 wherein the resin comprises one or more monomeric residues independently selected from the group consisting of piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-butene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
12. The process of claim 1 wherein the adduct is reacted with poly(ethylene glycol) or a mixture of more than one polyethylene glycol).
13. The process of claim 1 , wherein the adduct is reacted with ethylene oxide.
14. The surfactant of claim 1 .
15. A composition comprising the surfactant of claim 1 and a tackifier resin.
16. An adhesive composition comprising:
the surfactant of claim 1 ;
a tackifier resin;
a polymer latex; and water.
17. An aqueous dispersion comprising water and a composition comprising a surfactant and a tackifier resin, wherein the surfactant is prepared by a process comprising:
reacting an α,β-unsaturated carboxylic acid or anhydride, or an ester thereof, with a resin comprising hydrocarbon monomeric residues, to provide an adduct, and
reacting the adduct with either alkylene oxide or a carboxyl-reactive poly(alkylene oxide) to provide the surfactant.
18. The aqueous dispersion of claim 17 wherein the resin comprising hydrocarbon monomeric residues is selected from the group consisting of a polyterpene resin, a terpene-phenol resin, a terpene-hydrocarbon resin, a terpene-vinylaromatic resin, a hydrocarbon resin, and a vinyl aromatic-modified hydrocarbon resin.
19. The aqueous dispersion of claim 17 wherein the process further comprising modifying the surfactant by either phosphorylation or sulfonation to provide a functionalized surfactant.
20. The aqueous dispersion of claim 17 wherein the α,β-unsaturated carboxylic acid is maleic acid, and the α,β-unsaturated carboxylic anhydride is maleic anhydride.
21. The aqueous dispersion of claim 17 wherein the resin comprising hydrocarbon monomeric residues is a polyterpene resin having a softening point of about 10° C. to about 150° C.
22. The aqueous dispersion of claim 17 wherein the resin comprising hydrocarbon monomeric residues comprises one or more monomeric residues independently selected from the group consisting of α-pinene, β-pinene, limonene, dipentene, β-phellandrene, δ-3-carene, and δ-2-carene.
23. The aqueous dispersion of claim 22 wherein the resin comprising hydrocarbon monomeric residues further comprises one or more monomeric residues independently selected from the group consisting of isobutylene, a 1-alkene, A 2-alkene, a trisubstituted alkene, and vinylcyclohexene.
24. The aqueous dispersion of claim 22 wherein the resin comprising hydrocarbon monomeric residues further comprises one or more monomeric residues independently selected from the group consisting of piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-butene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
25. The aqueous dispersion of claim 17 wherein the resin comprising hydrocarbon monomeric residues is a terpene-phenol resin and comprises one or more monomeric residues independently selected from the group consisting of α-pinene, β-pinene, δ-3-carene and limonene.
26. The aqueous dispersion of claim 25 wherein the terpene-phenol resin further comprises one or more monomeric residues independently selected from the group consisting of styrene, indene, α-methyl styrene, an alkyl aromatic styrene, divinylbenzene, a divinylbenzene with one or more alkyl groups, isobutylene, diisobutylene, a 1-alkene, a 2-alkene, a trisubstituted alkene, vinylcyclohexene, piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-butene, cyclopentene, an acyclic pentene, cyclopentadlene, and dicyclopentadlene.
27. The aqueous dispersion of claim 25 wherein the phenol is independently selected from the group consisting of phenol, a monosubstituted phenol, a disubstituted phenol, a trisubstituted phenol and a hydroxyl-substituted naphthalene compound.
28. The aqueous dispersion of claim 17 wherein the resin comprising hydrocarbon monomeric residues comprises one or more monomeric residues independently selected from the group consisting of piperylenei isoprene, 2-methyl-2-bytene, 2-methyl-1-bytene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicycl opentadiene.
29. The aqueous dispersion of claim 17 wherein the adduct is reacted with poly(ethylene glycol) or a mixture of more than one poly(ethylene glycol).
30. The aqueous dispersion of claim 17 wherein the adduct is reacted with ethylene oxide.
31. An adhesive composition comprising a surfactant, a tackifier resin, a polymer latex, and water, wherein the surfactant is prepared by a process comprising:
reacting an α,β-unsaturated carboxylic acid or anhydride, or an ester thereof, with a resin comprising hydrocarbon monomeric residues, to provide an adduct, and
reacting the adduct with either alkylene oxide or a carboxyl-reactive poly(alkylene oxide) to provide the surfactant.
32. The adhesive composition of claim 31 wherein the resin comprising hydrocarbon monomeric residues is selected from the group consisting of a polyterpene resin, a terpene-phenol resin, a terpene-hydrocarbon resin, a terpene-vinyl aromatic resin, a hydrocarbon resin, and a vinyl aromatic-modified hydrocarbon resin.
33. The adhesive composition of claim 31 wherein the process further comprising modifying the surfactant by either phosphorylation or sulfonation to provide a functionalized surfactant.
34. The adhesive composition of claim 31 wherein the α,β-unsaturated carboxylic acid is malaic acid, and the α,β-unsaturated carboxylic anhydride is maleic anhydride.
35. The adhesive composition of claim 31 wherein the resin comprising hydrocarbon monomeric residues is a polyterpene resin having a softening point of about 10° C. to about 150° C.
36. The adhesive composition of claim 31 wherein the resin comprising hydrocarbon monomeric residues comprises one or more monomeric residues independently selected from the group consisting of α-pinene, β-pinene, limonene, dipentene, β-phellandrene, δ-3-carene, and δ-2-carene.
37. The adhesive composition of claim 36 wherein the resin comprising hydrocarbon monomeric residues further comprises one or more monomeric residues independently selected from the group consisting of isobutylene, a 1-alkene, a 2-alkene, a trisubstituted alkene, and vinylcyclohexene.
38. The adhesive composition of claim 36 wherein the resin comprising hydrocarbon monomeric residues further comprises one or more monomeric residues independently selected from the group consisting of piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-bytene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
39. The adhesive composition of claim 31 wherein the resin comprising hydrocarbon monomeric residues is a terpene-phenol resin and comprises one or more monomeric residues independently selected from the group consisting of α-pinene, β-pinene, δ-3-carene and limonene.
40. The adhesive composition of claim 39 wherein the terpene-phenol resin further comprises one or more monomeric residues independently selected from the group consisting of styrene, indene, α-methylstyrene, an alkyl aromatic styrene, divinylbenzene, a divinylbenzene with one or more alkyl groups, isobutylene, diisobutylene, a 1-alkene, a 2-alkene, a trisubstituted alkens, vinylcyclohexene, piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-butene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
41. The adhesive composition of claim 39 wherein the phenol is independently selected from the group consisting of phenol, a monosubstituted phenol, a disubstituted phenol, a trisubstituted phenol and a hydroxyl-substituted naphthalene compound.
42. The adhesive composition of claim 31 wherein the resin comprising hydrocarbon monomeric residues comprises one or more monomeric residues independently selected from the group consisting of piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-butene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
43. The adhesive composition of claim 31 wherein the adduct is reacted with poly(ethylene glycol) or a mixture of more than one poly(ethylene glycol).
44. The adhesive composition of claim 31 wherein the adduct is reacted with ethylene oxide.
45. A pressure sensitive adhesive overlay prepared by applying a layer of an adhesive composition to a surface of a substrate, and drying the layer, wherein the adhesive composition comprises a surfactant, a tackifier resin, a polymer latex, and water, wherein the surfactant is prepared by a process comprising:
reacting an α,β-unsaturated carboxylic acid or anhydride, or an ester thereof, with a resin comprising hydrocarbon monomeric residues, to provide an adduct, and
reacting the adduct with either alkylene oxide or a carboxyl-reactive poly(alkylene oxide) to provide the surfactant.
46. The pressure sensitive adhesive overlay of claim 45 wherein the resin comprising hydrocarbon monomeric residues is selected from the group consisting of a polyterpene resin, a terpene-phenol resin, a terpene-hydrocarbon resin, a terpene-vinyl aromatic resin, a hydrocarbon resin, and a vinyl aromatic-modified hydrocarbon resin.
47. The pressure sensitive adhesive overlay of claim 45 wherein the resin comprising hydrocarbon monomeric residues is selected from the group consisting of a polyterpene resin, a terpene-phenol resin, a terpene-hyrdrocarbon resin, a terpene-vinylaromatic resin, a hydrocarbon resin, and a vinyl aromatic -modified hydrocarbon resin.
48. The pressure sensitive adhesive overlay of claim 45 wherein the α,β-unsaturated carboxylic acid is maleic acid, and the α,β-unsaturated carboxylic anhydride is maleic anhydride.
49. The pressure sensitive adhesive overlay of claim 45 wherein the resin comprising hydrocarbon monomeric residues is a polyterpene resin having a softening point of about 10° C. to about 150° C.
50. The pressure sensitive adhesive overlay of claim 45 wherein the resin comprising hydrocarbon monomeric residues comprises one or more monomeric residues independently selected from the group consisting of α-pinene, β-pinene, limonene, dipentene, phellandrene, δ-3-carene, and δ-2-carene.
51. The pressure sensitive adhesive overlay of claim 50 wherein the resin comprising hydrocarbon monomeric residues further comprises one or more monomeric residues independently selected from the group consisting of isobutylene, a 1-alkene, a 2-alkene, a trisubstituted alkene, and vinylcyclohexene.
52. The pressure sensitive adhesive overlay of claim 50 wherein the resin comprising hydrocarbon monomeric residues further comprises one or more monomeric residues independently selected from the group consisting of piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-butene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
53. The pressure sensitive adhesive overlay of claim 45 wherein the resin comprising hydrocarbon monomeric residues is a terpene-phenol resin and comprises one or more monomeric residues independently selected from the group consisting of α-pinene, β-pinene, δ-3-carene and limonene.
54. The pressure sensitive adhesive overlay of claim 53 wherein the terpene-phenol resin further comprises one or more monomeric residues independently selected from the group consisting of styrene, indens, a-metthylstyrene, an alkyl aromatic styrene, divinylbenzene, a divinylbenzene with one or more alkyl groups, isobutylene, diisobutylene, a 1-alkene, a 2-alkene, a trisubstituted alkene, vinylcyclohexene, piperylene, isoprene, 2-methyl-2-butene, 2-methyl-1-bytene, cyclopertene, an acyclic pentene, eyclopentadiene, and dicyclopentadiene.
55. The pressure sensitive adhesive overlay of claim 53 wherein the phenol is independently selected from the group consisting of phenol, a monosubstituted phenol, a disubstituted phenol, a trisubstituted phenol, and a hydroxyl-substituted naphthalene compound.
56. The pressure sensitive adhesive overlay of claim 45 wherein the resin comprising hydrocarbon monomeric residues comprises one or more monomeric residues independently selected from the-group consisting of piperylene, isoprene, 2-methyl-2-bytene, 2-methyl-1-butene, cyclopentene, an acyclic pentene, cyclopentadiene, and dicyclopentadiene.
57. The pressure sensitive adhesive overlay of claim 45 wherein the adduct is reacted with poly(ethylene glycol) or a mixture of more than one poly(ethylene glycol).
58. The pressure sensitive adhesive overlay of claim 45 therein the adduct is reacted with ethylene oxide.