Alkylphenol resins and a method of preparing thereof
Compositions, methods, and resins using alkyl aldehydes and phenols are provided herein. In one embodiment, a composition comprising an alkylphenol resin can be prepared by condensing at least one phenolic monomer selected from the group consisting of phenol, cresol, resorcinol, xylenol, ethyl phenol, alkylresorcinols, and combinations thereof; and at least one alkyl aldehyde having from 5 to 12 carbon atom alkyl groups. The alkylphenol resins of the application are free of octylphenol or nonylphenol monomers. In one embodiment, the alkylphenol resins may be prepared using formaldehyde, and alternatively, in another embodiment, the alkylphenol resins may be prepared without the use of formaldehyde. The process to make these new alternative alkylphenol resins is a cost effective process and easy to scale-up.
1. A composition comprising an alkylphenol resin condensation product of a reaction mixture, comprising:
at least one phenolic monomer selected from the group consisting of phenol, cresol, resorcinol, xylenol, ethyl phenol, alkylresorcinols, and combinations thereof;
formaldehyde;
an organic solvent selected from the group of an aliphatic hydrocarbon solvent, an aromatic hydrocarbon solvent or combination therein, wherein the organic solvent forms an azeotrope with water;
an acid catalyst;
a base catalyst;
water; and
at least one alkyl aldehyde having from 5 to 12 carbon atom alkyl groups, wherein the alkylphenol resin condensation product has a molecular weight from 2000 Daltons to 50000 Daltons, and wherein the alkylphenol resin condensation product comprises a relative solubility number from about 7.5 to about 12.5, wherein the alkylphenol resin condensation product comprises a resole alkylphenol resin condensation product.
2. The composition of claim 1 , wherein the phenolic monomers have a concentration of octylphenol and nonylphenol monomers from 0% to less than 5% by weight of the total weight of phenolic monomers.
3. The composition of claim 1 , wherein the phenolic monomers are free of octylphenol and nonylphenol monomers.
4. A method of making the alkylphenol resin of claim 1 comprising condensing a reaction mixture comprising:
at least one phenolic monomer selected from the group consisting of phenol, cresol, resorcinol, xylenol, ethyl phenol, alkylresorcinols, and combinations thereof; and
at least one alkyl aldehyde having from 5 to 12 carbon atom alkyl groups.
5. The method of claim 4 , wherein the reaction mixture has a concentration of octylphenol and nonylphenol monomers from 0% to less than 5% by weight of the total weight of phenolic monomers.
6. The method of claim 4 , wherein the condensation reaction is free of formaldehyde.
7. The method of claim 4 , wherein the reaction mixture further comprises formaldehyde.
8. The method of claim 4 , wherein the alkylphenol resin comprises a novolac resin or a resole resin.
9. The method of claim 4 , wherein the reaction mixture further comprises an acid catalyst, a base catalyst, an organic solvent, or combinations thereof.
10. An article of manufacture prepared using the alkylphenol resin of claim 1 prepared by condensing a reaction mixture comprising:
at least one phenolic monomer selected from the group consisting of phenol, cresol, resorcinol, xylenol, ethyl phenol, alkyl and alkylresorcinols, and combinations thereof; and
at least one alkyl aldehyde having from 5 to 12 carbon atom alkyl groups.
11. The article of claim 10 , wherein the reaction mixture has a concentration of octylphenol and nonylphenol monomers from 0% to less than 5% by weight of the total weight of phenolic monomers.
12. The article of claim 10 , wherein the condensation reaction is free of formaldehyde.
13. The article of claim 10 , wherein the reaction mixture further comprises formaldehyde.
14. The article of claim 10 , wherein the alkylphenol resin comprises a novolac resin or a resole resin.
15. The article of claim 10 , wherein the reaction mixture further comprises an acid catalyst, a base catalyst, an organic solvent, or combinations thereof.
16. The composition of claim 1 , wherein the organic solvent comprises an aromatic hydrocarbon solvent.
17. The composition of claim 16 , wherein the aromatic hydrocarbon solvent is selected from the group of toluene, xylene, and mixtures thereof.