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- Nachgewiesen in: USPTO Patent Applications
- Sprachen: English
- Document Number: 20200165191
- Publication Date: May 28, 2020
- Appl. No: 16/695231
- Application Filed: November 26, 2019
- Assignees: Kraton Polymers LLC (Houston, TX, US)
- Claim: 1. A method of reducing the aldehyde content of a pine chemical composition, the method comprising: providing an aldehyde scavenger to react with functional —CHO moiety in the aldehydes; treating the pine chemical composition with less than 6 wt % of the aldehyde scavenger to form an aldehyde-aldehyde scavenger reaction product; optionally removing the formed aldehyde-aldehyde scavenger reaction product from the treated pine chemical composition to obtain a purified pine chemical composition; wherein the aldehyde scavenger is an aromatic primary amine derivative selected from: a) an arylamine comprising an —NH2 group and an ortho-carboxamide, b) an arylamine comprising an —NH2 group and an ortho-sulfonamide substituent, and c) an arylsulfonylhydrazide, wherein the aromatic primary amine derivative has a molecular weight less than 1000 g/mol, and comprises at least 4 elements in its molecular formula selected from the group of C, H, O, S, N, Cl, F, Br, I, B, Si and P, wherein the pine chemical composition is selected from the group consisting of gum turpentine, gum rosin, crude sulfate turpentine (CST), BLS black liquor soap, crude tall oil (CTO), depitched CTO, distilled tall oil (DTO), tall oil head (TOH), tall oil rosin (TOR), tall oil pitch (TOP), tall oil fatty acids (TOFA), fractionated TOFA, TOFA dimer, TOFA trimer, TOFA monomer, isostearic acid, stearic acid, and ester- and amide derivatives thereof.
- Claim: 2. The method of claim 1, wherein the aromatic primary amine derivative is unsubstituted or substituted with 1-3 substituents selected from the group consisting of methyl, ethyl, tert-butyl, methoxy, ethoxy, 1-methyl ethoxy, cyclopropyloxy, isopropyl, phenylmethoxy, fluoro, chloro, bromo, iodo, trifluoromethyl, trifluoromethoxy, 4-methyl-1-piperazinyl, 3-(4-morpholinyl)propoxy, carbamoyl, nitro, amino, cyano, hydroxyl, dimethylamino, sulfamoyl, 1-piperidinyl, 1-pyrrolidinyl, 4-morpholinyl, aminosulfonyl, acetyl, carboxyl, carbomethoxy, and any combinations thereof.
- Claim: 3. The method of claim 1, wherein the arylamine comprising an —NH2 group and an ortho-carboxamide or an ortho-sulfonamide substituent, and the arylsulfonylhydrazide, are optionally substituted with one or two substituents selected from the group consisting of methyl, ethyl, methoxy, fluoro, chloro, bromo, iodo, carbamoyl, nitro, amino, cyano, acetyl, carbomethoxy, sulfamoyl, and any combinations thereof.
- Claim: 4. The method of any of claim 1, wherein the aryl group in the aromatic primary amine derivative represents a phenyl group.
- Claim: 5. The method of claim 1, wherein the aldehyde scavenger is selected from the group consisting of anthranilamide, 2-aminobenzenesulfonamide, 4-amino-6-chloro-1,3-benzenedisulfonamide, 2-amino-5-bromo-benzenesulfonamide, 2-amino-5-chloro-benzenesulfonamide, 2-amino-5-methyl-benzenesulfonamide, 2,5-diamino-benzenesulfonamide, 2-amino-5-fluoro-benzenesulfonamide, 2-amino-4-chloro-benzenesulfonamide, 2-amino-4-bromo-benzenesulfonamide, 2-amino-4-methoxy-benzenesulfonamide, benzenesulfonyl hydrazide, para-toluenesulfonyl hydrazide, 2,4,6-triisopropylbenzenesulfonyl hydrazide, 2,4,6-trimethylbenzenesulfonyl hydrazide, 4-methoxybenzenesulfonyl hydrazide, 4-ethoxybenzenesulfonyl hydrazide, 4-bromobenzenesulfonyl hydrazide, 4-chlorobenzenesulfonyl hydrazide, 4-fluorobenzenesulfonyl hydrazide, 2-naphthalenesulfonyl hydrazide, 2,4-dichlorobenzenesulfonyl hydrazide, 2,5-dimethylbenzenesulfonyl hydrazide, 3-amino-2-pyridinecarboxamide, 3-amino-4-pyridinecarboxamide, 2-amino-3-pyridinecarboxamide, 3-amino-2-pyridinesulfonamide, 3-amino-4-pyridinesulfonamide, 2-amino-3-pyridinesulfonamide, and derivatives of 2-aminobenzamide wherein the phenyl ring contains 1-3 additional substituents selected from the group consisting of methyl, ethyl, tert-butyl, methoxy, ethoxy, 1-methylethoxy, cyclopropyloxy, phenylmethoxy, fluoro, chloro, bromo, iodo, trifluoromethyl, trifluoromethoxy, 4-methyl-1-piperazinyl, 3-(4-morpholinyl)propoxy, carbamoyl, nitro, amino, cyano, hydroxyl, dimethylamino, sulfamoyl, 1-piperidinyl, 1-pyrrolidinyl, 4-morpholinyl, aminosulfonyl, acetyl, carboxyl, carbomethoxy, and any combinations thereof.
- Claim: 6. The method of claim 1, wherein at least 50% of the aldehydes is removed from the pine chemical composition.
- Claim: 7. The method of claim 1, wherein the aldehydes initially present in the pine chemical composition comprises C20 resin aldehydes, and wherein the C20 resin aldehydes content is reduced at least 80% after treatment.
- Claim: 8. The method of claim 1, wherein the treatment of the pine chemical composition with the aldehyde scavenger is at a temperature of 120-250° C.
- Claim: 9. The method of claim 1, wherein the aldehyde scavenger is anthranilamide.
- Claim: 10. The method of claim 1, wherein the pine chemical composition is treated with 0.01-3 wt % of an aldehyde scavenger.
- Claim: 11. The method of claim 1, wherein the wherein the pine chemical composition is treated with 0.01-3 wt % anthranilamide.
- Claim: 12. The method of claim 1, wherein the pine chemical composition is one or more selected from the group consisting of BLS, CTO, depitched CTO, DTO, TOFA, TOFA dimer, TOFA trimer, TOFA monomer, isostearic acid, stearic acid, and ester- and amide derivatives thereof.
- Claim: 13. The method of claim 1, wherein the formed aldehyde-aldehyde scavenger reaction product removal from the treated pine chemical composition to obtain a purified pine chemical composition comprises distillation under reduced pressure, wherein the formed aldehyde-aldehyde scavenger reaction product remains in the distillation residue fraction.
- Claim: 14. A pine chemical composition prepared by the method of claim 1, wherein the pine chemical composition contains an aldehyde-aldehyde scavenger reaction product in an amount of between 0.01 wt. % and 10 wt %.
- Claim: 15. A pine chemical composition prepared by the method of claim 1, wherein the aldehyde content is less than 1200 ppm.
- Claim: 16. A method of reducing the aldehyde content of a pine chemical composition, the method comprising: treating the pine chemical composition with less than 6 wt % of anthranilamide at a temperature between 50° C. to about 250° C., for 5 minutes to 24 hours; wherein at least 50% of the aldehydes is removed from the pine chemical composition, and wherein the pine chemical composition is selected from the group consisting of gum turpentine, gum rosin, CST, BLS, CTO, depitched CTO, DTO, TOH, TOR, TOP, TOFA, fractionated TOFA, TOFA dimer, TOFA trimer, TOFA monomer, isostearic acid, stearic acid, and ester- and amide derivatives thereof.
- Claim: 17. The method of claim 16, wherein the aldehydes initially present in the pine chemical composition comprises C20 resin aldehydes, wherein the C20 resin aldehydes content is reduced at least 80% after treatment, and wherein the pine chemical composition is selected from the group consisting of BLS, CTO, depitched CTO, DTO, TOFA, TOFA dimer, TOFA trimer, TOFA monomer, isostearic acid, stearic acid, and any combinations thereof.
- Claim: 18. A pine chemical composition prepared by the method of claim 16, wherein the pine chemical composition contains an aldehyde-anthranilamide reaction product in an amount of between 0.01 wt. % and 10 wt %.
- Claim: 19. A pine chemical composition prepared by the method of claim 16, wherein the aldehyde content is less than 500 ppm.
- Claim: 20. A pine chemical composition prepared by the method of claim 16, wherein the aldehyde content is less than 100 ppm.
- Current International Class: 07; 07
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