阅读说明：本技术 氨基酸酯的有机磺酸盐及其制备方法 (Organic sulfonate of amino acid ester and preparation method thereof ) 是由 S·艾伯特 B·卢多尔夫 D·马克兹维斯基 于 2018-11-27 设计创作，主要内容包括：本发明涉及一种合成氨基酸酯的有机磺酸盐的方法,包括如下步骤：(i)使至少一种在内酰胺环中具有至少3个碳原子的内酰胺与至少一种有机磺酸在水溶液中反应,(ii)用至少一种包含至少一个羟基的具有至少8个碳原子的醇酯化步骤(i)的有机磺酸氨基酸盐,(iii)任选地,除去水和/或除去步骤(ii)的过量醇。本发明还涉及通式(I)的氨基酸酯的有机磺酸盐。<Image he="548" wi="681" file="DDA0002521863720000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention relates to a method for synthesizing organic sulfonate of amino acid ester, which comprises the following steps: (i) reacting at least one lactam having at least 3 carbon atoms in the lactam ring with at least one organic sulfonic acid in aqueous solution, (ii) esterifying the organic sulfonic acid amino acid salt of step (i) with at least one alcohol having at least 8 carbon atoms comprising at least one hydroxyl group, (iii) optionally, removing water and/or removing excess alcohol of step (ii). The invention also relates to organic sulfonic acid salts of amino acid esters of the general formula (I).)

1. A method for synthesizing an organic sulfonate of an amino acid ester comprising the steps of:

(i) reacting at least one lactam having at least 3 carbon atoms in the lactam ring with at least one organic sulfonic acid in an aqueous solution,

(ii) (ii) esterifying the reaction product of step (i) with at least one alcohol having at least 8 carbon atoms comprising at least one hydroxyl group,

(iii) optionally, removing water and/or removing excess alcohol of step (ii).

2. The method according to claim 1, wherein steps (i) and (ii) are performed in one single step.

3. A process according to any one of the preceding claims wherein the molar ratio of organic sulphonic acid to lactam is in the range 90 to 200 mol%.

4. The process according to claim 2, wherein the combining of steps (i) and (ii) comprises reacting an organosulfonic acid, at least one lactam having at least 3 carbon atoms in the lactam ring, and at least one linear or branched C comprising at least one hydroxyl group₈-C₃₆The mixture of alcohols is reacted at a temperature of 80-200 ℃ for 1-30 hours.

5. A process according to any preceding claim wherein the molar ratio of organic sulphonic acid amino acid salt to hydroxyl groups of step (i) is in the range 50 to 125 mol% where a monohydric alcohol is used in step (ii).

6. The process according to any one of claims 1 to 5, wherein the molar ratio of the organic sulfonic acid amino acid salt to the hydroxyl groups of step (i) is in the range of from 10 to 125 mol% in the case of using a diol or polyol in step (ii).

7. A process according to any preceding claim wherein the alcohol used in step (ii) is selected from monohydric alcohols, diols, polyols, alkoxylated monohydric alcohols, alkoxylated diols and alkoxylated polyols.

8. A process according to any one of the preceding claims wherein the lactam used in step (i) is a-lactam.

9. A process according to any preceding claim wherein the organic sulphonic acid is selected from dodecylbenzenesulphonic acid, p-toluenesulphonic acid, xylenesulphonic acid and methanesulphonic acid.

10. A process according to any one of the preceding claims wherein the organic sulphonic acid is methanesulphonic acid.

11. An organic sulfonate of an amino acid ester of formula (I):

wherein R1 is selected from the group consisting of methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene and decylene,

wherein R2 is H or C₁-C₁₂An alkyl group, a carboxyl group,

wherein R3 is a linear or branched alkyl group having at least 8 carbon atoms which is unmodified or modified with one or more hydroxyl groups, or a linear or branched ether alkyl group having at least 8 carbon atoms which is unmodified or modified with one or more hydroxyl groups,

wherein R4 is selected from C₃-C₃₀Alkyl, phenyl, phenoxyalkyl, alkylaryl other than toluyl, C having at least one double bond in the alkylene chain₃-C₃₀Alkenyl groups, camphor groups and mixtures thereof.

12. The organic sulfonate of an amino acid ester according to claim 11 wherein R4 is a substituted phenyl group of formula (II):

wherein the bond marked with x represents the bond linking the group to the sulfur atom, and

wherein R5, R6, R7, R8 and R9 are each independently selected from hydrogen and linear and branched C₁-C₂₀Alkyl, excluding the option that one of R5-R9 is methyl, while the remaining groups are all hydrogen.

13. The organic sulfonic acid salt of an amino acid ester according to claim 12 wherein one of R5, R6, R7, R8 and R9 is linear or branched C₁₁Alkyl and the remaining substituents are hydrogen.

Examples

Method of producing a composite material

Using a Bruker Avance 400MHz spectrometerMeasurement in MeOD¹H NMR。