阅读说明：本技术 烷氧基化酯胺及其盐 (Alkoxylated esteramines and salts thereof ) 是由 B·卢多尔夫 S·艾伯特 C·比特纳 于 2018-06-26 设计创作，主要内容包括：本发明涉及式(I)的烷氧基化酯胺及其盐。根据本发明的酯胺可以用于清洁组合物，例如用于液体衣物洗涤剂。例如当在冷水洗涤条件下使用时，它们导致所述组合物的清洁性能改进。它们令人惊奇地提高了液体衣物洗涤剂的油脂清洁性能，尤其是在冷水洗涤条件下。还改进了白度。根据本发明的酯胺在液体衣物洗涤剂配制剂中显示出改进相容性。<Image he="756" wi="700" file="DDA0002344578840000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention relates to alkoxy of formula (I)Esterified esteramines and salts thereof. The esteramines according to the invention can be used in cleaning compositions, for example in liquid laundry detergents. For example, they result in improved cleaning performance of the composition when used under cold water wash conditions. They surprisingly improve the grease cleaning performance of liquid laundry detergents, especially under cold water wash conditions. The whiteness is also improved. The esteramines according to the invention show improved compatibility in liquid laundry detergent formulations.)

1. Esteramines of the formula (I) and their salts,

wherein independently of each other

n is an integer of 1 to 12,

m is independently selected for each repeating unit n from an integer of 0 to 12;

p is an integer of 0 to 12,

o is independently selected for each repeating unit p from an integer of 0 to 12;

r is an integer of 0 to 12,

q is independently selected for each repeat unit r from an integer of 0 to 12;

s is an integer from 0 to 100;

t is an integer from 1 to 100;

u is an integer of 0 to 100;

v is an integer from 0 to 100;

wherein the sum of s, t, u and v is equal to or greater than 1;

A₁、A₂、A₃and A₄Independently of each other and for each repeating unit s, t, u or v is independently selected from the list consisting of: ethyleneoxy, 1, 2-propyleneoxy, 1, 2-butyleneoxy, 2, 3-butyleneoxy, isobutyleneoxy, pentyleneoxy, hexyleneoxy, styryloxy, decenyloxy, dodecenyloxy, tetradecenyloxy and hexadecyloxy, where for s, t, u and/or v equal to 1, the radical A₁、A₂、A₃And A₄Is bonded to the group B, and the subsequent group A₁、A₂、A₃And A₄Always through an oxygen atom withThe former group A₁、A₂、A₃And A₄Bonding;

B₁、B₂、B₃and B₄Independently of each other selected from the group consisting of: bond, straight chain C₁To C₁₂Alkanediyl and branching C₁To C₁₂An alkanediyl group;

R₄、R₈and R₁₂Selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

R₁、R₂and R₃Each repeat unit m for each repeat unit n is independently selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

R₅、R₆and R₇Each repeat unit o for each repeat unit p is independently selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

R₉、R₁₀and R₁₁Each repeat unit q for each repeat unit r is independently selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

i) provided that when p and r are both equal to 0 and n is at least 1, Z₁And Z₂Independently selected from the group consisting of: OH, alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine and a compound according to formula (II), wherein said compound according to formula (II) is linked to a compound according to formula (I) by a bond marked with [, with the proviso that at least one substituent Z₁And/or Z₂Is not OH, and provided that R₃Containing 2 or more carbon atoms;

wherein independently of each other

w is an integer of 0 to 12;

R₁₃and R₁₄For each repeating unit w is independently selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

R₁₅、R₁₆、R₁₇and R₁₈Selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

ii) with the proviso that when n and p are independently equal to or greater than 1 and r is equal to or greater than 0, Z₁And/or Z₂And/or Z₃And/or Z₄N, p and r are independently selected for each repeating unit from the group consisting of: OH, alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine and a compound according to formula (II), wherein said compound according to formula (II) is linked to a compound according to formula (I) by a bond marked with [, with the proviso that at least one substituent Z₁And/or Z₂And/or Z₃And/or Z₄Is not OH, and wherein for n and p equal to 1 and r equal to 0, at least one unit A₁、A₂Or A₃Selected from the group consisting of: 1, 2-propyleneoxy, 1, 2-butyleneoxy, 2, 3-butyleneoxy, isobutyleneoxy, pentyleneoxy, hexyleneoxy, styryloxy, decenyloxy, dodecenyloxy, tetradecenyloxy and hexadecyloxy.

2. The salt of an esteramine according to claim 1 wherein the salt is formed by at least partially protonating the amine groups with an acid that is a protic organic or inorganic acid.

3. The salt of an esteramine according to claim 1 or 2 wherein the salt is formed by at least partially protonating an amine group with an acid selected from the group consisting of: methanesulfonic acid, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, citric acid and lactic acid.

4. The esteramine or salt thereof according to any one of the preceding claims, wherein a₁、A₂、A₃And A₄Independently of each other and for each repeating unit s, t, u or v is independently selected from the list consisting of: ethyleneoxy, 1, 2-propyleneoxy and 1, 2-butyleneoxy.

5. The esteramine or salt thereof according to any one of the preceding claims 1-4 wherein p and r are both equal to 0 and n is at least 1, Z₁And Z₂Independently selected from the group consisting of: OH, alanine, glycine, lysine and compounds according to formula (II) wherein w is an integer from 1 to 4, wherein the compound according to formula (II) is linked to the compound according to formula (I) by a bond marked with x, with the proviso that at least one substituent Z₁And/or Z₂Is not OH, and provided that R₃Containing equal to or greater than 2 carbon atoms.

6. The esteramine or salt thereof according to any one of the preceding claims 1-4 wherein p and R are both equal to 0 and n is at least 1, wherein m is equal to 1 and R is₁And R₂Are all straight chain C₂To C₄An alkyl group.

7. The esteramine or salt thereof according to any one of the preceding claims 1-4, wherein Z is when n and p are independently equal to or greater than 1 and r is equal to or greater than 0₁And/or Z₂And/or Z₃And/or Z₄N, p and r are independently selected for each repeating unit from the group consisting of: OH, alanine, glycine, lysine and compounds according to formula (II) wherein w is an integer from 1 to 4, wherein the compound according to formula (II) is linked to the compound according to formula (I) by a bond marked with x, with the proviso that at least one substituent Z₁And/or Z₂And/or Z₃And/or Z₄Is not OH.

8. The esteramine or salt thereof according to any one of the preceding claims 1 to 4 wherein n and p are equalAt 1, R equals 0, m and o equal 0, B1 equals a bond, R₃、R₄、R₇、R₈And R₁₂Are all equal to H.

9. The esteramine or salt thereof according to any one of the preceding claims 1 to 4 wherein n and p are both equal to 1, R is equal to 0, m and o are both equal to 0, B1 is equal to methylene, R is₃、R₄、R₇And R₈Are all equal to H, and R₁₂Equal to ethyl.

10. A process for preparing the esteramine or salt thereof according to claim 1, comprising the steps of:

a) reacting an alcohol according to formula (III) with one or more C₂-C₁₆And (3) alkylene oxide reaction:

wherein independently of each other

n is an integer of 1 to 12,

m is independently selected for each repeating unit n from an integer of 0 to 12;

p is an integer of 0 to 12,

o is independently selected for each repeating unit p from an integer of 0 to 12;

r is an integer of 0 to 12,

q is independently selected for each repeat unit r from an integer of 0 to 12;

B₁、B₂、B₃and B₄Independently of each other selected from the group consisting of: bond, straight chain C₁To C₁₂Alkanediyl and branching C₁To C₁₂An alkanediyl group;

R₄、R₈and R₁₂Selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

R₁、R₂and R₃Each repeat unit m for each repeat unit n is independently selected from the group consisting of: h, straight chain alkyl, branched alkyl and cyclicAn alkyl group;

R₅、R₆and R₇Each repeat unit o for each repeat unit p is independently selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

R₉、R₁₀and R₁₁Each repeat unit q for each repeat unit r is independently selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl; then the

b) At least partially esterifying the alkoxylated alcohol with at least one compound selected from the group consisting of: alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, acids according to formula (IV) and salts thereof,

wherein w is an integer from 0 to 12;

R₁₃and R₁₄For each repeating unit w is independently selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl;

R₁₅、R₁₆、R₁₇and R₁₈Selected from the group consisting of: h, straight chain alkyl, branched alkyl and cycloalkyl.

11. The process according to claim 10, wherein the alcohol according to formula (III) is reacted with total C₂-C₁₂The molar ratio of alkylene oxide is 1:1 to 1: 400.

12. The process according to claim 10 or 11, wherein the molar ratio of acid to hydroxyl groups of the alkoxylated alcohol is from 0.1:1 to 1:1.

13. Use of esteramines and salts thereof according to claims 1 to 9 in personal care, as curing agents for epoxy resins, as reactants in the production of polymers, in polyurethanes, polyureas or as thermoplastic polyamide adhesives.

14. Use of esteramines and salts thereof according to claim 13 in shampoo or body wash formulations.

15. A personal care composition comprising the esteramine of any one of claims 1-9 and salts thereof.

Examples

Comparative example 1: methanesulfonic acid salt of ester of butyltriglycol ether with 6-aminocaproic acid

In a 4-necked flask with a thermometer, reflux condenser, nitrogen inlet, dropping funnel and stirrer, 64.39g of butyltriglycol ether and 39.35g of 6-aminocaproic acid were placed and heated to 90 ℃. To the mixture was added 29.4g of methanesulfonic acid over 10 minutes. The reaction mixture was heated to 135 ℃ and stirred at 135 ℃ for 4 hours. Vacuum (5 mbar) was applied and the reaction mixture was stirred at 130 ℃ for a further 13.5 hours. 122.0g of a light brown solid is obtained. In MeOD¹H-NMR showed complete conversion to 6-aminocaproic acid-butyl triethylene glycol ether ester in the mesylate salt form.

Comparative example 2: m_wMesylate salt of an ester of polyethylene glycol and 6-aminocaproic acid at about 200g/mol

Into a 4-necked flask having a thermometer, a reflux condenser, a nitrogen inlet, a dropping funnel and a stirrer was placed 30.0g of polyethylene glycol (M)_wIs about 200g/mol) and 39.35g of 6-aminocaproic acid and heating to 90 ℃. To the mixture was added 29.4g of methanesulfonic acid over 10 minutes. The reaction mixture was heated to 135 ℃ and stirred at 135 ℃ for 4 hours. Vacuum (5 mbar) was applied and the reaction mixture was stirred at 135 ℃ for a further 22 hours. 97.0g of a light brown solid is obtained. In MeOD¹H-NMR showed complete conversion to 6-aminocaproic acid-polyethylene glycol ester in the mesylate salt form.