CN117379329A - Low-water-content N-acyl amino acid salt composition and preparation method thereof - Google Patents

Low-water-content N-acyl amino acid salt composition and preparation method thereof Download PDF

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Publication number
CN117379329A
CN117379329A CN202311134512.2A CN202311134512A CN117379329A CN 117379329 A CN117379329 A CN 117379329A CN 202311134512 A CN202311134512 A CN 202311134512A CN 117379329 A CN117379329 A CN 117379329A
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Prior art keywords
acid
amino acid
salt
acyl amino
water content
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CN202311134512.2A
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Chinese (zh)
Inventor
刘志云
应俊
曾梦婷
陈怀远
宋磊
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Zhejiang Wansheng Co ltd
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Zhejiang Wansheng Co ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0006—Controlling or regulating processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J4/00—Feed or outlet devices; Feed or outlet control devices
    • B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2204/00—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices
    • B01J2204/002—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices the feeding side being of particular interest
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00177—Controlling or regulating processes controlling the pH

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a composition of low-water content N-acyl amino acid salt and a preparation method thereof. The invention provides a composition of N-acyl amino acid salt with low water content and a preparation method thereof, which can shorten the production flow of amino acid surfactant, reduce energy consumption, generate no dust, and simultaneously is easy to dissolve, low in foam and free of dust when in use. The invention combines production and use, not only optimizes the production flow, but also solves the use problem, and has great commercial value.

Description

Low-water-content N-acyl amino acid salt composition and preparation method thereof
Technical Field
The invention relates to a composition of N-acyl amino acid salt with low water content and a preparation method thereof.
Background
Amino acid type surfactants are increasingly valued for their excellent surface properties, and the application fields are also becoming wider. The traditional personal washing and caring products mainly comprise a soap base type product and an AES type product, have strong decontamination capability and are easy to wash, but have great irritation, the skin after washing has a tight feel, and the acid-base balance of the skin can be damaged even a series of skin problems are caused after long-term use. The personal washing and caring product mainly comprising the amino acid type surfactant is slightly acidic and approaches to the pH value of human body, has moderate detergency, good skin-friendly property and low or almost no irritation, and is suitable for various people. Thus, amino acid type products are a major mainstream in personal care products on the market.
In general, when preparing crystalline amino acid personal washing products, the requirements on the activity content are very high, the liquid products with low activity content can not meet the requirements, generally, solid amino acid surfactants with high activity content are used, and the common solid amino acid surfactants in the market are powder, spherical particles, flakes, long strips and the like.
In the production process of the solid amino acid surfactant, liquid products are produced firstly, and then the high-purity solid amino acid surfactant can be obtained through the steps of purification, drying and the like, so that the problems of long process flow, high energy consumption, large dust in production and packaging and the like are solved. Meanwhile, the problems of large dust, difficult dissolution, difficult defoaming and the like exist in the use process.
Disclosure of Invention
Aiming at the technical problems existing in the synthesis and downstream use processes of N-acyl amino acid salt in the prior art, the invention aims to provide a composition of N-acyl amino acid salt with low water content and a preparation method thereof. In the preparation method, in a water phase system, fatty acid chloride and alkali liquor are added dropwise into amino acid or salt water solution thereof at the same time, and a low-water-content compound containing N-acyl amino acid salt is obtained through desalination, purification, neutralization and compounding. In order to achieve the above purpose, the following technical scheme is adopted:
a process for preparing the composition of N-acylamino acid salt with low water content includes such steps as adding fatty acid chloride and alkali solution to the raw materials in aqueous phase, amidating reaction under alkaline condition, desalting, and mixing with polyol.
A method for preparing a low water content N-acyl amino acid salt composition comprising the steps of:
s1: adding amino acid or salt thereof into a reaction kettle, adding water, and adjusting pH to alkaline condition with alkali;
s2: dropwise adding fatty acid chloride into the reaction kettle in a double-dropwise adding mode, adding alkali simultaneously in the reaction process to adjust the pH value to maintain alkalinity until the fatty acid chloride is added completely, and maintaining stirring at a constant temperature until the reaction is finished;
s3: after the reaction is finished, adding acid liquor to adjust the pH of the reaction solution to be acidic, heating to dissolve, standing and layering into an upper oil phase and a lower water phase, cutting off the lower water phase liquid, and washing the upper oil phase;
s4: adding polyalcohol and alkali into the upper oil phase liquid, stirring uniformly, and discharging.
Further, in step S1, the amino acid or a salt thereof is one or more of sarcosine, alanine, valine, leucine, isoleucine, proline, phenylalanine, tryptophan, methionine, glycine, serine, threonine, cysteine, tyrosine, asparagine, glutamine, lysine, arginine, histidine, aspartic acid, glutamic acid or a salt thereof.
Further, in step S2, the fatty acid chloride is obtained by chlorination of fatty acid, and the fatty acid chloride carbon chain is consistent with the fatty acid carbon chain, and the fatty acid carbon chain length is C6-22, including linear or branched, saturated or containing one or multiple double bonds, single fatty acid or mixed acid. The fatty acids include, but are not limited to, C6-C22 saturated fatty acids, oleic acid, linoleic acid, linolenic acid, isooctanoic acid, isostearic acid, coco acid, palmitoleic acid, soy oleic acid, erucic acid, and the like, and can be a mixture of one or more of them in various proportions, preferably C8-C18 fatty acids. The molar ratio of the fatty acid chloride to the amino acid or salt thereof is 1:1.0 to 1.5, preferably 1:1.05-1.36.
Further, in step S1 or S2, the base is at least one of potassium hydroxide, sodium carbonate, potassium carbonate, ammonium hydroxide, monoethanolamine, diethanolamine, and triethanolamine, preferably potassium hydroxide or sodium hydroxide.
Further, the pH is adjusted to 11.0-12.0 in the step S1, and the pH is maintained to 9.0-12.0 in the step S2.
Further, the mass concentration of the amino acid or the salt thereof in the mixed solution of the step S1 is 10% -50%, preferably 13% -30%.
Further, the acid solution in the step S3 includes at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid, hydroiodic acid, hydrobromic acid, preferably hydrochloric acid or sulfuric acid; and step S3, regulating the pH value to be 1.0-3.0, and heating to 90-95 ℃.
Further, the polyol in step S4 is a chemical term, i.e. a large class of alcohols containing two or more hydroxyl groups in the molecule, such as ethylene glycol, propylene glycol, glycerol, butylene glycol, pentaerythritol, etc., and may be a mixture of one or more of them in different proportions, preferably propylene glycol or glycerol.
Further, the polyol is added in the range of 10% to 70%, preferably 30% to 50% by mass of the final product in step S4.
Further, the base in step S4 includes one or more of potassium hydroxide, sodium carbonate, potassium carbonate, ammonium hydroxide, monoethanolamine, diethanolamine, triethanolamine, arginine, and lysine, preferably potassium hydroxide or sodium hydroxide.
The beneficial effects obtained by the invention are as follows:
1) The low-water content N-acyl amino acid salt composition can be well used as personal washing products such as facial cleansing cream, bath lotion and the like.
2) The invention provides a composition of N-acyl amino acid salt with low water content and a preparation method thereof, which can shorten the production flow of amino acid surfactant, reduce energy consumption, generate no dust, and simultaneously is easy to dissolve, low in foam and free of dust when in use. The invention combines production and use, not only optimizes the production flow, but also solves the use problem, and has great commercial value.
Detailed Description
The invention will be further illustrated with reference to specific examples, but the scope of the invention is not limited thereto.
Example preparation of sodium lauroyl sarcosinate Complex
197.1g of sodium sarcosinate water solution with the mass fraction of 35% is weighed into a 1L reaction kettle, 321.7g of deionized water is added, 129.3g of lauroyl chloride and alkaline solution (alkaline solution is 10% NaOH solution) are respectively weighed into a dropping funnel for standby, the dropwise addition of the acyl chloride is started, meanwhile, the pH value is maintained at 9.0-12.0 by the alkaline solution, and the heat preservation reaction is continued for 4 hours after the acyl chloride is completely dropped. HCl is added to lead the pH value to be less than 2, the temperature is raised to 90-95 ℃, the mixture is stood for layering, the lower water phase is cut off, and the upper oil phase is washed with water (the amino acid residue is less than 0.1 percent, the salt content is less than 0.5 percent, and the yield of sodium lauroyl sarcosine is 98 percent). 19.0g of solid sodium hydroxide and 200g of glycerol are added and stirred uniformly, the measured moisture is 6.2%, and the total time is 8 hours.
Example preparation of potassium Dicocoyl glycinate Complex
49.6g glycine is weighed into a 1L reaction kettle, 346.3g pure water is added, the pH value is adjusted to 11.0-12.0 by liquid alkali, 140.2g cocoyl chloride and alkali liquor (alkali liquor is 10% NaOH solution) are respectively weighed into a dropping funnel for standby, the dropwise addition of the acyl chloride is started, meanwhile, the pH value is maintained to 9.0-12.0 by the alkali liquor, and the heat preservation reaction is continued for 4 hours after the acyl chloride is dropwise added. Adding HCl to make pH less than 2, heating to 90-95deg.C, standing for layering, cutting off lower water phase, washing upper oil phase with water (amino acid residue less than 0.1%, salt content less than 0.5%, and yield of potassium cocoyl glycinate 98.5%). 28.0g and 250g of solid potassium hydroxide, glycerol and propylene glycol 1:1, and stirring uniformly, the measured moisture is 7.8%, and the total time is 8 hours.
Example preparation of Tricocoyl alanine TEA salt formulation
68.9g of alanine is weighed into a 1L reaction kettle, 435.0g of pure water is added, the pH value is adjusted to 11.0-12.0 by liquid alkali, 165g of cocoyl chloride and alkali liquor (alkali liquor is 10% NaOH solution) are respectively weighed into a dropping funnel for standby, the dropping of the acyl chloride is started, meanwhile, the pH value is maintained to 9.0-12.0 by the alkali liquor, and the heat preservation reaction is continued for 4 hours after the acyl chloride is dropped. Adding sulfuric acid to make pH less than 2, heating to 90-95deg.C, standing for layering, cutting off lower water phase, washing upper oil phase with water (amino acid residue less than 0.1%, salt content less than 0.5%, and cocoamidopropionic acid yield 98.6%). Triethanolamine 89.0g and 220g glycerol, propylene glycol and butylene glycol 5 were added: 4:1, and the measured moisture is 6.8%, and the total time is 8 hours.
The prepared low-water-content N-acyl amino acid salt is mixed with the polyalcohol and the alkali for compounding, so that the low-water-content N-acyl amino acid salt can be well used as a personal washing product, and the technological operation for preparing the N-acyl amino acid salt can be saved by a simple compound mode.
What has been described in this specification is merely an enumeration of possible forms of implementation for the inventive concept and may not be considered limiting of the scope of the present invention to the specific forms set forth in the examples.

Claims (10)

1. A process for preparing a low water content N-acyl amino acid salt composition comprising the steps of:
s1: adding amino acid or salt thereof into a reaction kettle, adding water, and adjusting pH to alkaline condition with alkali;
s2: dropwise adding fatty acid chloride into the reaction kettle in a double-dropwise adding mode, adding alkali simultaneously in the reaction process to adjust the pH value to maintain alkalinity until the fatty acid chloride is added completely, and maintaining stirring at a constant temperature until the reaction is finished;
s3: after the reaction is finished, adding acid liquor to adjust the pH of the reaction solution to be acidic, heating to dissolve, standing and layering into an upper oil phase and a lower water phase, cutting off the lower water phase liquid, and washing the upper oil phase;
s4: adding polyalcohol and alkali into the upper oil phase liquid, stirring uniformly, and discharging.
2. The method of claim 1, wherein in step S1, the amino acid or salt thereof is one or more of sarcosine, alanine, valine, leucine, isoleucine, proline, phenylalanine, tryptophan, methionine, glycine, serine, threonine, cysteine, tyrosine, asparagine, glutamine, lysine, arginine, histidine, aspartic acid, glutamic acid or a salt thereof.
3. The method of preparing a low water content N-acyl amino acid salt composition according to claim 1, wherein in step S2, the fatty acid chloride is obtained by chlorination of fatty acid, the fatty acid chloride carbon chain is consistent with the fatty acid carbon chain, and the fatty acid carbon chain length is C6-22; the molar ratio of the fatty acid chloride to the amino acid or salt thereof is 1:1.0 to 1.5, preferably 1:1.05-1.36.
4. A process for the preparation of a low water content N-acyl amino acid salt composition according to claim 3 wherein the fatty acid comprises one or more of C6-C22 saturated fatty acids, oleic acid, linoleic acid, linolenic acid, isooctanoic acid, isostearic acid, coco acid, palmitoleic acid, oleic acid, erucic acid, preferably C8-C18 fatty acids.
5. The method of preparing a low water content N-acyl amino acid salt composition according to claim 1, wherein in step S1 or S2, the base is at least one of potassium hydroxide, sodium carbonate, potassium carbonate, ammonium hydroxide, monoethanolamine, diethanolamine, triethanolamine, preferably potassium hydroxide or sodium hydroxide.
6. The method of claim 1, wherein the pH is adjusted to 11.0-12.0 in step S1, and maintained at 9.0-12.0 in step S2.
7. The process for preparing a composition of N-acylamino acid salts having a low water content according to claim 1, characterized in that the mass concentration of the amino acid or its salt in the mixture of step S1 is from 10% to 50%, preferably from 13% to 30%.
8. The process for preparing a composition of low water content N-acyl amino acid salts according to claim 1, wherein the acid solution in step S3 comprises at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid, hydroiodic acid, hydrobromic acid, preferably hydrochloric acid or sulfuric acid; and step S3, regulating the pH value to be 1.0-3.0, and heating to 90-95 ℃.
9. The method of preparing a low water content N-acyl amino acid salt composition according to claim 1, wherein in step S4 the polyol is one or more of ethylene glycol, propylene glycol, glycerol, butylene glycol, pentaerythritol, preferably propylene glycol or glycerol, and the polyol is added in an amount ranging from 10% to 70%, preferably from 30% to 50% by mass of the final product;
the base in step S4 comprises one or more of potassium hydroxide, sodium carbonate, potassium carbonate, ammonium hydroxide, monoethanolamine, diethanolamine, triethanolamine, arginine, lysine, preferably potassium hydroxide or sodium hydroxide.
10. A low moisture N-acyl amino acid salt composition prepared by the method of any one of claims 1-9.
CN202311134512.2A 2023-09-05 2023-09-05 Low-water-content N-acyl amino acid salt composition and preparation method thereof Pending CN117379329A (en)

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CN202311134512.2A CN117379329A (en) 2023-09-05 2023-09-05 Low-water-content N-acyl amino acid salt composition and preparation method thereof

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CN202311134512.2A CN117379329A (en) 2023-09-05 2023-09-05 Low-water-content N-acyl amino acid salt composition and preparation method thereof

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CN117379329A true CN117379329A (en) 2024-01-12

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Inventor after: Liu Zhiyun

Inventor after: Zheng Yizhou

Inventor after: Ying Jun

Inventor after: Zeng Mengting

Inventor after: Chen Huaiyuan

Inventor after: Song Lei

Inventor before: Liu Zhiyun

Inventor before: Ying Jun

Inventor before: Zeng Mengting

Inventor before: Chen Huaiyuan

Inventor before: Song Lei