CN110981759A - Preparation method of N-acyl-N-methyltaurate and application of N-acyl-N-methyltaurate in silicone oil-free shampoo - Google Patents
Preparation method of N-acyl-N-methyltaurate and application of N-acyl-N-methyltaurate in silicone oil-free shampoo Download PDFInfo
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- CN110981759A CN110981759A CN201911262103.4A CN201911262103A CN110981759A CN 110981759 A CN110981759 A CN 110981759A CN 201911262103 A CN201911262103 A CN 201911262103A CN 110981759 A CN110981759 A CN 110981759A
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- methyltaurate
- acyl
- chloride
- methyl taurate
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- 239000002453 shampoo Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 14
- 229940104261 taurate Drugs 0.000 claims abstract description 85
- -1 methyl taurate Chemical compound 0.000 claims abstract description 69
- 239000000243 solution Substances 0.000 claims abstract description 51
- 239000007864 aqueous solution Substances 0.000 claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 239000011259 mixed solution Substances 0.000 claims abstract description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 87
- 150000002190 fatty acyls Chemical group 0.000 claims description 80
- 239000007788 liquid Substances 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 29
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 29
- KKDONKAYVYTWGY-UHFFFAOYSA-M sodium;2-(methylamino)ethanesulfonate Chemical compound [Na+].CNCCS([O-])(=O)=O KKDONKAYVYTWGY-UHFFFAOYSA-M 0.000 claims description 19
- 239000003513 alkali Substances 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000002033 PVDF binder Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical group CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 claims description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 5
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 5
- WTXXSZUATXIAJO-OWBHPGMISA-N (Z)-14-methylpentadec-2-enoic acid Chemical compound CC(CCCCCCCCCC\C=C/C(=O)O)C WTXXSZUATXIAJO-OWBHPGMISA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012535 impurity Substances 0.000 abstract description 12
- 239000004094 surface-active agent Substances 0.000 abstract description 9
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- 238000006460 hydrolysis reaction Methods 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 7
- 230000007062 hydrolysis Effects 0.000 abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract description 4
- 125000002252 acyl group Chemical group 0.000 abstract description 3
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- 238000012360 testing method Methods 0.000 description 22
- 239000012266 salt solution Substances 0.000 description 11
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- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical class CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
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- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
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- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- TWMBOHVOMWFMJI-UHFFFAOYSA-N 2-hydroxyethyl phosphono hydrogen phosphate Chemical compound OCCOP(O)(=O)OP(O)(O)=O TWMBOHVOMWFMJI-UHFFFAOYSA-N 0.000 description 1
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- VFKZECOCJCGZQK-UHFFFAOYSA-M 3-hydroxypropyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCO VFKZECOCJCGZQK-UHFFFAOYSA-M 0.000 description 1
- LXAHHHIGZXPRKQ-UHFFFAOYSA-N 5-fluoro-2-methylpyridine Chemical compound CC1=CC=C(F)C=N1 LXAHHHIGZXPRKQ-UHFFFAOYSA-N 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
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- 108010022355 Fibroins Proteins 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- RFJHCAHSOWEFNE-UHFFFAOYSA-N benzyl(chloro)phosphane Chemical compound ClPCC1=CC=CC=C1 RFJHCAHSOWEFNE-UHFFFAOYSA-N 0.000 description 1
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
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- 229930182478 glucoside Natural products 0.000 description 1
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- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
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- 230000035515 penetration Effects 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical class 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- 229940045944 sodium lauroyl glutamate Drugs 0.000 description 1
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 description 1
- GOJYXPWOUJYXJC-UHFFFAOYSA-M sodium;2-[1-(2-hydroxyethyl)-2-undecyl-4,5-dihydroimidazol-1-ium-1-yl]acetate;hydroxide Chemical compound [OH-].[Na+].CCCCCCCCCCCC1=NCC[N+]1(CCO)CC([O-])=O GOJYXPWOUJYXJC-UHFFFAOYSA-M 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- 229940011671 vitamin b6 Drugs 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/002—Preparations for repairing the hair, e.g. hair cure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
- A61K2800/34—Free of silicones
Abstract
The preparation method of the N-acyl-N-methyltaurate and the application of the N-acyl-N-methyltaurate in the silicone-oil-free shampoo have the advantages that the initial temperature in the preparation method is higher, the methyl taurate solution and the fatty acyl chloride are synchronously dripped in the same proportion from beginning to end, the local over-high concentration of the fatty acyl chloride is avoided, the hydrolysis degree of the fatty acyl chloride is reduced, and the generation of impurities can be reduced; in addition, the high initial reaction temperature enables the viscosity of the mixed solution of the methyl taurate solution with high concentration and the fatty acyl chloride to be still small, and the mixed solution is easy to flow and mix, so that the production of the N-acyl-N-methyl taurate surfactant with high content becomes easy to realize; the preparation process for preparing the acyl methyl taurate surfactant aqueous solution with the active substance content of more than 40 percent is simple; the silicone oil-free shampoo has low irritation to human bodies, and can make hair mild, moist and smooth after being used.
Description
Technical Field
The invention belongs to the technical field of surfactants, and particularly relates to N-acyl-N-methyltaurate, in particular to a preparation method of the N-acyl-N-methyltaurate and application of the N-acyl-N-methyltaurate in silicone oil-free shampoo.
Background
N-acyl-N-methyltaurates were originally developed as surfactants for the fiber industry, which have both the characteristics of common anionic surfactants and the characteristics of soaps, are relatively stable in acidic, alkaline and oxidizing agent solutions, and have excellent detergency, penetration and emulsifying properties.
The most industrially used method for preparing N-acylamino acids and salts thereof at present still uses the Schottky-Banmann condensation reaction method, which is to prepare N-acylamino acid salts from fatty acyl chloride and amino acid in one step in an alkaline aqueous solution or other organic solvents. The method has the advantages of uncomplicated process flow and equipment, easily obtained raw materials, mild condensation reaction conditions, low reaction temperature and easy realization of industrial production. The Schotten-Banmann reaction is a process for the condensation of fatty acid chlorides and amino acids which is widely used industrially and is subject to constant improvement. The improvement condition of the existing preparation process of N-acyl-N-methyltaurate can be summarized as that a method of alternatively or synchronously dripping fatty acyl chloride and liquid alkali into a methyl taurate solution is adopted, and the reaction temperature is controlled to be lower than 40 ℃, and the main reasons are two aspects, namely, the density of the fatty acyl chloride and the methyl taurate solution is greatly different, the density of the fatty acyl chloride is about 0.9g/ml, the density of the 40% methyl taurate solution is about 1.2g/ml, and the compatibility of the fatty acyl chloride and the methyl taurate solution is extremely poor, so that the local concentration of the fatty acyl chloride is overhigh; secondly, the hydrolysis reaction of fatty acyl chloride exists at the same time, and the hydrolysis rate is increased along with the increase of the temperature. The current process conditions aim to avoid excessive hydrolysis of fatty acyl chloride, reduce impurities and improve the conversion rate. The synthesis process of dripping fatty acyl chloride is adopted, and in actual operation, rapid stirring is necessary to be assisted so that the fatty acyl chloride is dispersed into the methyl taurine salt solution as soon as possible, but when a product with the content of N-acyl-N-methyl taurate active substances exceeding 40% is produced, when the fatty acyl chloride is dripped to a certain proportion, feed liquid becomes sticky and is difficult to mix uniformly, a large amount of bubbles are easily generated under rapid stirring, the dispersion of the fatty acyl chloride into the methyl taurine salt solution is hindered, the conversion rate is low, and the impurity content is increased.
Disclosure of Invention
Based on the technical problems of low conversion rate and increased impurity content when the product with the N-acyl-N-methyltaurate active matter content exceeding 40% is produced, the invention provides a preparation method of N-acyl-N-methyltaurate and application of the N-acyl-N-methyltaurate in silicone oil-free shampoo.
The preparation method of the N-acyl-N-methyl taurate comprises the following steps:
s1, selecting a methyl taurate aqueous solution, fatty acyl chloride and liquid alkali as raw materials;
s2, preheating a methyl taurate aqueous solution to 40-70 ℃;
s3, respectively placing the methyl taurate aqueous solution and the fatty acyl chloride in a first elevated tank and a second elevated tank, synchronously dropwise adding the methyl taurate aqueous solution and the fatty acyl chloride into a section of inclined spiral pipeline, and mixing the methyl taurate aqueous solution and the fatty acyl chloride through the spiral pipeline;
s4, placing the liquid caustic soda in another third elevated tank, and synchronously dropwise adding the liquid caustic soda and the mixed liquid of the methyl taurate aqueous solution and the fatty acyl chloride in the S3, wherein the liquid caustic soda, the methyl taurate aqueous solution and the fatty acyl chloride synchronously enter the tail end of the spiral pipeline to be mixed;
s5, feeding the mixed solution of the three into a main reaction kettle, reacting for 1-3 h, and setting the temperature of the main reaction kettle to be 60-80 ℃.
In one embodiment, the molar ratio of fatty acid chloride, methyl taurate and liquid base is 1: 1.0-1.3: 0.9 to 1.1.
In one embodiment, the mass percentage of the methyl taurate in the methyl taurate aqueous solution is 25% -40%.
In one embodiment, the fatty acid chloride is caprylyl chloride, lauroyl chloride, C12～18Cocoyl chloride or C12～18One of cocoyl chloride.
In one embodiment, the methyltaurate is one of sodium methyltaurate or potassium methyltaurate.
In one embodiment, the dropping speeds of the methyl taurate aqueous solution, the fatty acyl chloride and the liquid alkali are respectively 13kg/min to 22kg/min, 7kg/min to 10kg/min and 4kg/min to 6 kg/min.
In one embodiment, the spiral pipe is one of non-metal pipes such as a PE pipe, a PP pipe, a PVC pipe, a PPR pipe, a PTFE pipe, and a PVDF pipe.
In one embodiment, the pipe diameter of the spiral pipe is DN 25-DN 80.
In one embodiment, the length of the spiral pipeline is 1-10 m, and the inclination angle is 10-60 degrees.
The invention also provides application of the N-acyl-N-methyltaurine salt obtained by the preparation method of the N-acyl-N-methyltaurine salt to silicone oil-free shampoo.
The preparation method of the N-acyl-N-methyl taurate and the application of the N-acyl-N-methyl taurate in the silicone oil-free shampoo have the beneficial effects that:
1. the higher initial reaction temperature ensures that the viscosity of the mixed solution of the methyl taurate solution with high concentration and the fatty acyl chloride is still lower, and the mixed solution is easy to flow and mix, thereby the production of the N-acyl-N-methyl taurate surfactant with high content is easy to realize;
2. the methyl taurate solution and the fatty acyl chloride are mixed in advance and then are dripped into the reaction kettle synchronously with the liquid caustic soda, so that the reaction is ensured to be completed as soon as possible, the problem that the local concentration of the fatty acyl chloride is too high and the fatty acyl chloride is excessively hydrolyzed at high temperature in the conventional process is avoided, and the generation of impurities is reduced.
3. The preparation process is simple, and the industrial production is easy to realize;
the N-acyl-N-methyltaurate is an anionic surfactant with high safety, has excellent foamability, water solubility and hard water resistance, is applied to the silicone-free shampoo, has low irritation to human bodies, and can make hair mild, moist and smooth after being used.
Drawings
FIG. 1 is a schematic diagram of an apparatus for producing N-acyl-N-methyltaurate.
FIG. 2 is a statistical chart of the data measured in experiment 2.
Detailed Description
The embodiments in the description are only for illustrating the present invention and do not limit the scope of the present invention. The scope of the present invention is defined only by the appended claims, and any omissions, substitutions, or modifications made based on the embodiments disclosed herein will fall within the scope of the present invention.
The disclosure may be understood more readily by reference to the following detailed description of preferred embodiments of the invention and the examples included therein. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification, including definitions, will control.
The term "prepared from …" as used herein is synonymous with "comprising". The terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
In addition, the indefinite articles "a" and "an" preceding an element or component of the invention are not intended to limit the number requirement (i.e., the number of occurrences) of the element or component. Thus, "a" or "an" should be read to include one or at least one, and the singular form of an element or component also includes the plural unless the stated number clearly indicates that the singular form is intended.
For the purpose of enhancing understanding of the present invention, the present invention will be further described in detail with reference to the following examples, which are provided for illustration only and are not to be construed as limiting the scope of the present invention.
The preparation method of the N-acyl-N-methyl taurate is characterized by comprising the following steps: s1, selecting a methyl taurate aqueous solution, fatty acyl chloride and liquid alkali as raw materials; s2, preheating a methyl taurate aqueous solution to 40-70 ℃; s3, respectively placing the methyl taurate aqueous solution and the fatty acyl chloride into the first elevated tank 10 and the second elevated tank 20, synchronously dropwise adding the methyl taurate aqueous solution and the fatty acyl chloride into a section of inclined spiral pipeline 40, and mixing the methyl taurate aqueous solution and the fatty acyl chloride through the spiral pipeline 40; s4, placing the liquid caustic soda in another third elevated tank 30, and synchronously dropwise adding the liquid caustic soda and the mixed liquid of the methyl taurate aqueous solution and the fatty acyl chloride in the S3, wherein the liquid caustic soda, the methyl taurate aqueous solution and the fatty acyl chloride synchronously enter the tail end of the spiral pipeline 40 to be mixed; s5, feeding the mixed solution of the three into the main reaction kettle 50, reacting for 1-3 h, and setting the temperature of the main reaction kettle 50 at 60-80 ℃.
The preparation method of the N-acyl-N-methyl taurate is used for producing acyl methyl taurate surfactant aqueous solution with the active substance content of more than 40%, and methyl taurate aqueous solution, fatty acyl chloride and liquid alkali are selected as raw materials. Wherein, the methyl taurate aqueous solution and the fatty acyl chloride are polymerized under the alkaline condition to generate the N-acyl-N-methyl taurate.
The conventional process is a method of dropping fatty acyl chloride and liquid alkali into the sodium methyl taurate solution alternately or simultaneously, because the density of the fatty acyl chloride is about 0.9g/ml, the density of 40% methyl taurate solution is about 1.2g/ml, and the compatibility of the fatty acyl chloride and the methyl taurate solution is very poor, the local concentration of the fatty acyl chloride is easily too high, and the hydrolysis rate of the fatty acyl chloride increases with the increase of temperature. In order to avoid excessive hydrolysis of fatty acyl chloride, only low-temperature reaction (below 40 ℃) can be adopted, the viscosity of each raw material and the generated N-acyl-N-methyl taurate is higher at low temperature, when the fatty acyl chloride is dripped into a certain proportion, the feed liquid becomes sticky and is difficult to be uniformly mixed, and only products with the active matter content lower than 40% can be prepared.
In the invention, the methyl taurate aqueous solution is preheated to 40-70 ℃, more specifically to 50-60 ℃, the heating mode can be heating in a drying room by adopting an original package or heating the methyl taurate aqueous solution and the fatty acyl chloride to a required temperature by adding a preheating kettle, then the methyl taurate aqueous solution and the fatty acyl chloride are respectively placed in a first elevated tank 10 and a second elevated tank 20 and synchronously dripped into a spiral pipeline 40, the methyl taurate aqueous solution and the fatty acyl chloride are mixed by a section of inclined spiral pipeline 40, liquid alkali is placed in a third elevated tank 30, when the mixed solution of the methyl taurate aqueous solution and the fatty acyl chloride enters the tail end of the spiral pipeline 40, the liquid alkali begins to be dripped into the tail end of the spiral pipeline 40 for mixing, the spiral pipeline 40 is used for fully mixing the methyl taurate aqueous solution and the fatty acyl chloride, the methyl taurate aqueous solution, the fatty acyl chloride and the liquid alkali, the methyl taurate aqueous solution and the fatty acyl chloride start to flow downwards after being synchronously dripped, when the methyl taurate aqueous solution and the fatty acyl chloride flow to the tail end of the spiral pipeline 40, the liquid alkali is synchronously dripped, so that the methyl taurate aqueous solution and the fatty acyl chloride are synchronously dripped at the tail end of the spiral pipeline 40, when the mixed solution of the methyl taurate aqueous solution and the fatty acyl chloride enters the main reaction kettle 50, the reaction lasts for 1 h-3 h, the temperature of the main reaction kettle 50 is set to 60 ℃ -80 ℃, and finally, a subsequent curing step is carried out, specifically, water or steam is introduced outside the main reaction kettle 50 for heat preservation and standing, the heat preservation.
The initial temperature is higher, and methyl taurine salt solution and fatty acyl chloride are the synchronous dropwise add of same proportion throughout to methyl taurine salt solution, fatty acyl chloride and liquid caustic soda three are in fact for synchronous dropwise add the mixture, have avoided the local concentration of fatty acyl chloride too high like this, have avoided the excessive hydrolysis of fatty acyl chloride, have reduced the formation of impurity. In addition, the high initial reaction temperature enables the viscosity of the mixed solution of the methyl taurate solution with high concentration and the fatty acyl chloride to be still small, and the mixed solution is easy to flow and mix, so that the production of the N-acyl-N-methyl taurate surfactant with high content becomes easy to realize; and the preparation process for preparing the acyl methyl taurate surfactant aqueous solution with the active substance content of more than 40 percent is simple.
It is further explained that the sodium methyl taurate solution and the fatty acyl chloride are mixed at the front end of the spiral pipeline 40, the material temperature is 40-50 ℃, and the pH value is about 10. The spiral pipeline 40 enables a sodium methyl taurate solution and a fatty acyl chloride mixed solution to generate turbulence and spontaneously carry out condensation reaction, the temperature of the mixed solution is raised to 70-80 ℃ at the tail end of the pipeline, meanwhile, the pH value is reduced to 7-8, liquid caustic soda is mixed into the tail end of the pipeline, the pH value is raised to 9-10, and after the liquid caustic soda is mixed, the mixed solution enters the main reaction kettle 50 for full reaction.
The mol ratio of the raw materials of the methyl taurate, the fatty acyl chloride and the liquid alkali used in the preparation method of the N-acyl-N-methyl taurate is 1: 1.0-1.3: 0.9-1.1, more specifically, the molar ratio of the methyl taurate, the fatty acyl chloride and the liquid alkali is 1: 0.98-1.02: 0.98-1.02.
Firstly, methyl taurate solution and fatty acyl chloride are synchronously dripped at the upper end of the spiral pipeline 40, the methyl taurate solution and the fatty acyl chloride are fully mixed through the inclined spiral pipeline 40, then the liquid caustic soda begins to be dripped into the mixed liquid of the methyl taurate solution and the fatty acyl chloride to be mixed when entering the tail end of the spiral pipeline 40, then the mixed liquid enters the main reaction kettle 50, and the methyl taurate solution, the fatty acyl chloride and the liquid caustic soda actually synchronously enter the main reaction kettle 50 at respective dripping speeds for reaction.
The same proportion is synchronously dripped at different speeds, which is beneficial to the mixing of the three, so that the fatty acyl chloride and the methyl taurate can be fully and uniformly mixed, the local concentration of the fatty acyl chloride is avoided from being too high, the dripping of enough liquid caustic soda can promote the reaction, and the dripping mixing is beneficial to the generation of the N-acyl-N-methyl taurate after entering the main reaction kettle 50.
The mass percentage of the methyl taurate in the methyl taurate aqueous solution is 25-40%.
More specifically, the mass percent of the methyl taurate in the methyl taurate aqueous solution is 35-40%.
The fatty acyl chloride is octanoyl chloride, decanoyl chloride, lauroyl chloride, C12～18Cocoyl chloride or C12～18One of cocoyl chloride.
The methyl taurate is one of sodium methyl taurate or potassium methyl taurate.
The dropping speeds of the methyl taurine salt solution, the fatty acyl chloride and the liquid caustic soda are respectively 13kg/min to 22kg/min, 6kg/min to 10kg/min and 4kg/min to 6 kg/min.
Therefore, the even mixing of the methyl taurine salt solution, the fatty acyl chloride and the liquid caustic soda is facilitated, and the local concentration of the fatty acyl chloride is avoided from being too high.
The apparatus for producing N-acyl-N-methyltaurate is described in detail below, as shown in FIG. 1,
the equipment for producing the N-acyl-N-methyl taurate comprises a first elevated tank 10, a second elevated tank 20, a third elevated tank 30, a spiral pipeline 40, a main reaction kettle 50 and a circulation cavity 60, wherein the circulation cavity 60 is arranged on the outer surface of the main reaction kettle 50, the first elevated tank 10 is used for containing methyl taurate solution, the second elevated tank 20 is used for containing fatty acyl chloride, the third elevated tank 30 is used for containing caustic soda liquid, the methyl taurate aqueous solution and the fatty acyl chloride synchronously begin to drip, synchronously enter the section of the inclined spiral pipeline 40, are mixed through the spiral pipeline 40, when the mixed solution of the methyl taurate aqueous solution and the fatty acyl chloride enters the spiral pipeline 40 as the tail end, the liquid caustic soda begins to drip synchronously to the tail end of the spiral pipeline 40, the three are mixed and then enter the main reaction kettle 50 for reaction, and after the reaction is finished, cooling water or steam is introduced into the circulation cavity 60 for cooling, the main reaction kettle 50 is cooled to the required temperature, the temperature is kept and the main reaction kettle is kept and placed still, an inlet is formed in the upper portion of the circulation cavity 60, an outlet is also formed in the lower portion of the circulation cavity 60, and cooling water or steam entering from the inlet is discharged from the outlet after passing through the interior of the circulation cavity 60.
Spiral pipeline 40 is the non-metallic material pipeline, prefers one of non-metallic material pipelines such as PE pipeline, PP pipeline, PVC pipeline, PPR pipeline, PTFE pipeline and PVDF pipeline.
The PE pipeline is the pipeline that polyethylene material made, and the PP pipeline is the pipeline that polypropylene was made, and the PVC pipeline is the pipeline that polyvinyl chloride was made, and the PPR pipeline is the pipeline that random copolymerization polypropylene was made, and the PTFE pipeline is the pipeline that polytetrafluoroethylene was made, and the PVDF pipeline is the pipeline that polyvinylidene fluoride was made.
The pipe diameter of the spiral pipeline 40 is DN 25-DN 80.
The pipe diameter is DN 25-DN 80, which means that the pipe diameter of the spiral pipe 40 is 34 mm-89 mm, more specifically, the pipe diameter of the spiral pipe 40 is DN50, namely the pipe diameter of the spiral pipe 40 is 50 mm.
Like this, ensure methyl taurine salt solution and fatty acyl chloride can be in spiral pipeline 40 intensive mixing homogeneous, avoid fatty acyl chloride's local concentration too high, reduce impurity, improve the conversion rate.
The length of the spiral duct 40 is 1m to 10m, and the inclination angle is 10 to 60 degrees, more specifically, the length of the spiral duct 40 is 3m to 5m, and the inclination angle is 20 to 30 degrees.
Like this, ensure methyl taurine salt solution and fatty acyl chloride can be in spiral pipeline 40 intensive mixing homogeneous, avoid fatty acyl chloride's local concentration too high, reduce impurity, improve the conversion rate.
The invention also provides silicone-oil-free shampoo, which comprises 7-9% of N-acyl-N-methyl taurate surfactant prepared by adopting a preparation method of N-acyl-N-methyl taurate, 9-11% of sodium laureth sulfate, 4-6% of cocamidopropyl betaine, 1-3% of cocamide DEA, 1-3% of ammonium lauryl sulfate, 1-2% of glyceryl oleate, 1-2% of cocoyl glucoside, 0.5-1% of sodium lauroamphoacetate, 0.5-1% of panthenol, 0.5-1% of essence, 0.1-0.8% of sodium lauroyl glutamate, 0.1-0.8% of sodium lauroyl sarcosinate, 0.1-0.8% of guar hydroxypropyl trimethyl ammonium chloride, 0.1-0.5% of allantoin and 0.1-0.5% of hydrolyzed wheat protein PG-propyl silanetriol (calculated by mass ratio), 0.1 to 0.5 percent of polyquaternium-10, 0.1 to 0.2 percent of hydrogenated lecithin, 0.1 to 0.2 percent of quaternary ammonium salt-82, 0.1 to 0.2 percent of lauryl dimethyl ammonium hydroxypropyl hydrolyzed wheat protein, 0.1 to 0.2 percent of EDTA disodium, 0.1 to 0.2 percent of pyridoxine HCl, 0.1 to 0.2 percent of silk fibroin, 0.01 to 0.1 percent of hydroxyethyl diphosphate and 0.1 to 0.5 percent of phenoxyethanol.
The N-acyl-N-methyltaurine salt is an anionic surfactant with high safety, has excellent foamability, water solubility and hard water resistance, is applied to the silicone-free shampoo, has low irritation to human bodies, and can make hair mild, moist and smooth after being used.
Some specific examples are listed below, but it should be noted that the following examples are not exhaustive of all possible cases. And the materials used in the following examples are commercially available unless otherwise specified.
Example 1
Heating a 40% sodium methyl taurate solution in a drying room to about 50 ℃;
pumping 2300kg of preheated 40% sodium methyl taurate solution into a first elevated tank 10, and pumping 300kg of deionized water, wherein the concentration of the sodium methyl taurate solution is 35.3% and the temperature is about 48 ℃;
then, 1200kg of 99% lauroyl chloride is pumped into the second head tank 20, and 680kg of 32% caustic soda liquid is pumped into the third head tank 30;
simultaneously, 35% of sodium methyl taurate solution, 99% of lauroyl chloride and 32% of liquid caustic soda are dripped, the dripping speed is respectively controlled at 22kg/min, 10kg/min and 5.5kg/min, and the dripping is finished within 1.8 h. After entering the main reaction kettle 50, the material temperature is kept at 75 ℃, the reaction is carried out for 2h, and then the curing is carried out for 2 h.
Example 2
Heating a 40% sodium methyl taurate solution in a drying room to about 70 ℃;
1600kg of 40% sodium methyl taurate solution is pumped into the first elevated tank 10, and 1200kg of deionized water is pumped into the first elevated tank, wherein the concentration of the sodium methyl taurate solution is 30% and the temperature is about 50 ℃;
then pumping 900kg of 99% cocoyl chloride into the second head tank 20, and pumping 480kg of 32% caustic soda liquid into the third head tank 30;
simultaneously, dripping 40% of sodium methyl taurate solution, 99% of cocoyl chloride and 32% of liquid alkali at the speed of 13.5kg/min, 7.5kg/min and 4kg/min respectively, and finishing dripping within 2.5 h. After entering the main reaction kettle 50, the material temperature is kept at 65 ℃, and then the curing is carried out for 2 hours.
Example 3
Heating a 40% sodium methyl taurate solution in a drying room to about 65 ℃;
1600kg of a 40% sodium methyl taurate solution is pumped into a first head tank 10;
then pumping 900kg of 99% octanoyl chloride into the second head tank 20, and pumping 480kg of 32% caustic soda liquid into the third head tank 30;
simultaneously, dropwise adding 40% of sodium methyl taurate solution, 99% of octanoyl chloride and 32% of liquid alkali, controlling the dropwise adding speed at 18kg/min, 8kg/min and 5kg/min respectively, and finishing dropwise adding within 2 hours. After entering the main reaction kettle 50, the material temperature is kept at 65 ℃, and then the curing is carried out for 2 hours.
Example 4
2300kg of 40% sodium methyl taurate aqueous solution is added into a reaction kettle;
then, 1200kg of 99% lauroyl chloride is pumped into a head tank, and 680kg of 32% caustic soda liquid is pumped into another same head tank;
starting a refrigerating machine, cooling the aqueous solution of the sodium methyl taurate to 15 ℃ under the stirring condition, simultaneously starting to dropwise add the lauroyl chloride and the liquid caustic soda, controlling the dropwise adding speeds of the 99% lauroyl chloride and the 32% liquid caustic soda to be 10kg/min and 5.5kg/min respectively, and finishing dropwise adding within 2 hours.
In the process of dropwise adding materials for reaction, the material temperature is controlled below 40 ℃, the pH value is controlled between 9 and 11, after dropwise adding, steam heating is started, the material temperature is gradually increased to 75 ℃ under stirring, stirring is stopped after 2 hours, and then curing is carried out for 2 hours.
Example 5
The components and the dosage of the silicone oil-free shampoo are shown in the following table 1:
TABLE 1
Example 6
Commercially available shampoos, the composition and amount of which are shown in table 2, were commercially available:
TABLE 2
The test data of the N-acyl-N-methyltaurate salt obtained by the method for preparing the N-acyl-N-methyltaurate salt of the present invention are as follows:
purpose of the experiment
The impurity content and the active substance content of the N-acyl-N-methyltaurate salt obtained by the method for preparing the N-acyl-N-methyltaurate salt of the present invention were tested.
Principle of experiment
The anion active content X is expressed in mass percent (%) and is calculated as follows:
in the formula: x-anionic active content,%;
m3-sample mass, g;
Mr-average relative molecular weight of anionic actives;
c3concentration of benzylsuonium chloride solution, mol/L;
V3-volume of benzylphosphonium chloride solution consumed at the time of titration, mL;
test protocol
Test substance: the N-acyl-N-methyl taurine salt solution, the standard phenolphthalein solution, the standard sodium hydroxide solution, the standard sulfuric acid solution, the standard trichloromethane, the standard acidic mixed indicator solution and the standard benzyl-threonium chloride solution obtained in the embodiments 1 to 4 of the present invention (refer to International Standard ISO 2271:1989, surfactant-detergent, determination of anionic active substance by manual or mechanical direct two-phase titration);
and (3) test grouping treatment: the N-acyl-N-methyltaurate solutions obtained in example 2 and example 3 of example 1 were used as test group 1, test group 2 and test group 3, respectively, and the N-acyl-N-methyltaurate solution obtained in example 4 was used as a control;
the test method comprises the following steps: the anionic activity is determined by direct two-phase titration, manually or mechanically, using the surfactant-detergent method of International Standard ISO 2271: 1989.
Test procedure
1. Weighing 3.5g of N-acyl-N-methyl taurate solution of each test group and each control group, weighing the solution to 1mg, and putting the solution into a 150mL beaker;
2. adding a dropwise phenolphthalein solution into the weighed N-acyl-N-methyltaurate solution of each group, neutralizing with a sodium hydroxide solution or a sulfuric acid solution to be light pink according to requirements, quantitatively transferring into a 1000 mL volumetric flask, diluting with water to a scale, and uniformly mixing.
3. Transferring 25mL of the solution into a measuring cylinder with a plug by using a pipette, adding 10mL of water, 15mL of trichloromethane and 10mL of acidic mixed indicator solution, and titrating by using a benzylsustronium chloride solution to an end point;
4. and recording data and calculating a result.
Test results
The amount of impurities in the N-acyl-N-methyltaurate solution can be determined based on the content of sodium chloride and free acid, and the calculated test results are shown in table 3:
TABLE 3
Conclusion of the experiment
The active substances in the N-acyl-N-methyl taurine salt solution of the test group 1-3 are obviously higher than the N-acyl-N-methyl taurine salt solution obtained in the prior art in the control group, namely the preparation method of the N-acyl-N-methyl taurine salt has high conversion rate; and the impurity content of the test group 1-3 is obviously less than that of the control group, namely the preparation method of the N-acyl-N-methyltaurate can reduce the impurity content of the N-acyl-N-methyltaurate solution.
The silicone oil-free shampoo disclosed by the invention is tested, and the test data are as follows:
purpose of the experiment
The influence on the moistening and the smoothness of the hair after the silicone oil-free shampoo is used is tested.
Test protocol
Test substance: the silicone oil-free shampoo of example 5 of the invention and the commercially available shampoo of example 6;
and (3) test grouping treatment: the silicone oil-free shampoo of example 5 of the present invention was used as a test group, and the commercially available shampoo of example 6 was used as a control group.
Test procedure
1. Selecting 40 women with 18-25 ages and healthy hair, wherein the length of the hair is approximately the same, and the women are averagely divided into a test group and a control group, wherein the hair of 20 women in the test group uses the silicone oil-free shampoo of the test group, and the hair of 20 women in the control group uses the commercial shampoo of the control group;
2. using a dynamic combing property simulation tester to perform combing property evaluation before using corresponding shampoo;
3. then, the hair of 40 women uses corresponding shampoo respectively, and the combing performance is evaluated by using a dynamic combing performance simulation tester during foaming, before washing, after washing and after washing in the hair washing process;
4. finally, after respective hair is dried, a dynamic combing nature simulation tester is used for carrying out combing performance evaluation;
5. and recording data and calculating a result.
Test results
The results are shown in fig. 1 (average), where the measured data are the force required to comb the hair, the larger the data, i.e. indicating that the larger the force required to comb, the worse the combing performance.
Conclusion of the experiment
According to the test results, the non-silicone oil shampoo and the commercially available shampoo have no statistical difference in the combing performance at each stage, so that the requirements of the shampoo on the mildness, the moisture and the smoothness of the hair are met.
The technical features of the above embodiments can be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the above embodiments are not described, but should be considered as the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above examples only show some embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
- A process for the preparation of N-acyl-N-methyltaurate, characterized in that it comprises the following steps:s1, selecting a methyl taurate aqueous solution, fatty acyl chloride and liquid alkali as raw materials;s2, preheating a methyl taurate aqueous solution to 40-70 ℃;s3, respectively placing the methyl taurate aqueous solution and the fatty acyl chloride in a first elevated tank and a second elevated tank, synchronously dropwise adding the methyl taurate aqueous solution and the fatty acyl chloride into a section of inclined spiral pipeline, and mixing the methyl taurate aqueous solution and the fatty acyl chloride through the spiral pipeline;s4, placing the liquid caustic soda in another third elevated tank, and synchronously dropwise adding the liquid caustic soda and the mixed liquid of the methyl taurate aqueous solution and the fatty acyl chloride in the S3, wherein the liquid caustic soda, the methyl taurate aqueous solution and the fatty acyl chloride synchronously enter the tail end of the spiral pipeline to be mixed;s5, feeding the mixed solution of the three into a main reaction kettle, reacting for 1-3 h, and setting the temperature of the main reaction kettle to be 60-80 ℃.
- 2. The method for preparing N-acyl-N-methyltaurate according to claim 1, wherein the molar ratio of fatty acid chloride, methyltaurate and liquid base is 1: 1.0-1.3: 0.9 to 1.1.
- 3. The method for preparing N-acyl-N-methyltaurate according to claim 1, wherein the mass percentage of methyltaurate in the aqueous solution of methyltaurate is 25% to 40%.
- 4. The method for preparing N-acyl-N-methyltaurate according to claim 1, wherein the fatty acid chloride is octanoyl chloride, decanoyl chloride, lauroyl chloride, C12～18Cocoyl chloride or C12～18One of cocoyl chloride.
- 5. The method of claim 1, wherein the methyltaurate is one of sodium methyltaurate and potassium methyltaurate.
- 6. The method for preparing N-acyl-N-methyltaurate according to claim 1, wherein the dropping speeds of the solution of methyltaurate salt, the fatty acid chloride and the liquid alkali are 13kg/min to 22kg/min, 6kg/min to 10kg/min and 4kg/min to 6kg/min, respectively.
- 7. The method of claim 1, wherein the spiral pipe is one of a PE pipe, a PP pipe, a PVC pipe, a PPR pipe, a PTFE pipe, and a PVDF pipe.
- 8. The method for preparing N-acyl-N-methyltaurine salt as claimed in claim 1, wherein the pipe diameter of the spiral pipe is DN 25-DN 80.
- 9. The method for preparing N-acyl-N-methyltaurate according to claim 1, wherein the helical piping has a length of 1m to 10m and an inclination angle of 10 ° to 60 °.
- 10. The use of the N-acyl-N-methyltaurate prepared by the method for preparing an N-acyl-N-methyltaurate according to any one of claims 1 to 9 in a silicone oil-free shampoo.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113444014A (en) * | 2021-06-28 | 2021-09-28 | 江苏金桥油脂科技有限公司 | System and method for continuously producing N-acyl amino acid surfactant |
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