CN109627181B - Amino acid modified amphoteric surfactant and preparation method thereof - Google Patents
Amino acid modified amphoteric surfactant and preparation method thereof Download PDFInfo
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- CN109627181B CN109627181B CN201910099041.3A CN201910099041A CN109627181B CN 109627181 B CN109627181 B CN 109627181B CN 201910099041 A CN201910099041 A CN 201910099041A CN 109627181 B CN109627181 B CN 109627181B
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- 150000001413 amino acids Chemical class 0.000 title claims abstract description 34
- 239000002280 amphoteric surfactant Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
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- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 2
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- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
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- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004473 Threonine Substances 0.000 claims description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 229960003767 alanine Drugs 0.000 claims description 2
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- 229960003121 arginine Drugs 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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- 229960001153 serine Drugs 0.000 claims description 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
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- 230000000844 anti-bacterial effect Effects 0.000 abstract description 6
- 125000000129 anionic group Chemical group 0.000 abstract description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- 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
- C07C233/34—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 amino groups
- C07C233/35—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 amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—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 amino 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention provides an amino acid modified amphoteric surfactant, which is characterized by being a compound shown in the following structure:
wherein, R, R' and R1、R1’、R2、R3、R3' are identical or different substituents; the substituents are selected from hydrogen, alkyl, aryl, heteroaryl. Because the molecular structure of the antibacterial foam simultaneously retains the carboxyl of amino acid and the quaternary amino group formed by N-alkylation, the molecular simultaneously has an anionic group and a cationic group, so the antibacterial foam has good compatibility and mild antibacterial effect, can provide rich foam, and is very mild to hair and skin. The invention has the advantages of easy control of the production process, mild reaction, cheap and easily obtained raw materials and no generation of three wastes.
Description
Technical Field
The invention relates to the field of surfactants, in particular to an amino acid modified amphoteric surfactant and a preparation method thereof.
Background
The currently researched amino acid surfactants comprise N-alkyl amino acid surfactants and N-acyl amino acid surfactants, wherein the research and development of the N-acyl amino acid surfactants are mature and are industrially produced, fatty acyl chloride and amino acid are used for reaction in the production process, however, the preparation of the fatty acyl chloride and the refining and purification of the reaction product of the fatty acyl chloride and the amino acid generate a large amount of byproducts, namely three wastes, and in addition, the method can only produce anionic surfactants which can only be mixed with anionic or nonionic surfactants.
Disclosure of Invention
The invention aims to overcome the defects and provides an amino acid modified amphoteric surfactant.
The invention provides an amino acid modified amphoteric surfactant which is characterized by being a compound shown in the following structure:
wherein, R, R' and R1、R1’、R2、R3、R3' are identical or different substituents;
the above substituents are selected from hydrogen, alkyl, aryl, heteroaryl.
The above alkyl groups refer to straight-chain, branched-chain and cycloalkyl groups, wherein the R group is preferably an alkyl group having more than 7 carbon atoms;
the aryl group refers to aromatic groups with 6-30 carbon atoms such as phenyl, benzyl, quinolyl and the like;
the heteroaryl refers to phenyl, benzyl, quinolyl and the like, wherein one or more carbon atoms on an aromatic ring of an aromatic group with 6-30 carbon atoms are replaced by oxygen, sulfur and nitrogen.
In addition, the invention also provides a preparation method of the amino acid modified amphoteric surfactant, which is characterized in that epichlorohydrin or derivatives thereof are subjected to alkylation reaction with amino acid, and then the reaction product is reacted with N, N-dimethyl-N-fatty acyl propane diamine to obtain the target benign surfactant.
The specific reaction equation is as follows:
the preparation method of the amino acid modified amphoteric surfactant further has the characteristic that the amino acid is selected from one or more of alanine, valine, leucine, isoleucine, methionine, aspartic acid, glutamic acid, lysine, arginine, glycine, serine, threonine, cysteine, asparagine, glutamine, phenylalanine, tyrosine, histidine, tryptophan and proline.
Most preferred are glycine, glutamic acid, lysine, aspartic acid, histidine and the like.
Furthermore, the preparation method of the amino acid modified amphoteric surfactant provided by the invention is also characterized in that the derivative of the epichlorohydrin is selected from one or more compounds shown in the following structures,
wherein R is1、R1’、R2、R3、R3' are identical or different substituents;
the substituents are selected from hydrogen, alkyl and aryl.
Furthermore, the preparation method of the amino acid modified amphoteric surfactant provided by the invention is also characterized in that the N, N-dimethyl-N-fatty acyl propane diamine is selected from one or more compounds shown in the specification,
wherein R is an alkyl group having not less than 7 carbon atoms.
Most preferably C7H15、C11H23、C15H31、C17H35、C21H43。
The method for producing an amino acid-modified amphoteric surfactant according to claim 2, wherein:
the mass ratio of the epichlorohydrin to the amino acid is 0.2-0.8: 1.
The preparation method of the amino acid modified amphoteric surfactant has the characteristic that the mass ratio of the N, N-dimethyl-N-fatty acyl propane diamine to the reaction product of the epoxy chloropropane and the amino acid is 1: 1.5-3.
Furthermore, the preparation method of the amino acid modified amphoteric surfactant provided by the invention has the following characteristics that:
step one, adjusting the pH of an aqueous solution of amino acid or hydrochloride thereof to 5-7;
step two, heating the reaction system in the step one to 40-50 ℃;
step three, dripping epichlorohydrin or derivatives thereof, and reacting for 3-5 hours at the current system temperature after finishing dripping to obtain an intermediate;
step four, controlling the temperature of the aqueous solution of the intermediate at 75-85 ℃, and adding N, N-dimethyl-N-fatty acyl propane diamine;
and step five, controlling the reaction temperature to react for 6 to 8 hours at the temperature of between 80 and 100 ℃ to obtain a target product.
Furthermore, the preparation method of the amino acid modified amphoteric surfactant provided by the invention is also characterized in that the pH adjusting process in the first step is completed by inorganic acid or inorganic base.
Furthermore, the preparation method of the amino acid modified amphoteric surfactant provided by the invention has the characteristics that in the third step, the temperature of a reaction system is controlled to be 90-100 ℃ in the dropping process.
The invention has the following functions and effects:
the invention relates to an amino acid modified amphoteric surfactant, which belongs to a preparation method of N-alkyl amino acid surfactants, and is an amphoteric surfactant, but the prior art can only produce anionic surfactants. The amino acid surfactant is synthesized by taking amino acid as a raw material, and the raw material belongs to organism components, can be regenerated, is easy to biodegrade and has low toxicity, so the amino acid surfactant has a great application prospect in industries such as food, medicine and cosmetics.
The N-alkyl amino acid surfactant is an amphoteric surfactant, and the molecular structure of the surfactant simultaneously retains the carboxyl of amino acid and the quaternary amino group formed by N-alkylation, so that the molecule simultaneously has an anionic group and a cationic group, and the surfactant has good compatibility and a mild antibacterial effect, can provide rich foam and is very mild to hair and skin. The invention has the advantages of easy control of the production process, mild reaction, low cost and easy obtainment, and no generation of three wastes.
Detailed Description
Examples 1,
The following reaction equation is used:
the specific reaction process is as follows:
225kg of water is added into a reaction kettle provided with a condensation reflux device, the temperature is raised to 50 ℃ by stirring, 150kg of glycine is added, and after the glycine is completely dissolved, the pH value is adjusted to 5 by using a sodium hydroxide solution. And then, uniformly and slowly adding 75kg of epoxy chloropropane into the reaction kettle from the head tank within 40-60 minutes, controlling the temperature to be 90-100 ℃ in the dropwise adding process, and preserving heat for 3 hours after the dropwise adding is finished. The reaction product is not required to be purified and can be directly used for the next reaction.
2. 450kg of water and 225kg of N, N-dimethyl-N-fatty acyl propanediamine (R is C) were added to a reaction vessel7H13) Stirring and heating to 75 ℃, then adding 450kg of intermediate 3-chloro-2-hydroxypropyl amino acid, continuously stirring and heating to 90 ℃, keeping the temperature for 6 hours, and cooling after the reaction is finished to obtain the required product.
Example 2
225kg of water is added into a reaction kettle provided with a condensing reflux device, the temperature is raised to 50 ℃ by stirring, 150kg of lysine hydrochloride is added, and after the lysine hydrochloride is completely dissolved, the pH value is adjusted to 5 by using a sodium hydroxide solution. And then, uniformly and slowly adding 75kg of epoxy chloropropane into the reaction kettle from the head tank within 40-60 minutes, controlling the temperature to be 90-100 ℃ in the dropwise adding process, and preserving heat for 3 hours after the dropwise adding is finished. The reaction product is not required to be purified and can be directly used for the next reaction.
450kg of water and 225kg of N, N-dimethyl-N-fatty acyl propanediamine (R is C) were added to a reaction vessel11H23) Stirring and heating to 75 ℃, then adding 450kg of intermediate 3-chloro-2-hydroxypropyl amino acid, continuously stirring and heating to 90 ℃, keeping the temperature for 6 hours, and cooling after the reaction is finished to obtain the required product.
Example 3
225kg of water is added into a reaction kettle provided with a condensation reflux device, the temperature is raised to 50 ℃ by stirring, 150kg of glutamic acid is added, and after the glutamic acid is completely dissolved, the pH value is adjusted to 6 by using a sodium hydroxide solution. And then, uniformly and slowly adding 75kg of epoxy chloropropane into the reaction kettle from the head tank within 40-60 minutes, controlling the temperature to be 90-100 ℃ in the dropwise adding process, and preserving heat for 5 hours after the dropwise adding is finished. The reaction product is not required to be purified and can be directly used for the next reaction.
450kg of water and 225kg of N, N-dimethyl-N-fatty acyl propanediamine (R is C) were added to a reaction vessel17H35) Stirring and heating to 85 ℃, then adding 450kg of intermediate 3-chloro-2-hydroxypropyl amino acid, continuously stirring and heating to 90 ℃, keeping the temperature for 8 hours, and cooling after the reaction is finished to obtain the required product.
Example 4
200kg of water is added into a reaction kettle provided with a condensation reflux device, the temperature is raised to 45 ℃ by stirring, 120kg of aspartic acid is added, and after the aspartic acid is completely dissolved, the pH value is adjusted to 7 by using a sodium hydroxide solution. Then, 95kg of 1, 1-dimethyl epichlorohydrin is uniformly and slowly added into the reaction kettle from the head tank within 40-60 minutes, the temperature is controlled to be 90-100 ℃ in the dropping process, and the temperature is kept for 6 hours after the dropping is finished. The reaction product is not required to be purified and can be directly used for the next reaction.
400kg of water and 205kg of N, N-dimethyl-N-fatty acyl propanediamine (R is C) were charged in a reaction vessel12H23) Stirring and heating to 95 ℃, then adding 450kg of intermediate obtained by reaction, continuously stirring and heating to 100 ℃, preserving heat for 6 hours, and cooling after the reaction is finished to obtain the required product.
Example 5
200kg of water is added into a reaction kettle provided with a condensation reflux device, the temperature is raised to 45 ℃ by stirring, 150kg of phenylalanine is added, and after the phenylalanine is completely dissolved, the pH value is adjusted to 7 by using a sodium hydroxide solution. Then, 95kg of 1, 1-dimethyl-2-dodecyl-epichlorohydrin is uniformly and slowly added into the reaction kettle from the head tank within 40-60 minutes, the temperature is controlled to be 90-100 ℃ in the dropping process, and the temperature is kept for 4 hours after the dropping is finished. The reaction product is not required to be purified and can be directly used for the next reaction.
400kg of water and 220kg of N, N-dimethyl-N-fatty acyl propanediamine (R is C)12H23) And stirring and heating to 95 ℃, then adding 350kg of intermediate obtained in the previous step, continuously stirring and heating to 100 ℃, preserving heat for 7 hours, and cooling after the reaction is finished to obtain the required product.
Taking the product of the above example as an example, the following performance tests were performed:
first, foaming force and foam stability test:
measured using a 2151 Roche foam tester (QB 511279). 2.5g of the synthesized surfactant is weighed, the volume is fixed to 1L by hard water with the concentration of 0.15mmol/L to obtain foaming liquid, and the temperature is controlled at 40 ℃. After the tube wall of the Roche foam meter is completely flushed by the foaming liquid, the foaming liquid is injected and the liquid level is adjusted to 50ml scale. A dropping liquid tube containing 200ml of foaming liquid is vertically placed on a tube frame, a piston is opened, a stopwatch is started immediately when the solution in the dropping liquid tube flows out, and the foam height (mm) is recorded, wherein the foam height is the foaming force of the surfactant, and the foam height after 5min is the foam stabilizing force of the surfactant.
II, antibacterial property
Has antibacterial effect on Staphylococcus aureus and Escherichia coli
Three, compatibility with cationic and anionic surfactants in one bath
The synthesized surfactant was mixed with cationic surfactant (octadecyl trimethyl ammonium chloride) and anionic surfactant (sodium dodecylbenzenesulfonate) at a ratio of 1:1 to prepare 50% aqueous solutions, and then observed for delamination or coagulation within 24 hours.
Claims (10)
1. An amino acid modified amphoteric surfactant, which is characterized in that the surfactant is a compound shown in the following structure:
wherein R, R ', R1, R1 ', R2, R3 and R3 ' are same or different substituent groups;
the substituent is selected from hydrogen, alkyl, aryl and heteroaryl;
the alkyl refers to an alkyl group with more than 7 carbon atoms;
the aryl refers to an aromatic group with 6-30 carbon atoms;
the heteroaryl refers to the substitution of one or more carbon atoms on the aromatic ring of the aromatic group with the carbon number of 6-30 by oxygen, sulfur and nitrogen.
2. The process for preparing an amino acid-modified amphoteric surfactant according to claim 1, wherein the desired benign surfactant is obtained by reacting epichlorohydrin or a derivative thereof with an amino acid and then reacting the resultant product with N, N-dimethyl-N-fatty acyl propane diamine.
3. The method for producing an amino acid-modified amphoteric surfactant according to claim 2, wherein:
the amino acid is selected from one or more of alanine, valine, leucine, isoleucine, methionine, aspartic acid, glutamic acid, lysine, arginine, glycine, serine, threonine, cysteine, asparagine, glutamine, phenylalanine, tyrosine, histidine, tryptophan and proline.
4. The method for producing an amino acid-modified amphoteric surfactant according to claim 2, wherein:
the derivative of the epichlorohydrin is selected from one or more of the compounds shown in the specification,
wherein R is1、R1’、R2、R3、R3' are identical or different substituents;
the substituent is selected from hydrogen, alkyl and aryl.
5. The method for producing an amino acid-modified amphoteric surfactant according to claim 2, wherein:
the N, N-dimethyl-N-fatty acyl propane diamine is selected from one or more of the following compounds,
wherein R is an alkyl group having not less than 7 carbon atoms.
6. The method for producing an amino acid-modified amphoteric surfactant according to claim 2, wherein:
the mass ratio of the epichlorohydrin to the amino acid is 0.2-0.8: 1.
7. The method for producing an amino acid-modified amphoteric surfactant according to claim 2, wherein:
the mass ratio of the N, N-dimethyl-N-fatty acyl propane diamine to the reaction product of the epoxy chloropropane and the amino acid is 1: 1.5-3.
8. The method for producing an amino acid-modified amphoteric surfactant according to claim 2, wherein the specific production method is as follows:
step one, adjusting the pH of an aqueous solution of amino acid or hydrochloride thereof to 5-7;
step two, heating the reaction system in the step one to 40-50 ℃;
step three, dripping epichlorohydrin or derivatives thereof, and reacting for 3-5 hours at the current system temperature after finishing dripping to obtain an intermediate;
step four, controlling the temperature of the aqueous solution of the intermediate at 75-85 ℃, and adding N, N-dimethyl-N-fatty acyl propane diamine;
and step five, controlling the reaction temperature to react for 6 to 8 hours at the temperature of between 80 and 100 ℃ to obtain a target product.
9. The method for producing an amino acid-modified amphoteric surfactant according to claim 8, wherein:
the pH adjusting procedure of the first step is completed by inorganic acid or inorganic base.
10. The method for producing an amino acid-modified amphoteric surfactant according to claim 8, wherein:
in the third step, the temperature of the reaction system is controlled to be 90-100 ℃ in the dropping process.
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