CN113181828A - Environment-friendly amino acid modified organic silicon surfactant and preparation method thereof - Google Patents
Environment-friendly amino acid modified organic silicon surfactant and preparation method thereof Download PDFInfo
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- CN113181828A CN113181828A CN202110291910.XA CN202110291910A CN113181828A CN 113181828 A CN113181828 A CN 113181828A CN 202110291910 A CN202110291910 A CN 202110291910A CN 113181828 A CN113181828 A CN 113181828A
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 82
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 77
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 27
- 239000010703 silicon Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 239000007864 aqueous solution Substances 0.000 claims abstract description 50
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 44
- 229920000570 polyether Polymers 0.000 claims abstract description 44
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 14
- -1 amino acid sodium salt Chemical class 0.000 claims abstract description 9
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000012736 aqueous medium Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 235000001014 amino acid Nutrition 0.000 claims description 71
- 238000010438 heat treatment Methods 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 150000003961 organosilicon compounds Chemical group 0.000 claims description 10
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 10
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 9
- 239000004472 Lysine Substances 0.000 claims description 9
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 8
- 229910018557 Si O Inorganic materials 0.000 claims description 8
- 235000013922 glutamic acid Nutrition 0.000 claims description 8
- 239000004220 glutamic acid Substances 0.000 claims description 8
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims description 8
- 239000004471 Glycine Substances 0.000 claims description 6
- 108010077895 Sarcosine Proteins 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 229940043230 sarcosine Drugs 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 2
- 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
- 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
- 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
- 235000004279 alanine Nutrition 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
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000006260 foam Substances 0.000 description 11
- 229920002545 silicone oil Polymers 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000005375 organosiloxane group Polymers 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000007794 irritation Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000693 micelle Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 3
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 229920013822 aminosilicone Polymers 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000013923 monosodium glutamate Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940073490 sodium glutamate Drugs 0.000 description 2
- 229940045944 sodium lauroyl glutamate Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 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 2
- 238000001694 spray drying Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940048098 sodium sarcosinate Drugs 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Silicon Polymers (AREA)
Abstract
The invention provides an environment-friendly amino acid modified organic silicon surfactant, belonging to the field of preparation of organic silicon surfactants and amino acid surfactants. The organic silicon compound containing hydrogen functional groups and epoxy-terminated allyl polyether are catalyzed by a catalyst to obtain an epoxy-terminated polyether modified organic silicon compound, then the epoxy-terminated polyether modified organic silicon compound reacts with an amino acid monomer or an aqueous solution of amino acid sodium salt or amino acid potassium salt in an aqueous medium to obtain an aqueous solution of an amino acid modified organic silicon surfactant, and the aqueous solution is concentrated and dried to obtain the environment-friendly amino acid modified organic silicon surfactant. The amino acid monomer groups of the environment-friendly amino acid modified silicone surfactant can be diversified and selected according to actual needs, so that the environment-friendly amino acid modified silicone surfactant has the properties of different types of amino acid surfactants, and not only retains the spreadability and lower surface tension of the silicone surfactant, but also retains the characteristics of the mildness and excellent biodegradability of the amino acid surfactant.
Description
Technical Field
The invention belongs to the technical field of organic silicon surfactants and amino acid surfactants, and particularly relates to an environment-friendly amino acid modified organic silicon surfactant and a preparation method of the environment-friendly amino acid modified organic silicon surfactant.
Background
The amino acid surfactant is a mild degradable anionic surfactant, has rich and stable foam and mild property, can reduce the overall irritation of the formula, and is mainly applied to the fields of daily chemical products, medical supplies, nursing products and the like.
The organosilicon surfactant has the advantages of low surface tension, good wetting and spreading properties, large emulsifying effect and good compatibility, and can be widely applied to the fields of cosmetics, coatings, textiles, agricultural chemicals, medicines and the like.
Amino acid-modified silicone surfactants have some of the advantages of amino acid surfactants and silicone surfactants, leading to many possible industrial applications in the field of household cleaning or cosmetics or in the field of medical agriculture.
CN107787343A discloses a process for producing an organosilicon compound containing amino acid groups by reacting an organosilicon compound having epoxide units with an amino acid or a salt thereof in the presence of an alcohol. The method has the disadvantages that the compatibility of the raw materials and the organic solvent is good, water cannot be used as a reaction solvent, the use of a large amount of solvent causes the production process to be environment-unfriendly, and the trace residue of the solvent also limits the application field. CN107636048A and CN111004274A also have the same disadvantages.
CN111548501A discloses a preparation method of an amino acid-containing organosilicon surfactant, wherein polyether modified amino silicone oil reacts with acrylate or chloroacetate. The method has the defects that the amino structure in the polyether modified amino silicone oil is different from the amino structure in the amino acid monomer, and the requirement of structural property diversity of different amino acids cannot be met, so that the characteristics of a plurality of amino acids are hardly fully reflected. The same disadvantages are also found in the methods described in CN107698615A, CN107497365A, CN 107522726A.
Disclosure of Invention
The invention aims to provide an environment-friendly amino acid modified silicone surfactant, which solves the defects that the amino acid modified silicone surfactant in the prior art has single amino acid group and does not have diversified amino acid surfactants.
The second purpose of the invention is to provide a preparation method of the environment-friendly amino acid modified organosilicon surfactant.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
an environment-friendly amino acid modified silicone surfactant is an organosilicon compound which at least comprises one unit of a structural general formula I and a structural general formula II:
R-(CH3)2Si-O-[(CH3)2Si-O]P-(CH3)2Si-R (structural general formula I),
(CH3)3Si-O-[(CH3)2Si-O]a-[(CH3)SiR-O]b-Si(CH3)3(structural general formula II);
wherein R represents-R2-R1, wherein in the R group,
r1 represents an amino acid monomer group,
r2 represents a structural formula of CH2＝CH2CH2[OCH2(CH3)CH]m(OCH2CH2)nOCH2CHCH2O, one or more epoxy-terminated allyl polyether ring-opened and hydrosilylation groups;
m and n represent natural numbers of 1-100, p represents an integer of 1-100, a represents an integer of 0-100, and b represents an integer of 1-100.
Preferably, m + n ≦ 30; p takes an integer between 1 and 13; a takes an integer between 0 and 5; b is an integer between 1 and 3.
In the invention, the amino acid monomer group is one or a combination of glutamic acid, sarcosine, glycine, lysine, alanine, serine, tryptophan, tyrosine, histidine, valine, aspartic acid, arginine and proline.
In the invention, the environment-friendly amino acid modified organosilicon surfactant is obtained by the following method: the epoxy-terminated polyether modified organic silicon compound and an amino acid monomer or an amino acid sodium salt or an amino acid potassium salt react at a certain temperature in an aqueous medium to prepare the environment-friendly amino acid modified organic silicon surfactant.
Further, the aqueous medium is at least one of pure water, saline solution, acid-containing aqueous solution, alkali-containing aqueous solution, solvent-containing aqueous solution and surfactant-containing aqueous solution.
Further, the epoxy-terminated polyether modified organosilicon compound is obtained by reacting epoxy-terminated allyl polyether with a hydrogen-containing functional group organosilicon compound.
Further, the structural formula of the epoxy-terminated allyl polyether is CH2＝CH2CH2[OCH2(CH3)CH]m(OCH2CH2)nOCH2CHCH2O, the molecular weight of which is between 600 and 1200.
Preferably, the epoxy-terminated allyl polyether is a polyether having a molecular weight value of 1000.
The structural formula of the organic silicon compound containing the hydrogen functional group is H- (CH)3)2Si-O-[(CH3)2Si-O]P-(CH3)2Si-H, p takes an integer between 1 and 13; or the structural formula is (CH)3)3Si-O-[(CH3)2Si-O]a-[(CH3)SiH-O]b-Si(CH3)3A takes a natural number between 0 and 3, and b takes a natural number between 1 and 3.
Preferably, the organosilicon compound containing a hydrogen functional group is 1,1,1,3,5,5, 5-heptamethyltrisiloxane.
A preparation method of an environment-friendly amino acid modified organosilicon surfactant comprises the following steps:
(1) epoxy-terminated allyl polyether and an organic silicon compound containing a hydrogen functional group are subjected to a heating reaction under the presence of a catalyst to obtain an epoxy-terminated polyether modified organic silicon compound;
(2) preparing an aqueous solution of an amino acid monomer or an amino acid sodium salt or an amino acid potassium salt;
(3) dissolving the epoxy-terminated polyether modified organic silicon compound obtained in the step (1) in water to prepare an epoxy-terminated polyether modified organic silicon compound aqueous solution, and heating and reacting the epoxy-terminated polyether modified organic silicon compound aqueous solution with the amino acid monomer or amino acid sodium salt or amino acid potassium salt aqueous solution obtained in the step (2) in a nitrogen environment to obtain an amino acid modified organic silicon surfactant aqueous solution;
(4) and (4) drying or concentrating the amino acid modified organic silicon surfactant aqueous solution obtained in the step (3) to obtain the environment-friendly amino acid modified organic silicon surfactant.
The invention can be improved as follows, the reaction temperature in the step (1) is 120-160 ℃, and the reaction time is 0.5-3 hours.
Further, the catalyst is a Karstedt (Karstedt) catalyst, a Speier catalyst, a platinum complex. Preferably, the catalyst is a Speier catalyst.
In the step (2), the mass percentage concentration of the aqueous solution of the amino acid monomer or the sodium salt or the potassium salt of the amino acid is 20 to 30 percent.
Preferably, the mass percentage of the aqueous solution of the amino acid monomer or the sodium salt or the potassium salt of the amino acid is 20%.
In the step (3), the reaction temperature is 30-80 ℃, and the reaction time is 2-10 hours.
In the step (3) of the invention, the mass percentage concentration of the epoxy-terminated polyether modified organosilicon compound aqueous solution is 20-30%.
Preferably, the concentration of the epoxy-terminated polyether modified organosilicon compound in the water solution is 20% by mass.
In step (4) of the present invention, the drying is spray drying or freeze drying.
In the step (4) of the present invention, the concentration is reduced pressure distillation.
In the invention, the content of the environment-friendly amino acid modified silicone surfactant is 20-100%.
Furthermore, the environment-friendly amino acid modified silicone surfactant is in a solid state, a liquid state or a paste state.
The invention has the following beneficial effects:
(1) the amino acid monomer group of the environment-friendly amino acid modified silicone surfactant can be diversified and selected according to actual needs, so that the environment-friendly amino acid modified silicone surfactant has the performances of different types of amino acid surfactants.
(2) The amino acid modified organosilicon surfactant has a long chain formed by silicon-oxygen bonds, and simultaneously has amino acid monomer groups, so that the characteristics of easy spreadability and low surface tension of the organosilicon surfactant, and the characteristics of mildness and excellent biodegradability of the amino acid surfactant are retained.
(3) In the preparation process of the environment-friendly amino acid modified organic silicon surfactant, an aqueous medium is used as a solvent in the reaction process, the solvent can be pure water or aqueous solution of acid, alkali and salt, and an organic solvent can also be added, so that the environment-friendly amino acid modified organic silicon surfactant has no special requirement on the solvent, has a wider application range, and is simple in process and convenient to operate.
Detailed Description
Example 1
A preparation method of an environment-friendly amino acid modified organosilicon surfactant comprises the following steps:
(1) preparation of epoxy-terminated polyether-modified organosiloxane: adding 22.2 kg (100mol) of 1,1,1,3,5,5, 5-heptamethyltrisiloxane and 105 kg (105mol) of epoxy-terminated allyl polyether with the molecular weight of 1000 into a reaction kettle, stirring, heating to 130 ℃, adding Speier catalyst with the dosage of chloroplatinic acid of 3ppm, keeping the temperature for 3 hours, and cooling to obtain colorless and transparent epoxy-terminated polyether modified organosiloxane;
(2) preparation of aqueous glutamic acid sodium salt solution: dissolving 14.7 kg (100mol) of glutamic acid and 5.3 kg (132.5mol) of sodium hydroxide in 80 kg of water in sequence, and uniformly stirring to obtain 100 kg of colorless transparent 20% sodium glutamate saline solution;
(3) preparing a glutamic acid modified organic silicon surfactant aqueous solution: dissolving the epoxy-terminated polyether-modified organosiloxane prepared in the step (1) in 508.8 kg of water to obtain 636 kg of 20% epoxy-terminated polyether-modified organosiloxane aqueous solution; putting the product prepared in the step (2) into the reaction kettle, introducing nitrogen for protection, heating to 30-35 ℃ under reflux condensation, reacting for 1 hour, heating to 40-45 ℃, reacting for 1 hour, heating to 50-55 ℃, reacting for 1 hour, heating to 80-85 ℃, reacting for 2 hours, and cooling to obtain colorless to light yellow transparent glutamic acid modified organosilicon surfactant aqueous solution;
(4) preparing a glutamic acid modified organic silicon surfactant: and (4) spray-drying the product prepared in the step (3) to obtain a colorless to light yellow powdery glutamic acid modified silicone surfactant.
Example 2
A preparation method of an environment-friendly amino acid modified organosilicon surfactant comprises the following steps:
(1) preparation of epoxy-terminated polyether-modified organosiloxane: adding 22.2 kg (100mol) of 1,1,1,3,5,5, 5-heptamethyltrisiloxane and 105 kg (105mol) of epoxy-terminated allyl polyether with the molecular weight of 1000 into a reaction kettle, stirring, heating to 130 ℃, adding Speier catalyst with the dosage of chloroplatinic acid of 3ppm, keeping the temperature for 3 hours, and cooling to obtain colorless and transparent epoxy-terminated polyether modified organosiloxane;
(2) preparation of an aqueous lysine solution: dissolving 14.6(100mol) kg of lysine in 58.4 kg of water, and uniformly stirring to obtain 73 kg of colorless and transparent 20% lysine aqueous solution;
(3) preparation of lysine modified organosilicon surfactant aqueous solution: dissolving the epoxy-terminated polyether modified organosiloxane prepared in the step (1) in 508.8 kg of water to obtain 581.8 kg of 20% epoxy-terminated polyether modified organosiloxane aqueous solution; putting the product prepared in the step (2) into the reaction kettle, introducing nitrogen for protection, heating to 30-35 ℃ under reflux condensation, reacting for 1 hour, heating to 40-45 ℃, reacting for 1 hour, heating to 50-55 ℃, reacting for 1 hour, heating to 80-85 ℃, reacting for 2 hours, and cooling to obtain a colorless to light yellow transparent lysine modified organic silicon surfactant aqueous solution;
(4) preparation of lysine modified silicone surfactant: and (4) carrying out reduced pressure distillation on the product obtained in the step (3) to obtain a light yellow transparent liquid lysine modified organic silicon surfactant with the content of 30%.
Example 3
A preparation method of an environment-friendly amino acid modified organosilicon surfactant comprises the following steps:
(1) preparation of epoxy-terminated polyether modified silicone oil: adding 55.55 kg (100mol) of hydrogen-terminated silicone oil with the hydrogen content of 0.18 percent and 111.11 kg (100mol) of epoxy-terminated allyl polyether with the molecular weight of 1000 into a reaction kettle, starting stirring, heating to 150 ℃, adding a Speier catalyst with the dosage of chloroplatinic acid of 3ppm, keeping the temperature for 1 hour until the materials are transparent, and cooling to obtain colorless and transparent epoxy-terminated polyether modified silicone oil after keeping the temperature for 1 hour;
(2) preparation of sodium sarcosinate aqueous solution: dissolving 8.9(100mol) kg of sarcosine and 2(50mol) kg of sodium hydroxide in 43.6 kg of water in sequence, and uniformly stirring to obtain 54.5 kg of colorless and transparent 20% sarcosine sodium salt aqueous solution;
(3) preparation of sarcosine modified organosilicon surfactant aqueous solution: dissolving the epoxy-terminated polyether modified silicone oil prepared in the step (1) in 666.66 kg of water to obtain 833.3 kg of 20% epoxy-terminated polyether modified silicone oil aqueous solution; putting the product prepared in the step (2) into the reaction kettle, introducing nitrogen for protection, heating to 30-35 ℃ under reflux condensation, reacting for 1 hour, heating to 40-45 ℃, reacting for 1 hour, heating to 50-55 ℃, reacting for 1 hour, heating to 80-85 ℃, reacting for 2 hours, and cooling to obtain colorless to light yellow transparent sarcosine sodium salt modified organic silicon surfactant aqueous solution;
(4) preparation of sarcosine-modified silicone surfactant: and (4) distilling the product obtained in the step (3) under reduced pressure to obtain the sarcosine modified organosilicon surfactant with the content of 50% colorless to light yellow paste.
Example 4
A preparation method of an environment-friendly amino acid modified organosilicon surfactant comprises the following steps:
(1) preparation of epoxy-terminated polyether modified silicone oil: adding 55.55 kg (100mol) of hydrogen-terminated silicone oil with the hydrogen content of 0.18 percent and 111.11 kg (100mol) of epoxy-terminated allyl polyether with the molecular weight of 1000 into a reaction kettle, starting stirring, heating to 150 ℃, adding a Speier catalyst with the dosage of chloroplatinic acid of 3ppm, keeping the temperature for 1 hour until the materials are transparent, and cooling to obtain colorless and transparent epoxy-terminated polyether modified silicone oil after keeping the temperature for 1 hour;
(2) preparation of an aqueous glycine sodium salt solution: dissolving 7.5(100mol) kg of glycine and 1(25mol) kg of sodium hydroxide in 34 kg of water in sequence, and uniformly stirring to obtain 42.5 kg of colorless and transparent 20% glycine sodium salt aqueous solution;
(3) preparing a glycine modified organic silicon surfactant aqueous solution: dissolving the epoxy-terminated polyether modified silicone oil prepared in the step (1) in 666.66 kg of water to obtain 833.3 kg of 20% epoxy-terminated polyether modified silicone oil aqueous solution; putting the product prepared in the step (2) into the reaction kettle, introducing nitrogen for protection, refluxing and condensing, heating to 30-35 ℃, reacting for 1 hour, heating to 40-45 ℃, reacting for 1 hour, heating to 50-55 ℃, reacting for 1 hour, heating to 80-85 ℃, reacting for 2 hours, and cooling to obtain a colorless to light yellow transparent glycine sodium salt modified organosilicon surfactant aqueous solution;
(4) preparing a glycine modified organic silicon surfactant: and (4) carrying out freeze drying on the product prepared in the step (3) to prepare the glycine modified organic silicon surfactant with the content of 100% light yellow oil.
Performance testing
1. Preparation of sodium lauroyl glutamate solution and sodium lauryl sulfate
147g (1mol) of glutamic acid, 80g (2mol) of sodium hydroxide and 1038g of water are put into a flask, stirred and neutralized into a sodium glutamate aqueous solution, 218g (1mol) of lauroyl chloride is slowly dripped at room temperature (25 ℃), after dripping is finished for 3 hours, the reaction is continued for 3 hours at the temperature, and the sodium lauroyl glutamate aqueous solution with the content fraction of 30 percent is obtained.
Adding 37g of n-dodecanol into a flask, continuously stirring at 30-40 ℃, adding 20g of sulfamic acid and 4g of urea which are uniformly mixed by a mortar in batches, dropwise adding 3-5 drops of concentrated sulfuric acid after the mixture is uniformly dispersed, heating to 105-110 ℃, reacting for 1.5 hours, neutralizing with 20% of sodium hydroxide solution until the pH value is about 8, and vacuumizing to remove ammonia gas. Cooling, adding 300g of ethyl ether, fully dissolving, performing suction filtration to obtain sodium dodecyl sulfate crystals, and placing the sodium dodecyl sulfate crystals in an oven to dry for 8 hours at 50-60 ℃ to obtain the sodium dodecyl sulfate.
2. Foaming and foam stability test method
Preparing an aqueous solution with the mass fraction of 0.25%, weighing 5g, putting the aqueous solution into a 50ml test tube, shaking the test tube up and down for 10 times, placing the test tube on a test tube rack, and observing the instantaneous foam height and the foam height after 5 minutes. A high instantaneous foam height indicates good foamability, and a low foam indicates poor foamability; after 5 minutes a high foam height indicates good foam stability and a low foam indicates poor foam stability.
3. Lubricity test
Preparing an aqueous solution with the mass fraction of 30%, selecting 5 testers, dripping 0.05g of the aqueous solution to an arm of each tester, uniformly smearing the aqueous solution with fingers, drying the aqueous solution, touching the skin of the smeared part, and giving out lubricity data according to experience.
4. Irritation testing method
Preparing into 30% water solution, selecting 5 testers, applying 0.05g onto arm and behind ear, and observing difference between the applied part of skin and surrounding skin after one week. A large difference indicates high irritation, and a non-difference indicates low irritation.
5. Method for testing detergency
Preparing an aqueous solution with the mass fraction of 0.1%, taking out 100g of the aqueous solution and placing the 100g of aqueous solution in a 250ml beaker; taking 3 x 3cm of pure cotton white cloth, and dropwise adding 2 drops of a mixture consisting of ink, liquid paraffin, edible blend oil and soil. And (3) putting the white cloth in a beaker, starting a dispersion machine (rotating speed is 100r/min), taking out and drying after 10min, and observing residual stains on the white cloth, wherein less residual stains indicate good decontamination performance.
6. Method for testing surface tension and critical micelle concentration
The lowest surface tension and critical micelle concentration were measured with a K12 surface tensiometer.
The specific test results are shown in tables 1 and 2
TABLE 1 comparison of the properties of the amino acid-modified silicone surfactants prepared in the examples of the present invention and comparative examples
As can be seen from Table 1, the amino acid-modified silicone surfactants prepared in the examples of the present invention have excellent foaming, foam stabilizing, lubricating and low irritation properties.
TABLE 2 surface tension and critical micelle concentration of amino acid-modified silicone surfactants prepared in the examples of the present invention
As can be seen from Table 2, the amino acid-modified silicone surfactants prepared in the examples of the present invention have very low surface tension.
The above-described embodiments of the present invention are not intended to limit the scope of the present invention, and the embodiments of the present invention are not limited thereto, and various other modifications, substitutions and alterations can be made to the above-described embodiments of the present invention without departing from the basic technical concept of the present invention as defined by the general technical knowledge and common practice in the art.
Claims (10)
1. An environment-friendly amino acid modified silicone surfactant is an organosilicon compound which at least comprises one unit of a structural general formula I and a structural general formula II:
R-(CH3)2Si-O-[(CH3)2Si-O]P-(CH3)2Si-R (structural general formula I),
(CH3)3Si-O-[(CH3)2Si-O]a-[(CH3)SiR-O]b-Si(CH3)3(structural general formula II);
wherein R represents-R2-R1, wherein in the R group,
r1 represents an amino acid monomer group,
r2 represents a structural formula of CH2＝CH2CH2[OCH2(CH3)CH]m(OCH2CH2)nOCH2CHCH2O, one or more epoxy-terminated allyl polyether ring-opened and hydrosilylation groups;
m and n represent natural numbers of 1-100, p represents an integer of 1-100, a represents an integer of 0-100, and b represents an integer of 1-100.
2. The environment-friendly amino acid-modified silicone surfactant as claimed in claim 1, wherein m + n is 30 or less; p takes an integer between 1 and 13; a takes an integer between 0 and 5; b is an integer between 1 and 3.
3. The environment-friendly amino acid-modified silicone surfactant according to claim 1 or 2, wherein the amino acid monomer group is one or a combination of glutamic acid, sarcosine, glycine, lysine, alanine, serine, tryptophan, tyrosine, histidine, valine, aspartic acid, arginine and proline.
4. The environment-friendly amino acid modified silicone surfactant according to claim 1, obtained by: the epoxy-terminated polyether modified organic silicon compound and an amino acid monomer or an amino acid sodium salt or an amino acid potassium salt react at a certain temperature in an aqueous medium to prepare the environment-friendly amino acid modified organic silicon surfactant.
5. The environment-friendly amino acid-modified silicone surfactant as claimed in claim 4, wherein the epoxy-terminated polyether-modified silicone compound is obtained by reacting an epoxy-terminated allyl polyether with a hydrogen-containing functional group silicone compound.
6. The environment-friendly amino acid-modified silicone surfactant as claimed in claim 5, wherein the epoxy-terminated allyl polyether has a structural formula of CH2＝CH2CH2[OCH2(CH3)CH]m(OCH2CH2)nOCH2CHCH2O, the molecular weight of which is between 600 and 1200.
7. The environment-friendly amino acid-modified silicone surfactant as claimed in claim 5, wherein the hydrogen-functional group-containing organosilicon compound has a structural formula of H- (CH)3)2Si-O-[(CH3)2Si-O]P-(CH3)2Si-H, p takes an integer between 1 and 13; or the structural formula is (CH)3)3Si-O-[(CH3)2Si-O]a-[(CH3)SiH-O]b-Si(CH3)3A takes a natural number between 0 and 3, and b takes a natural number between 1 and 3.
8. The environment-friendly amino acid-modified silicone surfactant of claim 7, wherein the hydrogen-functional organosilicon compound is 1,1,1,3,5,5, 5-heptamethyltrisiloxane.
9. The preparation method of the environment-friendly amino acid modified organosilicon surfactant is characterized by comprising the following steps:
(1) epoxy-terminated allyl polyether and an organic silicon compound containing a hydrogen functional group are subjected to a heating reaction under the presence of a catalyst to obtain an epoxy-terminated polyether modified organic silicon compound;
(2) preparing an aqueous solution of an amino acid monomer or an amino acid sodium salt or an amino acid potassium salt;
(3) dissolving the epoxy-terminated polyether modified organic silicon compound obtained in the step (1) in water to prepare an epoxy-terminated polyether modified organic silicon compound aqueous solution, and heating and reacting the epoxy-terminated polyether modified organic silicon compound aqueous solution with the amino acid monomer or amino acid sodium salt or amino acid potassium salt aqueous solution obtained in the step (2) in a nitrogen environment to obtain an amino acid modified organic silicon surfactant aqueous solution;
(4) and (4) drying or concentrating the amino acid modified organic silicon surfactant aqueous solution obtained in the step (3) to obtain the environment-friendly amino acid modified organic silicon surfactant.
10. The method for preparing environment-friendly amino acid modified silicone surfactant as recited in claim 9 wherein in step (1) the reaction temperature is 120-160 ℃ and the reaction time is 0.5-3 hours; the catalyst is Karstedt (Karstedt) catalyst, Speier catalyst and platinum complex; in the step (3), the reaction temperature is 30-80 ℃, and the reaction time is 2-10 hours.
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| CN101918475A (en) * | 2007-12-27 | 2010-12-15 | 道康宁东丽株式会社 | Produce the method for amino-acid modified organopolysiloxane emulsion |
| CN111004274A (en) * | 2019-12-04 | 2020-04-14 | 常熟理工学院 | Cyclosiloxane modified glutamic acid and preparation method thereof |
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| US20070086968A1 (en) * | 2005-10-13 | 2007-04-19 | Leatherman Mark D | Hydrolysis resistant organomodified disiloxane surfactants |
| CN101918475A (en) * | 2007-12-27 | 2010-12-15 | 道康宁东丽株式会社 | Produce the method for amino-acid modified organopolysiloxane emulsion |
| CN111004274A (en) * | 2019-12-04 | 2020-04-14 | 常熟理工学院 | Cyclosiloxane modified glutamic acid and preparation method thereof |
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