CN108948068B - Preparation method of alkyl imidazoline organosilicon quaternary ammonium salt - Google Patents
Preparation method of alkyl imidazoline organosilicon quaternary ammonium salt Download PDFInfo
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- CN108948068B CN108948068B CN201810813959.5A CN201810813959A CN108948068B CN 108948068 B CN108948068 B CN 108948068B CN 201810813959 A CN201810813959 A CN 201810813959A CN 108948068 B CN108948068 B CN 108948068B
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- -1 alkyl imidazoline Chemical compound 0.000 title claims abstract description 103
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 238000010438 heat treatment Methods 0.000 claims abstract description 31
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 29
- 239000000194 fatty acid Substances 0.000 claims abstract description 29
- 229930195729 fatty acid Natural products 0.000 claims abstract description 29
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000001035 drying Methods 0.000 claims abstract description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 16
- 239000008096 xylene Substances 0.000 claims abstract description 16
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000007112 amidation reaction Methods 0.000 claims abstract description 8
- 238000001704 evaporation Methods 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 238000005956 quaternization reaction Methods 0.000 claims abstract description 8
- 238000005303 weighing Methods 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 claims description 5
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005639 Lauric acid Substances 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims 1
- 210000003746 feather Anatomy 0.000 abstract description 28
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 244000005700 microbiome Species 0.000 abstract description 4
- 230000005611 electricity Effects 0.000 abstract description 2
- 230000003068 static effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000000835 fiber Substances 0.000 description 7
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 5
- 230000001804 emulsifying effect Effects 0.000 description 5
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 5
- 230000007547 defect Effects 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 3
- 244000063299 Bacillus subtilis Species 0.000 description 3
- 235000014469 Bacillus subtilis Nutrition 0.000 description 3
- 241000222122 Candida albicans Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000008233 hard water Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000005202 decontamination Methods 0.000 description 2
- 230000003588 decontaminative effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- WSFMFXQNYPNYGG-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC WSFMFXQNYPNYGG-UHFFFAOYSA-M 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- 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
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M19/00—Treatment of feathers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Inorganic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a preparation method of alkyl imidazoline organosilicon quaternary ammonium salt, which comprises the following steps: s1: amidation reaction: weighing long-chain alkyl fatty acid, diethylenetriamine and xylene, and heating for reaction for 6-8 h; s2: cyclization reaction: heating, continuing to react for 4-6h, ending the reaction, cooling to 120 ℃, evaporating residual xylene to obtain a light yellow liquid, recrystallizing for 3 times by using acetone to obtain a white solid, and drying to obtain a white powder to obtain alkyl imidazoline; s3: quaternization reaction: adding the alkyl imidazoline prepared in the S2, the halogenated organosilane and the catalyst into a solvent, carrying out microwave heating reaction for 60-70min, carrying out reduced pressure distillation after the reaction is finished, removing the solvent, and drying to obtain solid powder. The alkyl imidazoline organosilicon quaternary ammonium salt prepared by the invention has high yield of 62.4-68.5%. The product is applied to the antibacterial fluffing finishing agent for the feather (down), can effectively inhibit various microorganisms, can improve the fluffy degree of the feather (down) and can reduce the static electricity of the feather (down).
Description
Technical Field
The invention relates to the technical field of organic synthesis, and particularly relates to a preparation method of alkyl imidazoline organosilicon quaternary ammonium salt.
Background
The imidazoline surfactant is a surfactant with excellent performance, has mild property, good decontamination, hard water resistance, foaming and emulsifying properties, particularly has extremely low toxicity, extremely low irritation to skin and eyes, good foaming property, excellent emulsifying property and good biodegradability, has very wide application prospect in the fields of daily chemical industry, spinning, printing and dyeing, medical sanitation, petroleum mining and the like, and has low toxicity, hard water resistance, foaming and emulsifying properties. The defects are that the imidazoline quaternary ammonium salt is not high in temperature resistance and easy to hydrolyze, and imidazoline quaternary ammonium salt obtained by quaternizing imidazoline can improve stability of imidazoline and water solubility of imidazoline.
The quaternizing agents used for synthesizing imidazoline quaternary ammonium salts reported in the literature at present are dimethyl sulfate, methyl chloride, benzyl chloride, epichlorohydrin, chlorohydrin and the like. However, these quaternizing agents are toxic and have poor temperature resistance. The organosilicon surfactant contains both long-chain alkyl and inorganic Si element, so that it not only has high surface activity of general surfactant, but also has SiO2The paint has excellent performances of high and low temperature resistance, weather resistance, no toxicity, no corrosion, stable property and the like. The organosilicon quaternary ammonium salt surfactant has wide application in the fields of textile industry, daily chemical industry, coating, plastics, pesticides, metal corrosion inhibition and the like. However, the currently widely used organosilicon quaternary ammonium salt is mainly (trimethoxysilylpropyl) octadecyl dimethyl ammonium chloride (DC-SQ-5700) developed by International Korea Corning company in 1967, and the product has excellent performance, but is expensive and difficult to biodegrade, and does not accord with the direction of green development and ecological development vigorously advocated by the current state.
Therefore, the invention aims to overcome the defects of the prior imidazoline surfactant and organosilicon quaternary ammonium salt surfactant and prepare the novel alkyl imidazoline organosilicon quaternary ammonium salt.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides a preparation method of alkyl imidazoline organic silicon quaternary ammonium salt, which has the good emulsifying property of alkyl imidazoline and the good thermal stability of organic silicon quaternary ammonium salt, and can be widely used as a cleaning agent, an emulsifying agent and a good softening agent and a durable bactericide of synthetic fibers.
A preparation method of alkyl imidazoline organosilicon quaternary ammonium salt comprises the following steps: s1: amidation reaction: weighing long-chain alkyl fatty acid, diethylenetriamine and xylene, introducing nitrogen, and heating for reaction for 6-8 h;
s2: cyclization reaction: heating, continuing to react for 4-6h, ending the reaction, cooling to 120 ℃, evaporating residual xylene to obtain a light yellow liquid, recrystallizing for 3 times by using acetone to obtain a white solid, and drying to obtain a white powder to obtain alkyl imidazoline;
s3: quaternization reaction: adding the alkyl imidazoline prepared in the S2, the halogenated organosilane and the catalyst into a solvent, carrying out microwave heating reaction for 60-70min, carrying out reduced pressure distillation after the reaction is finished, removing the solvent, and drying to obtain solid powder.
Preferably, the mole ratio of the long-chain alkyl fatty acid to the diethylenetriamine in the S1 is 1: (1.1-1.2), the addition amount of the dimethylbenzene is 70-80% of the total mass of the long-chain alkyl fatty acid and the diethylenetriamine, and the reaction temperature is 155-170 ℃.
Preferably, the long-chain alkyl fatty acid is lauric acid, myristic acid, palmitic acid or stearic acid.
Preferably, the cyclization temperature in S2 is 220-240 ℃.
Preferably, the molar ratio of the alkyl imidazoline, the halogenated organosilane and the catalyst in S3 is 1: (1.1-1.5): (0.1-0.3), and the addition amount of the solvent is 1.5-2 times of the total mass of the alkyl imidazoline, the halogenated organosilane and the catalyst.
Preferably, the halogenated organosilane in the S3 is gamma-chloropropyltrimethoxysilane or gamma-chloropropylmethyldimethoxysilane; the catalyst is KI or NaI; the solvent is N, N-dimethylformamide or dimethyl sulfoxide.
Preferably, the microwave heating power in S3 is 800W, and the reaction temperature is 155-165 ℃.
The preparation reaction formula of the 2-alkyl imidazoline organosilicon quaternary ammonium salt provided by the invention is as follows:
the action principle is as follows:
the Si atom in the molecular structure of the organosilicon quaternary ammonium salt is often connected with 3-OCH3And the reaction activity is high, and when the catalyst is diluted by water, the methoxyl is hydrolyzed to form silanol. When it encounters a fabric, it bonds to the fibers in two ways: firstly, electrostatic bonding, namely positive charge N + in molecules is attracted by the fiber surface with negative charge, and intermolecular dehydration condensation is carried out simultaneously to form a covering film on the fiber surface, and the defects are that the bonding strength is weak and the effect cannot be durable; secondly, alcohol groups generated by hydrolysis are combined with-OH on the surface of the fiber at 120 ℃, and intermolecular dehydration condensation is carried out to firmly combine the alcohol groups on the surface of the fiber in a covalent bond form. Therefore, the organosilicon quaternary ammonium salt forms an antimicrobial surface film with excellent durability by combining covalent bond and electrostatic adsorption. In addition, the positive charge N + of the quaternary ammonium salt is positioned at the outer side, so that positive ions can be generated, and the textile also has antistatic property.
The alkyl imidazoline type organosilicon quaternary ammonium salt integrates good decontamination, hard water resistance, mild property, excellent foaming and emulsifying properties of alkyl imidazoline and good thermal stability of organosilicon, overcomes the respective defects of two types of surfactants, and can be widely used as a cleaning agent, an emulsifier, a lubricant and an excellent softener, an antistatic agent and a durable bactericide of synthetic fibers. The organosilicon quaternary ammonium salt can be used for hydrophilic finishing of fabrics, and endows the fabrics with good water absorption, sweat absorption, softness, smoothness, rebound resilience and antistatic property.
Compared with the prior art, the invention has the beneficial effects that:
according to the preparation method of the alkyl imidazoline organosilicon quaternary ammonium salt, halogenated organosilane is used as a quaternizing agent to quaternize alkyl imidazoline, and compared with a traditional quaternizing agent dimethyl sulfate and halogenated hydrocarbon, the obtained product alkyl imidazoline organosilicon quaternary ammonium salt has better high and low temperature resistance, weather resistance and long-acting antibacterial property than the traditional alkyl imidazoline quaternary ammonium salt. Compared with ester-based organosilicon quaternary ammonium salt, the preparation process of the alkyl imidazoline organosilicon quaternary ammonium salt is simpler, and the conversion rate of raw materials and the yield of products are higher. The conversion rate of the raw material is 85.3-88.6%, and the yield of the product is 62.4-68.5%.
The alkyl imidazoline organosilicon quaternary ammonium salt prepared by the invention is used for the feather (down) antibacterial fluffy finishing agent, can durably resist and inhibit various microorganisms, and comprises the following components: candida albicans, Aspergillus niger, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, etc. The product can not only remove original odor of feather (down) etc., but also prevent odor caused by mildew and rot due to corrosion of microorganism during storage, transportation, reprocessing and use.
The product prepared by the invention can quickly permeate into the feather (down) to enable the feather (down) to be tough, elastic, smooth and fluffy, and the fluffy degree of the down can be improved by more than 10% through detection; in addition, the product is positively charged and can be combined with negative ions in feather (down) fibers to reduce the static electricity of the feather (down).
Detailed Description
The present invention will be further illustrated with reference to the following specific examples.
Example 1
A preparation method of alkyl imidazoline organosilicon quaternary ammonium salt comprises the following steps:
s1: amidation reaction: weighing long-chain alkyl fatty acid, diethylenetriamine and xylene, heating and reacting for 6 hours, introducing nitrogen, and controlling the reaction temperature to 155 ℃; the molar ratio of the long-chain alkyl fatty acid to the diethylenetriamine is 1: 1.1, the addition amount of the dimethylbenzene is 70 percent of the total mass of the long-chain alkyl fatty acid and the diethylenetriamine, and the long-chain alkyl fatty acid is lauric acid.
S2: cyclization reaction: heating to 220 ℃ and continuing to react for 4h, finishing the reaction, cooling to 120 ℃, evaporating residual xylene to obtain a light yellow liquid, recrystallizing for 3 times by using acetone to obtain a white solid, drying to obtain white powder to obtain alkyl imidazoline, wherein the yield of the long-chain alkyl imidazoline is 86.7%;
s3: quaternization reaction: adding the alkyl imidazoline prepared in the S2, the halogenated organosilane and the catalyst into a solvent, and carrying out microwave heating reaction for 60min at the microwave heating power of 800W and the reaction temperature of 155 ℃. After the reaction is finished, distilling the solvent under reduced pressure, and drying to obtain solid powder; the content of the alkyl imidazoline organosilicon quaternary ammonium salt is determined by a bromophenol blue method, and the yield is 68.5%.
The molar ratio of alkyl imidazoline, halogenated organosilane and catalyst is 1: 1.1: 0.1, the addition amount of the solvent is 1.5 times of the total mass of the alkyl imidazoline, the halogenated organosilane and the catalyst. The halogenated organosilane is gamma-chloropropyl trimethoxy silane; the catalyst is KI; the solvent is N, N-dimethylformamide.
Example 2
A preparation method of alkyl imidazoline organosilicon quaternary ammonium salt comprises the following steps:
s1: amidation reaction: weighing long-chain alkyl fatty acid, diethylenetriamine and xylene, heating and reacting for 7 hours, introducing nitrogen, and controlling the reaction temperature to 160 ℃; the molar ratio of the long-chain alkyl fatty acid to the diethylenetriamine is 1: 1.2, the addition amount of the dimethylbenzene is 75 percent of the total mass of the long-chain alkyl fatty acid and the diethylenetriamine, and the long-chain alkyl fatty acid is myristic acid.
S2: cyclization reaction: heating to 230 ℃ and continuing to react for 5 hours, finishing the reaction, cooling to 120 ℃, evaporating residual xylene to obtain a light yellow liquid, recrystallizing for 3 times by using acetone to obtain a white solid, drying to obtain white powder to obtain alkyl imidazoline, wherein the yield of the long-chain alkyl imidazoline is 85.3%;
s3: quaternization reaction: adding the alkyl imidazoline prepared in the S2, the halogenated organosilane and the catalyst into a solvent, and carrying out microwave heating reaction for 65min at the microwave heating power of 800W and the reaction temperature of 160 ℃. After the reaction is finished, distilling the solvent under reduced pressure, and drying to obtain solid powder; the content of the alkyl imidazoline organosilicon quaternary ammonium salt is measured by a bromophenol blue method, and the yield is 63.8%.
The molar ratio of alkyl imidazoline, halogenated organosilane and catalyst is 1: 1.3: 0.2, the addition amount of the solvent is 2 times of the total mass of the alkyl imidazoline, the halogenated organosilane and the catalyst. The halogenated organosilane is gamma-chloropropyl methyl dimethoxy silane; the catalyst is NaI; the solvent is dimethyl sulfoxide.
Example 3
A preparation method of alkyl imidazoline organosilicon quaternary ammonium salt comprises the following steps:
s1: amidation reaction: weighing long-chain alkyl fatty acid, diethylenetriamine and xylene, heating and reacting for 7.5h, introducing nitrogen, and controlling the reaction temperature to 165 ℃; the molar ratio of the long-chain alkyl fatty acid to the diethylenetriamine is 1: 1.15, the addition amount of the dimethylbenzene is 80 percent of the total mass of the long-chain alkyl fatty acid and the diethylenetriamine, and the long-chain alkyl fatty acid is palmitic acid.
S2: cyclization reaction: heating to 235 ℃, continuing to react for 6 hours, finishing the reaction, cooling to 120 ℃, evaporating residual xylene to obtain a light yellow liquid, recrystallizing for 3 times by using acetone to obtain a white solid, drying to obtain a white powder, obtaining alkyl imidazoline, wherein the yield of the long-chain alkyl imidazoline is 87.2%;
s3: quaternization reaction: adding the alkyl imidazoline prepared in the S2, the halogenated organosilane and the catalyst into a solvent, and carrying out microwave heating reaction for 70min, wherein the microwave heating power is 800W, and the reaction temperature is 165 ℃. After the reaction is finished, distilling the solvent under reduced pressure, and drying to obtain solid powder; the content of the alkyl imidazoline organosilicon quaternary ammonium salt is determined by a bromophenol blue method, and the yield is 66.7%.
The molar ratio of alkyl imidazoline, halogenated organosilane and catalyst is 1: 1.5: 0.3, the addition amount of the solvent is 1.8 times of the total mass of the alkyl imidazoline, the halogenated organosilane and the catalyst. The halogenated organosilane is gamma-chloropropyl trimethoxy silane; the catalyst is KI; the solvent is N, N-dimethylformamide.
Example 4
A preparation method of alkyl imidazoline organosilicon quaternary ammonium salt comprises the following steps:
s1: amidation reaction: weighing long-chain alkyl fatty acid, diethylenetriamine and xylene, heating and reacting for 8 hours, introducing nitrogen, and controlling the reaction temperature to 170 ℃; the molar ratio of the long-chain alkyl fatty acid to the diethylenetriamine is 1: 1.1, the addition amount of the dimethylbenzene is 70 percent of the total mass of the long-chain alkyl fatty acid and the diethylenetriamine, and the long-chain alkyl fatty acid is stearic acid.
S2: cyclization reaction: heating to 240 ℃ and continuing to react for 6 hours, finishing the reaction, cooling to 120 ℃, evaporating residual xylene to obtain a light yellow liquid, recrystallizing for 3 times by using acetone to obtain a white solid, drying to obtain white powder to obtain alkyl imidazoline, wherein the yield of the long-chain alkyl imidazoline is 88.6%;
s3: quaternization reaction: adding the alkyl imidazoline prepared in the S2, the halogenated organosilane and the catalyst into a solvent, and carrying out microwave heating reaction for 62min, wherein the microwave heating power is 800W, and the reaction temperature is 158 ℃. After the reaction is finished, distilling the solvent under reduced pressure, and drying to obtain solid powder; the content of the alkyl imidazoline organosilicon quaternary ammonium salt is determined by a bromophenol blue method, and the yield is 67.1%.
The molar ratio of alkyl imidazoline, halogenated organosilane and catalyst is 1: 1.1: 0.3, the addition amount of the solvent is 1.5 times of the total mass of the alkyl imidazoline, the halogenated organosilane and the catalyst. The halogenated organosilane is gamma-chloropropyl methyl dimethoxy silane; the catalyst is NaI; the solvent is N, N-dimethylformamide.
Example 5
A preparation method of alkyl imidazoline organosilicon quaternary ammonium salt comprises the following steps:
s1: amidation reaction: weighing long-chain alkyl fatty acid, diethylenetriamine and xylene, heating and reacting for 6 hours, introducing nitrogen, and controlling the reaction temperature to 155 ℃; the molar ratio of the long-chain alkyl fatty acid to the diethylenetriamine is 1: 1.2, the addition amount of the dimethylbenzene is 77 percent of the total mass of the long-chain alkyl fatty acid and the diethylenetriamine, and the long-chain alkyl fatty acid is lauric acid.
S2: cyclization reaction: heating to 220 ℃ and continuing to react for 4h, finishing the reaction, cooling to 120 ℃, evaporating residual xylene to obtain a light yellow liquid, recrystallizing for 3 times by using acetone to obtain a white solid, drying to obtain white powder to obtain alkyl imidazoline, wherein the yield of the long-chain alkyl imidazoline is 85.9%;
s3: quaternization reaction: adding the alkyl imidazoline prepared in the S2, the halogenated organosilane and the catalyst into a solvent, and carrying out microwave heating reaction for 68min, wherein the microwave heating power is 800W, and the reaction temperature is 162 ℃. After the reaction is finished, distilling the solvent under reduced pressure, and drying to obtain solid powder; the content of the alkyl imidazoline organosilicon quaternary ammonium salt is determined by a bromophenol blue method, and the yield is 62.4%.
The molar ratio of alkyl imidazoline, halogenated organosilane and catalyst is 1: 1.5: 0.1, the addition amount of the solvent is 2 times of the total mass of the alkyl imidazoline, the halogenated organosilane and the catalyst. The halogenated organosilane is gamma-chloropropyl trimethoxy silane; the catalyst is NaI; the solvent is dimethyl sulfoxide.
Product performance test
The alkyl imidazoline organosilicon quaternary ammonium salt synthesized in the examples 1 to 5 is used as the feather (down) antibacterial fluffing finishing agent.
The using method comprises the following steps: the product is added during the after-finishing of feather (down) (after the final rinsing of the feather, water is adjusted to enable the feather to be taken by a water extractor, about the ratio of the feather to the water is 130), and the adding amount is recommended to be 1.5 percent of the mass of the water in the feather washing machine or 4-5 percent of the weight of the feather. The feather belt drying method comprises the steps of putting the feather belt into a plastic barrel, adding a proper amount of water to dilute and stir uniformly, then adding the feather belt into a stirring wool washing machine, soaking for about 15-20 minutes after uniformly mixing, then sending the feather belt into a dehydrator (the water rate of the feather belt is controlled to be 50-70%), then sending the feather belt into a drying box to dry (the feather belt stays for about 10 minutes at the temperature of 100-120 ℃), and then cooling and packaging. The feather (down) treated by the synthesized alkyl imidazoline organosilicon quaternary ammonium salt has the following characteristics:
1. the bacteriostatic performance and the result are shown in table 1.
TABLE 1 results of bacteriostasis
| Group of | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 |
| Candida albicans | ++ | ++ | ++ | ++ | ++ |
| Aspergillus niger | ++ | ++ | ++ | ++ | ++ |
| Escherichia coli | ++ | ++ | ++ | ++ | ++ |
| Pseudomonas aeruginosa | ++ | ++ | ++ | ++ | ++ |
| Staphylococcus aureus | ++ | ++ | ++ | ++ | ++ |
| Bacillus subtilis | ++ | ++ | ++ | ++ | ++ |
Note: "+" indicates partial bacteriostasis, the bacteriostasis ring can be seen, but partial colony still grows in the ring; "+ +" indicates significant inhibition, with significant zone of inhibition, and no colony in the zone.
Methoxy in organosilicon in the product can be hydrolyzed to form silicon hydroxyl when meeting water, hydroxyl can be chemically bonded with hydroxyl, amido, carboxyl and the like in protein fibers such as feather (down), and the treated feather (down) can durably resist and inhibit various microorganisms, including: candida albicans, Aspergillus niger, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, etc. After normal washing for 20 times, the antibacterial and bacteriostatic agent still has high-efficiency antibacterial and bacteriostatic effects, and the antibacterial and bacteriostatic rate can reach more than 99%.
2. The bulk properties, results are shown in table 2.
TABLE 2 results of the experiment
| Group of | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 |
| Rate of increase in bulk | 12.5％ | 15.3％ | 14.6％ | 13.8％ | 15.1％ |
The product prepared by the invention can quickly permeate into the feather (down) to enable the feather (down) to be tough, elastic, smooth and fluffy, and the fluffy degree of the down can be improved by more than 10% through detection.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (6)
1. The preparation method of the alkyl imidazoline organosilicon quaternary ammonium salt is characterized by comprising the following steps:
s1: amidation reaction: weighing long-chain alkyl fatty acid, diethylenetriamine and xylene, introducing nitrogen, and heating for reaction for 6-8 h;
s2: cyclization reaction: heating, continuing to react for 4-6h, ending the reaction, cooling to 120 ℃, evaporating residual xylene to obtain a light yellow liquid, recrystallizing for 3 times by using acetone to obtain a white solid, and drying to obtain a white powder to obtain alkyl imidazoline;
s3: quaternization reaction: adding the alkyl imidazoline prepared in the S2, the halogenated organosilane and the catalyst into a solvent, carrying out microwave heating reaction for 60-70min, carrying out reduced pressure distillation after the reaction is finished, removing the solvent, and drying to obtain solid powder;
the long-chain alkyl fatty acid in the step S1 is lauric acid, myristic acid, palmitic acid or stearic acid;
the halogenated organosilane in the S3 is gamma-chloropropyl trimethoxy silane or gamma-chloropropyl methyl dimethoxy silane; the catalyst is KI or NaI; the solvent is N, N-dimethylformamide or dimethyl sulfoxide;
the general formula of the alkyl imidazoline organosilicon quaternary ammonium salt is as follows:
Or
2. The method for preparing the alkyl imidazoline organosilicon quaternary ammonium salt according to claim 1, wherein the molar ratio of the long-chain alkyl fatty acid in the S1 to diethylenetriamine is 1: (1.1-1.2), the addition amount of the dimethylbenzene is 70-80% of the total mass of the long-chain alkyl fatty acid and the diethylenetriamine, and the reaction temperature is 155-170 ℃.
3. The method as claimed in claim 1, wherein the cyclization temperature of S2 is 220-240 ℃.
4. The method for preparing the alkyl imidazoline organosilicon quaternary ammonium salt according to the claim 1, wherein the molar ratio of the alkyl imidazoline, the halogenated organosilane and the catalyst in the S3 is 1: (1.1-1.5): (0.1-0.3), and the addition amount of the solvent is 1.5-2 times of the total mass of the alkyl imidazoline, the halogenated organosilane and the catalyst.
5. The method as claimed in claim 1, wherein the microwave heating power in S3 is 800W, and the reaction temperature is 155-165 ℃.
6. The alkyl imidazoline silicone quaternary ammonium salt prepared by the preparation method of any one of claims 1 to 5.
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