CN112480163A - Organosilicon quaternary ammonium salt, preparation method and application thereof - Google Patents
Organosilicon quaternary ammonium salt, preparation method and application thereof Download PDFInfo
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- CN112480163A CN112480163A CN202110041903.4A CN202110041903A CN112480163A CN 112480163 A CN112480163 A CN 112480163A CN 202110041903 A CN202110041903 A CN 202110041903A CN 112480163 A CN112480163 A CN 112480163A
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- quaternary ammonium
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- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 78
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 150000002500 ions Chemical class 0.000 claims abstract description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
- 235000019864 coconut oil Nutrition 0.000 claims description 27
- 239000003240 coconut oil Substances 0.000 claims description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 27
- 239000000194 fatty acid Substances 0.000 claims description 27
- 229930195729 fatty acid Natural products 0.000 claims description 27
- 150000004665 fatty acids Chemical class 0.000 claims description 20
- 238000006482 condensation reaction Methods 0.000 claims description 19
- 125000003438 dodecyl group Chemical group [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])* 0.000 claims description 19
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 18
- WNLWBCIUNCAMPH-UHFFFAOYSA-N 2-n,2-n-dimethylpropane-1,2-diamine Chemical compound NCC(C)N(C)C WNLWBCIUNCAMPH-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 229920001296 polysiloxane Polymers 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 239000005639 Lauric acid Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000007810 chemical reaction solvent Substances 0.000 claims description 8
- 229910000077 silane Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 125000000913 palmityl 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])[H] 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000009988 textile finishing Methods 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 29
- 238000004659 sterilization and disinfection Methods 0.000 abstract description 11
- 230000001954 sterilising effect Effects 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 3
- 229920000229 biodegradable polyester Polymers 0.000 abstract 1
- 239000004622 biodegradable polyester Substances 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 32
- 230000003385 bacteriostatic effect Effects 0.000 description 26
- 238000002156 mixing Methods 0.000 description 24
- -1 silicon quaternary ammonium salt Chemical class 0.000 description 21
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 16
- 238000004090 dissolution Methods 0.000 description 13
- 229910052710 silicon Inorganic materials 0.000 description 12
- 239000010703 silicon Substances 0.000 description 12
- 241000222122 Candida albicans Species 0.000 description 7
- 241000191967 Staphylococcus aureus Species 0.000 description 7
- 229940095731 candida albicans Drugs 0.000 description 7
- 238000007865 diluting Methods 0.000 description 7
- GLISZRPOUBOZDL-UHFFFAOYSA-N 3-bromopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCBr GLISZRPOUBOZDL-UHFFFAOYSA-N 0.000 description 4
- NILZGRNPRBIQOG-UHFFFAOYSA-N 3-iodopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCI NILZGRNPRBIQOG-UHFFFAOYSA-N 0.000 description 4
- NYYGRSUHVRJFAO-UHFFFAOYSA-N [Cl-].C(CC)[NH3+].CO[Si](OC)OC Chemical compound [Cl-].C(CC)[NH3+].CO[Si](OC)OC NYYGRSUHVRJFAO-UHFFFAOYSA-N 0.000 description 4
- YVLHRYOHNHUVOA-UHFFFAOYSA-N 2,2-dimethylpropane-1,1-diamine Chemical compound CC(C)(C)C(N)N YVLHRYOHNHUVOA-UHFFFAOYSA-N 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000017858 Laurus nobilis Nutrition 0.000 description 2
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 2
- 244000125380 Terminalia tomentosa Species 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- YRBZVIZICUBRSA-UHFFFAOYSA-N 3-trimethoxysilylpropylazanium;bromide Chemical compound [Br-].CO[Si](OC)(OC)CCC[NH3+] YRBZVIZICUBRSA-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000675 fabric finishing Substances 0.000 description 1
- 238000009962 finishing (textile) Methods 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZQBVUULQVWCGDQ-UHFFFAOYSA-N propan-1-ol;propan-2-ol Chemical compound CCCO.CC(C)O ZQBVUULQVWCGDQ-UHFFFAOYSA-N 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 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
-
- 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
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/04—Disinfection
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Zoology (AREA)
- Inorganic Chemistry (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Hydrology & Water Resources (AREA)
- Environmental Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an organosilicon quaternary ammonium salt, a preparation method and application thereof, wherein the organosilicon quaternary ammonium salt has the following structural formula: [ R ]1‑CO‑NH‑CH2‑CH2‑CH2‑N（CH3）2‑CH2‑CH2‑CH2‑Si（OR2）3]X, wherein R1Is a C12-C22 fatty alkyl radical, R2Is methyl or ethyl, and X is Cl ion, Br ion or I ion. Compared with the organosilicon quaternary ammonium salt on the market, the organosilicon quaternary ammonium salt provided by the invention has the advantages that the amido bond is generatedThe biodegradable polyester film has the advantages of better degradability, more environmental friendliness, better water solubility and equivalent or better sterilization/antibacterial capability. The diluted solution is used for antibacterial finishing of fabrics and antibacterial/sterilization of public places such as hospitals, kindergartens, schools, markets and the like; it may also be used in other sterilization settings including, but not limited to, water treatment, etc. And the raw materials are easy to obtain, the reaction is mild, and three wastes are not discharged.
Description
Technical Field
The invention relates to the field of antibiosis/sterilization, in particular to an organosilicon quaternary ammonium salt, a preparation method and application thereof.
Background
At present, there are many kinds of sterilization chemicals which are applied in China, and each has various advantages and characteristics. The organosilicon quaternary ammonium salt is used as a high-efficiency, safe, nontoxic and harmless functional antibacterial finishing agent, and is widely applied to the industries of medicine, textile, cosmetics and the like. The organic silicon quaternary ammonium salt fabric finishing agent is particularly suitable for antibacterial finishing and general finishing of fabrics, and the fabrics finished by the organic silicon quaternary ammonium salt not only have excellent antibacterial performance, but also have good antistatic performance, and simultaneously have water absorption and sweat absorption properties, smooth softness, rebound resilience and the like. It is also especially suitable for the antibacterial disinfection in public places such as hospitals, kindergartens, schools and markets; and is particularly suitable for water treatment and other aspects of antibacterial/bactericidal treatment.
The organosilicon quaternary ammonium salt is generally prepared by reacting C12-C22 alkyl tertiary amine with halogenated propyl alkoxy silane in a solvent under the action of a catalyst. In the production process of the alkyl tertiary amine, a fatty acid cyanidation reaction and a hydrogenation process are required, so that the alkyl tertiary amine is not easy to obtain and has high safety requirement. Moreover, because the hydrophobic property of the long-chain alkyl is very strong, the water solubility of the product is poor, the product is not suitable for high-concentration use, and solvents such as methanol, ethanol and the like are required to be used simultaneously.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to overcome the defect of poor water solubility of the organosilicon quaternary ammonium salt in the prior art, thereby providing the organosilicon quaternary ammonium salt.
The invention also provides a preparation method of the organic silicon quaternary ammonium salt, aiming at overcoming the defects of difficult obtainment and high safety requirement in the preparation process of the organic silicon quaternary ammonium salt in the prior art.
In order to solve the problems, the invention provides a quaternary ammonium salt of organosilicon, which has the following structural formula:
[R1-CO-NH-CH2-CH2-CH2-N（CH3）2-CH2-CH2-CH2-Si（OR2）3]X，
wherein R is1Is a C12-C22 fatty alkyl radical, R2Is methyl or ethyl, and X is Cl ion, Br ion or I ion.
Preferably, R1 is an unsaturated fatty alkyl group of C12-C22, preferably a palmityl group; or R1 is a saturated fatty alkyl group of C12-C22, preferably lauryl.
The invention also provides a method for preparing the organosilicon quaternary ammonium salt, which comprises the following steps: and (3) carrying out synthetic reaction on fatty acid amide, halogenated propyl alkoxy silane and a reaction solvent to obtain the organosilicon quaternary ammonium salt.
Preferably, the molar ratio of fatty acid amide to halopropyl alkoxysilane is 1:0.8 to 1.2.
As a preferable scheme, the reaction temperature of the synthesis reaction is 50-150 ℃, preferably 60-120 ℃; the reaction time of the synthesis reaction is 20 to 200 hours, preferably 30 to 120 hours.
Preferably, the reaction solvent is any one of methanol, ethanol, propanol, isopropanol, and ethylene glycol, or a mixture thereof.
Preferably, the fatty acid amide is formed by condensation reaction of C12-C22 fatty acid and dimethyl propylene diamine.
Preferably, the molar ratio of the fatty acid of C12-C22 to the dimethyl propylene diamine is 1:0.8-1.2, and the reaction temperature of the condensation reaction is 120-240 ℃.
Preferably, the fatty acid of C12-C22 is coconut oil acid or lauric acid, and the halogenated propyl alkoxy silane is halopropyl trimethoxy silane or halopropyl triethoxy silane.
The invention also discloses application of the organic silicon quaternary ammonium salt in textile finishing, antibiosis/sterilization in public places or water treatment.
The technical scheme of the invention has the following advantages:
1. compared with the organic silicon quaternary ammonium salt in the market, the organic silicon quaternary ammonium salt provided by the invention has better degradability, is more environment-friendly due to the introduction of amido bond, has better water solubility, and has equivalent or better antibacterial/bactericidal capability.
2. According to the invention, fatty acid amide (namely fatty acid PKO) is generated by adopting the condensation reaction of C12-C22 fatty acid and dimethyl propane diamine, and then the fatty acid PKO and halogenated propyl alkoxy silane are used for synthesizing the organic silicon quaternary ammonium salt, so that the raw materials are easy to obtain, the reaction is mild, three wastes are not discharged, and a dangerous chemical process is not required.
3. The diluted solution of the organosilicon quaternary ammonium salt is used for antibacterial finishing of fabrics and antibacterial/sterilization of public places such as hospitals, kindergartens, schools, markets and the like; it may also be used in other sterilization settings including, but not limited to, water treatment, etc. And because of the introduction of amide chemical bonds, the product is bonded with a protected object such as fabric and the like more firmly. In addition, the molecular structure introduces amido bond with the same atomic group structure as peptide bond in protein and the structure has better water solubility, thereby having better effect of killing virus.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The embodiment of the invention provides an organosilicon quaternary ammonium salt, which has the following structural formula:
[R1-CO-NH-CH2-CH2-CH2-N（CH3）2-CH2-CH2-CH2-Si（OR2）3]X，
wherein R is1Is a C12-C22 fatty alkyl radical, R2Is methyl or ethyl, and X is Cl ion, Br ion or I ion. Wherein, R1 can be unsaturated fatty alkyl of C12-C22, such as palmityl, myristyl; or R1 is a saturated fatty alkyl group of C12-C22, such as lauryl.
Compared with the organic silicon quaternary ammonium salt on the market, the organic silicon quaternary ammonium salt has better degradability, is more environment-friendly due to the introduction of amido bond, has better water solubility, and has equivalent or better antibacterial/bactericidal capability.
The embodiment of the invention also provides a method for preparing the organosilicon quaternary ammonium salt, which comprises the following steps: and (3) carrying out synthetic reaction on fatty acid amide, halogenated propyl alkoxy silane and a reaction solvent to obtain the organosilicon quaternary ammonium salt. In actual use, the dilution ratio of the organosilicon quaternary ammonium salt is large, and therefore the reaction solvent is not removed. Of course, in other embodiments, the reaction solvent may also be removed after the synthesis reaction.
Preferably, the molar ratio of the fatty acid amide to the halogenated propyl alkoxysilane is 1 (0.8-1.2); the reaction temperature of the synthesis reaction is 50-150 ℃, preferably 60-120 ℃; the reaction time of the synthesis reaction is 20 to 200 hours, preferably 30 to 120 hours. Wherein the reaction solvent is any one or a mixture of methanol, ethanol, propanol isopropanol and ethylene glycol.
In a preferred embodiment, the fatty acid amide is formed by the condensation reaction of C12-C22 fatty acid and dimethyl propylene diamine. The molar ratio of the fatty acid of C12-C22 to the dimethyl propane diamine is 1 (0.8-1.2), and the reaction temperature of the condensation reaction is 120-240 ℃. The fatty acid of C12-C22 is coconut oil acid or lauric acid, and the halogenated propyl alkoxy silane is halogen propyl trimethoxy silane or halogen propyl triethoxy silane.
According to the invention, fatty acid amide (namely fatty acid PKO) is generated by adopting the condensation reaction of C12-C22 fatty acid and dimethyl propane diamine, and then the fatty acid PKO and halogenated propyl alkoxy silane are used for synthesizing the organic silicon quaternary ammonium salt, so that the raw materials are easy to obtain, the reaction is mild, three wastes are not discharged, and a dangerous chemical process is not required.
The embodiment of the invention also discloses application of the organic silicon quaternary ammonium salt in textile finishing, antibiosis/sterilization in public places or water treatment. The diluted solution of the organosilicon quaternary ammonium salt is used for antibacterial finishing of fabrics and antibacterial/sterilization of public places such as hospitals, kindergartens, schools, markets and the like; it may also be used in other antimicrobial/germicidal locations including, but not limited to, water treatment, etc. And because of the introduction of amide chemical bonds, the product is bonded with a protected object such as fabric and the like more firmly. In addition, the amido bond with the same atomic group structure as the peptide bond in the protein and the better water solubility of the structure are introduced into the molecular structure, so the structure has better effect of killing the virus.
The quaternary ammonium silicone salts and the preparation method thereof provided by the present invention will be described with reference to specific examples. It should be noted that, in the examples, the specific experimental procedures or conditions are not specified, and the procedures or conditions of the conventional experimental procedures described in the literature in the field can be performed. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
Example 1
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing coconut oil acid and dimethyl propylene diamine in a molar ratio of 1:1, and performing condensation reaction at 150 ℃ to prepare coconut oil PKO;
mixing coconut oil PKO, chloropropyl trimethoxyl silane and anhydrous methanol, wherein the molar ratio of the coconut oil PKO to the chloropropyl trimethoxyl silane is 1:1, and reacting at 80 ℃ for 120 hours; removing methanol to obtain organosilicon quaternary ammonium salt (i.e. cocamidopropyl trimethoxy silicon propyl ammonium chloride).
And (3) testing antibacterial performance: the solution is diluted to 0.42% by water, and the diameter of the inhibition ring is measured by an inhibition ring method. Test results show that the organosilicon quaternary ammonium salt prepared in the embodiment has an antibacterial effect on staphylococcus aureus with an antibacterial ring diameter larger than 7 mm; the diameter of the bacteriostatic ring is larger than 7mm, which has bacteriostatic action against candida albicans.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 2
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing lauric acid and dimethyl propylene diamine in a molar ratio of 1:1, and carrying out condensation reaction at 150 ℃ to prepare lauryl PKO;
mixing lauryl PKO, chloropropyl trimethoxyl silane and anhydrous methanol, wherein the molar ratio of the lauryl PKO to the chloropropyl trimethoxyl silane is 1:1, and reacting at 100 ℃ for 80 hours; removing methanol to obtain organosilicon quaternary ammonium salt (namely laurylamide propyl trimethoxy silicon propyl ammonium chloride).
And (3) testing antibacterial performance: diluted with water to a concentration of 1.0%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and a finished fabric was obtained. The treated fabric can produce antibacterial effect.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 3
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing coconut oil acid and dimethyl propylene diamine in a molar ratio of 1:1, and performing condensation reaction at 150 ℃ to prepare coconut oil PKO;
mixing coconut oil PKO, bromopropyl trimethoxy silane and anhydrous methanol, wherein the molar ratio of the coconut oil PKO to the bromopropyl trimethoxy silane is 1:1, and reacting at 100 ℃ for 150 hours; methanol is removed to obtain organosilicon quaternary ammonium salt (namely cocamidopropyl trimethoxysilylpropyl ammonium bromide).
And (3) testing antibacterial performance: diluted with water to a concentration of 0.42%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and a finished fabric was obtained. The treated fabric can produce antibacterial effect.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 4
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing lauric acid and dimethyl propylene diamine in a molar ratio of 1:1, and carrying out condensation reaction at 150 ℃ to prepare lauryl PKO;
mixing laurel PKO, bromopropyltrimethoxysilane and anhydrous methanol, wherein the molar ratio of laurel oil PKO to bromopropyltrimethoxysilane is 1:1, and reacting at 100 ℃ for 150 hours; removing methanol to obtain organosilicon quaternary ammonium salt (namely laurylamide propyl trimethoxysilylpropyl ammonium bromide).
And (3) testing antibacterial performance: diluting with water to a concentration of 0.3%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and obtaining a finished fabric. The treated fabric has antibacterial effect.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 5
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing coconut oil acid and dimethyl propylene diamine in a molar ratio of 1:1, and performing condensation reaction at 220 ℃ to prepare coconut oil PKO;
mixing coconut oil PKO, iodopropyl trimethoxy silane and anhydrous methanol, wherein the molar ratio of the coconut oil PKO to the iodopropyl trimethoxy silane is 1:1, and reacting at 80 ℃ for 120 hours; methanol is removed to obtain organosilicon quaternary ammonium salt (namely cocamidopropyl trimethoxysilylpropyl ammonium iodide).
And (3) testing antibacterial performance: diluting with water to a concentration of 0.2%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and obtaining a finished fabric. The treated fabric has antibacterial effect.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 6
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing lauric acid and dimethyl propylene diamine in a molar ratio of 1:1, and carrying out condensation reaction at 220 ℃ to prepare lauryl PKO;
mixing lauryl PKO, iodopropyl trimethoxy silane and anhydrous methanol, wherein the molar ratio of the lauryl oil PKO to the iodopropyl trimethoxy silane is 1:1, and reacting at 100 ℃ for 150 hours; removing methanol to obtain organosilicon quaternary ammonium salt (namely laurylamide propyl trimethoxysilylpropyl ammonium iodide).
And (3) testing antibacterial performance: diluted with water to a concentration of 0.9%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and a finished fabric was obtained. The treated fabric has antibacterial effect.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 7
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing coconut oil acid and dimethyl propylene diamine in a molar ratio of 1:0.8, and performing condensation reaction at 220 ℃ to prepare coconut oil PKO;
mixing coconut oil PKO, chloropropyl trimethoxyl silane and anhydrous methanol, wherein the molar ratio of the coconut oil PKO to the chloropropyl trimethoxyl silane is 1:1, and reacting at 80 ℃ for 120 hours; removing methanol to obtain organosilicon quaternary ammonium salt (i.e. cocamidopropyl trimethoxy silicon propyl ammonium chloride).
And (3) testing antibacterial performance: diluting with water to a concentration of 0.5%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and obtaining a finished fabric. And then measuring the diameter of the bacteriostatic ring by using a bacteriostatic ring method. Test results show that the antibacterial finishing fabric of the organosilicon quaternary ammonium salt prepared in the embodiment has an antibacterial effect on staphylococcus aureus with an antibacterial ring diameter larger than 7 mm; the diameter of the bacteriostatic ring is larger than 7mm, which has bacteriostatic action against candida albicans.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 8
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing lauric acid and dimethyl propylene diamine in a molar ratio of 1:1, and carrying out condensation reaction at 50 ℃ to prepare lauryl PKO;
mixing lauryl PKO, chloropropyl trimethoxyl silane and anhydrous methanol, wherein the molar ratio of the lauryl PKO to the chloropropyl trimethoxyl silane is 1:1, and reacting at 100 ℃ for 120 hours; removing methanol to obtain organosilicon quaternary ammonium salt (namely laurylamide propyl trimethoxy silicon propyl ammonium chloride).
And (3) testing antibacterial performance: diluting with water to a concentration of 0.1%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and obtaining a finished fabric. And then measuring the diameter of the bacteriostatic ring by using a bacteriostatic ring method. Test results show that the antibacterial finishing fabric of the organosilicon quaternary ammonium salt prepared in the embodiment has an antibacterial effect on staphylococcus aureus with an antibacterial ring diameter larger than 7.2 mm; the diameter of the bacteriostatic ring is larger than 7mm, which has bacteriostatic action against candida albicans.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 9
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing coconut oil acid and dimethyl propylene diamine in a molar ratio of 1:1, and performing condensation reaction at 150 ℃ to prepare coconut oil PKO;
mixing coconut oil PKO, chloropropyl trimethoxyl silane and anhydrous methanol, wherein the molar ratio of the coconut oil PKO to the chloropropyl trimethoxyl silane is 1:1.1, and reacting at 150 ℃ for 120 hours; removing methanol to obtain organosilicon quaternary ammonium salt (i.e. cocamidopropyl trimethoxy silicon propyl ammonium chloride).
And (3) testing antibacterial performance: diluted with water to a concentration of 0.8%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and a finished fabric was obtained. And then measuring the diameter of the bacteriostatic ring by using a bacteriostatic ring method. Test results show that the antibacterial finishing fabric of the organosilicon quaternary ammonium salt prepared in the embodiment has an antibacterial effect on staphylococcus aureus with an antibacterial ring diameter larger than 7 mm; the diameter of the bacteriostatic ring is larger than 7mm, which has bacteriostatic action against candida albicans.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 10
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing lauric acid and dimethyl propylene diamine in a molar ratio of 1:1, and carrying out condensation reaction at 150 ℃ to prepare lauryl PKO;
mixing lauryl PKO, chloropropyl trimethoxyl silane and anhydrous methanol, wherein the molar ratio of the lauryl PKO to the chloropropyl trimethoxyl silane is 1:1.1, and reacting at 150 ℃ for 120 hours; removing methanol to obtain organosilicon quaternary ammonium salt (namely laurylamide propyl trimethoxy silicon propyl ammonium chloride).
And (3) testing antibacterial performance: diluting with water to a concentration of 0.45%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and obtaining a finished fabric. And then measuring the diameter of the bacteriostatic ring by using a bacteriostatic ring method. Test results show that the antibacterial finishing fabric of the organosilicon quaternary ammonium salt prepared in the embodiment has an antibacterial effect on staphylococcus aureus with an antibacterial ring diameter larger than 7 mm; the diameter of the bacteriostatic ring is larger than 7mm, which has bacteriostatic action against candida albicans.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 11
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing coconut oil acid and dimethyl propylene diamine in a molar ratio of 1:0.7, and performing condensation reaction at 150 ℃ to prepare coconut oil PKO;
mixing coconut oil PKO, chloropropyl trimethoxyl silane and anhydrous methanol, wherein the molar ratio of the coconut oil PKO to the chloropropyl trimethoxyl silane is 1:1.3, and reacting at 150 ℃ for 120 hours; removing methanol to obtain organosilicon quaternary ammonium salt (i.e. cocamidopropyl trimethoxy silicon propyl ammonium chloride).
And (3) testing antibacterial performance: diluting with water to a concentration of 0.3%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and obtaining a finished fabric. And then measuring the diameter of the bacteriostatic ring by using a bacteriostatic ring method. Test results show that the antibacterial finishing fabric of the organosilicon quaternary ammonium salt prepared in the embodiment has an antibacterial effect on staphylococcus aureus with an antibacterial ring diameter larger than 7 mm; the diameter of the bacteriostatic ring is more than 6.8mm, which has bacteriostatic action against candida albicans.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
Example 12
The quaternary ammonium salt of organosilicon provided in this example was prepared by the following steps:
mixing lauric acid and dimethyl propylene diamine in a molar ratio of 1:1.3, and carrying out condensation reaction at 150 ℃ to prepare lauryl PKO;
mixing lauryl PKO, chloropropyl trimethoxyl silane and anhydrous methanol, wherein the molar ratio of the lauryl PKO to the chloropropyl trimethoxyl silane is 1:0.7, and reacting at 150 ℃ for 120 hours; removing methanol to obtain organosilicon quaternary ammonium salt (namely laurylamide propyl trimethoxy silicon propyl ammonium chloride).
And (3) testing antibacterial performance: diluting with water to a concentration of 0.6%, antibacterial finishing of clothes → prebaking (80 ℃. times.2 min) → baking (160 ℃. times.3 min), and obtaining a finished fabric. And then measuring the diameter of the bacteriostatic ring by using a bacteriostatic ring method. Test results show that the antibacterial finishing fabric of the organosilicon quaternary ammonium salt prepared in the embodiment has an antibacterial effect on staphylococcus aureus with an antibacterial ring diameter larger than 6.8 mm; the diameter of the bacteriostatic ring is more than 6.8mm, which has bacteriostatic action against candida albicans.
And (3) testing water solubility: 100ml of water (25 ℃) is added into a beaker, 2g of organosilicon quaternary ammonium salt is weighed and added into the beaker, strong shaking is carried out for 30s every 5min, and the dissolution condition within 30min is observed. The silicone quaternary ammonium salt prepared in this example was found to be readily soluble.
As can be seen from the test results of the above examples 1-12 and the comparative examples, the quaternary ammonium salt of organosilicon prepared by the invention has good antibacterial property and dissolution property.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. An organosilicon quaternary ammonium salt, characterized in that it has the following structural formula:
[R1-CO-NH-CH2-CH2-CH2-N（CH3）2-CH2-CH2-CH2-Si（OR2）3]X，
wherein R is1Is a C12-C22 fatty alkyl radical, R2Is methyl or ethyl, and X is Cl ion, Br ion or I ion.
2. The quaternary ammonium silicone salt according to claim 1, wherein R1 is an unsaturated fatty alkyl group of C12-C22, preferably a palmityl group; or R1 is a saturated fatty alkyl group of C12-C22, preferably lauryl.
3. A method of preparing the quaternary ammonium silicone salt of claim 1 or 2, comprising: and (3) carrying out synthetic reaction on fatty acid amide, halogenated propyl alkoxy silane and a reaction solvent to obtain the organosilicon quaternary ammonium salt.
4. The process of claim 3 wherein the molar ratio of fatty acid amide to halopropyl alkoxysilane is 1 (0.8-1.2).
5. The method according to claim 3, wherein the reaction temperature of the synthesis reaction is 50-150 degrees Celsius, preferably 60-120 degrees Celsius; the reaction time of the synthesis reaction is 20 to 200 hours, preferably 30 to 120 hours.
6. The method according to claim 3, wherein the reaction solvent is any one of methanol, ethanol, propanol, isopropanol, ethylene glycol or a mixture thereof.
7. The method of claim 3, wherein the fatty acid amide is formed by the condensation of a C12-C22 fatty acid with dimethyl propylene diamine.
8. The method as claimed in claim 7, wherein the molar ratio of the C12-C22 fatty acid to the dimethylpropylenediamine is 1 (0.8-1.2), and the reaction temperature of the condensation reaction is 120-240 ℃.
9. The method of claim 7, wherein the C12-C22 fatty acid is coconut oil acid or lauric acid, and the halopropyl alkoxysilane is halopropyl trimethoxysilane or halopropyl triethoxysilane.
10. Use of a quaternary ammonium silicone salt according to claim 1 or 2 in textile finishing, public space antibacterial or water treatment.
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|---|---|---|---|---|
| WO1997042200A1 (en) * | 1996-05-07 | 1997-11-13 | Bioshield Technologies, Inc. | Water-stabilized organosilane compounds and methods for using the same |
| WO1999003865A1 (en) * | 1997-07-18 | 1999-01-28 | Bioshield Technologies, Inc. | Water-stabilized organosilane compounds and methods for using the same |
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| US5954869A (en) * | 1997-05-07 | 1999-09-21 | Bioshield Technologies, Inc. | Water-stabilized organosilane compounds and methods for using the same |
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| WO1997042200A1 (en) * | 1996-05-07 | 1997-11-13 | Bioshield Technologies, Inc. | Water-stabilized organosilane compounds and methods for using the same |
| US5954869A (en) * | 1997-05-07 | 1999-09-21 | Bioshield Technologies, Inc. | Water-stabilized organosilane compounds and methods for using the same |
| WO1999003866A1 (en) * | 1997-07-17 | 1999-01-28 | Bioshield Technologies, Inc. | Water-stabilized organosilane compounds and their use |
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