CN102071577B - Preparation method of organosilicon quaternary ammonium salt type antibiosis soft finishing agent - Google Patents
Preparation method of organosilicon quaternary ammonium salt type antibiosis soft finishing agent Download PDFInfo
- Publication number
- CN102071577B CN102071577B CN2010106098058A CN201010609805A CN102071577B CN 102071577 B CN102071577 B CN 102071577B CN 2010106098058 A CN2010106098058 A CN 2010106098058A CN 201010609805 A CN201010609805 A CN 201010609805A CN 102071577 B CN102071577 B CN 102071577B
- Authority
- CN
- China
- Prior art keywords
- preparation
- nonionic emulsifier
- amido silicon
- quaternary ammonium
- ammonium salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 34
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 27
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 24
- 239000003921 oil Substances 0.000 claims abstract description 59
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 34
- 239000012875 nonionic emulsifier Substances 0.000 claims abstract description 21
- -1 amino silicane Chemical compound 0.000 claims description 78
- 229910052710 silicon Inorganic materials 0.000 claims description 56
- 239000010703 silicon Substances 0.000 claims description 56
- 238000003756 stirring Methods 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229920002545 silicone oil Polymers 0.000 claims description 14
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 11
- 229940073608 benzyl chloride Drugs 0.000 claims description 11
- 239000007822 coupling agent Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000000413 hydrolysate Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 239000001307 helium Substances 0.000 claims description 4
- 229910052734 helium Inorganic materials 0.000 claims description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Substances [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 3
- ZOTKGMAKADCEDH-UHFFFAOYSA-N 5-triethoxysilylpentane-1,3-diamine Chemical compound CCO[Si](OCC)(OCC)CCC(N)CCN ZOTKGMAKADCEDH-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000004945 emulsification Methods 0.000 claims description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 2
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 claims description 2
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 2
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 6
- 229920000742 Cotton Polymers 0.000 abstract description 5
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 239000002131 composite material Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 239000000835 fiber Substances 0.000 abstract description 3
- 244000025254 Cannabis sativa Species 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- OBFQBDOLCADBTP-UHFFFAOYSA-N aminosilicon Chemical compound [Si]N OBFQBDOLCADBTP-UHFFFAOYSA-N 0.000 abstract 4
- 238000005956 quaternization reaction Methods 0.000 abstract 4
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 abstract 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 abstract 1
- 235000009120 camo Nutrition 0.000 abstract 1
- 235000005607 chanvre indien Nutrition 0.000 abstract 1
- 239000011487 hemp Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 18
- 239000003995 emulsifying agent Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 230000000844 anti-bacterial effect Effects 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000011261 inert gas Substances 0.000 description 10
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- 125000001453 quaternary ammonium group Chemical group 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000002421 anti-septic effect Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000002152 alkylating effect Effects 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 239000003899 bactericide agent Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000012805 post-processing Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 241000191940 Staphylococcus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000005524 benzylchlorides Chemical class 0.000 description 3
- 238000005485 electric heating Methods 0.000 description 3
- 125000005909 ethyl alcohol group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000003961 organosilicon compounds Chemical class 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 150000003512 tertiary amines Chemical group 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010009736 Protein Hydrolysates Proteins 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- ONJQDTZCDSESIW-UHFFFAOYSA-N polidocanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ONJQDTZCDSESIW-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FHLZUEPKLGQEQP-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCC[Si](C)(OC)OC FHLZUEPKLGQEQP-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229920013822 aminosilicone Polymers 0.000 description 1
- 238000012550 audit Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
Images
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention belongs to the field of the fine chemical industry, and relates to a preparation method of an antibiosis soft finishing agent, which comprises the steps of: firstly preparing double amino silicon oil with the number-average molecular weight of 8000-12000; then using a quaternization reagent to carry out quaternization reaction on the double amino silicon oil, so a quaternization double amino silicon oil is obtained; and using a composite nonionic emulsifier to emulsify the quaternization double amino silicon oil, so the organosilicon quaternary ammonium salt type antibiosis soft finishing agent is obtained. The organosilicon quaternary ammonium salt type antibiosis soft finishing agent can be conveniently used for the antibiosis soft finishing of cotton, hemp, silk and chemical fiber fabric, and has an extremely good antibiosis soft effect.
Description
Technical field
The invention belongs to field of fine chemical, relate to a kind of preparation method of antibiotic soft finishing agent, be specifically related to a kind of preparation method of sterilization softener finishing agent of organosilicon quaternary ammonium salt type.
Background technology
Antibacterial finishing agent commonly used has alkyl quaternaries, organosilicon quaternary ammonium salt class, biguanides, mineral-type.The alkyl quaternary ammonium salts type is because its chemism is low, and a little less than the adhesion that is employed object, it is serious to run off.And its toxicity is bigger, and the smell is awful, and therefore the application in some fields is restricted.Organosilicon quaternary ammonium salt class antibacterial finishing agent belongs to non-dissolution type antibacterial finishing agent; In the antibacterial finishing agent of numerous types because of good endurance, do not have the problem that resistance to the action of a drug bacterium and antibacterial fabric occurs and lost efficacy, to the safe and reliable attention that receives people day by day of human body; And the organosilicon quaternary ammonium salt type can combine with application through chemical bond because of its specific molecule structure, has persistence; And because of organosilyl physiology inertia, its toxicity is also very low.Its main synthetic method of organosilicon quaternary ammonium salt class antiseptic has two kinds: 1) haloalkyl silane is quaternized; 2) amido silicon oil (silane) is quaternized.
1967; U.S. Dowcorning company at first develops organosilicon quaternary ammonium salt DC-5700 and has applied for patent; Three methoxyl groups in its molecular structure hydrolyzable in use become methyl alcohol; The part of sloughing methoxyl group forms hydroxyl, forms chemical bond with textiles and combines, and can be adsorbed on textile surface preferably.Be popular behind this launch products, but its synthetic method is complicated, cost is higher, has therefore limited its use.
The patent No. is the preparation method that a kind of organosilicon quaternary ammonium salt bactericide has been reported in the invention of China of 200510045294.0, and this patent has replaced methyl alcohol with absolute ethyl alcohol and made solvent, makes raw material cheap and easy to get, has overcome the weakness of DC-5700.Can be used for the fabric bactericide, the indoor environment bactericide.
The patent No. is that a kind of preparation method who contains the organo-silicon compound of quaternary ammonium group has been reported in the invention of China of 200710013423.7; The organo-silicon compound that obtain having tertiary amine groups with the secondary amine reaction through
; And then carry out quaterisation with alkyl halide; The organo-silicon compound that contain quaternary ammonium group with
general structure; This compound can be used as the organosilicon cationic surfactant and uses, and can be used as antibiotic, bactericide.Above-mentioned several method all belongs to the quaternized of haloalkyl silane, and it is as solvent with inflammable and explosive organic compound that a common part is arranged.Exist not enough at aspects such as transportation, storage, use, environmental protection.
In addition, amino in the amido silicon oil (silane) and different quaternizing agents react, and can obtain the silicone oil of different quaternary ammonium groups, for example:
1) Zhou Jianhua etc. is with a, and (WS-62M) is catalyst with the triethylamine with N-β-aminoethyl-γ-An Bingjisanjiayangjiguiwan (SG-Si 900) to alpha, omega-dihydroxy polydimethyl siloxane, has prepared reactive amino silicone oil.In aqueous isopropanol, be catalyst subsequently, with 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride (CHPTA) reaction, synthesized polysiloxane quaternary ammonium antibiotic soft finishing agent (referring to Zhou Jianhua, in great waves with NaOH; Polysiloxane quaternary ammonium antibiotic soft finishing agent synthetic, organosilicon material, 2006.20. (5): 238~242).Fabric after the arrangement of this organosilicon quaternary ammonium salt has preferably to golden yellow staphylococcus that biocidal property reaches 93.4%, but is merely 36.28% for the Escherichia coli effect is relatively poor.Aspect washability, through 10 washings, the biocidal property of golden yellow staphylococcus is just reduced to 91.2% from 93.4%, its washable effect is not good enough yet, and the demand that can't satisfy practical application is (referring to Zhou Jianhua, in great waves; Synthetic and application performance research, Shaanxi Tech Univ's journal, the 2006.Vol24. (5): 36~40) of polysiloxane quaternary ammonium.
2) Li Junying etc. is a closure agent with HMDO (MM); The silicon alkoxide of tetramethylammonium hydroxide is a catalyst; Make N, N-diethyl-aminopropyl methyl dimethoxysilane through hydrolysis again and octamethylcy-clotetrasiloxane (D4) make tertiary amine groups silicone oil, be quaternizing agent again with the benzyl chloride; The polysiloxane quaternary ammonium that makes has reached 100% to colibacillary bacteriostasis rate, and mould is also had certain inhibitory action.But what this method adopted is mono amino silane, after the hydrogen atom on the tertiary amine groups is replaced by benzyl; This molecule has not had the group that combines with fiber, washing fastness is very difficult to be guaranteed (referring to: Li Junying, Li Tianduo; Zhang Qingsi etc., the synthetic and antibiotic property of polysiloxane quaternary ammonium, daily chemical industry; The 34th rolls up in June, 2004 the 3rd phase, 154~156).
3) Gao Zhenghong has studied the quaternized and anti-microbial property of organosilicon macromolecule aminoethyl aminopropyl silicone oil.Through a series of signs to product, it is active to find that amido silicon oil after quaternized has a good antibiont, and has certain chemism, can form firm film with matrix, effectively suppresses the breeding of Escherichia coli, hay bacillus and Staphylococcus aureus.But bacteriostasis rate is only about 70%, and effect is not very good (referring to Gao Zhenghong, Zhu Feng, Xie Hongde; Quaternized and the anti-microbial property research of amido silicon oil, University Of Suzhou's journal, the 27th rolls up in April, 2007 the 2nd phase, 40~43).
Comprehensively above-mentioned, prior preparation method, more or less exist such-and-such problems and shortcomings, it is level and smooth, antistatic, hydrophilic to fabric sofetening, fiber to satisfy people, has sterilizing and anti-foul, anti-shrinkage and laundry-resistant requirement again.
Summary of the invention
The object of the invention provides a kind of preparation method of organosilicon quaternary ammonium salt type antibiotic soft finishing agent.
For achieving the above object, the technical scheme that the present invention adopts is: a kind of preparation method of organosilicon quaternary ammonium salt type antibiotic soft finishing agent may further comprise the steps:
1) in inert gas atmosphere; Heater wire gonosome silicone oil to 95~105 ℃ while stirring; Add the hydrolysate and the base catalyst of two amino silicane coupling agents then, under the protection of inert gas, stir and be warmed up to 120~140 ℃, react 0.8~1.2h with this understanding after; Reaction system is vacuumized, make reaction system vacuum reach 0.001~0.01MPa, continue reaction 3~4h; When reaction system viscosity becomes big; When reaching 4000mPa.s~7000mPa.s value, feed inert gas and make pressure return to atmospheric pressure, cessation reaction; Obtain water white thick liquid, this water white thick liquid is for being equipped with number-average molecular weight at two amido silicon oils of 8000~12000;
2) use quaternizing agent then, two amido silicon oils are carried out quaterisation, obtain quaternized pair of amido silicon oil;
3) use quaternized pair of amido silicon oil of compound nonionic emulsifier emulsification again, get organosilicon quaternary ammonium salt antibiotic soft finishing agent.
In the technique scheme; The said linear body silicone oil of step 1) is with the hydroxy-end capped dimethyl silicone polymer of silicon; Viscosity (25 ℃) 500~1500cp; Hydroxy radical content>=10%, refractive index (25 ℃) 1.40~1.41, its structural formula is
; Preferably, the said linear body silicone oil model that is Dow corning company is 0156 linear body silicone oil.
In the technique scheme; Said pair of amino silicane coupling agent of step 1) is selected from: 3-(2-aminoethyl)-aminopropyl methyl dimethoxysilane, 3-(2-aminoethyl)-aminopropyl trimethoxysilane or 3-(2-aminoethyl)-aminopropyl triethoxysilane, the consumption of said pair of amino silicane coupling agent is 4%~5% of a linear body silicone oil quality.
In the technique scheme; The said base catalyst of step 1) is selected from: potassium hydroxide, NaOH, lithium hydroxide or tetramethyl oxyammonia, the consumption of said base catalyst are linear body silicone oil and 0.03~0.08% of the hydrolysate gross weight of two amino silicane coupling agents.
In the technique scheme, step 2) said quaternizing agent is selected from: benzyl chloride, cylite or 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride.
In the technique scheme; In the step 3); The mass ratio of compound nonionic emulsifier and quaternized amido silicon oil is (0.5~1): 2; The hydrophilic and oleophilic value HLB of said compound nonionic emulsifier is 9~12, is selected from: the mixture of AEO nonionic emulsifier or NPE nonionic emulsifier; Preferably, the mass ratio of AEO nonionic emulsifier, NPE nonionic emulsifier is 1: 1; Said AEO nonionic emulsifier comprises: AEO nonionic emulsifier TX-4, TX-5, TX-7, TX-9, TX-10; Said NPE nonionic emulsifier comprises: NPE nonionic emulsifier AEO-3, AEO-4, AEO-5, AEO-7, AEO-9.
In the technique scheme, said inert gas is nitrogen, argon gas, helium etc., nitrogen.
In the technique scheme, in the process of said " use quaternizing agent, two amido silicon oils are carried out quaterisation ", the hydrogen atom on the amino in the amido silicon oil is got quaternized amido silicon oil by benzyl moiety or all replacements.
Particularly, a kind of preparation method of organosilicon quaternary ammonium salt type antibiotic soft finishing agent may further comprise the steps:
1) at first use air in the inert gas replacement reactor, heater wire gonosome silicone oil to 95 in the time of stirring~105 ℃ adds the hydrolysate and the base catalyst of two amino silicane coupling agents then; Under the protection of inert gas, stir and be warmed up to 120~140 ℃, react 1h with this understanding after, close inert gas; Reaction system is vacuumized, make reaction system vacuum reach 0.001~0.01MPa, continue reaction 3~4h; When reaction system viscosity becomes big, when reaching 4000mPa.s~7000mPa.s value, close vacuum; Open inert gas and make pressure return to atmospheric pressure, cessation reaction obtains water white thick liquid; This water white thick liquid is a number-average molecular weight at two amido silicon oils of 8000~12000;
2) mix two amido silicon oils and solvent, add quaternizing agent again, under the stirring condition, condensing reflux under 90~110 ℃ of conditions reacted 5~6 hours; Reaction finishes last hour, and reaction system is vacuumized, and makes reaction system vacuum reach 0.08~0.1MPa; So that remove small solvent molecule and impurity, obtain flaxen thick liquid, get quaternised pair of amido silicon oil;
3) mix compound nonionic emulsifier and quaternised pair of amido silicon oil; Stir; Add deionized water and do the phase inversion reaction, make system change water into, continue to add the water stirring and adjusting to required solid content 12~50% from oil phase; Add vinegar acid for adjusting pH value to 5~6, products therefrom is organosilicon quaternary ammonium salt type antibiotic soft finishing agent.
In the technique scheme, the hydrolysate of said pair of amino silicane coupling agent of step 1) is meant: in two amino silicane coupling agents, add the deionized water of its weight 16~18%, 2 hours products therefroms of hydrolysis under 50 ℃ of conditions.
In the technique scheme, in the step 1), reduce activity of such catalysts or heat up end such as the way of destroying catalyst reaction through cooling; Two amido silicon oil amido silicon oil number-average molecular weights that step 1) obtains are 8000~12000; Owing to the existence of base catalyst is arranged, so standing time can not be oversize, need speed to do quaternized processing.
In the technique scheme, step 2) in, said solvent is absolute ethyl alcohol or isopropyl alcohol; Two amido silicon oils: quaternizing agent: the mass ratio of solvent is 1: 1.5~2: 2.5~3; Wherein, small molecular weight impurity mainly comprises benzyl chloride; This reaction owing to there is sour gas to produce in step, but part neutralization procedure 1) in base catalyst.
Because the technique scheme utilization, the present invention compared with prior art has advantage:
The antibiotic soft that 1) can be used for cotton, silk fabric and chemical & blended fabric is very easily put in order, directly adds during use in the entry, and consumption serves as an amount of with 5% heavy (5%OWF) of fabric, soaks, all can roll;
2) very high anti-, bactericidal effect.Test oneself through the cotton (32 cotton towels) of antibacterial softener of the present invention arrangement, Real Silk Habotai (through filling density be 616 * 400/10cm) and PET Nylon Taffeta fabric (through filling density be 900 * 500/10cm) anti-, the sterilizing rate to Escherichia coli, golden yellow staphylococcus, withered grass bacterium all reaches more than 98%.Sample presentation detects to Jiangsu Prov. Disease Preventing and Controlling Center through 32 cotton towels of antibacterial softener arrangement, gets audit report and is numbered (disappearing) 20090205, and getting the Escherichia coli bacteriostasis rate is 99.33%;
3) owing to adopted molecular weight control technology of the present invention; Prepared number-average molecular weight at 8000~12000 two amido silicon oils; Make the back quaterisation to carry out accurately, by quaternized, another amino keeps its result for an amino in two amido silicon oils; Therefore through the existing fabulous antibacterial effect of fabric of antibacterial softener arrangement of the present invention, fabulous soft effect is arranged again.
Description of drawings
The schematic flow sheet of preparation organosilicon quaternary ammonium salt type antibiotic soft finishing agent among Fig. 1 embodiment.
The specific embodiment
Below in conjunction with accompanying drawing and embodiment the present invention is further described:
Embodiment one: the schematic flow sheet of preparation organosilicon quaternary ammonium salt type antibiotic soft finishing agent is referring to accompanying drawing 1.
1, the preparation of two amido silicon oils: take by weighing 3-(2-the aminoethyl)-aminopropyl methyl dimethoxysilane (being called for short 602) of 45g and the distilled water (10:1) of 4.5g; Mix in the reactor of adding 100ml; Hydrolysis 2h is stirred in electric heating constant temperature water-bath heating under 50 ℃ temperature, obtain 602 hydrolysate;
At first use the air in the nitrogen replacement reactor, 1000 g linear bodies are joined in the reactor of 2000ml and be heated with stirring to 100 ℃, add 602 hydrolysate and catalyst KOH 0.5g then; Under nitrogen protection, constantly stir and be warmed up to 130 ℃, close nitrogen after reacting 1h with this understanding, open water-ring vacuum pump; Make and be with negative pressure in the reactor, vacuum is 0.001~0.01MPa, continues reaction 3~4h; When reaction system viscosity becomes big, when reaching 4000mPa.s~7000mPa.s value, close vacuum; Open the nitrogen valve and make the pressure in the reactor return to normal pressure, continue to cool to room temperature, obtain water white thick liquid.Two amido silicon oil number-average molecular weights that the method obtains are 8000~12000.Owing to the existence of catalyst KOH is arranged, so standing time can not be oversize, need speed to do quaternized processing.
2, the quaternized processing of two amido silicon oils: in the reactor of 1000ml of a band condensation reflux unit, band vacuum extractor, add two amido silicon oils that 100 g prepare; Add 300 g absolute ethyl alcohols as solvent; In reactor, mix, add 150 g benzyl chlorides again, proportioning raw materials (two amido silicon oils: benzyl chloride) press the 1:1.5 preparation as alkylating reagent; Under 300 rotating speeds, open condensation reflux unit and under 105 ℃ of conditions, reacted 6 hours.Reaction finishes last hour, closes condensing reflux condensate liquid is reclaimed.Keep reaction temperature constant, open vacuum extractor, make vacuum as far as possible near 0.1MPa while stir to vacuumize, the purpose of product being carried out post processing is to remove micromolecule such as solvent and benzyl chloride as far as possible, obtains flaxen thick liquid.
3, the configuration of antiseptic emulsion: in the reactor of 2000ml, it is composite that the emulsifying agent TX-10 of 150g emulsifying agent AEO-9 and 150g is pressed 1:1, the 300g blended emulsifier; Slowly add quaternised couple of amido silicon oil 600g after the mixing and stirring, (quaternised pair of amido silicon oil: emulsifying agent) stir, get 50g distilled water and continue to stir by the 2:1 preparation; Stir usefulness after one hour, add acetic acid, regulate pH value to 5~6; Add entry again and stir, regulate concentration to active ingredient 20%.Leave standstill emulsion at last and wait until the product that obtains the oolemma blue light behind the lather collapse.This product is exactly an organosilicon antibacterial agent, directly adds in the entry when needing to use, and 5% (5%OWF) heavy with fabric serves as an amount of.
Embodiment two: the schematic flow sheet of preparation organosilicon quaternary ammonium salt type antibiotic soft finishing agent is referring to accompanying drawing 1.
1, the preparation of two amido silicon oils:
Take by weighing 3-(2-the aminoethyl)-aminopropyl trimethoxysilane (being called for short 603) of 45g and the distilled water (10:1) of 4.5g; Mix in the reactor of adding 100ml; Hydrolysis 2h is stirred in electric heating constant temperature water-bath heating under 50 ℃ temperature, obtain 602 hydrolysate;
At first use the air in the inert gas replacement reactor, 1000 g linear bodies are joined in the reactor of 2000ml and be heated with stirring to 100 ℃, add 603 hydrolysate, catalyst KOH 0.5g then, under nitrogen protection, constantly stir and be warmed up to 130 ℃; After reacting 1h with this understanding, close nitrogen, open water-ring vacuum pump; Make and be with negative pressure in the reactor, vacuum is 0.001~0.01MPa, continues reaction 3~4h; When reaction system viscosity becomes big, when reaching 4000mPa.s~7000mPa.s value, close vacuum; Open the nitrogen valve and make pressure return to normal pressure, be cooled to normal temperature, obtain water white thick liquid.Two amido silicon oil number-average molecular weights that the method obtains are 8000~12000.Owing to the existence of catalyst KOH is arranged, so standing time can not be oversize, need speed to do quaternized processing.
2, the quaternized processing of two amido silicon oils: in the reactor of 1000ml of a band condensation reflux unit, band vacuum extractor, add two amido silicon oils that 100 g prepare; Add 300 g absolute ethyl alcohols as solvent; In reactor, mix, add 150 g benzyl chlorides again, proportioning raw materials (two amido silicon oils: benzyl chloride) press the 1:1.5 preparation as alkylating reagent; Under 300 rotating speeds, open condensation reflux unit and under 105 ℃ of conditions, reacted 6 hours.Reaction finishes last hour, closes condensing reflux condensate liquid is reclaimed.Keep reaction temperature constant, open vacuum extractor, make vacuum as far as possible near 0.1MPa while stir to vacuumize, the purpose of product being carried out post processing is to remove micromolecule such as solvent and benzyl chloride as far as possible, obtains flaxen thick liquid.
3, the configuration of antiseptic emulsion: in the reactor of 2000ml, it is composite that the emulsifying agent TX-10 of 150g emulsifying agent AEO-7 and 150g is pressed 1:1, the 300g blended emulsifier; Slowly add quaternised couple of amido silicon oil 600g after the mixing and stirring, (quaternised pair of amido silicon oil: emulsifying agent) stir, get 50g distilled water and continue to stir by the 2:1 preparation; Stir usefulness after one hour, add acetic acid, regulate pH value to 5~6; Add entry again and stir, regulate concentration to active ingredient 20%.Leave standstill emulsion at last and wait until the product that obtains the oolemma blue light behind the lather collapse.This product is exactly an organosilicon antibacterial agent, directly adds in the entry when needing to use, and 5% (5%OWF) heavy with fabric serves as an amount of.
Embodiment three: the schematic flow sheet of preparation organosilicon quaternary ammonium salt type antibiotic soft finishing agent is referring to accompanying drawing 1.
1, the preparation of two amido silicon oils: take by weighing 3-(2-the aminoethyl)-aminopropyl triethoxysilane (being called for short 613) of 45g and the distilled water (10:1) of 5.5g; Mix in the reactor of adding 100ml; Hydrolysis 4h is stirred in electric heating constant temperature water-bath heating under 50 ℃ temperature, obtain 613 hydrolysate;
At first use the air in the inert gas replacement reactor, 1000 g linear bodies are joined in the reactor of 2000ml and be heated with stirring to 100 ℃, add 613 hydrolysate, catalyst KOH 0.5g then; Under nitrogen protection, constantly stir and be warmed up to 130 ℃, close nitrogen after reacting 1h with this understanding, open water-ring vacuum pump; Make and be with negative pressure in the reactor, vacuum is 0.001~0.01MPa, continues reaction 3~4h; When reaction system viscosity becomes big, when reaching 4000mPa.s~7000mPa.s value, close vacuum; Open the nitrogen valve and make pressure return to normal pressure, cool to normal temperature, obtain water white thick liquid.Two amido silicon oil number-average molecular weights that the method obtains are 8000~12000.Owing to the existence of catalyst KOH is arranged, so standing time can not be oversize, need speed to do quaternized processing.
2, the quaternized processing of two amido silicon oils: in the reactor of 1000ml of a band condensation reflux unit, band vacuum extractor, add two amido silicon oils that 100 g prepare; Add 400 g isopropyl alcohols as solvent; In reactor, mix, add 150 g benzyl chlorides again, proportioning raw materials (two amido silicon oils: benzyl chloride) press the 1:1.5 preparation as alkylating reagent; Under 300 rotating speeds, open condensation reflux unit and under 110 ℃ of conditions, reacted 6 hours.Reaction finishes last hour, closes condensing reflux condensate liquid is reclaimed.Keep reaction temperature constant, open vacuum extractor, make vacuum as far as possible near 0.1MPa while stir to vacuumize, the purpose of product being carried out post processing is to remove micromolecule such as solvent and benzyl chloride as far as possible, obtains flaxen thick liquid.
3, the configuration of antiseptic emulsion: in the reactor of 2000ml, it is composite that the emulsifying agent TX-10 of 150g emulsifying agent AEO-7 and 150g is pressed 1:1, the 300g blended emulsifier; Slowly add quaternised couple of amido silicon oil 600g after the mixing and stirring, (quaternised pair of amido silicon oil: emulsifying agent) stir, get 50g distilled water and continue to stir by the 2:1 preparation; Stir usefulness after one hour, add acetic acid, regulate pH value to 5~6; Add entry again and stir, regulate concentration to active ingredient 20%.Leave standstill emulsion at last and wait until the product that obtains the oolemma blue light behind the lather collapse.This product is exactly an organosilicon antibacterial agent, directly adds in the entry when needing to use, and 5% (5%OWF) heavy with fabric serves as an amount of.
Embodiment four: the schematic flow sheet of preparation organosilicon quaternary ammonium salt type antibiotic soft finishing agent is referring to accompanying drawing 1.
1, the preparation of two amido silicon oils: with embodiment one
2, the quaternized processing of two amido silicon oils: in the reactor of 1000ml of a band condensation reflux unit, band vacuum extractor, add two amido silicon oils that 100 g prepare; Add 300 g absolute ethyl alcohols as solvent; In reactor, mix, add 250 g again; 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride is as alkylating reagent, and (two amido silicon oils: 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride) press the 1:2.5 preparation, under 300 rotating speeds, the unlatching condensation reflux unit reacted 6 hours under 95 ℃ of conditions proportioning raw materials.Reaction finishes last hour, closes condensing reflux condensate liquid is reclaimed.Keep reaction temperature constant, open vacuum extractor, make vacuum as far as possible near 0.1MPa while stir to vacuumize, the purpose of product being carried out post processing is to remove micromolecule such as solvent and benzyl chloride as far as possible, obtains flaxen thick liquid.
3, the configuration of antiseptic emulsion: in the reactor of 2000ml, it is composite that the emulsifying agent TX-5 of 150g emulsifying agent AEO-5 and 150g is pressed 1:1, the 300g blended emulsifier; Slowly add quaternised couple of amido silicon oil 600g after the mixing and stirring, (quaternised pair of amido silicon oil: emulsifying agent) stir, get 50g distilled water and continue to stir by the 2:1 preparation; Stir usefulness after one hour, add acetic acid, regulate pH value to 5~6; Add entry again and stir, regulate concentration to active ingredient 20%.Leave standstill emulsion at last and wait until the product that obtains the oolemma blue light behind the lather collapse.This product is exactly an organosilicon antibacterial agent, directly adds in the entry when needing to use, and 5% (5%OWF) heavy with fabric serves as an amount of.
Claims (6)
1. the preparation method of an organosilicon quaternary ammonium salt type antibiotic soft finishing agent is characterized in that, may further comprise the steps:
1) in nitrogen, argon gas or helium atmosphere; Heater wire gonosome silicone oil to 95~105 ℃ while stirring; The hydrolysate and the base catalyst that add two amino silicane coupling agents then; Under the protection of nitrogen, argon gas or helium, stir and be warmed up to 120~140 ℃, react 0.8~1.2h with this understanding after; Reaction system is vacuumized, make reaction system vacuum reach 0.001~0.01MPa, continue reaction 3~4h; When reaction system viscosity becomes big; When reaching 4000mPa.s~7000mPa.s value, feed nitrogen, argon gas or helium and make pressure return to atmospheric pressure, cessation reaction; Obtain water white thick liquid, this water white thick liquid is a number-average molecular weight at two amido silicon oils of 8000~12000;
2) use quaternizing agent then, two amido silicon oils are carried out quaterisation, obtain quaternized pair of amido silicon oil;
3) use quaternized pair of amido silicon oil of compound nonionic emulsifier emulsification again, get organosilicon quaternary ammonium salt antibiotic soft finishing agent.
2. according to the said preparation method of claim 1, it is characterized in that the silicone oil of linear body described in the step 1) is with the hydroxy-end capped dimethyl silicone polymer of silicon, viscosity is 500~1500cp during hydroxy radical content >=10%, 25 ℃, and refractive index is 1.40~1.41 in the time of 25 ℃.
3. according to the said preparation method of claim 1; It is characterized in that; In the step 1); Said pair of amino silicane coupling agent is selected from: 3-(2-aminoethyl)-aminopropyl methyl dimethoxysilane, 3-(2-aminoethyl)-aminopropyl trimethoxysilane or 3-(2-aminoethyl)-aminopropyl triethoxysilane, the consumption of said pair of amino silicane coupling agent is 4%~5% of a linear body silicone oil quality.
4. according to the said preparation method of claim 1; It is characterized in that; In the step 1); Said base catalyst is selected from: potassium hydroxide, NaOH, lithium hydroxide or TMAH, the consumption of said base catalyst are linear body silicone oil and 0.03~0.08% of the hydrolysate gross weight of two amino silicane coupling agents.
5. according to the said preparation method of claim 1, it is characterized in that step 2) in, said quaternizing agent is selected from: benzyl chloride, cylite or 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride.
6. according to the said preparation method of claim 1; It is characterized in that; In the step 3); The mass ratio of said compound nonionic emulsifier and quaternized pair of amido silicon oil is 0.5~1: 2; The hydrophilic and oleophilic value HLB of compound nonionic emulsifier is 9~12, and compound nonionic emulsifier is the mixture of AEO nonionic emulsifier and NPE nonionic emulsifier, and the mass ratio of AEO nonionic emulsifier, NPE nonionic emulsifier is 1: 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010106098058A CN102071577B (en) | 2010-12-28 | 2010-12-28 | Preparation method of organosilicon quaternary ammonium salt type antibiosis soft finishing agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010106098058A CN102071577B (en) | 2010-12-28 | 2010-12-28 | Preparation method of organosilicon quaternary ammonium salt type antibiosis soft finishing agent |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102071577A CN102071577A (en) | 2011-05-25 |
CN102071577B true CN102071577B (en) | 2012-07-04 |
Family
ID=44030319
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2010106098058A Active CN102071577B (en) | 2010-12-28 | 2010-12-28 | Preparation method of organosilicon quaternary ammonium salt type antibiosis soft finishing agent |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102071577B (en) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102505494B (en) * | 2011-11-09 | 2013-06-12 | 苏州大学 | Silver-loaded antibacterial amino silicone oil fabric finishing agent and preparation method thereof |
CN103194889B (en) * | 2013-04-19 | 2015-11-25 | 武汉纺织大学 | A kind of cation modifying method of cellulose fibre |
CN103397529B (en) * | 2013-08-01 | 2015-12-23 | 广州大学 | A kind of organosilicon macromolecule softener |
CN103804690B (en) * | 2014-03-17 | 2017-05-17 | 广州市仲沅其新型材料有限公司 | Method for preparing double amino-terminated linear polydimethylsiloxane |
TWI607067B (en) * | 2015-09-25 | 2017-12-01 | 立得光電科技股份有限公司 | Anti-bacterial and anti-mould surface coating, and manufacturing method thereof |
CN105199577B (en) * | 2015-09-30 | 2017-05-17 | 浙江大学 | Antibacterial low-surface-energy marine antifouling paint composition |
CN105885054B (en) * | 2016-04-28 | 2018-09-14 | 华南理工大学 | A kind of polysiloxane block copolymers and preparation method and application containing quaternary ammonium salt group |
CN105901013B (en) * | 2016-04-28 | 2018-12-07 | 华南农业大学 | Block macromolecular quaternary ammonium salt is inhibiting the purposes in banana blight bacteria growth |
CN105985870A (en) * | 2016-07-13 | 2016-10-05 | 西南大学 | Quick-drying antimicrobial mildewproof multifunctional laundry detergent and preparation method thereof |
CN106245323A (en) * | 2016-08-16 | 2016-12-21 | 常熟市大正纺织制版有限公司 | The postfinishing process of the knitting fabric of underwear |
CN108625166B (en) * | 2017-03-23 | 2022-03-11 | 北京卡尼尔科技有限公司 | Method for finishing antibacterial organosilicon quaternary ammonium salt for cotton yarn |
CN108727593A (en) * | 2018-06-15 | 2018-11-02 | 张礼国 | A kind of antimicrobial organosilane glue material and preparation method thereof |
CN111333847A (en) * | 2020-04-28 | 2020-06-26 | 四川景文材料科技有限公司 | End-capped multipurpose antibacterial organic silicon resin and preparation method thereof |
CN111334052A (en) * | 2020-04-28 | 2020-06-26 | 四川景文材料科技有限公司 | Multifunctional antibacterial weather-resistant composite material composition and preparation method thereof |
CN114409904A (en) * | 2022-01-19 | 2022-04-29 | 杭州一川新材料有限公司 | Preparation method and application of condensed type transparent silicone rubber |
CN115612107A (en) * | 2022-09-27 | 2023-01-17 | 唐山三友硅业有限责任公司 | Three-dimensional bactericidal algicidal organopolysiloxane, emulsion and preparation method thereof |
CN116575165B (en) * | 2023-05-17 | 2024-02-13 | 江苏鸿鹏服饰有限公司 | Skin-friendly antibacterial sleeping bag fabric and preparation method thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040048996A1 (en) * | 2000-07-27 | 2004-03-11 | Horst Lange | Polymmonium-polysiloxane compounds, methods for the production and use thereof |
CN101418517A (en) * | 2008-11-10 | 2009-04-29 | 江南大学 | Method for preparing quaternary ammonium salt sol for antibacterial textile |
CN101565896A (en) * | 2008-12-22 | 2009-10-28 | 上海氟聚化学产品有限公司 | Quaternary amino cation modified polysiloxane softening agent and preparation method thereof |
-
2010
- 2010-12-28 CN CN2010106098058A patent/CN102071577B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040048996A1 (en) * | 2000-07-27 | 2004-03-11 | Horst Lange | Polymmonium-polysiloxane compounds, methods for the production and use thereof |
CN101418517A (en) * | 2008-11-10 | 2009-04-29 | 江南大学 | Method for preparing quaternary ammonium salt sol for antibacterial textile |
CN101565896A (en) * | 2008-12-22 | 2009-10-28 | 上海氟聚化学产品有限公司 | Quaternary amino cation modified polysiloxane softening agent and preparation method thereof |
Non-Patent Citations (1)
Title |
---|
高正宏等.氨基硅油的季铵化及其抗菌性能研究.《苏州大学学报》.2007,第27卷(第2期), * |
Also Published As
Publication number | Publication date |
---|---|
CN102071577A (en) | 2011-05-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102071577B (en) | Preparation method of organosilicon quaternary ammonium salt type antibiosis soft finishing agent | |
US10391179B2 (en) | Organomodified carbosiloxane monomers containing compositions and uses thereof | |
EP2688938B1 (en) | Organomodified carbosiloxane monomers containing compositions and uses thereof | |
US8530601B2 (en) | Copolymers of epoxy compounds and amino silanes | |
US8569385B2 (en) | Hydrolysis resistant organomodified silylated ionic surfactants | |
CN104817847B (en) | A kind of antimicrobial organosilane elastomer emulsions and the preparation method and application thereof | |
CN100516077C (en) | Preparing method for organic silicon compound containing quaternary ammonium group | |
CN103820995B (en) | The preparation method of the waterproofing agent of organosilicon of reinforced waterproof mildew-resistant | |
AU2008343778A1 (en) | Mixtures of hydrolysis resistant organomodified trisiloxane ionic surfactants | |
US20110021644A1 (en) | Hydrolysis resistant organomodified trisiloxane ionic surfactants | |
US20140235885A1 (en) | Copolymers of epoxy compounds and amino silanes | |
US20090171108A1 (en) | Mixtures comprising hydrolysis resistant organomodified disiloxane ionic surfactants | |
JP2003533558A (en) | Agricultural composition using organosiloxane containing multiple hydroxyl groups | |
US8367740B2 (en) | Hydrolysis resistant organomodified disiloxane ionic surfactants | |
US20150191560A1 (en) | Thickened compositions comprising crosslinked polymers containing biomass derived materials | |
US20080167269A1 (en) | Hydrolysis resistant organomodified silylated ionic surfactants | |
KR101595329B1 (en) | Textiles treated with copolymers of epoxy compounds and amino silanes | |
Luo et al. | Synthesis and properties of a hydrolysis resistant cationic trisiloxane surfactant | |
US20080033136A1 (en) | Selective hydrosilylation conditions | |
CN113549220A (en) | Modified hydrogen-containing silicone oil and preparation method and application thereof | |
Zhao et al. | A comblike polysiloxane with pendant quaternary ammonium polyether groups: its synthesis, physical properties and antibacterial performance | |
US6384173B1 (en) | Silicone functionalized triclosan | |
US20120220791A1 (en) | Copolymers of epoxy compounds and amino silanes | |
CN117866208A (en) | Synthesis method of cationic block silicone oil | |
CN116391725A (en) | Hydrophobic bactericide and preparation method thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: 215127 No. 248 Changhong North Road, Yonzhi Town, Wuzhong District, Suzhou City, Jiangsu Province Patentee after: SUZHOU UONE PLASTIC INDUSTRY Co.,Ltd. Country or region after: China Address before: Suzhou City, Jiangsu province 215021 Suzhou Industrial Park Yang Ching No. 39 Patentee before: Suzhou Industrial Park UONE Plastic Industry Co.,Ltd. Country or region before: China |