CN1059914C - Method for preparation of ammonium methyl N.N.N-trimethyl-N abietylsulfate - Google Patents
Method for preparation of ammonium methyl N.N.N-trimethyl-N abietylsulfate Download PDFInfo
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- CN1059914C CN1059914C CN97111998A CN97111998A CN1059914C CN 1059914 C CN1059914 C CN 1059914C CN 97111998 A CN97111998 A CN 97111998A CN 97111998 A CN97111998 A CN 97111998A CN 1059914 C CN1059914 C CN 1059914C
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- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 title abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 24
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 21
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- IPTLKMXBROVJJF-UHFFFAOYSA-N azanium;methyl sulfate Chemical compound N.COS(O)(=O)=O IPTLKMXBROVJJF-UHFFFAOYSA-N 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 13
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 12
- 235000019253 formic acid Nutrition 0.000 claims description 12
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000012264 purified product Substances 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 230000001035 methylating effect Effects 0.000 claims description 2
- 238000007039 two-step reaction Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- ZGFPIGGZMWGPPW-UHFFFAOYSA-N formaldehyde;formic acid Chemical compound O=C.OC=O ZGFPIGGZMWGPPW-UHFFFAOYSA-N 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- WREBNDYJJMUWAO-LWYYNNOASA-N [(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)[C@@H](CCC(C(C)C)=C3)C3=CC[C@H]21 WREBNDYJJMUWAO-LWYYNNOASA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012022 methylating agents Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- -1 alkyl quaternary ammonium salt Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- NQNOMXXYKHWVKR-UHFFFAOYSA-N methylazanium;sulfate Chemical compound NC.NC.OS(O)(=O)=O NQNOMXXYKHWVKR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000006485 reductive methylation reaction Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides a method for preparing ammonium monomethyl N, N, N-trimethyl-N-abietyl sulfate by using abietylamine as a raw material, which comprises the following steps: formaldehyde-formic acid is used as a methylating agent to prepare N, N-dimethyl abietylamine (A), and then the N, N-dimethyl abietylamine (A) and dimethyl sulfate carry out quaterisation in solvent. An obtained product has good bactericidal powder.
Description
The present invention relates to a kind of N, N, the preparation method of N-trimethylammonium-N-rosinyl methyl sulfate ammonium belongs to technical field of surfactant.
N, N, N-trimethylammonium-N-rosinyl methyl sulfate ammonium be a kind of with rosinyl as oleophilic group and the direct-connected quaternary cationic surfactant of nitrogen-atoms.Alkyl is well-known commercial already cats product as oleophilic group and the direct-connected straight chained alkyl quaternary ammonium salt of nitrogen-atoms, just assert that as far back as nineteen thirty-five this cationoid tensio-active agent has biocidal property.Yet, because the biological degradability of existing monoalkyl, dialkyl quaternary ammonium salt class tensio-active agent is poor, and existing various sterilant is after using the certain period, bacterium can develop immunity to drugs, need exploitation constantly to have the sterilant of new texture, therefore, the present invention utilizes the rosinyl in the natural product sylvic acid to make N as the oleophilic group of quaternary ammonium salt surface active agent, N, N-trimethylammonium-N-rosinyl methyl sulfate ammonium.Because of this oleophilic group from natural product, has the luxuriant and rich with fragrance structure of three rings, with the straight chained alkyl as oleophilic group in the traditional quaternary ammonium salt surface active agent tangible difference is arranged structurally, thereby has a favorable biological degradability, simultaneously, N of the present invention, N, N-trimethylammonium-N-rosinyl methyl sulfate ammonium also has microbe killing properties, and can be used as the sterilant with new texture and uses.
The feature of the inventive method is to make raw material with rosin Amine D, prepares N through two-step reaction, N, N-trimethylammonium-N-rosinyl methyl sulfate ammonium.The first step is that methylating reagent prepares N with formaldehyde-formic acid, N-dimethyl rosin Amine D (A); Second step was a solvent with the ethyl acetate, made alkylating reagent and (A) carry out quaterisation to prepare N, N, N-trimethylammonium-N-rosinyl methyl sulfate ammonium with methyl-sulfate.Above-mentioned preparation process can be represented with following reaction formula [1] and [2]:
R be rosinyl as:
Deng.
Fat primary amine is carried out reductive methylation with formaldehyde and formic acid prepare the reaction that tertiary amine is classics, be called Eschweiler-Clarke reaction (H.T.CLARKE, JACS55,1933, P4571-4585), but this reaction is used for the comparison difficulty that methylates of rosin Amine D, because rosin Amine D is sterically hindered bigger.The present invention is by adjusting reacting material ratio, and prolongation reaction times, improvement aftertreatment have prepared N, N-dimethyl rosin Amine D.
A kind of N of the present invention, N, the preparation method of N-trimethylammonium-N-rosinyl methyl sulfate ammonium mainly is: rosin Amine D: formaldehyde: formic acid=1: 25～3: 5～6 (mol ratio) is preferably 1: 3: 5 (mol ratio).Back flow reaction 8～24 hours is preferably 12～16 hours.Backflow stops the back and adds the appropriate hydrochloric acid acidifying, and solution PH is less than 3, distillation then, cooling, the alkalization of repeated hydrogenation sodium hydroxide solution, to water PH greater than 9, tell oil phase.Oil phase adds water and methylene dichloride, and standing demix is removed the inorganic salt in the oil phase, with the solvent in the oil phase steam remove crude product, yield 85～92%.Under nitrogen atmosphere protection,, collect 190～205 ℃/4mmHg fraction, obtain light yellow liquid, be N, N-dimethyl rosin Amine D the crude product underpressure distillation.
Dimethyl rosin Amine D and methyl-sulfate carry out quaterisation with 1: 1.1 mol ratio in ethyl acetate, refluxed 0.5～2 hour, filter with B, get crude product, yield 90.4% is used re-crystallizing in ethyl acetate, get purified product N, N, N-trimethylammonium-N-rosinyl methyl sulfate ammonium, yield 81%.
A kind of N of the present invention, N, the preparation method's of N-trimethylammonium-N-rosinyl methyl sulfate ammonium advantage is: quaternized step is made solvent with ethyl acetate, the product that generates is a white precipitate, and reaction end is easily differentiated, and easily carries out aftertreatment, product yield height, easily purifying.
The N of the present invention's preparation, N, N-trimethylammonium-N-rosinyl methyl sulfate ammonium is the white plates crystallization, 189～192 ℃ of fusing points, active matter content 93% (measure with direct two-phase titration, Yamamoto Methylene Blue ZF is made indicator).The Krafft point is lower than 20 ℃, very easily water-soluble, ethanol, methylene dichloride.Have surfactivity, lowest surface tension is a 33.7mN/ rice (1.0 * 10
-2Mol/L), measure foaming power and stability, foam height 154mm, the foam height 5mm after 3 minutes with the Luo Shi Latherometer.
By the sterilisation effect of Ministry of Health's disinfection technology standard (1988.9) mensuration to gold-coloured staphylococci, minimum inhibitory concentration result is as shown in table 1, and contrasts with geramine.
Table 1N, N, N-trimethylammonium-N-rosinyl sulfate methyl ammonium and geramine
Minimum antibacterial extent of dilution
Embodiment 1
Electric mixer is being housed, reflux condensing tube, add 72.9 gram rosin Amine Ds in the 500ml four-hole boiling flask of thermometer and dropping funnel, stirring slowly adds 85% formic acid 66.7 grams, heating, water-bath cooling down, 50 ℃ of control reaction temperature, add 37% formaldehyde solution, 61.1 grams by dropping funnel, use the electric mantle heating after dropwising instead, to reflux temperature reaction 12 hours.The distillation reaction mixed solution is removed excessive formic acid and formaldehyde etc., adds 20% hydrochloric acid 73.0 grams in reaction mixture, and redistillation removes formic acid removal, and reaction mixture leaves standstill, and is cooled to room temperature.Under agitation slowly add 25% aqueous sodium hydroxide solution 80.0 gram, stir 30 fens kinds after, leave standstill, water PH tells oil phase greater than 9.Add 30～40ml methylene dichloride and 30ml water, stir the back standing demix, oil phase is told, water is incorporated oil phase into 15ml dichloromethane extraction secondary, and oil phase steams and desolventizes to such an extent that dimethyl rosin Amine D crude product 74.1 restrains yield 92%.190～205 ℃/4mmHg yield 80.6% is collected in underpressure distillation under nitrogen atmosphere protection.
Agitator is being housed, thermometer, reflux condensing tube, add in the 250ml four-hole boiling flask of heating jacket by the above-mentioned dimethyl rosin Amine D that makes 26.5 grams, add ethyl acetate 40ml, stir the 12.0 gram methyl-sulfates of adding down, be heated to reflux temperature, the adularescent solid is separated out after ten minutes, 2 hours postcooling of back flow reaction filter reaction mixture with B to room temperature, wash with ethyl acetate, get crude product 30.9 grams, crude product yield 90.4%.Get purified product 27.2 grams, yield 80.9% for twice with re-crystallizing in ethyl acetate.Use direct two-phase titration, Yamamoto Methylene Blue ZF is made indicator and is measured active matter content 93.3%.
Embodiment 2
Electric mixer is being housed, and reflux condensing tube adds 218.7 gram rosin Amine Ds in the 1000ml four-hole boiling flask of thermometer and dropping funnel, stir and add 85% formic acid, 220.1 grams, heating, water-bath cooling down at leisure, 45 ℃ of control reaction temperature add 37% formaldehyde solution, 201.6 grams by dropping funnel.Use electric mantle after dropwising instead and be heated to reflux temperature reaction 16 hours.The distillation reaction mixed solution is removed excessive formic acid and formaldehyde etc., adds 20% hydrochloric acid, 219 grams in reaction mixture, and redistillation removes formic acid removal, and the standing and reacting mixed solution is cooled to room temperature then.Under agitation slowly add 25% aqueous sodium hydroxide solution, 240 grams, stir after 30 minutes, leave standstill, water PH tells oil phase greater than 9.Add the methylene dichloride of 90～110ml and the water of 90ml, stir the back standing demix, tell oil phase, water is incorporated oil phase into the dichloromethane extraction twice of 50ml, steams oil removing phase solution and gets dimethyl rosin Amine D crude product 222.6 grams, yield 92.2%.190～205 ℃/4mmHg fraction is collected in underpressure distillation under nitrogen atmosphere protection, and yield is 80.3%.
Agitator is being housed, thermometer, reflux condensing tube in the 1000ml four-hole boiling flask of heating jacket, adds dimethyl rosin Amine D 160 grams by above-mentioned preparation, ethyl acetate 280 grams, stir adding methyl-sulfate 80 grams down, be heated to reflux temperature, the adularescent solid is separated out after 10 minutes, continue back flow reaction 3 hours, and be cooled to room temperature then.Filter with B, use 80ml ethyl acetate washing leaching cake three times, get crude product 185.8 grams, crude product yield 90.5%.With re-crystallizing in ethyl acetate twice, get refined products 163 grams, yield 79.4%.Use direct two-phase titration, Yamamoto Methylene Blue ZF is made indicator and is measured active matter content 93.1%.189～192 ℃ of fusing points.
Embodiment 3
In the 1000ml four-hole boiling flask of electric mixer, reflux condensing tube, thermometer and dropping funnel is housed, add 182 gram rosin Amine Ds, slowly add 85% formic acid, 146.7 grams under stirring, heating, water-bath cooling, 55 ℃ of control reaction temperature.Add 37% formaldehyde solution, 134.4 grams by dropping funnel.Use the electric mantle heating after dropwising instead, to reflux temperature reaction 10 hours.The distillation reaction mixed solution is removed excessive formic acid and formaldehyde etc., adds 20% hydrochloric acid, 182 grams in reaction mixture, and redistillation removes formic acid removal, and the standing and reacting mixed solution is cooled to room temperature then.Under agitation slowly add 25% aqueous sodium hydroxide solution, 200 grams, stir after 30 minutes, leave standstill, water PH tells oil phase greater than 9.Add 70～90ml methylene dichloride and 60ml water, stir the back standing demix, tell oil phase, water is incorporated oil phase into 40ml dichloromethane extraction twice, steams the oil removing phase solvent and gets dimethyl rosin Amine D crude product 184 grams, yield 91.6%.Underpressure distillation under nitrogen atmosphere protection is collected 190～205 ℃/4mmHg fraction, yield 80.2%.
In the 1000ml four-hole boiling flask of agitator, thermometer, reflux condensing tube, heating jacket is housed, adding is by dimethyl rosin Amine D 106 grams of above-mentioned preparation, add ethyl acetate 200ml, stir adding methyl-sulfate 48.0 grams down, be heated to reflux temperature, the adularescent solid is separated out after 10 minutes, increase along with the reaction times, the white solid of separating out increases, and continues back flow reaction 2.5 hours, is cooled to room temperature then.Filter with B, use 50ml ethyl acetate washing leaching cake three times, get crude product 124 grams, crude product yield 91%.With re-crystallizing in ethyl acetate twice, get refined products 108 grams, productive rate 80%.Use direct two-phase titration, Yamamoto Methylene Blue ZF is made indicator and is measured active matter content 93.2%.189～192 ℃ of fusing points.1% aqueous solution Krafft point is lower than 20 ℃.Gold-coloured staphylococci is measured minimum antibacterial extent of dilution, is 1: 1600 during 10 minutes action time, and its sterilizing power and geramine (dodecyl benzyl dimethyl ammonium chloride) are suitable.
Claims (1)
1. N, N, the preparation method of N-trimethylammonium-N-rosinyl methyl sulfate ammonium, it is characterized in that with the rosin Amine D being raw material through methylating and quaternized two-step reaction prepares, the first step methylation reaction is characterised in that rosin Amine D: formaldehyde: formic acid=1: 3: 5 mol ratio, back flow reaction 8～24 hours, obtain N, N-dimethyl rosin Amine D, the second step quaterisation is characterised in that, makes alkylating reagent with methyl-sulfate, N, the mol ratio of N-dimethyl rosin Amine D and methyl-sulfate is 1: 1.1, and ethyl acetate is a solvent, and reflux temperature reacted 0.5～2 hour down, filtration obtains crude product, get purified product N with re-crystallizing in ethyl acetate, N, N-trimethylammonium-N-rosinyl methyl sulfate ammonium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97111998A CN1059914C (en) | 1997-07-11 | 1997-07-11 | Method for preparation of ammonium methyl N.N.N-trimethyl-N abietylsulfate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97111998A CN1059914C (en) | 1997-07-11 | 1997-07-11 | Method for preparation of ammonium methyl N.N.N-trimethyl-N abietylsulfate |
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| Publication Number | Publication Date |
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| CN1180072A CN1180072A (en) | 1998-04-29 |
| CN1059914C true CN1059914C (en) | 2000-12-27 |
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| CN97111998A Expired - Fee Related CN1059914C (en) | 1997-07-11 | 1997-07-11 | Method for preparation of ammonium methyl N.N.N-trimethyl-N abietylsulfate |
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| CN101486657B (en) * | 2009-01-05 | 2012-05-02 | 盐城工学院 | A method for preparing 3-rosinamino-2-hydroxypropyltrimethylammonium chloride |
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Non-Patent Citations (3)
| Title |
|---|
| J.AM CHEM SOC 55 1933.11.1 H.T.CLARKE ET AL THE ACTION OF FORMALDEHYDE ON AMINES AND ANINO ANIDS * |
| J.AM CHEM SOC 55 1933.11.1 H.T.CLARKE ET AL THE ACTION OF FORMALDEHYDE ON AMINES AND ANINO ANIDS;表面活性剂工业1994(二)P7-17 1994.1.1 王延，宋湛谦，松香类表面活性剂的开发和应用 * |
| 表面活性剂工业1994(二)P7-17 1994.1.1 王延，宋湛谦，松香类表面活性剂的开发和应用 * |
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