CN102304067A - Method for preparing gydroxysulfobetaine amphoteric surface active agent including polyether chain segment - Google Patents
Method for preparing gydroxysulfobetaine amphoteric surface active agent including polyether chain segment Download PDFInfo
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Abstract
The invention relates to a method for preparing a gydroxysulfobetaine amphoteric surface active agent including a polyether chain segment, belonging to the technical field of preparation of surface active agents. The gydroxysulfobetaine amphoteric surface active agent including the polyether chain segment is prepared by taking fatty amine polyoxyethylene ether and 3-chlorine-2-hydroxyl propane sodium sulfonate as raw materials. The gydroxysulfobetaine amphoteric surface active agent including the polyether chain segment is shown as a chemical structural formula in the specification. According to the gydroxysulfobetaine amphoteric surface active agent including the polyether chain segment synthesized by using the method disclosed by the invention, three hydrophilic groups consisting of polyoxyethenyl, quaternary ammonium salt and sulfonyl and hydrophobic alkyl are included; the gydroxysulfobetaine amphoteric surface active agent including the polyether chain segment has the two good surface activities of the non-ionic and amphoteric surface active agent; in addition, besides the good performance of the traditional gydroxysulfobetaine amphoteric surface active agent, the performances, such as water solubility, detergency, emulsifiability, dispersibility, solubilising power and the like, are improved obviously.
Description
Technical field
The present invention relates to a kind of sultaine amphoterics, be specially a kind of preparation method who contains the hydroxy sulfo lycine amphoterics of polyether segment, metal surface promoting agent preparing technical field.
Background technology
In tensio-active agent, amphoterics has fabulous stability in hard water, the performance of electrolyte-resistant because of having anionic group and cation group in its structure simultaneously; Low toxicity, readily biodegradable; To skin and eyes low irritant; Compatibleness is good.Simultaneously, they also have the characteristic that negatively charged ion and cats product have, like well emulsify property, dispersiveness, static resistance and flexible smooth performance; Certain bactericidal properties and but mouldiness.In a word, it is the tensio-active agent of one type of excellent performance, therefore in recent years both at home and abroad the annual growth of amphoterics be far longer than the tensio-active agent of other type.In amphoterics, people are to the existing considerable understanding of the characteristic of " carboxybetaine ", if with sulfo group substituted carboxylic acid group, the change platform thing that obtains just is called " sultaine ".
Show through performance test; The sultaine performance is more comprehensive; All advantages that not only have carboxybetaine such as dodecyl carboxybetaine (BS-12); Also have unique advantage such as resisting high-concentration acid, alkali, salt, therefore receive people's attention day by day, trimethyl-glycine develops into trend to sulfo groupization.Sultaine is as new type amphoteric surfactant; Fields such as daily-use chemical industry, the oily positive displacement of reservoir oil have been applied to; Through developing and applying; Also will be used widely at aspects such as agricultural chemicals, leather, weaving, latex and preparation auxiliary agents, this will help improving the auxiliary agent level of China's fine chemistry industry industry.
Find after deliberation; If will make the sultaine amphoterics have bigger surfactivity; Its positive and negative electric charge intermediary carbonatoms should >=3, so the azochlorosulfonate propyl lycine amphoterics is one type of even more important sultaine amphoterics.About synthesizing of azochlorosulfonate propyl lycine amphoterics; Past is extensively adopted long chain tertiary amine and 1, and 3-sulphur propiolactone reacts and makes, and 1; 3-sulphur propiolactone is that a kind of reactivity is strong, easy to use, the impure few sulfoalkyl reagent of product; But sultone is the chemical reagent of murther, and animal is had carcinogenesis, therefore needs to seek its alternative articles for use.In patent US4381980, introduce to adopt chlorallylene and sulphite pairing and long chain tertiary amine reaction to make a kind of azochlorosulfonate propyl lycine amphoterics, but reaction needs in potheater, carry out, reaction conditions is harshness comparatively.People adopted epoxy chloropropane and sodium sulfite anhy 96 pairing to make a kind of new sultaine amphoterics as sulfo group reagent afterwards, were the hydroxy sulfo lycine amphoterics.
The hydroxy sulfo lycine amphoterics be one than new variety; Excellent performance is comprehensive; Receive people's attention day by day; Yet it all exists the water-soluble problem poor than other amphotericses with other sultaine amphoterics; To this problem, have and researched and proposed in the hydrophobic chain of sultaine the oxyethyl group of introducing possess hydrophilic property and improve that it is water-soluble, interim report adopted thanomin reacted with hydrochloric ether and synthesized the tertiary amine that contains an oxyethyl group nineteen ninety-five " daily chemical industry " the 1st; Generate etherifying agent 3-chloro-2-hydroxypropanesulfonic acid sodium with the reaction of epoxy chloropropane and sodium sulfite anhy 96 then, the reactive tertiary amine that contains oxyethyl group with 3-chloro-2-hydroxypropanesulfonic acid sodium and above-mentioned synthetic at last obtains containing the hydroxy sulfo lycine of 1～2 oxyethyl group; " Wuxi Light Industry Univ.'s journal " the 4th phase in 1996 report adopts glycol chlorohydrin under sulphuric acid catalysis, to make monochloro generation two polyoxyethylene glycol, monochloro generation three polyoxyethylene glycol, monochloro generation four polyoxyethylene glycol with reacting ethylene oxide; Then with N; N-dimethylated propyl diethylenetriamine reaction make N-oxyethyl group replacement-3-(N '; N '-dimethylin) propylamine; Methyl dodecanoate reaction makes 3-(N '-oxyethyl group replace the dodecanoyl amido) propyl-dimethyl amine again, and then makes the hydroxy sulfo lycine amphoterics that contains 1～4 oxyethyl group with the reaction of 3-chloro-2-hydroxypropanesulfonic acid sodium; Introduce among the disclosed Poland Patent PL169323 in 1996 and adopt the tertiary amine and the epoxy chloropropane of band T 46155 (4～8) in 40～100 ℃ of water, to react 10h, and then make a kind of hydroxy sulfo lycine amphoterics that contains polyether segment (4～8) at 5～80 ℃ of reaction 1h with 10～12% aqueous solution of sodium bisulfite.But these compound methods or midbody are synthetic cumbersome; Synthesis step is more; Reaction times is longer; And it is less all to exist hydrophilic oxyethyl group content, and the water-soluble of gained hydroxy sulfo lycine had significant improvement, and can not give play to the synergy of both sexes/nonionogenic tenside.
Summary of the invention
The objective of the invention is to overcome the prior art deficiency, provide that a kind of raw material is easy to get, the preparation method of practical process, environment friendly and pollution-free, production cost is low and application performance the is good hydroxy sulfo lycine amphoterics that contains polyether segment.
For achieving the above object, the present invention adopts following technical scheme:
A kind of hydroxy sulfo lycine amphoterics that contains polyether segment has following chemical structural formula:
A kind of preparation method who contains the hydroxy sulfo lycine amphoterics of polyether segment; It is characterized in that adopting solid base catalyst; With aliphatic amine polyoxyethylene ether and 3-chloro-2-hydroxypropanesulfonic acid sodium is raw material, under 40～105 ℃ condition, and reaction 2～20h; Reaction finishes after-filtration and removes solid base catalyst; Obtain the hydroxy sulfo lycine amphoterics 2～3 times through methanol wash, wherein aliphatic amine polyoxyethylene ether is 1: 1.05～1.5 with the ratio of the amount of substance of 3-chloro-2-hydroxypropanesulfonic acid sodium, and the add-on of solid alkali is 1～50 ‰ of 3-chloro-2-hydroxypropanesulfonic acid sodium and an aliphatic amine polyoxyethylene ether gross weight.
Said solid base catalyst is 201 * 7 strong alkaline quaternary ammonium I type anionite-exchange resin, 201 * 2 strong alkaline quaternary ammonium I type anionite-exchange resin, 201 * semi-finals alkalescence quaternary amine I type anionite-exchange resin; 201 * Final 8 alkalescence quaternary amine I type anionite-exchange resin, D201 macroporous strong basic quaternary amine I type anionite-exchange resin, D202 macroporous strong basic quaternary amine II type anionite-exchange resin; 301 weakly alkaline vinylbenzene anionite-exchange resin, 303 * 2 weakly alkaline vinylbenzene anionite-exchange resin, 331 type weakly alkaline epoxy type anion exchange resins; D301 macroreticular weakly base vinylbenzene anionite-exchange resin; D302 macroreticular weakly base vinylbenzene anionite-exchange resin, 4A type molecular sieve solid alkali, X type molecular sieve solid alkali; The Y zeolite solid alkali; L type molecular sieve solid alkali, MCM-41 molecular sieve solid alkali, SBA-15 molecular sieve solid alkali, Al
2O
3A kind of in load alkali or the activated carbon supported alkali.
Temperature of reaction is 70～90 ℃ in the said reaction process; Reaction times is 2～10h.
The present invention has following outstanding advantage and positively effect:
1, rationally select the solid alkali catalyst for use, have higher reaction preference, etching apparatus not, reaction finishes can be through removing by filter, and recyclable.
2, through optimized choice repeatedly to reasonable adjustment, temperature of reaction and the time of raw material add-on and catalyst proportion, make the present invention rationally advanced, facility investment economizes, and economic benefit is higher, and environmental pollution is less.
3, contain in the hydroxy sulfo lycine amphoterics molecule of polyether segment by synthetic of the present invention and contain polyoxyethylene groups, quaternary ammonium salt base and three kinds of hydrophilic radicals of sulfonic group and hydrophobic alkyl; The dual good surface that has possessed nonionic and amphoterics is active; Product is except that having the good performance of traditional hydroxy sulfo lycine amphoterics, and water-soluble, washing, emulsification, dispersiveness and solubilising etc. have all had tangible improvement.
Embodiment
Below be that embodiment will further describe invention, but the present invention do not produced any restriction.
Embodiment 1:
(1) preparation of 3-chloro-2-hydroxypropanesulfonic acid sodium: in churned mechanically four-hole boiling flask is housed with 20.8gNaHSO
3Be dissolved in and process saturated solution in the water, add phase-transfer catalyst, under nitrogen protection, stir and be warming up to 75 ℃, begin to drip the 18.51g epoxy chloropropane, the control dropping time is 60min; After dropwising, continue insulation reaction 0.5h; Pour out product while hot, place ice-water bath to cool off, treat that temperature reduces to below 10 ℃, vacuum filtration is isolated solids, after oven for drying, obtains 3-chloro-2-hydroxypropanesulfonic acid sodium white powdery solid.
(2) contain the preparation of the hydroxy sulfo lycine amphoterics of polyether segment: in churned mechanically four-hole boiling flask is housed, add the 3-chloro-2-hydroxypropanesulfonic acid sodium that 20.64g makes; 62.31g amino dodecane T 46155 (10) ether; 4.15g 201 * 7 strong alkaline quaternary ammonium I type anionite-exchange resin; Stirring is warming up to 70 ℃ and carries out quaterisation, reaction times 2h, and reaction finishes after the solids removed by filtration catalyzer; Obtain containing the hydroxy sulfo lycine amphoterics of polyether segment again for 2～3 times with methanol wash, the transformation efficiency 96.7% of amino dodecane T 46155 (10) ether.
The hydroxy sulfo lycine amphoterics that contains polyether segment that present embodiment makes has following structure:
Embodiment 2:
(1) preparation of 3-chloro-2-hydroxypropanesulfonic acid sodium: in churned mechanically four-hole boiling flask is housed with 21.84gNaHSO
3Be dissolved in and process saturated solution in the water, add phase-transfer catalyst, under nitrogen protection, stir and be warming up to 45 ℃, begin to drip the 18.46g epoxy chloropropane, the control dropping time is 120min; After dropwising, continue insulation reaction 5h; Pour out product while hot, place ice-water bath to cool off, treat that temperature reduces to below 10 ℃, vacuum filtration is isolated solids, after oven for drying, obtains 3-chloro-2-hydroxypropanesulfonic acid sodium white powdery solid.
(2) contain the preparation of the hydroxy sulfo lycine amphoterics of polyether segment: in churned mechanically four-hole boiling flask is housed, add the 3-chloro-2-hydroxypropanesulfonic acid sodium that 22.61g makes; 106.35g amino dodecane T 46155 (20) ether; 3.87g 4A type molecular sieve solid alkali; Stirring is warming up to 80 ℃ and carries out quaterisation, reaction times 5h, and reaction finishes after the solids removed by filtration catalyzer; Obtain containing the hydroxy sulfo lycine amphoterics of polyether segment again for 2～3 times with methanol wash, the transformation efficiency 97.1% of amino dodecane T 46155 (20) ether.
The hydroxy sulfo lycine amphoterics that contains polyether segment that present embodiment makes has following structure:
Embodiment 3:
(1) preparation of 3-chloro-2-hydroxypropanesulfonic acid sodium: in churned mechanically four-hole boiling flask is housed with 11.44gNaHSO
3Be dissolved in and process saturated solution in the water, add phase-transfer catalyst, under nitrogen protection, stir and be warming up to 60 ℃, begin to drip the 9.25g epoxy chloropropane, the control dropping time is 100min; After dropwising, continue insulation reaction 5h; Pour out product while hot, place ice-water bath to cool off, treat that temperature reduces to below 10 ℃, vacuum filtration is isolated solids, after oven for drying, obtains 3-chloro-2-hydroxypropanesulfonic acid sodium white powdery solid.
(2) contain the preparation of the hydroxy sulfo lycine amphoterics of polyether segment: in churned mechanically four-hole boiling flask is housed, add the 3-chloro-2-hydroxypropanesulfonic acid sodium that 14.75g makes; 119.15g amino dodecane T 46155 (50) ether; 0.67g activated carbon supported alkali; Stirring is warming up to 60 ℃ and carries out quaterisation, reaction times 10h, and reaction finishes after the solids removed by filtration catalyzer; Obtain containing the hydroxy sulfo lycine amphoterics of polyether segment again for 2～3 times with methanol wash, the transformation efficiency 96.1% of amino dodecane T 46155 (50) ether.
The hydroxy sulfo lycine amphoterics that contains polyether segment that present embodiment makes has following structure:
Embodiment 4:
(1) preparation of 3-chloro-2-hydroxypropanesulfonic acid sodium: in churned mechanically four-hole boiling flask is housed with 10.4gNaHSO
3Be dissolved in and process saturated solution in the water, add phase-transfer catalyst, under nitrogen protection, stir and be warming up to 60 ℃, begin to drip the 9.25g epoxy chloropropane, the control dropping time is 60min; After dropwising, continue insulation reaction 2h; Pour out product while hot, place ice-water bath to cool off, treat that temperature reduces to below 10 ℃, vacuum filtration is isolated solids, after oven for drying, obtains 3-chloro-2-hydroxypropanesulfonic acid sodium white powdery solid.
(2) contain the preparation of the hydroxy sulfo lycine amphoterics of polyether segment: in churned mechanically four-hole boiling flask is housed, add the 3-chloro-2-hydroxypropanesulfonic acid sodium that 7.08g makes; 26.19g tetradecy lamine T 46155 (15) ether; 0.266g D201 macroporous strong basic quaternary amine I type anionite-exchange resin; Stirring is warming up to 85 ℃ and carries out quaterisation, reaction times 5h, and reaction finishes after the solids removed by filtration catalyzer; Obtain containing the hydroxy sulfo lycine amphoterics of polyether segment again for 2～3 times with methanol wash, the transformation efficiency 96.3% of tetradecy lamine T 46155 (15) ether.
The hydroxy sulfo lycine amphoterics that contains polyether segment that present embodiment makes has following structure:
Embodiment 5:
(1) preparation of 3-chloro-2-hydroxypropanesulfonic acid sodium: in churned mechanically four-hole boiling flask is housed with 10.4gNaHSO
3Be dissolved in and process saturated solution in the water, add phase-transfer catalyst, under nitrogen protection, stir and be warming up to 45 ℃, begin to drip the 8.79g epoxy chloropropane, the control dropping time is 120min; After dropwising, continue insulation reaction 5h; Pour out product while hot, place ice-water bath to cool off, treat that temperature reduces to below 10 ℃, vacuum filtration is isolated solids, after oven for drying, obtains 3-chloro-2-hydroxypropanesulfonic acid sodium white powdery solid.
(2) contain the preparation of the hydroxy sulfo lycine amphoterics of polyether segment: in churned mechanically four-hole boiling flask is housed, add the 3-chloro-2-hydroxypropanesulfonic acid sodium that 4.915g makes; 26.82g cetylamine T 46155 (25) ether; 0.381g MCM-41 molecular sieve solid alkali; Stirring is warming up to 80 ℃ and carries out quaterisation, reaction times 7h, and reaction finishes after the solids removed by filtration catalyzer; Obtain containing the hydroxy sulfo lycine amphoterics of polyether segment again for 2～3 times with methanol wash, the transformation efficiency 96.2% of cetylamine T 46155 (25) ether.
The hydroxy sulfo lycine amphoterics that contains polyether segment that present embodiment makes has following structure:
Embodiment 6:
(1) preparation of 3-chloro-2-hydroxypropanesulfonic acid sodium: in churned mechanically four-hole boiling flask is housed with 11.44gNaHSO
3Be dissolved in and process saturated solution in the water, add phase-transfer catalyst, under nitrogen protection, stir and be warming up to 60 ℃, begin to drip the 9.25g epoxy chloropropane, the control dropping time is 100min; After dropwising, continue insulation reaction 5h; Pour out product while hot, place ice-water bath to cool off, treat that temperature reduces to below 10 ℃, vacuum filtration is isolated solids, after oven for drying, obtains 3-chloro-2-hydroxypropanesulfonic acid sodium white powdery solid.
(2) contain the preparation of the hydroxy sulfo lycine amphoterics of polyether segment: in churned mechanically four-hole boiling flask is housed, add the 3-chloro-2-hydroxypropanesulfonic acid sodium that 8.55g makes; 60.87g stearylamine T 46155 (40) ether; 1.735g SBA-15 molecular sieve solid alkali; Stirring is warming up to 60 ℃ and carries out quaterisation, reaction times 6h, and reaction finishes after the solids removed by filtration catalyzer; Obtain containing the hydroxy sulfo lycine amphoterics of polyether segment again for 2～3 times with methanol wash, the transformation efficiency 95.9% of stearylamine T 46155 (40) ether.
The hydroxy sulfo lycine amphoterics that contains polyether segment that present embodiment makes has following structure:
Embodiment 7:
(1) preparation of 3-chloro-2-hydroxypropanesulfonic acid sodium: in churned mechanically four-hole boiling flask is housed with 11.44gNaHSO
3Be dissolved in and process saturated solution in the water, add phase-transfer catalyst, under nitrogen protection, stir and be warming up to 60 ℃, begin to drip the 9.25g epoxy chloropropane, the control dropping time is 100min; After dropwising, continue insulation reaction 5h; Pour out product while hot, place ice-water bath to cool off, treat that temperature reduces to below 10 ℃, vacuum filtration is isolated solids, after oven for drying, obtains 3-chloro-2-hydroxypropanesulfonic acid sodium white powdery solid.
(2) contain the preparation of the hydroxy sulfo lycine amphoterics of polyether segment: in churned mechanically four-hole boiling flask is housed, add the 3-chloro-2-hydroxypropanesulfonic acid sodium that 9.83g makes; 28.45g octyl amine T 46155 (10) ether; 0.231g 4A molecular sieve solid alkali; Stirring is warming up to 80 ℃ and carries out quaterisation, reaction times 7h, and reaction finishes after the solids removed by filtration catalyzer; Obtain containing the hydroxy sulfo lycine amphoterics of polyether segment again for 2～3 times with methanol wash, the transformation efficiency 96.9% of octyl amine T 46155 (10) ether.
The hydroxy sulfo lycine amphoterics that contains polyether segment that present embodiment makes has following structure:
Embodiment 8:
(1) preparation of 3-chloro-2-hydroxypropanesulfonic acid sodium: in churned mechanically four-hole boiling flask is housed with 11.44gNaHSO
3Be dissolved in and process saturated solution in the water, add phase-transfer catalyst, under nitrogen protection, stir and be warming up to 60 ℃, begin to drip the 9.25g epoxy chloropropane, the control dropping time is 100min; After dropwising, continue insulation reaction 5h; Pour out product while hot, place ice-water bath to cool off, treat that temperature reduces to below 10 ℃, vacuum filtration is isolated solids, after oven for drying, obtains 3-chloro-2-hydroxypropanesulfonic acid sodium white powdery solid.
(2) contain the preparation of the hydroxy sulfo lycine amphoterics of polyether segment: in churned mechanically four-hole boiling flask is housed, add the 3-chloro-2-hydroxypropanesulfonic acid sodium that 5.91g makes; 59.31g two amino dodecane T 46155 (60) ethers; 0.26g activated carbon supported alkali; Stirring is warming up to 60 ℃ and carries out quaterisation, reaction times 6h, and reaction finishes after the solids removed by filtration catalyzer; Obtain containing the hydroxy sulfo lycine amphoterics of polyether segment again for 2～3 times with methanol wash, the transformation efficiency 95.6% of two amino dodecane T 46155 (60) ethers.
The hydroxy sulfo lycine amphoterics that contains polyether segment that present embodiment makes has following structure:
Claims (5)
1. preparation method who contains the hydroxy sulfo lycine amphoterics of polyether segment is characterized in that this hydroxy sulfo lycine amphoterics that contains polyether segment has following chemical structural formula:
2. preparation method who contains the hydroxy sulfo lycine amphoterics of polyether segment; It is characterized in that: adopt solid base catalyst; With aliphatic amine polyoxyethylene ether and 3-chloro-2-hydroxypropanesulfonic acid sodium is raw material; Under 40～105 ℃ condition; Reaction 2～20h, wherein aliphatic amine polyoxyethylene ether is 1: 1.05～1.5 with the ratio of the amount of substance of 3-chloro-2-hydroxypropanesulfonic acid sodium, the add-on of solid alkali is 1～50 ‰ of 3-chloro-2-hydroxypropanesulfonic acid sodium and an aliphatic amine polyoxyethylene ether gross weight.
3. according to the preparation method of the said a kind of hydroxy sulfo lycine amphoterics of claim 2, it is characterized in that: said solid base catalyst is 201 * 7 strong alkaline quaternary ammonium I type anionite-exchange resin, 201 * 2 strong alkaline quaternary ammonium I type anionite-exchange resin; 201 * semi-finals alkalescence quaternary amine I type anionite-exchange resin, 201 * Final 8 alkalescence quaternary amine I type anionite-exchange resin, D201 macroporous strong basic quaternary amine I type anionite-exchange resin; D202 macroporous strong basic quaternary amine II type anionite-exchange resin, 301 weakly alkaline vinylbenzene anionite-exchange resin, 303 * 2 weakly alkaline vinylbenzene anionite-exchange resin; 331 type weakly alkaline epoxy type anion exchange resins, D301 macroreticular weakly base vinylbenzene anionite-exchange resin, D302 macroreticular weakly base vinylbenzene anionite-exchange resin; 4A type molecular sieve solid alkali; X type molecular sieve solid alkali, Y zeolite solid alkali, L type molecular sieve solid alkali; MCM-41 molecular sieve solid alkali, SBA-15 molecular sieve solid alkali, Al
2O
3A kind of in load alkali or the activated carbon supported alkali.
4. according to the preparation method of the said a kind of hydroxy sulfo lycine amphoterics of claim 2, it is characterized in that temperature of reaction is 70～90 ℃.
5. according to the preparation method of the said a kind of hydroxy sulfo lycine amphoterics of claim 2, it is characterized in that the reaction times is 2～10h.
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