CN103922997A - Synthetic method of pyridinium hydroxy propyl sulfobetaine - Google Patents
Synthetic method of pyridinium hydroxy propyl sulfobetaine Download PDFInfo
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- CN103922997A CN103922997A CN201410146820.1A CN201410146820A CN103922997A CN 103922997 A CN103922997 A CN 103922997A CN 201410146820 A CN201410146820 A CN 201410146820A CN 103922997 A CN103922997 A CN 103922997A
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- hydroxy propyl
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- propyl sulfobetaine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Abstract
The invention relates to a synthetic method of pyridinium hydroxy propyl sulfobetaine. The synthetic method comprises the following steps: sufficiently dissolving hydrosulphite or pyrosulfite in water at normal temperature, adding sodium sulfite as an auxiliary sulfonating agent to adjust the pH value of the system to be 5.2-5.5, and then adding polyether F-6 as a catalyst; then adding a complexing agent, controlling the environment conditions, adding epichlorohydrin, and carrying out loop-opening reaction to obtain 3-chloro-2-hydroxy propanesulfonate; adding pyridine to the system, controlling the temperature to carry out reflux reaction, adding triethylamine as an impurity removing agent, reacting for 1 hour, then dehydrating and decoloring, adjusting the pH to 2-5, and adding 4-hydroxyl-2, 2, 6, 6-tetramentylniperidine-1-oxygen radical as a stabilizer and a vitamin C derivative to obtain an aqueous solution of the pyridinium hydroxy propyl sulfobetaine. The pyridinium hydroxy propyl sulfobetaine synthesized by the synthetic method is produced by adopting a one-pot method, which accords with the electroplating industry development demands at present; the pyridinium hydroxy propyl sulfobetaine is low in impurity content, good in appearance and low in production cost.
Description
Technical field
The invention belongs to nickel plating intermediate pyridinium hydroxy propyl sulfobetaine novel preparation method, it is a kind of electroplating additive in high current density region with light, leveling excellent property.
Background technology
Pyridinium hydroxy propyl sulfobetaine is a kind of electroplating intermediate, and sterling is white crystal, commonly content between 40%-50%, pH value is colourless to weak yellow liquid product 3-5's.No. CAS: 3918-73-8, molecular formula: C
8h
11naO
4s, molecular weight: 217.24.
Pyridinium hydroxy propyl sulfobetaine (PPS-OH) has good light and leveling effect in electronickelling, especially good high current density region leveling effect spy.As the base additive in nickel plating bath, its consumption, be 20-50g/kAH, consumption 50-500mg/L, the huge market demand.At present, pyridinium hydroxy propyl sulfobetaine (PPS-OH) liquid product only has German La Xige, BASF AG to produce abroad, domestic colleague mainly adopts two-step approach preparation, its production cost is high, wastewater flow rate is large, product is unstable, the production cycle is long, thereby causes the domestic main or high-quality PPS-OH product of dependence on import.
Less to the synthetic report of PPS-OH both at home and abroad at present, mainly contain French Patent FR1390191, patent of the same name is the synthesis preparation method that GB1006139, US3280130, DE19620724 and Chinese patent CN102161639A disclose this product, there is isomer in the synthetic method that wherein French Patent is mentioned, end reaction yield is lower, application effect of products is poor, is not suitable for suitability for industrialized production.I CN102161639A of house journal is the new synthetic method proposing in conjunction with foreign data, to the suitability for industrialized production of domestic this product, provides important references suggestion.
Its synthetic method is also divided into two steps:
The first step: 3-chlorine-2-hydroxyl propanesulfonate synthetic
Under normal temperature condition, by Na
2s0
3, Na
2s
2o
5with after water stirring and dissolving, add catalyzer, be warming up between 40-80 ℃, pass into protection of inert gas, slowly drip epoxy chloropropane, after dripping off, between 40-80 ℃, be incubated 2 hours, after the de-part water of decompression 3-chlorine-2-hydroxyl propanesulfonate.
Second step: pyridinium hydroxy propyl sulfobetaine synthetic
3-chlorine-2-hydroxyl propane sulfonic acid sodium is dissolved in to water, add again effective catalyst 1,4,7,13-, tetra-oxa-s-10-azepine-2,3-benzo ring 15-2-alkene, between 30-100 ℃, with pyridine reaction 6-12 hour, part water is sloughed in decompression, finally by crossing decolouring removal of impurities, obtains the pyridinium hydroxy propyl sulfobetaine aqueous solution.
Its reaction principle is:
There is following shortcoming in synthesis of hydroxy propane sulfonic acid pyridinium salt according to the method described above;
Through HPLC, analyze to find that foreign matter content is higher, in application, show as that coating fragility is large, obfuscation electroplating; Secondly foreign matter content is higher larger on the impact of product colourity, and the product that shows as production is dark compared with external product colourity, is faint yellow to yellow; The product of producing is according to the method described above long placed in the rear metachromatism that easily occurs, shows as redden/yellow; Pyridine large usage quantity and recovery difficulty in such scheme, cause raw materials for production waste serious.
The today day by day becoming more meticulous at nickel plating industry development, said synthesis route has been difficult to produce the high-end product that becomes more meticulous that can meet industry needs.
Summary of the invention
The object of the invention is to improve the deficiencies in the prior art, provides that a kind of foreign matter content that meets current electroplating industry demand for development is low, outward appearance good, the preparation method of the pyridinium hydroxy propyl sulfobetaine of low production cost.
The present invention is achieved through the following technical solutions: a kind of synthetic method of pyridinium hydroxy propyl sulfobetaine, and its step comprises:
(1) intermediate 3-chlorine-2-hydroxyl propane sulfonate is synthetic
Under normal temperature condition, after hydrosulphite or pyrosulfite are fully dissolved in water, adding auxiliary sulphonating agent S-WAT regulation system pH value is between 5.2-5.5, after add catalyzer polyethers F-6; Add complexing agent, the condition that controls environment also adds epoxy chloropropane again, ring-opening reaction occurs and obtain 3-chlorine-2-hydroxyl propane sulfonate.
(2) pyridinium hydroxy propyl sulfobetaine is synthetic
In above-mentioned system, add again pyridine, after temperature control back flow reaction, add cleaner triethylamine, react 1 hour, dehydration and decolorization regulate pH value for 2-5, adds stablizer 4-hydroxyl-2 afterwards, 2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, obtain the aqueous solution of product pyridinium hydroxy propyl sulfobetaine.
Described catalyzer polyethers F-6 consumption is the 0.04-0.07% of system total amount quality.
Described stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, its consumption is 0.02% of system total amount.
Described complexing agent citric acid, its consumption is the 0.003-0.005% of pyrosulfite total mass.
During described epoxy chloropropane generation ring-opening reaction, in the hierarchy of control, temperature is 40-70 ℃, and passes into nitrogen as protection gas.
During described epoxy chloropropane generation ring-opening reaction, epoxy chloropropane slowly need to be splashed into, and its consumption and Sodium Pyrosulfite mol ratio are 1:0.51-0.52.
Described system reaction obtains, after 3-chlorine-2-hydroxyl propane sulfonate, directly adding pyridine, and the mol ratio of its consumption and epoxy chloropropane is 0.93:1.
After described system adds pyridine, be warming up to back flow reaction 10-14 hour between 95-110 ℃.
Described cleaner triethylamine, its addition is the 5-7.5% of pyridine total mass.
The preferred technical solution of the present invention is: under normal temperature condition, after sodium bisulfite or Sodium Pyrosulfite are fully dissolved in water, add auxiliary sulphonating agent S-WAT regulation system pH value to add catalyzer polyethers F-6(after between 5.2-5.5: vinyl carbinol and oxyethane, epoxypropane polymer), its consumption is the 0.04-0.07% of system total amount quality.In this system, add citric acid as complexing agent, its consumption is the 0.003-0.005% of Sodium Pyrosulfite total amount quality again.After this system is warming up to 40-70 ℃, pass into nitrogen as protection gas, slowly drip epoxy chloropropane under this condition, its consumption and Sodium Pyrosulfite mol ratio are 1:(0.51-0.52).Above-mentioned reaction obtains intermediate product 3-chlorine-2-hydroxyl propane sulfonate.
In above-mentioned system, add appropriate pyridine, the mol ratio of its consumption and epoxy chloropropane is 0.93:1 again.Between 95-110 ℃ of system intensification, after back flow reaction 10-14 hour, then to add cleaner triethylamine, its addition be the 5-7.5% of pyridine consumption, reacts 1 hour.After this system dehydration and decolorization, regulate pH value between 2-5, add stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, its consumption is 0.02% of system total amount, obtains pyridinium hydroxy propyl sulfobetaine (PPS-OH) aqueous products.
Reaction principle of the present invention is as follows:
Synthesis of hydroxy propane sulfonic acid pyridinium salt of the present invention (PPS-OH), this process is one kettle way, does not need isolation of intermediate products to get final product subsequent production; And control condition and use catalyzer, complexing agent, stablizer etc. in a plurality of reactions, can strictly control pyridine in product and the content of pyridine derivate.Use low bubble catalyzer polyethers F-6(: vinyl carbinol and oxyethane, epoxypropane polymer), can accelerate speed of reaction and improve transformation efficiency, avoid the abundant punching material that brings of follow-up decompression dehydration process system foam to lose simultaneously, improve reaction conversion ratio.The formation reaction of intermediate product 3-chlorine-2-hydroxyl propane sulfonic acid sodium, control condition pH value is between 5.2-5.5, suppresses raw material hydrolysis, can effectively reduce the content of pyridine derivate in product.In reaction, add citric acid to do after complexing agent, resultant metal total ion concentration is controlled at below 10ppm, effectively avoids metal ion and pyridine derivate effect and causes product variable color, has improved application effect of products simultaneously.In reaction, finish to add stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives can make the colourity of product guarantee in 50#(platinum cobalt colorimetry) below the look that remains unchanged for a long period of time, raising product quality.In reaction process, epoxy chloropropane and pyridine consumption mol ratio are 1:0.93, when guaranteeing high yield, greatly reduce product cost, have reduced follow-up pyridine recycling step, meet Green Chemistry development course.Reaction finishes to add cleaner triethylamine can effectively go out pyridine and its derivatives in product and has improved application effect of products, reduces coating fragility and blackout phenomenon.
Embodiment
By the following specific examples further illustrate the invention:
Example 1
In the 500ml tetra-neck flasks with mechanical stirring, thermometer, reflux condensing tube, constant pressure funnel, add deionized water (335g, 18.59mol), Sodium Pyrosulfite (97g, 0.51mol), fully stirs and makes after its dissolving, add auxiliary sulphonating agent S-WAT (11.57g, 0.091mol) regulation system pH is 5.5, adds 0.2552g catalyzer polyethers F-6(vinyl carbinol and oxyethane, epoxypropane polymer), citric acid 0.0028g.System passes into nitrogen protection after being warming up to 60-65 ℃; slowly drip epoxy chloropropane (92.31g, 1.0mol), controlling dropping temperature is between 60-65 ℃; after dripping between this 60-65 ℃ insulation reaction 4 hours, be warming up to afterwards 70-75 ℃ of insulation reaction 1 hour.Insulation reaction finishes to add pyridine (73.77g, 0.93mol), is warming up to 90-105 ℃ of back flow reaction 10 hours.Add afterwards 4g cleaner triethylamine, after decompression dehydration decolouring, with between hydrochloric acid regulation system pH value 2-5, add stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives obtain colourity and are less than 50#(platinum cobalt colorimetry) light yellow transparent liquid.
Respond well through electroplating application testing, high current density region coating Bai Liangwu fragility free of pinholes, analyzes its yield through HPLC and reaches 90.03%, and before contrast, synthetic schemes product impurity is lower, and colourity is less, and room temperature keeps in Dark Place and without color and luster, stablizes for 1 year.
Example 2
In the 2000ml tetra-neck flasks with mechanical stirring, thermometer, reflux condensing tube, constant pressure funnel, add deionized water (775g, 43mol), Sodium Pyrosulfite (194.20g, 1.02mol), fully stirs and makes after its dissolving, add auxiliary sulphonating agent S-WAT (20.42g, 0.162mol) regulation system pH value is 5.35, adds 0.933g catalyzer polyethers F-6(: vinyl carbinol and oxyethane, epoxypropane polymer), complexing agent citric acid 0.058g.System passes into nitrogen protection after being warming up to 65-70 ℃, slowly drips epoxy chloropropane (185.07g, 2.0mol).Be added dropwise to complete between rear 65-70 ℃ insulation reaction 3 hours, be warming up to afterwards 75-80 ℃ of insulation reaction 1 hour.Insulation reaction finishes to add pyridine (147.66g, 1.86mol), and is warming up to back flow reaction between 95-105 ℃, refluxes and finishes to add 11.07g cleaner triethylamine.After decompression dehydration decolouring, with adding 2.66g stablizer 4-hydroxyl-2 after hydrochloric acid regulation system pH value to 3.5,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, obtain micro-yellow transparent clarification PPS-OH aqueous products.
Through HPLC ultra-violet analysis yield, reach 91.63%, it is that patent CN102161639A synthetic method product impurity accounting is about 1.3-1.5% before 0.55%(that impurity accounts for main peak ratio), colourity is 25#(platinum cobalt colorimetry), electroplate test piece applied analysis good.
Example 3
In 3000L standard reaction still, add 1600kg deionized water, stir the lower Sodium Pyrosulfite (500Kg that drops into, 2.63kmol) after dissolving, add S-WAT (38kg, 0.3kmol) regulate pH value to 5.35, add catalyzer 2.06kg polyethers F-6(: vinyl carbinol and oxyethane, epoxypropane polymer), complexing agent citric acid 0.15kg.Be warming up to 60-70 ℃ and pass into nitrogen protection, slowly drip epoxy chloropropane (470kg, 5.07kmol), now heat release is obvious.Drip 65-70 ℃ of insulation reaction of end temperature control and after 4 hours, be warming up to 80-90 ℃ of reaction 1 hour, reaction finishes to add pyridine (375kg, 4.74kmol).Be warming up to 100-110 ℃ of back flow reaction after 14 hours, add 18.75kg cleaner triethylamine.After dehydration and decolorization, use after salt acid for adjusting pH value to 3.5, add 5.88kg stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, react after 1 hour to filter obtain colourity and be less than 25#(platinum cobalt colorimetry) micro-yellow transparent clarified liq PPS-OH product.
Through HPLC analysing impurity and main peak content balance, be 0.71%, yield is 91.32%, and test piece effect is good.
Example 4
According to recipe configuration described in following table, for barrel plating nickel plating bath and additive, PPS-OH is 4.5-5.8 for the pH value of barrel plating nickel plating, Hull cell current intensity 2-4A/dm
2, bright current density range 2-4A/dm
2, temperature range 50-60 ℃, coating is bright, good without blackout phenomenon, ductility, resistance to abrasion without pit, low current density district in vain.
(PPS-OH wherein: pyridinium hydroxy propyl sulfobetaine, PME: propiolic alcohol oxyethyl group ether, PABS:N, N-PABS, PS: propargyl sodium sulfonate, PA: propargyl alcohol, BEO: butynediol ethoxy compound, POPDH: propiolic alcohol glyceryl ether, PN: sodium hydroxymethane sulfonate, UPS: isothiourea propanesulfonic acid inner salt, EHS: sodium isethionate, BBI: two phenyl ring imides, ALS: sodium allyl sulfonate, ATPN:S-propyloic isothiourea drone.）
Example 5
According to recipe configuration described in following table, for rack plating nickel plating bath and additive, PPS-OH is 4.5-5.8 for the pH value of rack plating nickel plating, Hull cell current intensity 2-4A/dm
2, bright current density range 2-4A/dm
2, temperature range 50-60 ℃, coating is bright, good without blackout phenomenon, ductility, resistance to abrasion without pit, low current density district in vain.
(wherein: PPS-OH: pyridinium hydroxy propyl sulfobetaine, PME: propiolic alcohol oxyethyl group ether, PABS:N, N-PABS, PS: propargyl sodium sulfonate, PA: propargyl alcohol, BEO: butynediol ethoxy compound, POPDH: propiolic alcohol glyceryl ether, EHS: sodium isethionate, BBI: two phenyl ring imides, ALS: sodium allyl sulfonate, ATPN:S-propyloic isothiourea drone.）
The above, be only the specific embodiment of the present invention, it should be pointed out that any those of ordinary skill in the art are in the disclosed technical scope of the present invention, and the variation that can expect easily or replacement, within all should being encompassed in protection scope of the present invention.
Claims (9)
1. a synthetic method for pyridinium hydroxy propyl sulfobetaine, its step comprises:
(1) intermediate 3-chlorine-2-hydroxyl propane sulfonate is synthetic
Under normal temperature condition, after hydrosulphite or pyrosulfite are fully dissolved in water, adding auxiliary sulphonating agent S-WAT regulation system pH value is between 5.2-5.5, after add catalyzer polyethers F-6; Add complexing agent, the condition that controls environment also adds epoxy chloropropane again, ring-opening reaction occurs and obtain 3-chlorine-2-hydroxyl propane sulfonate.
(2) pyridinium hydroxy propyl sulfobetaine is synthetic
In above-mentioned system, add again pyridine, after temperature control back flow reaction, add cleaner triethylamine, react 1 hour, dehydration and decolorization regulate pH value for 2-5, adds stablizer 4-hydroxyl-2 afterwards, 2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, obtain the aqueous solution of product pyridinium hydroxy propyl sulfobetaine.
2. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described catalyzer polyethers F-6 consumption is the 0.04-0.07% of system total amount quality.
3. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described stablizer 4-hydroxyl-2, and 2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, its consumption is 0.02% of system total amount.
4. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described complexing agent citric acid, its consumption is the 0.003-0.005% of pyrosulfite total mass.
5. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: during described epoxy chloropropane generation ring-opening reaction, in the hierarchy of control, temperature is 40-70 ℃, and passes into nitrogen as protection gas.
6. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, it is characterized in that: during described epoxy chloropropane generation ring-opening reaction, epoxy chloropropane slowly need to be splashed into, and its consumption and Sodium Pyrosulfite mol ratio are 1:0.51-0.52.
7. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described pyridine, the mol ratio of its consumption and epoxy chloropropane is 0.93:1.
8. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: after described system adds pyridine, be warming up to back flow reaction 10-14 hour between 95-110 ℃.
9. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described cleaner triethylamine, its addition is the 5-7.5% of pyridine total mass.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105198798A (en) * | 2015-11-03 | 2015-12-30 | 江苏梦得电镀化学品有限公司 | Production process of pyridinium hydroxy propyl sulfobetaine |
| CN105463520A (en) * | 2016-01-11 | 2016-04-06 | 湖北德美科技有限公司 | Barrel nickel plating softening agent and preparation method thereof |
| CN105463518A (en) * | 2016-01-11 | 2016-04-06 | 湖北德美科技有限公司 | Full bright nickel plating softening agent and preparation method thereof |
| CN105648480A (en) * | 2016-01-11 | 2016-06-08 | 湖北德美科技有限公司 | Full-bright nickel plating major brightening agent and preparing method thereof |
| CN106048668A (en) * | 2016-08-11 | 2016-10-26 | 太仓市凯福士机械有限公司 | Electroplating solution additive used for electroplating precise workpieces |
| CN106831544A (en) * | 2017-02-15 | 2017-06-13 | 中卫市创科知识产权投资有限公司 | A kind of PPS OH production technologies |
| CN109265392A (en) * | 2018-10-19 | 2019-01-25 | 湖北吉和昌化工科技有限公司 | A kind of method of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt |
| CN109371434A (en) * | 2018-11-26 | 2019-02-22 | 江门市德商科佐科技实业有限公司 | A kind of neutrality nickel plating solution and neutral nickel plating technology |
| CN111748830A (en) * | 2020-07-22 | 2020-10-09 | 六安市金安区宝德龙科技创新有限公司 | High-speed barrel nickel plating brightener and preparation method thereof |
| CN116253668A (en) * | 2023-05-12 | 2023-06-13 | 广州天赐高新材料股份有限公司 | Preparation method of sodium hydroxyalkyl sulfonate |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105198798A (en) * | 2015-11-03 | 2015-12-30 | 江苏梦得电镀化学品有限公司 | Production process of pyridinium hydroxy propyl sulfobetaine |
| CN105463520A (en) * | 2016-01-11 | 2016-04-06 | 湖北德美科技有限公司 | Barrel nickel plating softening agent and preparation method thereof |
| CN105463518A (en) * | 2016-01-11 | 2016-04-06 | 湖北德美科技有限公司 | Full bright nickel plating softening agent and preparation method thereof |
| CN105648480A (en) * | 2016-01-11 | 2016-06-08 | 湖北德美科技有限公司 | Full-bright nickel plating major brightening agent and preparing method thereof |
| CN106048668A (en) * | 2016-08-11 | 2016-10-26 | 太仓市凯福士机械有限公司 | Electroplating solution additive used for electroplating precise workpieces |
| CN106831544A (en) * | 2017-02-15 | 2017-06-13 | 中卫市创科知识产权投资有限公司 | A kind of PPS OH production technologies |
| CN109265392A (en) * | 2018-10-19 | 2019-01-25 | 湖北吉和昌化工科技有限公司 | A kind of method of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt |
| CN109265392B (en) * | 2018-10-19 | 2022-02-18 | 湖北吉和昌化工科技有限公司 | Method for continuously synthesizing pyridinium hydroxy propane sulfonate |
| CN109371434A (en) * | 2018-11-26 | 2019-02-22 | 江门市德商科佐科技实业有限公司 | A kind of neutrality nickel plating solution and neutral nickel plating technology |
| CN111748830A (en) * | 2020-07-22 | 2020-10-09 | 六安市金安区宝德龙科技创新有限公司 | High-speed barrel nickel plating brightener and preparation method thereof |
| CN116253668A (en) * | 2023-05-12 | 2023-06-13 | 广州天赐高新材料股份有限公司 | Preparation method of sodium hydroxyalkyl sulfonate |
| CN116253668B (en) * | 2023-05-12 | 2023-07-07 | 广州天赐高新材料股份有限公司 | Preparation method of sodium hydroxyalkyl sulfonate |
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