Uses, preparation and application of sodium p-styrenesulfonate_Industrial additives

Background and overview^[1][2]

White to slightly yellow crystalline powder. Relative molecular mass 206.19. Relative density 0.5 (25℃). Melting point 330℃ (decomposition). Insoluble in benzene, acetone, carbon tetrachloride, soluble in water (22.2 at 20°C), methanol (5.0 at 20°C), and dimethylformamide (8.5 at 20°C). This product has a vinyl group, and coupled with the induction effect of the para-position sulfonic acid group, it has strong reactivity and polymerization ability, so it can be used as a vinyl monomer with a sulfonic acid group. The oral LD ​​of male mice is ₅₀16000mg/kg.

Uses: Sodium p-styrene sulfonate is a widely used surfactant, used in the manufacture of acrylic fibers (DuPont process). The copolymer or copolymer mixture (copolymer and acrylic acid blend) of this product and acrylic acid can be used as a dyeing modifier to improve the dyeing performance of basic dyes; it can be used as a reactive emulsifier with good stability and water resistance. ; The polymer coordination compound formed by this product and polyvinyl benzyltrimethylammonium chloride can be used as artificial physiological membranes (such as artificial kidneys, contact lenses, etc.), industrial dialysis membranes, battery separators, rectifiers, etc.; Made of this product The water-soluble polymer made of this product can be used as a flocculant, dispersant for cosmetics, and hair styling agent; the homopolymer or copolymer of this product can be used as an antistatic agent for plastics, fibers, papers, etc.; This product can be made into ion exchange resin or ion exchange membrane; this product can also be used in photosensitive chemicals (to adjust the viscosity of gelatin), microcapsules, electrophotographic developers, electroplating bath additives (to improve gloss), medicine, etc.

Preparation^[2]

1> Add 281kg of β-chlorophenylene ethane into the 2000L glass-lined reactor, add 560L of dichloroethane under stirring, and then add 2.8kg of glacial acetic acid. Control the temperature at 20 to 90°C and keep it for 6 hours. Add 168kg of sulfur trioxide gas, control the temperature below 0°C, drop in 439L of deionized water, let it stand for 20 minutes to separate layers, fractionate and purify the lower dichloroethane for reuse, add the upper water layer to the concentration tank, and maintain a vacuum of 0.08 MPa or above, 292kg of water was concentrated to obtain 585.6kg of p-sulfonic acid-β-chlorophenylethane aqueous solution, in which the content of p-sulfonic acid-β-chlorophenylethane was 75%. Transfer the p-sulfonic acid-β-chlorophenyl ethane solution into a glass-lined high-level jar, and add 200 mL of 40% diethylhydroxylamine aqueous solution.

2> Add 50% NaOH solution kg to the neutralization kettle, add 171kg of deionized water while stirring, dilute to 35% concentration, stir and heat to 110°C, in a slightly boiling state, quickly add the above dropwise within one hour After adding the prepared p-sulfonic acid-β-chlorophenyl ethane, stir for another 5 minutes, turn on the circulating water to cool down to 40°C, turn off the circulating water, and separate with a high-speed centrifuge. During centrifugation, wash with acetic acid solution until the pH value of the filter cake drops to 8-11, and spin dry for 30 minutes.

3> Take the product obtained in step 2> and crush it. Use a granulator to crush the product into 20-30 mesh size. Spread it on a breathable canvas and place it in a drying room. Control the temperature at 40-50°C. The relative humidity is above 50%, dry for 1 to 4 hours, take samples every half hour, analyze and measure the moisture content of 8 to 12%, take the material and bag it, and obtain 364kg of sodium p-styrene sulfonate white powder, with a yield of 80%, take samples and analyze The dry basis content is 93%, the moisture content is 10%, and the pH value is 8.5.

4> Place the primary mother liquor after centrifugation in step 2> into a concentration tank, add 117kg of hydrochloric acid, adjust the pH to 7, add 0.1kg of polymerization inhibitor, concentrate under reduced pressure to produce 250kg of water, let it stand, and remove the lower salt layer and water into a climbing dryer, concentrated to dryness, 282.5kg of salt was produced, with a content of 98%. The upper material was cooled to 40°C and centrifuged to separate, to obtain 68kg of sodium p-styrenesulfonate recycled product, with a yield of 15%, which is the same as step 3 〉The obtained products were combined, and the yield was 95%.

Apply^[3-5]

A method for making cross-linked polypara-styrene sodium sulfonate gel microspheres, using reverse-phase suspension polymerization, using toluene as the dispersion medium and ethylcellulose as the dispersant to form an oil phase; using p-styrene sulfonate Sodium sulfate (SSS) is the functional monomer, N,N’-methylene bisacrylamide is the cross-linking agent, ammonium persulfate is the initiator, and distilled water forms the aqueous phase to prepare a cross-linking particle size of about 150~250um Polysodium parastyrene sulfonate gel microspheres (CPSSS). It has good swelling properties and carries a large amount of negative charges on its surface and inside. It can be used in the fields of sustained and controlled release of drugs, removal of cations in sewage, separation and extraction of cationic natural products, etc.

A method for preparing trypsin molecular surface imprinted microspheres using sodium p-styrene sulfonate as a functional monomer, using glutaraldehyde as a cross-linking agent to prepare cross-linked polyvinyl alcohol microspheres, and using methyl The esterification reaction between acryloyl chloride and the hydroxyl groups on the surface of the microspheres makes the surface of the cross-linked polyvinyl alcohol microspheres contain a large number of polymerizable double bonds. In the buffer solution, sodium p-styrene sulfonate and template trypsin automatically form a host-guest complex. The free radicals generated by the ammonium persulfate/sodium bisulfite initiating system are used to cause the monomer sodium p-styrenesulfonate surrounding trypsin and the cross-linking agent N,N’-methylenebisacrylamide to react in microorganisms. A grafting cross-linking polymerization reaction occurred on the surface of the sphere, and trypsin surface-imprinted microspheres were produced. The molecular surface-imprinted microspheres have excellent binding affinity and specific recognition selectivity for trypsin. They are useful for extracting trypsin using molecular surface imprinting technology. Protease has positive reference value.

CN201510203532.It is characterized in that: sodium p-styrenesulfonate monomer or/and 2-methacrylamide glucopyranose monomer is added to a mixed solvent according to a certain proportion, and the mixed solvent is water and nitrogen-nitrogen dimethylformamide ( A mixture of N,N-Dimethylformamide) was polymerized using the reversible addition-fragmentation chain transfer polymerization (RAFT) method to obtain several sodium p-styrenesulfonate monomers or/and 2-methacrylamide pyran in different proportions. A polymer of glucose monomers. RAFT synthesis technology is used to utilize sulfonic acid group-containing monomers and sugar-containing monomers, and adjust the polymer structure by controlling their relative proportions to obtain a polymer substance that can promote the proliferation of embryonic stem cells in vitro and induce efficient directional neural differentiation.

Main reference materials

[1] Practical Fine Chemical Dictionary

[2] [Chinese invention] CN201711209024.8 A preparation method of sodium p-styrenesulfonate

[3] CN201610381707.0 A method for making cross-linked polypara-styrene sodium sulfonate gel microspheres

[4] CN201610101981.8 A method for preparing trypsin-imprinted microspheres using sodium p-styrenesulfonate as the monomer

[5] CN201510203532.X Glycosaminoglycan analogs and their synthesis methods and their application in in vitro embryonic stem cell proliferation and directed neural differentiation