WO2017128860A1 - Composé carboxamide ou amine, procédé de préparation et application de ce dernier - Google Patents

Composé carboxamide ou amine, procédé de préparation et application de ce dernier Download PDF

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WO2017128860A1
WO2017128860A1 PCT/CN2016/108500 CN2016108500W WO2017128860A1 WO 2017128860 A1 WO2017128860 A1 WO 2017128860A1 CN 2016108500 W CN2016108500 W CN 2016108500W WO 2017128860 A1 WO2017128860 A1 WO 2017128860A1
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reaction
added
carboxamide
flask
amine compound
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Chinese (zh)
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毛丽娟
刘树柏
王松平
张再先
万定飞
彭传扬
丁轶凡
孙兴
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毛丽娟
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/16—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of hydrogen sulfide or its salts to unsaturated compounds
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
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    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/48—Two nitrogen atoms
    • C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
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    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
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    • C08K5/3492—Triazines
    • C08K5/34922—Melamine; Derivatives thereof
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    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
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    • C08K5/37—Thiols
    • C08K5/372—Sulfides, e.g. R-(S)x-R'
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    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/378—Thiols containing heterocyclic rings

Definitions

  • the invention belongs to the technical field of invention and preparation of novel antioxidant stabilizer compounds, in particular to a carboxamide or amine compound, a preparation method thereof and application thereof as an antioxidant stabilizer for a novel polymer material.
  • antioxidant stabilizers The sales market for antioxidant stabilizers is very large worldwide, and a single plastic antioxidant consumes about 420,000 tons worldwide in 2011.
  • Asia Pacific has the largest consumption, followed by Europe and North America. It is estimated that the sales of anti-oxidant stabilizers for materials in the Asia-Pacific region will reach US$4.8 billion in 2016.
  • the demand for and production of anti-oxidant stabilizers for materials has been transferred from the United States, Western Europe and Japan to emerging markets in Asia; in particular, China and India. At present, the consumption of antioxidants in China has increased rapidly.
  • a few large international suppliers still control the world market price of materials antioxidant stabilizers.
  • the market for antioxidant stabilizing additives, especially the heat stabilizer market, is growing fast in Asia Pacific. Special antioxidant stabilizers have grown with the growth of polymer materials applications and technology development.
  • antioxidant stabilizing additives are also widely used in the plastics industry, particularly in the field of olefinic polymers, chlorinated high polymers (PVC).
  • PVC products are mainly used in the construction sector, especially for the manufacture of pipes and cables. More than 85% of antioxidant additives are used in this industry.
  • Demand in the Asia Pacific region is expected to grow further. Light antioxidant additives will grow even faster. In particular, the increase in polypropylene and polyethylene products will be even more impressive.
  • the antioxidant stabilizer has migration in the material, is easy to extract, is easy to be hydrolyzed, and has weak resistance. Acid solution, anti-alkali, anti-hydrolysis, anti-pollution, environmental degradation, resulting in poor protection of material quality and performance, shortened material life, and limited application of materials.
  • the object of the invention is to provide a low volatility, good compatibility with polymer materials, strong polymer protection ability, long service life of materials, good environmental protection, strong anti-oxidation ability and strong acid, alkali and strong chemical pollution environment.
  • a stable carboxamide or amine compound is used as an antioxidant stabilizer, a preparation method thereof, and an application as a novel polymer material antioxidant stabilizer.
  • the present invention adopts the following technical scheme: a carboxamide or an amine compound characterized by having the following structure:
  • X is CH 2, SO, NH or NR,
  • n is a positive integer
  • n is a positive integer
  • n is a positive integer
  • n is a positive integer
  • X is S, O, NH or NR 1 ,
  • Y is X, S, O, NH, NR 1 ,
  • R is Me, or
  • n is a positive integer greater than or equal to 5;
  • X is S, O, NH or NR 1 ,
  • n is a positive integer
  • n is a positive integer
  • n is a positive integer.
  • the carboxamide or amine compound is preferably:
  • the invention also provides a preparation method of a carboxamide or an amine compound, comprising the following steps:
  • Methyl carboxylate or dimethyl carboxylic acid is dissolved in 90-120 ° C petroleum ether or methanol or ethanol or acetonitrile or N, N-dimethylformamide solvent to add 10-3% p-toluenesulfonic acid or hydrochloric acid or A carboxylic acid or dilute sulfuric acid or Lewis acid is used as a catalyst, and 4-amino-2,2,6,6-tetramethylpiperidine is added. The mixture was heated to reflux and the reaction was followed until the conversion of the carboxylic acid ester was complete.
  • the cyanuric chloride is dissolved in anhydrous acetone or petroleum ether or acetonitrile or ethanol or dichloromethane. The temperature is raised to 35-75 degrees under the protection of nitrogen, an equivalent amount of inorganic or organic base is added, and then cyanuric chloride is added dropwise. Molar R-(CH 2 )-YH, the reaction is maintained at this temperature for 3-15 hours, TLC tracks the progress of the reaction until the R-(CH 2 )-YH starting material disappears; 2,6-di-tert-butyl group is added to the reaction system -4-OH-benzylamine or thiol or alcohol, the reaction mixture is continued to stir at its temperature overnight. The TLC tracks the progress of the reaction until it is completely converted to the trisubstituted reaction product.
  • Methyl acrylate is dissolved in petroleum ether or dichloromethane or tetrahydrofuran or methyl butyl ether or acetone or ethyl acetate, adding dodecyl thiol and N,N-dimethylamino-4-pyridine or triethylamine, mixture at room temperature Stir for 5 hours at 40 degrees Celsius overnight.
  • the TLC tracks the progress of the reaction until the reaction is complete.
  • Aqueous hydrochloric acid solution was added, ethyl acetate was added, the organic base was washed away, and the organic phase was washed with water. The organic phase is dried, filtered, and the organic solvent is evaporated in vacuo.
  • the high-pressure reaction flask was used to weigh the crude product of methyl acrylate and dodecyl mercaptan and N-methylformamide. Under the protective condition of N 2 , an appropriate amount of sodium metal was weighed into the flask, and then dried methanol was added. The reaction was carried out, and nitrogen gas was protected. After all the sodium metal was completely reacted, the reaction liquid was completely transferred to a high pressure reaction bottle. Under the N 2 protection condition, diethyltriamine was added to the high pressure reaction flask, and the reaction was carried out in an external temperature oil bath at 80 ° C for a reaction time of 15-30 hours. After completion of the reaction, recrystallization from ethyl acetate or methylene chloride or methyl t-butyl ether afforded product as a white solid.
  • the solid is removed by suction filtration, and then an appropriate amount of dichloromethane is added to the filtrate to extract the product into a dichloromethane phase for separation.
  • the dichloromethane phase is separated, dried, and the solvent is removed under vacuum to obtain colorless. Or a light yellow liquid for use.
  • reaction flask An appropriate amount of octadecylamine is added to the reaction flask, followed by addition of high boiling petroleum ether (90-120 degrees Celsius) or toluene or ethanol, p-toluenesulfonic acid or hydrochloric acid or glacial acetic acid or hydrochloric acid and the resulting solution.
  • high boiling petroleum ether 90-120 degrees Celsius
  • toluene or ethanol p-toluenesulfonic acid or hydrochloric acid or glacial acetic acid or hydrochloric acid
  • the mixture was placed in a constant temperature oil bath for stirring reaction, and the temperature was set to 125 ° C, and nitrogen gas was added to the condensate separator. (Reaction time completion time is 36-48 hours. When the reaction is completed, the liquid in the flask cooled to room temperature becomes solid.
  • the appropriate amount of methanol is added to the reaction flask under stirring, and then suction filtration is carried out to wash with
  • 3-thiohexadecylamine and the above product are added to a 50 ml reaction flask, then high-boiling petroleum ether (90-120 ° C) or toluene or ethanol and p-toluenesulfonic acid or hydrochloric acid or glacial acetic acid or hydrochloric acid, protected by nitrogen
  • high-boiling petroleum ether 90-120 ° C
  • toluene or ethanol and p-toluenesulfonic acid or hydrochloric acid or glacial acetic acid or hydrochloric acid protected by nitrogen
  • the reaction was stirred for 36-48 hours in a 120-degree constant temperature oil bath.
  • the progress of the reaction was checked by TLC. When the reaction was cooled to room temperature, the liquid in the flask became solid.
  • An appropriate amount of methanol was added to the reaction flask under stirring, followed by suction filtration, washing with methanol for 2-4 times, drying, and heating under
  • the reaction equation of the preparation method is:
  • carboxamide or amine compound in building materials, organic electronics, plastics, rubber, paints, petroleum products, coatings or fibers.
  • the stable molecular weight of the antioxidant is more stable by the linkage of a stable carboxamide or an amine bond, and thus the protective property of the polymer material is stronger and longer, and the hindered phenolic antibiotic is resistant.
  • Oxidation stabilizers are more resistant to hydrolysis, resistance to acid hydrolysis, resistance to alkaline hydrolysis, and resistance to chemically contaminated environments than products corresponding to most esters on the international market. Adjusting the n value of CH2 in Formula 1 can produce an antioxidant with a different length of fat to produce a sterically hindered phenol antioxidant stabilizer that matches the properties of a particular polymer; changing the value of n in Equation 2 can result in a high steric hindrance.
  • An anti-oxidant stabilizer with a phenolic density which has a hindered phenol density equivalent to or higher than Irganox 1010 hindered phenol antioxidant stabilizer.
  • the product light stabilizer 770 and the light stabilizer 3853 are all free radical oxidation processes caused by photoinitiation of stable polymer materials widely used in polymer materials on the market, 770 and 3853
  • the linking fragments which increase the molecular weight adjustment and the polymer matching in the structure are all carboxylate esters, and the chemical stability and resistance to hydrolysis, acid hydrolysis, alkali hydrolysis and chemical degradation of the carboxylate are weak.
  • Formula 5 is linked to the broad molecule by a linkage of a UV-absorbing functional triazine core and a hindered phenol thermostable functional group.
  • the main antioxidant and the auxiliary antioxidant are naturally entangled into a new primary and secondary synergistic antioxidant stabilizer, and they contain a combination of hindered phenol and thioether.
  • the triazine core structure is known to be a broad UV light absorption core structure with a wide range of UV absorption (see http://webbook.nist.gov/chemistry), compared to benzophenone and benzotriazoles. Good absorption effect. Ultraviolet absorption of the parent nucleus triazine occurs in the same high molecular weight antioxidant stabilizer molecule.
  • the multifunctional synergistic anti-oxidation stabilizer can adjust the side chain of the structure to achieve the matching property with the polymer material, can effectively prevent the appearance of the image, and can fully exert the protection effect on the polymer material.
  • stable linkage of amide and amine bonds can effectively improve the stability of these hybrid synergistic functional molecules, resist hydrolysis, acid hydrolysis, alkali hydrolysis, and resistance to chemical pollution.
  • the stable carboxamide-bonded thioether high-temperature antioxidant stabilizers of formula 6, formula 7 and formula 8 overcome the disadvantages of the corresponding carboxylate-bonded products (DSTDP, DSTLP, etc.) which are easily degraded, and the product has no odor, and the environment Easy to use for protection and operation.
  • the above two types of thioether antioxidant molecules which are stably linked are more stable and have better resistance to hydrolysis, acid hydrolysis, alkali hydrolysis and environmental pollution degradation. Therefore, they can meet the anti-aging protection needs of a wider range of materials.
  • the compounds of the invention all have stable carboxamide or amine bond to form an anti-oxidation stabilizer with different stable structures, and at the same time, by adjusting the value of n to produce different lengths of the fat chain, so that the properties of the specific polymer materials are perfectly matched and solved.
  • the small molecule stabilizer has the problems of rapid evaporation and easy extraction in the polymer material, greatly prolonging the service life of the material, and embodies the stronger and longer lasting protection properties of the polymer material of the invention.
  • the stable polymer antioxidant of the invention has stronger ability to resist hydrolysis, resist acid hydrolysis, resist alkali hydrolysis and resist chemical pollution to the environment than the prior art, and these characteristics are present. The development of new materials provides a new and better range of antioxidants.
  • such carboxamides or amine compounds are also non-volatile, have good matching properties with polymer materials, strong polymer protection ability, good environmental performance, beautiful and durable, and low cost.
  • Methyl stearate (5 g, 16.75 mmol) is dissolved in (50 ml) solvent, which may be petroleum ether or toluene or ethanol or methanol or acetonitrile or dimethylformamide.
  • solvent which may be petroleum ether or toluene or ethanol or methanol or acetonitrile or dimethylformamide.
  • 4-Amino-2,2,6,6-tetramethylpiperidine (3.14 g, 20.10 mmol) and 5% (W/W) catalyst acid p-toluenesulfonic acid or carboxylic acid or hydrochloric acid were added under stirring with nitrogen. Or dilute sulfuric acid or Lewis acid. The mixture was heated to reflux until the reaction was complete. The solvent was removed in vacuo and the crude material was crystallised from ethyl acetate and petroleum ether (1:3) to give product (II) 6.58 g.
  • Cyanuric chloride (5 g, 27.11 mmol) is dissolved in anhydrous acetone or acetonitrile or tetrahydrofuran or ethanol or methanol (30 ml), and 28.47 mmol of sodium carbonate or potassium carbonate or triethylamine or diiso is added under nitrogen. Propylethylamine, then 2,6-di-tert-butyl-4-hydroxyindolethiol (6.84 g, 27.11) was added dropwise in 20 ml of anhydrous acetone or acetonitrile or tetrahydrofuran or ethanol or methanol at 50 °C. Millimoles). The reaction mixture was stirred at 50 ° C for 5 hours, and heated to 65 ° C for 3 hours;
  • Methyl acrylate (3 g, 34.85 mmol) is dissolved in 10-25 ml of petroleum ether or dichloromethane or tetrahydrofuran or methyl butyl ether or acetone or ethyl acetate, and dodecyl mercaptan (g, 34.85 mmol) And 2-10% N,N-dimethylamino-4-pyridine or triethylamine, the mixture was stirred at room temperature for 5 hours, 40 ° C overnight. The TLC tracks the progress of the reaction until the reaction is complete.
  • the bottom of the flask was solid precipitated, and the ice water bath was stirred under nitrogen to carry out a stirring reaction.
  • the reaction time was about 6-18. Hours, TLC tracks the response until it is complete.
  • the solid is removed by suction filtration, and then an appropriate amount of dichloromethane is added to the filtrate to extract the product into a dichloromethane phase for separation.
  • the dichloromethane phase is separated, dried, and the solvent is removed under vacuum to obtain colorless. Or a light yellow liquid is the product, the yield is 79-95%.

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  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un composé carboxamide ou amine, le procédé de préparation de ce dernier et l'application de ce dernier comme stabilisant antioxydant stable et efficace, et concerne le domaine technique des nouveaux stabilisants antioxydants. Le composé selon l'invention présente une liaison carboxamide ou amine stable de manière à former un stabilisant antioxydant présentant différentes structures de stabilisation. En outre, un produit présentant une chaîne aliphatique dotée de longueurs différentes peut être généré par l'ajustement d'une valeur n de manière à donner au produit une meilleure compatibilité avec une propriété d'un matériau macromoléculaire spécifique, traitant les problèmes d'un stabilisant à petite molécule d'évaporation trop rapide et de faible résistance à la lixiviation dans le matériau macromoléculaire. L'invention étend considérablement la durée de vie du matériau et permet d'obtenir une protection plus forte et plus durable destinée au matériau macromoléculaire. Par rapport à la technique, un antioxydant stable destiné à une macromolécule selon l'invention présente une meilleure résistance à l'hydrolyse, l'hydrolyse acide, l'hydrolyse alcaline, la contamination chimique et la dégradation environnementale. Ces caractéristiques offrent un nouveau choix amélioré d'un antioxydant destiné à la mise au point d'un nouveau matériau moderne. En outre, le composé carboxamide ou amine présente les caractéristiques d'une faible volatilité, d'une bonne compatibilité avec le matériau macromoléculaire, offre une forte protection au matériau macromoléculaire et le respect de l'environnement, fournit un aspect et une durabilité attrayants, possède un faible coût, et analogue.
PCT/CN2016/108500 2016-01-26 2016-12-05 Composé carboxamide ou amine, procédé de préparation et application de ce dernier WO2017128860A1 (fr)

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EP4001265A1 (fr) * 2020-11-11 2022-05-25 Shaoxing Ruikang Biotechnologies Co., Inc Structure de stabilisateur de lumière de base faible d'entrave stérique, son procédé de préparation et son application
CN114797513A (zh) * 2022-04-11 2022-07-29 云南磷化集团有限公司 一种实验室试剂瓶标签保护膜的制备方法
CN116253905A (zh) * 2023-02-18 2023-06-13 四川大学 一种稳定、智能的抗感染水凝胶及其制备方法和应用
CN116813917A (zh) * 2022-10-31 2023-09-29 张燕 一种超低温环氧密封胶用固化剂及其制备的密封胶
CN117185927A (zh) * 2023-08-01 2023-12-08 广东仁康达材料科技有限公司 一种二异丁烯合成异壬酸甲酯的方法
CN118005351A (zh) * 2024-02-02 2024-05-10 义乌中国小商品城房地产开发有限公司 一种泡沫混凝土及其制备工艺

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CN107056661A (zh) * 2017-04-18 2017-08-18 山东铂源药业有限公司 一种拉帕替尼中间体2‑(甲砜基)乙胺盐酸盐的制备方法
CN112210228B (zh) * 2020-10-23 2023-01-24 浙江亿得新材料股份有限公司 一种高牢度、高溶解性的红色染料制备工艺
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CN110642722A (zh) * 2019-10-18 2020-01-03 山东省化工研究院 一种制备n,n-四甲基癸二胺的方法
EP4001265A1 (fr) * 2020-11-11 2022-05-25 Shaoxing Ruikang Biotechnologies Co., Inc Structure de stabilisateur de lumière de base faible d'entrave stérique, son procédé de préparation et son application
CN114797513A (zh) * 2022-04-11 2022-07-29 云南磷化集团有限公司 一种实验室试剂瓶标签保护膜的制备方法
CN116813917A (zh) * 2022-10-31 2023-09-29 张燕 一种超低温环氧密封胶用固化剂及其制备的密封胶
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CN118005351A (zh) * 2024-02-02 2024-05-10 义乌中国小商品城房地产开发有限公司 一种泡沫混凝土及其制备工艺

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