WO2016101800A1 - Composition d'additif pour polymère, procédé pour sa préparation, et matériau de moulage de polymère thermoplastique ignifugeant constitué de celle-ci - Google Patents

Composition d'additif pour polymère, procédé pour sa préparation, et matériau de moulage de polymère thermoplastique ignifugeant constitué de celle-ci Download PDF

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WO2016101800A1
WO2016101800A1 PCT/CN2015/097211 CN2015097211W WO2016101800A1 WO 2016101800 A1 WO2016101800 A1 WO 2016101800A1 CN 2015097211 W CN2015097211 W CN 2015097211W WO 2016101800 A1 WO2016101800 A1 WO 2016101800A1
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salt
chlorine
polymer
weight
acid
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PCT/CN2015/097211
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Chinese (zh)
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李岩
柴生勇
李积德
卢昌利
孔蕾
陈林
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肖群
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    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/16—Halogen-containing compounds
    • 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
    • C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
    • C08K13/02—Organic and inorganic ingredients
    • 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
    • C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
    • C08K13/04—Ingredients characterised by their shape and organic or inorganic ingredients
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/14—Glass
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to an additive composition for a polymer, and in particular to a dialkyl phosphinate containing a chlorine element and an alkylphosphinate and/or a phosphite, and a process for the preparation thereof and a process for the same Flame retardant thermoplastic polymer molding material.
  • Dialkyl phosphinates are widely used as flame retardants and are known to be synthesized by various methods.
  • the use of a metal salt of a disubstituted phosphinic acid in the use of a polyester as a flame retardant is disclosed in the patent DE 44 093 032.
  • a process for the preparation of a metal salt of a disubstituted phosphinic acid is disclosed in the publications DE 199 092 022 and US Pat.
  • 6,359,171 B1 discloses a process for preparing aluminum dialkylphosphinate, which firstly synthesizes a monoalkylphosphinic acid ester using yellow phosphorus, and then reacts with an aluminum salt after hydrolysis to obtain an acid by radical polymerization.
  • Aluminum dialkyl phosphinate flame retardant discloses a process for preparing aluminum dialkylphosphinate, which firstly synthesizes a monoalkylphosphinic acid ester using yellow phosphorus, and then reacts with an aluminum salt after hydrolysis to obtain an acid by radical polymerization.
  • Aluminum dialkyl phosphinate flame retardant is a process for preparing aluminum dialkylphosphinate, which firstly synthesizes a monoalkylphosphinic acid ester using yellow phosphorus, and then reacts with an aluminum salt after hydrolysis to obtain an acid by radical polymerization.
  • Aluminum dialkyl phosphinate flame retardant discloses a process for preparing aluminum dialkylpho
  • Aluminum diethylphosphinate is a new halogen-free flame retardant with high heat stability and excellent flame retardancy.
  • the flame-retardant polymer molding composition to which aluminum diethylphosphinate is added causes particularly severe corrosion to the screw of the compounding device during processing, and the surrounding polymer Damage is caused, in particular, to degradation of the polymer.
  • the main reason is that the dialkylphosphinic acid ionized by aluminum dialkylphosphinate is selectively complexed with metal ions, especially for nickel, chromium and the like of stainless steel clocks. This causes severe corrosion of the screw in the processing of the flame retardant polymer in the dialkyl phosphinate.
  • the flame retardant polymer molding composition of the phosphinate has corrosion of the compounding device screw during processing, and flame retardant polymerization of the flame retardant polymer molding composition to which the dialkylphosphinate is added.
  • the color yellowing of the object can be significantly improved, and the whiteness of the part is better.
  • the alkyl phosphinate contains an additive composition of a chlorine element and an alkylphosphinate and/or a phosphite structure, and a flame-retardant thermoplastic polymer molding material composed of the same.
  • the additive is applied to a polymer, and the degree of corrosion of the screw of the compounding device is small during the processing, and the degree of damage to the surrounding polymer is small, and the obtained flame-retardant polymer molding composition has better whiteness and flame retardancy.
  • the other properties of the polymer have almost no effect.
  • Another object of the present invention is to provide a process for preparing the above-mentioned additive composition for a polymer which is simple in process flow, short in reaction cycle, and high in overall yield.
  • An additive composition for a polymer comprising:
  • Component A 80% by weight to 99.99% by weight of a dialkylphosphinate having the structure represented by the formula (I),
  • R1 and R2 are the same or different and are represented by H, C1-C6 alkyl or C6-C18 aryl;
  • M is Mg, Ca, Al, Zn, Fe
  • n 2 to 4.
  • Component B 0.001 wt% - 0.5 wt% chloride, the chlorine content in the total additive is 60-800 ppm;
  • Component C 0% by weight to 20% by weight of an alkylphosphinate having the structure represented by the formula (II),
  • R3 is represented by ethyl, propyl and/or butyl; M is Mg, Ca, Al, Zn, Fe; m is from 1 to 4;
  • Component D 0 wt% to 0.9 wt% of a phosphite having a structure represented by the formula (III);
  • R4 is represented by H; M is Mg, Ca, Al, Zn, Fe; m is from 1 to 4;
  • Component C, D are not 0 wt% at the same time, and the sum of the components A, B, C and D is always 100 wt%.
  • R1, R2 are represented by ethyl, propyl and/or butyl.
  • the chlorine element is present in the total additive in an amount of from 70 to 450 ppm, preferably from 70 to 200 ppm by weight.
  • the chloride is selected from the group consisting of chlorinated olefins, sodium chloride, potassium chloride, aluminum chloride, chlorine, hydrochloric acid, sodium hypochlorite, chlorine-containing coupling agents, chlorine-containing flame retardants, chlorine-containing surfactants or PVC. Species or several
  • the chloride may also be selected from the group consisting of 1-chloroethylethylphosphinate, 1-chloroethylphosphinate, 1,2-dichloroethylethylphosphinate, 1,2- Dichloroethylphosphinate, 3-chloropropylpropylphosphinate, 3-chloropropylphosphinate, 4-chlorobutylethylphosphinate, 4-chlorobutylbutyl One of a phosphinate, a 4-chlorobutylphosphinate, a chlorocyclohexylethylphosphinate, a chlorocyclohexylcyclohexylphosphinate, or a chlorocyclohexylphosphinate
  • the salt is a sodium salt, a potassium salt, a magnesium salt, a calcium salt, an aluminum salt, a barium salt, a zinc salt or an iron salt.
  • the polymer is PBT, nylon, PPE, TPE, TPU or epoxy, preferably PBT, nylon or PPE.
  • a method for preparing an additive composition for a polymer according to the present invention is as follows:
  • a dialkyl phosphinate containing a chloride can be prepared by an aqueous solution reaction
  • step d mixing the products obtained in step a and step b and/or step c;
  • hypophosphite is sodium hypophosphite or potassium hypophosphite
  • phosphite is sodium phosphite or potassium phosphite
  • the metal compound is a metal compound of Mg, Ca, Al, Zn, Fe;
  • the chlorinated olefin is one or more of 1-chloroethylene, 1,2-dichloroethylene, 3-chloropropene, 4-chlorobutene or chlorocyclohexene.
  • dialkylphosphinic acid or a salt solution thereof is reacted with a metal compound solution to obtain a dialkyl hypophosphite, which is then miscible with the aqueous solution of the additive I to obtain a chloride-containing dialkylphosphinate, and then Obtained with a solution of an alkylphosphinic acid or a salt thereof and/or a phosphorous acid or a salt thereof;
  • the additive I is one or more of NaCl, KCl, AlCl 3 , chlorine, hydrochloric acid, sodium hypochlorite, a chlorine-containing coupling agent or a chlorine-containing surfactant;
  • the additive I may also be selected from 1-chloroethylethylphosphinate, 1-chloroethylphosphinate, 1,2-dichloroethylethylphosphinate, 1,2- Dichloroethylphosphinate, 3-chloropropylpropylphosphinate, 3-chloropropylphosphinate, 4-chlorobutylethylphosphinate, 4-chlorobutylbutyl One of a phosphinate, a 4-chlorobutylphosphinate, a chlorocyclohexylethylphosphinate, a chlorocyclohexylcyclohexylphosphinate, or a chlorocyclohexylphosphinate
  • the salt is a sodium salt, a potassium salt, a magnesium salt, a calcium salt, an aluminum salt, a barium salt, a zinc salt or an iron salt.
  • the metal compound is a metal compound of Mg, Ca, Al, Zn, or Fe.
  • the dialkylphosphinate is sodium dialkyl phosphinate or potassium dialkyl phosphinate; the phosphite is sodium phosphite or potassium phosphite.
  • dialkylphosphinic acid or a salt solution thereof is reacted with a metal compound solution to obtain a dialkyl hypophosphite, which is then miscible with the alkylphosphinic acid or a salt solution thereof and/or a phosphorous acid or a salt thereof, and finally Adding additive II during product filtration or washing or drying;
  • the additive II is one or more of NaCl, KCl, AlCl 3 , a chlorine-containing flame retardant, a chlorine-containing coupling agent, a chlorine-containing surfactant or PVC.
  • the additive II may also be selected from the group consisting of 1-chloroethylethylphosphinate, 1-chloroethylphosphinate, 1,2-dichloroethylethylphosphinate, 1,2- Dichloroethylphosphinate, 3-chloropropylpropylphosphinate, 3-chloropropylphosphinate, 4-chlorobutylethylphosphinate, 4-chlorobutylbutyl a phosphinate, 4-chlorobutylphosphinate, chlorocyclohexylethylphosphinate, One or more of chlorocyclohexylcyclohexylphosphinate, chlorocyclohexylphosphinate, sodium salt, potassium salt, magnesium salt, calcium salt, aluminum salt, barium salt, zinc Salt, iron salt.
  • a raw material for preparing a dialkyl hypophosphite containing chlorine element to a solvent, and reacting with an olefin under the action of an initiator and a reaction assistant to obtain a chloride-containing dialkylphosphinic acid or a salt solution thereof, and a solution thereof
  • the aqueous solution of the metal compound can be prepared by preparing a dialkyl phosphinate containing a chloride, and then being miscible with a solution of the alkylphosphinic acid or a salt thereof and/or a phosphorous acid or a salt thereof.
  • the solvent is water;
  • the initiator is an azo initiator, an organic peroxide initiator or an inorganic peroxide initiator;
  • the olefin is one or both of ethylene and/or butene a mixture;
  • the reaction aid is sodium borohydride or potassium borohydride.
  • the present invention discloses the use of an additive composition for a polymer as described above as a flame retardant.
  • the present invention also discloses a flame-retardant thermoplastic polymer molding material comprising the above additive composition, comprising 5-20 parts by weight of an additive for a polymer, 50-70 parts by weight of a polymer or a mixture thereof;
  • Additives for polymers include:
  • Component A 80% by weight to 99.99% by weight of a dialkylphosphinate having the structure represented by the formula (I),
  • R1 and R2 are the same or different and are represented by H, C1-C6 alkyl or C6-C18 aryl;
  • M is Mg, Ca, Al, Zn, Fe
  • n 2 to 4.
  • Component B 0.001 wt% - 0.5 wt% chloride, the chlorine content in the total additive is 60-800 ppm;
  • Component C 0% by weight to 20% by weight of an alkylphosphinate having the structure represented by the formula (II),
  • R3 is represented by ethyl, propyl and/or butyl; M is Mg, Ca, Al, Zn, Fe; m is from 1 to 4;
  • Component D 0 wt% to 0.9 wt% of a phosphite having a structure represented by the formula (III);
  • R4 is represented by H; M is Mg, Ca, Al, Zn, Fe; m is from 1 to 4;
  • Component C, D are not 0 wt% at the same time, and the sum of the components A, B, C and D is always 100 wt%.
  • R1, R2 are represented by ethyl, propyl and/or butyl.
  • the chlorine element is present in the total additive in an amount of from 70 to 450 ppm, preferably from 70 to 200 ppm by weight.
  • the chloride is selected from the group consisting of chlorinated olefins, sodium chloride, potassium chloride, aluminum chloride, chlorine, hydrochloric acid, sodium hypochlorite, chlorine-containing coupling agents, chlorine-containing flame retardants, chlorine-containing surfactants or PVC. Species or several
  • the chloride may also be selected from the group consisting of 1-chloroethylethylphosphinate, 1-chloroethylphosphinate, 1,2-dichloroethylethylphosphinate, 1,2- Dichloroethylphosphinate, 3-chloropropylpropylphosphinate, 3-chloropropylphosphinate, 4-chlorobutylethylphosphinate, 4-chlorobutylbutyl One of a phosphinate, a 4-chlorobutylphosphinate, a chlorocyclohexylethylphosphinate, a chlorocyclohexylcyclohexylphosphinate, or a chlorocyclohexylphosphinate
  • the salt is a sodium salt, a potassium salt, a magnesium salt, a calcium salt, an aluminum salt, a barium salt, a zinc salt or an iron salt.
  • the polymer is PBT, nylon, PPE, TPE, TPU or epoxy resin, preferably PBT, nylon or PPE.
  • the flame-retardant thermoplastic polymer molding material of the present invention further comprises 15 to 30 parts by weight of glass fibers and 1 to 5 parts by weight of other auxiliary agents.
  • the invention has the following beneficial effects:
  • a dialkyl phosphinate containing a chlorine element and an alkylphosphinate and/or a phosphite structure prepared by the present invention as an additive of a flame retardant polymer, the additive is applied to a polymer, During the processing, the flame retardant polymer of the dialkyl phosphinate as an additive is greatly reduced to the degree of screw corrosion of the compounding device, the processing cost of the device is reduced, and the frequent replacement of the screw during the processing is also reduced. Energy and labor loss, and the whiteness of the polymer obtained by extrusion is superior to the conventional dialkyl phosphinate modified polymer parts, which greatly broadens the application range of the plastic additive in the market;
  • component A+B can be prepared, according to which Different olefins, component B can be: 1-chloroethylethylphosphinate, 1-chloroethylphosphinate, 1,2-dichloroethylethylphosphinate, 1,2 -dichloroethylphosphinate, 3-chloropropylpropylphosphinate, 3-chloropropylphosphinate, 4-chlorobutylethylphosphinate, 4-chlorobutylate a phosphinate, a 4-chlorobutylphosphinate, a chlorocyclohexylethylphosphinate, a chlorocyclohexylcyclohexylphosphinate, a chlorocyclohexylcyclohexylphosphinate,
  • Example 4 5 6 7 8 Chloroolefin Vinyl chloride 3-chloropropene 4-chlorobutene Chlorocyclohexene 1,2-dichloroethylene Add amount / g 2.9 7.5 18.9 2.9 19.3 Chlorine content / ppm 117 194 533 65 793
  • the aluminum diethylphosphinate was prepared in the same manner as in Example 1 and mixed with the chlorine-containing compound shown in Table 2 to prepare a mixture of the component A + the component B.
  • the A+B mixture of Examples 4 to 14 was uniformly mixed with the component C of Example 2 and/or the component D of Example 3 to obtain a flame retardant composition, the composition of which is shown in Table 3.
  • an aluminum diethylphosphinate solution (theoretical dry weight 200 g) was prepared, 2 g of ethyl ethylphosphinate and 1 g of aluminum phosphite were added, stirred uniformly, filtered, washed twice with 600 ml of water, and then filtered. It was washed with 600 ml of a 0.2 wt% aqueous solution of aluminum chloride, filtered, and dried to obtain a flame retardant composition.
  • the ethyl phosphinate content was 0.98 wt%
  • the aluminum phosphite content was 0.49 wt%
  • the chlorine element content was 98 ppm.
  • compositions of Examples 1 to 3 were uniformly mixed to obtain a composition, and the composition thereof is as shown in Table 3 below:
  • Example 15-26, 4, 6 and Comparative Examples 1-3 were mixed at a temperature of 230-260 ° C with PBT, glass fiber, and auxiliary agent at a weight ratio of 10:50:30:10
  • Comparative Example 4 is a blank sample comparison without adding an additive composition, that is, a weight ratio of 0:50:30:10, and extruded from a twin-screw extruder to obtain a flame-retardant thermoplastic polymer molding material, and a sample test Its combustion performance and mechanical properties, the measured results are shown in Table 4 below:
  • ⁇ D degree of screw corrosion
  • the color test was performed on a Color-Eye-7000A colorimeter (GretagMacbeth).
  • the specific test method is:
  • chlorine content detection standard prEN 14582-2002 halogen detection method.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Fireproofing Substances (AREA)

Abstract

La présente invention concerne une composition d'additif pour polymère, son procédé de préparation, et un matériau de moulage de polymère thermoplastique ignifugeant constitué de celle-ci. La composition d'additif pour polymère comprend les composants suivants : composant A, à savoir 80 % en poids à 99,99 % en poids de phosphinate de dialkyle ayant une structure telle que décrite dans la formule (I) ; composant B, à savoir 0,001 % en poids à 0,5 % en poids de chlorure ayant une teneur en poids de chlore élémentaire dans l'additif total de 60 à 800 ppm ; composant C, à savoir 0 % en poids à 20 % en poids de phosphonate d'alkyle ayant une structure telle que décrite dans la formule (II) ; composant D, à savoir 0 % en poids à 0,9 % en poids de phosphite ayant une structure telle que décrite dans la formule (III), sur la base de 100 % en poids au total, où les fractions en poids des composants C et D ne sont pas égales à 0 % en poids simultanément. L'additif de l'invention est appliqué au polymère, de sorte que le degré de corrosion du polymère ignifugeant à une vis de dispositif combiné de mélange soit fortement réduit, la perte d'énergie et de main-d'œuvre causée par le remplacement fréquent de la vis dans un procédé de traitement est réduite plus avant tandis que le coût de traitement d'équipement est diminué ; la blancheur de la partie de polymère obtenue par moulage par extrusion est supérieure à celle de la partie de polymère modifiée par un phosphinate de dialkyle normal.
PCT/CN2015/097211 2014-12-26 2015-12-12 Composition d'additif pour polymère, procédé pour sa préparation, et matériau de moulage de polymère thermoplastique ignifugeant constitué de celle-ci WO2016101800A1 (fr)

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CN201410826125.XA CN104497504B (zh) 2014-12-26 2014-12-26 一种用于聚合物的添加剂组合物和其制备方法及由其组成的阻燃热塑性聚合物模塑材料

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CN107141511A (zh) * 2017-05-25 2017-09-08 广州铂钡信息科技有限公司 一种用于聚合物的添加剂及其制备方法
EP3214118A4 (fr) * 2014-10-29 2018-05-30 Guangzhou Kingsky Material Co., Ltd. Composition d'additif pour polymère et son procédé de préparation et matière à mouler de type polymère thermoplastique ignifuge la contenant
CN114085422A (zh) * 2021-11-30 2022-02-25 广东宇星阻燃新材股份有限公司 一种无机次磷酸铝的制备方法及无机次磷酸铝在阻燃pbt中的应用
CN114685856A (zh) * 2022-04-21 2022-07-01 兰州瑞朴科技有限公司 二乙基次膦酸铝的制备方法
EP3964517A4 (fr) * 2019-03-07 2023-05-31 Li, Jie Sel composite métallique d'acide dialkylphosphinique-alkylphosphite, son procédé de préparation et son utilisation

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CN105085988B (zh) * 2014-12-26 2017-06-30 肖群 一种用于聚合物的添加剂组合物和其制备方法及由其组成的阻燃热塑性聚合物模塑材料
DE102016213281A1 (de) 2016-07-20 2018-01-25 Clariant Plastics & Coatings Ltd Flammschutzmittelmischungen, ihre Herstellung und ihre Verwendung
DE102017212100A1 (de) * 2017-07-14 2019-01-17 Clariant Plastics & Coatings Ltd Additivmischungen für Kunststoffe, lasermarkierbare Polymerzusammensetzungen enthaltend diese und deren Verwendung
CN107417977B (zh) * 2017-07-19 2019-07-12 广州铂钡信息科技有限公司 一种用于聚合物的添加剂及其制备方法
CN111825883A (zh) * 2019-04-15 2020-10-27 黎杰 多二烷基次膦酸金属复合盐和/或其混合物，和其用途
CN114806601B (zh) * 2022-05-10 2023-04-07 江苏利思德新材料有限公司 一种烷基次膦酸盐组合物及其制备方法和应用

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