WO2017140123A1 - 一种用于聚合物的添加剂及其制备方法以及由其组成的聚合物组合物 - Google Patents
一种用于聚合物的添加剂及其制备方法以及由其组成的聚合物组合物 Download PDFInfo
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- WO2017140123A1 WO2017140123A1 PCT/CN2016/103687 CN2016103687W WO2017140123A1 WO 2017140123 A1 WO2017140123 A1 WO 2017140123A1 CN 2016103687 W CN2016103687 W CN 2016103687W WO 2017140123 A1 WO2017140123 A1 WO 2017140123A1
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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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
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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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
- C08L23/12—Polypropene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/06—Polystyrene
Definitions
- the present invention relates to an additive, and more particularly to an additive for a thermoplastic polymer, a process for the preparation thereof, and a polymer composition composed of the same.
- Tetrakis( ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propanoyloxymethyl)methane as described above is an important commercial additive for thermoplastic polymers. For example, it protects organic materials, especially thermoplastic polymers, from degradation by heat, oxidation and/or actinic. Generally, the addition reaction of 2,6-di-tert-butylphenol and methyl acrylate is carried out to form methyl ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, and then It is obtained by transesterification with pentaerythritol.
- the tetrakis( ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl)methane described in the above formula is used as an additive in a polymer such as polypropylene or polystyrene.
- Polymers are used as materials for home appliances, OA, packaging materials, daily necessities, toys, sports equipment, shoe materials, cables, instrumentation, electronic components and equipment, building materials and automotive materials, especially home appliances, OA. , toys and automotive materials, stricter odor and VOC requirements.
- an auxiliary agent especially the tetrakis( ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl)methane.
- the melt stability of the polymer is challenged, and the polymer emits a part of the volatiles, which are generally derived from residual monomers, solvents, additives, and small molecules produced by degradation.
- the method of adding a stripping agent can significantly reduce the odor, residual monomer, solvent and VOC content of the polymer.
- a stripping agent that is, assisting devolatilization
- R.J. Orbrecke "Polymerization” refers to a method in which a single-screw extruder and a twin-screw extruder are simultaneously introduced into a stripping agent to carry out devolatilization.
- a method of removing residual monomers from a polymer comprises pouring water into a melt or a suitable condensable fluid, and then passing the effluent through a flash tank.
- 98124504.8 discloses a method for removing volatile materials, comprising discharging a foaming aid with a nozzle device, adding it in the opposite direction to the composition stream, and applying the composition under pressure without foaming. Introduced into the mixing device for mixing, and then extruded into the devolatilization tank by an extrusion device to make the polymer at a pressure and temperature of 1.4 or higher.
- a foaming product thereby removing volatile materials, although the above method can obtain a polymer composition having a low amount of volatile materials, since a stripping agent is directly added to a raw material, a large amount of a stripping agent cannot be immersed in the raw material. On the one hand, it is difficult to operate the screw extruder.
- the present inventors have discovered through a great deal of research that when a specific content is contained in tetrakis( ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propanoyloxymethyl)methane described in the above formula.
- the melt stability of the corresponding polymer container can be significantly improved.
- the addition of trace amounts of bromine-containing materials can significantly improve the melt stability of polymer products.
- the invention is achieved by the following technical solutions:
- Formula X which may have the chemical name: tetrakis( ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propanoyloxymethyl)methane.
- the weight content of the bromine element is from 1 ppm to 82 ppm based on the total weight of the additive A.
- the bromine element is derived from a metal bromide or a bromide-containing organic compound.
- the metal of the metal bromide is preferably an alkali metal or an alkaline earth metal.
- Specific examples of the metal bromide include sodium bromide, potassium bromide, calcium bromide, and magnesium bromide. They may be used alone or in combination of two or more.
- the bromide-containing organic compounds useful in the present invention include, but are not limited to, 1-bromopropane, bromochloromethane, dibromomethane, and tetrabromobisphenol A, ethylene bis(tetrabromophthalimide), ten.
- the invention also provides an additive composition comprising a compound of the formula:
- At least one other additive B different from the compound of formula X wherein the weight content of the bromine element is from 1 ppm to 82 ppm based on the total weight of the additive composition; preferably from 50 to 99.9% based on the total weight of the additive composition.
- the other additive B is one or more of the following:
- Antioxidants including the following types:
- alkylated monophenols such as 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethyl Phenolic, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-( ⁇ -methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2 , 6-di-tert-butyl-4-methoxymethylphenol, a linear or branched nonylphenol such as 2,6-dimercapto-4-methylphenol, 2,4-dimethyl -6-(1'-methylundecane-1'-yl)phenol, 2,4-di
- alkylthiomethylphenol such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctyl Thiomethyl-6-ethylphenol, 2,6-di(dodecylthio)methyl-4-nonylphenol.
- hydroquinones and alkylated hydroquinones such as 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2 ,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4 -hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
- 2,6-di-tert-butyl-4-methoxyphenol 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2 ,6-dip
- Tocopherols such as alpha-tocopherol, beta-tocopherol, gamma-tocopherol, delta-tocopherol and mixtures thereof (vitamin E).
- hydroxylated thiodiphenyl ether such as 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4, 4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis (3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl)disulfide.
- 2,2'-thiobis(6-tert-butyl-4-methylphenol 2,2'-thiobis(4-octylphenol), 4, 4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis (3,6-di-sec-amylphenol), 4,4'-bis(2,6-di
- 1.6 alkylene bisphenols such as 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethyl Phenol), 2,2'-methylenebis[4-methyl-6-( ⁇ -methylcyclohexyl)phenol], 2,2'-methylenebis(4-methyl -6-cyclohexylphenol), 2,2'-methylenebis(6-fluorenyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol) , 2,2'-ethylenebis(4,6-di-tert-butylphenol), 2,2'-ethylenebis(6-tert-butyl-4-isobutylphenol), 2,2' -methylenebis[6-( ⁇ -methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-( ⁇ , ⁇ -dimethylbenzyl)-4- Nonylphenol], 4,4'
- O-, N- and S-benzyl compounds for example 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, 4-hydroxy-3,5-di Octadecylmethylbenzyl mercaptoacetate, tridecyl 4-hydroxy-3,5-di-tert-butylbenzyl decylacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl Amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl) Sulfide, isooctyl 3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate.
- Aromatic hydroxybenzyl compound for example 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-double ( 3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl Phenyl).
- Triazine compounds such as 2,4-bis(octylfluorenyl)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylfluorenyl -4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octyldecyl-4,6-bis (3,5-di-tert Butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3 Triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxyl -2,6-dimethylbenzyl)isocyanurate, 2,4,
- benzylphosphonate such as dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 3, Bis(octadecyl) 5-di-tert-butyl-4-hydroxybenzylphosphonate, di(octadecyl) 5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, Calcium salt of monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.
- Amidophenols for example 4-hydroxylauranilide, 4-hydroxystearylanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.
- an ester of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with a monohydric or polyhydric alcohol for example with methanol, ethanol, octanol, stearyl alcohol, 1,6-hexanediol, 1, 9-decanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiglycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N, N'-bis(hydroxyethyl)oxamide, 3-thiaundecyl alcohol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1 An ester of p-hetero-2,6,7-trioxabicyclo[2.2.2]octane.
- An amide of 1.16 ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propanoic acid such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropanoyl)hexa Methylenediamine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine, N,N'-bis(3,5-di-tert-butyl) 4-Hydroxyphenylpropionyl)ruthenium, N,N'-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propanoyloxy)ethyl]oxamide .
- 2-hydroxybenzophenones such as 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ',4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivatives.
- esters of substituted and unsubstituted benzoic acids such as 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butyl) Benzoyl) resorcinol, benzoylresorcinol, 2,5-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, 3,5-di-tert-butyl Cetyl 4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2,5-di-tert-butyl-4-hydroxybenzoic acid 2-methyl Base-4,6-di-tert-butylphenyl ester.
- acrylates such as ⁇ -cyano- ⁇ , ⁇ -diphenylacrylate, ⁇ -cyano- ⁇ , ⁇ -diphenyl isooctyl acrylate, ⁇ -methyl cinnamate methyl ester, ⁇ - cyano- ⁇ -methyl-p-methoxycinnamate methyl ester, ⁇ -cyano- ⁇ -methyl-p-methoxycinnamate butyl ester, ⁇ -methyl ester-p-methoxycinnamate methyl ester, N - ( ⁇ -carbomethoxy- ⁇ -cyanovinyl)-2-methylindoline, tetrakis( ⁇ -cyano- ⁇ , ⁇ -diphenyl) neopentyl acrylate.
- Nickel compounds such as nickel complexes of 2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenol, such as 1:1 or 1:2 complexes, Single with or without other ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid
- Alkyl esters such as nickel salts of methyl or ethyl esters, nickel complexes of ketone oximes such as 2-hydroxy-4-methylphenylundecyl oxime, 1-phenyl-4-lauroyl-5-hydroxyl
- a nickel complex of pyrazole with or without other ligands such as nickel complexes of 2,2'-thiobis[4-(1,1,3,3-tetramethylbutyl)phenol, such as 1:1 or 1:2 complexes, Single with or without other ligands such as
- a hindered amine such as bis(1-undecyloxy-2,2,6,6-tetramethyl-4-piperidinyl) carbonate, bis(2,2,6,6-tetramethyl) 4-piperidinyl) sebacate, bis(2,2,6,6-tetramethyl-4-piperidinyl) succinate, bis(1,2,2,6,6-penta 4-piperidinyl) sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2, 2,6,6-pentamethyl-4-piperidinyl)n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, 1-(2-hydroxyethyl)-2 a condensate of 2,6,6-tetramethyl-4-hydroxypiperidine with succinic acid, N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)hexa Linear or
- oxalic acid amides such as 4,4'-dioctyloxyoxalylamine, 2,2'-diethoxyoxalylaniline, 2,2'-dioctyloxy-5,5'-di-uncle Butyl oxanilide, 2,2'-bis(dodecyloxy)-5,5'-di-tert-butyloxalylanilide, 2-ethoxy-2'-ethyloxalylanilide , N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethyloxalylaniline and its 2-ethoxy- a mixture of 2'-ethyl-5,4'-di-tert-butyl oxalic acid anilide, a mixture of o- and p-methoxy disubstituted oxalanilide, and o- and
- Metal deactivators such as N,N'-diphenyl oxamide, N-salicylaldehyde-N'-salicyloyl hydrazide, N,N'-bis(salicyl) hydrazine, N,N'-double (3,5-di-tert-butyl-4-hydroxyphenylpropionyl)indole, 3-salicylamino-1,2,4-triazole, bis(benzylidene)oxalyl dihydrazide, oxalyl Aniline, isophthalic dioxime, sebacyl bisphenyl hydrazine, N, N'-diacetyladipate dihydrazide, N, N'-bis(salicyl) oxalyl dihydrazide, N, N '-Bis(salicyloyl)thiopropionyl dioxime.
- Phosphites and phosphonites such as triphenyl phosphite, diphenylalkyl phosphite, phenyl dialkyl phosphite, tris(nonylphenyl) phosphite, phosphorous acid tris Lauryl ester, tris(octadecyl)phosphite, distearyl pentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol diphosphite Ester, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl- 4-methylphenyl) pentaerythr
- Hydroxylamines such as N,N-dibenzylhydroxylamine, N,N-diethylhydroxylamine, N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-di(tetradecane) Hydroxyamine, N,N-di(hexadecyl)hydroxylamine, N,N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecane Base-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine derived from hydrogenated tallow fatty amine.
- a nitrone such as N-benzyl- ⁇ -phenyl nitrone, N-ethyl- ⁇ -methyl nitrone, N-octyl- ⁇ -heptyl nitrone, N-lauryl- ⁇ -ten Monoalkyl nitrone, N-tetradecyl- ⁇ -tridecyl nitrone, N-hexadecyl- ⁇ -pentadecyl nitrone, N-octadecyl- ⁇ -heptadecane Nitrosone, N-hexadecyl- ⁇ -heptadecyl nitrone, N-octadecyl- ⁇ -pentadecyl nitrone, N-heptadecyl- ⁇ -heptadecyl nitrate Ketone, N-octadecyl- ⁇ -hexadecyl nitrone, nitrone derived from N,N
- a thio-association agent such as dilauryl thiodipropionate, dimyristyl thiodipropionate, distearyl thiodipropionate or distearyl disulfide.
- Peroxide scavengers for example esters of beta-thiodipropionic acid, such as lauryl ester, stearyl ester, myristyl or tridecyl ester, mercaptobenzimidazole or 2-mercaptobenzoene Zinc salt of imidazole, zinc dibutyl dithiocarbamate, two (ten Octaalkyl)disulfide, pentaerythritol tetrakis( ⁇ -dodecylmercapto)propionate.
- Polyamide stabilizers for example copper salts and divalent manganese salts in combination with iodine and/or phosphorus compounds.
- Alkaline co-stabilizers such as melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, anthraquinone derivatives, amines, polyamides, polyurethanes, alkali metal salts of higher fatty acids and Alkaline earth metal salts such as calcium stearate, zinc stearate, magnesium sulphate, magnesium stearate, sodium ricinolate and potassium palmitate, bismuth catechin or zinc pyrocate.
- Alkaline co-stabilizers such as melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, anthraquinone derivatives, amines, polyamides, polyurethanes, alkali metal salts of higher fatty acids and Alkaline earth metal salts such as calcium stearate, zinc stearate, magnesium sulphate, magnesium stearate, sodium
- Nucleating agents for example inorganic substances such as talc, metal oxides such as titanium dioxide or magnesium oxide, preferably phosphates, carbonates or sulfates of alkaline earth metals; organic compounds such as mono- or polycarboxylic acids and salts thereof, for example 4 -tert-Butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds such as ionic copolymers (ionomers).
- inorganic substances such as talc, metal oxides such as titanium dioxide or magnesium oxide, preferably phosphates, carbonates or sulfates of alkaline earth metals
- organic compounds such as mono- or polycarboxylic acids and salts thereof, for example 4 -tert-Butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate
- polymeric compounds such as ionic copolymers (ionomers).
- additives such as plasticizers, lubricants, emulsifiers, pigments, rheological additives, catalysts, flow regulators, fluorescent whitening agents, flame retardants, antistatic agents and blowing agents.
- Preferred additive B is:
- Processing additives such as anti-skid/anti-caking additives, plasticizers, fluorescent whitening agents, antistatic agents and foaming agents.
- the invention also provides a polymer composition
- a polymer composition comprising a polymer in an amount of from 30 to 99.9% by weight, a filler in an amount of from 0 to 60% by weight, and a polymer content of from 0.1 to 10% by weight of the invention.
- Additive A is a polymer composition comprising a polymer in an amount of from 30 to 99.9% by weight, a filler in an amount of from 0 to 60% by weight, and a polymer content of from 0.1 to 10% by weight of the invention.
- the present invention also provides a polymer composition
- a polymer composition comprising a polymer in an amount of from 30 to 99.9% by weight, a filler in an amount of from 0 to 60% by weight, and an additive composition in an amount of from 0.1 to 10% by weight.
- thermosetting and thermoplastic polymers selected from one or more of the following:
- Polymers of monoolefins and diolefins such as polypropylene, polyisobutylene, polybutene, poly-4-methylpentene, polyvinylcyclohexane, polyisoprene or polybutadiene, and rings
- Polymers of olefins such as polymers of cyclopentene or norbornene, polyethylene (optionally crosslinked), such as high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high Density and ultra high molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE).
- HDPE high density polyethylene
- HDPE-HMW high density and high molecular weight polyethylene
- HDPE-UHMW high Density and ultra high molecular weight polyethylene
- MDPE medium density polyethylene
- LDPE low density polyethylene
- LLDPE linear low density polyethylene
- Copolymers of monoolefins and diolefins with each other or with other vinyl monomers such as ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene/ But-1-ene copolymer, propylene/isobutylene Copolymer, ethylene/but-1-ene copolymer, ethylene/hexene copolymer, ethylene/methylpentene copolymer, ethylene/heptene copolymer, ethylene/octene copolymer, ethylene/vinylcyclohexane Copolymer, ethylene/cycloolefin copolymer (such as ethylene/norbornene, such as COC), ethylene/1-olefin copolymer (where 1-olefin is produced in situ); propylene/butadiene copolymer, isobutylene/isoprene Diene copoly,
- Hydrocarbon resins e.g., C5-C9, including hydrogenated modified products thereof (e.g., tackifiers) and mixtures of polyalkylenes and starches.
- the homopolymers and copolymers of 1-4 may have any stereostructure, including syndiotactic, isotactic, semi-isotactic or random; among them, a random polymer is preferred. Also included are stereoblock polymers.
- Polystyrene poly-p-methyl styrene, poly- ⁇ -methyl styrene.
- Aromatic homopolymers and copolymers derived from vinyl aromatic monomers including all isomers of styrene, alpha-methylstyrene, vinyltoluene, especially p-vinyltoluene , all isomers of ethyl styrene, propyl styrene, vinyl biphenyl, vinyl naphthalene and vinyl anthracene and mixtures thereof.
- the homopolymers and copolymers can have any stereostructure, including syndiotactic, isotactic, semi-isotactic or random; among them, random polymers are preferred. Also included are stereoblock polymers.
- PCHE polycyclohexylethylene
- PVCH polyvinylcyclohexane
- a graft copolymer of a vinyl aromatic monomer such as styrene or alpha-methylstyrene such as styrene grafted polybutadiene, styrene grafted polybutadiene-styrene or Polybutadiene-acrylonitrile copolymer; styrene and acrylonitrile (or methacrylonitrile) grafted polybutadiene; styrene, acrylonitrile and methyl methacrylate grafted polybutadiene; benzene Ethylene and maleic anhydride grafted polybutadiene; styrene, acrylonitrile and maleic anhydride or maleimide grafted polybutadiene; styrene and maleic amide Imine-grafted polybutadiene; styrene and alkyl acrylate or alkyl methacrylate grafted polybutadiene; stt
- Halogen-containing polymers such as polychloroprene, chlorinated rubber, chlorinated or brominated copolymers of isobutylene-isoprene (halogenated rubber), chlorinated or chlorosulfonated polyethylene, ethylene and a copolymer of ethylene chloride, an epichlorohydrin homopolymer and a copolymer, especially a polymer of a halogen-containing vinyl compound, such as polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride; And copolymers thereof such as vinyl chloride / vinylidene chloride, vinyl chloride / vinyl acetate or vinylidene chloride / vinyl acetate copolymer.
- halogen-containing polymers such as polychloroprene, chlorinated rubber, chlorinated or brominated copolymers of isobutylene-isoprene (halogenated rubber), chlorinated or
- Copolymers of monomers referred to in 9 or copolymers with other unsaturated monomers such as acrylonitrile/butadiene copolymers, acrylonitrile/alkyl acrylate copolymers, acrylonitrile / Alkoxyalkyl acrylate or acrylonitrile / vinyl halide copolymer or acrylonitrile / alkyl methacrylate / butadiene terpolymer.
- Polymers derived from unsaturated alcohols and amines or their acyl derivatives or acetals such as polyvinyl alcohol, polyvinyl acetate, polyvinyl polystearate, poly(vinyl benzoate), vinyl polymaleate , polyvinyl butyral, polyallyl phthalate or polyallyl melamine; and copolymers thereof with the olefins mentioned in the above 1.
- cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or copolymers thereof with diglycidyl ether.
- Polyacetals such as polyoxymethylene and those polyoxymethylenes containing ethylene oxide as a comonomer; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.
- Polyurethanes which are derived on the one hand from hydroxyl terminated polyethers, polyesters or polybutadienes and on the other hand from aliphatic or aromatic polyisocyanates and their precursors.
- Polyamides and copolyamides derived from diamines and dicarboxylic acids and/or derived from aminocarboxylic acids or corresponding lactams for example polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6 /9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aramid obtained from meta-xylene diamine and adipic acid; elasticity in the presence or absence of modifier a polyamide prepared from hexamethylenediamine and isophthalic acid and/or terephthalic acid, such as poly-2,4,4-trimethylhexamethylene terephthalamide or poly a phenylene isophthalamide; and a block copolymer of the above polyamide with a polyolefin, an olefin copolymer, an ionomer or a chemically bonded or grafted elastomer; or with a polyether, for example, with a polyethylene glycol a block copolymer of polypropylene glyco
- a polyester derived from a dicarboxylic acid and a diol and/or derived from a hydroxycarboxylic acid or a corresponding lactone or lactide such as polyethylene terephthalate, polybutylene terephthalate , poly-1,4-dimethylolcyclohexane terephthalate, polyalkylene naphthalate and polyhydroxybenzoate, and copolyetherester derived from a hydroxyl terminated polyether; Polyester modified with polycarbonate or MBS.
- Copolyesters may include, for example, but are not limited to, polybutylene succinate/butylene terephthalate, polybutylene adipate/butylene terephthalate, polyhexyl Tetramethylene dimethane / tetramethylene terephthalate, butylene glycol polysuccinate / butylene glycol adipate, butylene glycol polyacrylate / carbonate, poly-3-hydroxyl Butyrate/3-hydroxyoctanoate copolymer, poly-3-hydroxybutyrate/3-hydroxyhexanoate/3-hydroxydecanoate terpolymer.
- aliphatic polyesters may include, for example, but are not limited to, poly(hydroxyalkanoates), especially polypropiolactone, polybutyrolactone, polypivalolactone, polyvalerolactone, and polyhexanolate.
- Lactone polyethylene succinate, propylene glycol polysuccinate, polybutylene succinate, hexamethylene polysuccinate, polyethylene adipate, propylene glycol adipate, Polybutylene adipate, polyhexamethylene adipate, polyethylene oxalate, propylene glycol oxalate, polybutylene oxalate, hexamethylene oxalate, polysebacic acid
- Ethylene glycol esters polypropylene glycol phthalate, polybutylene phthalate and polylactic acid (PLA) and corresponding polyesters modified with polycarbonate or MBS.
- polylactic acid means a homopolymer preferably of poly-L-lactide and any blend or alloy thereof with other polymers; a copolymer of lactic acid or lactide with other monomers, Other monomers such as hydroxycarboxylic acids such as glycolic acid, 3-hydroxybutyric acid, 4-hydroxybutyric acid, 4-hydroxyvaleric acid, 5-hydroxyvaleric acid, 6-hydroxycaproic acid and cyclic forms thereof; the term "lactic acid "Or Lactide” includes L-lactic acid, D-lactic acid, mixtures thereof and dimers, ie, L-lactide, D-lactide, meso-lactide, and any mixture thereof.
- Crosslinked polymers which are derived from aldehydes on the one hand and phenols, ureas and melamines on the other hand, such as phenol/formaldehyde resins, urea/formaldehyde resins and melamine/formaldehyde resins.
- An unsaturated polyester resin derived from a copolyester of a saturated and unsaturated dicarboxylic acid and a polyol and a vinyl compound as a crosslinking agent, and a halogen-containing modified product thereof having low flammability.
- a crosslinkable acrylic resin derived from a substituted acrylate such as an epoxy acrylate, urethane acrylate or polyester acrylate.
- a promoter is crosslinked using a conventional hardener such as an acid anhydride or an amine.
- Blends (polymer blends) of the above polymers such as PP/EPDM, polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC /ASA, PC/PBT, PVC/CPE, PVC/Acrylate, POM/Thermoplastic PUR, PC/Thermoplastic PUR, POM/Acrylate, POM/MBS, PPO/HIPS, PPO/PA66 and Copolymer, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABS or PBT/PET/PC.
- Natural and synthetic organic materials which are pure monomeric compounds or mixtures of these compounds, such as mineral oils, animal and vegetable fats, oils and waxes, or based on synthetic esters (eg phthalates, adipic acid) Oils, fats and waxes of esters, phosphates or trimellitates, and mixtures of synthetic esters and mineral oils in any weight ratio, typically those used as spinning compositions, and aqueous emulsions of these materials.
- Preferred organic materials are:
- olefin monomers such as ethylene and propylene and higher 1-olefins such as 1-butene, 1-pentene, 1-hexene or 1-octene. Preference is given to polyethylene LDPE and LLDPE, HDPE and polypropylene.
- thermoplastics such as polystyrene, styrene-acrylonitrile copolymer, acrylonitrile-butadiene-styrene copolymer, polyvinyl chloride, polyvinylidene chloride, polyvinyl acetate, polyvinyl butyral , ethylene-vinyl alcohol copolymer, polyethylene terephthalate (PET), polybutylene terephthalate (PBT), liquid crystal polyester (LCP), polyacetal (such as POM), poly Amide (PA), polycarbonate, polyurethane, and polyphenylene sulfide (PPS); polymer blends or polymer alloys formed from two or more of these resins; and by adding fillers such as glass fibers, carbon fibers, and half Carbonized fiber, cellulose fiber and glass beads, flame retardant, foaming agent, antimicrobial agent, crosslinking agent, polyolefin resin fine powder, polyolefin wax, ethylene bisamide wax, metal soap
- thermosetting resin may include thermosetting resins such as epoxy resins, melamine resins, and unsaturated polyester resins; and by incorporating fillers such as glass fibers, carbon fibers, semi-carbonized fibers, cellulose fibers, and glass beads, A compound obtained by emulsifier or the like, alone or in combination with these resins.
- thermosetting resins such as epoxy resins, melamine resins, and unsaturated polyester resins
- fillers such as glass fibers, carbon fibers, semi-carbonized fibers, cellulose fibers, and glass beads, A compound obtained by emulsifier or the like, alone or in combination with these resins.
- biodegradable polymers of natural or synthetic origin including, but not limited to, polyethylene succinate, polybutylene succinate, butylene polysuccinate/butyl adipate Glycol ester, polybutylene succinate/butylene carbonate, polybutylene succinate/butylene terephthalate, polycaprolactone, poly(hydroxyalkanoate), poly -3-hydroxybutyrate, polylactic acid, polyester amide or a blend of these materials with natural or modified starch, polysaccharide, lignin, wood flour, cellulose or chitin.
- the polymer is preferably a thermoplastic natural or synthetic polymer, especially one selected from the group consisting of the above.
- Preferred are polyolefin homopolymers or copolymers, starch modified polyolefin or starch based polymer composites, particularly preferably polyethylene, polypropylene, poly Ethylene copolymer or polypropylene copolymer.
- the filler includes, for example, calcium carbonate, silica, glass fiber, glass bubbles, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood powder, powder of other natural products, Synthetic fiber, stearate used as a filler such as calcium stearate or zinc stearate.
- the polymer molding compositions of the present invention are suitable for use in the production of fibers, coatings, films or moldings.
- the present invention also provides a process for preparing a polymer composition comprising the additive A of the present invention and/or the additive composition of the present invention, together with polymer pellets and optional fillers.
- the extruder unit is selected from a single screw extruder or a twin screw extruder.
- the preferred processing temperature is 170 to 200 ° C for polystyrene, 200 to 300 ° C for polypropylene, 250 to 290 ° C for polyethylene terephthalate (PET), and polybutylene terephthalate.
- the alcohol ester (PBT) is 230 to 270 ° C, 260 to 290 ° C for polyamide-6 (PA6), 260 to 290 ° C for polyamide 66 (PA66), and 280 to 320 ° C for polycarbonate.
- the compounding device which can be used in the present invention is a single-screw extruder or a twin-screw extruder, and the effective screw length for the present invention is 20 to 4 OD in the case of a single-screw extruder; effective in the present invention The screw length is 8 to 48 D in the case of a twin screw extruder.
- the dibutyltin oxide is selected as a catalyst, and the catalyst and the reaction raw material methyl 3,5-di-tert-butyl-4-hydroxyphenylpropionate (commercially available) and pentaerythritol (commercially available) are added to the reaction vessel, wherein 3, 5 - 380 g of di-tert-butyl-4-hydroxyphenylpropionate and 42 g of pentaerythritol, the molar ratio of the two is about 4.2, the amount of the catalyst is 0.3 g, the pressure of the reaction vessel is adjusted to 650 Pa, and the temperature is raised after the reaction at 175 ° C for 7 hours.
- the reaction was continued at 200 ° C for 1 h, and the temperature was lowered to 145 ° C for a half hour neutralization reaction.
- the obtained product is selected from methanol as a crystallization solvent, and the target product is obtained by cooling and crystallization filtration.
- the compound prepared in Example 1 was separately compounded with a bromine-containing compound, and the weight of the product of Example 1 in the polymer additive A was adjusted to obtain a polymer additive A having a specific bromine content, as shown in Table 1.
- the specific compounding method is as follows: firstly, the compound prepared in Example 1 and the bromine-containing substance are compounded according to the ratio of Table 1 to a mother sample having a higher bromine content, and the weight content of the bromine element is measured, and then according to the final result. The content of the desired bromine element was calculated by weighting the product of the second addition of Example 1, to finally obtain the polymer additive A, and then the weight content of the bromine element was measured again.
- the weight content of the bromine element is determined by the following method: accurately weighing the polymer additive A 2g in an analytical balance, pouring it into a 100 ml digestion bottle, and then adding 97% concentrated sulfuric acid 5 ml, at a preset temperature of 300 ° C iron plate Heating in a heating instrument for 10 minutes, Then add 5ml of 68% nitric acid, and then keep heating for 20 minutes, the particles are completely decomposed and then cooled to room temperature. After adding 20ml of hydrogen peroxide and acid to pH 7, dilute the liquid with deionized water and pass the liquid. The sample tube was introduced into an ICP detector to determine the concentration of bromine.
- Example 2 The bromine of Example 2 is derived from: dibromomethane,
- the bromine of Examples 3 and 4 was derived from: sodium bromide.
- Example 2 The compounds prepared in Example 1 were compounded according to the above methods, and the specific contents are shown in Table 2:
- the bromine of Comparative Example 1 is derived from: dibromomethane,
- the bromine of Comparative Example 2 was derived from: sodium bromide.
- the above polypropylene and other components are first dry mixed in a high speed mixer at a speed of about 1000 rpm for 1 minute. If talc is added, the talc filler is added and mixed for another 3 minutes.
- the mixed raw materials are placed in a twin-screw extruder and melt-extruded and granulated.
- the process conditions are: one zone 200 ° C, two zones 210 ° C, three zones 220 ° C, four zones 215 ° C; twin-screw extruder
- the aspect ratio is 35, the screw speed is 450 rpm, the residence time is 1 minute, and the pressure is 10 MPa.
- the above polypropylene and other components are first placed at a high speed of about 1000 rpm.
- the mixture was dry-mixed for 3 minutes in a mixer, and the mixed raw materials were placed in a twin-screw extruder and melt-extruded and granulated.
- the process conditions were as follows: the temperature of each section of the barrel was maintained at 200 ° C, and the length of the twin-screw extruder was long. The ratio is 35, the screw speed is 450 rpm, the residence time is 1 minute, and the pressure is 10 MPa.
- Example 5 Example 6
- Example 7 Example 2 product 0.1
- Example 3 product 0.3
- Example 4 product 0.5
- Polystyrene 99.7 Ultraviolet light absorber
- talcum powder 20 glass fiber 30 Melt stability O O O
- Comparative example 3 Comparative example 4 Comparative Example 1 product 0.1 Comparative Example 2 product 0.3 Polypropylene 69.9 Polystyrene 99.7 Ultraviolet light absorber talcum powder glass fiber 30 Melt stability X X
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Abstract
Description
实施例5 | 实施例6 | 实施例7 | |
实施例2产物 | 0.1 | ||
实施例3产物 | 0.3 | ||
实施例4产物 | 0.5 | ||
聚丙烯 | 69.9 | 79 | |
聚苯乙烯 | 99.7 | ||
紫外光吸收剂 | 0.5 | ||
滑石粉 | 20 | ||
玻璃纤维 | 30 | ||
熔融稳定性 | O | O | O |
对比例3 | 对比例4 | |
对比例1产物 | 0.1 | |
对比例2产物 | 0.3 | |
聚丙烯 | 69.9 | |
聚苯乙烯 | 99.7 | |
紫外光吸收剂 | ||
滑石粉 | ||
玻璃纤维 | 30 | |
熔融稳定性 | X | X |
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CN201610089321.2 | 2016-02-17 |
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WO2017140123A1 true WO2017140123A1 (zh) | 2017-08-24 |
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CN114100591A (zh) * | 2021-11-12 | 2022-03-01 | 中触媒新材料股份有限公司 | 一种用于分子筛吸附剂连续脱水活化装置及方法 |
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CN106360877A (zh) * | 2016-11-17 | 2017-02-01 | 无锡市长安曙光手套厂 | 一种淀粉乙烯‑醋酸乙烯酯复合发泡剂鞋底材料 |
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WO1999029776A1 (en) * | 1997-12-05 | 1999-06-17 | Minnesota Mining And Manufacturing Company | Flame retardant compositions |
CN1471410A (zh) * | 2000-10-30 | 2004-01-28 | ���зҵ�����˾ | 具有可控变色速度的热熔融湿度指示剂粘合剂组合物 |
CN102241852A (zh) * | 2010-09-25 | 2011-11-16 | 深圳市科聚新材料有限公司 | 一种eva阻燃剂及其制备方法 |
CN102634290A (zh) * | 2012-04-16 | 2012-08-15 | 江苏泰特尔化工有限公司 | 一种双组份透明环氧树脂led贴片封装胶 |
CN105461960A (zh) * | 2016-02-17 | 2016-04-06 | 黄秀茹 | 一种用于聚合物的添加剂及其制备方法以及由其组成的聚合物组合物 |
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US7498457B2 (en) * | 2004-07-27 | 2009-03-03 | Ciba Specialty Chemicals Corp. | Process for preparing solid particles of phenolic antioxidants |
CN102485773A (zh) * | 2010-12-06 | 2012-06-06 | 天津市北方金恒化工厂 | 一种复合抗氧化剂 |
CN104558826A (zh) * | 2014-05-26 | 2015-04-29 | 江苏汉光实业股份有限公司 | 一种聚丙烯薄膜料专用复合助剂的配方及其制备方法 |
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WO1999029776A1 (en) * | 1997-12-05 | 1999-06-17 | Minnesota Mining And Manufacturing Company | Flame retardant compositions |
CN1471410A (zh) * | 2000-10-30 | 2004-01-28 | ���зҵ�����˾ | 具有可控变色速度的热熔融湿度指示剂粘合剂组合物 |
CN102241852A (zh) * | 2010-09-25 | 2011-11-16 | 深圳市科聚新材料有限公司 | 一种eva阻燃剂及其制备方法 |
CN102634290A (zh) * | 2012-04-16 | 2012-08-15 | 江苏泰特尔化工有限公司 | 一种双组份透明环氧树脂led贴片封装胶 |
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CN114100591A (zh) * | 2021-11-12 | 2022-03-01 | 中触媒新材料股份有限公司 | 一种用于分子筛吸附剂连续脱水活化装置及方法 |
CN114100591B (zh) * | 2021-11-12 | 2023-08-22 | 中触媒新材料股份有限公司 | 一种用于分子筛吸附剂连续脱水活化装置及方法 |
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