WO2005082852A1 - カーボネート骨格を有する低塩基性ヒンダードアミン化合物、合成樹脂組成物及び塗料組成物 - Google Patents
カーボネート骨格を有する低塩基性ヒンダードアミン化合物、合成樹脂組成物及び塗料組成物 Download PDFInfo
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- WO2005082852A1 WO2005082852A1 PCT/JP2005/003807 JP2005003807W WO2005082852A1 WO 2005082852 A1 WO2005082852 A1 WO 2005082852A1 JP 2005003807 W JP2005003807 W JP 2005003807W WO 2005082852 A1 WO2005082852 A1 WO 2005082852A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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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- 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
Definitions
- the present invention relates to a low basic hindered amine compound having a carbonate skeleton.
- Hindamine compounds are known to suppress photodeterioration of organic substances such as synthetic resins, and have a structure with active hydrogen due to the difference in stabilization effect due to the difference in amine structure and the magnitude of the influence from the use environment.
- Tertiary amine structures having no active hydrogen and alkyloxyamine structures having lower basicity than the tertiary amine structure have been studied. Also, studies have been made to introduce a triazine skeleton for the purpose of improving the compatibility with the synthetic resin to be stabilized and the extraction resistance.
- Hindered amine compounds having a carbonate structure are disclosed in Japanese Patent Application Laid-Open No. 62-273239 (compounds of claims and Nos. 30 and 31) and Japanese Patent Application Laid-Open No. 63-750 / 1988. No. 19 (Claims and compounds of 1-19, 1-20, 1-21), etc., and a catalyst deactivator for the production of a stabilized polyoxymethylene (co) polymer of polyolefin resin It has been proposed to use as
- Patent Publication proposes a low basic hindered amine compound having various skeletons, and a hindered amine having a carboxylate ester structure, an amide structure, a olebamate structure and an acetal structure. ing.
- the low-basic hindered amine compound exhibits excellent resistance to acid extraction, it is utilized in polyolefin-based agricultural films as disclosed in Japanese Patent Application Laid-Open No. 2001-138981, for example. Has been proposed.
- a hinderdamine compound which gives a synthetic resin a long-term stabilizing effect and has excellent resistance to acid rain and extraction by chemicals.
- the present inventors have conducted intensive studies in view of the present situation, and as a result, have found that a hindered amine compound having a force-ponet structure represented by the general formula (I) or (II) has a long-term stability of a synthetic resin.
- the present inventors have found that the compound has an excellent effect on the formation, and arrived at the present invention.
- a first aspect of the present invention provides a hindered amine compound represented by the general formula (I) or (II).
- R represents an alkyl group or hydroxyalkyl group having 1 to 30 carbon atoms, or an alkenyl group having 2 to 30 carbon atoms
- n represents an integer of 1 to 6
- n l
- 1 is an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, or a group represented by the following general formula (III)
- R represents the same alkyl group or hydroxyalkyl group having 1 to 30 carbon atoms, or the alkenyl group having 2 to 30 carbon atoms as defined for R above.
- R 1 represents an n-valent organic group having 2 to 20 carbon atoms.
- R is an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms
- R z is a hydrogen atom, an alkyl group having 1 to 22 carbon atoms or the number of carbon atoms.
- A is a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, an alkylene group having an ether bond
- n is an integer of 2 to 6
- a second aspect of the present invention is the first aspect, wherein R in the general formula (I) is an alkyl group having 4 to 22 carbon atoms, n is 2, and R 1 is an alkylene group having 2 to 12 carbon atoms. And a hindered amine compound described in (1).
- a third aspect of the present invention is that, in the general formula (I), n is 1 and R 1 is a group represented by the following general formula (I II)
- R is an alkyl group having 10 to 22 carbon atoms.
- the hindered amine compound according to the first invention is provided.
- a fourth aspect of the present invention is a synthetic resin composition obtained by mixing 0.01 to 10 parts by weight of the hinderdamine compound described in any one of the first to third aspects of the present invention with 100 parts by weight of the synthetic resin. provide.
- a fifth aspect of the present invention is a polyolefin resin composition obtained by mixing 0.05 to 5 parts by weight of a hindered amine compound according to any one of the first to third aspects of the present invention with 100 parts by weight of a polyolefin resin. I will provide a.
- a sixth aspect of the present invention provides an agricultural polyolefin film comprising the polyolefin resin composition according to the fifth aspect of the present invention.
- a coating composition stabilized by the hindered amine compound according to any one of the first to third aspects of the present invention is provided.
- An eighth aspect of the present invention is that 100 parts by weight of the synthetic resin contains any one of melamine phosphate, melamine pyrophosphate, melamine polyphosphate, piperazine phosphate, piperazine pyrophosphate, and piperazine polyphosphate. 1 to 30 parts by weight of the above as a flame retardant, A synthetic resin composition comprising 0.01 to 10 parts by weight of the hinderdamine compound described in any one of 1 to 3 above.
- the hindered amine compound of the present invention is a low basic hindered amine compound having a carbonate skeleton represented by the general formula (I) or (II).
- examples of the alkyl group having 1 to 30 carbon atoms represented by R include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like.
- the hydroxyalkyl group having 1 to 30 carbon atoms represented by R includes 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl, 2-hydroxy-2-methyl Propyl and the like.
- R may be the same or different for every n units.
- examples of the alkenyl group having 2 to 30 carbon atoms represented by R include alkenyl groups corresponding to the above-mentioned alkyl groups such as vinyl, aryl, butenyl, pentenyl and oleyl. .
- R 1 represents an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, or a group represented by the general formula (III).
- R 1 represents an alkyl group having 1 to 22 carbon atoms.
- the methyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, sec-pentyl, tert-pentyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl Tert-octyl, nonyl, isononyl, decyl, pendecyl, dodecyl, tridecyl, tetradecyl, pendudecyl, hexadecyl, hepdudecyl, octadecyl, behenyl and the like.
- examples of the alkenyl group having 2 to 22 carbon atoms represented by R 1 include alkenyl corresponding to the above alkyl groups such as vinyl, aryl, butenyl, pentenyl, and oleyl. Groups.
- R in the general formula (III) is the same as R in the general formula (I). However, it may be the same as or different from R in the general formula (I).
- R is preferably an alkyl group having 10 to 22 carbon atoms.
- the n-valent organic group having 2 to 20 carbon atoms represented by R 1 is a residue excluding the hydroxyl group of the n-valent polyvalent hydroxy compound. No.
- polyvalent hydroxy compound examples include ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, neopentyldaricol, 1,6-hexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, hydrogenated bisphenol A, hydrogenated bisphenol F, diethylene glycol, triethylene glycol, glycerin, tri Methylol propane, pentaerythritol, dipentyl erythritol and the like.
- R 2 represents a hydrogen atom, an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms.
- alkyl group having 1 to 22 carbon atoms represented by R 2 As the alkyl group having 1 to 22 carbon atoms represented by R 2, Of the kill groups, those with the appropriate number of carbon atoms can be plucked.
- examples of the alkenyl group having 2 to 22 carbon atoms represented by R 2 include the alkenyl group represented by R having the corresponding number of carbon atoms.
- R 2 may be the same or different for every n units.
- A represents a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or an alkylene group having an ether bond.
- alkylene group having 1 to 12 carbon atoms represented by A examples include methylene, 1,2-ethylene, 1,2-propylene, 1,3-propylene, tetramethylene, 1,2-butylene, 1,3 —Butylene, pentamethylene, 2,2-dimethyltrimethylene, hexamethylene, and octamethylene.
- examples of the linear or branched alkylene group having 1 to 12 carbon atoms having an ether bond represented by A include:
- Represents a linear or branched alkylene group having 4 to 40 carbon atoms having an ester bond, or an organic compound having 3 to 6 -0-C ( 0)-and having 6 to 30 carbon atoms at the terminal. Represents a group.
- X represents -CH)) 0_
- the alkylene group having 4 to 40 carbon atoms having a bond at the terminal thereof includes:
- Examples of the organic group having 3 to 6 —0-CH))-represented by X in the general formula ( ⁇ ) at the terminal include the following groups.
- the compound represented by the general formula (I) includes the compounds of the compounds No. 1 to No. 6 and the compound No. 13, and the compound represented by the general formula (II) Examples include the compounds of Compound Nos. 7 to 12.
- the present invention is not at all limited by the following compounds. (Compound No. 1)
- the method for synthesizing the compound represented by the general formula (I) is not particularly limited, and the compound can be synthesized by a general organic synthesis method shown in the synthesis in Examples described later. Recrystallization, reprecipitation, a method using a filtering agent or an adsorbent, and the like can be appropriately used.
- Synthetic resins stabilized by the hindered amine compound represented by the general formula (I) include polypropylene, low-density polyethylene, linear low-density polyethylene, high-density polyethylene, polybutene-11, poly-3-methylpentene.
- Biodegradable fats such as linear polyesters, acid-modified polyesters, and polylactic acid Polyamides such as aromatic polyesters, polyproprolactam and polyhexamethylene adipamide, polyimides, polystyrene, styrene and / or ⁇ -methylstyrene and other monomers (for example, maleic anhydride, phenylmaleimide, methacrylate) Copolymers with methyl acrylate, butadiene, acrylonitrile, etc.
- monomers for example, maleic anhydride, phenylmaleimide, methacrylate
- polyvinyl chloride polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, polyolefin Vinylid Vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-vinylidene chloride copolymer, pinyl chloride-vinylidene chloride-vinyl acetate terpolymer, vinyl chloride-acrylate copolymer
- Halogen-containing resins such as polymers, vinyl chloride monomaleic acid ester copolymers, vinyl chloride-cyclohexylmaleimide copolymers, (meth) methyl acrylate, (meth) ethyl acrylate, (meth) octyl acrylate, etc.
- Thermoplastic resins such as polyurethane and cellulose resins, thermosetting resins such as epoxy resin, phenolic resin, urea resin, melamine resin, unsaturated polyester resin, and copolymers of isoprene rubber, butadiene rubber, and butadiene-styrene.
- An elastomer such as a terpolymer rubber with a non-conjugated diene such as cyclopentagen, a cycloolefin (co) polymer, a silicone resin, or the like may be used. It may be converted or blended.
- it is a polyolefin resin.
- the above synthetic resins include stereoregularity, specific gravity, types of polymerization catalysts such as Cidara-Natta catalyst and meta-mouth catalyst in polyolefin, presence or absence of polymerization catalyst, degree of crystallization, degree of crystallization, temperature and pressure, etc.
- Polymerization conditions crystal type, lamellar crystal size measured by small-angle X-ray scattering, crystal aspect ratio, solubility in aromatic or aliphatic solvents, solution viscosity, melt viscosity, average molecular weight, degree of molecular weight distribution
- there is no difference in stabilizing effect due to the number of peaks in the molecular weight distribution, whether the copolymer is block or random, and the mixing ratio of each monomer.
- the hinderdamine compound of the present invention can be used in various moldings as a synthetic resin composition in which 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight is mixed with 100 parts by weight of the synthetic resin. Used for raw materials.
- the amount of the hindered amine compound is less than the above range, there is no stabilizing effect, and if it is more than the above range, no further effect can be expected or the properties of the resin may be impaired.
- a polyolefin resin 0.05 to 5 parts by weight, preferably 0.1 to 3 parts by weight of a hindered amine compound is mixed with 100 parts by weight of the polyolefin resin.
- the method for blending the hindered amine compound represented by the general formula (I) into a resin is not particularly limited, and a known technique for blending a stabilizer with a resin is used. Any of a method of adding the synthetic resin to the polymerization system before polymerization, a method of adding it during the polymerization, and a method of adding it after the polymerization may be used.
- the hinderdamine compound of the present invention may be used alone or in the form of granules together with other additives.
- hinderdamine compound represented by the general formula (I) of the present invention When the hinderdamine compound represented by the general formula (I) of the present invention is used for stabilizing a synthetic resin or a paint, various binders usually used for each resin are used as necessary.
- Compounding agents include, for example, phenolic antioxidants, Antioxidants, phosphorus antioxidants, UV absorbers, other hinderdamine compounds, nucleating agents, flame retardants, flame retardant aids, lubricants, fillers, plasticizers, fibrous fillers, metal stones, hides Oral talcites, antistatic agents, pigments, dyes, antibacterial agents, fungicides, preservatives, antifouling agents, antifungal agents, surfactants, compatibilizers, anti-settling agents, polymerization inhibitors, thickeners , An antifoaming agent, a coupling agent, a leveling agent, a drying agent, an anti-sagging agent, a dehydrating agent, a curing catalyst, an adhesion imparting agent
- phenolic antioxidants include, for example, heart tocopherol, 2,6-ditertiary butyl-P-cresol, 2,6-diphenyl-41-year-old kutadecyloxyphenol, distearyl (3,5-ditertiary) Butyl-4-hydroxybenzyl) phosphonate, 1,6-hexamethylenebis [(3,5-ditert-butyl-4-hydroxyphenyl) propionamide], 4,4'-thiobis (6-tert-butyl m —Cresol), 2,2 ′ —methylenebis (4-methyl-6-tert-butylphenol), 2,2, -methylenebis (4-ethyl-6-tert-butylphenol), 4,4, —butylidenebis (6-tert) Butyl-m-cresol, 2,2'-ethylidenebis (4,6-di-tert-butylphenol), 2,2, -ethylidenebis (4-second-but
- zeo-based antioxidant examples include dialkylthiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate; Acrylates) and the like.
- Examples of the phosphorus-based antioxidant include trisnonylphenylphosphite, tris [2-tert-butyl-4- (3-tert-butyl-4-hydroxy-5-methylphenylthio) -15-methylphenyl] phospho Phyto, tridecyl phosphite, octyl diphenyl phosphite, di (decyl) monophenyl phosphite, di (tridecyl) pen erythritol diphosphite, di (nonyl phenyl) phenyl erythritol diphosphite, bis , 4-di-tert-butylphenyl) ⁇ .
- Rudiphosphite bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tri-tert-butylphenyl) pentaerythritol diphosphite, bis (2 , 4—Jikumi (Rufenil) Penyu erythritol diphosphite, tetra (tridecyl) isopropylidenediphenyldiphosphite, tetra (tridecyl) 1,4,4,1-n-butylidenebis (2-tert-butyl-5-methylphenol) ) Diphosphite, Hexa (tridecyl) -1,1,3-Tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butanetriphosphite, Tetrakis (2,4-di-tert-butylphenyl) biphenylenediphospho
- the above-mentioned phenol-based, zeo-based and phosphorus-based antioxidants may be used alone or as a mixture, and the total is 0.001 to 10 parts by weight, more preferably 0.05, based on 100 parts by weight of the resin. ⁇ 5 parts by weight are used.
- the ultraviolet absorber include, for example, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-14-methoxybenzophenone, 5,5-methylenebis (2-hydroxy-4-methoxybeta).
- 2-hydroxybenzophenones such as benzophenone); 2- (2'-hydroxy-5, -methylphenyl) benzotriazole, 2- (2'-hydroxy-1,3,5'-di-tert-butylphenyl) -5-chloro Benzotriazole, 2- (2,1-hydroxy-3, -tert-butyl-5'-methylphenyl) -1-5-benzobenzotriazole, 2- (2'-hydroxy-5'-tert-octylphenyl) benzot Lyazole, 2- (2, -hydroxy-3,5, dicumylphenyl) benzotriazole, 2- (2'-hydroxy-3'-tert-butyl-5'-potoxyphenyl) 2- (2 '—Hydroxyphenyl) benzotriazoles; phenyl salicylate, resorcinol monobenzoate, 2,4-di-tert-butylphenyl _ 3,5-di-tert-butyl-4-hydroxybenzoate,
- hindered amine compounds include, for example, 2,2,6,6-tetramethyl-4-piberidyl-1-oxy, 2,2,6,6-tetramethyl-4-piberidyl stearate, 1,2,2,6 , 6-Pentamethyl-4-piberidylstearate, 2,2,6,6-tetramethyl-4-piperidylbenzoate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6) , 6-pentyl methyl-4-piperidyl) packet, tetrakis (2,2,6,6-tetramethyl-4-piperidylbutane) tetracarboxylate, Tetrakis (1,2,2,6,6-pentamethyl-1-piperidylbutane) Tetracarpoxylate, bis (2,2,6,6-tetramethyl-1-piperidyl) • di (tridec
- nucleating agent examples include Pt-butyl aluminum benzoate and sodium benzoate.
- Metal salts of aromatic carboxylic acids such as dimethyl; sodium bis (2,4-di-tert-butylphenyl) phosphate, lithium bis (2,4-di-tert-butylphenyl) phosphate, sodium-2,2-methylenebis ( Metal salts of acidic phosphoric acid esters such as 4,6-ditert-butylphenyl) phosphate; polyhydric alcohol derivatives such as dibenzylidene sorbitol and bis (methylbenzylidene) sorbitol.
- the flame retardant examples include halogen-based flame retardants, red phosphorus, melamine phosphate, pyrazine phosphate, guanidine phosphate, melamine pyrophosphate, piperazine pyrophosphate, guanidine pyrophosphate, melamine polyphosphate, melamine polyphosphate, and melamine polyphosphate.
- Phosphorus flame retardants such as guanidine polyphosphate, phosphate ester compounds and phosphazene compounds; nitrogen flame retardants such as melamine cyanurate; metal hydroxides such as magnesium hydroxide and aluminum hydroxide; Examples thereof include inorganic compounds such as antimony trioxide and zinc borate, and anti-drip agents such as polytetrafluoroethylene.
- Hydrate talcites may be natural or synthetic, and can be used with or without surface treatment or with or without crystal water. For example, a basic carbonate represented by the following general formula (IV) can be mentioned.
- M is an alkali metal or zinc
- X is a number from 0 to 6
- y is a number from 0 to 6
- z is a number from 0.1 to 4
- p is a valence of M
- n is Represents the number of water of crystallization from 0 to 100.
- the lubricant include fatty acid amides such as laurylamide, myristylamide, laurylamide, stearylamide, and behenylamide, ethylenebisstearylamide, polyethylene wax, and calcium stearate.
- Metal stones such as magnesium and magnesium stearate, magnesium distearyl phosphate, stearyl phosphorus And the like.
- the filler inorganic substances such as talc, silica, calcium carbonate, glass fiber, potassium titanate, potassium borate, carbon black and carbon fiber, and carbon nanoparticles such as fullerene and carbon nanotube are used in the case of a spherical substance.
- the fiber diameter / fiber length and the aspect ratio are appropriately selected and used. It is preferable to use a filler that has been subjected to a surface treatment as necessary.
- the resin composition containing the hindered amine compound of the present invention is used for an agricultural film, the resin composition may contain an ultraviolet absorbent for controlling the growth of the crop, or an infrared absorbent for improving the heat retention.
- Fog may be generated in the house, or the film surface may be condensed and light may not reach the crop sufficiently.Therefore, even if an antifog agent, antifog agent, Good.
- the hinderdamine compound of the present invention is effective in stabilizing a synthetic resin, and the synthetic resin composition is particularly suitable for agricultural films made of polyolefin, which are exposed to acidic components due to pesticides and sulfur vapor, and for acid rain outdoors. It is suitable for use as exposed paints and sealants.
- the hinderdamine compound of the present invention includes a resin composition, a lubricating oil, and a resin composition containing an acidic component such that a conventional hinderedamine compound cannot exert a sufficient stabilizing effect under the influence of an acidic component such as melamine pyrophosphate. It can be used in applications that require long-term stabilization of organic substances, such as stabilization of liquids such as electrolytes.
- the concentrate was purified by silica gel column chromatography (developing solvent: toluene), and bis (111-decanoxy-1,2,2,6,6-tetramethylpiperidine-14) having a purity of 99.9% according to the above-mentioned analytical method was obtained.
- G Carbonate (55.5% yield) was obtained as a colorless liquid. The analysis results of the obtained compound No. 1 are shown below.
- the compound obtained in Synthesis Example 1 was an intermediate of Compound No. 7 described above, and the compound obtained in Synthesis Example 2 was used in Example 3 as an intermediate of Compound No. 11 described above. .
- Dissolve 10.0 g (57.7 mmo 1) of 4-hydroxy-11-oxy-2,2,6,6-tetramethylpiperidine in 40.O g of benzene A solution prepared by dissolving 54.4 g (49. lmmol) of distearoyl peroxide in 200 g of benzene was added dropwise with C over 2 hours. The reaction solution obtained by reacting at the same temperature for another 3 hours was analyzed by gas chromatography, and the ratio of raw material: stearic acid: target substance was 7.8: 21.9: 70.3. .
- reaction solution was desolvated under reduced pressure, 40 g of hexane was added, 31.6 g (57.7 mmo 1) of a 7.3% aqueous sodium hydroxide solution and 25 g of ethanol were added, and the mixture was stirred at 40 ° C for 30 minutes.
- the resultant was washed by oil-water separation, and further washed twice with 30 g of water to remove lauric acid.
- Anhydrous magnesium sulfate The mixture was dried with a steam, filtered to remove magnesium sulfate, and desolvated under reduced pressure at an evaporator.
- Linear low-density polyethylene resin (Nippon Tunica Co., Ltd .: PES120) 100 parts by weight, calcium stearate 0.05 parts by weight, tetrakis (3- (3,5-di-tert-butyl) 4-hydroxyphenyl) propionyloxymethyl) methane 0.05 parts by weight, tris (2,4-di-tert-butylphenyl) phosphite 0.
- the pellet was pelletized with a single screw extruder at a cylinder temperature of 200 ° C and a screw rotation speed of 25 rpm. It has become.
- the resulting pellets were pressed at 180 press to form a 80 zzm thick film.
- the resulting film was placed in a lmX lmx lm dampoor container, in which 2 g of sulfur was steamed on a hot plate and allowed to stand for 24 hours. After 600 hours, the carbonyl index was measured.
- the carbonyl index is defined as [1 og (IoZI)] / d using infrared absorption spectrum analysis data of the film.
- I o is the transmittance (%) before deterioration at 1710 cm- 1
- I is the transmittance (%) after deterioration
- d is the film thickness (cm)
- Table 2 shows the results.
- Organic solvent-based acrylic paint (Mr. Color Super Clear: GS I Creos Co., Ltd.) 0.5 parts by weight of the hindered amine compound described in Table 3 is added to 100 parts by weight to a film thickness of 50-60 / m The test was applied on an aluminum substrate, and the gloss retention and color difference were measured after 500 hours under conditions of xenon-zeza-ome at 63 ° C with rain (water spray of 18 minutes during 120 minutes). Table 3 shows the results. Hinderdamine compound Gloss retention (%) Color difference
- Example 8-1 Compound No. 1 94 6.79
- a hindered amine compound having a long-term effect of providing weather resistance can be provided.
- a synthetic resin composition having excellent long-term weather resistance, particularly a polyolefin resin composition suitable for agricultural films can be provided.
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Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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JP2006510549A JP4587488B2 (ja) | 2004-03-02 | 2005-02-28 | カーボネート骨格を有する低塩基性ヒンダードアミン化合物を含有する合成樹脂組成物及びそれを含有する塗料組成物。 |
KR1020067017786A KR101135833B1 (ko) | 2004-03-02 | 2005-02-28 | 카보네이트 골격을 가진 저염기성 힌더드 아민 화합물,합성수지 조성물 및 도료 조성물 |
CN2005800066972A CN1926107B (zh) | 2004-03-02 | 2005-02-28 | 具有碳酸酯骨架的弱碱性受阻胺类化合物、合成树脂组合物和涂料组合物 |
EP05720079A EP1731508B1 (en) | 2004-03-02 | 2005-02-28 | Weakly basic hindered amines having carbonate skeletons, synthetic resin compositions, and coating compositions |
US10/591,533 US20090111699A1 (en) | 2004-03-02 | 2005-02-28 | Weakly Basic Hindered Amines Having Carbonate Skeletons, Synthetic Resin Compositions, And Coating Compositions |
US12/753,439 US8329787B2 (en) | 2004-03-02 | 2010-04-02 | Weakly basic hindered amines compounds having carbonate skeletons, synthetic resin compositions and coating compositions |
US13/613,807 US9133121B2 (en) | 2004-03-02 | 2012-09-13 | Weakly basic hindered amines compounds having carbonate skeletons, synthetic resin compositions and coating compositions |
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JP2004057297 | 2004-03-02 | ||
JP2004-057297 | 2004-03-02 |
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US10/591,533 A-371-Of-International US20090111699A1 (en) | 2004-03-02 | 2005-02-28 | Weakly Basic Hindered Amines Having Carbonate Skeletons, Synthetic Resin Compositions, And Coating Compositions |
US12/753,439 Division US8329787B2 (en) | 2004-03-02 | 2010-04-02 | Weakly basic hindered amines compounds having carbonate skeletons, synthetic resin compositions and coating compositions |
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PCT/JP2005/003807 WO2005082852A1 (ja) | 2004-03-02 | 2005-02-28 | カーボネート骨格を有する低塩基性ヒンダードアミン化合物、合成樹脂組成物及び塗料組成物 |
Country Status (6)
Country | Link |
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US (3) | US20090111699A1 (ja) |
EP (1) | EP1731508B1 (ja) |
JP (1) | JP4587488B2 (ja) |
KR (1) | KR101135833B1 (ja) |
CN (1) | CN1926107B (ja) |
WO (1) | WO2005082852A1 (ja) |
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Also Published As
Publication number | Publication date |
---|---|
KR101135833B1 (ko) | 2012-04-16 |
US20130023611A1 (en) | 2013-01-24 |
EP1731508B1 (en) | 2012-08-01 |
US8329787B2 (en) | 2012-12-11 |
US20100190898A1 (en) | 2010-07-29 |
US20090111699A1 (en) | 2009-04-30 |
CN1926107A (zh) | 2007-03-07 |
EP1731508A4 (en) | 2009-10-28 |
KR20060131873A (ko) | 2006-12-20 |
EP1731508A1 (en) | 2006-12-13 |
US9133121B2 (en) | 2015-09-15 |
JPWO2005082852A1 (ja) | 2008-01-17 |
JP4587488B2 (ja) | 2010-11-24 |
CN1926107B (zh) | 2012-01-04 |
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