Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
  • C08G63/16—Dicarboxylic acids and dihydroxy compounds
  • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
  • C08G63/16—Dicarboxylic acids and dihydroxy compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J3/00—Processes of treating or compounding macromolecular substances
  • C08J3/18—Plasticising macromolecular 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
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0016—Plasticisers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L101/00—Compositions of unspecified macromolecular compounds
  • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
  • C08L101/04—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing halogen atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L27/00—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 a halogen; Compositions of derivatives of such polymers
  • C08L27/02—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
  • C08L27/04—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
  • C08L27/06—Homopolymers or copolymers of vinyl chloride
• • 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

Definitions

• the present invention relates to a specific polyester plasticizer and a chlorine-containing resin composition containing the plasticizer, and more particularly, to 2-methyl-1,3-propanediol and 3-methyl-1,5-pentanediol. And a polyester plasticizer obtained by reacting an organic dicarboxylic acid component having adipic acid as an essential component and a terminal terminator, and a chlorine-containing resin composition containing the plasticizer.
• Polyester compounds obtained from aliphatic diols and aliphatic dicarboxylic acids are useful as plasticizers for synthetic resins, and are particularly widely used as plasticizers for chlorine-containing resins such as vinyl chloride resins.
• a polyester plasticizer having improved low-temperature flexibility by using 2-methyl-1,3-propanediol as an aliphatic diol has been reported in Japanese Patent Application Laid-Open No. 61-78827.
• this polyester-based plasticizer has a low plasticizing efficiency and cannot impart sufficient oil resistance to a chlorine-containing resin. Disclosure of the invention
• An object of the present invention is to provide a polyester-based plasticizer which is excellent in plasticization efficiency and can impart excellent oil resistance to a synthetic resin such as a chlorine-containing resin, and a chlorine-containing resin composition containing the polyester-based plasticizer. Is to provide.
• the present invention has been made based on the above-mentioned findings, and 100 mol parts of 2-methyl-1,3-propanediol, and 10 to 100 mol of 3-methyl-1,5-pentendiol are used.
• Diol component consisting of 0 parts and 100 parts by mole of other aliphatic diol
• an organic dicarboxylic acid component comprising 100 mol parts of adipic acid and 100 to 100 mol parts of another organic dicarboxylic acid
• a terminal comprising a monohydric aliphatic alcohol or a monovalent aliphatic organic acid.
• the present invention provides a polyester plasticizer having an average molecular weight of 500 to 5,000, which is obtained by reacting a terminator (c).
• the present invention also provides a chlorine-containing resin composition
• a chlorine-containing resin composition comprising 100 parts by mass of a chlorine-containing resin, 10 to 100 parts by mass of the polyester-based plasticizer, and 0 to 100 parts by mass of other additive components.
• the polyester plasticizer of the present invention comprises: a diol component (a); an organic dicarboxylic acid component.
• the above-mentioned diol component (a) is an aliphatic diol containing 2-methyl-1,3-propanediol and 3-methyl-1,5-pentanediol as essential components and other aliphatic diols as optional components. Consisting of a mixture of
• aliphatic diols described above include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,4-butanediol, Neopentyldaricol, 3-methyl-2,4-pentanediol, 2,4-pentanediol, 1,5-pentanedyl, 2,4-getyl-1,5-pentendiol, 1,6-hexane Examples thereof include diol, 1,7-heptanediol, 3,5-heptanediol, 1,8-octanediol, 2-methyl-1,8-octanediol, 1,9-nonanediol, and 1,10-decanediol.
• the amount of 3-methyl-1,5-pentanediol used in the diol component (a) is 10 to 1,000 mol parts with respect to 100 mol parts of 2-methyl-1,3-propanediol. It is preferably from 200 to 200 mol parts, more preferably from 20 to 100 mol parts. If the amount is less than 10 parts by mole, sufficient low-temperature flexibility cannot be obtained, and if it exceeds 1000 parts by weight, oil resistance deteriorates.
• the amount of other aliphatic diols used in the diol component (a) is The amount is from 0 to 100 mol parts, preferably from 0 to 500 mol parts, more preferably from 0 to 200 mol parts, based on 100 mol parts of chill-1,3-propanediol. If it exceeds 100 parts by mole, excellent plasticization efficiency and oil resistance cannot be obtained.
• organic dicarboxylic acid component (b) contains adipic acid as an essential component and other organic dicarboxylic acids as optional components.
• organic dicarboxylic acids mentioned above include oxalic acid, malonic acid, succinic acid, glucuric acid, pimelic acid, suberic acid, azeline acid, sebacic acid, dodecandioic acid, 2-methylsuccinic acid, 2-methyladipin Aliphatic dicarboxylic acids such as acid, 3-methyladipic acid, 3-methylilepentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid, hydrogenated dimeric acid Aromatic dicarboxylic acids such as acids, phthalic acid, terephthalic acid, isophthalic acid, orthophthalic acid, and naphthalenedicarboxylic acid, 1,2-cyclopentanedicarboxylic acid, 1,3-cyclopentanedicarboxylic acid, 1,2- Cyclohexanedicarboxylic acid, 1,3-cyclohe
• the amount of these other organic carboxylic acids to be used is 0 to 100 mol parts, preferably 0 to 50 mol parts, more preferably 0 to 20 mol parts, per 100 mol parts of adipic acid. I like it. If it exceeds 100 mole parts, excellent plasticization efficiency ⁇ oil resistance cannot be obtained.
• the terminal terminator (c) comprises a monohydric aliphatic alcohol or a monovalent aliphatic organic acid.
• Monohydric aliphatic alcohols include methanol, ethanol, 1-propanol, 2-propanol, butanol, 2-butanol, isobutyl alcohol, tert-butyl alcohol, amyl alcohol, hexanol, isohexanol, and Phenol, 2-hepanol, octanol, isooctanol, 2-ethylhexanol, nonanol, isononanol, decanol, isodecanol, pendanol, isordanol, dodecanol, benzyl alcohol, 2-butyloctanol 2-hexyldecanol, 2-hexyldecanol, 2-hexyldecanol, stearyl alcohol, 2-octyldecanol, 2-hexy
• Examples of monovalent aliphatic organic acids include formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, cabronic acid, force prillic acid, 2-ethylhexanoic acid, pelargonic acid, force purinic acid, neodecanoic acid, pendecane
• Examples include acids, lauric acid, tridecanoic acid, myristic acid, peroxydecanoic acid, palmitic acid, margaric acid, stearic acid, and coconut oil fatty acids, which are used alone or as a mixture of two or more.
• the polyester plasticizer of the present invention obtained by reacting the diol component (a), the organic dicarboxylic acid component (b) and the terminal stopper (c) has an average molecular weight of 500 to 5,000, preferably 500 to 5,000. 3000, more preferably 1000 to 3000. If it is less than 500, problems such as volatility, bleeding and migration occur, and if it is more than 5000, compatibility and flexibility deteriorate.
• the viscosity of the polyester plasticizer of the present invention is not particularly limited, and can be arbitrarily set according to the use or the method of use.
• the viscosity is usually 100 to 5000 mPa's.
• the acid value is preferably 1 or less, and the hydroxyl value is preferably 30 or less.
• the method for producing the polyester plasticizer of the present invention by reacting the diol component (a), the organic dicarboxylic acid component (b) and the terminal stopper (c) is not particularly limited, and is not particularly limited. Can be applied. Examples of the production method include a method of directly condensing a diol and an organic dicarboxylic acid, a method of transesterifying a diol with a lower alkyl ester of an organic carboxylic acid, and a method of condensing a diol with an organic carboxylic acid halide. Can be In the reactions in these production methods, an esterification catalyst may be used, or no catalyst may be used. The terminator (c) is also introduced using a similar esterification reaction. The molar ratio of the diol component (a), the organic dicarboxylic acid component (b) and the terminal stopper (c) is arbitrary, and is set so that the molecular weight is 500 to 5,000.
• esterification catalyst examples include acidic catalysts such as sulfuric acid, phosphoric acid, zinc chloride, benzenesulfonic acid, p-toluenesulfonic acid and 4-chlorobenzenesulfonic acid; tetramethoxytitanium, tetraethoxytitanium, tetraisopropoxytitanium and the like.
• Alcoqui Titanium acylate compounds such as polyhydroxytitanium stearate and polyisopropoxytitanate stearate; titanium acetyl acetate, trieamine noraminate, titanium ammonium lactate, titanium ethyl lactate Titanium chelate compounds such as titanium, titanium octylendalcholate; tin compounds such as dibutyltin diperoxide, dibutyltin oxide, dibutyltin diacetate; metal acetate salts such as magnesium acetate, calcium acetate, zinc acetate; antimony oxide, zirconium oxide And the like, and these are used alone or in combination.
• polyester plasticizer of the present invention other raw materials may be reacted with the diol component (a), the organic dicarboxylic acid component (b) and the terminal stopper (c), if necessary.
• Other raw materials include hydroxy acids such as 12-hydroxystearic acid, (poly) 12-hydroxystearic acid, 4-hydroxybenzoic acid, and poly4-hydroxybenzoic acid; trimethyl-l-ethane, trimethylolpropane, Trihydric or higher alcohol compounds such as hexitols, pentitols, glycerin, polyglycerin, pentaerythritol, dipentyl erythritol, and tetramethylolpropane; and tricarboxylic acids such as trimellitic acid and trimesic acid.
• Other raw materials are preferably used in an amount of 10 mol parts or less based on a total amount of 100 mol parts of the diol component (a), the organic dicarboxylic acid component (
• polyester plasticizer of the present invention is suitably used for synthetic resins, especially chlorine-containing resins.
• the chlorine-containing resin composition of the present invention comprises 100 parts by mass of the chlorine-containing resin, 100 to 100 parts by mass of the above-mentioned polyester plasticizer of the present invention, and 0 to 100 parts by mass of other additive components. Department.
• chlorine-containing resin examples include polyvinyl chloride, chlorinated polyvinyl chloride, polyvinylidene chloride, chlorinated polyethylene, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, and vinyl chloride-propylene copolymer.
• the amount of the polyester-based plasticizer of the present invention may be any range as long as the required flexibility can be imparted depending on the application. Usually, it is 10 to 100 parts by mass.
• the other additive components include a plasticizer other than the polyester plasticizer of the present invention; a diketone compound; an insulating improver; various metal salts; a polyol; an epoxy compound; an organic phosphite compound, a phenolic compound, Well-known general additives such as sulfur antioxidants; ultraviolet absorbers; hindered amine light stabilizers; inorganic stabilizers; fillers; antifog agents; antifog agents; Ingredients.
• a plasticizer other than the polyester plasticizer of the present invention a diketone compound; an insulating improver; various metal salts; a polyol; an epoxy compound; an organic phosphite compound, a phenolic compound,
• Well-known general additives such as sulfur antioxidants; ultraviolet absorbers; hindered amine light stabilizers; inorganic stabilizers; fillers; antifog agents; antifog agents; Ingredients.
• plasticizer other than the polyester-based plasticizer of the present invention examples include dibutyl phthalate, butylhexyl phthalate, diheptyl phthalate, dioctyl phthalate, diisononyl phthalate, diisodecyl phthalate, dilauryl phthalate and dicyl phthalate.
• Phthalic acid plasticizers such as chlorohexyl phthalate and dioctyl terephthalate; adipic acid plasticizers such as dioctyl adipate, diisononyl adipate, diisodecyl adipate, di (butyldiglycol) adipate; tetrahydrophthalic acid plasticizer Agent, azelaic acid plasticizer, sebacic acid plasticizer, stearic acid plasticizer, citric acid plasticizer, trimellitic acid plasticizer, pyromellitic acid plasticizer, biphenylene polycarboxylic acid plasticizer Is mentioned.
• the use amount of these plasticizers is preferably 100 parts by mass or less based on 100 parts by mass of the polyester plasticizer of the present invention.
• the 3-diketone compounds described above include dibenzoylmethane and benzoyl Mouth acetic acid, tribenzoylmethane, 1,3-bis (benzoylacetyl) benzene, or metal salts thereof (lithium, sodium, potassium, calcium, magnesium, barium, zinc, etc.).
• the amount of the / 3-diketone compound used is preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the chlorine-containing resin. If the amount is less than 0.01 part by mass, a sufficient effect of addition cannot be obtained, and if it exceeds 10 parts by mass, not only the effect of addition cannot be obtained, but also the heat resistance may be deteriorated.
• Examples of the insulating improver include amorphous silicates described in JP-A-57-177040, JP-A-5-262943, JP-A-5-179090, JP-A-9-324089 and the like.
• Calcium (hydrate) a composition comprising ⁇ -dicalcium silicate hydrate and calcium hydroxide, silicate of aluminum or alkaline earth metal, and the like.
• amorphous calcium silicate (hydrate) is preferable because of its excellent insulating properties and heat resistance.
• Examples of the amorphous calcium silicate (hydrate) include tobermorite gel, CSH (I) and CSH (II).
• the amount of the amorphous calcium silicate (hydrate) to be used is preferably 0.001 to 3 parts by mass, more preferably 0.01 to 1 part by mass, per 100 parts by mass of the chlorine-containing resin. If the amount is less than 0.001 part by mass, the effect of addition is hardly observed.
• Examples of the various metal salts include metals of organic acids or phenols (Li, Na, K, Ca, Ba, Mg, Sr, Zn, Cd, Sn, Cs, Al, organic S n) Salts and metals of organic phosphoric acids (Li, Na, K, Ca, Ba, Mg, Sr, Cd, Sn, Cs, A and organic Sn) salts, etc.
• the amount is preferably 0.05 to 10 parts by mass with respect to 100 parts by mass of the chlorine-containing resin.
• organic acids used in the metal salt include cabronic acid, caprylic acid, perargonic acid, 2-ethylhexylic acid, capric acid, neodecanoic acid, pendecilenic acid, lauric acid, myristic acid, palmitic acid, Stearic acid, isostearic acid, 12-hydroxystearic acid, chlorostearic acid, 12-ketostearic acid, phenylstearic acid, ricinoleic acid, linoleic acid, linoleic acid, oleic acid, araquinic acid, behenic acid, eric acid , Brassic acid and similar acids, and tallow fatty acids, Mixtures of the above naturally occurring organic acids, such as coconut oil fatty acids, tung oil fatty acids, soybean oil fatty acids, and cottonseed oil fatty acids, benzoic acid, p-tert-butylbenzoic acid, ethyl benzoic acid, isopropyl benzoic acid,
• Examples of the phenols used in the above-mentioned metal salts include phenol, cresol, ethylphenol, cyclohexylphenol, noelphenol, laurylphenol and the like.
• Examples of the organic phosphoric acids used in the above metal salts include mono- or octyl phosphoric acid, mono- or dilauryl phosphoric acid, mono- or distearyl phosphoric acid, mono- or di (nonylphenyl) phosphoric acid, and nonylphenyl phosphonate. Esters and stearyl phosphonate esters.
• organic acid zinc salts and Z or organic acid alkaline earth metal salts are preferred because they are advantageous in terms of anti-coloring property, heat resistance and cost.
• polyols examples include trimethylolpropane, ditrimethylolpropane, pentaerythritol, dipentyl erythryl, polypentyl erythritol, and pentaylerythritol or dipentyl erythritol. , Bis (dipentyl erythritol) adipate, glycerin, tris (2-hydroxyethyl) isocyanurate, sorbitol, mannitol, trehalose and the like.
• epoxy compound examples include epoxidized soybean oil, epoxidized linseed oil, epoxidized tung oil, epoxidized fish oil, epoxidized tallow oil, epoxidized castor oil, and epoxidized safflower oil.
• Oil epoxidized methyl stearate, epoxidized butyl stearate, epoxidized stearate-2-ethylhexyl, epoxidized stearate stearyl ester, epoxidized polybutadiene, tris (epoxypropyl) isocyanurate, epoxidized tall oil fatty acid ester , Epoxidized linseed oil fatty acid ester, vinylcyclohexene geoxide, dicyclohexene geoxide, 3,4-epoxycyclohexene methyl ethoxycyclohexane carboxylate, bisphenol A diglycidide Ether, trimethylolpropane polyglycidyl ether, glycerin polydaricidyl ether Hexanediol polyglycidyl ether, 2,2-dimethyl-1,3-propanediol polydaricidyl ether, hydrogenated bisphenol poly
• organic phosphite compound examples include, for example, triphenyl phosphite, tris (2,4-di-tert-butylphenyl) phosphite, tris (2,5-di-tert-butylphenyl) phosphite, and tris (nonylphenyl) ) Phosphite, tris (dinonylphenyl) phosphite, tris (mono, di-mixed nonylphenyl) phosphite, diphenyl acid phosphite, 2,2'-methylenebis (4,6-di-tert-butylphenyl) octyl Phosphite, diphenyldecyl phosphite, diphenyloctyl phosphite, di (nonylphenyl) phenyl erythritol diphosphite, phenyldiisode
• phenolic antioxidants include, for example, 2,6-ditertiarybutyl-cresol, 2,6-diphenyl4-one-year-old kutadecyloxyphenol, stearyl (3,5-diphenyl Tributyl-4-hydroxyphenyl) propionate, distearyl (3,5-ditert-butyl-4-hydroxybenzyl) phosphonate, tridecyl-3,5-ditert-butyl-4-hydroxybenzylthioacetate, thiomethylenebis [ (3,5-ditert-butyl-4-hydroxyphenyl) propionate], 4,4'-thiobis (6-tert-butyl-m-cresol), 2-octylthio-1,4,6-di (3,5 —Di-tert-butyl-4-hydroxyphenoxy) 1 s-triazine, 2,2′-methylenebis (4-methyl-6-tert-butylphenol), bis [3,3-bis (4-methyl
• sulfur-based antioxidants include, for example, dialkylthiodibution pionates such as dilauryl, dimyristyl, myristylstearyl, and distearyl esters of thiodipropionic acid; and pentaerythritol tetra () 8-dodecylmercapto ⁇ -alkyl mercaptopropionate esters of polyols such as propionate).
• UV absorber examples include, for example, 2,4-dihydroxybenzophenone, 2-hydroxy-14-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, and 2-hydroxy-4 —Tertiary butyl-4 ′ — (2-metachloroethoxyethoxyethoxy) benzophenone, 2,5-hydroxybenzophenones such as 5,5′-methylenebis (2-hydroxy-4-methoxybenzophenone); 2- (2-hydroxy-5-methylphenyl) benzotriazole, 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, 2- (2-hydroxy-3,5-di-tert-butylphenyl) 5_ mouth benzotriazole, 2- (2-hydroxy-3-tert-butyl-5-methylphenyl) -1-benzo-benzotriazole, 2- (2-hydroxy -3-Dodecyl-5-methylphenyl) benzotriazole, 2- (2-hydroxy-13-tert-but
• hindered amine light stabilizers include, for example, 2,2,6,6-tetramethyl-4-piberidyl stearate, 1,2,2,6,6-pentymethyl- 4-piberidyl stearate, 2,2,6,6-tetramethyl-4-piperidyl benzoate, bis (2,2,6,6-tetramethyl-1-piperidyl) sebaguet, bis (1,2 , 2,6,6-Pentamethyl-14-piperidyl) sebagate, bis (1-octoxy-1,2,2,6,6-tetramethyl-14-piperidyl) sebacate, tetrakis (2,2,6,6) —Tetramethyl-4-piperidyl) — 1,2,3,4-butanetetracarboxylate, tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,1,2,3,4-butanetetracarpoxy Rate, screw
• examples of the inorganic stabilizers include hydrotalcite, calcium phosphate, calcium oxide, calcium hydroxide, calcium silicate, magnesium phosphate, magnesium oxide, magnesium hydroxide, aluminum hydroxide, and non-crystalline.
• the above hydrotalcite is, for example, a complex salt compound composed of magnesium and Z or an alkali metal and aluminum or zinc, magnesium and aluminum as represented by the following general formula (I). It may be dehydrated.
• hydrotalcites include higher fatty acids such as stearic acid, higher fatty acid metal salts such as oleic acid metal salts, organic sulfonic acid metal salts such as alkali metal dodecylbenzenesulfonate, higher fatty acid amides, Fatty acid ester or wax etc. It may be coated.
• the above hydrotalcite may be a natural product or a synthetic product.
• the method for synthesizing the synthetic product is disclosed in Japanese Patent Publication No. 46-228, Japanese Patent Publication No. 50-30039, Japanese Patent Publication No. 51-291
• Known methods described in, for example, JP-A-36869, JP-A-61-174270, JP-A-5-179052 and the like can be mentioned.
• the above hydrotalcite can be used without being limited by its crystal structure, crystal particle system and the like.
• filler examples include, for example, calcium carbonate, silica, clay, glass beads, myriki, sericite, glass flake, asbestos, wollastonite, potassium titanate, PMF, gypsum fiber, zonolite, M ⁇ S And phosphor fibers, glass fibers, carbonated fibers, and aramide fibers.
• antifogging agent examples include, for example, polyoxyethylene lauryl ether, polyoxyethylene diaryl stearyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol monopalmitate, polyethylene glycol monostearate, and polyoxyethylene monopalmitate.
• antifog examples include, for example, anionic fluorinated surfactants, cationic fluorinated surfactants, amphoteric fluorinated surfactants, nonionic fluorinated surfactants, and fluorinated oligomers. Fluorine-containing compounds are exemplified.
• stabilizing aid examples include, for example, diphenylthiourea, diphenylurine, anilinodithiotriazine, melamine, benzoic acid, cinnamic acid, p-tert-butylbenzoic acid, and aliphatic organic acids.
• organotin compound examples include laurate, malate, mercapto and maleate polymers of dibutyltin or octyltin.
• additive components in addition to the components exemplified above, if necessary, additive components usually used for chlorine-containing resins, for example, a cross-linking agent, an antistatic agent, a discoloring agent, and a plate-out preventing agent.
• additive components usually used for chlorine-containing resins, for example, a cross-linking agent, an antistatic agent, a discoloring agent, and a plate-out preventing agent.
• the total amount of other additive components used is generally 0 to 100 parts by mass with respect to 100 parts by mass of the chlorine-containing resin.
• Applications of the chlorine-containing resin composition of the present invention containing the polyethylene plasticizer of the present invention include: building materials such as wall materials, floor materials, window frames, and wallpapers; electric wire coating materials; interior and exterior materials for automobiles; Agricultural materials such as tunnels; food packaging materials such as fish such as wraps and trays; and miscellaneous goods such as paints, hoses, pipes, sheets, toys, and gloves.
• the following Production Examples 1 to 3 show examples of the polyester plasticizer of the present invention, and the following Examples 1 to 3 show the polyester plasticizers of the present invention obtained in Production Examples 1 to 3 below, respectively.
• 1 shows an example of the chlorine-containing resin composition of the present invention containing an agent.
• Comparative Production Examples 1 and 2 show examples of polyester plasticizers synthesized without using 3-methyl_1,5-pentenediol. Comparative Examples 1 and 2 below show: The following shows Examples of the chlorine-containing resin composition containing the polyester plasticizer obtained in each of Comparative Production Examples 1 and 2 below.
• a reaction flask was charged with 2.9 mole parts of 2-methyl-1,3-propanediol, 3.0 mole parts of adipic acid, 1 mole part of isononanol, and 0.0005 mole parts of tetraisopropoxytitan, and then under a nitrogen stream. After reacting at 22 O for 8 hours while distilling off the water generated in the above, the mixture is further reacted at a pressure of 4000 Pa and 220 for 1 hour to obtain a polyester plasticizer with an average molecular weight of 1600 and a viscosity of 3000 mPa's. . 4 was obtained.
• Polyvinyl chloride resin (degree of polymerization 1050) 100
• Polyester plasticizer (see Table 1) 50
• polyester-based plasticizer As a polyester-based plasticizer, except that polyester-based plasticizers Nos. 4 and 5 obtained in Comparative Production Examples 1 and 2 were used, a sheet prepared according to the same formulation and method as in Example 1 above was used. A tensile test and an oil resistance test were performed in the same manner as in Example 1 above. Table 1 shows the results. ⁇ table 1 ⁇
• the polyester plasticizer of the present invention has excellent plasticizing efficiency and can impart excellent oil resistance to a synthetic resin, particularly a chlorine-containing resin.

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• Compositions Of Macromolecular Compounds (AREA)
• Polyesters Or Polycarbonates (AREA)

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• 2002
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• 2003
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  • 2003-10-29 US US10/534,381 patent/US7348380B2/en not_active Expired - Lifetime
  • 2003-10-29 EP EP03769967.5A patent/EP1564234B1/en not_active Expired - Lifetime
  • 2003-10-29 WO PCT/JP2003/013857 patent/WO2004041903A1/ja not_active Ceased
  • 2003-11-05 TW TW092130928A patent/TW200424230A/zh not_active IP Right Cessation

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