[go: up one dir, main page]

WO2020075519A1 - Ignifuge, composition ignifuge, composition de résine synthétique et objet moulé - Google Patents

Ignifuge, composition ignifuge, composition de résine synthétique et objet moulé Download PDF

Info

Publication number
WO2020075519A1
WO2020075519A1 PCT/JP2019/037909 JP2019037909W WO2020075519A1 WO 2020075519 A1 WO2020075519 A1 WO 2020075519A1 JP 2019037909 W JP2019037909 W JP 2019037909W WO 2020075519 A1 WO2020075519 A1 WO 2020075519A1
Authority
WO
WIPO (PCT)
Prior art keywords
flame retardant
synthetic resin
group
present
mass
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2019/037909
Other languages
English (en)
Japanese (ja)
Inventor
秀明 行武
龍 片桐
井上　智之
佐藤　文彦
総夫 中村
勉 梅木
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Adeka Corp
Original Assignee
Adeka Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Adeka Corp filed Critical Adeka Corp
Publication of WO2020075519A1 publication Critical patent/WO2020075519A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
    • C08L85/02—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus

Definitions

  • the present invention relates to a flame retardant containing a pentaerythritol phosphonate polymer having a specific structure and a synthetic resin composition containing the flame retardant.
  • synthetic resins have been widely used for automobile parts, packaging materials, building materials, agricultural materials, home appliances, toys, etc. due to their excellent chemical and mechanical properties.
  • synthetic resins polypropylene resin, polyethylene resin, polyester resin, polycarbonate resin, ABS resin, styrene resin, polyamide resin, polyphenylene oxide resin and the like are widely used due to their physical properties.
  • synthetic resins are flammable, flame retardancy to flame is required in addition to chemical and mechanical properties for use in the above applications.
  • halogen-based flame retardants As a flame retardant method for synthetic resins, halogen-based flame retardants, inorganic phosphorous flame retardants represented by polyphosphoric acid flame retardants such as red phosphorus and ammonium polyphosphate, and metal hydroxides such as magnesium hydroxide and aluminum hydroxide. It is widely known that physical flame retardants, organic phosphorus flame retardants represented by triaryl phosphate ester compounds, and antimony oxide and melamine compounds used alone or in combination as flame retardant aids.
  • halogen-based flame retardants have safety problems such as generating a large amount of corrosive gas during molding and combustion, and inorganic phosphorus-based flame retardants have toxic gas during combustion, water resistance and heat resistance. Since this is inferior, there is a problem in handling during processing and moldability. Further, the metal hydroxide flame retardant needs to be added in a large amount in order to obtain sufficient flame retardancy, and there is a problem that the original physical properties of the synthetic resin are lost.
  • Organic phosphoric acid flame retardants are also widely known as halogen-free flame retardants, but the heat resistance of the synthetic resin composition is reduced, and the heat resistance of the flame retardant itself is low, which causes problems in handling during processing. there were.
  • An object of the present invention is to provide a novel flame retardant having excellent heat resistance equal to or higher than that of a conventionally used flame retardant, and capable of imparting good flame retardancy to a synthetic resin. .
  • R 1 and R 3 each independently represent a monovalent aromatic group which may have one or more substituents
  • X 1 and X 2 each independently represent a direct bond, an alkylene group having 1 to 8 carbon atoms, an oxygen atom, a nitrogen atom or a sulfur atom, and are optionally adjacent to each other in the alkylene group having 1 to 8 carbon atoms.
  • Oxygen atom, nitrogen atom or sulfur atom may be present between carbon atoms
  • R 2 represents —CH 2 CH 2 — or —CH 2 CH 2 CH 2 —
  • n represents a number of 1 to 10000.
  • R 1 and R 3 are each independently a monocyclic aromatic hydrocarbon ring group, The flame retardant according to the invention 1.
  • a flame retardant composition comprising the flame retardant according to invention 1 and a phosphate compound.
  • invention 7 A synthetic resin composition containing a synthetic resin and 0.01 to 50 parts by mass of the flame retardant of any one of Inventions 1 to 3 with respect to 100 parts by mass of the synthetic resin.
  • invention 8 A synthetic resin composition containing 0.01 to 100 parts by mass of the flame retardant composition according to any one of Inventions 4 to 6 with respect to 100 parts by mass of the synthetic resin.
  • invention 9 9. The synthetic resin composition according to the invention 7 or 8, wherein the synthetic resin contains at least one selected from the group consisting of polyester resins and polyamide resins.
  • a method for flame-retarding a synthetic resin comprising adding a compound represented by the following general formula (1) to the synthetic resin.
  • R 1 and R 3 each independently represent a monovalent aromatic group which may have one or more substituents
  • X 1 and X 2 each independently represent a direct bond, an alkylene group having 1 to 8 carbon atoms, an oxygen atom, a nitrogen atom or a sulfur atom, and are optionally adjacent to each other in the alkylene group having 1 to 8 carbon atoms.
  • Oxygen atom, nitrogen atom or sulfur atom may be present between carbon atoms
  • R 2 represents —CH 2 CH 2 — or —CH 2 CH 2 CH 2 —
  • n represents a number of 1 to 10000.
  • the flame retardant of the present invention has excellent heat resistance, and when added to a synthetic resin, particularly a polyester resin, the flame retardancy of the synthetic resin can be significantly improved.
  • the flame retardant of the present invention contains at least one compound represented by the following general formula (1).
  • R 1 and R 3 each independently represent a monovalent aromatic group which may have one or more substituents
  • X 1 and X 2 each independently represent a direct bond, an alkylene group having 1 to 8 carbon atoms, an oxygen atom, a nitrogen atom or a sulfur atom, and are optionally adjacent to each other in the alkylene group having 1 to 8 carbon atoms.
  • Oxygen atom, nitrogen atom or sulfur atom may be present between carbon atoms
  • R 2 represents —CH 2 CH 2 — or —CH 2 CH 2 CH 2 —
  • n represents a number of 1 to 10000.
  • Examples of the monovalent aromatic group represented by R 1 and R 3 in the general formula (1) include an aromatic hydrocarbon ring group having 6 to 20 carbon atoms and an aromatic hydrocarbon group having 3 to 20 carbon atoms. Heterocyclic groups are mentioned.
  • the aromatic hydrocarbon ring group having 6 to 20 carbon atoms may be a single ring or a condensed ring.
  • Examples of the monocyclic aromatic hydrocarbon ring group include a phenyl group, a biphenyl group and a terphenyl group.
  • Examples of the condensed ring aromatic hydrocarbon ring group include a naphthyl group, a fluoryl group and a pyrenyl group.
  • aromatic heterocyclic group having 3 to 20 carbon atoms examples include furanyl group, thiophenyl group, chromenyl group, benzothiophenyl group, bifuranyl group, terfuranyl group, bithiophenyl group, terthiophenyl group, selenophenyl group, and biphenyl group. Examples thereof include a selenophenyl group and a terselenophenyl group.
  • R 1 and R 3 are preferably aromatic hydrocarbon ring groups having 6 to 20 carbon atoms from the viewpoint of flame retardancy and compatibility with resins, and monocyclic aromatic hydrocarbon groups are preferred.
  • a hydrogen ring group is more preferred, and a phenyl group is even more preferred.
  • the aromatic group preferably has 6 to 10 carbon atoms.
  • examples of the substituent include an alkyl group having 1 to 8 carbon atoms and an alkoxy group having 1 to 8 carbon atoms.
  • the alkyl group having 1 to 8 carbon atoms may be chain-like or cyclic.
  • the chain alkyl group may be linear or branched. Examples of the linear alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, an amyl group, a hexyl group and a 1-octyl group.
  • Examples of the branched alkyl group include an iso-propyl group, a sec-butyl group, a tert-butyl group, an iso-butyl group, an iso-amyl group, a tert-amyl group, a 2-hexyl group, a 3-hexyl group, Examples thereof include a 2-heptyl group, a 3-heptyl group, an iso-heptyl group, a tert-heptyl group, an iso-octyl group and a tert-octyl group.
  • Examples of the cyclic alkyl group include a cyclohexyl group and a 1-methylcyclohexyl group.
  • a linear alkyl group is preferable as the substituent from the viewpoint of flame retardancy and resin compatibility.
  • the linear alkyl group preferably has 1 to 4 carbon atoms, and more preferably 1 or a methyl group.
  • R 1 and / or R 3 in the general formula (1) is a phenyl group and the phenyl group is substituted with one of the above alkyl groups
  • the substitution position of the alkyl group is an ortho position, a meta position and Any of the para positions may be used, and the para position is particularly preferable.
  • R 1 and / or R 3 in the general formula (1) is a phenyl group and the phenyl group is substituted with two alkyl groups as described above, the substituted position of the alkyl group is ortho, meta and It may be in any of the para positions, and the meta position is particularly preferable.
  • Examples of the alkoxy group having 1 to 8 carbon atoms include a group in which an oxygen atom is bonded to the terminal of the alkyl group having 1 to 8 carbon atoms.
  • R 1 and / or R 3 in the general formula (1) is a phenyl group and the phenyl group is substituted with one of the above alkoxy groups
  • the substitution position of the alkoxy group is an ortho position, a meta position or a para position. Any of the positions may be used, and the para position is particularly preferable.
  • R 1 and / or R 3 in the general formula (1) is a phenyl group and the phenyl group is substituted with two alkoxy groups as described above, the substitution position of the alkoxy group is an ortho position, a meta position or It may be in any of the para positions, and the meta position is particularly preferable.
  • the alkylene group having 1 to 8 carbon atoms represented by X 1 and X 2 may be linear or branched.
  • Specific examples of the alkylene group include, for example, methylene group, ethylene group, propylene group, trimethylene group, tetramethylene group, 1,3-butanediyl group, 2-methyl-1,3-propanediyl group, 2-methyl- 1,3-butanediyl group, 2,4-pentanediyl group, 1,4-pentanediyl group, 3-methyl-1,4-butanediyl group, 2-methyl-1,4-pentanediyl group, pentamethylene group, hexamethylene group , Heptamethylene group, octamethylene group and the like.
  • the alkylene group is preferably an alkylene group having 1 to 6 carbon atoms, more preferably an alkylene group having 1 to 4 carbon atoms, and an alkylene group having 1 carbon atom, from the viewpoint of flame retardancy and compatibility with resins. Particularly preferred is methylene.
  • oxygen atom, a nitrogen atom or a sulfur atom may be present between any adjacent carbon atoms in the alkylene group.
  • oxygen atom, nitrogen atom or sulfur atom is selected from oxygen atom, nitrogen atom or sulfur atom at one or more positions of the alkylene group, provided that oxygen atom, nitrogen atom or sulfur atom are not adjacent to each other. There may be one or more types of heteroatoms interposed.
  • R 1 is a phenyl group and X 1 is a methylene group, that is, R 1 and X 1 form a benzyl group.
  • R 3 is a phenyl group and X 2 is a methylene group, that is, R 3 and X 2 form a benzyl group. preferable.
  • R 2 in the general formula (2) represents —CH 2 CH 2 — or —CH 2 CH 2 CH 2 —. From the viewpoint of heat resistance, R 2 is preferably —CH 2 CH 2 —.
  • n represents a number of 1 to 10000, preferably 3 to 10000, more preferably 5 to 10000, and 10 to 10000 is heat resistance, flame retardancy and compatibility.
  • the flame retardant of the present invention may be composed of only a single compound in which n is one type, or may be a mixture of compounds in which n is two or more different types.
  • the number of n may be represented by an average value (based on the number of moles).
  • n in the compound represented by the general formula (1) contained in the flame retardant of the present invention can be measured, for example, by gel permeation chromatography (GPC) or nuclear magnetic resonance analysis (NMR).
  • the compound represented by the general formula (1) contained in the flame retardant of the present invention can be produced by a method similar to the known method for producing pentaerythritol phosphonate.
  • a compound represented by the following general formula (A) and a compound represented by the general formula (B-1) or (B-2) are used as starting materials, and these are heated in a solvent under heating. The reaction is carried out and the polymerization is carried out.
  • the solvent for example, toluene, xylene, monochlorobenzene, dichlorobenzene, propylene carbonate, ethylene carbonate, sulfolane, diglyme or the like can be used.
  • the compound represented by the general formula (C) may be added to the reaction system.
  • R a and R b are each independently a methyl group, an ethyl group, a propyl group, an iso-propyl group, a butyl group, a sec-butyl group, a tert-butyl group, an iso-butyl group, or the like. Represents an alkyl group having 1 to 4 carbon atoms.
  • Y a represents a halogen atom such as chlorine, bromine and iodine.
  • Y a represents a halogen atom such as chlorine, bromine and iodine.
  • R C represents the same group as R 1 and R 3 in formula (1), and represents a monovalent aromatic group which may have one or more substituents.
  • X a represents the same group as X 1 and X 2 in the general formula (1), and represents an alkylene group having 1 to 8 carbon atoms.
  • Y b represents a halogen atom such as chlorine, bromine and iodine.
  • Examples of the compound of the present invention represented by the general formula (1) used as a flame retardant include the following No. 1 to No. Although the compound group represented by 4 is mentioned, it is not particularly limited to these and derivatives thereof can also be used as long as they are represented by the general formula (1). Among these, No. 1 is preferable in terms of heat resistance and flame retardancy. Compound 1 is preferred.
  • n represents a number of 1 to 10000.
  • n represents a number from 1 to 10,000.
  • n represents a number from 1 to 10000.
  • n represents a number from 1 to 10000.
  • the flame retardant of the present invention may consist of only one type of compound represented by general formula (1), or may contain two or more types.
  • the flame retardant composition of the present invention contains a compound represented by the above general formula (1) and a phosphate compound.
  • the flame retardant composition of the present invention can impart excellent flame retardancy to synthetic resins.
  • the flame retardant composition of the present invention may contain only one type of the compound represented by the above general formula (1) or may contain two or more types thereof.
  • Examples of the phosphate compound used in the flame retardant composition of the present invention include phosphates such as melamine phosphate and piperazine phosphate; polyphosphates such as ammonium polyphosphate, melamine polyphosphate and piperazine polyphosphate; ortholine. Orthophosphates such as melamine acid and piperazine orthophosphate; pyrophosphate salts such as ammonium pyrophosphate, melamine pyrophosphate and piperazine pyrophosphate; calcium phosphate; magnesium phosphate and derivatives thereof.
  • the flame retardant composition of the present invention may contain only one kind of these phosphate compounds or may contain two or more kinds thereof.
  • the phosphate compound used in the flame retardant composition of the present invention preferably contains a pyrophosphate from the viewpoint of flame retardancy and processability.
  • the mass ratio of the compound represented by the general formula (1) and the phosphate compound is 9: 1 to 1: 1 in terms of the former: the latter from the viewpoint of flame retardancy. 9 is preferred, 8: 2 to 2: 8 is more preferred, 7: 3 to 3: 7 is even more preferred, and 5: 5 is most preferred.
  • the flame retardant composition of the present invention can be suitably used as a flame retardant for imparting flame retardancy to synthetic resins.
  • the flame retardant composition of the present invention may contain other additives in addition to the compound represented by the general formula (1) and the phosphate compound.
  • the other additives include, for example, phenolic antioxidants, phosphorus antioxidants, thioether antioxidants, other antioxidants, hindered amine light stabilizers, ultraviolet absorbers, plasticizers, and nucleating agents.
  • the flame retardant of the present invention one or more selected from flame retardants, flame retardant aids, lubricants, fillers, hydrotalcites, metal soaps, antistatic agents, pigments and dyes are used.
  • These other additives may be blended directly into the flame retardant composition, or when blended into the synthetic resin, they may be blended into the synthetic resin separately from the flame retardant composition.
  • phenolic antioxidant examples include 2,6-di-tert-butyl-p-cresol, 2,6-diphenyl-4-octadecyloxyphenol, stearyl (3,5-di-tert-butyl-4-).
  • phenolic antioxidants may be used alone or in combination of two or more.
  • the content of the phenolic antioxidant in the flame retardant composition of the present invention can be within the range that does not impair the effects of the present invention, but is included in the synthetic resin composition containing the flame retardant composition of the present invention.
  • the amount is preferably 0.01 to 1 part by mass, more preferably 0.03 to 0.8 part by mass, based on 100 parts by mass of the synthetic resin.
  • Examples of the phosphorus-based antioxidant include triphenyl phosphite, diisooctyl phosphite, heptakis (dipropylene glycol) triphosphite, triisodecyl phosphite, diphenylisooctyl phosphite, diisooctyl phenyl phosphite, Diphenyl tridecyl phosphite, triisooctyl phosphite, trilauryl phosphite, diphenyl phosphite, tris (dipropylene glycol) phosphite, diisodecyl pentaerythritol diphosphite, dioleyl hydrogen phosphite, trilauryl trithiophosphite, Bis (tridecyl) phosphite, tris (isodecyl) phosphi
  • phosphorus-based antioxidants may be used alone or in combination of two or more.
  • the content of the phosphorus-based antioxidant in the flame retardant composition of the present invention can be within the range that does not impair the effects of the present invention, but is included in the synthetic resin composition containing the flame retardant composition of the present invention.
  • the amount is preferably 0.01 to 1 part by mass, more preferably 0.03 to 0.8 part by mass, based on 100 parts by mass of the synthetic resin.
  • thioether antioxidant examples include tetrakis [methylene-3- (laurylthio) propionate] methane, bis (methyl-4- [3-n-alkyl (C12 / C14) thiopropionyloxy] 5-tert-butyl.
  • Phenyl) sulfide ditridecyl-3,3'-thiodipropionate, dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, distearyl-3,3'-thiodipronate Pionate, lauryl / stearyl thiodipropionate, 4,4′-thiobis (6-tert-butyl-m-cresol), 2,2′-thiobis (6-tert-butyl-p-cresol), distearyl- Disulfide can be mentioned.
  • These thioether antioxidants may be used alone or in combination of two or more.
  • the content of the thioether-based antioxidant in the flame retardant composition of the present invention can be within the range that does not impair the effects of the present invention, but is included in the synthetic resin composition containing the flame retardant composition of the present invention.
  • the amount is preferably 0.001 to 10 parts by mass, and more preferably 0.005 to 5 parts by mass, based on 100 parts by mass of the synthetic resin.
  • hindered amine light stabilizers examples include 2,2,6,6-tetramethyl-4-piperidyl stearate, 1,2,2,6,6-pentamethyl-4-piperidyl stearate, 2,2,2. 6,6-Tetramethyl-4-piperidyl benzoate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1 , 2,3,4-butanetetracarboxylate, tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, bis (2,2,2 6,6-Tetramethyl-4-piperidyl) -di (tridecyl) -1,2,3,4-butanetetracarboxylate, bis (1,2,2,6,6-pentamethyl- -Piperidyl) -di (tridec)
  • These hindered amine light stabilizers may be used alone or in combination of two or more.
  • the content of these hindered amine-based light stabilizers can be set within a range that does not impair the effects of the present invention, but with respect to 100 parts by mass of the synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention. Therefore, the amount of 0.001 to 10 parts by mass is preferable, and the amount of 0.005 to 1 part by mass is more preferable.
  • Examples of the ultraviolet absorber include 2-hydroxybenzophenones such as 2,4-dihydroxybenzophenone and 5,5′-methylenebis (2-hydroxy-4-methoxybenzophenone); 2- (2-hydroxy-5-methyl) Phenyl) benzotriazole, 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, 2- (2-hydroxy-3,5-di-tert-butylphenyl) -5-chlorobenzotriazole, 2- ( 2-Hydroxy-3-tert-butyl-5-methylphenyl) -5-chlorobenzotriazole, 2- (2-hydroxy-3,5-dicumylphenyl) benzotriazole, 2,2'-methylenebis (4-tert) -Octyl-6-benzotriazolylphenol), 2- (2-hydr) Polyethylene glycol ester of xy-3-tert-butyl-5-carboxyphenyl) benzotriazole, 2- [2-hydroxy-3- (2
  • ultraviolet absorbers may be used alone or in combination of two or more.
  • the content of the ultraviolet absorber in the flame retardant composition of the present invention can be within a range that does not impair the effects of the present invention, but a synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention
  • the amount is preferably 0.001 to 10 parts by mass, more preferably 0.005 to 1 part by mass, relative to 100 parts by mass.
  • plasticizer examples include phthalate plasticizers such as dibutyl phthalate, butylhexyl phthalate, diheptyl phthalate, di- (2-ethylhexyl) phthalate, diisononyl phthalate, diisodecyl phthalate, dilauryl phthalate, dicyclohexyl phthalate, dioctyl terephthalate; Adipate plasticizers such as dioctyl adipate, diisononyl adipate, diisodecyl adipate, di (butyl diglycol) adipate; triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, tri (isopropylphenyl) phosphate, triethyl phosphate, tributyl phosphate, Trioctyl phosphate, tri (butoxyethyl) phosphate, o
  • Preferred examples include polyester plasticizers other than the present invention, phthalate plasticizers, trimellitate plasticizers, adipate plasticizers, sebacic acid plasticizers, and epoxy plasticizers. These plasticizers may be used alone or in combination of two or more.
  • the content of the plasticizer in the flame retardant composition of the present invention can be set within a range that does not impair the effects of the present invention, but the synthetic resin 100 contained in the synthetic resin composition containing the flame retardant composition of the present invention An amount of 1 to 90 parts by mass is preferable, and an amount of 10 to 80 parts by mass is more preferable.
  • nucleating agent examples include carboxylic acids such as sodium benzoate, 4-tert-butylbenzoic acid aluminum salt, sodium adipate and disodium bicyclo [2.2.1] heptane-2,3-dicarboxylate.
  • Metal salts sodium bis (4-tert-butylphenyl) phosphate, sodium-2,2'-methylenebis (4,6-di-tert-butylphenyl) phosphate and lithium-2,2'-methylenebis (4,6-) Phosphoric acid ester metal salts such as di-tert-butylphenyl) phosphate, dibenzylidene sorbitol, bis (methylbenzylidene) sorbitol, bis (p-ethylbenzylidene) sorbitol, and polyhydric alcohol derivatives such as bis (dimethylbenzylidene) sorbitol, N, N ', N " Tris [2-methylcyclohexyl] -1,2,3-propanetricarboxamide (RIKACLEAR PC1), N, N ', N "-tricyclohexyl-1,3,5-benzenetricarboxamide, N, N'-dicyclohexyl- Examples thereof include amide
  • nucleating agents may be used alone or in combination of two or more.
  • the content of the nucleating agent in the flame retardant composition of the present invention can be within the range that does not impair the effects of the present invention, but a synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention
  • the amount is preferably 1 to 90 parts by mass, more preferably 10 to 80 parts by mass, based on 100 parts by mass.
  • Examples of the other flame retardant include, for example, triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate, cresyl-2,6-dixylenyl phosphate, resorcinol bis (diphenyl phosphate), (1- Methylethylidene) -4,1-phenylenetetraphenyldiphosphate, 1,3-phenylenetetrakis (2,6-dimethylphenyl) phosphate, trade names "ADEKA STAB FP-500", "ADEKA STAB FP-600” manufactured by ADEKA CORPORATION.
  • phosphorus-based flame retardants such as phosphorus-based flame retardants, magnesium hydroxide, metal hydroxides such as aluminum hydroxide, brominated bisphenol A type epoxy resin, brominated phenol novolac type epoxy resin, hexabromobenzene, pentabromotoluene, ethylene bis (pentabromo) Phen
  • These flame retardants may be used alone or in combination of two or more.
  • the content of these flame retardants in the flame retardant composition of the present invention can be within the range that does not impair the effects of the present invention, a synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention
  • the amount is preferably 1 to 90 parts by mass, more preferably 3 to 80 parts by mass, based on 100 parts by mass.
  • the above flame retardant aids include inorganic flame retardant aids and organic flame retardant aids.
  • the inorganic flame retardant aids include inorganic compounds such as titanium oxide, aluminum oxide, magnesium oxide, hydrotalcite, talc, and montmorillonite, and surface-treated products thereof.
  • TIPAQUE R-680 titanium oxide : Ishihara Sangyo Co., Ltd.
  • Kyowamag 150 magnesium oxide: Kyowa Chemical Industry Co., Ltd.
  • DHT-4A hydrotalcite: Kyowa Chemical Industry Co., Ltd.
  • Alcamizer 4 zinc-modified hydrotalcite
  • organic flame retardant aid examples include pentaerythritol, dipentaerythritol, and the like. These flame retardant aids may be used alone or in combination of two or more.
  • the content of the flame retardant aid in the flame retardant composition of the present invention can be set within a range that does not impair the effects of the present invention, but the synthetic resin composition containing the flame retardant composition of the present invention contains a synthetic resin composition.
  • the amount is preferably 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, based on 100 parts by mass of the resin.
  • the lubricant examples include unsaturated fatty acid amides such as oleic acid amide and erucic acid amide; saturated fatty acid amides such as behenic acid amide and stearic acid amide, butyl stearate, stearyl alcohol, stearic acid monoglyceride, sorbitan monopalmititate. , Sorbitan monostearate, mannitol, stearic acid, hydrogenated castor oil, stearic acid amide, oleic acid amide, ethylenebisstearic acid amide and the like. These lubricants may be used alone or in combination of two or more.
  • the content of the lubricant in the flame retardant composition of the present invention can be set within a range that does not impair the effects of the present invention, but 100 mass of the synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention. An amount of 0.01 to 10 parts by mass is preferable, and an amount of 0.03 to 1 part by mass is more preferable.
  • the filler examples include talc, mica, calcium carbonate, calcium oxide, calcium hydroxide, magnesium carbonate, magnesium hydroxide, magnesium oxide, magnesium sulfate, aluminum hydroxide, barium sulfate, glass powder, glass fiber, clay, Dolomite, mica, silica, alumina, potassium titanate whiskers, wollastonite, fibrous magnesium oxysulfate, etc. can be mentioned, and the particle diameter (fiber diameter or fiber length and aspect ratio in the fibrous state) is appropriately selected and used. be able to.
  • the filler may be surface-treated if necessary. These fillers may be used alone or in combination of two or more.
  • the content of the filler in the flame retardant composition of the present invention can be set within a range that does not impair the effects of the present invention, but the synthetic resin 100 included in the synthetic resin composition containing the flame retardant composition of the present invention An amount of 0.01 to 90 parts by mass is preferable, an amount of 0.1 to 50 parts by mass is more preferable, and an amount of 5 to 40 parts by mass is further preferable.
  • the content of the glass fiber is 100 parts by mass of the synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention from the viewpoint of processability.
  • an amount of 10 to 40 parts by mass is preferable.
  • hydrotalcites are complex salt compounds composed of magnesium, aluminum, hydroxyl group, carbonic acid group and arbitrary crystal water known as natural products or synthetic products, and a part of magnesium or aluminum is alkali metal or zinc. Examples thereof include those substituted with other metals and those substituted with hydroxyl groups and carbonic acid groups with other anion groups.
  • the metal of hydrotalcite represented by the following general formula (2) is alkali. The thing substituted with the metal is mentioned.
  • water of crystallization may be dehydrated, higher fatty acids such as stearic acid, higher fatty acid metal salts such as oleic acid alkali metal salts, organic sulfonic acid metal salts such as dodecylbenzenesulfonic acid alkali metal salts, higher fatty acids. It may be coated with amide, higher fatty acid ester or wax. These may be natural products or synthetic products, and can be used without being limited by the crystal structure, crystal particles and the like. These hydrotalcites may be used alone or in combination of two or more.
  • the content of hydrotalcites in the flame retardant composition of the present invention can be set within a range that does not impair the effects of the present invention, but is not limited to the synthetic resin composition containing the flame retardant composition of the present invention.
  • the amount is preferably 0.01 to 90 parts by mass, more preferably 0.1 to 50 parts by mass, still more preferably 5 to 40 parts by mass, based on 100 parts by mass of the resin.
  • the metal soap examples include salts of metals such as magnesium, calcium, aluminum and zinc and saturated or unsaturated fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid and oleic acid. These metal soaps may be used alone or in combination of two or more.
  • the content of the metal soap in the flame retardant composition of the present invention can be blended within a range that does not impair the effects of the present invention, but a synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention The amount is preferably 0.001 to 10 parts by mass, more preferably 0.01 to 5 parts by mass, based on 100 parts by mass.
  • antistatic agent examples include cationic antistatic agents such as fatty acid quaternary ammonium ion salt and polyamine quaternary salt; higher alcohol phosphate ester salt, higher alcohol EO adduct, polyethylene glycol fatty acid ester, anionic alkyl Anionic antistatic agents such as sulfonates, higher alcohol sulfuric acid ester salts, higher alcohol ethylene oxide adduct sulfuric acid ester salts, and higher alcohol ethylene oxide adduct phosphoric acid ester salts; polyhydric alcohol fatty acid esters, polyglycol phosphoric acid esters, polyoxy Nonionic antistatic agents such as ethylene alkyl allyl ether; amphoteric alkyl betaines such as alkyldimethylaminoacetic acid betaine; amphoteric antistatic agents such as imidazoline type amphoteric active agents.
  • cationic antistatic agents such as fatty acid quaternary ammonium ion salt and polyamine quaternary salt
  • antistatic agents may be used alone or in combination of two or more.
  • the content of the antistatic agent in the flame retardant composition of the present invention can be within the range that does not impair the effects of the present invention, but a synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention
  • the amount is preferably 0.01 to 20 parts by mass, more preferably 0.03 to 10 parts by mass, relative to 100 parts by mass.
  • a commercially available pigment may be used, and for example, Pigment Red 1, 2, 3, 9, 10, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86.
  • Pigment Green 7, 10, 36 Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 and the like.
  • Pigment Green 7, 10, 36 Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 and the like.
  • These pigments may be used alone or in combination of two or more.
  • the content of the pigment in the flame retardant composition of the present invention can be set within a range that does not impair the effects of the present invention, but 100 mass% of the synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention.
  • the amount is preferably 0.001 to 5 parts by mass, and more preferably 0.003 to 3 parts by mass with respect to parts.
  • the dyes include azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes, stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes. , Dyes such as phthalocyanine dyes and cyanine dyes. These dyes may be used alone or in combination of two or more.
  • the content of the pigment in the flame retardant composition of the present invention can be set within a range that does not impair the effects of the present invention, but 100 mass% of the synthetic resin contained in the synthetic resin composition containing the flame retardant composition of the present invention.
  • the amount is preferably 0.001 to 5 parts by mass, and more preferably 0.003 to 3 parts by mass with respect to parts.
  • the synthetic resin composition of the present invention comprises a synthetic resin and the flame retardant of the present invention.
  • the content of the flame retardant of the present invention in the synthetic resin composition of the present invention is 0.01 to 50 parts by mass with respect to 100 parts by mass of the synthetic resin, and from the viewpoint of flame retardancy, it is preferably 0.05 to The amount is 45 parts by mass, more preferably 1 to 30 parts by mass. If the content of the flame retardant of the present invention is less than 0.01 parts by mass, the flame retardant effect may be insufficient, and if it is more than 50 parts by mass, the physical properties of the synthetic resin may be impaired.
  • the synthetic resin composition of the present invention contains a synthetic resin and the flame retardant composition of the present invention.
  • the content of the flame retardant composition of the present invention in the synthetic resin composition of the present invention is 0.01 to 100 parts by mass with respect to 100 parts by mass of the synthetic resin, and preferably 0.05 from the viewpoint of flame retardancy. To 95 parts by mass, more preferably 1 to 90 parts by mass. If the blending amount of the flame retardant composition of the present invention is less than 0.01 parts by mass, the flame retarding effect may be insufficient, and if it is more than 100 parts by mass, the physical properties of the synthetic resin may be impaired.
  • thermoplastic resin examples include polyvinyl chloride resin, polyethylene resin, polypropylene resin, polystyrene resin, polyvinyl acetate resin, polyurethane resin, cellulosic resin, acrylic resin, AS (acrylonitrile-styrene) resin, ABS (acrylonitrile-butadiene).
  • -Styrene resin fluorine resin, thermoplastic elastomer, polyamide resin, polyacetal resin, polycarbonate resin, modified polyphenylene ether resin, polyester resin (polyethylene terephthalate resin, polybutylene terephthalate resin, polylactic acid resin), cyclic polyolefin resin , Polyphenylene sulfide resin and the like.
  • These synthetic resins may be used alone or in combination of two or more kinds.
  • a polyester resin or a polyamide resin is preferable, a polyester resin is more preferable, and a polybutylene terephthalate resin (PBT resin) is particularly preferable.
  • polyester resin a divalent acid such as terephthalic acid as an acid component, or a derivative thereof having an ester forming ability is used, a glycol having 2 to 10 carbon atoms as a glycol component, another divalent alcohol, or Examples thereof include saturated polyester resins obtained by using such derivatives having ester forming ability.
  • polyalkylene terephthalate resin is preferable.
  • Specific examples of the polyalkylene terephthalate resin include polyethylene terephthalate resin, polybutylene terephthalate resin, and polyhexamethylene terephthalate resin.
  • polyamide resin examples include aliphatic polyamides such as polyamide 46, polyamide 6, polyamide 66, polyamide 610, polyamide 612, polyamide 11 and polyamide 12; alicyclic rings such as bis (aminocyclohexyl) C 1-3 alkanes.
  • Alicyclic polyamides obtained from aromatic diamines and aliphatic dicarboxylic acids such as C 8-14 alkanedicarboxylic acids; aromatic dicarboxylic acids (eg terephthalic acid and / or isophthalic acid) and aliphatic diamines (eg hexamethylenediamine) , Nonamethylenediamine, etc.); polyamides obtained from aromatic and aliphatic dicarboxylic acids (eg, terephthalic acid and adipic acid) and aliphatic diamines (eg, hexamethylenediamine), and the like.
  • aromatic dicarboxylic acids eg terephthalic acid and / or isophthalic acid
  • aliphatic diamines eg hexamethylenediamine
  • polyamides obtained from aromatic and aliphatic dicarboxylic acids eg, terephthalic acid and adipic acid
  • aliphatic diamines eg, hexam
  • the above-mentioned other additives for example, a phenol-based antioxidant, a phosphorus-based antioxidant, a thioether-based antioxidant, at an arbitrary addition amount, Other antioxidants, hindered amine light stabilizers, ultraviolet absorbers, plasticizers, nucleating agents, flame retardants, flame retardant aids, lubricants, fillers, hydrotalcites, metal soaps, antistatic agents, pigments, Dyes
  • other additives for example, a phenol-based antioxidant, a phosphorus-based antioxidant, a thioether-based antioxidant, at an arbitrary addition amount, Other antioxidants, hindered amine light stabilizers, ultraviolet absorbers, plasticizers, nucleating agents, flame retardants, flame retardant aids, lubricants, fillers, hydrotalcites, metal soaps, antistatic agents, pigments, Dyes
  • the content of other additives in the resin composition of the present invention is as described above.
  • the synthetic resin composition of the present invention is characterized by containing the flame retardant of the present invention or the flame retardant composition of the present invention.
  • the method for blending the flame retardant of the present invention or the flame retardant composition of the present invention with a synthetic resin is not particularly limited, and a known method can be adopted. Specific mixing methods include a method of mixing with a usual blender, a mixer, etc., a method of melt-kneading with an extruder, etc., a method of mixing with a solvent and casting a solution.
  • the molded article of the present invention is obtained by molding the synthetic resin composition of the present invention.
  • the method and molding conditions for molding the synthetic resin composition are not particularly limited, and known methods and molding conditions can be adopted. Specific molding methods include extrusion molding, injection molding, stretched film molding, blow molding and the like, and these molding methods can be carried out under known molding conditions.
  • the shape of the molded body obtained by molding the synthetic resin composition of the present invention is not particularly limited, and examples thereof include a sheet shape, a film shape, and a special shape.
  • the use of the obtained molded article is not particularly limited, but examples thereof include food containers, electronic parts, automobile parts, medical prize materials, film / sheet materials, fiber materials, optical materials, paint resins, ink resins, toner resins. , Resins for adhesives, and the like.
  • the reaction liquid cooled to room temperature was transferred to a beaker, 300 ml of acetone was added, and filtration was performed. This washing operation was repeated three times. The residue was dried in a vacuum oven at 150 ° C for 5 hours. A white powder was obtained. The yield was 32.9 g (80.5%).
  • the obtained compound was identified by 1 H-NMR and 31 P-NMR (measurement device: AVANCE III HD NMR Spectrometer, manufactured by BRUKER Corporation).
  • the obtained compound No. 1 H-NMR and 31 P-NMR of 1 were as follows.
  • the average polymerization degree n of 1 was 47 calculated from 1 H-NMR.
  • the reaction liquid cooled to room temperature was transferred to a beaker, 300 ml of acetone was added, and filtration was performed. This washing operation was repeated three times. The residue was dried in a vacuum oven at 150 ° C for 5 hours. A white powder was obtained. The yield was 34.4 g (75.6%).
  • the obtained compound was identified by 1 H-NMR and 31 P-NMR (measurement device: AVANCE III HD NMR Spectrometer, manufactured by BRUKER Corporation).
  • the obtained compound No. 1 H-NMR and 31 P-NMR of 2 were as follows.
  • the obtained compound No. For 2 the average degree of polymerization n was calculated to be 50 from 1 H-NMR.
  • Comparative Compound A The compound thus obtained was designated as Comparative Compound A.
  • the obtained compound was identified by 1 H-NMR and 31 P-NMR (measurement device: AVANCE III HD NMR Spectrometer, manufactured by BRUKER Corporation).
  • 1 H-NMR and 31 P-NMR of the obtained comparative compound A were as follows.
  • the average degree of polymerization n of Comparative Compound A was calculated to be 43 from 1 H-NMR.
  • Comparative Example 2 (Synthesis of Comparative Compound B) Comparative compound B shown below was synthesized by the method described below.
  • Comparative Compound B The compound thus obtained was designated as Comparative Compound B.
  • the identification of the comparative compound B was performed by 1 H-NMR and 31 P-NMR (measurement device: AVANCE III HD NMR Spectrometer, manufactured by BRUKER Corporation).
  • 1 H-NMR and 31 P-NMR of the obtained comparative compound B were as follows.
  • the average degree of polymerization n of Comparative Compound B was calculated to be 45 from 1 H-NMR.
  • Comparative Compound C The obtained compound was identified by 1 H-NMR and 31 P-NMR (measurement device: AVANCE III HD NMR Spectrometer, manufactured by BRUKER Corporation). 1 H-NMR and 31 P-NMR of the obtained comparative compound C were as follows. The average degree of polymerization n of Comparative Compound C was calculated to be 48 from 1 H-NMR.
  • the identification of the comparative compound D was performed by 1 H-NMR and 31 P-NMR (measurement device: AVANCE III HD NMR Spectrometer, manufactured by BRUKER Corporation). 1 H-NMR and 31 P-NMR of the obtained comparative compound D were as follows.
  • Examples 3 to 10 and Comparative Examples 5 to 8 The components listed in Table 2 below were blended in the blending amounts (% by mass) listed in the same table to obtain a synthetic resin composition. Using this synthetic resin composition, flame retardancy was evaluated by the following evaluation method. Table 2 shows the results.
  • the combustion rank was set according to the UL-94V standard based on the first and second burning times, the presence or absence of cotton ignition. The highest combustion rank is V-0, and the flame retardancy decreases as V-1 and V-2.
  • the synthetic resin compositions of Examples 5 and 10 using the flame retardant (flame retardant resin composition) of the present invention are the same as those of Comparative Examples A to D except that Comparative Compounds A to D are used. It has good flame retardancy as compared with the synthetic resin compositions of Comparative Examples 5 to 8 having the same composition as 5 and 10. From this, it is clear that the flame retardant (flame retardant resin composition) of the present invention can provide a synthetic resin having good flame retardancy.

Landscapes

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

Abstract

La présente invention vise à fournir un ignifuge qui présente une excellente résistance à la chaleur et qui, lorsqu'il est ajouté à des résines synthétiques, en particulier, à des résines à base de polyester, est capable d'améliorer considérablement l'ininflammabilité des résines synthétiques. L'agent ignifuge comprend un composé représenté par la formule générale (1). Dans la formule générale (1), R1 et R3 représentent chacun indépendamment un groupe aromatique monovalent ayant facultativement un ou plusieurs substituants ; X1 et X2 représentent chacun indépendamment une liaison directe, un groupe alkylène en C1-8, un atome d'oxygène, un atome d'azote ou un atome de soufre, tout atome de carbone adjacent du groupe alkylène en C1-8 ayant facultativement un atome d'oxygène, d'azote ou de soufre interposé entre eux ; R2 représente -CH2CH2- ou -CH2CH2CH2- ; et n est un nombre de 1 à 10 000.
PCT/JP2019/037909 2018-10-11 2019-09-26 Ignifuge, composition ignifuge, composition de résine synthétique et objet moulé Ceased WO2020075519A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018192779 2018-10-11
JP2018-192779 2018-10-11

Publications (1)

Publication Number Publication Date
WO2020075519A1 true WO2020075519A1 (fr) 2020-04-16

Family

ID=70164592

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/037909 Ceased WO2020075519A1 (fr) 2018-10-11 2019-09-26 Ignifuge, composition ignifuge, composition de résine synthétique et objet moulé

Country Status (2)

Country Link
TW (1) TW202028443A (fr)
WO (1) WO2020075519A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4342925A1 (fr) 2022-09-26 2024-03-27 EMPA Eidgenössische Materialprüfungs- und Forschungsanstalt Thermodurcissables époxy phosphonates
US20240218174A1 (en) * 2021-11-26 2024-07-04 Lg Chem, Ltd. Thermoplastic resin composition, method of preparing the same, and molded article including the same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5198224A (fr) * 1975-01-23 1976-08-30
JPS54143500A (en) * 1978-04-28 1979-11-08 American Cyanamid Co Phosphonic acid pentaerythrityl polymer
US4278591A (en) * 1979-12-20 1981-07-14 American Cyanamid Company Flame retardant poly(butylene terephthalate) composition
JP2000290288A (ja) * 1999-03-31 2000-10-17 Chisso Corp ポリリン酸エステルの製造方法
JP2004210968A (ja) * 2003-01-06 2004-07-29 Teijin Chem Ltd 難燃性樹脂組成物およびそれからの成形品
WO2018190157A1 (fr) * 2017-04-14 2018-10-18 株式会社Adeka Nouveau composé et composition de résine

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5198224A (fr) * 1975-01-23 1976-08-30
JPS54143500A (en) * 1978-04-28 1979-11-08 American Cyanamid Co Phosphonic acid pentaerythrityl polymer
US4278591A (en) * 1979-12-20 1981-07-14 American Cyanamid Company Flame retardant poly(butylene terephthalate) composition
JP2000290288A (ja) * 1999-03-31 2000-10-17 Chisso Corp ポリリン酸エステルの製造方法
JP2004210968A (ja) * 2003-01-06 2004-07-29 Teijin Chem Ltd 難燃性樹脂組成物およびそれからの成形品
WO2018190157A1 (fr) * 2017-04-14 2018-10-18 株式会社Adeka Nouveau composé et composition de résine

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20240218174A1 (en) * 2021-11-26 2024-07-04 Lg Chem, Ltd. Thermoplastic resin composition, method of preparing the same, and molded article including the same
EP4342925A1 (fr) 2022-09-26 2024-03-27 EMPA Eidgenössische Materialprüfungs- und Forschungsanstalt Thermodurcissables époxy phosphonates
WO2024068565A1 (fr) 2022-09-26 2024-04-04 Empa Eidgenössische Materialprüfungs- Und Forschungsanstalt Thermodurcis à base de phosphonate époxy

Also Published As

Publication number Publication date
TW202028443A (zh) 2020-08-01

Similar Documents

Publication Publication Date Title
FI110117B (fi) Liekinkestävä muovipuristusmassa, jolla on parantunut stabiilisuus
US12139590B2 (en) Resin additive composition and synthetic resin composition using same
KR100282620B1 (ko) 폴리프로필렌 섬유에 대한 낮은 색형성 가공, 열 및 광 안정화제계
KR20150130896A (ko) 스피로 비스포스파이트계 화합물 및 이의 용도
WO2020075519A1 (fr) Ignifuge, composition ignifuge, composition de résine synthétique et objet moulé
JP7663520B2 (ja) 耐燃焼性ポリマー組成物およびそれから作製した物品
CN111051412A (zh) 组合物、使用其的热塑性树脂组合物及其成型体
WO2019045013A1 (fr) Composition, composition de résine thermoplastique l'utilisant et article moulé en cette composition
WO2018190157A1 (fr) Nouveau composé et composition de résine
TWI771421B (zh) 難燃劑組合物及含有其之難燃性樹脂組合物
WO2019117049A1 (fr) Composition et composition de résine ignifuge
JP6717624B2 (ja) 熱可塑性ポリウレタン樹脂組成物
WO2021201085A1 (fr) Composition ignifuge, composition de résine synthétique résistante aux flammes, et corps moulé
JP2014224187A (ja) 熱安定剤組成物、合成樹脂組成物、およびこれを用いた成形品
WO2013176216A1 (fr) Composition de stabilisant, composition de résine, et produit moulé l'utilisant
JP2010229361A (ja) ポリオレフィン系樹脂組成物
JP2013245269A (ja) 安定剤組成物の製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19870086

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19870086

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP