KR20060069436A - 열가소체용 난연성 포스포네이트 첨가제 - Google Patents
열가소체용 난연성 포스포네이트 첨가제 Download PDFInfo
- Publication number
- KR20060069436A KR20060069436A KR1020067002237A KR20067002237A KR20060069436A KR 20060069436 A KR20060069436 A KR 20060069436A KR 1020067002237 A KR1020067002237 A KR 1020067002237A KR 20067002237 A KR20067002237 A KR 20067002237A KR 20060069436 A KR20060069436 A KR 20060069436A
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- Prior art keywords
- alkyl
- general formula
- phosphonate
- represented
- phosphite
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 title claims abstract description 46
- 239000003063 flame retardant Substances 0.000 title claims abstract description 39
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 239000000654 additive Substances 0.000 title description 14
- 229920001169 thermoplastic Polymers 0.000 title description 14
- 239000004416 thermosoftening plastic Substances 0.000 title description 14
- 238000000034 method Methods 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- -1 4-t-butylcyclohexyl Chemical group 0.000 claims description 30
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000001350 alkyl halides Chemical class 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical group CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 4
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical group CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims description 3
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical group CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- PQDJLAHLMWEHPA-UHFFFAOYSA-N 1-dimethoxyphosphoryldecane Chemical compound CCCCCCCCCCP(=O)(OC)OC PQDJLAHLMWEHPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims 2
- 241000723346 Cinnamomum camphora Species 0.000 claims 2
- 229960000846 camphor Drugs 0.000 claims 2
- 229930008380 camphor Natural products 0.000 claims 2
- RPFRYQDHUIHAFC-UHFFFAOYSA-N 1-dimethoxyphosphoryldodecane Chemical compound CCCCCCCCCCCCP(=O)(OC)OC RPFRYQDHUIHAFC-UHFFFAOYSA-N 0.000 claims 1
- 239000011342 resin composition Substances 0.000 claims 1
- 229920005992 thermoplastic resin Polymers 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- HYQXIVAZQBYBAF-UHFFFAOYSA-N 1-diethoxyphosphoryldecane Chemical compound CCCCCCCCCCP(=O)(OCC)OCC HYQXIVAZQBYBAF-UHFFFAOYSA-N 0.000 description 1
- DPWMQGCYGZBIFW-UHFFFAOYSA-N 1-dipropoxyphosphoryldodecane Chemical compound CCCCCCCCCCCCP(=O)(OCCC)OCCC DPWMQGCYGZBIFW-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
- ZRQMCAMQYMKCSB-UHFFFAOYSA-N CCCOP(OCC(C)C1=CC=CC=C1)=O Chemical compound CCCOP(OCC(C)C1=CC=CC=C1)=O ZRQMCAMQYMKCSB-UHFFFAOYSA-N 0.000 description 1
- 235000012545 Vaccinium macrocarpon Nutrition 0.000 description 1
- 235000002118 Vaccinium oxycoccus Nutrition 0.000 description 1
- 244000291414 Vaccinium oxycoccus Species 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000004634 cranberry Nutrition 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- QCKLYDQORUPOIR-UHFFFAOYSA-N ethyl dimethyl phosphite Chemical compound CCOP(OC)OC QCKLYDQORUPOIR-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5357—Esters of phosphonic acids cyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L23/32—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with compounds containing phosphorus or sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
ABS 쿠폰 | 난연성 포스포네이트 | 증가 중량% |
1 | 포스포네이트 A | 3.48% |
2 | Amgard CU | 5.64% |
샘플 | 원래 중량의 10%가 손실되었을 때의 온도(℃) |
포스포네이트 FR B | 350 |
Amgard 1045 | 315 |
Claims (32)
- 제1항에 있어서,상기 일반식에서, R1 및 R2는 메틸기이고, R3는 에틸이며, R4는 치환된 또는 치환되지 않은 C10∼C18 알킬인 것을 특징으로 하는 조성물.
- 제2항에 있어서,상기 일반식에서, R4는 C10 알킬 또는 C12 알킬인 것을 특징으로 하는 조성물.
- 제1항에 있어서,상기 일반식에서, R1 및 R2는 메틸기이고, R3는 에틸이며, R4는 치환된 또는 치환되지 않은 C10∼C12 사이클로알킬인 것을 특징으로 하는 조성물.
- 제4항에 있어서,상기 일반식에서 R4가 4-t-부틸사이클로헥실인 것을 특징으로 하는 조성물.
- 제4항에 있어서,상기 일반식에서 R4가 캄필(camphyl)인 것을 특징으로 하는 조성물.
- 제7항에 있어서,상기 일반식에서, R1 및 R2는 메틸기이고, R3는 에틸이며, R4는 치환된 또는 치환되지 않은 C10∼C18 알킬인 것을 특징으로 하는 조성물.
- 제8항에 있어서,상기 일반식에서, R4는 C10 알킬 또는 C12 알킬인 것을 특징으로 하는 조성물.
- 제7항에 있어서,상기 일반식에서, R1 및 R2는 메틸기이고, R3는 에틸이며, R4는 치환된 또는 치환되지 않은 C10∼C12 사이클로알킬인 것을 특징으로 하는 조성물.
- 제10항에 있어서,상기 일반식에서 R4가 4-t-부틸사이클로헥실인 것을 특징으로 하는 조성물.
- 제10항에 있어서,상기 일반식에서 R4가 캄필인 것을 특징으로 하는 조성물.
- 난연성 포스포네이트 조성물의 제조 방법으로서,상기 조성물은 하기 일반식 (IV)로 표시되며:(상기 일반식 (IV)에서,각각의 R1 및 R2는 독립적으로 C1∼C4 알킬이고,R3는 H, 또는 C1∼C4 알킬이고,R4는 선형 또는 분지형의 C9∼C22 알킬, C9∼C22 사이클로알킬, C9∼C22 아릴, 또는 C9∼C22 아랄킬이며,n= 0 또는 1임),상기 방법은,(1) 하기 일반식 (I)로 표시되는 트리메틸올알칸과 일반식 P(OR)3 (단, R은 알킬, 아릴, 또는 아랄킬임)로 표시되는 포스파이트를, 하기 일반식 (II)로 표시되는 환형 포스파이트를 생성하기에 충분한 몰 비로 반응시키는 단계:(상기 각각의 일반식 (I) 및 (II)에서, R3는 H, 또는 C1∼C4 알킬임); 및(2) 상기 일반식 (II)로 표시되는 환형 포스파이트와 하기 일반식 (III)으로 표시되는 포스포네이트를, 상기 일반식 (IV)로 표시되는 난연성 포스포네이트를 생성하기에 충분한 몰 비로 반응시키는 단계:(상기 일반식 (III)에서,각각의 R1 및 R2는 독립적으로 C1∼C4 알킬이고,R4는 선형 또는 분지형의 C9∼C22 알킬, C9∼C22 사이클로알킬, C9∼C22 아릴, 또는 C9∼C22 아랄킬임)를 포함하는 것을 특징으로 하는 제조 방법.
- 제13항에 있어서,상기 (1)단계의 반응이 에스테르교환 촉매의 존재 또는 부재 하에, 약 50℃ 내지 약 200℃의 온도에서 수행되는 것을 특징으로 하는 제조 방법.
- 제14항에 있어서,상기 (1)단계의 반응이 약 80℃ 내지 약 160℃의 온도에서 수행되는 것을 특징으로 하는 제조 방법.
- 제14항에 있어서,상기 (1)단계의 반응이 에스테르교환 촉매의 존재 하에 수행되는 것을 특징으로 하는 제조 방법.
- 제16항에 있어서,상기 촉매가 메틸 산 포스페이트(methyl acid phosphate)인 것을 특징으로 하는 제조 방법.
- 제13항에 있어서,상기 트리메틸올알칸이 트리메틸올프로판을 포함하는 것을 특징으로 하는 제조 방법.
- 제13항에 있어서,상기 일반식 P(OR)3로 표시되는 포스파이트가 트리메틸 포스파이트를 포함하는 것을 특징으로 하는 제조 방법.
- 제13항에 있어서,상기 일반식 P(OR)3로 표시되는 포스파이트가 트리페닐 포스파이트를 포함하는 것을 특징으로 하는 제조 방법.
- 제13항에 있어서,상기 (2)단계의 반응이 알킬 할라이드 촉매 및/또는 착색 억제제(color inhibitor)의 존재, 또는 부재 하에, 약 150℃ 내지 약 250℃의 온도에서 수행되는 것을 특징으로 하는 제조 방법.
- 제21항에 있어서,상기 (2)단계의 반응이 알킬 할라이드 촉매의 존재 하에 수행되는 것을 특징 으로 하는 제조 방법.
- 제22항에 있어서,상기 알킬 할라이드 촉매가 부틸 브로마이드인 것을 특징으로 하는 제조 방법.
- 제22항에 있어서,상기 알킬 할라이드 촉매가 옥틸 브로마이드인 것을 특징으로 하는 제조 방법.
- 제22항에 있어서,상기 알킬 할라이드 촉매가 메틸 아이오다이드(methyl iodide)인 것을 특징으로 하는 제조 방법.
- 제21항에 있어서,상기 (2)단계의 반응이 착색 억제제의 존재 하에 수행되는 것을 특징으로 하는 제조 방법.
- 제26항에 있어서,상기 착색 억제제가 N-메틸에탄올 아민인 것을 특징으로 하는 제조 방법.
- 제21항에 있어서,상기 (2)단계의 반응이 약 180℃ 내지 약 220℃의 온도에서 수행되는 것을 특징으로 하는 제조 방법.
- 제21항에 있어서,상기 일반식 (III)으로 표시되는 포스포네이트가 디메틸 데실포스포네이트인 것을 특징으로 하는 제조 방법.
- 제21항에 있어서,상기 일반식 (III)으로 표시되는 포스포네이트가 디메틸 라우릴포스포네이트인 것을 특징으로 하는 제조 방법.
- 제21항에 있어서,상기 일반식 (III)으로 표시되는 포스포네이트가 디메틸 (4-t-부틸사이클로헥실)포스포네이트인 것을 특징으로 하는 제조 방법.
- 제21항에 있어서,상기 일반식 (III)으로 표시되는 포스포네이트가 디메틸 캄필포스포네이트인 것을 특징으로 하는 제조 방법.
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US49191403P | 2003-08-01 | 2003-08-01 | |
US60/491,914 | 2003-08-01 | ||
PCT/US2004/024812 WO2005012420A2 (en) | 2003-08-01 | 2004-07-30 | Flame retardant phosphonate additives for thermoplastics |
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KR20060069436A true KR20060069436A (ko) | 2006-06-21 |
KR101117654B1 KR101117654B1 (ko) | 2012-05-09 |
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US (1) | US7067076B2 (ko) |
EP (1) | EP1651737B1 (ko) |
JP (1) | JP4695080B2 (ko) |
KR (1) | KR101117654B1 (ko) |
CN (1) | CN100453620C (ko) |
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CN1969009A (zh) * | 2004-06-18 | 2007-05-23 | 第一毛织株式会社 | 阻燃热塑性树脂组合物 |
WO2007006915A1 (fr) * | 2005-07-05 | 2007-01-18 | Rhodia Uk Limited | Produit ignifuge phosphonate et procede |
WO2007018340A1 (en) * | 2005-08-08 | 2007-02-15 | Cheil Industries Inc. | Flame retardant molding composition |
KR100764650B1 (ko) | 2005-08-08 | 2007-10-08 | 제일모직주식회사 | 난연성 열가소성 수지 조성물 |
KR100817399B1 (ko) * | 2005-12-29 | 2008-03-27 | 제일모직주식회사 | 난연성 열가소성 수지 조성물 |
WO2011082207A2 (en) * | 2009-12-30 | 2011-07-07 | E. I. Du Pont De Nemours And Company | Flame retardant poly(trimethylene terephthalate) compositions |
EP2619213B1 (en) | 2010-09-23 | 2014-09-03 | ICL-IP America Inc. | Monohydroxy cyclic phosphonate substantially free of polyhydoxy phosphonate, process for making same and flame retardant flexible polyurethane foam obtained therefrom |
CN102675371A (zh) * | 2012-04-25 | 2012-09-19 | 东华大学 | 一种环状苯基膦酸酯化合物及其制备方法 |
TWI445755B (zh) * | 2012-06-27 | 2014-07-21 | Ind Tech Res Inst | 阻燃性熱可塑性澱粉材料、生質複材及其製備方法 |
US9068120B2 (en) | 2012-08-09 | 2015-06-30 | Empire Technology Development Llc | Flame retardant nylon |
EP3002311A1 (en) | 2014-10-03 | 2016-04-06 | Kaneka Belgium N.V. | Flame retardant pre-expanded polymer material, in-mold or extruded foamed article and process for producing the material |
CN105254672B (zh) * | 2015-10-26 | 2017-12-22 | 苏州科技大学 | 阻燃剂苯基三(磷杂环甲氧基)硅烷化合物及其制备方法 |
CN105254676B (zh) * | 2015-10-26 | 2017-11-24 | 苏州科技大学 | 甲基苯基双(磷杂环甲氧基)硅烷化合物及其制备方法 |
CN105440079A (zh) * | 2015-11-20 | 2016-03-30 | 浙江传化股份有限公司 | 一种纺织用混合阻燃剂的制备方法 |
EP3660064A1 (de) * | 2018-11-28 | 2020-06-03 | LANXESS Deutschland GmbH | Zubereitungen mit verbesserter wirksamkeit als flammschutzmittel |
CN111377967A (zh) * | 2020-02-26 | 2020-07-07 | 青岛长荣化工科技有限公司 | 一种环状膦酸酯阻燃剂的制备方法 |
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US3849368A (en) * | 1971-11-15 | 1974-11-19 | Mobil Oil Corp | Fire retardant polymers containing thermally stable cyclic phosphonate esters |
US3789091A (en) * | 1971-11-15 | 1974-01-29 | Mobil Oil Corp | Cyclic phosphonate esters and their preparation |
JPS5319747Y2 (ko) * | 1972-02-19 | 1978-05-25 | ||
US4073767A (en) * | 1976-09-03 | 1978-02-14 | Monsanto Company | Hydrogen phosphonates and polymers containing them as flame retardants |
US4397759A (en) * | 1977-09-01 | 1983-08-09 | Henry Hancock | Fire retardant for polyolefins |
DK148757C (da) * | 1981-09-22 | 1986-02-17 | B & W Diesel As | Udstoedsventil til en stempelforbraendingsmotor |
GB9004633D0 (en) * | 1990-03-01 | 1990-04-25 | Albright & Wilson | Flame retardant composition and method of use |
EP0754728A1 (de) * | 1995-07-14 | 1997-01-22 | Hoechst Aktiengesellschaft | Flammwidrige Epoxidharz-Formmassen |
FR2737407B1 (fr) * | 1995-07-31 | 1997-09-12 | Oreal | Utilisation d'acides carboxyliques hydroxyles pour le traitement des matieres keratiniques |
GB9516794D0 (en) * | 1995-08-16 | 1995-10-18 | Albright & Wilson | Flame retardant product and process |
GB9623584D0 (en) * | 1996-11-13 | 1997-01-08 | Albright & Wilson Uk Ltd | Alkylene-bridged alkyl phosphonates |
US6502325B1 (en) * | 1999-09-02 | 2003-01-07 | Colgate-Palmolive Co. | Method of treating fabric with fabric care composition containing polycarboxylate polymer and compound derived from urea |
US6576700B2 (en) | 2000-04-12 | 2003-06-10 | General Electric Company | High flow polyphenylene ether formulations |
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JP4695080B2 (ja) | 2011-06-08 |
ES2451848T3 (es) | 2014-03-28 |
WO2005012420A2 (en) | 2005-02-10 |
KR101117654B1 (ko) | 2012-05-09 |
CN1833015A (zh) | 2006-09-13 |
EP1651737A4 (en) | 2008-12-24 |
EP1651737A2 (en) | 2006-05-03 |
CN100453620C (zh) | 2009-01-21 |
WO2005012420A3 (en) | 2006-02-16 |
JP2007501313A (ja) | 2007-01-25 |
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US7067076B2 (en) | 2006-06-27 |
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