CN1210284C - 基于双酚a双(磷酸二苯酯)的阻燃剂 - Google Patents
基于双酚a双(磷酸二苯酯)的阻燃剂 Download PDFInfo
- Publication number
- CN1210284C CN1210284C CNB008087938A CN00808793A CN1210284C CN 1210284 C CN1210284 C CN 1210284C CN B008087938 A CNB008087938 A CN B008087938A CN 00808793 A CN00808793 A CN 00808793A CN 1210284 C CN1210284 C CN 1210284C
- Authority
- CN
- China
- Prior art keywords
- area
- fire retardant
- dihydroxyphenyl propane
- diphenyl phosphate
- hplc
- 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.)
- Expired - Fee Related
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 64
- 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 5
- BQPNUOYXSVUVMY-UHFFFAOYSA-N [4-[2-(4-diphenoxyphosphoryloxyphenyl)propan-2-yl]phenyl] diphenyl phosphate Chemical compound C=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BQPNUOYXSVUVMY-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 23
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims abstract description 12
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 66
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 26
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 229920005992 thermoplastic resin Polymers 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 229920013636 polyphenyl ether polymer Polymers 0.000 claims 1
- 239000000539 dimer Substances 0.000 abstract description 14
- WLXXENAUDPZXIB-UHFFFAOYSA-N diphenyl (2-prop-1-en-2-ylphenyl) phosphate Chemical compound CC(=C)C1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 WLXXENAUDPZXIB-UHFFFAOYSA-N 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 29
- 238000005406 washing Methods 0.000 description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000012535 impurity Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 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 13
- 238000000034 method Methods 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical group CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 239000003518 caustics Substances 0.000 description 6
- MQHNKCZKNAJROC-UHFFFAOYSA-N dipropyl phthalate Chemical compound CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical class C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 239000008399 tap water Substances 0.000 description 5
- 235000020679 tap water Nutrition 0.000 description 5
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- 238000004679 31P NMR spectroscopy Methods 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- -1 phosphate ester Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 235000013849 propane Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920007019 PC/ABS Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- KMLJVJRQAFXKKA-UHFFFAOYSA-N Cl[P](Cl)(Cl)Cl Chemical class Cl[P](Cl)(Cl)Cl KMLJVJRQAFXKKA-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229960002337 magnesium chloride Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229940073589 magnesium chloride anhydrous Drugs 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/330,688 | 1999-06-11 | ||
| US09/330,688 US6319432B1 (en) | 1999-06-11 | 1999-06-11 | Bisphenol-A bis(diphenyl phosphate)-based flame retardant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1355808A CN1355808A (zh) | 2002-06-26 |
| CN1210284C true CN1210284C (zh) | 2005-07-13 |
Family
ID=23290873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB008087938A Expired - Fee Related CN1210284C (zh) | 1999-06-11 | 2000-06-06 | 基于双酚a双(磷酸二苯酯)的阻燃剂 |
Country Status (6)
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3926938B2 (ja) * | 1998-12-03 | 2007-06-06 | 三菱エンジニアリングプラスチックス株式会社 | 難燃性ポリカーボネート樹脂組成物 |
| DE10036057A1 (de) * | 2000-07-25 | 2002-02-07 | Bayer Ag | Flammwidrige Polycarbonat-Zusammensetzungen |
| US6399685B1 (en) * | 2000-12-11 | 2002-06-04 | Albemarle Corporation | Purification of arylene polyphosphate esters |
| DE10100591A1 (de) * | 2001-01-09 | 2002-07-11 | Bayer Ag | Phosphorhaltiges Flammschutzmittel und Flammwidrige thermoplastische Formmassen |
| US7303810B2 (en) * | 2001-03-05 | 2007-12-04 | 3Form, Inc. | Fire-resistant architectural resin materials |
| US7691470B2 (en) * | 2001-03-05 | 2010-04-06 | 3Form | Laminate structure with polycarbonate sheets |
| US7008700B1 (en) | 2001-03-05 | 2006-03-07 | 3-Form | Architectural laminate panel with embedded compressible objects and methods for making the same |
| US6667355B2 (en) * | 2001-08-30 | 2003-12-23 | Pabu Services, Inc. | Higher alkylated triaryl phosphate ester flame retardants |
| DE10216736A1 (de) * | 2002-04-16 | 2004-02-05 | Bayer Ag | Flammschutzmittel für Polymere enthaltend eine Mischung aus zwei verschiedenen Arylphosphaten, deren Herstellung und deren Verwendung |
| CN1708503A (zh) * | 2002-10-26 | 2005-12-14 | 阿克苏诺贝尔公司 | 低聚磷酸酯组合物结晶的延迟 |
| US20060046017A1 (en) | 2004-09-01 | 2006-03-02 | 3Form | Architectural glass panels with embedded objects and methods for making the same |
| US20060068317A1 (en) * | 2004-09-30 | 2006-03-30 | Klei Steven R | Poly(arylene ether) composition |
| WO2007056456A1 (en) * | 2005-11-08 | 2007-05-18 | Supresta Llc | Flame retardant composition and hydrolysis-susceptible resin containing same |
| US20070254991A1 (en) * | 2006-04-28 | 2007-11-01 | Saadat Hussain | Phosphorus-containing tetrabromobisphenol A |
| TW200813197A (en) * | 2006-07-07 | 2008-03-16 | Albemarle Corp | Phosphorous-based flame retardant recovery method |
| BRPI0811211A8 (pt) | 2007-05-08 | 2016-04-26 | 3Form Inc | Sistema de cor multivariado com aplicação de textura |
| US8968611B2 (en) * | 2008-06-09 | 2015-03-03 | Adeka Corporation | Process for solidification of phosphoric ester-based flame retardants |
| CN101348500B (zh) * | 2008-08-19 | 2012-02-22 | 山东默锐化学有限公司 | 一种双酚a双(二苯基磷酸酯)的制备方法 |
| KR101013666B1 (ko) * | 2008-09-18 | 2011-02-10 | 한밭대학교 산학협력단 | 컴퓨터용 방열장치 |
| EP2358816B1 (en) * | 2008-12-08 | 2021-03-24 | SABIC Global Technologies B.V. | Flame retardant polycarbonate compositions, method of manufacture thereof, and articles therefrom |
| WO2011054862A1 (de) | 2009-11-05 | 2011-05-12 | Bayer Materialscience Ag | Platten aus polycarbonat mit verbesserter flammwidrigkeit |
| TWI382988B (zh) * | 2009-12-25 | 2013-01-21 | Grand Tek Advance Material Science Co Ltd | 有機矽磷酸酯及其製作方法 |
| CN101831308A (zh) * | 2010-04-19 | 2010-09-15 | 江苏大明科技有限公司 | 一种高分子量固体磷酸酯阻燃剂及其制备方法和应用 |
| CN101993586B (zh) * | 2010-11-30 | 2012-10-10 | 金发科技股份有限公司 | 一种阻燃的聚碳酸酯/abs材料 |
| TWI410446B (zh) | 2011-01-05 | 2013-10-01 | Grand Tek Advance Material Science Co Ltd | 含磷酚醛樹脂與其形成方法及含磷配方 |
| SE535836C2 (sv) * | 2011-10-21 | 2013-01-08 | Perstorp Ab | Ny fosfatförening |
| USD691289S1 (en) | 2012-09-05 | 2013-10-08 | 3Form, Inc. | Panel with cut and aligned thatch interlayer |
| CN104829647B (zh) * | 2014-04-10 | 2016-08-24 | 北京理工阻燃科技有限公司 | 一种含磷聚醚酯的制备方法及应用 |
| US10240030B2 (en) * | 2014-12-02 | 2019-03-26 | Sabic Global Technologies B.V. | Article comprising a high flow polyetherimide composition |
| JP6532276B2 (ja) * | 2015-04-23 | 2019-06-19 | 株式会社Adeka | 難燃性水系ポリウレタン樹脂組成物、及びそれを塗布してなる難燃性ポリエステル系繊維 |
| CN104962059B (zh) * | 2015-06-18 | 2016-11-02 | 金发科技股份有限公司 | 一种聚碳酸酯组合物及其制备方法 |
| CN106699805B (zh) * | 2016-12-15 | 2019-02-01 | 衢州普信新材料有限公司 | 一种双酚a双（二苯基磷酸酯）的制备方法 |
| CN108676282A (zh) * | 2018-05-18 | 2018-10-19 | 武汉理工大学 | 一种环保阻燃型pvc/abs合金及其制备方法 |
| CN111040457B (zh) * | 2019-12-27 | 2022-05-06 | 广东精一塑胶实业有限公司 | 一种用于塑料的固化包覆阻燃防水剂的制备方法 |
| CN112142779B (zh) * | 2020-10-13 | 2023-01-13 | 中国科学院宁波材料技术与工程研究所 | 一种双酚a双(磷酸二芳酯)的快速制备方法 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2520090A (en) | 1947-12-30 | 1950-08-22 | Monsanto Chemicals | Polyphosphates of divalent aryl hydrocarbons |
| GB734767A (en) | 1952-01-10 | 1955-08-10 | Lankro Chem Ltd | New neutral orthophosphate esters |
| US3174931A (en) | 1961-12-05 | 1965-03-23 | Sinclair Research Inc | Grease compositions |
| US3360591A (en) | 1962-07-31 | 1967-12-26 | Mobil Oil Corp | Diphosphates of divalent aryl hydrocarbons |
| US3254973A (en) | 1962-07-31 | 1966-06-07 | Socony Mobil Oil Co Inc | Gasolines and phosphorus-containing additives therefor |
| US3317636A (en) | 1964-01-10 | 1967-05-02 | American Cyanamid Co | O, o, o', o'-tetramethyl o, o'-thiodi-p-phenylene phosphorothioate |
| JPS5051154A (US06319432-20011120-C00002.png) | 1973-09-06 | 1975-05-07 | ||
| AU8671075A (en) | 1974-12-06 | 1977-05-26 | Gen Electric | Flame retardant, non-dripping composition of polyphenylene ether and acrylonitrile - butadiene-styrene |
| GB2043083A (en) | 1979-03-06 | 1980-10-01 | Gen Electric | Flame retardant polyphenylene ether compositions |
| US4223100A (en) | 1979-04-18 | 1980-09-16 | Mobay Chemical Corporation | Flame retardant aromatic polycarbonate with good mechanical properties and melt stability |
| DE3277772D1 (en) | 1981-09-09 | 1988-01-14 | Sumitomo Naugatuck | Thermoplastic composition |
| JPS5924736A (ja) | 1982-08-02 | 1984-02-08 | Adeka Argus Chem Co Ltd | 難燃性ポリスチレン系樹脂組成物 |
| JPS5945351A (ja) | 1982-09-08 | 1984-03-14 | Adeka Argus Chem Co Ltd | 難燃性組成物 |
| EP0103230B1 (de) | 1982-09-10 | 1988-06-22 | Bayer Ag | Flammwidrige Polymermischungen |
| JPS59202240A (ja) | 1983-05-02 | 1984-11-16 | Daihachi Kagaku Kogyosho:Kk | 難燃性熱可塑性樹脂組成物 |
| DE3523314A1 (de) | 1985-06-29 | 1987-01-02 | Bayer Ag | Thermoplastische polycarbonatformmassen |
| JPS63117057A (ja) | 1986-10-31 | 1988-05-21 | Daihachi Kagaku Kogyosho:Kk | 難燃性耐熱性芳香族ビニル系樹脂組成物 |
| DE3700208A1 (de) | 1987-01-07 | 1988-07-21 | Bayer Ag | Phosphorhaltige oligomere und polymere mit polyphenylenetherbloecken sowie mischungen anderer kunststoffe mit ihnen |
| DE3819081A1 (de) | 1988-06-04 | 1989-12-07 | Bayer Ag | Flammwidrige, schlagzaehe polycarbonat-formmassen |
| CA1334695C (en) | 1988-09-07 | 1995-03-07 | Jurou Ohzeki | Electroless plating-susceptive, fire retardant polyphenylene ether resin |
| US5204394A (en) | 1988-09-22 | 1993-04-20 | General Electric Company | Polymer mixture having aromatic polycarbonate, styrene I containing copolymer and/or graft polymer and a flame-retardant, articles formed therefrom |
| USRE36188E (en) | 1989-09-20 | 1999-04-06 | General Electric Company | Polymer mixture having aromatic polycarbonate styrene I containing copolymer and/or graft polymer and a flame-retardant, articles formed therefrom |
| US5281741A (en) | 1990-11-13 | 1994-01-25 | Fmc Corporation | Process for preparing aryldiphosphate esters |
| JPH0598118A (ja) | 1991-10-14 | 1993-04-20 | Asahi Chem Ind Co Ltd | スチレン系難燃耐熱耐衝撃性樹脂組成物 |
| JP3137400B2 (ja) | 1992-01-16 | 2001-02-19 | 旭化成工業株式会社 | ポリフェニレンエーテル系難燃樹脂組成物 |
| US5278279A (en) | 1992-03-11 | 1994-01-11 | Daicel Chemical Industries, Ltd. | Process for producing (co)polycarbonate with transesterification catalyst and compound |
| EP0611798B1 (en) | 1992-08-06 | 1998-10-21 | Asahi Kasei Kogyo Kabushiki Kaisha | Resin composition |
| US5420327A (en) | 1992-09-14 | 1995-05-30 | Akzo Nobel N.V. | Process for forming hydrocarbyl bisphosphate compound |
| DE4328656A1 (de) | 1993-08-26 | 1995-03-02 | Bayer Ag | Flammwidrige, spannungsrißbeständige Polycarbonat-ABS-Formmassen |
| US5750756A (en) | 1994-11-01 | 1998-05-12 | Akzo Nobel Nv | Process for the formation of hydrocarbyl bis(hydrocarbyl phosphate) |
| US5952408A (en) | 1994-12-01 | 1999-09-14 | Cheil Industries, Inc. | Flameproof thermoplastic resin compositions |
| JPH0995610A (ja) | 1995-09-30 | 1997-04-08 | Nippon G Ii Plast Kk | 難燃樹脂組成物 |
| WO1997047361A1 (en) * | 1996-06-12 | 1997-12-18 | Southwest Research Institute | Fire extinguishing trash can liner |
| US5756798A (en) | 1996-06-13 | 1998-05-26 | Great Lakes Chemical Corporation | Process to prepare aryldiphosphoric esters |
| JP3558458B2 (ja) | 1996-07-10 | 2004-08-25 | 旭化成ケミカルズ株式会社 | アリール燐酸エステルの製造方法 |
| IL131379A0 (en) | 1997-02-14 | 2001-01-28 | Great Lakes Chemical Corp | A flame retardant polymer resin containing bisaryl diphosphate and a method for making the same |
| DE59707291D1 (de) * | 1997-02-17 | 2002-06-20 | Bessey & Sohn | Spanneinrichtung |
| MY121010A (en) | 1997-08-29 | 2005-12-30 | Sabic Innovative Plastics Ip | Polycarbonate resin composition |
| TW455605B (en) | 1998-02-13 | 2001-09-21 | Gen Electric | Flame retardant carbonate polymer composition with improved hydrolytic stability |
| WO1999055771A1 (en) | 1998-04-29 | 1999-11-04 | Great Lakes Chemical Corporation | Continuous process for the manufacture of phosphoric acid esters |
-
1999
- 1999-06-11 US US09/330,688 patent/US6319432B1/en not_active Expired - Fee Related
-
2000
- 2000-06-06 WO PCT/US2000/015598 patent/WO2000077012A1/en active Search and Examination
- 2000-06-06 EP EP00939617A patent/EP1194435A1/en not_active Withdrawn
- 2000-06-06 CN CNB008087938A patent/CN1210284C/zh not_active Expired - Fee Related
- 2000-06-06 JP JP2001503869A patent/JP2003502451A/ja not_active Withdrawn
- 2000-06-06 KR KR1020017015969A patent/KR100720873B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1355808A (zh) | 2002-06-26 |
| KR100720873B1 (ko) | 2007-05-22 |
| JP2003502451A (ja) | 2003-01-21 |
| WO2000077012A1 (en) | 2000-12-21 |
| EP1194435A1 (en) | 2002-04-10 |
| US6319432B1 (en) | 2001-11-20 |
| KR20020010927A (ko) | 2002-02-06 |
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