JP2013536166A - ビフェニル‐４‐イルジフェニルホスフェート組成物の製造方法 - Google Patents
ビフェニル‐４‐イルジフェニルホスフェート組成物の製造方法 Download PDFInfo
- Publication number
- JP2013536166A JP2013536166A JP2013519587A JP2013519587A JP2013536166A JP 2013536166 A JP2013536166 A JP 2013536166A JP 2013519587 A JP2013519587 A JP 2013519587A JP 2013519587 A JP2013519587 A JP 2013519587A JP 2013536166 A JP2013536166 A JP 2013536166A
- Authority
- JP
- Japan
- Prior art keywords
- biphenyl
- anhydrous
- dehydrochlorination reaction
- chemical formula
- phosphate composition
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 17
- 239000010452 phosphate Substances 0.000 title claims abstract description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 6
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims abstract description 28
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000007033 dehydrochlorination reaction Methods 0.000 claims abstract description 23
- 239000000126 substance Substances 0.000 claims abstract description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims description 4
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 239000011565 manganese chloride Substances 0.000 claims description 4
- 229940099607 manganese chloride Drugs 0.000 claims description 4
- 235000002867 manganese chloride Nutrition 0.000 claims description 4
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 3
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 claims description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 2
- 229910021569 Manganese fluoride Inorganic materials 0.000 claims description 2
- CTNMMTCXUUFYAP-UHFFFAOYSA-L difluoromanganese Chemical compound F[Mn]F CTNMMTCXUUFYAP-UHFFFAOYSA-L 0.000 claims description 2
- 229960002089 ferrous chloride Drugs 0.000 claims description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- FZGIHSNZYGFUGM-UHFFFAOYSA-L iron(ii) fluoride Chemical compound [F-].[F-].[Fe+2] FZGIHSNZYGFUGM-UHFFFAOYSA-L 0.000 claims description 2
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 claims description 2
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 abstract description 18
- 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 abstract description 12
- 239000011347 resin Substances 0.000 abstract description 10
- 229920005989 resin Polymers 0.000 abstract description 10
- 239000004014 plasticizer Substances 0.000 abstract description 8
- YHTCUUPQEPBRRC-UHFFFAOYSA-N diphenyl (4-phenylphenyl) phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC(=CC=1)C=1C=CC=CC=1)(=O)OC1=CC=CC=C1 YHTCUUPQEPBRRC-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004811 liquid chromatography Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 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 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000007423 decrease Effects 0.000 description 3
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- -1 phosphate ester Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AAOADXIHXYIOMT-UHFFFAOYSA-N 1,1'-biphenyl;phosphoric acid Chemical group OP(O)(O)=O.C1=CC=CC=C1C1=CC=CC=C1 AAOADXIHXYIOMT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- AEMOLEFTQBMNLQ-QIUUJYRFSA-N beta-D-glucuronic acid Chemical compound O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-QIUUJYRFSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- DEKWSNGEGWMFGN-UHFFFAOYSA-N phenyl bis(4-phenylphenyl) phosphate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OP(OC=1C=CC(=CC=1)C=1C=CC=CC=1)(=O)OC1=CC=CC=C1 DEKWSNGEGWMFGN-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- 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
- C07F9/06—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2010-0067689 | 2010-07-14 | ||
| KR1020100067689A KR101381709B1 (ko) | 2010-07-14 | 2010-07-14 | 비페닐-4-일 디페닐 포스페이트 조성물의 제조방법 |
| PCT/KR2011/005138 WO2012008744A2 (en) | 2010-07-14 | 2011-07-13 | Method of preparing biphenyl-4-yl diphenyl phosphate composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013536166A true JP2013536166A (ja) | 2013-09-19 |
| JP2013536166A5 JP2013536166A5 (https=) | 2014-08-21 |
Family
ID=45469919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013519587A Pending JP2013536166A (ja) | 2010-07-14 | 2011-07-13 | ビフェニル‐４‐イルジフェニルホスフェート組成物の製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8742157B2 (https=) |
| EP (1) | EP2593464A4 (https=) |
| JP (1) | JP2013536166A (https=) |
| KR (1) | KR101381709B1 (https=) |
| TW (1) | TW201213341A (https=) |
| WO (1) | WO2012008744A2 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101384193B1 (ko) * | 2010-11-18 | 2014-04-10 | 에스케이이노베이션 주식회사 | 셀룰로오스 아실레이트 필름 |
| CN121427306B (zh) * | 2025-12-30 | 2026-04-24 | 广州辰东新材料有限公司 | 一种光致阻燃聚酰胺复合材料及其制备方法和应用 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197653A (ja) * | 1985-02-27 | 1986-09-01 | Mitsubishi Gas Chem Co Inc | 難燃性ポリフエニレンエ−テル系樹脂組成物 |
| JPH0441498A (ja) * | 1990-06-05 | 1992-02-12 | Lion Corp | リン酸エステルの製造方法 |
| WO2002100868A1 (en) * | 2001-06-08 | 2002-12-19 | Daihachi Chemical Industry Co., Ltd. | Process for preparation of phosphoric esters |
| US20030171463A1 (en) * | 2002-01-06 | 2003-09-11 | Bromine Compounds Ltd. | Preparation of phenylphosphate esters of 4,4'-biphenol |
| WO2006095658A1 (ja) * | 2005-03-11 | 2006-09-14 | Daihachi Chemical Industry Co., Ltd. | 難燃性ポリエステル繊維とその製造方法 |
| JP2007022925A (ja) * | 2005-07-12 | 2007-02-01 | Sanko Kk | オルソビフェニルジフェニルホスフェート組成物の製造方法 |
| JP2008044895A (ja) * | 2006-08-17 | 2008-02-28 | Fujifilm Corp | ｏ−ビフェニルジフェニルホスフェートおよびトリフェニルホスフェートの混合物の製造方法。 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1940222A (en) * | 1928-11-07 | 1933-12-19 | Jewell Electrical Instr Compan | Tube testing system |
| US2225285A (en) | 1938-08-11 | 1940-12-17 | Dow Chemical Co | Complex organic phosphate |
| US2656373A (en) | 1950-04-14 | 1953-10-20 | Monsanto Chemicals | Process for producing mixed diaryl esters of ortho-phosphoric acid |
| EP0595597A1 (en) * | 1992-10-28 | 1994-05-04 | Teijin Chemicals, Ltd. | Process for producing triaryl phosphate |
| US5914213A (en) * | 1996-11-27 | 1999-06-22 | Polaroid Corporation | Process and composition for generation of acid |
| US6204404B1 (en) * | 1997-06-06 | 2001-03-20 | Daihachi Chemical Industry Co., Ltd. | Process for preparing ester compounds |
| JP4297453B2 (ja) * | 2005-02-21 | 2009-07-15 | 富士電機ホールディングス株式会社 | 反応性難燃剤及びそれを用いた難燃性樹脂加工品 |
| US20100168299A1 (en) | 2005-03-11 | 2010-07-01 | Daihachi Chemical Industry Co., Ltd. | Flame-Retardant Polyester Fibers and Preparation Process Thereof |
-
2010
- 2010-07-14 KR KR1020100067689A patent/KR101381709B1/ko active Active
-
2011
- 2011-07-13 WO PCT/KR2011/005138 patent/WO2012008744A2/en not_active Ceased
- 2011-07-13 JP JP2013519587A patent/JP2013536166A/ja active Pending
- 2011-07-13 TW TW100124741A patent/TW201213341A/zh unknown
- 2011-07-13 EP EP11807029.1A patent/EP2593464A4/en not_active Withdrawn
- 2011-07-13 US US13/809,986 patent/US8742157B2/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197653A (ja) * | 1985-02-27 | 1986-09-01 | Mitsubishi Gas Chem Co Inc | 難燃性ポリフエニレンエ−テル系樹脂組成物 |
| JPH0441498A (ja) * | 1990-06-05 | 1992-02-12 | Lion Corp | リン酸エステルの製造方法 |
| WO2002100868A1 (en) * | 2001-06-08 | 2002-12-19 | Daihachi Chemical Industry Co., Ltd. | Process for preparation of phosphoric esters |
| US20030171463A1 (en) * | 2002-01-06 | 2003-09-11 | Bromine Compounds Ltd. | Preparation of phenylphosphate esters of 4,4'-biphenol |
| WO2006095658A1 (ja) * | 2005-03-11 | 2006-09-14 | Daihachi Chemical Industry Co., Ltd. | 難燃性ポリエステル繊維とその製造方法 |
| JP2007022925A (ja) * | 2005-07-12 | 2007-02-01 | Sanko Kk | オルソビフェニルジフェニルホスフェート組成物の製造方法 |
| JP2008044895A (ja) * | 2006-08-17 | 2008-02-28 | Fujifilm Corp | ｏ−ビフェニルジフェニルホスフェートおよびトリフェニルホスフェートの混合物の製造方法。 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2593464A2 (en) | 2013-05-22 |
| EP2593464A4 (en) | 2014-01-15 |
| WO2012008744A2 (en) | 2012-01-19 |
| KR20120007117A (ko) | 2012-01-20 |
| US8742157B2 (en) | 2014-06-03 |
| WO2012008744A3 (en) | 2012-04-26 |
| US20130178642A1 (en) | 2013-07-11 |
| KR101381709B1 (ko) | 2014-04-04 |
| TW201213341A (en) | 2012-04-01 |
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