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WO2007004731A1 - Cristal d'ester phosphite - Google Patents

Cristal d'ester phosphite Download PDF

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Publication number
WO2007004731A1
WO2007004731A1 PCT/JP2006/313633 JP2006313633W WO2007004731A1 WO 2007004731 A1 WO2007004731 A1 WO 2007004731A1 JP 2006313633 W JP2006313633 W JP 2006313633W WO 2007004731 A1 WO2007004731 A1 WO 2007004731A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
group
butyl
hydroxy
acid
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/JP2006/313633
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English (en)
Japanese (ja)
Inventor
Taketoshi Kikuchi
Toshiya Takahashi
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.)
Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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 Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of WO2007004731A1 publication Critical patent/WO2007004731A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07F9/547—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
    • 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
    • C08K5/524—Esters of phosphorous acids, e.g. of H3PO3

Definitions

  • An object of the present invention is to provide crystals of phosphite esters that, when blended in a thermoplastic resin, have little effect on the hue of the thermoplastic resin and are less likely to cause blocking during drying or storage.
  • the present invention provides the following [1] to [4].
  • R 1 R 2 , R 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, an alkyl cyclohexane having 6 to 12 carbon atoms, Represents an alkyl group, an aralkyl group or a phenyl group having 7 to 12 carbon atoms, R 3 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, X represents a single bond, a sulfur atom or one CHR 6 — group, wherein R 6 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or Represents a cycloalkyl group having 5 to 8 carbon atoms, A represents an alkylene group having 2 to 8 carbon atoms or * one COR 7 — group, wherein R 7 is a single bond or an alkylene having 1 to 8 carbon atoms.
  • Y and Z each represents a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, or an aralkyloxy group having 7 to 12 carbon atoms.
  • the other represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • R 1 , R 2 , R 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, or 6 to 12 carbon atoms.
  • the substituents R 1 , R 2 , R 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl having 5 to 8 carbon atoms.
  • R 1 , R 2 , R 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl having 5 to 8 carbon atoms.
  • RR 2 and R 4 are preferably an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, and an alkylcycloalkyl group having 6 to 12 carbon atoms, and R 5 is a hydrogen atom, C1-C8 alkyl group, C5-C8 cycloalkyl It is preferable that it is a group.
  • X is preferably a simple bond, a methylene group or a methylene group substituted by methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl or the like.
  • Substituent A is an alkylene group having 2 to 8 carbon atoms or * —COR 7 — group (R 7 is a simple bond or an alkylene group having 1 to 8 carbon atoms, and * is bonded to the oxygen side. Represents).
  • * indicates that the force ligand is bonded to the phosphate oxygen.
  • Typical examples of the alkylene group having 1 to 8 carbon atoms in R 7 include methylene, ethylene, propylene, butylene, pentamethylene, hexamethylene, octamethylene, 2,2 dimethyl-1,3-propylene, and the like.
  • R 7 is preferably a simple bond, ethylene or the like.
  • amides include N, N-dimethylformamide and N, N-dimethylacetamide, and N, N-dimethylformamide is preferably used.
  • hydroxide of the Al-strength metal or the al-strength earth metal examples include sodium hydroxide and calcium hydroxide.
  • Sodium hydroxide is preferable.
  • the reaction is usually performed in an organic solvent.
  • Such an organic solvent is not particularly limited as long as it does not inhibit the reaction, and examples thereof include aromatic hydrocarbons, aliphatic hydrocarbons, oxygen-containing hydrocarbons, and halogenated hydrocarbons.
  • bisphenols (II) examples include 2 methylene bis (4 1 methyl 1 6-t 1 butyl phenol), 2, 2 '(4 1 ethyl 1 6 1 t 1 butyl phenol), 2, 2' 1 (4 — N-Propyl 6-t-Butylphenol), 2, 2 '-(4-I-Propyl _ 6-t-Butylphenol), 2, 2'-(4 n-Butyl-6-t-Ptylphenol) ), 2, 2 '-(4- i -butyl-6 1 t-butylphenol) 2, 2'-(4, 6 -di-t-butylphenol) 2 2, (4 1 t pentyl 6-t 1 butyl) (Lephenol) 2 2, (4-Nonyl 6-t-butylphenol) 2, 2 (4 t-octyl-6-t-butylphenol) 2, 2 (4-Methyl-6-t-pentylphenol), 2 2 , (4-Methyl-6-cyclo
  • examples of the reducing agent include aluminum lithium hydride and aluminum.
  • R 7 When R 7 is a simple bond, it can be produced, for example, by subjecting the corresponding hydroxybenzoic acid, alkoxybenzoic acid, aralkyloxybenzoic acid, or the like to a Friedel-Craft reaction using a catalyst such as aluminum chloride or zinc chloride. it can.
  • Z when Z is a hydroxy group, an alkoxy group or an aralkyloxy group, Kolbe-Schmidt is used by using a corresponding phenol, an alkali metal hydroxide such as sodium hydroxide or hydroxy hydroxide and carbon dioxide. It can be produced by reacting (see Japanese Patent Application Laid-Open No. 6 2-6 1 94 9 and Japanese Patent Application Laid-Open No. 6 3-1 65 3 4 1).
  • R 7 is an alkylene having 1 to 8 carbon atoms
  • the corresponding phenol was asilated using a Friedel-Crafts catalyst such as aluminum chloride or zinc chloride, or a strong alkoxyalkanoyl halogenoid. Thereafter, it can be produced by reducing the carbonyl group at the benzyl position to an alkylene with a hydrogenation catalyst such as palladium charcoal or white gold charcoal, and then hydrolyzing the ester with acid or alcohol ( Rubber Chemistry and Technology 4 6, 9 6 (see 1 9 7 3)).
  • a Friedel-Crafts catalyst such as aluminum chloride or zinc chloride, or a strong alkoxyalkanoyl halogenoid.
  • a hydrogenation catalyst such as palladium charcoal or white gold charcoal
  • the hydrohalide salt of the dehydrohalogenating agent produced by the reaction is removed by washing with water, and the solvent is distilled off, and then the crystallization solvent is removed.
  • the phosphite esters (I) of the present invention can be obtained by cooling and crystallization.
  • the cooling crystallization includes, for example, the first step of precipitating a part of the phosphite ester (I) by cooling a solution containing the crude phosphite ester (I) and the crystallization solvent such as the above reaction solution.
  • tau represents the lowest value of the liquid temperature in the first step a (° c)
  • ⁇ 2 represents the maximum value of the liquid temperature in the second step the (° c)
  • ⁇ 3 is the liquid temperature in the third step Represents the minimum value (° C).
  • the crystallization solvent aliphatic hydrocarbons having a boiling point of 150 ° C. or lower and Z or alicyclic hydrocarbons are used, preferably having a boiling point of 30 to 120 ° C., particularly preferably having a boiling point of 30. ⁇ 1 0 0 ° C. (Hereinafter, aliphatic hydrocarbons having a boiling point of 150 ° C.
  • the crystallization solvent may be added in a state in which the reaction solvent is slightly left, but normally, the reaction solvent is 10% by weight with respect to 100 parts by weight of the phosphites. Part or less, preferably 5 parts by weight or less. When the amount of the reaction solvent exceeds 10 parts by weight, the crystallization yield is lowered, which is not preferable.
  • n-pentane (boiling point) is used as an aliphatic hydrocarbon having a boiling point of 150 ° C or lower. Point 3 6 ° C), n-hexane (boiling point 6 9 ° C), n-heptane (boiling point 98 ° C), n-octane (boiling point 1 26 ° C), etc.
  • alicyclic hydrocarbons at 0 ° C or lower include cyclopentane (boiling point 49 ° C), cyclohexane (boiling point 81 ° C), cycloheptane (boiling point 1 17 ° C), and the like. It is done.
  • the contained hydrocarbons may be different kinds of contained hydrocarbons.
  • the containing hydrocarbons as a crystallization solvent, crystals of phosphites (I) with high purity and high yield can be obtained.
  • thermoplastic resin will tend to deteriorate even if the crystal of the present invention is added to the thermoplastic resin. is there.
  • the amount of the crystallization solvent used is that the concentration of the phosphite ester (I) solution is 10 to 60% by weight, preferably 20 to 55% by weight when cooling and crystallization is carried out batchwise. The amount is adjusted to%.
  • the solution is cooled below the temperature (saturation temperature) at which the esters (I) are precipitated as crystals from a solution containing the phosphites (I) and the crystallization solvent. A part of crystals of the ester (I) is precipitated.
  • the minimum temperature (minimum liquid temperature (° C)) in the first process is 1.
  • the precipitation rate of phosphites (I) at temperature 1 is preferably in the range of 5 to 60 parts by weight when the total amount of the esters in the solution (I) is 100 parts by weight. More preferably, it is in the range of 10 to 40 parts by weight.
  • the above temperature varies depending on the solution concentration of the phosphites (I), but is usually not higher than the saturation temperature, and preferably in the range of 20 to 50 ° C.
  • seed crystals of phosphites (I) may be added as necessary.
  • the temperature is kept below the temperature for 30 minutes to 3 hours.
  • the slurry is heated from the slurry containing the crystals of the phosphites (I) precipitated in the first step until a part of the crystals is dissolved.
  • the slurry is heated to below the temperature at which a saturated solution of the phosphites (I) is formed.
  • Maximum temperature (liquid highest temperature (in)) of the slurry in the second step is T 2.
  • the crystal remaining in the slurry is in the range of 5-4 0 parts by weight Is preferable, and the range of 10 to 35 parts by weight is more preferable.
  • the second step it is preferable to keep the temperature at a temperature of less than 2 for 30 minutes to 3 hours.
  • the slurry containing the crystals of the phosphites (I) remaining in the second step and the crystallization solvent is cooled and crystallized.
  • T 3 Minimum temperature (minimum value of the liquid temperature (at)) in the third step is T 3.
  • T 3 is usually a crystallization solvent melting point or more and less than 1 ⁇ , specifically, is an 2 0 ⁇ 1 0 ° C.
  • Cooling rate to T 2 or we T 3 it is good Mashiku a hour 2 0 ° C or less speed, more preferably per hour 1 5 ° C below the speed, the following hour 1 0 ° C Particularly preferred is speed.
  • the cooling rate during crystallization is 20 ° C or less per hour
  • the crystals of phosphites (I) tend to be large and the fluidity tends to be improved.
  • a crude wet crystal (wet cake) is obtained by filtering the slurry containing the phosphites (I) and the crystallization solvent produced by cooling crystallization.
  • the first carried out to third step after holding the slurry obtained in the third step at a temperature T 3, and filtered at the same temperature, the crude wet crystals of the phosphite esters (wet cake) Get.
  • a filtration method for example, separation is performed by a normal separation means such as pressure filtration, vacuum filtration, centrifugal filtration, or the like. In this way, the wet wet crystals containing 3 to 20 parts by weight of hydrocarbons in 100 parts by weight of the crystals of phosphites (I) can be obtained.
  • the wet crystals can be washed with a hydrocarbon containing the same.
  • a solvent other than the hydrocarbon containing water, aromatic hydrocarbon, alcohol, etc. may be contained in the wet crystal, but usually 1 wt. Part or less, preferably 0.1 part by weight or less, and particularly preferably, it is preferably substantially free of content. If the content of the solvent other than the contained hydrocarbons is 1 part by weight or less, it tends not to solidify during drying, it is difficult to block the obtained crystals when stored, or the obtained crystals are heated. Even if blended with a plastic resin, it is preferable because coloring of the thermoplastic resin tends to be reduced.
  • the wet crystal can be dried using a dryer under the conditions shown below to obtain the crystal of the present invention (dried product).
  • the drying pressure is set to a vacuum of 5 to 20 kPa, the crystals are not heated to a high temperature or dried over time, and the obtained dried crystals are heated even when blended with a thermoplastic resin. This is preferable because coloring of the plastic resin tends to be reduced.
  • thermoplastic resin when the drying temperature is 40 to 60 ° C. using a heating medium, coloring of the thermoplastic resin tends to be reduced even if the obtained dry crystals are blended with the thermoplastic resin. This is preferable.
  • the drying pressure is set to less than 5 kPa, the crystal having excellent quality can be obtained in the same manner as in the present invention.
  • a special vacuum is used. Equipment is required, which is not preferable from the viewpoint of industrial productivity and economy.
  • the drying pressure exceeds 20 kPa, the drying is insufficient and blocking occurs during drying or storage.
  • the drying temperature is less than 40 ° C, drying may be insufficient and may block during drying or storage.
  • the hue of the thermoplastic resin may deteriorate when used as a thermoplastic resin.
  • the drying conditions of the present invention can be carried out at a drying pressure of 5 to 20 kPa and a drying temperature of 40 to 60 ° C. At this time, the drying pressure is first set at room temperature.
  • a method is preferred in which the temperature is set to 40 to 60 ° C. and heated after the vacuum is set to 5 to 20 kPa. If the temperature is raised prior to depressurization, the hue of the thermoplastic resin may be deteriorated if the crystal is applied to a blocking or thermoplastic resin during drying.
  • the present invention may be dried in a stationary state or may be dried while rotating the dryer. However, drying while rotating is preferable from the viewpoint of suppressing caking during drying. Specific examples of rotary dryers include conical dryers and now evening dryers.
  • stationary dryers include ovens and vibrations
  • fluidized dryers In 100 parts by weight of the crystal of the present invention thus obtained, the content of the hydrocarbons contained is 0.005 to 0.3 parts by weight, preferably 0.01 to 0.2 parts by weight, more preferably Is 0.04 to 0.12 parts by weight.
  • the amount is 0.005 parts by weight or more, it is preferable because the coloring of the thermoplastic resin tends to be reduced even when blended with the thermoplastic resin, and when the amount is 0.3 parts by weight or less, blocking occurs during drying or storage. It is preferable because it tends to suppress the above.
  • the crystals of the phosphites (I) of the present invention have little effect on the hue of the thermoplastic resin when blended with a thermoplastic resin, and are less likely to cause blocking during drying or storage.
  • n-heptane content in the wet crystal was measured by gas chromatography (in the following Examples and Comparative Examples, the residual solvent was quantified by gas chromatography) and found to be 13% by weight.
  • the wet crystals were washed with n-heptane to obtain wet crystals.
  • the sample was dried for 15 hours at a jacket inlet temperature of 50 ° C. under a vacuum of 6.6 kPa using a stainless steel jacketed vacuum dryer having a capacity of 2 m 3 .
  • the content of n-heptane (boiling point 98 ° C) in the dioxaphosphepine crystals after drying is 0.12 % By weight.
  • Example 2 The same operation as in Example 1 was conducted except that n-decane (boiling point: 174 ° C) was used as a solvent for crystallization and washing instead of n-heptane. The results are shown in Table 1 together with Example 1. Comparative Example 2
  • Example 3 Except that the wet crystals were first set in a rotary evaporator at a vacuum of 19 k Pa, and then immersed in a hot water bath with a bath temperature of 50 ° C while rotating the flask and dried for 45 minutes. The same operation as in Example 1 was performed. The results are summarized in Table 1. Even when the obtained dioxaphosphepine crystals were stored at 50 ° CX 80% RH for 4 days, no solidification (blocking) occurred.
  • Example 3 Even when the obtained dioxaphosphepine crystals were stored at 50 ° CX 80% RH for 4 days, no solidification (blocking) occurred.
  • Example 2 In the same manner as in Example 1, coarse wet crystals were obtained. Next, wet crystals were obtained in the same manner as in Example 1 except that washing was performed using n-hexane instead of n-heptane, and then a rotary evaporator was used, and a vacuum at a pressure of 19 kPa was used. The bath temperature was set to 40 ° C. and dried for 30 minutes to obtain dioxaphosphepine crystals. The results are summarized in Table 2 together with Example 2. Comparative Example 3
  • Example 2 The same operation as in Example 2 was performed except that the bath temperature was set to 98 ° C. under a vacuum of 91 kPa and dried for 45 minutes. The results are summarized in Table 2. Comparative Example 4
  • Example 1 Comparative Example 3, Comparative Example 4, Dioxaphosphepine 5 Omg and Low Density Polyethylene 50 g obtained in Labo Plast Mill were put into a Laboplast Mill, and conditions for 50 revolutions Z at 200 ° C And kneaded for 30 minutes. After kneading for 30 minutes, pressing was performed, and the yellowness index (Y I) of the hue of the press sheet was measured with a color computer to evaluate the color resistance during resin processing. Furthermore, the torque during kneading was tracked and the torque rise start time was measured. The longer the torque rise start time, the better the heat stabilization effect. The results are summarized in Table 3. Table 3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un cristal d'un ester phosphite comprenant au moins un hydrocarbure choisi dans le groupe comprenant un hydrocarbure aliphatique ayant un point de fusion inférieur ou égal à 150 °C et un hydrocarbure aliphatique ayant un point d'ébullition inférieur ou égal à 150 °C, la teneur en hydrocarbure étant de 0,005 à 0,3 partie en poids pour 100 parties en poids du cristal.
PCT/JP2006/313633 2005-07-05 2006-07-04 Cristal d'ester phosphite Ceased WO2007004731A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005-195826 2005-07-05
JP2005195826 2005-07-05

Publications (1)

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WO2007004731A1 true WO2007004731A1 (fr) 2007-01-11

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WO (1) WO2007004731A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1921083A1 (fr) * 2006-11-10 2008-05-14 Sumitomo Chemical Company, Limited Composition de phosphite et procédé de production de celle-ci
US8471005B2 (en) 2008-12-19 2013-06-25 Cephalon, Inc. Pyrrolotriazines as ALK and JAK2 inhibitors

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1059988A (ja) * 1996-06-19 1998-03-03 Hoechst Ag ２，２’，２”− ニトリロ（トリエチルトリス（３，３’，５，５’−テトラ− 第三ブチル−１，１’−ビフェニル−２，２’−ジイル） ホスファイト） の製造方法
JP2004331584A (ja) * 2003-05-08 2004-11-25 Sumitomo Chem Co Ltd 亜リン酸エステル類の製造方法
JP2005200325A (ja) * 2004-01-14 2005-07-28 Sumitomo Chemical Co Ltd 亜リン酸エステル類結晶の製造方法
JP2005200326A (ja) * 2004-01-14 2005-07-28 Sumitomo Chemical Co Ltd 亜リン酸エステル類の製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004149472A (ja) * 2002-10-31 2004-05-27 Sumitomo Chem Co Ltd 亜リン酸エステル類の結晶、及びその製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1059988A (ja) * 1996-06-19 1998-03-03 Hoechst Ag ２，２’，２”− ニトリロ（トリエチルトリス（３，３’，５，５’−テトラ− 第三ブチル−１，１’−ビフェニル−２，２’−ジイル） ホスファイト） の製造方法
JP2004331584A (ja) * 2003-05-08 2004-11-25 Sumitomo Chem Co Ltd 亜リン酸エステル類の製造方法
JP2005200325A (ja) * 2004-01-14 2005-07-28 Sumitomo Chemical Co Ltd 亜リン酸エステル類結晶の製造方法
JP2005200326A (ja) * 2004-01-14 2005-07-28 Sumitomo Chemical Co Ltd 亜リン酸エステル類の製造方法

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KOJIMA F. ET AL.: "Kobunshiyo Tenkazai 'Sumilizer G Series' no Tenkai", SUMITOMO KAGAKU, no. 1, 2004, pages 24 - 30, XP003008849 *
KOJIMA F. ET AL.: "Shinki Koseino Kako Anteizai no Kaihatsu -Sumilizer GP-", SUMITOMO KAGAKU, no. 2, 2002, pages 42 - 49, XP009035711 *
ODORISIO P. ET AL.: "12H-DIBENZO[d,g][1,3,2]DIOXAPHOSPHOCINS: synthesis and evidence for long-range coupling to phosphorus", PHOSPHORUS AND SULFUR AND THE RELATED ELEMENTS, vol. 15, no. 1, 1983, pages 9 - 13, XP003008848 *
REETZ M.T. ET AL.: "Mixtures of chiral and achiral monodentate ligands in asymmetric Rh-catalyzed olefin hydrogenation: reversal of enantioselectivity", TETRAHEDRON LETTERS, vol. 44, no. 24, 2003, pages 4593 - 4596, XP004425274 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1921083A1 (fr) * 2006-11-10 2008-05-14 Sumitomo Chemical Company, Limited Composition de phosphite et procédé de production de celle-ci
US7683112B2 (en) 2006-11-10 2010-03-23 Sumitomo Chemical Company, Limited Phosphite composition and method for producing the same
US8471005B2 (en) 2008-12-19 2013-06-25 Cephalon, Inc. Pyrrolotriazines as ALK and JAK2 inhibitors

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JP2007039447A (ja) 2007-02-15
JP5167600B2 (ja) 2013-03-21

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