WO2006006511A1 - ポリエーテルの製造方法 - Google Patents
ポリエーテルの製造方法 Download PDFInfo
- Publication number
- WO2006006511A1 WO2006006511A1 PCT/JP2005/012637 JP2005012637W WO2006006511A1 WO 2006006511 A1 WO2006006511 A1 WO 2006006511A1 JP 2005012637 W JP2005012637 W JP 2005012637W WO 2006006511 A1 WO2006006511 A1 WO 2006006511A1
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- WO
- WIPO (PCT)
- Prior art keywords
- polyether
- water
- producing
- crude
- soluble compound
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
Definitions
- the present invention relates to a polyether containing a water-soluble compound (hereinafter referred to as crude polyether) force, and a method for producing a polyether comprising a step of extracting and removing the water-soluble compound with water. .
- These polymer substances are usually obtained by purifying a polymer substance containing impurities (crude polymer substance) to remove impurities.
- One of the impurities contained in such a crude polymer substance is an alkali metal compound or a metal compound resulting from a complex metal cyanide complex, and examples thereof include the following.
- a double metal cyanide complex catalyst is used as a catalyst, and this is used as it is or as a modified decomposition product in a polymer material produced. Remain.
- an alkali metal compound such as sodium hydroxide or potassium hydroxide is used as a catalyst, which is used as it is or as a salt. It remains in the polymer material that forms.
- a polymer having a functional group such as an oxyalkylene polymer having a hydroxyl group or a carboxyl group or a gen-based polymer with a halogen-containing compound such as epichlorohydrin or salt allyl.
- a halogen-containing compound such as epichlorohydrin or salt allyl.
- an alkali metal compound such as sodium hydroxide or potassium hydroxide is used as a catalyst and remains in the polymer material generated as it is or as a salt. To do.
- impurities are often removed by a method such as adsorbent treatment, filtration after neutralization, and extraction with water.
- the method of treating with an adsorbent is not suitable for treating a large amount of metal compound, and there are problems that the number of adsorbents that can be used is small when the metal compound is a salt. is there.
- the method using filtration has problems that it is necessary to increase the crystal size of neutralized salts, and that salt dissolves in the presence of water.
- the extraction / separation method is a method in which a crude polymer substance and water are brought into good contact to move a metal compound into water as a water-soluble salt, and then the polymer substance and water are separated.
- Patent Documents 1 and 2 states that “polyether produced using a composite metal cyanide complex catalyst is very easy to emulsify with water, and thus is very difficult to remove by extraction”.
- a production method using a highly versatile purification method is not limited to high-molecular weight polyethers having the above-described properties, not limited to unsaturated group-containing polyethers. It is hoped that it will be established.
- Patent Document 3 a method by centrifugation is disclosed in order to actively promote oil-water separation.
- a continuous counter-current extraction tower such as a spray tower, a stirring type, and a reciprocating type and a centrifugal separator are used and disclosed (Patent Documents 1 and 3).
- polyether and water as polymers are agitated in a high-speed agitation type agitation tank having agitation blades, and then the centrifuge and the countercurrent contact type agitation tower are used to filter the polymer.
- a method for separating the ether phase and the aqueous phase is provided.
- it is considered that there is a need for improvement because it is necessary to use a filter or a stirring tank with high-speed stirring and an expensive centrifuge.
- the initiator may contain a polymerized portion of ethylene oxide. If the monomer contains ethylene oxide as an impurity, the hydrophilicity of the polymer from which these monomers are obtained may increase, making extraction separation using water extremely difficult. In order to avoid such a situation, there is a problem that it is necessary to strictly control the content of ethylene oxide in the initiator and the content of ethylene oxide in the monomer.
- Patent Document 1 Japanese Patent Laid-Open No. 2002-249580
- Patent Document 2 JP-A-8-231707
- Patent Document 3 Japanese Patent Laid-Open No. 1-294733
- An object of the present invention is to improve the separability between the polyether phase and the aqueous phase when the water-soluble compound is extracted from the polyether containing the water-soluble compound with water and then removed.
- the object is to provide a method for producing ethers. Means for solving the problem
- the present invention is a method for producing a polyether, comprising a step of extracting a water-soluble compound with water (crude polyether) and extracting the water-soluble compound with water.
- the present invention relates to a method for producing a polyester, which includes at least an operation of separating an aqueous phase at a temperature of 50 ° C. or higher.
- the temperature at which the polyether phase and the aqueous phase are separated is preferably 60 to 140 ° C.
- the amount of water added in the step of extracting and removing the crude polyether strength water-soluble compound with water is preferably 20 to: LOO parts by weight with respect to 100 parts by weight of the crude polyether.
- the operation for separating the polyether phase and the aqueous phase after extraction is preferably an operation by a stationary separation method or a centrifugal separation method.
- the temperature during the extraction of the mixture of the crude polyether and water is preferably 60 to 140 ° C.
- Crude polyether force The present invention can be more preferably applied to a hydroxyl group-containing polyether obtained by reacting an alkylene oxide with an initiator in the presence of a metal catalyst or a modified product thereof.
- the present invention is effective when 90% by weight or more of the alkylene oxide is an alkylene oxide having 3 or more carbon atoms, and can be preferably applied when the alkylene oxide is propylene oxide.
- unsaturated group-containing polyether can be mentioned.
- the main chain skeleton is alkylene in the presence of a complex metal cyanide complex compound catalyst.
- a polyether obtained by reacting an oxide was mentioned.
- an alkylene oxide was reacted with an initiator in the presence of a double metal cyanide complex compound catalyst to obtain a hydroxyl group-containing polyether.
- an unsaturated group-containing polyether obtained by reacting an unsaturated group-containing halogenated hydrocarbon with the hydroxyl group-containing polyether as an alkali metal alkoxide is mentioned.
- an aryl group is exemplified.
- the water-soluble compound referred to in the present invention is not particularly limited, but impurities such as zinc salts, cobalt salts and alkali metal salts derived from the catalyst used in the polymerization of the polyether are not particularly limited. The present invention is preferably applied to the removal.
- the present invention is particularly suitable when the number average molecular weight of the polyether is 1000 to 100000.
- a polyether having an extremely low content of water-soluble compounds such as an inorganic salt content of a basic alkali metal compound and an acid or a metal salt derived from a composite metal cyanide complex catalyst is obtained. Simple device and can be obtained in a short time. In addition, when the polyether thus obtained is used as a raw material, a high-quality polyether can be stably produced.
- the crude polyether containing the water-soluble compound in the present invention is not particularly limited, and any crude polyether can be used.
- the crude polyether, that is, the oxyalkylene polymer containing the water-soluble compound may be a homopolymer having one repeating unit force or a copolymer. Moreover, the polymer may be reacted and converted into another polymer.
- the oxyalkylene-based polymer mainly has repeating units represented by R—O (preferably 50% (% by weight, the same applies hereinafter) in the total polymer, more preferably 80% or more).
- R—O preferably 50% (% by weight, the same applies hereinafter
- R- for example, — CH CH, CH (CH) CH —, — CH
- the polyether has a number average molecular weight of 1000 to 100,000 in terms of polystyrene in gel “permeation” chromatography (GPC). Even if the number average molecular weight is less than 1000 or more than 100000, sufficient separation between the polyether phase and the aqueous phase may not be obtained.
- the oxyalkylene polymer may have a terminal hydroxyl group, but after the hydroxyl group-containing polyether is reacted with an alkali metal compound to convert the terminal, An unsaturated group-containing polyether obtained by reacting an unsaturated group-containing halogenated hydrocarbon may also be used.
- Examples of unsaturated group-containing halogenated hydrocarbons include polyhalogenated unsaturated hydrocarbons having 4 or less carbon atoms, or monohalogenated unsaturated hydrocarbons having 10 or less carbon atoms.
- halogen chlorine or bromine is preferable, and alkenyl chloride and alkyl bromide are particularly preferable.
- alkenyl chloride and alkyl bromide are particularly preferable.
- halogen alcohol salt aryl, methallyl chloride or allyl bromide is particularly preferable.
- the water-soluble compounds to be removed in the polyether are derived from alkali metal compounds or composite metal cyanide complex catalysts such as zinc salts, cobalt salts and Z or alkali metal salts.
- alkali metal compounds or composite metal cyanide complex catalysts such as zinc salts, cobalt salts and Z or alkali metal salts.
- a compound etc. can be illustrated.
- An alkali metal compound is a compound used as a catalyst for polymerization or a reaction for modifying a polyether or the like and remains in the crude polyether as it is or as another compound. .
- metal compounds such as alkali metal compounds include alkali metals such as Na and K; alkali metal hydrides such as NaH; and al forces such as NaOCH and NaOC H.
- Li-metal alkoxides such as sodium hydroxide and potassium hydroxide; HCO ONa, CH COONa, C H COONa, HCOOK, CH COOK, C H COOK, etc.
- Alkali metal organic acid salts of organic acids such as carboxylic acids; NaCl, Na 2 SO 4, Na 2 CO 3, NaH
- HPO HPO
- KNO hydrogen halides
- sulfuric acid sulfuric acid and other alkali metal inorganic salts.
- Na, K, and the like are alkali metals, they are considered as a kind of alkali metal compounds in this specification.
- the composite metal cyanide complex catalyst includes a complex compound mainly composed of zinc hexanocobaltate, and its ether complex compound is well known. Yes. Its composition is For example, those described in US Pat. No. 3,427,256 can be used. Examples of ethers include ethylene glycol dimethyl ether (glyme).
- the present invention is very surprising that a good polyether can be obtained by simply stirring and mixing the crude polyether as the oil phase and the water added as the aqueous phase and then bringing the temperature to 50 ° C or higher. It was clarified that oil-water separation between the ether phase and the aqueous phase could be confirmed.
- the stirring and mixing time described above is easy to understand if it is a batch type stirring tank, but means an average residence time in the case of a continuous stirring tank.
- the average residence time in this case is defined as (continuous system volume) / (average processing flow rate).
- the temperature at which the polyether phase and the aqueous phase are separated is preferably 50 ° C or higher. More preferably, it is 60 ° C or higher from the viewpoint of separability, and a higher value is preferable. However, if the temperature exceeds 140 ° C, the polymer may be degraded.
- the temperature at the time of extraction prior to the separation is preferably matched with the separation temperature of the polyether phase and the aqueous phase, and is preferably 60 to 140 ° C. Also, a higher temperature is preferable because the extraction speed can be increased.
- the amount of water added in the step of extracting and removing the water-soluble compound from the crude polyether carbonate with water is preferably 20 to LOO parts by weight with respect to 100 parts by weight of the crude polyether.
- an organic solvent in order to improve oil-water separation. This means that it is not necessary to distill off the organic solvent in the subsequent process, which is one of the major features of this patent.
- an organic solvent can be added. The added amount is preferably 1 part by weight or more with respect to 100 parts by weight of the crude polyether in order to obtain the above effect, but it is limited to 50 parts or less in order not to raise the vapor pressure at the extraction temperature too much. It is preferable. Addition of an organic solvent more than necessary leads to an increase in the cost of the extraction apparatus, which is not practically preferable.
- Examples of the organic solvent as described above include aliphatic, alicyclic or aromatic hydrocarbon solvents, ether solvents, and halides thereof. Specific examples thereof include butanes, pentanes, hexanes, heptanes, octanes, nonanes, decanes, dodecanes, cyclohexane, cyclopentane, benzene, toluene, xylenes, butanol.
- Pentanol methyl ether, ethyl ether, isopropyl ether, methylene chloride, methyl chloroform, carbon tetrachloride, dichlorodifluoromethane, perchloroethylene, chlorine atom, bromine atom and / or iodine atom
- Benzene-based solvents and toluene-based solvents are not limited to these. These may be used alone or in combination of two or more. The most preferred example is n-xane.
- the use ratio of the crude polyether and water is not particularly limited, but 20 to LOO parts by weight of water is preferable with respect to 100 parts of the crude polyether for the following reasons. If the amount of water is small, it is necessary to repeat extraction and aqueous phase separation in order to satisfy the required purification level. However, in the case of Notch type extraction, this method is preferable from the viewpoint of tank capacity. In addition, when the amount of water used is less than 20 parts by weight, almost all of the water is dissolved or finely dispersed in the oil phase and tends to be separated. On the other hand, if the amount of water is large, the number of extractions and aqueous phase separations described above can be reduced. However, the batch method is unsuitable industrially because the container is large, and is rather suitable for the continuous method. Which one to choose can be determined by other constraints that are realistic.
- the oil-water separation method is a method of static separation after stirring is stopped in a stirring tank, or a mixer Z-settler type method or centrifugal separation in which a treatment liquid discharged from the stirring tank is separated in the static tank.
- General oil-water separation system power can be selected, such as a method using a machine.
- the purified polymer obtained by such an oil-water separation method is dissolved in the polymer.
- the slightly dispersed aqueous phase can be removed by devolatilization using a vacuum pump or the like while heating to about 80 to 130 ° C, and can be used for the next reaction.
- Purified polyether can be easily obtained.
- Propylene oxide was polymerized with zinc hexanocobaltate complex catalyst using a mixture of polypropylene glycol having a molecular weight of 2000 and polypropylene triol having a molecular weight of 3000 in the same weight as an initiator to obtain a hydroxyl-terminated polyether oligomer. Subsequently, a methanol solution of sodium methoxide was added to the hydroxyl group-terminated polyether oligomer to distill off the methanol, and 3-chloro-one-propene was added to remove the terminal hydroxyl group. Conversion to the base gave crude polyether A. The number average molecular weight of Polyether A in terms of polystyrene in GPC was 19000.
- Polypropylene glycol having a molecular weight of 3000 (actol MF-78 manufactured by Mitsui Takeda Co., Ltd.) was used as an initiator to polymerize propylene oxide with a zinc hexanocobaltate complex catalyst to obtain a polyether oligomer B terminated with a hydroxyl group. .
- the number average molecular weight of polyether oligomer B in terms of polystyrene in GPC was 19000.
- the 1H—N MR spectrum was measured, it contained about 6% by weight of ethylene oxide polymer! The reason why the polymer content of ethylene oxide was about 6% by weight is not strong, but is thought to be derived from impurities in the initiator or propylene oxide monomer.
- the amount of the aqueous phase after the separation was 0.095, 0.12 1, 0.127, 0.127 kg in order of decreasing temperature, which is a good separation amount almost the same as the charged ion-exchanged water. It was. This result shows that oil-water separation can be performed efficiently at these temperatures.
- the difference between 0.156 kg of the charged amount of ion-exchanged water and the separated amount is the amount dissolved in the polyether phase, the amount dispersed, and the amount deposited on the apparatus wall.
- Example 1 when the extraction temperature was 90 ° C from the beginning, that is, when 90 ° C polyether and 90 ° C ion-exchanged water were mixed, the stirring start force was good after 10 minutes when stirring was stopped. Interface was observed. The amount of separated water at that time was 0.127 kg, which was the same as that at the separation temperature of 90 ° C. in Example 1.
- Example 2 the mixture of the polyether phase and the aqueous phase, which had a good oil / water interface, was transferred to a glass separatory funnel. As a result, the oil-water interface became almost invisible.
- Example 1 From the initial stage of stirring at 20 ° C to a temperature of 40 ° C or lower during the temperature rise, the interface between the separated polyether phase and the aqueous phase becomes harder to confirm as the temperature is lower. And at 30 ° C it was a force that did not exist at all. A little water phase was observed at 40 ° C, and the amount of water phase after separation was 0.075 kg, which was very small compared to the amount at a separation temperature of 50 ° C or higher.
- Example 1 the same procedure was performed except that the amount of ion-exchanged water was set to 0.039 kg (10 parts relative to 0.39 kg of crude polyether), and the temperature was raised to 40 to 90 ° C. As a result, the oil phase and the aqueous phase were not separated at any temperature, and the entire surface was cloudy.
- the amounts of water and hexane in Table 1 are parts by weight with respect to 100 parts by weight of the polyether used, and the EO content (the amount of ethylene oxide polymer) is expressed in wt% based on the weight of the polyether. ing.
- the stirring time was about 20 minutes and the rotation speed was 600 rpm. (600rpm is quite powerful stirring)
- Example 3 6 8 0 0 0 8 5 1 2 0
- Example 4 6 5 0 0 0 6 0 ⁇ 1 5 0
- Example 7 0 2 3 0 0 0 5 0 ⁇ 5 0
- Implementation Example 9 0 2 3 0 0 5 0 5 0 ⁇ 5 0
- Example 10 0 6 1 0 0 0 1 0 0 5 0> 1 0 0
- Example 1 1 0 2 1 0 0 0 1 0 0 5 0> 1 0 0
- Example 12 6 5 0 0 0 5 0 6 0 2 0 0
- Example 13 6 5 0 0 0 1 5 0 0 6 0 4 0 0 Comparative Example 4
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Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006528991A JP5009620B2 (ja) | 2004-07-13 | 2005-07-08 | ポリエーテルの製造方法 |
EP05765550.8A EP1767563B1 (en) | 2004-07-13 | 2005-07-08 | Method for producing polyether |
US11/631,028 US8367876B2 (en) | 2004-07-13 | 2005-07-08 | Method for producing polyether |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2004-206533 | 2004-07-13 | ||
JP2004206533 | 2004-07-13 |
Publications (1)
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WO2006006511A1 true WO2006006511A1 (ja) | 2006-01-19 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2005/012637 WO2006006511A1 (ja) | 2004-07-13 | 2005-07-08 | ポリエーテルの製造方法 |
Country Status (4)
Country | Link |
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US (1) | US8367876B2 (ja) |
EP (1) | EP1767563B1 (ja) |
JP (1) | JP5009620B2 (ja) |
WO (1) | WO2006006511A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008050417A (ja) * | 2006-08-22 | 2008-03-06 | Kaneka Corp | ポリエーテルの製造方法 |
JP2010254981A (ja) * | 2009-03-31 | 2010-11-11 | Nof Corp | 高分子量ポリエチレングリコール化合物の精製方法 |
WO2014157117A1 (ja) * | 2013-03-27 | 2014-10-02 | 日油株式会社 | アミノ基を一つ有するポリエチレングリコールの精製方法 |
JP2015189915A (ja) * | 2014-03-28 | 2015-11-02 | 三菱化学株式会社 | ポリエーテルポリオールの製造方法 |
JP2018065894A (ja) * | 2016-10-17 | 2018-04-26 | 株式会社カネカ | 精製された不飽和基含有ポリエーテル重合体の製造方法、及び加水分解性ケイ素基含有ポリエーテル重合体の製造方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114031764A (zh) * | 2021-10-22 | 2022-02-11 | 南京清研新材料研究院有限公司 | 一种聚醚的纯化方法 |
EP4273185A1 (en) | 2022-05-04 | 2023-11-08 | PCC Rokita SA | Method for the manufacture of a polyether diol product |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3356738A (en) | 1963-12-11 | 1967-12-05 | Witco Chemical Corp | Purification of water-insoluble hydroxyl-containing polyethers |
EP0038983A2 (de) | 1980-04-25 | 1981-11-04 | Bayer Ag | Verfahren zur Aufarbeitung von Polyetherpolyolen |
JPH01294733A (ja) | 1988-05-20 | 1989-11-28 | Kanegafuchi Chem Ind Co Ltd | 粗製ポリエーテルから塩基性アルカリ金属化合物と無機酸との無機塩を除去する方法 |
EP0693513A2 (en) | 1994-07-18 | 1996-01-24 | Asahi Glass Company Ltd. | Process for purifying a polyether |
JPH08109253A (ja) | 1994-10-07 | 1996-04-30 | Asahi Glass Co Ltd | ポリエーテル類の精製方法 |
JP2002249580A (ja) | 2001-02-26 | 2002-09-06 | Kanegafuchi Chem Ind Co Ltd | 粗製ポリエーテルから金属化合物を除去する方法 |
-
2005
- 2005-07-08 EP EP05765550.8A patent/EP1767563B1/en not_active Not-in-force
- 2005-07-08 WO PCT/JP2005/012637 patent/WO2006006511A1/ja not_active Application Discontinuation
- 2005-07-08 US US11/631,028 patent/US8367876B2/en active Active
- 2005-07-08 JP JP2006528991A patent/JP5009620B2/ja active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3356738A (en) | 1963-12-11 | 1967-12-05 | Witco Chemical Corp | Purification of water-insoluble hydroxyl-containing polyethers |
EP0038983A2 (de) | 1980-04-25 | 1981-11-04 | Bayer Ag | Verfahren zur Aufarbeitung von Polyetherpolyolen |
JPS56167727A (en) * | 1980-04-25 | 1981-12-23 | Bayer Ag | Finishing of polyether polyol |
JPH01294733A (ja) | 1988-05-20 | 1989-11-28 | Kanegafuchi Chem Ind Co Ltd | 粗製ポリエーテルから塩基性アルカリ金属化合物と無機酸との無機塩を除去する方法 |
EP0693513A2 (en) | 1994-07-18 | 1996-01-24 | Asahi Glass Company Ltd. | Process for purifying a polyether |
JPH08231707A (ja) | 1994-07-18 | 1996-09-10 | Asahi Glass Co Ltd | ポリエーテルの精製方法 |
JPH08109253A (ja) | 1994-10-07 | 1996-04-30 | Asahi Glass Co Ltd | ポリエーテル類の精製方法 |
JP2002249580A (ja) | 2001-02-26 | 2002-09-06 | Kanegafuchi Chem Ind Co Ltd | 粗製ポリエーテルから金属化合物を除去する方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1767563A4 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008050417A (ja) * | 2006-08-22 | 2008-03-06 | Kaneka Corp | ポリエーテルの製造方法 |
JP2010254981A (ja) * | 2009-03-31 | 2010-11-11 | Nof Corp | 高分子量ポリエチレングリコール化合物の精製方法 |
JP2014132077A (ja) * | 2009-03-31 | 2014-07-17 | Nof Corp | 高分子量ポリエチレングリコール化合物の精製方法 |
WO2014157117A1 (ja) * | 2013-03-27 | 2014-10-02 | 日油株式会社 | アミノ基を一つ有するポリエチレングリコールの精製方法 |
US9458292B2 (en) | 2013-03-27 | 2016-10-04 | Nof Corporation | Method for purifying polyethylene glycol having one amino group |
CN105189606B (zh) * | 2013-03-27 | 2017-06-09 | 日油株式会社 | 具有一个氨基的聚乙二醇的纯化方法 |
JP2015189915A (ja) * | 2014-03-28 | 2015-11-02 | 三菱化学株式会社 | ポリエーテルポリオールの製造方法 |
JP2018065894A (ja) * | 2016-10-17 | 2018-04-26 | 株式会社カネカ | 精製された不飽和基含有ポリエーテル重合体の製造方法、及び加水分解性ケイ素基含有ポリエーテル重合体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
JP5009620B2 (ja) | 2012-08-22 |
US20080033128A1 (en) | 2008-02-07 |
EP1767563B1 (en) | 2014-09-03 |
US8367876B2 (en) | 2013-02-05 |
JPWO2006006511A1 (ja) | 2008-04-24 |
EP1767563A1 (en) | 2007-03-28 |
EP1767563A4 (en) | 2007-09-19 |
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