WO2006075373A1 - β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法 - Google Patents

β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法 Download PDF

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Publication number
WO2006075373A1
WO2006075373A1 PCT/JP2005/000290 JP2005000290W WO2006075373A1 WO 2006075373 A1 WO2006075373 A1 WO 2006075373A1 JP 2005000290 W JP2005000290 W JP 2005000290W WO 2006075373 A1 WO2006075373 A1 WO 2006075373A1
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WO
WIPO (PCT)
Prior art keywords
alkoxypropionamide
solvent
carbon atoms
general formula
alkoxypropionamides
Prior art date
Application number
PCT/JP2005/000290
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English (en)
French (fr)
Japanese (ja)
Inventor
Shigeru Matsuo
Original Assignee
Idemitsu Kosan 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.)
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Publication date
Application filed by Idemitsu Kosan Co., Ltd. filed Critical Idemitsu Kosan Co., Ltd.
Priority to JP2006552798A priority Critical patent/JPWO2006075373A1/ja
Priority to PCT/JP2005/000290 priority patent/WO2006075373A1/ja
Priority to CN2005800465154A priority patent/CN101098851B/zh
Priority to KR1020077015950A priority patent/KR101114711B1/ko
Publication of WO2006075373A1 publication Critical patent/WO2006075373A1/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels

Definitions

  • the present invention relates to ⁇ -alkoxypropionamides, solvents, detergents and liquid pharmaceutical compositions, and a method for producing j8-alkoxypropionamides. More specifically, the ⁇ -alkoxypropionamide is obtained by reacting a solvent, a cleaning agent and a liquid drug composition containing a novel ⁇ -alkoxypropionamide, and an acrylamide with an aliphatic monohydric alcohol under mild conditions.
  • the present invention relates to a method for efficiently producing products. Background art
  • an amide organic solvent has an excellent dissolving power and a property of being easily dissolved in water, so that it can be rinsed with water and has desirable performance as a solvent or a cleaning agent.
  • amide solvents tend to replace conventional halogen solvents because halogen solvents can cause environmental pollution such as destroying the ozone layer and are highly toxic.
  • amide solvents examples include formamide, ⁇ ⁇ monomethylformamide, ⁇ , ⁇ ⁇ ⁇ ⁇ -dimethylformamide, ⁇ ⁇ monoethylformamide, ⁇ , ⁇ -jetylformamide, acetamide, ⁇ , ⁇ -dimethylacetamide, ⁇ methyl Since this amide solvent, which is known as pyrrolidinone, is excellent in solubility, it can dissolve most solvents and compounds, and can be suitably used as a cleaning agent. However, the application of amide solvents is greatly limited because they are not compatible with paraffins.
  • an amide having an alkoxy group is an alkoxy ⁇ , ⁇ as an intermediate in the production method of ⁇ , ⁇ -dialkylamides of ⁇ , ⁇ -year-old refining unsaturated monocarboxylic acids used as polymerizable monomers. —Dialkylpropionamide is formed.
  • This intermediate is amidated by reacting 13 alkoxypropionic acid alkyl ester with dialkylamine.
  • the reaction requires a long time of 24 to 40 hours in a sealed pressurized cylinder. Is a disadvantageous method (see Patent Document 1).
  • Patent Document 1 JP-A-49 66623 (pages 11 and 12)
  • the object of the present invention is to have a solvent and a cleaning agent having excellent dissolving power, which dissolves in paraffin or the like while maintaining the dissolving power of an amide solvent, or various agricultural products. It is to provide a liquid pharmaceutical composition that dissolves industrial chemicals well and maintains safety and long-term effects, and a method for industrially producing the solvent and the cleaning agent.
  • ⁇ -alkoxypropionamides obtained by reacting acrylamides with aliphatic monohydric alcohols have the ability to dissolve amide solvents. It is highly useful as a solvent and cleaning agent because it dissolves in paraffin and the like while being retained, and since certain j8-alkoxypropionamides do not dissolve in water, they can be used in agricultural chemicals for safety and long-term effects And that j8-alkoxypropionamides can be efficiently produced under mild conditions by reacting acrylamides with aliphatic monohydric alcohols in the presence of a basic catalyst. The present invention has been reached.
  • the present invention provides:
  • R 1 is an alkyl group having 3 to 18 carbon atoms
  • R 2 and R 3 may each independently have a hydrogen atom or an ether bond having a carbon number of 16 to 16, or a hydrocarbon group. And may be the same or different from each other, and may be further bonded to each other to form a ring structure.
  • R 4 is an alkyl group having 8 to 18 carbon atoms
  • R 2 and R 3 may each independently have a hydrogen atom or an ether bond having a carbon number of 16 to 16, or a hydrocarbon group. And may be the same or different from each other, and may be further bonded to each other to form a ring structure.
  • R 5 is an alkyl group having 5 to 18 carbon atoms, and R 2 and R 3 are the same as described above.
  • R 1 may be an alkyl group having 3 to 18 carbon atoms
  • R 2 and R 3 may each have a hydrogen atom or an ether bond having 1 to 16 carbon atoms.
  • Good monovalent hydrocarbon group examples include various butyl groups, various pentyl groups, various hexyl groups, various octyl groups, and the like, and those having 5 to 10 carbon atoms, preferably those having 4 to 12 carbon atoms. Is particularly preferred.
  • the R 2 and R 3 hydrocarbon groups may be either linear or branched, but are preferably saturated hydrocarbon groups.
  • R 2 and R 3 are They may be the same or different, and may be bonded together to form a ring structure.
  • This ring structure may be a heterocyclic structure having nitrogen as a heteroatom, or a heterocyclic structure having nitrogen and oxygen atoms as heteroatoms.
  • the group having a heterocyclic structure include a 1 pyrrolidinyl group, a piperidino group, and a morpholino group.
  • the / 3 alkoxypropionamides of the present invention have almost the same dissolving power as various amide solvents for various compounds, and also dissolve in paraffins. Can be widely used.
  • R 1 in the general formula (I) is an alkyl group having 8 to 18 carbon atoms, it is insoluble in water, so the j8-alkoxypropionamides of the present invention are agricultural chemicals such as insecticides and fungicides. Long-term effects can be maintained by dissolving
  • 8-alkoxypropionamides represented by the following general formula (II) are extremely advantageous as liquid pharmaceutical compositions in which the above agricultural chemicals are dissolved, that is, as liquid application agents such as emulsions and oils. Can be used.
  • R 4 is an alkyl group having 8 to 18 carbon atoms, and includes various octyl groups such as an n-ethyl octyl group and 2-ethyl hexyl group, various nonyl groups, and various decyl groups. And various lauryl groups, various stearyl groups, and various oleyl groups.
  • R 2 and R 3 are the same as in the general formula (I).
  • R 2 and R 3 are the same as in the general formula (I).
  • Specific examples of such acrylamides include acrylamide, N-methylacrylamide, N, N-dimethylacrylamide, N-ethylacrylamide, N, N-jetylacrylamide, N-propylacrylamide, N, N-dipropyl.
  • Powers such as acrylamide, N-butyl acrylamide, N, N-dibutyl acrylamide, 1-attalyloyl pyrrolidine, 1- attaroyl biperidine, 4-1 allyloyl morpholine, among them acrylamide, N-methyl acrylamide, N , N-dimethylacrylamide, N-ethyl acrylamide, N, N-jetyl acrylamide, and 4-ataryloylmorpholine are preferred.
  • Another raw material in the production method of the present invention is an aliphatic monovalent alcohol having 5 to 18 carbon atoms
  • R 5 in the general formula (IV) is an alkyl group having 5 to 18 carbon atoms.
  • These aliphatic monohydric alcohols may be either linear or branched, specifically n-pentano mononole, hexanol, octanol, 2-ethino hexanol, decenoreanolo gnole, laur Such as ril alcohol,
  • a mixture may be produced in the reaction.
  • two or more of the acrylamides as raw materials may be used in combination, or two or more of the aliphatic monohydric alcohols may be used in combination, or both.
  • the proportion of acrylamides and aliphatic monohydric alcohols used is preferably that of aliphatic monohydric alcohols in stoichiometric amounts or in excess, but if used in excessive amounts, Since it is disadvantageous in terms of economy, generally, an aliphatic monohydric alcohol is used in an amount of 1.0 to 3 mol, preferably 1.0 to 2 mol, per 1 mol of acrylamides.
  • the reaction between the acrylamide and the aliphatic monohydric alcohol is carried out in the presence of a basic catalyst.
  • a basic substance can be used as a catalyst, but potassium tert butoxide, sodium tertbutoxide, potassium hydroxide and potassium carbonate are preferred in view of reaction conditions and by-products. Sodium methoxide and potassium methoxide are not preferred because by-products are formed. Further, sodium hydroxide and sodium carbonate are not preferable because the reaction time becomes long.
  • the basic catalyst may be used alone or in combination of two or more.
  • the amount used is appropriately selected according to the type of raw material that is not particularly limited. Generally, it is selected in the range of 0.5-10 mol%, preferably 1-3 mol%, per mol of acrylamide. Is done.
  • the reaction temperature is preferably 20-80 ° C, and more preferably 30-50 ° C. If the temperature is too high, the yield may decrease, and if the temperature is too low, the reaction rate decreases, which is not practical. In addition, the reaction proceeds at normal pressure or under pressure, but generally normal pressure is economically advantageous.
  • the reaction time depends on the raw materials used, the type of catalyst, the reaction temperature, etc., and cannot be determined in general, but it is usually 30 minutes to 10 hours, preferably 115 hours. As the solvent, acetone, ether and amide solvents can be used, but it is preferable not to use them in consideration of economy.
  • the produced ⁇ -alkoxypropionamide is preferably neutralized with a base used as a catalyst with phosphoric acid, acetic acid, sulfuric acid or the like after completion of the reaction, and then the salt produced by filtration or the like is removed. Further, it can be obtained by separating the unreacted material with a thin film evaporator or the like, if necessary.
  • j8-alkoxypropionamides having excellent performance as an amide solvent can be reacted in a short time under mild conditions, and post-treatment and purification after the reaction are easy. It can be manufactured by the method.
  • each test tube contains 5 mL of the compound obtained in each example ( ⁇ -alkoxypropionamide) and 5 mL of the amide solvent used in the comparative examples, and 5 g of n-hexane, liquid paraffin, glycerin and water as solubility confirmation substances. And shaken at room temperature or at 80 ° C for 5 minutes. When heated at 80 ° C., the solution state was observed after cooling to room temperature. A uniform state was considered compatible, and a turbid or phase-separated one was made incompatible.
  • N, N-dimethylacrylamide (19.828 g) and 1-hexanol (20.434 g) were placed in a 300 mL separable flask equipped with a stirrer, a thermocouple, and a nitrogen gas inlet tube, and stirred while introducing nitrogen gas.
  • 0.338 g of sodium t-butoxide was added, and the reaction was performed at 35 ° C for 4 hours.
  • 150 mg of phosphoric acid was added to make the solution uniform, and then left for 3 hours.
  • the solution was filtered to remove precipitates, and unreacted substances were removed with an evaporator.
  • the yield was 37.4 g (93% yield).
  • N, N-dimethylacrylamide 19.828 g and 1-butanol 14.824 g were added and stirred while introducing nitrogen gas.
  • 0.338 g of sodium t-butoxide was added, and the reaction was carried out at 35 ° C. for 4 hours.
  • 150 mg of phosphoric acid was added to make the solution uniform, and then left for 3 hours.
  • the solution was filtered to remove precipitates, and unreacted substances were removed with an evaporator.
  • the yield was 30.5 g (88% yield).
  • N, N-dimethylacrylamide (19.828 g) and 2-ethyl hexanol (26.046 g) were placed and stirred while introducing nitrogen gas.
  • 0.338 g of sodium t-butoxide was added, and the reaction was performed at 35 ° C. for 4 hours.
  • 150 mg of phosphoric acid was added to make the solution uniform, and then left for 3 hours.
  • the solution was filtered to remove precipitates, and unreacted substances were removed with an evaporator.
  • the yield was 43.6 g (95% yield).
  • Example 3 was carried out in the same manner as Example 3 except that 26.046 g of n-year-old octanol was used instead of 2-ethylhexanol. The yield was 42.7 g (93% yield). The results of the solubility test are shown in Table 1.
  • the j8-alkoxypropionamides of the present invention are widely used as excellent cleaning agents and solvents because they retain the solubility of conventional amide solvents, have a high boiling point, and also have a solubility in paraffin and the like. it can.
  • 8-alkoxypropionamides represented by the general formula (II) retain the solubility of conventional amide solvents in pesticides such as insecticides and fungicides, but do not dissolve in water. It is possible to maintain the effect as an agrochemical with high safety because there is no pollution to drainage. Accordingly, ⁇ -alkoxypropionamides represented by the general formula ( ⁇ ) are extremely useful as liquid pharmaceutical compositions (liquid application agents) such as emulsions and oils in agricultural chemicals.
  • the method for producing j8-alkoxypropionamides of the present invention provides j8-alkoxypropionamides in a short reaction under mild reaction conditions, and is easy and efficient after-reaction and purification after the reaction. Can be manufactured.

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  • Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/JP2005/000290 2005-01-13 2005-01-13 β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法 WO2006075373A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2006552798A JPWO2006075373A1 (ja) 2005-01-13 2005-01-13 β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法
PCT/JP2005/000290 WO2006075373A1 (ja) 2005-01-13 2005-01-13 β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法
CN2005800465154A CN101098851B (zh) 2005-01-13 2005-01-13 β-烷氧基丙酰胺类、溶剂、洗涤剂和液态药物组合物以及β-烷氧基丙酰胺类的制备方法
KR1020077015950A KR101114711B1 (ko) 2005-01-13 2005-01-13 β-알콕시프로피온아마이드류, 용제, 세정제 및 액상 약제조성물, 및 β-알콕시프로피온아마이드류의 제조방법

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JP2008174740A (ja) * 2006-12-19 2008-07-31 Lion Corp 液体洗浄剤組成物用洗浄溶剤
JP2010168433A (ja) * 2009-01-21 2010-08-05 Toyo Ink Mfg Co Ltd β−アルコキシプロピオンアミド類を使用した水性インキ組成物
JP2010180332A (ja) * 2009-02-06 2010-08-19 Toyo Ink Mfg Co Ltd 非水性インキ組成物
WO2010126086A1 (ja) * 2009-05-01 2010-11-04 出光興産株式会社 αβ不飽和カルボン酸-Ｎ,Ｎ二置換アミド及び３-アルコキシカルボン酸-Ｎ,Ｎ二置換アミドの製造方法
WO2011012562A2 (de) 2009-07-31 2011-02-03 Basf Se Flüssige zusammensetzung enthaltend pestizid, nichtionisches tensid und propionamid
JP2011068838A (ja) * 2009-09-28 2011-04-07 Idemitsu Kosan Co Ltd 水性インク組成物
US20110263898A1 (en) * 2008-04-30 2011-10-27 Rhodia Operations Ether-amide compounds and preparation and uses thereof
JP2011252071A (ja) * 2010-06-01 2011-12-15 Idemitsu Kosan Co Ltd 洗浄剤組成物及びそれを用いたエアゾール組成物
JP2012207118A (ja) * 2011-03-29 2012-10-25 Seiko Epson Corp インクジェット用非水系インク組成物およびインクジェット記録方法
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JP2020002037A (ja) * 2018-06-27 2020-01-09 フマキラー株式会社 害虫防除組成物、エアゾール剤及びエアゾール製品

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FR2961205B1 (fr) * 2010-06-09 2012-06-29 Rhodia Operations Procede de preparation de composes esteramides
CN104478749A (zh) * 2014-11-10 2015-04-01 平湖优康药物研发有限公司 一种新型液晶材料3-丁氧基-n,n-二甲基丙酰胺的合成工艺

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2704280A (en) * 1951-05-29 1955-03-15 Colgate Palmolive Co Long-chain aliphatic ether-amides in detergent compositions
GB1218168A (en) * 1968-05-10 1971-01-06 Basf Ag Finishing agent for textile material
US3712926A (en) * 1969-04-25 1973-01-23 Basf Ag Production of n-polyalkoxymethylamides
JPS5094058A (zh) * 1973-09-25 1975-07-26
JPS63303960A (ja) * 1987-06-04 1988-12-12 Tokuyama Soda Co Ltd 医・農薬中間原料の製造方法
JPH01172367A (ja) * 1987-12-25 1989-07-07 Tokuyama Soda Co Ltd オキシアルキルカーバメート化合物の製造方法
US5599947A (en) * 1993-01-14 1997-02-04 G. D. Searle & Co. Fatty acid analogs and prodrugs
JP2005047885A (ja) * 2003-07-17 2005-02-24 Idemitsu Kosan Co Ltd β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2704280A (en) * 1951-05-29 1955-03-15 Colgate Palmolive Co Long-chain aliphatic ether-amides in detergent compositions
GB1218168A (en) * 1968-05-10 1971-01-06 Basf Ag Finishing agent for textile material
US3712926A (en) * 1969-04-25 1973-01-23 Basf Ag Production of n-polyalkoxymethylamides
JPS5094058A (zh) * 1973-09-25 1975-07-26
JPS63303960A (ja) * 1987-06-04 1988-12-12 Tokuyama Soda Co Ltd 医・農薬中間原料の製造方法
JPH01172367A (ja) * 1987-12-25 1989-07-07 Tokuyama Soda Co Ltd オキシアルキルカーバメート化合物の製造方法
US5599947A (en) * 1993-01-14 1997-02-04 G. D. Searle & Co. Fatty acid analogs and prodrugs
JP2005047885A (ja) * 2003-07-17 2005-02-24 Idemitsu Kosan Co Ltd β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008174740A (ja) * 2006-12-19 2008-07-31 Lion Corp 液体洗浄剤組成物用洗浄溶剤
US8969621B2 (en) * 2008-04-30 2015-03-03 Rhodia Operations Ether-amide compounds and preparation and uses thereof
US20110263898A1 (en) * 2008-04-30 2011-10-27 Rhodia Operations Ether-amide compounds and preparation and uses thereof
US9371273B2 (en) 2008-04-30 2016-06-21 Rhodia Operations Ether-amide compounds and preparation and uses thereof
JP2010168433A (ja) * 2009-01-21 2010-08-05 Toyo Ink Mfg Co Ltd β−アルコキシプロピオンアミド類を使用した水性インキ組成物
JP2010180332A (ja) * 2009-02-06 2010-08-19 Toyo Ink Mfg Co Ltd 非水性インキ組成物
JP5690720B2 (ja) * 2009-05-01 2015-03-25 出光興産株式会社 αβ不飽和カルボン酸−Ｎ，Ｎ二置換アミド及び３−アルコキシカルボン酸−Ｎ，Ｎ二置換アミドの製造方法
WO2010126086A1 (ja) * 2009-05-01 2010-11-04 出光興産株式会社 αβ不飽和カルボン酸-Ｎ,Ｎ二置換アミド及び３-アルコキシカルボン酸-Ｎ,Ｎ二置換アミドの製造方法
US20140235894A1 (en) * 2009-05-01 2014-08-21 Idemitsu Kosan Co., Ltd. Method for producing alpha,beta-unsaturated carboxylic acid-n,n-disubstituted amide and method for producing 3-alkoxycarboxylic acid-n,n-disubstituted amide
US8748659B2 (en) 2009-05-01 2014-06-10 Idemitsu Kosan Co., Ltd. Method for producing alpha,beta-unsaturated carboxylic acid-N,N-disubstituted amide and method for producing 3-alkoxycarboxylic acid-N,N-disubstituted amide
JP2014169315A (ja) * 2009-05-01 2014-09-18 Idemitsu Kosan Co Ltd αβ不飽和カルボン酸−Ｎ，Ｎ二置換アミド及び３−アルコキシカルボン酸−Ｎ，Ｎ二置換アミドの製造方法
WO2011012562A3 (de) * 2009-07-31 2011-10-20 Basf Se Flüssige zusammensetzung enthaltend pestizid, nichtionisches tensid und propionamid
WO2011012562A2 (de) 2009-07-31 2011-02-03 Basf Se Flüssige zusammensetzung enthaltend pestizid, nichtionisches tensid und propionamid
JP2011068838A (ja) * 2009-09-28 2011-04-07 Idemitsu Kosan Co Ltd 水性インク組成物
US9056992B2 (en) 2010-05-26 2015-06-16 Seiko Epson Corporation Nonaqueous ink composition for ink jet recording and ink jet recording method
US8936358B2 (en) 2010-05-26 2015-01-20 Seiko Epson Corporation Ink composition for ink jet textile printing and ink jet textile printing process
JP2011252071A (ja) * 2010-06-01 2011-12-15 Idemitsu Kosan Co Ltd 洗浄剤組成物及びそれを用いたエアゾール組成物
US8840233B2 (en) 2010-09-03 2014-09-23 Seiko Epson Corporation Ink jet recording-targeted non-aqueous ink composition, ink set, and ink jet recording method
JP2012207118A (ja) * 2011-03-29 2012-10-25 Seiko Epson Corp インクジェット用非水系インク組成物およびインクジェット記録方法
JP6070546B2 (ja) * 2011-04-25 2017-02-01 旭硝子株式会社 撥水撥油剤組成物、その製造方法および物品
JPWO2012147700A1 (ja) * 2011-04-25 2014-07-28 旭硝子株式会社 撥水撥油剤組成物、その製造方法および物品
JPWO2012147625A1 (ja) * 2011-04-27 2014-07-28 旭硝子株式会社 撥水撥油剤組成物、その製造方法および物品
JPWO2012147573A1 (ja) * 2011-04-27 2014-07-28 旭硝子株式会社 撥水撥油剤組成物、その製造方法および物品
WO2012147573A1 (ja) * 2011-04-27 2012-11-01 旭硝子株式会社 撥水撥油剤組成物、その製造方法および物品
US9040625B2 (en) 2011-04-27 2015-05-26 Asahi Glass Company, Limited Water/oil repellent composition, method for its production and article
WO2012147625A1 (ja) * 2011-04-27 2012-11-01 旭硝子株式会社 撥水撥油剤組成物、その製造方法および物品
JP6070545B2 (ja) * 2011-04-27 2017-02-01 旭硝子株式会社 撥水撥油剤組成物、その製造方法および物品
JP2014101517A (ja) * 2013-12-27 2014-06-05 Dainippon Toryo Co Ltd 水性インク組成物
WO2019230621A1 (ja) * 2018-05-28 2019-12-05 日産化学株式会社 農薬乳化性組成物
JPWO2019230621A1 (ja) * 2018-05-28 2021-06-24 日産化学株式会社 農薬乳化性組成物
JP7287392B2 (ja) 2018-05-28 2023-06-06 日産化学株式会社 農薬乳化性組成物
JP2020002037A (ja) * 2018-06-27 2020-01-09 フマキラー株式会社 害虫防除組成物、エアゾール剤及びエアゾール製品
JP7133838B2 (ja) 2018-06-27 2022-09-09 フマキラー株式会社 害虫防除組成物、エアゾール剤及びエアゾール製品

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