WO2000053576A1 - Agents de gelification ou de coagulation pour supports organiques liquides - Google Patents

Agents de gelification ou de coagulation pour supports organiques liquides Download PDF

Info

Publication number
WO2000053576A1
WO2000053576A1 PCT/JP2000/001234 JP0001234W WO0053576A1 WO 2000053576 A1 WO2000053576 A1 WO 2000053576A1 JP 0001234 W JP0001234 W JP 0001234W WO 0053576 A1 WO0053576 A1 WO 0053576A1
Authority
WO
WIPO (PCT)
Prior art keywords
gelling
alkyl
liquid organic
linear
alkenyl
Prior art date
Application number
PCT/JP2000/001234
Other languages
English (en)
Japanese (ja)
Inventor
Kenji Hanabusa
Hiroko Nakayama
Mutsumi Kimura
Hirofusa Shirai
Original Assignee
Ajinomoto Co., Inc.
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 Ajinomoto Co., Inc. filed Critical Ajinomoto Co., Inc.
Publication of WO2000053576A1 publication Critical patent/WO2000053576A1/fr

Links

Classifications

    • 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
    • C09K3/00—Materials not provided for elsewhere
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/16—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by carboxyl groups

Definitions

  • the present invention is an organic medium New alpha useful for gelling or solidifying exhibiting the liquid state at normal temperature - characterized in that it contains one with Ashiruamino acid ester compound and less of these - alkyl or Aruke carbamoylmethyl over New omega And a gelling or solidifying agent.
  • Examples of such a substance having a function of controlling the fluidity and viscosity of a liquid substance include alkali metal salts of long-chain fatty acids (JP-A-55-75493) and metal soaps (JP-B-59-595). 216), 12-hydroxystearic acid (Japanese Patent Publication No. 60-449968), a condensate of a polyhydric alcohol and benzaldehyde (Japanese Patent Application Laid-Open No. 59-77859), and p-acylamino Acid amide (Japanese Patent Publication No. 54-333798) was known.
  • metal salts of long-chain fatty acids and metallic soaps gel liquid organic media.
  • a large amount of addition is required for solidification, and there are restrictions on use conditions such as pH.
  • 12-hydroxystearic acid has few types of organic media that can be gelled and has a low gelling ability, the resulting gel is weak and brittle and easily breaks, and lacks gel stability near room temperature.
  • polyvalent alcohol and benzaldehyde condensates such as dibenzylidene sorbitol, can gel many organic media, but have a high dissolution temperature, so they can be used in combination with low boiling substances or substances that are sensitive to heat. There are restrictions when doing so.
  • N-Acyl amino acid amides such as N-lauroyl L-glutamic acid and 7-di-n-butylamide, can gel or solidify many organic media with a small amount of addition. Although the obtained gel had high strength, it did not have sufficient gelling ability with respect to lower alcohols such as methanol and did not necessarily have satisfactory gelling performance.
  • gelling or solidifying agents for liquid organic media have been actively developed in recent years.
  • examples thereof include cyclohexanthyl carboxamide (JP-A-10-273477), bis (acylamino) cyclohexane derivative (JP-A-10-237034), and oligobutidealkylamide derivative (JP-A-10-24539).
  • 6, JP-A-10-226614 dialkyl perylene derivatives obtained by reacting diaminocyclohexane with alkyl isocyanate (JP-A-8-231 942), cyclic peptides ( JP-A-7-247474, JP-A-7-247473) and the like.
  • the present invention is capable of gelling or solidifying a wide variety of liquid organic media with a small amount of addition, and the gelled material has a long-term stability near room temperature.
  • An object of the present invention is to provide a gelling or solidifying agent which is excellent and can be produced by a simpler method.
  • New alpha represented by the following general formula (1) - alkyl or alkenyl carbamoylmethyl over New omega - ⁇ shea Ruamino ester compound, various They have found that they have excellent gelling ability with various liquid organic media and can be synthesized by a simple method. Based on such findings, they have completed the present invention.
  • the present invention relates to a Na-alkyl or alkenylcarbamoyl-— ⁇ -acyl amino acid ester compound represented by the following general formula (1) itself, and a gelling or solidifying agent containing the compound as an active ingredient.
  • R 1 represents a linear or branched alkyl or alkenyl group having from 21 to 21 carbon atoms
  • R 2 represents a linear or branched and / or cyclic group having from 1 to 22 carbon atoms.
  • R 3 is an alkyl or alkenyl group having a straight or branched chain having 8 to 22 carbon atoms and / or having a cyclic structure
  • n is an integer of 2 to 4. Show.
  • Ester compound of the present invention New omega - the Ashiruamino acid as a starting material, carboxy It is obtained by esterification of the W group with an alcohol and alkylation or carbamoylation by alkylation of the amino group with an alkylisocyanate or alkenylisocyanate.
  • the ester compound of the present invention is a novel compound.
  • the Ashiruamino acid, ⁇ £ - - ⁇ ⁇ Ashirurijin, N fi - Ashiruoru two Chin, N Aashiru Ichihi, include Ajiamino butyric, in this, New epsilon - Ashirurijin is most preferred.
  • an acyl group of the amino acid an acyl group derived from a linear or branched saturated or unsaturated fatty acid having 8 to 22 carbon atoms is preferable.
  • octanoic acid decanoic acid
  • Lauric acid palmitic acid
  • stearic acid and oleic acid.
  • the number of carbon atoms of the acyl group is less than 8, the gelling ability is poor, and when it is more than 22, the solubility in a liquid organic medium is poor, and a treatment at a high temperature is required for dissolution, which is not appropriate.
  • New omega - Ashiruamino acid for example a basic amino acid and a long chain fatty acid can be easily synthesized by heating dehydration.
  • Industrially available amino acids include "Amihob LL" (N £ -lauroyl-L-lysine) manufactured by Ajinomoto Co., Inc.
  • ⁇ ⁇ -Acyl amino acid may be either optically active or racemic. These may be used alone or in combination of two or more.
  • the alcohol used for esterification of ⁇ -acyl amino acid is an alcohol having a linear or branched saturated or unsaturated and / or cyclic having 1 to 22 carbon atoms, such as methanol, ethanol, ⁇ —Propanol, isopropanol, ⁇ -butanol, 2-butanol, ⁇ -pentanol, ⁇ -hexanol, cyclohexanol, ⁇ -hexanol, ⁇ -octanol, 2-ethylhexa Knoll, ⁇ -nonanol, ⁇ -decanol, lauryl alcohol, myristylua Examples thereof include alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, stearyl alcohol, isostearyl alcohol, behenyl alcohol, and 2-octyldodecanol. If it is not esterified, the compound will crystallize and have no gelling ability.If it has more than
  • Alkyl isocyanate used for alkylation of a primary amino group of ⁇ -acyl amino acid, which has a linear or branched and / or cyclic structure having 8 to 18 carbon atoms.
  • octyl isocyanate nonyl isocyanate, decyl isocyanate, pendecyl isocyanate, dodecyl isocyanate, tridecyl isocyanate, tetradecyl isocyanate, pentadecyl isocyanate, hexadecyl isocyanate
  • Examples thereof include cyanate, heptadecyl isocyanate, octadecyl isocyanate, 2-ethylhexyl isocyanate, and 21-hexyldecyl isocyanate.
  • alkylisocyanate has less than 8 carbon atoms, the organic solvent that can be gelled is limited, and if it has more than 18 carbon atoms, the solubility in the liquid organic medium is poor, and it will dissolve. This requires high temperature treatment, which is not appropriate.
  • Examples of industrially available alkyl isocyanates include “Millionaires” (octadecyl isocyanate) manufactured by Hodogaya Chemical Industry Co., Ltd. These may be used alone or as a mixture of two or more.
  • ester compound of the present invention is a novel compound, which is obtained by using the above-mentioned “amino acid”, alcohol and alkyl isocyanate or alkenyl isocyanate as raw materials, and by a generally known method.
  • Ru can be synthesized, for example, first New omega -.
  • the reaction product thus obtained may contain unreacted raw materials in addition to the target ester compound, but it may be purified by a known method such as extraction, recrystallization, or chromatography. it can. This purification may be performed to such an extent that the object (effect) of the present invention is not adversely affected by the use of the gelling or solidifying agent of the present invention.
  • the mixture may be used as it is, as long as the gelling ability is not affected.
  • the ester compound of the present invention can be referred to as the gelling or solidifying agent of the present invention. It can be prepared by blending additives such as agents.
  • the ester compound of the present invention is excellent in the action of gelling or solidifying a wide variety of liquid organic media with a small amount of addition.
  • the liquid organic medium include mineral oils such as gazolin, kerosene, light oil, and heavy oil; animal oils such as whale oil and dicin oil; soybean oil, olive oil, castor oil, linseed oil, corn oil, Vegetable oils such as castor oil, rapeseed oil, and cottonseed oil; hydrocarbons such as petroleum benzene, liquid paraffin, benzene, toluene, hexane, and cyclohexane; ethyl acetate, butyl acetate, amyl acetate, getyl sebacate, and sebacic acid Esters such as dioctyl, getyl phthalate, dioctyl phthalate, and polyoxyalkylene glycol fatty acid esters; ethers such as diglyme and polyalkylene glycol ether;
  • the gelling or solidifying agent containing the ester compound of the present invention as an active ingredient.
  • it can be performed as follows. That is, the gelling or solidifying agent of the present invention (including, as described above, the one comprising only the ester compound of the present invention) is added to the above-mentioned liquid organic medium, and 50
  • the liquid organic medium can be changed to a gelled or solidified substance by heating and stirring to a uniform state of about 120 ° C. and then standing at room temperature.
  • the amount of the ester compound used in the present invention depends on the type of the organic medium to be gelled or solidified, but it is 1 to 400 parts by weight, preferably 1 to 100 parts by weight, based on the liquid organic medium 1,000 parts by weight.
  • the amount is from 200 to 200 parts by weight, preferably from 1 to 100 parts by weight, and more preferably from 2 to 80 parts by weight. If the amount used is less than 1 part by weight, the gelling or solidification will not be sufficient, and if it is more than 400 parts by weight, when gelling or solidifying, a part of the gelling agent will crystallize and precipitate, resulting in a non-uniform state. Appearance is poor and stable gelation or solidification strength cannot be maintained, which is not appropriate.
  • the hardness of the gelled product or the solidified product can be freely adjusted by the amount of the ester compound of the present invention.
  • ester compound of the present invention (therefore, the gelling or solidifying agent of the present invention) can be synthesized from industrially manufactured easily available raw materials by a simple method.
  • the compound of the present invention and the comparative control compound were each added to a test tube with a lid in an amount of 5 mg each, and 2 ml of each organic medium was added to each, and the lid was capped and completely dissolved completely. Until heated. After dissolution, the solution was allowed to stand in a thermostat at 25 ° C for 2 hours and visually observed. Add compound if gelation is incomplete, add organic medium if gelled completely, and add the minimum amount of compound required to gel each organic medium per ml (Mg). However, the maximum amount of the compound to be added was up to 20 mg per 2 m1 of the organic medium, and in this state, a liquid or a substance that crystallized and precipitated was evaluated as “no gelation”. Note that “1” in the table indicates that measurement has not been performed. Table 1
  • Example 1 Example 2 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Liquid Organic Medium Comparative Example 1 Comparative Example 2 Comparative Example 2 1 2—Human 'roxy N-acyl amino acid compound Steering compound Ethanol compound 2 6 2 5 2 0 1 5 8 0 1 5 Cyclohexa Non 4 5 5 0 3 5 5 0 No gelling 25 5 70 No gelling No gelling No gelling No gelling No gelling
  • the ester compound of the present invention can gel various organic media with a small amount of addition as compared with a conventional gelling agent.
  • the obtained gel was stored at 30 ° C for 1 month and its state was observed, the gel was uniform without any change from the initial state, and no liquid portion was generated even after long-term storage. It was confirmed to be stable.
  • New alpha represented by the chemical formula (1) to gel or solidify at Ashiruamino ester compound small amount of a wide variety of liquid organic medium with - alkyl or alkenyl-carbamoyl over New omega It is possible to provide a gelling or solidifying agent which is excellent in long-term stability at around room temperature and can be synthesized by a simpler method.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

Cette invention concerne de nouveaux esters Nα-alkyl- ou alcénylcarbomoyl-Nφ acylaminoacides représentés par la formule générale (1) (dans laquelle R1 est un alkyle ou un alcényle en C¿7?-C21 linéaire ou ramifié ; R?2¿ est un alkyle ou un alcényle en C¿1?-C22 linéaire, ramifié ou cyclique ; R?3¿ est un alkyle ou un alcényle en C¿8?-C22 linéaire, ramifié ou cyclique et n est un entier compris entre 2 et 4). L'adjonction de ces esters, même en faible quantité, permet de gélifier ou de coaguler les supports organiques liquides les plus divers. Les gels ainsi obtenus possédent une excellente stabilité à long terme et à température normale et peuvent être synthétisés de façon simple et facile, ce qui en fait de remarquables agents de gélification et de coagulation.
PCT/JP2000/001234 1999-03-11 2000-03-02 Agents de gelification ou de coagulation pour supports organiques liquides WO2000053576A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/64328 1999-03-11
JP06432899A JP4099891B2 (ja) 1999-03-11 1999-03-11 液状有機媒体のゲル化又は固化剤

Publications (1)

Publication Number Publication Date
WO2000053576A1 true WO2000053576A1 (fr) 2000-09-14

Family

ID=13255075

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2000/001234 WO2000053576A1 (fr) 1999-03-11 2000-03-02 Agents de gelification ou de coagulation pour supports organiques liquides

Country Status (2)

Country Link
JP (1) JP4099891B2 (fr)
WO (1) WO2000053576A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003014249A1 (fr) * 2001-08-07 2003-02-20 Japan Science And Technology Corporation Agent gelifiant derive du sucre et destine a la formation d'un hydrogel
WO2004096754A1 (fr) * 2003-04-28 2004-11-11 Ajinomoto Co., Inc. Dérivé d'acide aminé à deux têtes
WO2007078013A1 (fr) * 2006-01-06 2007-07-12 Ajinomoto Co., Inc. Agent gelifiant
CN104114535A (zh) * 2012-02-09 2014-10-22 味之素株式会社 两性离子型碱性氨基酸衍生物
CN106536477A (zh) * 2014-07-30 2017-03-22 味之素株式会社 中链酰基碱性氨基酸衍生物

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004182696A (ja) * 2002-12-05 2004-07-02 Shiseido Co Ltd 外用剤組成物
JP2004262859A (ja) * 2003-03-03 2004-09-24 Shiseido Co Ltd 外用剤組成物
JP2004262857A (ja) * 2003-03-03 2004-09-24 Shiseido Co Ltd 外用剤組成物
JP2004269459A (ja) * 2003-03-11 2004-09-30 Nippon Unicar Co Ltd アミノ酸誘導体変性シリコーンを含有する油性化粧料
JP4543692B2 (ja) * 2003-04-28 2010-09-15 味の素株式会社 塩基性アミノ酸誘導体
JP4770179B2 (ja) * 2004-01-19 2011-09-14 三菱瓦斯化学株式会社 新規なトリフェニルメタン誘導体、それを含有する有機ゲル化剤、有機ゲルおよび有機ファイバー
JP4765256B2 (ja) * 2004-03-11 2011-09-07 コニカミノルタホールディングス株式会社 活性光線硬化型インクジェットインクとそれを用いたインクジェット記録方法
JP5347104B2 (ja) * 2007-03-09 2013-11-20 味の素株式会社 ゲル化剤
JP5376290B2 (ja) 2008-09-24 2013-12-25 国立大学法人静岡大学 尿素化合物、尿素化合物の自己集合体及び自己集合体を含有するオルガノゲル並びにオルガノゲルの製造方法
KR102073769B1 (ko) 2012-03-08 2020-02-05 고쿠리쓰다이가쿠호진 규슈다이가쿠 신규 당유도체 겔화제
JP6227623B2 (ja) 2013-02-13 2017-11-08 国立大学法人九州大学 ゲル化剤及びオルガノゲル

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5266885A (en) * 1975-12-01 1977-06-02 Ajinomoto Co Inc Gel composition containing water soluble organic medium
US4624962A (en) * 1981-09-03 1986-11-25 Hoechst Aktiengesellschaft Substituted derivatives of 2-azabicyclo-[3.3.0]octanes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5266885A (en) * 1975-12-01 1977-06-02 Ajinomoto Co Inc Gel composition containing water soluble organic medium
US4624962A (en) * 1981-09-03 1986-11-25 Hoechst Aktiengesellschaft Substituted derivatives of 2-azabicyclo-[3.3.0]octanes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KATO TAKSHI ET AL.: "Liquid-crystalline physical gels: electro-optic behavior and anisotropic molecular self-aggregation", POLYM. MATER. SCI. ENG.,, vol. 82, 2000, pages 334 - 335, XP000933494 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003014249A1 (fr) * 2001-08-07 2003-02-20 Japan Science And Technology Corporation Agent gelifiant derive du sucre et destine a la formation d'un hydrogel
WO2004096754A1 (fr) * 2003-04-28 2004-11-11 Ajinomoto Co., Inc. Dérivé d'acide aminé à deux têtes
US6921747B2 (en) 2003-04-28 2005-07-26 Ajinomoto Co., Inc. Basic amino acid derivatives
WO2007078013A1 (fr) * 2006-01-06 2007-07-12 Ajinomoto Co., Inc. Agent gelifiant
US7850955B2 (en) 2006-01-06 2010-12-14 Ajinomoto Co., Inc. Gelling agent
CN101365415B (zh) * 2006-01-06 2012-09-12 味之素株式会社 凝胶剂
JP5092753B2 (ja) * 2006-01-06 2012-12-05 味の素株式会社 ゲル化剤
CN104114535A (zh) * 2012-02-09 2014-10-22 味之素株式会社 两性离子型碱性氨基酸衍生物
US9750676B2 (en) 2012-02-09 2017-09-05 Ajinomoto Co., Inc. Basic amino acid derivative that demonstrates a gelling ability in a water system
CN106536477A (zh) * 2014-07-30 2017-03-22 味之素株式会社 中链酰基碱性氨基酸衍生物

Also Published As

Publication number Publication date
JP2000256303A (ja) 2000-09-19
JP4099891B2 (ja) 2008-06-11

Similar Documents

Publication Publication Date Title
WO2000053576A1 (fr) Agents de gelification ou de coagulation pour supports organiques liquides
DE2947140C2 (fr)
JP2006225406A (ja) ２−オキサゾリジノン誘導体のワンポット合成
US2851494A (en) New alpha-amino-beta-hydroxycarboxylic acid amides and a process of preparing them
JP2005047885A (ja) 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
JP4543692B2 (ja) 塩基性アミノ酸誘導体
EP1473027B1 (fr) Dérivés des acides aminés basiques et leur utilisation comme agents gélifiants
JP2002080599A (ja) アミノ酸誘導体セグメント含有シロキサンポリマー及びそれを含有する有機媒体のゲル化剤
TW202200564A (zh) ４－（２－（吡咯啶－１－基）－４－（三氟甲基）苄基）哌－１－甲酸１，１，１，３，３，３－六氟丙－２－基酯之製造
DE69914560T2 (de) Verfahren zur acylierung von aminoalcoholen
JP3254725B2 (ja) 新しい有機性ゲル化剤
EP2188246B1 (fr) Organogelifiants d'oxylamide amphiphiles conçus pour gelifier des solvants organiques, de l'eau et des combustibles hydrocarbures commerciaux
JP5585868B2 (ja) 尿素化合物、尿素化合物の自己集合体ならびに自己集合体を含有するオルガノゲル及びその製造方法
JPS6032775A (ja) 含フッ素ベンゾジアゼピン類
JP2912375B2 (ja) アジドーカルボン酸エステルの製造方法
RU2167852C1 (ru) Способ получения этилового эфира 4-карбоксифениламида малоновой кислоты
JP3920815B2 (ja) リジン誘導体及びゲル化剤
DE69722565T2 (de) Verfahren zur Herstellung von 4-Hydroxy-2-Pyrrolidinon und Verfahren zu deren Reinigung
DE1902582A1 (de) Verfahren zur Herstellung von Phenylalaninderivaten
Foye et al. Amino acid derivatives of aminosalicylic acids
JPH04124157A (ja) 光学活性４―クロロ―３―ヒドロキシブタン酸及びそのエステルの製法
AT203498B (de) Verfahren zur Herstellung von neuen Piperidyl-(2)-phenylmethanol-Derivaten
JP3081065B2 (ja) 新規アミン及びその製造法
AT273939B (de) Verfahren zur Herstellung von neuen ω-(2-Amino-halogenbenzylamino)-alkansäuren, deren Estern, Amiden und/oder Salzen
JPS6341470A (ja) イソオキサゾリジン誘導体

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase