JP3500289B2 - Thickening and gelling agent composed of cyclohexanetricarboxamide derivative - Google Patents
Thickening and gelling agent composed of cyclohexanetricarboxamide derivativeInfo
- Publication number
- JP3500289B2 JP3500289B2 JP34469197A JP34469197A JP3500289B2 JP 3500289 B2 JP3500289 B2 JP 3500289B2 JP 34469197 A JP34469197 A JP 34469197A JP 34469197 A JP34469197 A JP 34469197A JP 3500289 B2 JP3500289 B2 JP 3500289B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- organic substance
- thickening
- present
- 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.)
- Expired - Fee Related
Links
- 230000008719 thickening Effects 0.000 title claims description 40
- 239000002562 thickening agent Substances 0.000 title claims description 17
- 239000003349 gelling agent Substances 0.000 title claims description 16
- KKIVBXBGEQVMSO-UHFFFAOYSA-N cyclohexane-1,1,2-tricarboxamide Chemical class NC(=O)C1CCCCC1(C(N)=O)C(N)=O KKIVBXBGEQVMSO-UHFFFAOYSA-N 0.000 title 1
- 239000000126 substance Substances 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 60
- 239000012530 fluid Substances 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 33
- 239000007983 Tris buffer Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 230000000087 stabilizing effect Effects 0.000 claims description 10
- 238000001879 gelation Methods 0.000 claims description 9
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 230000009969 flowable effect Effects 0.000 claims description 6
- 229940125782 compound 2 Drugs 0.000 claims description 5
- 229940126214 compound 3 Drugs 0.000 claims description 5
- YSSXCDZOSXHESK-UHFFFAOYSA-N 1-n,3-n,5-n-trioctadecylcyclohexane-1,3,5-tricarboxamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C1CC(C(=O)NCCCCCCCCCCCCCCCCCC)CC(C(=O)NCCCCCCCCCCCCCCCCCC)C1 YSSXCDZOSXHESK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- CTMDFHFGBJYLTH-UHFFFAOYSA-N n-hexylcyclohexanecarboxamide Chemical compound CCCCCCNC(=O)C1CCCCC1 CTMDFHFGBJYLTH-UHFFFAOYSA-N 0.000 claims description 4
- AVZMBJURTSQXFM-UHFFFAOYSA-N N-(3,7-dimethyloctyl)cyclohexanecarboxamide Chemical compound CC(CCNC(=O)C1CCCCC1)CCCC(C)C AVZMBJURTSQXFM-UHFFFAOYSA-N 0.000 claims description 2
- UEDFGLMJKYWADV-UHFFFAOYSA-N 1-n,3-n,5-n-tridodecylcyclohexane-1,3,5-tricarboxamide Chemical compound CCCCCCCCCCCCNC(=O)C1CC(C(=O)NCCCCCCCCCCCC)CC(C(=O)NCCCCCCCCCCCC)C1 UEDFGLMJKYWADV-UHFFFAOYSA-N 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000005259 measurement Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 5
- ODNRTOSCFYDTKF-UHFFFAOYSA-N 1,3,5-trimethylcyclohexane Chemical compound CC1CC(C)CC(C)C1 ODNRTOSCFYDTKF-UHFFFAOYSA-N 0.000 description 4
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZFEOFDFKIOBFFR-UHFFFAOYSA-N n-dodecylcyclohexanecarboxamide Chemical compound CCCCCCCCCCCCNC(=O)C1CCCCC1 ZFEOFDFKIOBFFR-UHFFFAOYSA-N 0.000 description 4
- UOJWCKBTLPPNFI-UHFFFAOYSA-N n-octadecylcyclohexanecarboxamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C1CCCCC1 UOJWCKBTLPPNFI-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 and specifically Substances 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012916 structural analysis Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- PPKSYRUVTABEIE-UHFFFAOYSA-N 3,7-dimethyloctan-1-amine Chemical compound CC(C)CCCC(C)CCN PPKSYRUVTABEIE-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 description 1
- OSJHTLOGFHGOEK-UHFFFAOYSA-N [2,2-dimethyl-3-(6-methylheptanoyloxy)propyl] 6-methylheptanoate Chemical compound CC(C)CCCCC(=O)OCC(C)(C)COC(=O)CCCCC(C)C OSJHTLOGFHGOEK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- QTDSLDJPJJBBLE-PFONDFGASA-N octyl (z)-octadec-9-enoate Chemical compound CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC QTDSLDJPJJBBLE-PFONDFGASA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、オイル等の流動性
有機物の増粘・ゲル化に好適なシクロヘキサンアルキル
アミド誘導体からなる流動性有機物用の増粘・ゲル化剤
及び流動性有機物乃至はこれを含有する組成物の増粘・
ゲル化方法あるいは安定化方法に関する。TECHNICAL FIELD The present invention relates to a thickening / gelling agent for a fluid organic substance and a fluid organic substance or a liquid organic substance comprising a cyclohexanealkylamide derivative suitable for thickening / gelling a fluid organic substance such as oil. Thickening of compositions containing
The present invention relates to a gelation method or a stabilization method.
【０００２】なお、本明細書に用いる「増粘・ゲル化」
の語は、増粘及び／又はゲル化を意味する。"Thickening / gelation" used in the present specification
The term means thickening and / or gelling.
【０００３】[0003]
【従来の技術】液体を増粘・ゲル化する方法は、産業上
非常に重要な技術であり、例えば、準安定状態の乳化物
であるマヨネーズやサラダドレッシング等が長期間安定
なのも水性成分に増粘剤を加え増粘安定化しているため
である。又、例えばタンカー事故による重油などの流出
事故などの場合適切な重油を固化する技術があれば、固
体として重油を回収し得るため、現在のような手間がか
かりその割には効果の少ない回収を行う必要がなくな
る。又、食用の廃油の処理方法として現在用いられてい
る固化方法は１２−ヒドロキシステアリン酸のゲル化作
用を利用したものである。2. Description of the Related Art A method of thickening / gelling a liquid is a very important technology in industry, and for example, mayonnaise and salad dressing, which are metastable emulsions, are stable as an aqueous component for a long period of time. This is because a thickener is added to stabilize the viscosity. Also, for example, in the case of a spill accident such as heavy oil due to a tanker accident, if there is a technique for solidifying the appropriate heavy oil, it is possible to recover the heavy oil as a solid. There is no need to do it. The solidification method currently used as a method for treating edible waste oil utilizes the gelling action of 12-hydroxystearic acid.
【０００４】かかる状況から種々の増粘・ゲル化剤が開
発されてきた。この様なものの成功例としては、例え
ば、アルキルアクリレートコポリマー等が挙げられる
が、それらは何れも水系での増粘・ゲル化剤であり、有
機成分に対する増粘・ゲル化剤は１２−ヒドロキシステ
アリン酸のみであった。しかしながら、１２−ヒドロキ
システアリン酸はゲル化を調整する手段が無いため、固
化するか液体のままかの何れかの状態にしか系を誘導で
きなかった。即ち、流動性を有する有機物質乃至はこれ
を含有する組成物の増粘・ゲル化手段が求められてい
た。Under these circumstances, various thickening / gelling agents have been developed. Examples of successful examples of such products include, for example, alkyl acrylate copolymers, all of which are aqueous thickening / gelling agents, and the thickening / gelling agent for organic components is 12-hydroxystearin. Only acid. However, since 12-hydroxystearic acid has no means for controlling the gelation, the system can be induced only in a state where it solidifies or remains liquid. That is, there has been a demand for means for increasing the viscosity and gelation of a fluid organic substance or a composition containing the same.
【０００５】一方、後記一般式（Ｉ）に表される化合物
が流動性を有する有機物質に対して優れた増粘・ゲル化
作用を発揮することは知られていない。On the other hand, it is not known that the compound represented by the general formula (I) described below exerts an excellent thickening / gelling action on an organic substance having fluidity.
【０００６】[0006]
【発明が解決しようとする課題】本発明はこの様な状況
下に為されたものであって、流動性を有する有機物質乃
至はこれを含有する組成物の増粘・ゲル化手段あるいは
安定化手段を提供することを課題とする。SUMMARY OF THE INVENTION The present invention has been made under such circumstances, and is a means for thickening / gelling or stabilizing a flowable organic substance or a composition containing the same. It is an object to provide means.
【０００７】[0007]
【課題を解決するための手段】本発明者らはこの様な状
況に鑑み、流動性を有する有機物質乃至はこれを含有す
る組成物の増粘・ゲル化あるいは安定化を可能とする物
質を求めて、鋭意研究を重ねた結果、本発明者らによっ
て新たに合成された以下の一般式（Ｉ）に表される化合
物群が前記性質を有することを見出し、本発明を完成さ
せた。In view of such a situation, the present inventors have selected a substance capable of thickening, gelling or stabilizing an organic substance having fluidity or a composition containing the same. As a result of intensive investigations, the inventors have found that a group of compounds newly represented by the following general formula (I) newly synthesized by the present inventors have the above-mentioned properties, and completed the present invention.
【０００８】すなわち、本発明は、下記一般式（Ｉ）で
表される化合物（以下、本発明に係る化合物ともいう）
から選ばれる１種乃至は２種以上からなる流動性有機物
質用の増粘・ゲル化剤、あるいは、流動性有機物質と、
上記本発明に係る化合物から選ばれる１種乃至は２種以
上とを混合、加温し、相溶させた後、冷却することを特
徴とする流動性有機物質の増粘・ゲル化方法を提供す
る。That is, the present invention is a compound represented by the following general formula (I) (hereinafter, also referred to as a compound according to the present invention)
A thickening / gelling agent for a fluid organic substance, or a fluid organic substance, which comprises one or more selected from
Provided is a method for thickening / gelling a fluid organic substance, which comprises mixing, heating, and compatibilizing one or more selected from the compounds according to the present invention, and then cooling. To do.
【０００９】さらに、本発明は、流動性有機物質を含有
する組成物を安定化する方法において、上記本発明に係
る化合物から選ばれる１種乃至は２種以上を用いた流動
性有機物質の増粘・ゲル化を含むことを特徴とする流動
性有機物質含有組成物の安定化方法を提供するものであ
る。Furthermore, the present invention provides a method for stabilizing a composition containing a flowable organic substance, which comprises using one or more selected from the compounds according to the present invention to increase the flowable organic substance. The present invention provides a method for stabilizing a composition containing a fluid organic substance, which comprises viscous / gelling.
【００１０】ここで、一般式（Ｉ）で表される本発明に
係る化合物とは次のものをいう。The compounds represented by the general formula (I) according to the present invention are as follows.
【００１１】[0011]
【化９】 [Chemical 9]
【００１２】（但し、式中Ｒはそれぞれ独立に炭素数４
〜２０の直鎖状、分岐鎖状又は環状の構造を有するアル
キル基を表し、Ｒ’はそれぞれ独立に水素原子又は炭素
数１〜４のアルキル基を表す。）(However, in the formula, each R independently has 4 carbon atoms.
~ 20 represents an alkyl group having a linear, branched or cyclic structure, and R'independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. )
【００１３】本発明に係る一般式（Ｉ）で表される化合
物として、具体的には、一般式（ＩＩ）で表されるエク
ァトリアル型構造を有する化合物が挙げられる。Specific examples of the compound represented by the general formula (I) according to the present invention include compounds having an equatorial structure represented by the general formula (II).
【００１４】[0014]
【化１０】 [Chemical 10]
【００１５】（但し、式中Ｒはそれぞれ独立に炭素数４
〜２０の直鎖状、分岐鎖状又は環状の構造を有するアル
キル基を表し、Ｒ’はそれぞれ独立に炭素数１〜４のア
ルキル基を表す。）(However, in the formula, each R independently has 4 carbon atoms.
~ 20 represents an alkyl group having a linear, branched or cyclic structure, and R'independently represents an alkyl group having 1 to 4 carbon atoms. )
【００１６】さらに、一般式（ＩＩ）で表されるエクァ
トリアル型構造を有する化合物として、具体的には、式
（ＩＩＩ）で表されるｃｉｓ−１，３，５−トリス（ヘ
キシルアミノカルボニル）シクロヘキサン（化合物
１）、式（ＩＶ）で表されるｃｉｓ−１，３，５−トリ
ス（ドデシルアミノカルボニル）シクロヘキサン（化合
物２）、式（Ｖ）で表されるｃｉｓ−１，３，５−トリ
ス（オクタデシルアミノカルボニル）シクロヘキサン
（化合物３）、式（ＶＩ）で表されるｃｉｓ−１，３，
５−トリス（Ｎ−（３，７−ジメチルオクチル）アミノ
カルボニル）シクロヘキサン（化合物４）等を挙げるこ
とができる。Further, as the compound having the equatorial structure represented by the general formula (II), specifically, cis-1,3,5-tris (hexylaminocarbonyl) cyclohexane represented by the formula (III) is used. (Compound 1), cis-1,3,5-tris (dodecylaminocarbonyl) cyclohexane represented by Formula (IV) (Compound 2), cis-1,3,5-Tris represented by Formula (V) (Octadecylaminocarbonyl) cyclohexane (Compound 3), cis-1,3 represented by formula (VI)
Examples thereof include 5-tris (N- (3,7-dimethyloctyl) aminocarbonyl) cyclohexane (Compound 4).
【００１７】[0017]
【化１１】 [Chemical 11]
【００１８】[0018]
【化１２】 [Chemical 12]
【００１９】[0019]
【化１３】 [Chemical 13]
【００２０】[0020]
【化１４】 [Chemical 14]
【００２１】[0021]
【発明の実施の形態】以下、本発明を具体的に説明す
る。まず、本発明に係る化合物について説明する。
（１）本発明に係る化合物
本発明に係る化合物は、シクロヘキサントリカルボキサ
ミドのアルキル誘導体であり、化学式は上記一般式
（Ｉ）に表される通りである。BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be specifically described below. First, the compound according to the present invention will be described. (1) Compound According to the Present Invention The compound according to the present invention is an alkyl derivative of cyclohexanetricarboxamide, and its chemical formula is as represented by the above general formula (I).
【００２２】本発明に係る化合物に於いては、３つのア
ルキルアミノカルボニル基の６員環への結合の仕方によ
って立体異性体が存在する。本発明においては、少なく
とも２つのアルキルアミノカルボニル基の結合がエクァ
トリアル結合である化合物が好ましく、さらに３つのア
ルキルアミノカルボニル基の全てがエクァトリアル結合
である上記一般式（ＩＩ）で示されるエクァトリアル型
構造の化合物がより好ましい。本発明に係る化合物にお
いては、この様にアルキルアミノカルボニル基がエクァ
トリアル結合を取る様な化合物が流動性有機物質に対し
てより優れた増粘・ゲル化作用を有するからである。In the compound according to the present invention, stereoisomers exist depending on the way of bonding the three alkylaminocarbonyl groups to the 6-membered ring. In the present invention, a compound in which the bond of at least two alkylaminocarbonyl groups is an equatorial bond is preferable, and further, the compound having the equatorial structure represented by the above general formula (II) in which all of the three alkylaminocarbonyl groups are equatorial bonds Compounds are more preferred. This is because, in the compound according to the present invention, a compound in which an alkylaminocarbonyl group has an equatorial bond as described above has a more excellent thickening / gelling action on a fluid organic substance.
【００２３】本発明に係る化合物のうち、少なくとも２
つアルキルアミノカルボニル基の結合がエクァトリアル
結合である化合物として、具体的には、上記式（ＩＩ
Ｉ）で表されるｃｉｓ−１，３，５−トリス（ヘキシル
アミノカルボニル）シクロヘキサン（化合物１）、式
（ＩＶ）で表されるｃｉｓ−１，３，５−トリス（ドデ
シルアミノカルボニル）シクロヘキサン（化合物２）、
式（Ｖ）で表されるｃｉｓ−１，３，５−トリス（オク
タデシルアミノカルボニル）シクロヘキサン（化合物
３）、式（ＶＩ）で表されるｃｉｓ−１，３，５−トリ
ス（Ｎ−（３，７−ジメチルオクチル）アミノカルボニ
ル）シクロヘキサン（化合物４）、や下記式（ＶＩＩ）
で表されるｔｒａｎｓ−１，３，５−トリメチル−１，
３，５−トリス（Ｎ−ラウリルアミノカルボニル）シク
ロヘキサン（化合物５）、式（ＶＩＩＩ）で表されるｔ
ｒａｎｓ−１，３，５−トリメチル−１，３，５−トリ
ス（Ｎ−ステアリルアミノカルボニル）シクロヘキサン
（化合物６）等を挙げることができる。At least 2 of the compounds according to the present invention
As the compound in which the bond of the alkylaminocarbonyl group is an equatorial bond, specifically, the compound represented by the above formula (II
I) cis-1,3,5-tris (hexylaminocarbonyl) cyclohexane (Compound 1), cis-1,3,5-tris (dodecylaminocarbonyl) cyclohexane (Compound 1) Compound 2),
Cis-1,3,5-tris (octadecylaminocarbonyl) cyclohexane (compound 3) represented by formula (V), cis-1,3,5-tris (N- (3) represented by formula (VI) , 7-Dimethyloctyl) aminocarbonyl) cyclohexane (Compound 4), and the following formula (VII)
Represented by trans-1,3,5-trimethyl-1,
3,5-Tris (N-laurylaminocarbonyl) cyclohexane (Compound 5), t represented by the formula (VIII)
rans-1,3,5-trimethyl-1,3,5-tris (N-stearylaminocarbonyl) cyclohexane (Compound 6) and the like can be mentioned.
【００２４】また、これらの内では上記一般式（ＩＩ）
で示されるエクァトリアル型構造の化合物である化合物
１〜４が特に上記増粘・ゲル化作用が強く好ましい。Among them, the above general formula (II)
Compounds 1 to 4, which are compounds having an equatorial structure represented by, are particularly preferable because of their strong thickening / gelling action.
【００２５】[0025]
【化１５】 [Chemical 15]
【００２６】[0026]
【化１６】 [Chemical 16]
【００２７】本発明に係る化合物は何れも既知の化合物
より、製造することができる。これらの化合物は例え
ば、次に示す方法で製造すればよい。即ち、目的化合物
に対応する立体特性を有する１，３，５−シクロヘキサ
ントリカルボン酸を塩化チオニルで酸クロライドに変換
し、これに目的化合物に対応するアルキルアミンを反応
させればよい。かくして得られた生成物は再結晶やカラ
ムクロマトグラフィー等の通常の精製手段により精製で
きる。Any of the compounds of the present invention can be prepared from known compounds. These compounds may be produced, for example, by the method shown below. That is, 1,3,5-cyclohexanetricarboxylic acid having steric characteristics corresponding to the target compound may be converted to acid chloride with thionyl chloride, and this may be reacted with an alkylamine corresponding to the target compound. The product thus obtained can be purified by ordinary purification means such as recrystallization or column chromatography.
【００２８】かくして得られる本発明に係る化合物は何
れも流動性を有する有機物質乃至はこれを含有する組成
物を増粘・ゲル化あるいは安定化させる作用に優れる。Any of the compounds according to the present invention thus obtained is excellent in the action of thickening, gelling or stabilizing a fluid organic substance or a composition containing the same.
【００２９】（２）本発明の流動性有機物質用増粘・ゲ
ル化剤および流動性有機物質の増粘・ゲル化方法
本発明の流動性有機物質用の増粘・ゲル化剤は、上記本
発明に係る化合物から選ばれる１種又は２種以上からな
る。本発明の増粘・ゲル化剤には、さらに必要に応じて
基剤等の任意成分を配合することが可能であり、この様
な任意成分と上記本発明に係る化合物とを配合して本発
明の増粘・ゲル化剤を種々の剤形に製剤化することも可
能である。(2) Thickening / gelling agent for fluid organic substance and method for thickening / gelling fluid organic substance of the present invention, the thickening / gelling agent for fluid organic substance of the present invention is as described above. It consists of one or more selected from the compounds according to the present invention. The thickening / gelling agent of the present invention may further contain an optional component such as a base, if necessary, and such an optional component and the compound according to the present invention may be added to form a composition. It is also possible to formulate the thickening / gelling agent of the invention into various dosage forms.
【００３０】本発明の流動性有機物質の増粘・ゲル化方
法は、流動性有機物質と、上記本発明に係る化合物から
選ばれる１種又は２種以上とを混合、加温し、相溶させ
た後、冷却することを特徴とする。The method for thickening / gelling a fluid organic substance of the present invention comprises mixing the fluid organic substance with one or more selected from the compounds according to the present invention, heating them, and making them compatible with each other. It is characterized in that it is cooled after being allowed to do so.
【００３１】本発明の流動性有機物質の増粘・ゲル化方
法における、上記本発明に係る化合物の使用量として
は、用いる本発明に係る化合物や対象とする流動性有機
物質の種類にもよるが、当該流動性有機物質１０００重
量部に対して、概ね０．１〜１００重量部、より好まし
くは０．５〜９０重量部、更に好ましくは１〜８０重量
部の範囲を挙げることができる。この場合、本発明に係
る化合物は唯１種のみを用いても良いし２種以上を用い
ても良い。The amount of the compound according to the present invention used in the thickening / gelling method of the fluid organic substance of the present invention depends on the type of the compound according to the present invention to be used and the target fluid organic substance. However, the range of about 0.1 to 100 parts by weight, more preferably 0.5 to 90 parts by weight, still more preferably 1 to 80 parts by weight can be mentioned with respect to 1000 parts by weight of the fluid organic substance. In this case, the compounds according to the present invention may be used alone or in combination of two or more.
【００３２】また、本発明の増粘・ゲル化方法において
は、上記本発明の増粘・ゲル化剤を用いることも可能で
あり、その場合には増粘・ゲル化剤の使用量を、本発明
に係る化合物の使用量として上記範囲となるように調整
すればよい。In the thickening / gelling method of the present invention, it is also possible to use the above-mentioned thickening / gelling agent of the present invention. In that case, the amount of the thickening / gelling agent used is The amount of the compound according to the present invention to be used may be adjusted within the above range.
【００３３】本発明の流動性有機物質の増粘・ゲル化方
法によれば、さらに、流動性有機物質を含有する組成物
を増粘・ゲル化することも可能である。この場合の上記
本発明に係る化合物の使用量は、組成物中の流動性有機
物質量に対する量として上記範囲となるようにすればよ
い。According to the method of thickening / gelling a fluid organic substance of the present invention, it is possible to further thicken / gel the composition containing the fluid organic substance. In this case, the amount of the compound of the present invention used may be in the above range as the amount with respect to the amount of the fluid organic substance in the composition.
【００３４】本発明の流動性有機物質の増粘・ゲル化方
法においては、上記割合で流動性有機物質と本発明に係
る化合物を混合した後、加温して両者を相溶させる。加
温の際の温度については、両者が相溶する温度であれば
特に制限されないが、１００℃を越えないことが好まし
く、流動性有機物質の沸点が１００℃以下の場合には、
沸点程度が好ましい。また、この温度は、用いる本発明
に係る化合物や対象とする流動性有機物質の種類によっ
て適宜選択されうるものである。In the method of thickening / gelling a fluid organic substance of the present invention, the fluid organic substance and the compound of the present invention are mixed in the above proportions and then heated to make them compatible with each other. The temperature at the time of heating is not particularly limited as long as they are compatible with each other, but it is preferable that the temperature does not exceed 100 ° C, and when the boiling point of the fluid organic substance is 100 ° C or less,
The boiling point is preferable. Further, this temperature can be appropriately selected depending on the kind of the compound according to the present invention to be used and the target fluid organic substance.
【００３５】本発明の増粘・ゲル化方法においては上記
相溶後、冷却を行うが、この冷却に関しても特に制限さ
れず、室温で徐冷してもよいし、氷冷等により強制的に
冷却してもよい。In the thickening / gelling method of the present invention, cooling is performed after the above-mentioned compatibility, but the cooling is not particularly limited, and may be gradually cooled at room temperature or forcedly by ice cooling or the like. You may cool.
【００３６】上記本発明の増粘・ゲル化剤、あるいは、
増粘・ゲル化方法が適用される流動性有機物質として
は、例えば、四塩化炭素、テトラヒドロフラン、ヘキサ
ン、シクロヘキサン、ベンゼン、トルエン、クロロベン
ゼン、ピリジン等のような有機溶剤類、ケロシン、ガソ
リン、軽油、重油等の燃料、オリーブ油、大豆油、コー
ン油、ヒマシ油、牛脂、ホホバ油等の動植物油、スクワ
ラン、流動パラフィン等の鉱物油、ジメチルポリシロキ
サンやメチルフェニルポリシロキサン等のシリコーン
類、オレイン酸オクチルドデシル、グリセリルトリイソ
オクタネート、ネオペンチルグリコールジイソオクタネ
ート等の合成エステル類が例示できる。本発明は、ま
た、これら流動性有機物質の混合物にも適用され得る。The thickening / gelling agent of the present invention, or
Examples of fluid organic substances to which the thickening / gelling method is applied include, for example, carbon tetrachloride, tetrahydrofuran, hexane, cyclohexane, benzene, toluene, chlorobenzene, organic solvents such as pyridine, kerosene, gasoline, light oil, Fuels such as heavy oil, olive oil, soybean oil, corn oil, castor oil, beef tallow, jojoba oil and other animal and vegetable oils, squalane, mineral oils such as liquid paraffin, silicones such as dimethylpolysiloxane and methylphenylpolysiloxane, octyl oleate Examples thereof include synthetic esters such as dodecyl, glyceryl triisooctanoate, neopentyl glycol diisooctanoate. The invention can also be applied to mixtures of these free-flowing organic substances.
【００３７】（３）本発明の流動性有機物質含有組成物
の安定化方法
本発明の流動性有機物質含有組成物の安定化方法は、上
記本発明に係る化合物から選ばれる１種乃至は２種以上
を用いた流動性有機物質の増粘・ゲル化を含むことを特
徴とするものである。(3) Method for stabilizing composition containing fluid organic substance of the present invention The method for stabilizing composition containing fluid organic substance of the present invention is one or two selected from the compounds according to the present invention. It is characterized by including thickening and gelling of a fluid organic substance using at least one species.
【００３８】本発明の安定化方法における、上記本発明
に係る化合物を用いた流動性有機物質の増粘・ゲル化に
ついては、上記本発明の流動性有機物質の増粘・ゲル化
方法で説明した通りである。Regarding the thickening / gelling of the fluid organic substance using the compound of the present invention in the stabilization method of the present invention, the thickening / gelling method of the liquid organic substance of the present invention will be described. As I did.
【００３９】この様な本発明の安定化方法として、具体
的には、流動性有機物質を含有する組成物に、上記本発
明に係る化合物の適当量を混合、加温し、相溶させた
後、冷却する方法や、流動性有機物質含有組成物の原料
である流動性有機物質に、予め上記本発明に係る化合物
の適当量を添加混合し、加温、相溶させた後、冷却し
て、前記流動性有機物質の増粘・ゲル化物を製造し、こ
れを組成物に配合する方法等が挙げられる。As such a stabilizing method of the present invention, specifically, a composition containing a fluid organic substance is mixed with an appropriate amount of the compound of the present invention, heated, and made compatible. After that, a method of cooling or a fluid organic substance which is a raw material of the composition containing a fluid organic substance is added and mixed with an appropriate amount of the compound according to the present invention in advance, heated and mixed to be cooled, and then cooled. Then, a method of producing a thickened / gelled product of the fluid organic substance and blending it with a composition can be mentioned.
【００４０】本発明の安定化方法が適用される組成物と
しては、流動性有機物質を含有する組成物であれば特に
制限されないが、具体的には、化粧料、ペイント、食
品、医薬品等が例示できる。The composition to which the stabilization method of the present invention is applied is not particularly limited as long as it is a composition containing a fluid organic substance, and specifically, cosmetics, paints, foods, pharmaceuticals and the like are used. It can be illustrated.
【００４１】[0041]
【実施例】以下に実施例を示して本発明について更に詳
細に説明するが、本発明がこれら実施例にのみ限定を受
けないことは言うまでもない。The present invention will be described in more detail with reference to the following examples, but it goes without saying that the present invention is not limited to these examples.
【００４２】[0042]
【実施例１】 ｃｉｓ−１，３，５−トリス（ヘキシル
アミノカルボニル）シクロヘキサン（化合物１）の合成
ｃｉｓ−１，３，５−シクロヘキサントリカルボン酸２
ｇをクロロホルム５０ｍｌに溶解させ、これに６ｇの塩
化チオニルを加え、室温で１時間撹拌し、反応液を濃縮
した。これにヘキシルアミン３ｇを５０ｍｌの塩化メチ
レンと１０ｍｌのトリエチルアミンに溶かして加え、２
時間加熱撹拌した。析出した結晶を集め水洗し、化合物
１を５ｇ得た。このものの元素分析、ＩＲ、ＮＭＲ等の
示性値は構造を支持していた。ＩＲ測定結果を以下に示
す。Example 1 Synthesis of cis-1,3,5-tris (hexylaminocarbonyl) cyclohexane (Compound 1) cis-1,3,5-cyclohexanetricarboxylic acid 2
g was dissolved in 50 ml of chloroform, 6 g of thionyl chloride was added thereto, the mixture was stirred at room temperature for 1 hour, and the reaction solution was concentrated. Hexylamine (3 g) was dissolved in 50 ml of methylene chloride and 10 ml of triethylamine and added to the mixture.
The mixture was heated and stirred for an hour. The precipitated crystals were collected and washed with water to obtain 5 g of compound 1. The characteristic values of elemental analysis, IR, NMR and the like supported the structure. The IR measurement results are shown below.
【００４３】（ＩＲ測定結果（ｃｍ-1）、ＫＢｒ錠剤
法）３８４４、３３００、２９２８、２３３２、１５５
４、１３９０、１２５８、１１５２(IR measurement result (cm -1 ), KBr tablet method) 3844, 3300, 2928, 2332, 155
4, 1390, 1258, 1152
【００４４】[0044]
【実施例２】 ｃｉｓ−１，３，５−トリス（ドデシル
アミノカルボニル）シクロヘキサン（化合物２）の合成
ｃｉｓ−１，３，５−シクロヘキサントリカルボン酸２
ｇをクロロホルム５０ｍｌに溶解させ、これに６ｇの塩
化チオニルを加え、室温で１時間撹拌し、反応液を濃縮
した。これにラウリルアミン６ｇを５０ｍｌの塩化メチ
レンと１０ｍｌのトリエチルアミンに溶かして加え、２
時間加熱撹拌した。析出した結晶を集め水洗し、化合物
２を８ｇ得た。このものの元素分析、ＩＲ、ＮＭＲ等の
示性値は構造を支持していた。ＩＲ測定結果を以下に示
す。Example 2 Synthesis of cis-1,3,5-tris (dodecylaminocarbonyl) cyclohexane (Compound 2) cis-1,3,5-cyclohexanetricarboxylic acid 2
g was dissolved in 50 ml of chloroform, 6 g of thionyl chloride was added thereto, the mixture was stirred at room temperature for 1 hour, and the reaction solution was concentrated. To this, 6 g of laurylamine was dissolved in 50 ml of methylene chloride and 10 ml of triethylamine, and added.
The mixture was heated and stirred for an hour. The precipitated crystals were collected and washed with water to obtain 8 g of compound 2. The characteristic values of elemental analysis, IR, NMR and the like supported the structure. The IR measurement results are shown below.
【００４５】（ＩＲ測定結果（ｃｍ-1）、ＫＢｒ錠剤
法）３６７６、３３００、２９２４、１６４４、１４６
８、１３１４、１２０６(IR measurement result (cm -1 ), KBr tablet method) 3676, 3300, 2924, 1644, 146
8, 1314, 1206
【００４６】[0046]
【実施例３】 ｃｉｓ−１，３，５−トリス（オクタデ
シルアミノカルボニル）シクロヘキサン（化合物３）の
合成
ｃｉｓ−１，３，５−シクロヘキサントリカルボン酸２
ｇをクロロホルム５０ｍｌに溶解させ、これに６ｇの塩
化チオニルを加え、室温で１時間撹拌し、反応液を濃縮
した。これにステアリルアミン７ｇを５０ｍｌの塩化メ
チレンと１０ｍｌのトリエチルアミンに溶かして加え、
２時間加熱撹拌した。析出した結晶を集め水洗し、化合
物３を１０ｇ得た。このものの元素分析、ＩＲ、ＮＭＲ
等の示性値は構造を支持していた。ＩＲ測定結果を以下
に示す。Example 3 Synthesis of cis-1,3,5-tris (octadecylaminocarbonyl) cyclohexane (Compound 3) cis-1,3,5-cyclohexanetricarboxylic acid 2
g was dissolved in 50 ml of chloroform, 6 g of thionyl chloride was added thereto, the mixture was stirred at room temperature for 1 hour, and the reaction solution was concentrated. To this, 7 g of stearylamine dissolved in 50 ml of methylene chloride and 10 ml of triethylamine was added,
The mixture was heated and stirred for 2 hours. The precipitated crystals were collected and washed with water to obtain 10 g of compound 3. Elemental analysis, IR, NMR of this product
Indicative values such as were in favor of the structure. The IR measurement results are shown below.
【００４７】（ＩＲ測定結果（ｃｍ-1）、ＫＢｒ錠剤
法）３４５６、３０９２、２８５６、１６４４、１４７
０、１３１６、１２０６(IR measurement result (cm -1 ), KBr tablet method) 3456, 3092, 2856, 1644, 147
0, 1316, 1206
【００４８】[0048]
【実施例４】 ｃｉｓ−１，３，５−トリス（Ｎ−
（３，７−ジメチルオクチル）アミノカルボニル）シク
ロヘキサン（化合物４）の合成
ｃｉｓ−１，３，５−シクロヘキサントリカルボン酸２
ｇをクロロホルム５０ｍｌに溶解させ、これに６ｇの塩
化チオニルを加え、室温で１時間撹拌し、反応液を濃縮
した。これに３，７−ジメチルオクチルアミン５ｇを５
０ｍｌの塩化メチレンと１０ｍｌのトリエチルアミンに
溶かして加え、２時間加熱撹拌した。析出した結晶を集
め水洗し、化合物４を６ｇ得た。このものの元素分析、
ＩＲ、ＮＭＲ等の示性値は構造を支持していた。ＩＲ測
定結果を以下に示す。Example 4 cis-1,3,5-tris (N-
Synthesis of (3,7-dimethyloctyl) aminocarbonyl) cyclohexane (Compound 4) cis-1,3,5-cyclohexanetricarboxylic acid 2
g was dissolved in 50 ml of chloroform, 6 g of thionyl chloride was added thereto, the mixture was stirred at room temperature for 1 hour, and the reaction solution was concentrated. Add 5 g of 3,7-dimethyloctylamine to this.
It was dissolved in 0 ml of methylene chloride and 10 ml of triethylamine and added, and the mixture was heated with stirring for 2 hours. The precipitated crystals were collected and washed with water to obtain 6 g of compound 4. Elemental analysis of this thing,
IR, NMR and other indications supported the structure. The IR measurement results are shown below.
【００４９】（ＩＲ測定結果（ｃｍ-1）、ＫＢｒ錠剤
法）３３０８、２９５６、２８７２、１５５２、１３８
４、１２５６、１０３２(IR measurement result (cm -1 ), KBr tablet method) 3308, 2956, 2872, 1552, 138
4, 1256, 1032
【００５０】[0050]
【実施例５】 増粘・ゲル化作用試験
表１に示す各種流動性有機物質を、試験管に１ｃｍ3ず
つ秤りとり、これに秤量した上記実施例１で得られた化
合物１を加え混合し、相溶するまで各流動性有機物質に
ついての適温（沸点が１００℃未満の流動性有機物質に
ついては沸点、それ以外は１００℃）で加熱撹拌した。
相溶したものを２５℃まで冷却し、ゲル化しているか否
かを肉眼で判定した。ゲル化をしていた場合には化合物
１の添加量を減じ、ゲル化をしていなかった場合には添
加量を増やし、ゲル化する最低量（ｍｇ）を求めた。ま
た、上記実施例２〜４で得られた化合物２〜４について
も、同様にして、各種流動性有機物質をゲル化する最低
量（ｍｇ）を求めた。結果を表１に示す。尚、表中の
「ゲル様」の記載はゲルの形成は見られなかったが、ゲ
ルっぽい状態であったことを意味する。[Example 5] Thickening / gelling action test Various fluid organic substances shown in Table 1 were weighed in test tubes at 1 cm 3 each, and the weighed compound 1 obtained in the above Example 1 was added and mixed. Then, the mixture was heated and stirred at a suitable temperature for each fluid organic substance (boiling point for fluid organic substances having a boiling point of less than 100 ° C., other than 100 ° C.) until they are compatible.
The compatible product was cooled to 25 ° C., and it was visually judged whether gelation occurred. The minimum amount (mg) of gelation was determined by decreasing the addition amount of Compound 1 when gelation occurred and increasing the addition amount when not gelation. Further, with respect to the compounds 2 to 4 obtained in the above Examples 2 to 4, the minimum amount (mg) of gelling various fluid organic substances was determined in the same manner. The results are shown in Table 1. In the table, "gel-like" means that no gel was found, but it was in a gel-like state.
【００５１】[0051]
【表１】 [Table 1]
【００５２】この結果から、上記実施例で得られた本発
明に係る化合物１〜４は何れも流動性有機物質を増粘・
ゲル化する作用に優れることが判る。From these results, all of the compounds 1 to 4 according to the present invention obtained in the above examples thicken the fluid organic substance.
It can be seen that the gelling action is excellent.
【００５３】[0053]
【実施例６】 ｔｒａｎｓ−１，３，５−トリメチル−
１，３，５−トリス（Ｎ−ラウリルアミノカルボニル）
シクロヘキサン（化合物５）の合成
ｔｒａｎｓ−１，３，５−トリヒドロキシカルボニル−
１，３，５−トリメチルシクロヘキサン２．３ｇをクロ
ロホルム５０ｍｌに溶解させ、これに６ｇの塩化チオニ
ルを加え、室温で１時間撹拌し、反応液を濃縮した。こ
れにラウリルアミン６ｇを５０ｍｌの塩化メチレンと１
０ｍｌのトリエチルアミンに溶かして加え、２時間加熱
撹拌した。析出した結晶を集め水洗し、化合物５を５．
５ｇ得た。このものの元素分析、ＮＭＲ等の示性値は構
造を支持していた。Example 6 trans-1,3,5-trimethyl-
1,3,5-Tris (N-laurylaminocarbonyl)
Synthesis of cyclohexane (Compound 5) trans-1,3,5-trihydroxycarbonyl-
2.3 g of 1,3,5-trimethylcyclohexane was dissolved in 50 ml of chloroform, 6 g of thionyl chloride was added thereto, the mixture was stirred at room temperature for 1 hour, and the reaction liquid was concentrated. Add 6 g of laurylamine to 50 ml of methylene chloride and
It was dissolved in 0 ml of triethylamine and added, and the mixture was heated with stirring for 2 hours. The precipitated crystals were collected and washed with water to prepare compound 5.
5 g was obtained. The structural analysis of this product was supported by the elemental analysis and NMR.
【００５４】[0054]
【実施例７】 ｔｒａｎｓ−１，３，５−トリメチル−
１，３，５−トリス（Ｎ−ステアリルアミノカルボニ
ル）シクロヘキサン（化合物６）の合成
ｔｒａｎｓ−１，３，５−トリヒドロキシカルボニル−
１，３，５−トリメチルシクロヘキサン２．３ｇをクロ
ロホルム５０ｍｌに溶解させ、これに６ｇの塩化チオニ
ルを加え、室温で１時間撹拌し、反応液を濃縮した。こ
れにステアリルアミン７ｇを５０ｍｌの塩化メチレンと
１０ｍｌのトリエチルアミンに溶かして加え、２時間加
熱撹拌した。析出した結晶を集め水洗し、化合物６を１
１ｇ得た。このものの元素分析、ＮＭＲ等の示性値は構
造を支持していた。Example 7 trans-1,3,5-trimethyl-
Synthesis of 1,3,5-tris (N-stearylaminocarbonyl) cyclohexane (Compound 6) trans-1,3,5-trihydroxycarbonyl-
2.3 g of 1,3,5-trimethylcyclohexane was dissolved in 50 ml of chloroform, 6 g of thionyl chloride was added thereto, the mixture was stirred at room temperature for 1 hour, and the reaction liquid was concentrated. To this, 7 g of stearylamine was dissolved in 50 ml of methylene chloride and 10 ml of triethylamine and added, and the mixture was heated and stirred for 2 hours. The precipitated crystals were collected and washed with water to give compound 6 as 1
1 g was obtained. The structural analysis of this product was supported by the elemental analysis and NMR.
【００５５】[0055]
【発明の効果】本発明によれば、新たに製造された一般
式（Ｉ）で表される化合物を用いて、流動性を有する有
機物質乃至はこれを含有する組成物を増粘・ゲル化する
こと、あるいは、安定化することが可能である。INDUSTRIAL APPLICABILITY According to the present invention, a newly produced compound represented by the general formula (I) is used to thicken or gelate an organic substance having fluidity or a composition containing the same. It is possible to do or stabilize.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 白井 汪芳 長野県上田市常田３丁目15番１号 信州 大学繊維学部内 (72)発明者 井柳 宏一 神奈川県横浜市戸塚区柏尾町560ポーラ 化成工業株式会社戸塚研究所内 (56)参考文献 特開 平10−212213（ＪＰ，Ａ) 特開 平８−295653（ＪＰ，Ａ) 特開 平９−208522（ＪＰ，Ａ) Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅ ｒｓ，Ｖｏｌ．36， Ｎｏ．18，ｐｐ. 3255−3258，（1995) (58)調査した分野(Int.Cl.7，ＤＢ名) C09K 3/00 103 C07C 233/58 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Shiho Uiyoshi 3-15-1, Tsuneta, Ueda City, Nagano Prefecture Shinshu University Faculty of Textile Sciences (72) Inventor Koichi Iyanagi 560 Pola Kasei, Kashio-cho, Totsuka-ku, Yokohama, Kanagawa Prefecture (56) Reference JP 10-212213 (JP, A) JP 8-295653 (JP, A) JP 9-208522 (JP, A) Tetrahedron Letters, Vol. 36, No. 18, pp. 3255-3258, (1995) (58) Fields investigated (Int.Cl. 7 , DB name) C09K 3/00 103 C07C 233/58 CA (STN) REGISTRY (STN)
Claims (5)
れる１種乃至は２種以上からなる流動性有機物質用の増
粘・ゲル化剤。 【化１】 （但し、式中Ｒはそれぞれ独立に炭素数４〜２０の直鎖
状、分岐鎖状又は環状の構造を有するアルキル基を表
し、Ｒ’はそれぞれ独立に水素原子又は炭素数１〜４の
アルキル基を表す。）1. A thickening / gelling agent for fluid organic substances, which comprises one or more selected from compounds represented by formula (I). [Chemical 1] (However, in the formula, each R independently represents an alkyl group having a linear, branched, or cyclic structure having 4 to 20 carbon atoms, and R ′ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Represents a group.)
ル型構造を有する化合物であることを特徴とする請求項
１に記載の増粘・ゲル化剤。 【化２】 （但し、式中Ｒはそれぞれ独立に炭素数４〜２０の直鎖
状、分岐鎖状又は環状の構造を有するアルキル基を表
し、Ｒ’はそれぞれ独立に炭素数１〜４のアルキル基を
表す。）2. The thickening / gelling agent according to claim 1, which is a compound having an equatorial structure represented by the general formula (II). [Chemical 2] (However, in the formula, each R independently represents an alkyl group having a linear, branched, or cyclic structure having 4 to 20 carbon atoms, and R'independently represents an alkyl group having 1 to 4 carbon atoms. .)
３，５−トリス（ヘキシルアミノカルボニル）シクロヘ
キサン（化合物１）、式（ＩＶ）で表されるｃｉｓ−
１，３，５−トリス（ドデシルアミノカルボニル）シク
ロヘキサン（化合物２）、式（Ｖ）で表されるｃｉｓ−
１，３，５−トリス（オクタデシルアミノカルボニル）
シクロヘキサン（化合物３）、式（ＶＩ）で表されるｃ
ｉｓ−１，３，５−トリス（Ｎ−（３，７−ジメチルオ
クチル）アミノカルボニル）シクロヘキサン（化合物
４）の何れかである請求項２に記載の増粘・ゲル化剤。 【化３】 【化４】 【化５】 【化６】 3. cis-1, represented by the formula (III),
3,5-Tris (hexylaminocarbonyl) cyclohexane (Compound 1), cis-represented by the formula (IV)
1,3,5-Tris (dodecylaminocarbonyl) cyclohexane (Compound 2), cis-represented by the formula (V)
1,3,5-tris (octadecylaminocarbonyl)
Cyclohexane (compound 3), c represented by formula (VI)
The thickening / gelling agent according to claim 2, which is any one of is-1,3,5-tris (N- (3,7-dimethyloctyl) aminocarbonyl) cyclohexane (Compound 4). [Chemical 3] [Chemical 4] [Chemical 5] [Chemical 6]
れる化合物から選ばれる１種乃至は２種以上とを混合、
加温し、相溶させた後、冷却することを特徴とする流動
性有機物質の増粘・ゲル化方法。 【化７】 （但し、式中Ｒはそれぞれ独立に炭素数４〜２０の直鎖
状、分岐鎖状又は環状の構造を有するアルキル基を表
し、Ｒ’はそれぞれ独立に水素原子又は炭素数１〜４の
アルキル基を表す。）4. A mixture of a fluid organic substance and one or more selected from the compounds represented by formula (I),
A method for increasing the viscosity and gelation of a fluid organic substance, which comprises warming, compatibilizing, and then cooling. [Chemical 7] (However, in the formula, each R independently represents an alkyl group having a linear, branched, or cyclic structure having 4 to 20 carbon atoms, and R ′ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Represents a group.)
化する方法において、一般式（Ｉ）で表される化合物か
ら選ばれる１種乃至は２種以上を用いた流動性有機物質
の増粘・ゲル化を含むことを特徴とする流動性有機物質
含有組成物の安定化方法。 【化８】 （但し、式中Ｒはそれぞれ独立に炭素数４〜２０の直鎖
状、分岐鎖状又は環状の構造を有するアルキル基を表
し、Ｒ’はそれぞれ独立に水素原子又は炭素数１〜４の
アルキル基を表す。）5. A method for stabilizing a composition containing a flowable organic substance, which comprises using one or more compounds selected from the compounds represented by formula (I) to increase the flowable organic substance. A method for stabilizing a composition containing a flowable organic substance, which comprises viscous / gelling. [Chemical 8] (However, in the formula, each R independently represents an alkyl group having a linear, branched, or cyclic structure having 4 to 20 carbon atoms, and R ′ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Represents a group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34469197A JP3500289B2 (en) | 1997-01-29 | 1997-12-15 | Thickening and gelling agent composed of cyclohexanetricarboxamide derivative |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2979097 | 1997-01-29 | ||
| JP9-29790 | 1997-01-29 | ||
| JP34469197A JP3500289B2 (en) | 1997-01-29 | 1997-12-15 | Thickening and gelling agent composed of cyclohexanetricarboxamide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10273477A JPH10273477A (en) | 1998-10-13 |
| JP3500289B2 true JP3500289B2 (en) | 2004-02-23 |
Family
ID=26368026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34469197A Expired - Fee Related JP3500289B2 (en) | 1997-01-29 | 1997-12-15 | Thickening and gelling agent composed of cyclohexanetricarboxamide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3500289B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200002861A (en) * | 2017-04-28 | 2020-01-08 | 주식회사 다이셀 | Solvent Composition for Electronic Device Production |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6127450A (en) | 1998-06-09 | 2000-10-03 | Kerr Corporation | Dental restorative composite |
| US20030165743A1 (en) * | 1998-10-19 | 2003-09-04 | Tomonari Horikiri | Gel electrolyte, cell and electrochromic element |
| FR2798655B1 (en) * | 1999-09-21 | 2001-11-16 | Oreal | COMPOSITION COMPRISING A COMPOUND DERIVED FROM CYCLOHEXANE, COMPOUND AND USE OF SAID COMPOUND FOR STRUCTURING A COMPOSITION |
| AU2003235960A1 (en) | 2003-04-28 | 2004-11-23 | Ajinomoto Co., Inc. | Two-headed basic amino acid derivative |
| EP3144294B1 (en) * | 2014-05-12 | 2019-05-01 | Daicel Corporation | Thickening stabilizer and thickening stabilization composition using same |
| JP6423304B2 (en) * | 2015-03-30 | 2018-11-14 | トヨタ自動車株式会社 | Latent heat storage material |
| JP6401097B2 (en) * | 2015-03-30 | 2018-10-03 | トヨタ自動車株式会社 | Latent heat storage material |
-
1997
- 1997-12-15 JP JP34469197A patent/JP3500289B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ，Ｖｏｌ．３６， Ｎｏ．１８，ｐｐ．３２５５−３２５８，（１９９５） |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200002861A (en) * | 2017-04-28 | 2020-01-08 | 주식회사 다이셀 | Solvent Composition for Electronic Device Production |
| KR102560882B1 (en) * | 2017-04-28 | 2023-07-31 | 주식회사 다이셀 | Solvent composition for electronic device manufacturing |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10273477A (en) | 1998-10-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9464036B2 (en) | Thickening stabilizer, and thickening/stabilizing composition using the same | |
| JP6588338B2 (en) | Thickening stabilizer and thickening and stabilizing composition using the same | |
| JP6312669B2 (en) | Thickening stabilizer and thickening and stabilizing composition using the same | |
| JP3500289B2 (en) | Thickening and gelling agent composed of cyclohexanetricarboxamide derivative | |
| JP6620349B2 (en) | Thickening stabilizer and thickening and stabilizing composition using the same | |
| JPWO2018163989A1 (en) | Thickening stabilizer and thickening stabilized composition using the same | |
| CN109153634A (en) | N- alkyl diamide complexes compound and gel comprising it | |
| JPH10265761A (en) | Oil-gelating agent | |
| JP6464428B2 (en) | Thickening stabilizer and thickening and stabilizing composition using the same | |
| JP3620878B2 (en) | Gelling or solidifying agent for organic liquid | |
| JPS56103273A (en) | Novel regenerative material and regenerating device using it | |
| JP3501612B2 (en) | Composition containing cyclohexanetricarboxamide derivative | |
| JP7026355B2 (en) | Thickening stabilizer | |
| JP2003064346A (en) | Gelling agent for organic liquid and method of producing gelled product | |
| JP3254725B2 (en) | New organic gelling agents | |
| JP2799305B2 (en) | Fluorinated compound, method for producing the same and non-aqueous medium containing the same | |
| EP3144294B1 (en) | Thickening stabilizer and thickening stabilization composition using same | |
| JP2003064047A (en) | New cyclohexane derivative, organic gelling agent including the same and organogel | |
| WO2014061467A1 (en) | Liquid composition | |
| JP2020200289A (en) | Ester compound, gelling agent, and composition | |
| JP2023043952A (en) | Amide compound and thickener containing said amide compound | |
| JP2001270992A (en) | Disproportionated rosin composition and emulsifier | |
| WO2016080248A1 (en) | Thickening and stabilizing agent, and thickening and stabilizing composition using same | |
| JP2000053966A (en) | Liquid crystal composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |