JPH10273477A - Cyclohexanetricarboxamide derivative and thickening and gelling agent comprising the same - Google Patents
Cyclohexanetricarboxamide derivative and thickening and gelling agent comprising the sameInfo
- Publication number
- JPH10273477A JPH10273477A JP34469197A JP34469197A JPH10273477A JP H10273477 A JPH10273477 A JP H10273477A JP 34469197 A JP34469197 A JP 34469197A JP 34469197 A JP34469197 A JP 34469197A JP H10273477 A JPH10273477 A JP H10273477A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- thickening
- organic substance
- present
- gelling
- 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.)
- Granted
Links
- 230000008719 thickening Effects 0.000 title claims abstract description 42
- 239000002562 thickening agent Substances 0.000 title claims abstract description 13
- 239000003349 gelling agent Substances 0.000 title claims abstract description 12
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 239000012530 fluid Substances 0.000 claims abstract description 18
- 239000007983 Tris buffer Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 33
- 230000009969 flowable effect Effects 0.000 claims description 29
- 230000000087 stabilizing effect Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- AVZMBJURTSQXFM-UHFFFAOYSA-N N-(3,7-dimethyloctyl)cyclohexanecarboxamide Chemical compound CC(CCNC(=O)C1CCCCC1)CCCC(C)C AVZMBJURTSQXFM-UHFFFAOYSA-N 0.000 claims description 6
- 229940125904 compound 1 Drugs 0.000 claims description 6
- 229940125782 compound 2 Drugs 0.000 claims description 5
- 229940126214 compound 3 Drugs 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- CTMDFHFGBJYLTH-UHFFFAOYSA-N n-hexylcyclohexanecarboxamide Chemical compound CCCCCCNC(=O)C1CCCCC1 CTMDFHFGBJYLTH-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 125000004435 hydrogen atom Chemical group [H]* 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 16
- 239000000243 solution Substances 0.000 abstract description 7
- 238000001816 cooling Methods 0.000 abstract description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 4
- 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 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003973 alkyl amines Chemical class 0.000 abstract description 2
- 239000011368 organic material Substances 0.000 abstract 4
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000005259 measurement Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 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
- 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
- -1 Tris (N-laurylaminocarbonyl) cyclohexane Chemical compound 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- UOJWCKBTLPPNFI-UHFFFAOYSA-N n-octadecylcyclohexanecarboxamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C1CCCCC1 UOJWCKBTLPPNFI-UHFFFAOYSA-N 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
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZFEOFDFKIOBFFR-UHFFFAOYSA-N n-dodecylcyclohexanecarboxamide Chemical compound CCCCCCCCCCCCNC(=O)C1CCCCC1 ZFEOFDFKIOBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 241000894007 species Species 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
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization 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
- 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
- 239000002253 acid Substances 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 239000010775 animal oil Substances 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
- 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
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000463 material Substances 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
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-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
- 229960003504 silicones Drugs 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
- 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)
Abstract
Description
【０００１】[0001]
【発明が属する技術分野】本発明は、オイル等の流動性
有機物の増粘・ゲル化に好適な新規シクロヘキサンアル
キルアミド誘導体およびそれを用いた流動性有機物用の
増粘・ゲル化剤並びに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 novel cyclohexanealkylamide derivative suitable for thickening and gelling a fluid organic substance such as oil, a thickening / gelling agent for the fluid organic substance using the same, and a fluidity. The present invention relates to a method for thickening / gelling or stabilizing an organic substance or a composition containing the same.
【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。[0002] "Thickening / gelling" used in this specification
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 The method of thickening and gelling a liquid is a very important technology in the industry. For example, mayonnaise and salad dressing, which are metastable emulsions, are stable for a long time. This is because the thickener is added to stabilize the viscosity. Also, for example, in the event of a spill of heavy oil, etc. due to a tanker accident, if there is a technology to solidify the 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。[0004] Under such circumstances, various thickening / gelling agents have been developed. Examples of such successful products include, for example, alkyl acrylate copolymers and the like, all of which are water-based thickening / gelling agents, and the thickening / gelling agent for organic components is 12-hydroxystearin. Only the acid. However, since 12-hydroxystearic acid has no means for adjusting gelation, it could only induce the system to either solidify or remain liquid. That is, there has been a demand for a means for thickening and gelling an organic substance having fluidity or a composition containing the same.
【０００５】一方、後記一般式（Ｉ）に表される化合物
は文献未記載の新規化合物であって、これらの化合物が
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勿論知る由もない。On the other hand, the compounds represented by the following general formula (I) are novel compounds which have not been described in the literature, and these compounds exhibit excellent thickening and gelling effects on organic substances having fluidity. Of course you don't know.
【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。DISCLOSURE OF THE INVENTION The present invention has been made under such circumstances, and means for thickening or gelling or stabilizing an organic substance having fluidity 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 circumstances, the present inventors have developed an organic substance having fluidity or a substance capable of thickening, gelling or stabilizing a composition containing the same. As a result of intensive studies, the present inventors have found that the compounds represented by the following general formula (I) newly synthesized by the present inventors have the above properties, and completed the present invention.
【０００８】すなわち、本発明は、下記一般式（Ｉ）に
表される化合物である。That is, the present invention is a compound represented by the following general formula (I).
【０００９】[0009]
【化７】 Embedded image
【００１０】（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。）(Wherein R is each independently 4 carbon atoms)
-20 represents an alkyl group having a linear, branched or cyclic structure, and R 'each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. )
【００１１】本発明に係る一般式（Ｉ）に表される化合
物として、具体的には、一般式（ＩＩ）に表されるエク
ァトリアル型構造を有する化合物が挙げられる。The compound represented by the general formula (I) according to the present invention specifically includes a compound having an equatorial structure represented by the general formula (II).
【００１２】[0012]
【化８】 Embedded image
【００１３】（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。）(Wherein R is each independently 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. )
【００１４】さらに、一般式（ＩＩ）に表されるエクァ
トリアル型構造を有する化合物として、具体的には、式
（ＩＩＩ）に表される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）に表される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）に表される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）に表される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 an equatorial structure represented by the general formula (II), specifically, cis-1,3,5-tris (hexylaminocarbonyl) cyclohexane represented by the formula (III) (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-1,3,3 represented by the formula (VI)
5-tris (N- (3,7-dimethyloctyl) aminocarbonyl) cyclohexane (compound 4) and the like.
【００１５】[0015]
【化９】 Embedded image
【００１６】[0016]
【化１０】 Embedded image
【００１７】[0017]
【化１１】 Embedded image
【００１８】[0018]
【化１２】 Embedded image
【００１９】また、本発明は、上記本発明の化合物から
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
本発明の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。The present invention also provides a thickening / gelling agent for a flowable organic substance comprising at least one compound selected from the compounds of the present invention, or a flowable organic substance, A method for thickening and gelling a flowable organic substance, which comprises mixing, heating, compatibilizing, and cooling one or more kinds selected from the compounds described above.
【００２０】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、上記本発明の化
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。Further, the present invention provides a method for stabilizing a composition containing a flowable organic substance, wherein the method comprises the step of thickening the flowable organic substance using one or more compounds selected from the compounds of the present invention. -It is intended to provide a method for stabilizing a composition containing a flowable organic substance, which is characterized by including gelation.
【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、本発明の化合物について説明する。 （１）本発明の化合物 本発明の化合物は、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 of the present invention will be described. (1) Compound of the Present Invention The compound of the present invention is an alkyl derivative of cyclohexanetricarboxamide, and has a chemical formula as shown in the above general formula (I).
【００２２】本発明の化合物に於いては、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）に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。本発明の化合物においては、
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 compounds of the present invention, stereoisomers exist depending on the manner in which three alkylaminocarbonyl groups are bonded to the six-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 an equatorial structure represented by the above general formula (II) in which all three alkylaminocarbonyl groups are equatorial bonds. Compounds are more preferred. In the compound of the present invention,
This is because such a compound in which an alkylaminocarbonyl group takes an equatorial bond has a more excellent thickening / gelling effect on a fluid organic substance.
【００２３】本発明の化合物のうち、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（ＩＩＩ）に
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）
に表される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）
に表される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）に表される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）に表され
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）に表される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）等を挙げることができる。Among the compounds of the present invention, compounds in which at least two alkylaminocarbonyl groups are equatorial bonds are specifically exemplified by cis-1,3,5-tris represented by the above formula (III). (Hexylaminocarbonyl) cyclohexane (compound 1), formula (IV)
Cis-1,3,5-tris (dodecylaminocarbonyl) cyclohexane (compound 2) represented by the formula (V)
Cis-1,3,5-tris (octadecylaminocarbonyl) cyclohexane (compound 3) represented by the formula: cis-1,3,5-tris (N-
(3,7-dimethyloctyl) aminocarbonyl) cyclohexane (compound 4) and trans-1,3,5-trimethyl-1,3,5- represented by the following formula (VII)
Tris (N-laurylaminocarbonyl) cyclohexane (compound 5), trans represented by formula (VIII)
-1,3,5-trimethyl-1,3,5-tris (N-
Stearylaminocarbonyl) cyclohexane (compound 6).
【００２４】また、これらの内では上記一般式（ＩＩ）
に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-mentioned general formula (II)
Compounds 1 to 4 which are compounds having an equatorial structure shown in (1) and (2) are particularly preferable because of the above-mentioned thickening / gelling action.
【００２５】[0025]
【化１３】 Embedded image
【００２６】[0026]
【化１４】 Embedded image
【００２７】本発明の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 are, for example,
It may be manufactured by the following method. That is, 1,3,5-cyclohexanetricarboxylic acid having steric properties corresponding to the target compound is converted to acid chloride with thionyl chloride,
An alkylamine corresponding to the target compound may be reacted therewith. The product thus obtained can be purified by ordinary purification means such as recrystallization and column chromatography.
【００２８】かくして得られる本発明の化合物は何れも
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。The compounds of the present invention thus obtained are all excellent in the action of thickening, gelling or stabilizing an organic substance having fluidity 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
発明の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の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) The thickening / gelling agent for a flowable organic substance of the present invention and the method of thickening / gelling the flowable organic substance are as described above. One or more selected from the compounds of the present invention.
The thickening / gelling agent of the present invention may further contain optional components such as a base, if necessary. The compound of the present invention may be prepared by mixing such optional components with the compound of the present invention. Can be formulated 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、上記本発明の化合物から選ば
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。In the method for thickening and gelling a flowable organic substance according to the present invention, the flowable organic substance is mixed with one or more kinds selected from the above-mentioned compounds of the present invention, heated, and made compatible. And then cooling.
【００３１】本発明の流動性有機物質の増粘・ゲル化方
法における、上記本発明の化合物の使用量としては、用
いる本発明の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、本発明の化合物は唯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 of the present invention to be used in the method for thickening and gelling the flowable organic substance of the present invention depends on the compound of the present invention to be used and the kind of the target flowable organic substance. 0.1 to 100 parts by weight, more preferably 0.5 to 100 parts by weight of the fluid organic substance.
The range is from 90 to 90 parts by weight, more preferably from 1 to 80 parts by weight. In this case, the compound of the present invention is only 1
Only the species may be used, or two or more species may be used.
【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
の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, the above-mentioned thickening / gelling agent of the present invention may be used. The amount of the compound of the present invention may be adjusted so as to be 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
本発明の化合物の使用量は、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 for thickening and gelling a flowable organic substance of the present invention, it is possible to further thicken and gel a composition containing a flowable organic substance. In this case, the amount of the compound of the present invention to be used may be in the above range as an amount based on 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の化
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、用いる本発明の化
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 and gelling the flowable organic substance of the present invention, the flowable organic substance and the compound of the present invention are mixed in the above ratio, and then heated to make them compatible. The temperature at the time of heating is not particularly limited as long as they are compatible with each other, but preferably does not exceed 100 ° C.
When the boiling point of the fluid organic substance is 100 ° C. or lower, the boiling point is preferably about the same. Further, this temperature can be appropriately selected depending on the type of the compound of 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 carried out after the above-mentioned compatibility, but this cooling is not particularly limited either. It may be cooled.
【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 the fluid organic substance to which the thickening / gelling method is applied include, for example, organic solvents such as carbon tetrachloride, tetrahydrofuran, hexane, cyclohexane, benzene, toluene, chlorobenzene, pyridine, kerosene, gasoline, light oil, Fuels such as heavy oil, animal and vegetable oils such as olive oil, soybean oil, corn oil, castor oil, tallow, jojoba oil, mineral oils such as squalane and liquid paraffin, silicones such as dimethylpolysiloxane and methylphenylpolysiloxane, octyl oleate Synthetic esters such as dodecyl, glyceryl triisooctanoate and neopentyl glycol diisooctate can be exemplified. The invention can also be applied to mixtures of these mobile 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
記本発明の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 the composition containing a flowable organic substance of the present invention The method for stabilizing the composition containing a flowable organic substance of the present invention may be one or two or more selected from the compounds of the present invention. The present invention is characterized by including a thickening and gelling of a fluid organic substance using the above.
【００３８】本発明の安定化方法における、上記本発明
の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。The thickening and gelling of a flowable organic substance using the compound of the present invention in the stabilization method of the present invention has been described in the method of thickening and gelling a flowable organic substance of the present invention. It is on the street.
【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
明の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、予め上記本発明の化合物の適当量を
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, an appropriate amount of the above-mentioned compound of the present invention is mixed with a composition containing a flowable organic substance, heated and made compatible. , A method of cooling, a flowable organic substance which is a raw material of the composition containing a flowable organic substance, an appropriate amount of the compound of the present invention is added and mixed in advance, heated, made compatible, and then cooled, Examples of the method include a method of producing a thickened and gelled product of the fluid organic substance and blending the same into a composition.
【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 flowable organic substance, and specific examples include cosmetics, paints, foods, and pharmaceuticals. 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, and the mixture was stirred at room temperature for 1 hour, and the reaction solution was concentrated. To this, 3 g of hexylamine dissolved in 50 ml of methylene chloride and 10 ml of triethylamine was added and added.
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. Its descriptive values such as elemental analysis, IR, and NMR 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, and the mixture was stirred at room temperature for 1 hour, and the reaction solution was concentrated. To this, laurylamine (6 g) dissolved in 50 ml of methylene chloride and 10 ml of triethylamine was added 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. Its descriptive values such as elemental analysis, IR, and NMR 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, and the mixture was stirred at room temperature for 1 hour, and the reaction solution was concentrated. To this was added 7 g of stearylamine dissolved in 50 ml of methylene chloride and 10 ml of triethylamine.
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
Indicative values such as supported 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, and the mixture was stirred at room temperature for 1 hour, and the reaction solution was concentrated. 5 g of 3,7-dimethyloctylamine was added to 5
After dissolving in 0 ml of methylene chloride and 10 ml of triethylamine, the mixture was heated and stirred for 2 hours. The precipitated crystals were collected and washed with water to obtain 6 g of Compound 4. Elemental analysis of this thing,
Indices such as IR and NMR 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 liquid organic substances shown in Table 1 were weighed by 1 cm 3 into a test tube, and the weighed compound 1 obtained in the above Example 1 was added thereto and mixed. Then, the mixture was heated and stirred at an appropriate temperature for each fluid organic substance (boiling point for a fluid organic substance having a boiling point of less than 100 ° C., otherwise 100 ° C.) until it was compatible.
The compatible material was cooled to 25 ° C., and it was visually determined whether or not it had gelled. When the gel was formed, the addition amount of the compound 1 was reduced, and when the gel was not formed, the addition amount was increased, and the minimum amount (mg) for gelation was determined. In addition, with respect to the compounds 2 to 4 obtained in the above Examples 2 to 4, the minimum amount (mg) for gelling various fluid organic substances was similarly obtained. Table 1 shows the results. In addition, the description of "gel-like" in the table means that no gel was formed, 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
明の化合物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, it can be seen that all of the compounds 1 to 4 of the present invention obtained in the above Examples are excellent in the action of thickening and gelling the flowable organic substance.
【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 solution was concentrated. 6 g of laurylamine were added to 50 ml of methylene chloride and 1 g of laurylamine.
After dissolving in 0 ml of triethylamine, the mixture was heated and stirred for 2 hours. The precipitated crystals were collected and washed with water.
5 g were obtained. Its descriptive value by elemental analysis, NMR and the like supported the structure.
【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 solution was concentrated. 7 g of stearylamine was dissolved in 50 ml of methylene chloride and 10 ml of triethylamine, and the mixture was heated and stirred for 2 hours. The precipitated crystals were collected and washed with water.
1 g was obtained. Its descriptive value by elemental analysis, NMR and the like supported the structure.
【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）に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。According to the present invention, by using a newly produced compound represented by the general formula (I), an organic substance having fluidity or a composition containing the same is thickened and gelled. 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 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Hiroyoshi Shirai 3-15-1, Tsuneta, Ueda-shi, Nagano Prefecture Shinshu University, Faculty of Textile Sciences (72) Inventor Koichi Iyanagi 560 Paula Kashio-cho, Totsuka-ku, Yokohama-shi, Kanagawa Chemical Industry Co., Ltd.
Claims (6)
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 compound represented by the general formula (I). Embedded image (Where R represents an alkyl group having a linear, branched or cyclic structure having 4 to 20 carbon atoms each independently, and R ′ 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記載の化合物。 【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 compound according to claim 1, which is a compound having an equatorial structure represented by the general formula (II). Embedded image (Wherein, R in the formula each 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）に表される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）に表される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）に表される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記載の化合物。 【化３】 【化４】 【化５】 【化６】 3. The cis-1,
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 the formula (VI)
The compound according to claim 2, which is any of is-1,3,5-tris (N- (3,7-dimethyloctyl) aminocarbonyl) cyclohexane (compound 4). Embedded image Embedded image Embedded image Embedded image
物から選ばれる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。4. A thickening / gelling agent for a flowable organic substance comprising one or more selected from the compounds according to claim 1. Description:
か一項に記載の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。5. A fluid organic substance and one or more compounds selected from the compounds according to any one of claims 1 to 3, which are mixed, heated, made compatible, and then cooled. A method for thickening and gelling a flowable organic substance.
化する方法において、請求項１〜３の何れか一項に記載
の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。6. A method for stabilizing a composition containing a flowable organic substance, wherein one or more compounds selected from the compounds according to claim 1 are used. A method for stabilizing a composition containing a flowable organic substance, comprising thickening and gelling the organic substance.
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|---|---|---|---|
| JP34469197A JP3500289B2 (en) | 1997-01-29 | 1997-12-15 | Thickening and gelling agent composed of cyclohexanetricarboxamide derivative |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9-29790 | 1997-01-29 | ||
| JP2979097 | 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 true JPH10273477A (en) | 1998-10-13 |
| JP3500289B2 JP3500289B2 (en) | 2004-02-23 |
Family
ID=26368026
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| 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 |
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| Country | Link |
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| FR2798655A1 (en) * | 1999-09-21 | 2001-03-23 | Oreal | COMPOSITION COMPRISING A COMPOUND DERIVED FROM CYCLOHEXANE, COMPOUND AND USE OF SAID COMPOUND FOR STRUCTURING A COMPOSITION |
| US6395803B1 (en) | 1998-06-09 | 2002-05-28 | Kerr Corporation | Dental restorative composite |
| EP0996029A3 (en) * | 1998-10-19 | 2002-07-31 | Canon Kabushiki Kaisha | Gel electrolyte, cell and electrochromic element |
| US6921747B2 (en) | 2003-04-28 | 2005-07-26 | Ajinomoto Co., Inc. | Basic amino acid derivatives |
| WO2015174300A1 (en) * | 2014-05-12 | 2015-11-19 | 株式会社ダイセル | Thickening stabilizer and thickening stabilization composition using same |
| JP2016190894A (en) * | 2015-03-30 | 2016-11-10 | トヨタ自動車株式会社 | Latent heat storage material |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6395803B1 (en) | 1998-06-09 | 2002-05-28 | Kerr Corporation | Dental restorative composite |
| EP0996029A3 (en) * | 1998-10-19 | 2002-07-31 | Canon Kabushiki Kaisha | Gel electrolyte, cell and electrochromic element |
| FR2798655A1 (en) * | 1999-09-21 | 2001-03-23 | Oreal | COMPOSITION COMPRISING A COMPOUND DERIVED FROM CYCLOHEXANE, COMPOUND AND USE OF SAID COMPOUND FOR STRUCTURING A COMPOSITION |
| EP1086945A1 (en) * | 1999-09-21 | 2001-03-28 | L'oreal | Composition containing a cyclohexane derivative, compound and use thereof for structuring the composition |
| JP2001114630A (en) * | 1999-09-21 | 2001-04-24 | L'oreal Sa | Composition containing a cyclohexane-based compound, the compound and use of the compound for structuring the composition |
| US7288262B1 (en) * | 1999-09-21 | 2007-10-30 | L'oreal S.A. | Composition comprising a cyclohexane-based compound, compound and use of said compound to structure a composition |
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| US11655381B2 (en) * | 2017-04-28 | 2023-05-23 | Daicel Corporation | Solvent composition for electronic device production |
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