JPH08231942A - Gelling or solidifying agent for organic liquid - Google Patents
Gelling or solidifying agent for organic liquidInfo
- Publication number
- JPH08231942A JPH08231942A JP6215395A JP6215395A JPH08231942A JP H08231942 A JPH08231942 A JP H08231942A JP 6215395 A JP6215395 A JP 6215395A JP 6215395 A JP6215395 A JP 6215395A JP H08231942 A JPH08231942 A JP H08231942A
- Authority
- JP
- Japan
- Prior art keywords
- solidifying agent
- diaminocyclohexane
- gelling
- group
- organic liquid
- 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.)
- Pending
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 21
- -1 alkyl isocyanate Chemical class 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012948 isocyanate Substances 0.000 claims abstract description 7
- 239000003921 oil Substances 0.000 claims abstract description 7
- 235000019198 oils Nutrition 0.000 claims abstract description 7
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 241001465754 Metazoa Species 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 239000010775 animal oil Substances 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 5
- 229920005862 polyol Polymers 0.000 claims abstract description 5
- 150000003077 polyols Chemical class 0.000 claims abstract description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 5
- 239000008158 vegetable oil Substances 0.000 claims abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000001816 cooling Methods 0.000 abstract description 5
- 230000007774 longterm Effects 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 238000004321 preservation Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000499 gel Substances 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000003349 gelling agent Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- FMZUHGYZWYNSOA-VVBFYGJXSA-N (1r)-1-[(4r,4ar,8as)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical compound C([C@@H]1OC(O[C@@H]([C@@H]1O1)[C@H](O)CO)C=2C=CC=CC=2)OC1C1=CC=CC=C1 FMZUHGYZWYNSOA-VVBFYGJXSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 238000005555 metalworking Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- BGRXBNZMPMGLQI-UHFFFAOYSA-N 2-octyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC BGRXBNZMPMGLQI-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 229940087101 dibenzylidene sorbitol Drugs 0.000 description 1
- 238000004821 distillation Methods 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
- 229920001971 elastomer Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000001879 gelation Methods 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
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Lubricants (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は有機液体のゲル化または
固化剤に係わり、塗料、インク、潤滑油、農業、水産、
化粧品や医薬品、繊維、樹脂、高分子、ゴム、金属等の
加工分野等において利用できる。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a gelling or solidifying agent for organic liquids such as paints, inks, lubricating oils, agriculture, fisheries,
It can be used in the fields of processing cosmetics, pharmaceuticals, fibers, resins, polymers, rubbers, metals, etc.
【０００２】[0002]
【従来の技術】一般に前記産業分野において使用される
有機液体類（動植物油脂、エステル、ポリオール、エー
テル、アルコール、炭化水素等）をゲル化または固化す
る機能を有するものとして、１２−ヒドロキシステアリ
ン酸、ジベンジリデンソルビトール、脂肪酸のアルカリ
金属塩およびアルカリ土類金属塩、アミノ酸誘導体（例
えば、Ｎ−アシルグルタミン酸誘導体）等が知られてい
る。2. Description of the Related Art Generally, 12-hydroxystearic acid, which has a function of gelling or solidifying organic liquids (animal and vegetable oils, esters, polyols, ethers, alcohols, hydrocarbons, etc.) used in the above industrial fields, Dibenzylidene sorbitol, fatty acid alkali metal salts and alkaline earth metal salts, amino acid derivatives (for example, N-acyl glutamic acid derivatives) and the like are known.
【０００３】この中で、１２−ヒドロキシステアリン酸
は安価であるが、ゲル化または固化できる有機液体の種
類が少なく、得られたゲルが軟化する温度も低い。一
方、ジベンジリデンソルビトールは少量の添加で強いゲ
ルを形成するものの、ベンズアルデヒドを遊離するとい
う難点をもち、また、高融点であるため低沸点の短鎖ア
ルコール類等を固形化するには不適当である。脂肪酸の
アルカリ金属塩・アルカリ土類金属塩は、ゲル化または
固化のための添加量を多く必要とし、使用可能な条件も
限られる等の制約がある。また、Ｎ−アシルグルタミン
酸誘導体等のアミノ酸誘導体は、製造方法が複雑であ
り、基本骨格もアミノ酸に限定されているため、化粧品
分野などに利用する場合には、アミノ酸に由来する皮膚
への刺激性の懸念も依然としてある。Of these, 12-hydroxystearic acid is inexpensive, but there are few kinds of organic liquids that can be gelled or solidified, and the temperature at which the obtained gel softens is low. On the other hand, although dibenzylidene sorbitol forms a strong gel with a small amount of addition, it has the drawback of releasing benzaldehyde, and its high melting point makes it unsuitable for solidifying short-chain alcohols with low boiling points. is there. Alkali metal salts / alkaline earth metal salts of fatty acids require a large amount to be added for gelation or solidification, and there are restrictions such as usable conditions. In addition, since amino acid derivatives such as N-acyl glutamic acid derivatives are complicated in the manufacturing method and the basic skeleton is limited to amino acids, they are irritating to the skin derived from amino acids when used in the field of cosmetics. There are still concerns.
【０００４】[0004]
【発明が解決しようとする課題】このように、これまで
提案されているゲル化または固化剤は、前記いずれかの
点で充分に満足できる機能を有するものではなかった。
本発明の目的は、容易に製造することが可能であり、種
々の有機液体を少量の添加でゲル化または固化でき、均
一で、かつ長期間の保存および温度変化に対して安定性
が高いゲル化物または固化物となすことができる、有機
液体のゲル化または固化剤を提供することにある。As described above, the gelling or solidifying agents proposed so far do not have a sufficiently satisfactory function in any of the above points.
The object of the present invention is a gel that can be easily produced, can gel or solidify various organic liquids with a small amount of addition, is uniform, and has high stability against long-term storage and temperature change. An object of the present invention is to provide a gelling or solidifying agent for an organic liquid, which can be a solidified or solidified product.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、前記目的
を達成するために鋭意検討を重ねた結果、特定のジアル
キルウレア誘導体を用いることにより種々の有機液体に
対して優れたゲル状固形化物が得られることを見出し、
本発明を完成するに至った。すなわち本発明は、ジアミ
ノシクロヘキサンと、炭素数が２〜１８で飽和の直鎖状
および／または分岐状アルキル基を有するアルキルイソ
シアネートとを反応させて得られる、下記一般式（Ｉ）Means for Solving the Problems The inventors of the present invention have conducted extensive studies to achieve the above-mentioned object, and as a result, by using a specific dialkylurea derivative, an excellent gel-like solid for various organic liquids has been obtained. Found that a compound can be obtained,
The present invention has been completed. That is, the present invention is obtained by reacting diaminocyclohexane with an alkylisocyanate having a saturated linear and / or branched alkyl group having 2 to 18 carbon atoms, represented by the following general formula (I)
【化２】 （式（Ｉ）中、Ｒは炭素数２〜１８の飽和直鎖状および
／または飽和分岐状アルキル基を表わす。）で示される
ジアルキルウレア誘導体を有効成分とする有機液体のゲ
ル化または固化剤である。Embedded image (In the formula (I), R represents a saturated linear and / or saturated branched alkyl group having 2 to 18 carbon atoms.) A gelling or solidifying agent of an organic liquid containing a dialkylurea derivative as an active ingredient. Is.
【０００６】本発明のジアルキルウレア誘導体を製造す
るための原料成分としては、ジアミノシクロヘキサンお
よびアルキルイソシアネートを用いる。ジアミノシクロ
ヘキサンは、具体的には、１，２−ジアミノシクロヘキ
サン、１，３−ジアミノシクロヘキサンおよび１，４−
ジアミノシクロヘキサンをあげることができ、このうち
特に好ましいのは、１，２−ジアミノシクロヘキサンで
ある。なおこれらのジアミノシクロヘキサンは単独で使
用してもよく、あるいは２種以上を混合して用いてもよ
い。Diaminocyclohexane and alkylisocyanate are used as raw material components for producing the dialkylurea derivative of the present invention. Diaminocyclohexane is specifically 1,2-diaminocyclohexane, 1,3-diaminocyclohexane and 1,4-
Diaminocyclohexane can be mentioned, of which 1,2-diaminocyclohexane is particularly preferred. These diaminocyclohexanes may be used alone or in combination of two or more.
【０００７】また、もう一方の原料であるアルキルイソ
シアネートは、炭素数が２〜１８で、飽和の、直鎖状お
よび／または分岐状アルキル基を有するものが使用可能
である。具体的に直鎖状アルキル基として、エチル基、
プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプ
チル基、オクチル基、ノニル基、デシル基、ウンデシル
基、ドデシル基、トリデシル基、テトラデシル基、ペン
タデシル基、ヘキサデシル基、ヘプタデシル基、オクタ
デシル基を例としてあげることができる。また分岐状ア
ルキル基として２−エチルブチル基、２−エチルヘキシ
ル基、２，４，４−トリメチルペンチル基、３，５，５
−トリメチルヘキシル基、３，７−ジメチルオクチル
基、６−プロピルノニル基、１２−メチルトリデシル
基、２−メチルテトラデシル基、５−メチルテトラデシ
ル基、２，２−ジメチルテトラデシル基、２−ヘキシル
デシル基、２−ヘプチルウンデシル基等を例示できる。
これらの直鎖状アルキル基または分岐状アルキル基をも
つアルキルイソシアネートは単独で使用してもよく、あ
るいは２種以上を混合して用いてもよい。As the other raw material, an alkyl isocyanate having 2 to 18 carbon atoms and having a saturated, straight-chain and / or branched alkyl group can be used. Specifically, as a linear alkyl group, an ethyl group,
Examples include propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group. I can give you. Further, as a branched alkyl group, 2-ethylbutyl group, 2-ethylhexyl group, 2,4,4-trimethylpentyl group, 3,5,5
-Trimethylhexyl group, 3,7-dimethyloctyl group, 6-propylnonyl group, 12-methyltridecyl group, 2-methyltetradecyl group, 5-methyltetradecyl group, 2,2-dimethyltetradecyl group, 2 Examples thereof include a hexyldecyl group and a 2-heptylundecyl group.
These alkyl isocyanates having a linear alkyl group or a branched alkyl group may be used alone or in combination of two or more.
【０００８】本発明のジアルキルウレア誘導体は、前記
のジアミノシクロヘキサンと、飽和の直鎖状および／ま
たは分岐状アルキル基を有するアルキルイソシアネート
の１種または２種以上とを原料とし、従来公知の方法を
用いて容易に合成することができる。その方法や条件は
特に限定されないが、例えば両原料の所定の反応当量
を、不活性な無水有機溶媒中で、室温ないし氷冷下にて
１〜５時間攪拌し、付加反応せしめればよい。本発明に
おいて使用するアルキルウレア誘導体は、好ましくはジ
アルキルウレア誘導体あるいはジアルキルウレア誘導体
とモノアルキルウレア誘導体との混合物であり、最も好
ましくはジアルキルウレア誘導体である。The dialkylurea derivative of the present invention comprises the above-mentioned diaminocyclohexane and one or more alkyl isocyanates having a saturated linear and / or branched alkyl group as a raw material, and a conventionally known method is used. Can be used and easily synthesized. Although the method and conditions are not particularly limited, for example, predetermined reaction equivalents of both raw materials may be stirred in an inert anhydrous organic solvent at room temperature or under ice cooling for 1 to 5 hours to carry out an addition reaction. The alkylurea derivative used in the present invention is preferably a dialkylurea derivative or a mixture of a dialkylurea derivative and a monoalkylurea derivative, and most preferably a dialkylurea derivative.
【０００９】なお、反応物中に未反応の原料が残存する
場合には減圧留去、溶剤分別等の公知手段で除去してお
くことが望ましいが、若干（数重量％未満）の未反応の
ジアミノシクロヘキサンおよび／またはアルキルイソシ
アネートの混在については特にさしつかえない。反応物
の精製は、減圧下での未反応物等の除去、アセトン等の
多量の有機溶媒による再結晶、活性白土、活性炭、シリ
カゲル、アルミナ等の吸着剤処理、その他による精製法
が可能であり、必要に応じてこれらを単独でもしくは組
み合わせて適用すればよい。When unreacted raw materials remain in the reaction product, it is desirable to remove them by a known means such as distillation under reduced pressure or solvent fractionation, but some (less than several wt%) of unreacted raw materials are removed. There is no particular limitation on the mixture of diaminocyclohexane and / or alkyl isocyanate. The reaction product can be purified by removing unreacted substances under reduced pressure, recrystallization with a large amount of an organic solvent such as acetone, adsorbent treatment with activated clay, activated carbon, silica gel, alumina, etc. If necessary, these may be applied alone or in combination.
【００１０】本発明では、こうして得られるジアルキル
ウレア誘導体を各種有機液体のゲル化または固化剤とす
ることができ、そのゲル化物または固化物を塗料、イン
ク、潤滑油、化粧品、医薬品、農業分野の基剤もしくは
製剤とすることができる。ここで有機液体としては、大
豆油、菜種油、コーン油、サフラワー油、ヒマワリ油、
綿実油、オリーブ油、パーム油、ヒマシ油、魚油、豚
脂、牛脂等の動植物油脂類、ミリスチン酸イソプロピ
ル、トリ−２−エチルヘキサン酸グリセリド、ミリスチ
ン酸２−オクチルドデシル等のエステル類、ポリエチレ
ングリコール、ポリプロピレングリコール、ポリグリセ
リン等のポリオール類、エチルセロソルブ、ブチルセロ
ソルブ等のエーテル類、メタノール、エタノール等のア
ルコール類、灯油、重油、流動パラフィン、イソパラフ
ィン等の炭化水素系油剤、また、キシレン、トルエン等
の有機溶剤や廃食用油、廃潤滑油、廃金属加工油剤等の
いわゆる廃油類を対象とすることができる。In the present invention, the dialkylurea derivative thus obtained can be used as a gelling or solidifying agent for various organic liquids, and the gelled or solidified product can be used in paints, inks, lubricating oils, cosmetics, pharmaceuticals and agricultural fields. It can be a base or a preparation. Here, as the organic liquid, soybean oil, rapeseed oil, corn oil, safflower oil, sunflower oil,
Animal and vegetable oils such as cottonseed oil, olive oil, palm oil, castor oil, fish oil, lard, beef tallow, isopropyl myristate, tri-2-ethylhexanoate glyceride, esters such as 2-octyldodecyl myristate, polyethylene glycol, polypropylene Polyols such as glycol and polyglycerin, ethers such as ethyl cellosolve and butyl cellosolve, alcohols such as methanol and ethanol, hydrocarbon oils such as kerosene, heavy oil, liquid paraffin and isoparaffin, and organic solvents such as xylene and toluene. So-called waste oils such as waste edible oil, waste lubricating oil, waste metal working oil, etc. can be targeted.
【００１１】本発明のゲル化または固化剤を前記有機液
体１mlに対し、１〜５０mg、好ましくは２〜２０mg添加
し、所望により６０〜１２０℃程度に加熱して均一状態
になるまで攪拌した後、常温にて静置すれば、ゲル化物
または固化物を調製することができる。このものは均一
なゲル化物または固化物であり、常温で液体部分を生じ
ることなく、また、長期間の保存においても液体部分の
発生はない。なお本発明のゲル化または固化剤は単独で
も使用できるが、本発明の目的を逸脱しないかぎり、従
来公知のゲル化剤、天然ワックスまたは合成ワックス等
の固化剤等を適量併用してもよい。The gelling or solidifying agent of the present invention is added to 1 ml of the above-mentioned organic liquid in an amount of 1 to 50 mg, preferably 2 to 20 mg, and optionally heated to about 60 to 120 ° C. and stirred until a uniform state is obtained. If it is allowed to stand at room temperature, a gelled product or a solidified product can be prepared. This is a uniform gelated product or solidified product, does not generate a liquid part at room temperature, and does not generate a liquid part even during long-term storage. The gelling or solidifying agent of the present invention can be used alone, but a conventionally known gelling agent, a solidifying agent such as a natural wax or a synthetic wax, and the like may be used in an appropriate amount unless the object of the present invention is deviated.
【００１２】[0012]
【実施例】以下の合成例および実施例において、％は重
量基準である。 合成例１ 攪拌機、温度計、窒素ガス吹込管及び水分離器を取付け
た四ツ口フラスコ中で、１，２−ジアミノシクロヘキサ
ン（東京化成（株）製、試薬）２．２８ｇ（０．０２モ
ル）を４０mlの脱水テトラヒドロフランに溶かし、氷冷
下でドデシルイソシアネート（東京化成（株）製、試
薬）８．４５ｇ（０．０４モル）を滴下した。室温で２
時間攪拌した後、４０mlの脱水テトラヒドロフランを追
加して一旦６０℃に加熱し、続いて室温まで放冷した。
このとき生成したゲルを５０mlのアセトンを加えてよく
砕き、不溶物を吸引濾取し、アセトンでよく洗って、室
温で乾燥した。７．７０ｇの白色固体物（試料記号Ａ）
を得た。このものはジアルキルウレア誘導体：９８重量
％およびモノアルキルウレア誘導体：２重量％からなっ
ていた。EXAMPLES In the following synthesis examples and examples,% is based on weight. Synthesis Example 1 In a four-necked flask equipped with a stirrer, a thermometer, a nitrogen gas blowing tube and a water separator, 1,2-diaminocyclohexane (manufactured by Tokyo Kasei Co., Ltd., reagent) 2.28 g (0.02 mol) ) Was dissolved in 40 ml of dehydrated tetrahydrofuran, and 8.45 g (0.04 mol) of dodecyl isocyanate (reagent, manufactured by Tokyo Kasei Co., Ltd.) was added dropwise under ice cooling. 2 at room temperature
After stirring for an hour, 40 ml of dehydrated tetrahydrofuran was added, the mixture was once heated to 60 ° C., and then allowed to cool to room temperature.
The gel produced at this time was crushed well by adding 50 ml of acetone, the insoluble matter was filtered off with suction, washed well with acetone, and dried at room temperature. 7.70 g of white solid (Sample code A)
I got This was composed of 98% by weight of dialkylurea derivative and 2% by weight of monoalkylurea derivative.
【００１３】合成例２ 攪拌機、温度計、窒素ガス吹込管及び水分離器を取付け
た四ツ口フラスコ中で、１，３−ジアミノシクロヘキサ
ン（東京化成（株）製、試薬）２．２８ｇ（０．０２モ
ル）を４０mlの脱水テトラヒドロフランに溶かし、氷冷
下でドデシルイソシアネート（合成例１と同じ）８．４
５ｇ（０．０４モル）を滴下した。室温で２時間攪拌し
た後、４０mlの脱水テトラヒドロフランを追加して一旦
６０℃に加熱し、続いて室温まで放冷した。このとき生
成したゲルを５０mlのアセトンを加えてよく砕き、不溶
物を吸引濾取し、アセトンでよく洗って室温で乾燥し
た。７．７０ｇの白色固体物（試料記号Ｂ）を得た。こ
のものはジアルキルウレア誘導体：９９重量％およびモ
ノアルキルウレア誘導体：１重量％からなっていた。Synthesis Example 2 2.28 g (0,0) of 1,3-diaminocyclohexane (manufactured by Tokyo Kasei Co., Ltd.) in a four-necked flask equipped with a stirrer, a thermometer, a nitrogen gas blowing tube and a water separator. 0.02 mol) was dissolved in 40 ml of dehydrated tetrahydrofuran and, under ice cooling, dodecyl isocyanate (the same as in Synthesis Example 1) 8.4.
5 g (0.04 mol) was added dropwise. After stirring at room temperature for 2 hours, 40 ml of dehydrated tetrahydrofuran was added, the mixture was once heated to 60 ° C., and then allowed to cool to room temperature. The gel produced at this time was crushed well by adding 50 ml of acetone, the insoluble matter was filtered off with suction, washed well with acetone and dried at room temperature. 7.70 g of a white solid (Sample Code B) was obtained. It consisted of 99% by weight of dialkylurea derivative and 1% by weight of monoalkylurea derivative.
【００１４】合成例３ １，２−ジアミノシクロヘキサンと種々のアルキルイソ
シアネートとを用いて、合成例１に記載の方法に準じ
て、本発明に係るジアルキルウレア誘導体（試料記号Ｃ
〜Ｇ）、ジアルキルウレア誘導体／モノアルキルウレア
誘導体＝２／１（重量比）の混合物（試料記号Ｈ）を合
成した。Synthetic Example 3 A dialkylurea derivative according to the present invention (sample symbol C) was prepared by using 1,2-diaminocyclohexane and various alkyl isocyanates according to the method described in Synthetic Example 1.
To G), a mixture of dialkylurea derivative / monoalkylurea derivative = 2/1 (weight ratio) (sample code H) was synthesized.
【００１５】実施例１ 試料記号Ａ〜Ｈおよび対照としての１２−ヒドロキシス
テアリン酸、ステアリン酸ナトリウムの、代表的な有機
液体に対するゲル化または固化能を試験した。各種有機
液体に本発明に係るゲル化または固化剤等を３重量％添
加したものを試験管に入れ、約６０℃以上に加熱後、常
温（２５℃）にて静置冷却したときの状態を観察し、こ
のときの内容物の流動性の有無、また流動性のないもの
についてはゲル化物の固さを調べた。得られた結果を第
１表に示す。本発明のジアルキルウレア誘導体を主成分
とするものを添加した有機液体は、従来のゲル化剤やワ
ックスに比べ少量の添加であるにもかかわらず、均一で
滑らかなゲル化物を形成することが明らかになった。ま
た調製したゲル化物を１ヵ月間にわたり毎日１０〜３０
℃の温度幅で変化させ、その状態を調べたところ、本発
明に係るものはすべて調製当初の状態を維持しており、
長期間の温度変化に対して安定性に優れていることを確
認した。なお、評価は４段階評価（◎・・・流動性な
し：ゲル化物は均一で固い、○・・・流動性なし：ゲル
化物は均一で軟らかい、△・・・流動性ややあり、×・
・・不均一混合物または均一だが流動性あり）で行っ
た。Example 1 The sample symbols A through H and 12-hydroxystearic acid as a control, sodium stearate, were tested for their ability to gel or solidify against typical organic liquids. Various organic liquids containing 3% by weight of the gelling agent or the solidifying agent according to the present invention were placed in a test tube, heated to about 60 ° C. or higher, and then allowed to stand at room temperature (25 ° C.) for cooling. The contents were observed at this time for the presence or absence of fluidity, and for those without fluidity, the hardness of the gelled product was examined. The results obtained are shown in Table 1. It is clear that the organic liquid containing the dialkylurea derivative of the present invention as the main component forms a uniform and smooth gelated product, although the amount thereof is smaller than that of the conventional gelling agent or wax. Became. Also, prepare the gelled product for 10 to 30 days daily for one month.
By changing the temperature range of ° C., and examining the state, all of the present invention maintains the state of the initial preparation,
It was confirmed that the stability was excellent against long-term temperature changes. The evaluation is a four-level evaluation (◎: no fluidity: gelled substance is uniform and hard, ◯: no fluidity: gelled substance is uniform and soft, Δ: slightly fluidized, ×
..With a heterogeneous mixture or homogeneous but fluid).
【００１６】[0016]
【表１】 [Table 1]
【００１７】[0017]
【発明の効果】本発明によれば、前記一般式（Ｉ）で示
されるジアルキルウレア誘導体を比較的簡便に製造する
ことができ、これを有効成分として、動植物油脂、エス
テル、ポリオール、エーテル、アルコール、炭化水素系
油剤等の幅広い有機液体に対し、あるいは廃食用油、廃
潤滑油、廃金属加工油剤等に対して、少量の添加で、均
一で良好な、長期保存および温度変化に対して安定性に
優れたゲル化物または固化物を調製し得る。INDUSTRIAL APPLICABILITY According to the present invention, the dialkylurea derivative represented by the above general formula (I) can be produced in a relatively simple manner. Using this as an active ingredient, animal and vegetable oils and fats, esters, polyols, ethers, alcohols. , A wide range of organic liquids such as hydrocarbon-based oils, or even small amounts of waste edible oils, waste lubricating oils, waste metalworking oils, etc., even and good, stable for long-term storage and temperature changes A gelled product or a solidified product having excellent properties can be prepared.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ１０Ｎ 50:10 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code Agency reference number FI Technical display location C10N 50:10
Claims (3)
〜１８で飽和の直鎖状および／または分岐状アルキル基
を有するアルキルイソシアネートとを反応させて得られ
る、下記一般式（Ｉ） 【化１】 （式（Ｉ）中、Ｒは炭素数２〜１８の飽和直鎖状および
／または飽和分岐状アルキル基を表わす。）で示される
ジアルキルウレア誘導体を有効成分とする有機液体のゲ
ル化または固化剤。1. Diaminocyclohexane having 2 carbon atoms
A compound represented by the following general formula (I), obtained by reacting with an alkyl isocyanate having a saturated linear and / or branched alkyl group at -18. (In the formula (I), R represents a saturated linear and / or saturated branched alkyl group having 2 to 18 carbon atoms.) A gelling or solidifying agent of an organic liquid containing a dialkylurea derivative as an active ingredient. .
ミノシクロヘキサンである請求項１に記載のゲル化また
は固化剤。2. The gelling or solidifying agent according to claim 1, wherein the diaminocyclohexane is 1,2-diaminocyclohexane.
ール、エーテル、アルコール、炭化水素系油剤から選ば
れるものである請求項１に記載のゲル化または固化剤。3. The gelling or solidifying agent according to claim 1, wherein the organic liquid is selected from animal and vegetable oils, esters, polyols, ethers, alcohols, and hydrocarbon-based oil agents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6215395A JPH08231942A (en) | 1995-02-24 | 1995-02-24 | Gelling or solidifying agent for organic liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6215395A JPH08231942A (en) | 1995-02-24 | 1995-02-24 | Gelling or solidifying agent for organic liquid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08231942A true JPH08231942A (en) | 1996-09-10 |
Family
ID=13191886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6215395A Pending JPH08231942A (en) | 1995-02-24 | 1995-02-24 | Gelling or solidifying agent for organic liquid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08231942A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0996029A3 (en) * | 1998-10-19 | 2002-07-31 | Canon Kabushiki Kaisha | Gel electrolyte, cell and electrochromic element |
| EP1177784A3 (en) * | 2000-08-04 | 2003-01-22 | Unilever Plc | Antiperspirant compositions |
| JP2003064346A (en) * | 2001-08-28 | 2003-03-05 | Kyodo Yushi Co Ltd | Gelling agent for organic liquid and method of producing gelled product |
| JP2003064047A (en) * | 2001-08-23 | 2003-03-05 | Tendou Seiyaku Kk | New cyclohexane derivative, organic gelling agent including the same and organogel |
| US6921747B2 (en) | 2003-04-28 | 2005-07-26 | Ajinomoto Co., Inc. | Basic amino acid derivatives |
| JP2007510791A (en) * | 2003-11-12 | 2007-04-26 | アプライド ナノ システムズ ベー．フェー． | Asymmetric gelling agent |
| WO2009078268A1 (en) | 2007-12-17 | 2009-06-25 | National University Corporation Yamaguchi University | Gelling agent containing fluoroalkyl derivative |
| JP2010282728A (en) * | 2009-06-02 | 2010-12-16 | Asahi Kasei E-Materials Corp | Lithium ion secondary battery |
| WO2011099572A1 (en) | 2010-02-12 | 2011-08-18 | 旭化成イーマテリアルズ株式会社 | Fluoroalkane derivative, gelling agent and gel composition |
| US8399136B2 (en) | 2009-02-18 | 2013-03-19 | Asahi Kasei E-Materials Corporation | Electrolyte solution for lithium ion secondary battery, lithium ion secondary battery, fluoroalkane derivative and gelling agent |
| US9118088B2 (en) | 2009-06-10 | 2015-08-25 | Asahi Kasei E-Materials Corporation | Electrolyte solution and lithium ion secondary battery using the same |
-
1995
- 1995-02-24 JP JP6215395A patent/JPH08231942A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0996029A3 (en) * | 1998-10-19 | 2002-07-31 | Canon Kabushiki Kaisha | Gel electrolyte, cell and electrochromic element |
| EP1177784A3 (en) * | 2000-08-04 | 2003-01-22 | Unilever Plc | Antiperspirant compositions |
| JP2003064047A (en) * | 2001-08-23 | 2003-03-05 | Tendou Seiyaku Kk | New cyclohexane derivative, organic gelling agent including the same and organogel |
| JP2003064346A (en) * | 2001-08-28 | 2003-03-05 | Kyodo Yushi Co Ltd | Gelling agent for organic liquid and method of producing gelled product |
| US6921747B2 (en) | 2003-04-28 | 2005-07-26 | Ajinomoto Co., Inc. | Basic amino acid derivatives |
| JP2007510791A (en) * | 2003-11-12 | 2007-04-26 | アプライド ナノ システムズ ベー．フェー． | Asymmetric gelling agent |
| WO2009078268A1 (en) | 2007-12-17 | 2009-06-25 | National University Corporation Yamaguchi University | Gelling agent containing fluoroalkyl derivative |
| US8399136B2 (en) | 2009-02-18 | 2013-03-19 | Asahi Kasei E-Materials Corporation | Electrolyte solution for lithium ion secondary battery, lithium ion secondary battery, fluoroalkane derivative and gelling agent |
| KR101274298B1 (en) * | 2009-02-18 | 2013-06-13 | 고쿠리츠다이가쿠호우진 야마구치 다이가쿠 | Electrolytic solution for lithium-ion secondary battery, and lithium-ion secondary battery |
| JP2010282728A (en) * | 2009-06-02 | 2010-12-16 | Asahi Kasei E-Materials Corp | Lithium ion secondary battery |
| US9118088B2 (en) | 2009-06-10 | 2015-08-25 | Asahi Kasei E-Materials Corporation | Electrolyte solution and lithium ion secondary battery using the same |
| WO2011099572A1 (en) | 2010-02-12 | 2011-08-18 | 旭化成イーマテリアルズ株式会社 | Fluoroalkane derivative, gelling agent and gel composition |
| CN102725266A (en) * | 2010-02-12 | 2012-10-10 | 旭化成电子材料株式会社 | Fluoroalkane derivative, gelling agent and gel composition |
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