JPS62227434A - Novel surface-active agent - Google Patents
Novel surface-active agentInfo
- Publication number
- JPS62227434A JPS62227434A JP61072017A JP7201786A JPS62227434A JP S62227434 A JPS62227434 A JP S62227434A JP 61072017 A JP61072017 A JP 61072017A JP 7201786 A JP7201786 A JP 7201786A JP S62227434 A JPS62227434 A JP S62227434A
- Authority
- JP
- Japan
- Prior art keywords
- active agent
- surfactant
- alkyl
- group
- aralkyl
- 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
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 43
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- -1 alkyl phenol Chemical compound 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 13
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract description 5
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 2
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000003493 decenyl group Chemical group [H]C([*])=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 2
- 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 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 2
- 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 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 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 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 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 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 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 2
- 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 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
- 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 2
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 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 2
- 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 2
- 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 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 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 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 2
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 2
- 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 2
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 2
- 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 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012374 esterification agent Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000011041 water permeability test Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規な界面活性剤に関し、特にアリル基を有す
る半エステルカルボン酸型界面活性剤に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel surfactant, and particularly to a half-ester carboxylic acid type surfactant having an allyl group.
従来゛、界面活性剤は、乳化、分散、洗浄、湿潤、起泡
等の幅広い性能を有しており、それらの諸性能を利用し
て、繊維をはじめとし１紙、ゴム、プラスチック、金属
、塗料、顔料、土木建築等あらゆる分野に利用されてい
る。特に最近は界面活性剤を使用した末端商品の高性能
化への動きが活発化してきており、それに伴なって、界
面活性剤が有する副次的な欠点も指摘されている。Conventionally, surfactants have a wide range of properties such as emulsification, dispersion, cleaning, wetting, foaming, etc., and these properties are used to cure fibers, paper, rubber, plastics, metals, etc. It is used in various fields such as paints, pigments, and civil engineering and construction. Particularly recently, there has been an active movement toward improving the performance of end products using surfactants, and along with this, secondary drawbacks of surfactants have also been pointed out.
例えば、塗料、印刷インキ、接着剤、粘着剤などはその
製品の製造時、あるいは製品の安定化。For example, paints, printing inks, adhesives, pressure-sensitive adhesives, etc. are used during the manufacturing of the product or during product stabilization.
さらには作業性などの点で欠かすことができないもので
ある。それらの製品が、塗布、印刷あるいは接着、粘着
等の作業で使用された場合は、界面活性剤は不要であり
、むしろ存在している界面活性剤によって、塗膜、印刷
面、接着皮膜等の耐水性、耐油性等の性能を悪化Ｊせる
場合が多い。Furthermore, it is indispensable in terms of workability and the like. When these products are used for coating, printing, adhesion, adhesive, etc., surfactants are not necessary; rather, the surfactants present are used to form coatings, printed surfaces, adhesive films, etc. Performance such as water resistance and oil resistance often deteriorates.
これらの対策として界面活性剤の配合量の削減、界面活
性剤の高分子化等の方向で検討されているが、製品の安
定性、作業性等の点で未だ充分に解決されるまでには至
っていない。As a countermeasure to these problems, efforts are being made to reduce the amount of surfactants blended and use polymeric surfactants, but issues such as product stability and workability have yet to be fully resolved. Not yet reached.
一方、新しいタイプの界面活性剤の提供として、重合性
、反応性あるいは分解性の界面活性剤の特許が数多くみ
ちれる。On the other hand, in order to provide new types of surfactants, there are many patents for polymerizable, reactive, or degradable surfactants.
例えば、アニオン性の界面活性剤として、特公昭４Ｂ−
１２４７２号、特開昭５４−１４４３１号、特公昭４６
−３４８９４号、特公昭５６−２９６５７号、特開昭５
１−３０２８５号、特公昭４９−４６２９１号、特開昭
５６−１２７６９７号等かり、非イオン性界面活性剤と
して、特開昭５６−２８２０８号、特開昭５０−９８４
８４号等がある。For example, as an anionic surfactant,
No. 12472, JP-A-54-14431, JP-A-1973
-34894, Japanese Patent Publication No. 56-29657, Japanese Patent Publication No. 56-2965
1-30285, JP-A No. 49-46291, JP-A-56-127697, etc., as nonionic surfactants, JP-A-56-28208, JP-A-50-984.
There are issues such as No. 84.
これらの界面活性剤は主として、乳化重合用乳化剤とし
て種々の試みがなされているが、充分に満足できる実用
段階までには至っていない。Various attempts have been made to use these surfactants mainly as emulsifiers for emulsion polymerization, but they have not yet reached a fully satisfactory practical stage.
その理由として■前記特許に記載されている界面活性剤
が製造収率が極度に低い、または使用原料が著しく高価
である要因から、界面活性剤が非常に高価である。 ■
従来の界面活性剤に比べ、乳化、分散等の諸性能が劣る
。■重合性基等は有しているものの、使用用途にうまく
適合しない等の種々の欠点によるものである。The reason for this is: (1) The surfactant described in the above patent has an extremely low manufacturing yield, or the raw materials used are extremely expensive, so the surfactant is very expensive. ■
Compared to conventional surfactants, various performances such as emulsification and dispersion are inferior. (2) Although it has polymerizable groups, it has various drawbacks such as not being well suited to the intended use.
本発明者等は、これら問題点を解決すべく、鋭意研究の
結果、本発明に到達したものである。即ち、本発明は、
一般式、
厩 ２
［但し、上記式中Ｒ１は炭素数４〜１８のアルキル基、
アルケニル基、もしくはアラルキル基、Ｒ２は水素また
は炭素数４〜１８のアルキル基、アルケニル基、もしく
はアラルキル基、Ｒ３は−ＣＨ＝ＣＨ−であり、Ａは炭
素数２〜４のアルキレン基、もしくは置換アルキレン基
、ｎは１〜２００の整数であり、Ｍはアルカリ金属原子
、アルカノールアミン残基、またはＮＨ４である。〕で
表わされる化合物からなる新規界面活性剤を提供するも
のである。The present inventors have arrived at the present invention as a result of intensive research in order to solve these problems. That is, the present invention has the following formula: [However, in the above formula, R1 is an alkyl group having 4 to 18 carbon atoms,
Alkenyl group or aralkyl group, R2 is hydrogen or an alkyl group having 4 to 18 carbon atoms, alkenyl group, or aralkyl group, R3 is -CH=CH-, A is an alkylene group having 2 to 4 carbon atoms, or substituted The alkylene group, n is an integer from 1 to 200, and M is an alkali metal atom, an alkanolamine residue, or NH4. The present invention provides a novel surfactant comprising a compound represented by the following.
前記一般式中、Ｒ１は炭素数４〜１８のアルキル基、ア
ルケニル基、またはアラルキル基であり、アルキル基と
しては、例えばブチル、イソブチル、ペンチル、ヘキシ
ル、ヘプチル、オクチル。In the general formula, R1 is an alkyl group, alkenyl group, or aralkyl group having 4 to 18 carbon atoms, and examples of the alkyl group include butyl, isobutyl, pentyl, hexyl, heptyl, and octyl.
ノニル、デシル、ウンデシル、ドデシル、トリデシル、
テトラデシル、ペンタデシル、ヘキサデシル、ヘプタデ
シル、オクタデシル等が、挙げられる。nonyl, decyl, undecyl, dodecyl, tridecyl,
Examples include tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl and the like.
アルケニル基としては、例えば、ブテニル、インブテニ
ル、ペンテニル、ヘキセニル、ヘプテニル、オクテニル
、ノネニル、デセニル、ウンデセニル、ドデセニル、ト
リデセニル、テトラデセニル、ペンタデセニル、ヘキサ
デセニル、ヘプタデセニル、オクタデセニル等が挙げら
れる。アラルキル基としては、スチリル、ベンジル、ク
ミル等が挙げられ、これらの混合物であっても良い。Examples of the alkenyl group include butenyl, imbutenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, and the like. Examples of the aralkyl group include styryl, benzyl, cumyl, etc., and mixtures thereof may be used.
Ｒ２は水素または炭素数４〜１８のアルキル基、アルケ
ニル基、またはアラルキル基であり、アルキル基として
は、例えばブチル、イソブチル、ペンチル、ヘキシル、
ヘプチル、オクチル、ノニル、デシル、ウンデシル、ド
デシル、トリデシル、テトラデシル、ペンタデシル、ヘ
キサデシル、ヘプタデシル、オクタデシル、等が挙げら
れ、これらの混合物であっても良い。R2 is hydrogen or an alkyl group, alkenyl group, or aralkyl group having 4 to 18 carbon atoms, and examples of the alkyl group include butyl, isobutyl, pentyl, hexyl,
Examples include heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, and mixtures thereof.
アルケニル基としては、例えば、ブテニル、インブテニ
ル、ペンテニル、ヘキセニル、ヘプテニル、オクテニル
、ノネニル、デセニル、ウンデセニル、ドデセニル、ト
リデセニル、テトラデセニル、ペンタデセニル、ヘキサ
デセニル、ヘプタデセニル、オクタデセニル等が挙げら
れ、これらの混合物であっても良い。Examples of the alkenyl group include butenyl, imbutenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, and mixtures thereof. good.
アラルキル基としては、スチリル、ベンジル。Examples of aralkyl groups include styryl and benzyl.
クミル等が挙げられ、これらの混合物であっても良い。Examples include cumyl, and mixtures thereof may also be used.
また、Ａは炭素数２〜４のアルキレン基または置換アル
キレン基であり、例えば、エチレン、プロピレン、ブチ
レン、インブチレン等であり、それらの単独またはブロ
ックあるいはランダムの混合物であっても良い。Further, A is an alkylene group or substituted alkylene group having 2 to 4 carbon atoms, such as ethylene, propylene, butylene, imbutylene, etc., and may be a single group or a block or random mixture thereof.
ｎは１〜２００の整数であり、より好ましくは２〜１０
０の範囲である０Ｍはナトリウム、カリウム等のアルカ
リ金属原子、アンモニウム基、もしくはモノエタノール
アミン、トリエタノールアミン等のフルカノールアミン
残基が挙げられ、これらの混合物であっても良い。n is an integer of 1 to 200, more preferably 2 to 10
The range of 0M includes alkali metal atoms such as sodium and potassium, ammonium groups, or flukanolamine residues such as monoethanolamine and triethanolamine, and may be a mixture thereof.
さらに、本発明の界面活性剤は工業的に容易に製造でき
るものであり、例えば次のようにして製造することがで
きる。即ち、ノニルフェノール等のアルキルフェノール
を原料とし、アリルクロライドを触媒存在下のもとで加
熱反応し、その後、減圧にて蒸留する。このようにして
得られた反応組成物に、更に、アルキレンオキサイドを
常法にて、付加させる０次に無水マレイン酸、無水フタ
ル酸等にて半エステル化したのち、アルカリ物質で中和
することにより、本発明の界面活性剤を得ることができ
る。Furthermore, the surfactant of the present invention can be easily manufactured industrially, and can be manufactured, for example, as follows. That is, using an alkylphenol such as nonylphenol as a raw material, allyl chloride is heated and reacted in the presence of a catalyst, and then distilled under reduced pressure. To the reaction composition obtained in this way, an alkylene oxide is further added in a conventional manner. After semi-esterification with maleic anhydride, phthalic anhydride, etc., neutralization with an alkaline substance is performed. Accordingly, the surfactant of the present invention can be obtained.
本発明の新規界面活性剤は、特に問題とした塗料、印刷
インキ、接着剤、粘着剤等の如く、それらの製品の製造
時あるいは製品保管時、さらには加工時に有効に界面活
性剤として作用したのち、速やかに界面活性剤としての
諸機能を停止したいという需要業界の期待に応えること
ができる。The novel surfactant of the present invention effectively acts as a surfactant during manufacturing, storage, and processing of such products as paints, printing inks, adhesives, pressure-sensitive adhesives, etc., which are particularly problematic. Thereafter, it can meet the expectations of industries that demand that various functions as a surfactant be promptly stopped.
この場合、塗装、印刷、接着といった工程前に適当な重
合促進剤を加えるか、加工後紫外線、太陽光線加熱［キ
ユアリング］等による重合を行なわせるかは任意である
。In this case, it is optional whether an appropriate polymerization accelerator is added before the painting, printing, or adhesion process, or whether polymerization is carried out by ultraviolet rays, solar heating (curing), etc. after processing.
また、本発明の新規界面活性剤は、さらに乳化重合用乳
化剤、懸濁重合用分散剤、染料、顔料分散剤、ワックス
等の乳化剤、繊維後加工処理剤、山薬用乳化、分散剤、
合成樹脂用帯電防止剤等の用途に利用でき、使用後に残
存する界面活性剤の悪影響を軽減することが図れる。In addition, the novel surfactant of the present invention can further be used as an emulsifier for emulsion polymerization, a dispersant for suspension polymerization, a dye, a pigment dispersant, an emulsifier such as wax, a fiber post-processing agent, an emulsifier for mountain medicine, a dispersant,
It can be used as an antistatic agent for synthetic resins, and can reduce the adverse effects of surfactants remaining after use.
以下本発明を実施例により、具体的に説明するが、本発
明はこれらに限定されるものでない。EXAMPLES The present invention will be specifically explained below with reference to Examples, but the present invention is not limited thereto.
［％、部とあるは重量基準を示す、］
製製造例
攪拌機、温度計、還流管を備えた反応容器にノニルフェ
ノール２２０ｇ［１，０モル］、触媒として炭酸カリウ
ム５ｇを仕込み、つぎに７サルクロライド８４ｇ［１，
１モル］を滴下し４０℃にて２時間攪拌した。[%, parts and parts are based on weight] Production Example: Into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 220 g [1.0 mol] of nonylphenol and 5 g potassium carbonate as a catalyst were charged, and then 7 monkeys were charged. Chloride 84g [1,
1 mol] was added dropwise and stirred at 40°C for 2 hours.
その後、温度を２２０℃に昇温し、３時間攪拌した後、
減圧にて分溜し、アリルノニルフェノール２０９ｇを得
た。この収率は約８０％であった。After that, the temperature was raised to 220°C and stirred for 3 hours,
Fractional distillation was carried out under reduced pressure to obtain 209 g of allylnonylphenol. The yield was about 80%.
次に、分溜して得られたアリルノニルフェノールをオー
トクレーブに移し、苛性カリウムを触媒として、圧力１
．５ ｋｇ／ｃｍ２．温度１３０℃の条件にてエチレン
オキサイドを７リルノニルフエノールに対して、１０モ
ル付加し、アリルノニルフェノールエチレンオキシド１
０モル付加体を得た。Next, the allylnonylphenol obtained by fractional distillation was transferred to an autoclave, and the pressure was 1°C using caustic potassium as a catalyst.
．． 5 kg/cm2. At a temperature of 130°C, 10 moles of ethylene oxide was added to 7lyl nonylphenol to obtain 1 mol of allylnonylphenol ethylene oxide.
A 0 molar adduct was obtained.
次に、攪拌機、温度計、冷却管を備えた反応容器にアリ
ルノニルフェノールエチレンオキシド１０モル付加体３
５０ ｇ ［０、５モル］、無水マレイン酸４９ｇ［０
，５モル］を仕込み、８０℃に昇温し、３時間攪拌しな
がら反応を行ないマレイン酸の半エステルを得た０次に
水１６００ｇを加え希釈した後、４８％苛性ソーダ４ｔ
、７ｇ［０゜５モル］にて中和して、得られた組成物を
本発明の界面活性剤［Ａ］とした。Next, 10 moles of allylnonylphenol ethylene oxide adduct 3 was placed in a reaction vessel equipped with a stirrer, a thermometer, and a cooling tube.
50 g [0,5 mol], maleic anhydride 49 g [0
, 5 mol] was heated to 80°C and the reaction was carried out with stirring for 3 hours to obtain a half ester of maleic acid. Next, 1600 g of water was added for dilution, and 4 tons of 48% caustic soda was added.
, 7 g [0.5 mol], and the resulting composition was designated as the surfactant [A] of the present invention.
製造例２
製造例１のノニルフェノールの代りにオクチルフェノー
ルを用いて、同様の合成法にてアリルオクチルフェノー
ルを得た。Production Example 2 Allyl octylphenol was obtained by the same synthesis method as in Production Example 1, except that octylphenol was used instead of nonylphenol.
このアリルオクチルフェノールに対して第１表に示すよ
うに各種のフルキレンオキサイドを常法により付加し、
無水コハク酸との半エステルを製造し、アルカリ物質に
て中和することにより得られた組成物を、本発明の界面
活性剤［Ｂ］〜［Ｅ］とし、それらを第１表に示した。Various fullkylene oxides are added to this allyl octylphenol by a conventional method as shown in Table 1,
The compositions obtained by producing a half ester with succinic anhydride and neutralizing it with an alkaline substance were designated as surfactants [B] to [E] of the present invention, and they are shown in Table 1. .
製造例３
硫酸化剤として重亜硫酸ナトリウムに替えて重亜硫酸ア
ンモニウム、およびエステル化剤として無水フタル酸を
用いて製造例１の合成法に準じて第２表に示した本発明
の界面活性剤［Ｆ］〜［Ｈ］を合成した。Production Example 3 The surfactant of the present invention shown in Table 2 was prepared according to the synthesis method of Production Example 1 using ammonium bisulfite instead of sodium bisulfite as the sulfating agent and phthalic anhydride as the esterifying agent. F] to [H] were synthesized.
実施例１
製造例１．２．３で得られた本発明の界面活性剤［Ａ］
〜［Ｈ］について、その水溶液の表面張力を測定した。Example 1 Surfactant [A] of the present invention obtained in Production Example 1.2.3
The surface tension of the aqueous solution of ~[H] was measured.
尚、比較品として従来の界面活性剤の表面張力も併せて
示した。［表面張力はトラナベ法にて測定した。］その
結果を第３表に示した。The surface tension of a conventional surfactant is also shown as a comparative product. [Surface tension was measured by the Tranabe method. ] The results are shown in Table 3.
実施例２
製造例１．２で得られた本発明の界面活性剤［Ａ］、
［Ｂ］について、カーボンブラックの分散性能およびト
ルエンの乳化性能を測定した。Example 2 Surfactant [A] of the present invention obtained in Production Example 1.2,
Regarding [B], carbon black dispersion performance and toluene emulsification performance were measured.
尚、比較品として従来の界面活性剤の性能も同様に測定
した。その結果を第４表に示した。The performance of a conventional surfactant was also measured in the same manner as a comparative product. The results are shown in Table 4.
試験方法は下記の通りである。The test method is as follows.
［分散性能試験方法］
容器１００ ｍ ｌの共栓付メスシリンダーに界面活性
剤１ｇ、カーボンブラックｌＯｇを入れ、水にて溶解分
散させ１００ｍ１に調節した。[Dispersion performance test method] 1 g of surfactant and 10 g of carbon black were placed in a 100 ml measuring cylinder with a stopper, and dissolved and dispersed with water to adjust the volume to 100 ml.
次に、そのメスシリンダーを１分間に１００回振盪し、
１時間２５℃にて静置した。その後、液上面から３０ｃ
ｃ抜き取りグラスフィルターにて濾過した後、１０５℃
にて、乾燥させ、グラスフィルター上の残香の重量より
分散性を次式により測定した。Next, shake the graduated cylinder 100 times per minute,
It was left standing at 25°C for 1 hour. After that, 30c from the top of the liquid.
105℃ after filtration with a glass filter
The dispersibility was measured from the weight of the residual fragrance on the glass filter using the following formula.
分散性能（％）＝
グラスフィルターの成立重量（ｇ）
［乳化性能試験方法］
容量２０ ｍ ｌの目盛付き共栓付試験管に０．５％界
面活性剤水溶液５ｍｌとケロシン５ ｍ ｌを加え、１
分間に１００回振盪した後、１時間２５℃にて静置した
。その後、乳化層の容量（ｍｌ）を測定し、乳化性を次
式により測定した。Dispersion performance (%) = established weight of glass filter (g) [Emulsification performance test method] Add 5 ml of 0.5% surfactant aqueous solution and 5 ml of kerosene to a 20 ml capacity test tube with a graduated stopper. 1
After shaking 100 times per minute, the mixture was allowed to stand at 25° C. for 1 hour. Thereafter, the volume (ml) of the emulsified layer was measured, and the emulsifying property was measured using the following formula.
乳化層（ｍｌ）
乳化性能（％）＝ Ｘ１０Ｘ実施例３
第５表に示す界面活性剤５ｇ、鹸化度８８モル％粘度平
均重合度１７００のポリビニルアルコール３０ｇを水３
００ｇに分散させ、加温攪拌して溶解させる。過硫酸ア
ンモニウム１ｇを開始剤とし、常法により酢酸ビニルモ
ノマー２４０ｇを滴下し、′乳化重合してエマルジョン
組成物を得た。Emulsifying layer (ml) Emulsifying performance (%) = X10
00g and stirred while heating to dissolve. Using 1 g of ammonium persulfate as an initiator, 240 g of vinyl acetate monomer was added dropwise in a conventional manner, followed by emulsion polymerization to obtain an emulsion composition.
このエマルジョン組成物に造膜助剤としてジブチルフタ
レートを３０ｇ配合し、接着力を測定した。その結果を
第５表に示した。30 g of dibutyl phthalate was added as a film forming aid to this emulsion composition, and the adhesive strength was measured. The results are shown in Table 5.
実施例４
ポリプロピレンから作られた不織布（２，５ｃｍＸ１０
ｃｍ）を、第６表に示す界面活性剤の１％水溶液に１分
間浸漬し、取り出し後、１２０℃にて３０分間熱風乾燥
を行なった。Example 4 Non-woven fabric made from polypropylene (2.5 cm x 10
cm) was immersed for 1 minute in a 1% aqueous solution of the surfactant shown in Table 6, and after taking it out, it was dried with hot air at 120° C. for 30 minutes.
上記界面活性剤処理した不織布を水５０ｍ１の入った１
００ｍ１ビーカー上につるし、不織布の下部から１ｃｍ
だけ水中に浸し、５分後の水の浸透高さを測定した。［
洗濯前］
さらに耐洗濯性を観察するために、処理乾燥後の不織布
を流水にて１分間洗浄した後、乾燥させ上記と同様の水
の浸透性の試験を行なった。［洗濯後］その結果を第６
表に示した。Add the above surfactant-treated nonwoven fabric to 50ml of water.
Hang it over a 00m1 beaker, 1cm from the bottom of the nonwoven fabric.
The sample was immersed in water, and the height of water penetration after 5 minutes was measured. [
Before washing] In order to further observe washing resistance, the nonwoven fabric after treatment and drying was washed with running water for 1 minute, dried, and subjected to the same water permeability test as above. [After washing] Check the results on the 6th page.
Shown in the table.
第３表
第４表
第５表
第６表
特許出願人 第−工業製薬株式会社
手続補正書
昭和６１年 ７月 ８日
昭和６１年 特許顆路７２０１７ 号２、発明の名
称
新規界面活性剤
３、補正をする者
事件との関係 特許出願人
４、補正命令の日付
自発補正
５、補正により増加する発明の数
７、補正の内容
本願を原明細書に基づき次の通り補正する。Table 3 Table 4 Table 5 Table 6 Patent Applicant No. - Kogyo Seiyaku Co., Ltd. Procedural Amendment July 8, 1985 Patent No. 72017 No. 2, Title of Invention New Surfactant 3, Relationship with the case of the person making the amendment Patent applicant 4, date of amendment order voluntary amendment 5, number of inventions increased by amendment 7, content of amendment The present application is amended as follows based on the original specification.
（１）明細書路１１頁７行〜同１２行目「製造例３
硫醜化剤として重亜硫酸ナトリウムに替えて重亜硫酸ア
ンモニウム、およびエステル化剤として無水フタル酸を
用いて製造例１の合成法に準じて第２表に示した本発明
の界面活性剤［Ｆ］〜［Ｈ］を合成した。Ｊとあるを、
「製造例３
エステル化剤として無水フタル酸を用いて製造例１の合
成法に準じて第２表に示した本発明の界面活性剤［Ｆ］
〜［Ｈ］を合成した。」と訂正する。(1) Specification page 11, line 7 to line 12 "Production Example 3 Synthesis method of Production Example 1 using ammonium bisulfite instead of sodium bisulfite as the sulfur disfiguring agent and phthalic anhydride as the esterification agent" The surfactants [F] to [H] of the present invention shown in Table 2 were synthesized according to the above. Surfactant [F] of the present invention shown in Table 2 according to the Act
~[H] was synthesized. ” he corrected.
以上that's all
Claims (1)
、アルケニル基、もしくはアラルキル基、Ｒ＿２は水素
または炭素数４〜１８のアルキル基、アルケニル基、も
しくはアラルキル基、Ｒ＿３は▲数式、化学式、表等が
あります▼、−ＣＨ＿２−ＣＨ＿２−、もしくは−ＣＨ
＝ＣＨ−であり、Ａは炭素数２〜４のアルキレン基、も
しくは置換アルキレン基、ｎは１〜２００の整数であり
、Ｍはアルカリ金属原子、アルカノールアミン残基、ま
たはＮＨ＿４である。］で表わされる化合物からなる新
規界面活性剤。[Claims] There are general formulas, ▲mathematical formulas, chemical formulas, tables, etc.▼ [However, in the above formula, R_1 is an alkyl group, alkenyl group, or aralkyl group having 4 to 18 carbon atoms, and R_2 is hydrogen or a carbon number 4 ~18 alkyl group, alkenyl group, or aralkyl group, R_3 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2-CH_2-, or -CH
=CH-, A is an alkylene group having 2 to 4 carbon atoms or a substituted alkylene group, n is an integer of 1 to 200, and M is an alkali metal atom, an alkanolamine residue, or NH_4. ] A novel surfactant consisting of a compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61072017A JPS62227434A (en) | 1986-03-28 | 1986-03-28 | Novel surface-active agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61072017A JPS62227434A (en) | 1986-03-28 | 1986-03-28 | Novel surface-active agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62227434A true JPS62227434A (en) | 1987-10-06 |
Family
ID=13477222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61072017A Pending JPS62227434A (en) | 1986-03-28 | 1986-03-28 | Novel surface-active agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62227434A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5990342A (en) * | 1995-07-25 | 1999-11-23 | Asahi Denka Kogyo K.K. | Surfactant, emulsifier for emulsion polymerization, dispersant for suspension polymerization and modifier for resin modification |
| JP2015000397A (en) * | 2013-06-18 | 2015-01-05 | 第一工業製薬株式会社 | Dispersant for non-aqueous dispersion medium |
-
1986
- 1986-03-28 JP JP61072017A patent/JPS62227434A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5990342A (en) * | 1995-07-25 | 1999-11-23 | Asahi Denka Kogyo K.K. | Surfactant, emulsifier for emulsion polymerization, dispersant for suspension polymerization and modifier for resin modification |
| JP2015000397A (en) * | 2013-06-18 | 2015-01-05 | 第一工業製薬株式会社 | Dispersant for non-aqueous dispersion medium |
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