JPS63240931A - Novel surfactant - Google Patents
Novel surfactantInfo
- Publication number
- JPS63240931A JPS63240931A JP61297230A JP29723086A JPS63240931A JP S63240931 A JPS63240931 A JP S63240931A JP 61297230 A JP61297230 A JP 61297230A JP 29723086 A JP29723086 A JP 29723086A JP S63240931 A JPS63240931 A JP S63240931A
- Authority
- JP
- Japan
- Prior art keywords
- group
- surfactant
- shows
- compd
- alkyl group
- 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 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000003342 alkenyl 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 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 239000003945 anionic surfactant Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001180 sulfating effect Effects 0.000 abstract description 2
- 230000002411 adverse Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005641 methacryl group Chemical group 0.000 abstract 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 abstract 1
- -1 sulfate ester Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 239000004745 nonwoven fabric Substances 0.000 description 5
- 239000000047 product 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
- 238000004945 emulsification Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
- 239000003054 catalyst Substances 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
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-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
- 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
- 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
- 239000000835 fiber Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000011521 glass Substances 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
- 125000005394 methallyl group Chemical group 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
- 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
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000012360 testing method Methods 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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group 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
- 239000003905 agrochemical Substances 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000605 extraction 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
- 239000000463 material 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
- 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
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage 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
- 238000011041 water permeability test Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明は新規界面活性剤に関し、特にメタリル基を有す
る新規な硫酸エステル型アニオン性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 novel sulfate ester type anionic surfactant having a methallyl 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、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, and foaming.Using these properties, surfactants can be used to improve materials such as 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させる
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. It often deteriorates performance such as water resistance and oil resistance.
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３”）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 countermeasures to these problems, efforts have been made to reduce the amount of surfactants blended and use polymeric surfactants, etc., but these problems are still not fully resolved in terms of product stability, workability, etc. It has not yet reached that point.
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
られる。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４６−
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
である安置から、界面活性剤が非常に高価である。 ■
従来の界面１１５性剤に比べ、乳化１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, making the surfactant very expensive. ■
Compared to conventional interfacial agents, 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 。Ｒ３
［但し、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、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、ＮＨ４、アルカノールアミン残基であ
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。前記一般式中、Ｒ１は炭素数４〜１
８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 is based on the general formula. R3 [However, R1 is an alkyl group, alkenyl group, or aralkyl group having 4 to 18 carbon atoms, R2 is hydrogen or an alkyl group, alkenyl group, or aralkyl group having 4 to 18 carbon atoms, and A is an alkyl group having 4 to 18 carbon atoms. An alkylene group or a substituted alkylene group, n is an integer of 1 to 200, and M is an alkali metal atom, NH4, or an alkanolamine residue. The present invention provides a novel surfactant comprising a compound represented by the following. In the general formula, R1 has 4 to 1 carbon atoms
8 alkyl group, alkenyl group, or aralkyl group, and examples of the alkyl group include butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl,
Examples include decyl, undecyl, dodecyl, tridecyl, 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、（とじては、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. Aralkyl groups include styryl, benzyl, cumyl, etc., and may also be mixtures thereof.
Ｒ２は水素原子または炭素ａ４〜１８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 a hydrogen atom or an alkyl group, alkenyl group, or aralkyl group having carbon a4 to a18, and examples of the alkyl group include butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, Examples include 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、インフチニ
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、トチセニル、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, inftynyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, tothycenyl, 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、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 aralkyl group include styryl, benzyl, cumyl, etc., and mixtures thereof may be used.
また、Ａは炭素数２〜４のフ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、イソブチレン等であり、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 a fullkylene group or a substituted alkylene group having 2 to 4 carbon atoms, such as ethylene, propylene, butylene, isobutylene, 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〜ｌＯ
Ｏ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、アンモニウムまた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 1O
The 0M range of O includes alkali metals such as sodium and potassium, ammonium, and flukanolamine groups 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。Furthermore, the surfactant of the present invention can be easily manufactured industrially, and can be manufactured, for example, as follows.
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、メタ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。That is, an alkylphenol such as nonylphenol is used as a raw material, methallyl chloride is heated and reacted in the presence of a catalyst, and then distilled under reduced pressure.
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次に硫酸、スル
ファミン酸等の硫酸化剤にて硫酸化を行ない、必要によ
り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。To the reaction composition obtained in this way, alkylene oxide is further added in a conventional manner. Next, sulfation is carried out using a sulfating agent such as sulfuric acid or sulfamic acid, and if necessary, neutralization is carried out with an alkaline substance. By doing so, 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。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. after.
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。It can meet the expectations of industries that demand that various functions as a surfactant be quickly 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１．さらに乳化重合用
乳化剤、懸：ｆＪｇ！、台用分散剤、染料、顔料分散剤
、ワックス等の乳化剤、繊維後加工処理剤。Moreover, the novel surfactant of the present invention has 1. Furthermore, an emulsifier for emulsion polymerization: fJg! , table dispersants, dyes, pigment dispersants, emulsifiers for wax, etc., and fiber post-processing agents.
農薬用乳化、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。It can be used as an emulsifier for agricultural chemicals, a dispersant, an antistatic agent for synthetic resins, etc., and can reduce the negative effects of surfactants that remain 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 ７！準を示す、コ製造例１
攪拌機、温度計、還流管を備えた反応容器に７ニルフ工
ノール２２０ｇ ［１，０モル］、触媒として炭酸カリ
ウム５ｇを仕込み、つぎにメタリルクロライド１１７ｇ
［１，１モル］を滴下し４０℃にて２時間攪拌した。[%, part and weight are 7! Production Example 1: Into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 220 g [1.0 mol] of 7-nilphenol and 5 g of potassium carbonate as a catalyst were charged, followed by 117 g of methallyl chloride.
[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、メタリルノニルフェノール２２０ｇを
得た。 この収率は約８０％であった０次に、分溜して
得られたメタ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１．５ｋｇ／ａ
ｍ２、温度１３０℃の条件にてエチレンオキサイドをメ
タリルノニルフェノールに対して、１０モル付加シ、メ
タリルノニルフェノールエチレンオキシド１０モル付加
体を得た。After that, the temperature was raised to 220°C and stirred for 3 hours,
Fractional distillation was carried out under reduced pressure to obtain 220 g of methallylnonylphenol. The yield was about 80%.Next, the methallylnonylphenol obtained by fractional distillation was transferred to an autoclave, and the pressure was 1.5 kg/a using caustic potassium as a catalyst.
10 moles of ethylene oxide was added to methallylnonylphenol at a temperature of 130° C. to obtain a 10 mole adduct of methallylnonylphenol ethylene oxide.
次に、攪拌機、温度計を備えた反応容器にメタリルノニ
ルフェノールエチレンオキシド１０モル付加体３５７ｇ
［０，５モル］、スルファミン酸５８．２ｇ［０，６
モル］を仕込み、１２０℃に昇温し、３時間攪拌反応し
、硫酸化を行なった。Next, 357 g of 10 mole adduct of methallylnonylphenol ethylene oxide was placed in a reaction vessel equipped with a stirrer and a thermometer.
[0,5 mol], sulfamic acid 58.2 g [0,6
mol] was charged, the temperature was raised to 120°C, and the reaction was stirred for 3 hours to perform sulfation.
未反応スルファミン酸を日別除去して、得られた組成物
を本発明の界面活性剤［Ａ］ とした。Unreacted sulfamic acid was removed daily, and the resulting composition was designated as the surfactant [A] of the present invention.
製造例２
製造例１の７ニルフエノールの代りにオクチルフェノー
ルを用いて、同様の合成法にてメタリルオクチルフェノ
ールを得た。Production Example 2 Methallyl octylphenol was obtained by the same synthesis method as in Production Example 1, except that octylphenol was used instead of 7-nylphenol.
このメタ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
、スルファミン酸を用いて硫酸化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。The surfactant [B ] ~ [E] and
They are shown in Table 1.
製造例３
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 Surfactants [F] to [H] of the present invention shown in Table 2 were synthesized according to the synthesis method of Production Example 1.
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、比較量として従来の界面活性剤の表面張力も併せて
示した。その結果を第３表に示した。［表面張力はトラ
ナベ法にて測定した。］
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。In addition, the surface tension of a conventional surfactant is also shown as a comparative amount. The results are shown in Table 3. [Surface tension was measured by the Tranabe method. ] Example 2 Surfactant [A] of the present invention obtained in Production Example 1.2, [
Regarding B], the dispersion performance of carbon black and the emulsification performance of toluene were measured.
尚、比較量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。Note that the performance of a conventional surfactant was also measured in the same manner as a comparative amount. 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１００ｍ１の共栓付メスシリンダーに界面活性剤１
ｇ、カーボンブラックｌＯｇを入れ、水にて溶解分散さ
せ１００ｍ１に調箇した。[Dispersion performance test method] Surfactant 1 in a 100m1 graduated cylinder with a stopper
g and 10 g of carbon black were added, dissolved and dispersed in water, and the volume was adjusted 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」二面から３０
ｃｃ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駿よ
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. Then, 30 minutes from the second side of the liquid.
After filtering with a cc extraction glass filter, 105
It was dried at ℃, and the dispersibility of the remaining fragrance was measured using the following formula.
分散性能（％）＝
グラスフィルターの残在重量ｃｇ）
［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５ｍｌ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、乳化層の合端（ｍｌ）を測定し、乳化性を次式に
より測定した。Dispersion performance (%) = remaining weight of glass filter (cg) [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 and test for 1 minute. After shaking 100 times, the mixture was allowed to stand at 25° C. for 1 hour. Thereafter, the joint end (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、Ｍ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, and emulsion polymerization was carried out 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（２，５ｃｍＸＩＯ
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 XIO
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
００ ｍ ｌ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.
The nonwoven fabric was suspended over a 00 ml beaker and immersed in water 1 cm from the bottom of the nonwoven fabric, and the height of water penetration after 5 minutes was measured. [Before washing] In order to further observe the washing resistance, the nonwoven fabric after treatment and drying was washed with running water for 1 minute, dried, and the same water permeability test as above was conducted. [After washing] Check the results on the 6th page.
Shown in the table.
第３表 第４表 ！８５表 第６表Table 3 Table 4 ! 85 tables Table 6
Claims (1)
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、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、ＮＨ＿４、アルカノールアミン残
基である。］で表わされる化合物からなる新規界面活性
剤。[Claims] General formula▲ Numerical formula, chemical formula, table, etc.▼ [However, R_1 is an alkyl group, alkenyl group, or aralkyl group having 4 to 18 carbon atoms, and R_2 is hydrogen or an alkyl group having 4 to 18 carbon atoms. group, alkenyl group, or aralkyl group, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, n is an integer of 1 to 200, M
is an alkali metal atom, NH_4, and an alkanolamine residue. ] A novel surfactant consisting of a compound represented by:
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61297230A JPS63240931A (en) | 1986-12-12 | 1986-12-12 | Novel surfactant |
| US07/119,460 US4918211A (en) | 1986-12-12 | 1987-11-10 | Surface active compounds having a polymerizable moiety |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61297230A JPS63240931A (en) | 1986-12-12 | 1986-12-12 | Novel surfactant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63240931A true JPS63240931A (en) | 1988-10-06 |
Family
ID=17843850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61297230A Pending JPS63240931A (en) | 1986-12-12 | 1986-12-12 | Novel surfactant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63240931A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2397531A1 (en) | 2010-06-17 | 2011-12-21 | Ricoh Company, Ltd. | Heat-sensitive adhesive material |
| JP2015000397A (en) * | 2013-06-18 | 2015-01-05 | 第一工業製薬株式会社 | Dispersant for non-aqueous dispersion medium |
| WO2017098875A1 (en) | 2015-12-07 | 2017-06-15 | 昭和電工株式会社 | Mortar composition and method for manufacturing same, concrete structure, and concrete framework foundation adjusting method |
| WO2018155032A1 (en) | 2017-02-27 | 2018-08-30 | 昭和電工株式会社 | Curable aqueous resin emulsion composition |
-
1986
- 1986-12-12 JP JP61297230A patent/JPS63240931A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2397531A1 (en) | 2010-06-17 | 2011-12-21 | Ricoh Company, Ltd. | Heat-sensitive adhesive material |
| JP2015000397A (en) * | 2013-06-18 | 2015-01-05 | 第一工業製薬株式会社 | Dispersant for non-aqueous dispersion medium |
| WO2017098875A1 (en) | 2015-12-07 | 2017-06-15 | 昭和電工株式会社 | Mortar composition and method for manufacturing same, concrete structure, and concrete framework foundation adjusting method |
| WO2018155032A1 (en) | 2017-02-27 | 2018-08-30 | 昭和電工株式会社 | Curable aqueous resin emulsion composition |
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