JPH042714B2 - - Google Patents
Info
- Publication number
- JPH042714B2 JPH042714B2 JP20869087A JP20869087A JPH042714B2 JP H042714 B2 JPH042714 B2 JP H042714B2 JP 20869087 A JP20869087 A JP 20869087A JP 20869087 A JP20869087 A JP 20869087A JP H042714 B2 JPH042714 B2 JP H042714B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- group
- surfactant
- ethylene oxide
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 238000012805 post-processing Methods 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 36
- 239000004094 surface-active agent Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- -1 pentadecenyl Chemical group 0.000 description 18
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 239000003518 caustics Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 229910015900 BF3 Inorganic materials 0.000 description 6
- 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 6
- 238000003756 stirring Methods 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- XDESGXRLUIHEJT-UHFFFAOYSA-N 2,3,4-tribenzylphenol Chemical compound C=1C=CC=CC=1CC1=C(CC=2C=CC=CC=2)C(O)=CC=C1CC1=CC=CC=C1 XDESGXRLUIHEJT-UHFFFAOYSA-N 0.000 description 1
- ROOPEIGRBDVOKP-UHFFFAOYSA-N 2,3-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC=CC(O)=C1C(C)CC ROOPEIGRBDVOKP-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- NSENZNPLAVRFMJ-UHFFFAOYSA-N 2,3-dibutylphenol Chemical compound CCCCC1=CC=CC(O)=C1CCCC NSENZNPLAVRFMJ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- IQGWPPQNIZBTBM-UHFFFAOYSA-N 2-aminoethanol;sulfuric acid Chemical compound NCCO.OS(O)(=O)=O IQGWPPQNIZBTBM-UHFFFAOYSA-N 0.000 description 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 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
- 230000000052 comparative effect Effects 0.000 description 1
- 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 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
- 239000006185 dispersion Substances 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 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
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000976 ink Substances 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
- 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
- 238000000034 method Methods 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
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 239000002736 nonionic surfactant Substances 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
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- VSXGXPNADZQTGQ-UHFFFAOYSA-N oxirane;phenol Chemical class C1CO1.OC1=CC=CC=C1 VSXGXPNADZQTGQ-UHFFFAOYSA-N 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
- 239000000123 paper Substances 0.000 description 1
- 230000035515 penetration Effects 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
- JSPKFLGISILEDM-UHFFFAOYSA-N phenol;styrene Chemical class OC1=CC=CC=C1.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 JSPKFLGISILEDM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 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
- 239000002994 raw material Substances 0.000 description 1
- 239000005060 rubber 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
- 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
- 239000000126 substance Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 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
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 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
- 238000011041 water permeability test Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
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、プラスチツク、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、それに伴つて、界面活性
剤が有する副次的な欠点も指摘されている。
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、
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
性剤によつて、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。
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至つていない。
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。
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51−30285
号、特公昭49−46291号、特開昭56−127697号等
があり、非イオン性界面活性剤として、特開昭56
−28208号、特開昭50−98484号等がある。
本発明は、一般式
〔ただし、上記式中Ｒは炭素数８〜30のアルキル
基、アルケニル基、もしくはアルキルアリール
基、アラルキルアリール基、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
０〜100の整数であり、ｍ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ことを特徴とする繊
維後加工処理剤を提供する。
前記一般式中、Ｒは炭素数８〜30のアルキル
基、アルケニル基、アルキルアリール基、もしく
はアラルキルアリール基であり、アルキル基とし
ては、例えば、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、ノナデシル、エイコシル等が挙げら
れる。
アルケニル基としては、例えば、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。
アルキルアリール基としては、モノブチルフエ
ノール、ジブチルフエノール、sec−ブチルフエ
ノール、ジsec−ブチルフエノール、tert−ブチ
ルフエノール、オクチルフエノール、ノニルフエ
ノール、ジノニルフエノール、ドデシルフエノー
ル、ジデシルフエノール等が挙げられる。
アラルキルフエノールとしては、スチレン化フ
エノール、ベンジルフエノール、クミルフエノー
ル等のモノ、ジ、トリの単独あるいは、これらの
混合物等が挙げられ、これらのアルキル基等の混
合物であつてもよい。
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、イソブチレン等であり、そ
れらの単独またはブロツクあるいはランダムの混
合物であつても良い。
ｎは０〜100の整数、ｍは１〜200の整数であ
り、より好ましくはｎは０または１〜50、ｍは２
〜100の範囲である。
さらに、本発明の繊維後加工処理剤は工業的に
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。すなわち、ノニルフ
エノールまたはラウリルアルコールを原料とし、
要すればアルキレンオキサイドを付加し、アリル
グリシジルエーテルを触媒存在下のもとで加熱反
応し、得られた反応組成物に、さらに、アルキレ
ンオキサイドを常法にて付加させる。次に硫酸、
スルフアミン酸等の硫酸化剤にて硫酸化を行い、
必要により塩基性物質で中和することにより得る
ことができる。
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はな
い。（％、部とあるは重量基準を示す。）
製造例 １
撹拌機、温度計、還流管を備えた反応容器にノ
ニルフエノール220ｇ（1.0モル）、触媒としてト
リエチルアミン1.5ｇを仕込み、つぎにアリルグ
リシジルエーテル114ｇ（1.0モル）を滴下し100
℃にて５時間撹拌した。
次に、得られた反応組成物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／
cm2、温度130℃の条件にてエチレンオキサイドを
反応組成物に対して、10モル、30モル、100モル
付加して組成物を得た。次に、撹拌機、温度計を
備えた反応容器に上記反応組成物のエチレンオキ
サイド10モル付加体387ｇ（0.5モル）、スルフア
ミン酸58.2ｇ（0.6モル）を仕込み、120℃に昇温
し、３時間撹拌反応し、硫酸化を行つた。未反応
スルフアミン酸をロ別除去して得られた組成物
を、本発明界面活性剤〔Ａ〕とした。同様の操作
にて得られたエチレンオキサイド30モル付加体の
硫酸エステルアンモニウム塩を、本発明界面活性
剤〔Ｂ〕、エチレンオキサイド100モル付加体の硫
酸エステルアンモニムウ塩を、本発明界面活性剤
〔Ｃ〕とした。
製造例 ２
撹拌機、温度計、還流管を備えた反応容器にラ
ウリルアルコール186ｇ（1.0モル）、触媒として
三弗化ホウ素エーテル錯体0.6ｇを仕込み、次に
アリルグリシジルエーテル228ｇ（2.0モル）を滴
下し、80℃にて５時間撹拌した後に120℃に加温
し、減圧にて過剰のアリルグリシジルエーテルを
除去した。次に、得られた反応組成物をオートク
レーブに移し、苛性カリウムを触媒として、圧力
1.5Kg／cm2、温度130℃の条件にてエチレンオキサ
イドを反応組成物に対して、５モル、20モル、50
モル付加して得られた組成物を製造例１に準じて
硫酸化を行い、得られたエチレンオキサイド５モ
ル付加体の硫酸エステルアンモニウム塩を、本発
明界面活性剤〔Ｄ〕、エチレンオキサイド20モル
付加体の硫酸エステルアンモニウム塩を、本発明
界面活性剤〔Ｅ〕、エチレンオキサイド50モル付
加体の硫酸エステルアンモニウム塩を、本発明界
面活性剤〔Ｆ〕とした。
製造例 ３
撹拌機、温度計、還流管を備えた反応容器にジ
スチレン化フエノールエチレンオキサイド10モ
ル・プロピレンオキサイド２モルブロツク付加体
856ｇ（1.0モル）、触媒として三弗化ホウ素エー
テル錯体２ｇを仕込み、次にアリルグリシジルエ
ーテル228ｇ（2.0モル）を滴下し、80℃にて５時
間撹拌した後に120℃に加温し、減圧にて過剰の
アリルグリシジルエーテルを除去した。次に、得
られた反応組成物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／cm2、温度130
℃の条件にてエチレンオキサイドを反応組成物に
対して15モル、40モル付加して得られた組成物を
製造例１に準じて硫酸化を行い、得られたエチレ
ンオキサイド15モル付加体の硫酸エステルアンモ
ニウム塩を、本発明界面活性剤〔Ｇ〕、エチレン
オキサイド40モル付加体の硫酸エステルアンモニ
ウム塩を、本発明界面活性剤〔Ｈ〕とした。
製造例 ４
撹拌機、温度計、還流管を備えた反応容器にオ
レイルアルコールエチレンオキサイド30モル付加
体1588ｇ（1.0モル）、触媒として三弗化ホウ素エ
ーテル錯体３ｇを仕込み、次にアリルグリシジル
エーテル228ｇ（2.0モル）を滴下し、80℃にて５
時間撹拌した後に120℃に加温し、減圧にて過剰
のアリルグリシジルエーテルを除去した。次に得
られた反応組成物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／cm2、温度130
℃の条件にてエチレンオキサイド40モル、プロピ
レンオキサイド10モルを反応組成物に対してラン
ダムに付加して得られた組成物を、製造例１に準
じてスルフアミン酸を用いて硫酸化を行い、得ら
れた硫酸化物にスルフアミン酸と当量の苛性ソー
ダを加え、脱アンモニアを行い、得られた硫酸エ
ステルナトリウム塩を、本発明界面活性剤〔Ｉ〕
とした。
製造例 ５
撹拌機、温度計、還流管を備えた反応容器にス
テアリルアルコールプロピレンオキサイド２モル
付加体385ｇ（1.0モル）、触媒として三弗化ホウ
素エーテル錯体1.5ｇを仕込み、次いアリルグリ
シジルエーテル228ｇ（2.0モル）を滴下し、80℃
にて５時間撹拌した後に120℃に加温し、減圧に
て過剰のアリルグリシジルエーテルを除去した。
次に得られた反応組成物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／cm2、
温度130℃の条件にてエチレンオキサイドを２モ
ル、５モル付加して得られた組成物を製造例１に
準じて、スルフアミン酸を用いて硫酸化を行い、
得られた硫酸化物にスルフアミン酸と当量のモノ
エタノールアミンを加え、脱アンモニアを行い、
得られたエチレンオキサイド２モル付加体の硫酸
エステルモノエタノールアミン塩を、本発明界面
活性剤〔Ｊ〕、エチレンオキサイド５モル付加体
の硫酸エステルモノエタノールアミン塩を、本発
明界面活性剤〔Ｋ〕とした。
製造例 ６
撹拌機、温度計、還流管を備えた反応容器にジ
sec−ブチルフエノールブチレンオキサイド３モ
ル付加体278ｇ（1.0モル）、触媒として三弗化ホ
ウ素エーテル錯体１ｇを仕込み、次にアリルグリ
シジルエーテル228ｇ（2.0モル）を滴下し、80℃
にて５時間撹拌した後に120℃に加温し、減圧に
て過剰のアリルグリシジルエーテルを除去した。
次に得られた反応組成物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／cm2、
温度130℃の条件にて、プロピレンオキサイド２
モル、エチレンオキサイド15モルを反応組成物に
対して付加し、得られた組成物を製造例１に準じ
て硫酸化を行い、得られた硫酸エステルアンモニ
ウム塩を、本発明界面活性剤〔Ｌ〕とした。
製造例 ７
撹拌機、温度計、還流管を備えた反応容器にト
リベンジルフエノールエチレンオキサイド20モル
付加体1244ｇ（1.0モル）、触媒として三弗化ホウ
素エーテル錯体４ｇを仕込み、次にアリルグリシ
ジルエーテル228ｇ（2.0モル）を滴下し、80℃に
て５時間撹拌した後に120℃に加温し、減圧にて
過剰のアリルグリシジルエーテルを除去した。次
に得られた反応組成物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／cm2、温
度130℃の条件にて、プロピレンオキサイドを反
応組成物に対して５モル付加し、得られた組成物
を、製造例１に準じて硫酸化を行い、得られた硫
酸エステルアンモニウム塩を、本発明界面活性剤
〔Ｍ〕とした。
実施例 １
製造例１ないし７で得られた本発明の界面活性
剤〔Ａ〕〜〔Ｍ〕について、その水溶液の表面張
力を測定した。なお、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
ラウベ法にて測定した。）その結果を第１表に示
した。
実施例 ２
ポリプロピレンから作られた不織布（2.5cm×
10cm）を、第２表に示す界面活性剤の１％水溶液
に１分間浸漬し、取り出した後、120℃にて30分
間熱風乾燥を行つた。
上記界面活性剤処理した不織布を水50mlの入つ
た100ml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つた。（洗濯
後）その結果を第２表に示した。
Conventionally, surfactants have a wide range of properties such as emulsification, dispersion, cleaning, wetting, and foaming, and these properties have been used to improve materials such as fibers, paper, rubber, plastics, metals, and paints. It is used in various fields such as pigments, civil engineering and architecture. 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. For example, paints, printing inks, adhesives, pressure-sensitive adhesives, etc. are used during the manufacturing of the product, or during product stabilization.
Furthermore, it is indispensable in terms of workability and the like. When these products are used in applications such as coating, printing, adhesion, and adhesion, surfactants are not necessary; rather, the surfactants present are responsible for forming coatings, printed surfaces, and adhesive films. In many cases, performance such as water resistance and oil resistance may be deteriorated. As a countermeasure to these problems, efforts have been made to reduce the amount of surfactants blended and to use polymeric surfactants, but these problems have not yet been fully resolved in terms of product stability and workability. It's not working. On the other hand, in order to provide new types of surfactants, there are many patents for polymerizable, reactive, or degradable surfactants. For example, as an anionic surfactant,
No. 34894, Special Publication No. 56-29657, Japanese Patent Publication No. 51-30285
No. 49-46291, JP-A No. 56-127697, etc. As a nonionic surfactant, JP-A-56
-28208, JP-A-50-98484, etc. The present invention is based on the general formula [However, in the above formula, R is an alkyl group having 8 to 30 carbon atoms, an alkenyl group, an alkylaryl group, or an aralkylaryl group, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, and n is 0 to 100 , m is an integer from 1 to 200, and M is an alkali metal atom, NH 4 , or an alkanolamine residue. ] Provided is a fiber post-processing agent characterized by comprising a compound represented by the following. In the general formula, R is an alkyl group, alkenyl group, alkylaryl group, or aralkylaryl group having 8 to 30 carbon atoms, and examples of the alkyl group include octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, and tetradecyl. ,
Examples include pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, and the like. Examples of alkenyl groups include octenyl,
Examples include nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, and the like. Examples of the alkylaryl group include monobutylphenol, dibutylphenol, sec-butylphenol, disec-butylphenol, tert-butylphenol, octylphenol, nonylphenol, dinonylphenol, dodecylphenol, and didecylphenol. Examples of aralkyl phenols include mono-, di-, and tri-styrene phenols, benzyl phenols, cumyl phenols, and the like, or mixtures thereof, and may be mixtures of these alkyl groups. Further, A is an alkylene group or 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 is an integer of 0 to 100, m is an integer of 1 to 200, more preferably n is 0 or 1 to 50, m is 2
~100 range. Furthermore, the fiber post-processing agent of the present invention can be easily manufactured industrially, and can be manufactured, for example, as follows. That is, nonylphenol or lauryl alcohol is used as a raw material,
If necessary, alkylene oxide is added, allyl glycidyl ether is heated and reacted in the presence of a catalyst, and alkylene oxide is further added to the resulting reaction composition in a conventional manner. Next, sulfuric acid,
Perform sulfation with a sulfating agent such as sulfamic acid,
It can be obtained by neutralizing with a basic substance if necessary. EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto. (%, parts and parts are based on weight.) Production example 1 220g (1.0 mol) of nonylphenol and 1.5g of triethylamine as a catalyst were charged into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, and then allylglycidyl was added. Add 114 g (1.0 mol) of ether dropwise to 100
The mixture was stirred at ℃ for 5 hours. Next, the obtained reaction composition was transferred to an autoclave, and caustic potassium was used as a catalyst to
10 mol, 30 mol, and 100 mol of ethylene oxide were added to the reaction composition under conditions of cm 2 and temperature of 130° C. to obtain compositions. Next, 387 g (0.5 mol) of the 10 mol ethylene oxide adduct of the above reaction composition and 58.2 g (0.6 mol) of sulfamic acid were placed in a reaction vessel equipped with a stirrer and a thermometer, and the temperature was raised to 120°C. The reaction was stirred for a period of time and sulfation was carried out. The composition obtained by removing unreacted sulfamic acid by filtration was designated as the surfactant of the present invention [A]. The ammonium sulfate ester of an adduct of 30 moles of ethylene oxide obtained in the same manner was used as the surfactant of the present invention [B], and the ammonium sulfate of an adduct of 100 moles of ethylene oxide was used as the surfactant of the present invention [B]. C]. Production Example 2 Into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 186 g (1.0 mol) of lauryl alcohol and 0.6 g of boron trifluoride ether complex as a catalyst were charged, and then 228 g (2.0 mol) of allyl glycidyl ether was added dropwise. After stirring at 80°C for 5 hours, the mixture was heated to 120°C and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and caustic potassium was used as a catalyst to reduce pressure.
Ethylene oxide was added to the reaction composition at a rate of 1.5Kg/cm 2 and a temperature of 130°C at 5 moles, 20 moles, and 50 moles.
The composition obtained by the molar addition was sulfated according to Production Example 1, and the obtained sulfate ester ammonium salt of the 5 mol ethylene oxide adduct was added to the surfactant of the present invention [D] and 20 mol ethylene oxide. The ammonium sulfate ester salt of the adduct was designated as the surfactant of the present invention [E], and the ammonium sulfate ester salt of the 50 mole ethylene oxide adduct was designated as the surfactant of the present invention [F]. Production Example 3 In a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, add 10 moles of distyrenated phenol ethylene oxide and 2 moles of propylene oxide block adduct.
856 g (1.0 mol) and 2 g of boron trifluoride ether complex as a catalyst were added, and then 228 g (2.0 mol) of allyl glycidyl ether was added dropwise. After stirring at 80°C for 5 hours, the mixture was heated to 120°C and reduced pressure. Excess allyl glycidyl ether was removed. Next, the obtained reaction composition was transferred to an autoclave, and caustic potassium was used as a catalyst at a pressure of 1.5 Kg/cm 2 and a temperature of 130°C.
The composition obtained by adding 15 moles and 40 moles of ethylene oxide to the reaction composition under the conditions of The ester ammonium salt was used as the surfactant of the present invention [G], and the sulfuric acid ester ammonium salt of a 40 mol ethylene oxide adduct was used as the surfactant of the present invention [H]. Production Example 4 Into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 1588 g (1.0 mol) of 30 mol adduct of oleyl alcohol ethylene oxide and 3 g of boron trifluoride ether complex as a catalyst were charged, and then 228 g of allyl glycidyl ether ( 2.0 mol) was added dropwise and the mixture was heated at 80°C.
After stirring for an hour, the mixture was heated to 120°C and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and caustic potassium was used as a catalyst at a pressure of 1.5 Kg/cm 2 and a temperature of 130°C.
A composition obtained by randomly adding 40 moles of ethylene oxide and 10 moles of propylene oxide to the reaction composition at An equivalent amount of caustic soda to the sulfamic acid was added to the obtained sulfate to remove ammonia, and the obtained sulfate ester sodium salt was added to the surfactant of the present invention [I].
And so. Production Example 5 Into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 385 g (1.0 mol) of a 2-mol adduct of stearyl alcohol propylene oxide and 1.5 g of boron trifluoride ether complex as a catalyst were charged, followed by 228 g of allyl glycidyl ether. (2.0 mol) was added dropwise at 80℃.
After stirring for 5 hours, the mixture was heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure.
Next, the obtained reaction composition was transferred to an autoclave, and a pressure of 1.5 Kg/cm 2 was applied using caustic potassium as a catalyst.
The composition obtained by adding 2 moles and 5 moles of ethylene oxide at a temperature of 130 ° C. was sulfated using sulfamic acid according to Production Example 1.
Add sulfamic acid and equivalent amount of monoethanolamine to the obtained sulfate to remove ammonia,
The resulting sulfate ester monoethanolamine salt of the 2 mole ethylene oxide adduct was used as the surfactant of the present invention [J], and the sulfate monoethanolamine salt of the 5 mole ethylene oxide adduct was treated as the present invention surfactant [K]. And so. Production Example 6 A reaction vessel equipped with a stirrer, a thermometer, and a reflux tube was
278 g (1.0 mol) of sec-butylphenol butylene oxide 3 mol adduct and 1 g of boron trifluoride ether complex as a catalyst were charged, and then 228 g (2.0 mol) of allyl glycidyl ether was added dropwise to the mixture, and the mixture was heated at 80°C.
After stirring for 5 hours, the mixture was heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure.
Next, the obtained reaction composition was transferred to an autoclave, and a pressure of 1.5 Kg/cm 2 was applied using caustic potassium as a catalyst.
At a temperature of 130℃, propylene oxide 2
15 moles of ethylene oxide were added to the reaction composition, the resulting composition was sulfated according to Production Example 1, and the obtained sulfate ester ammonium salt was added to the surfactant of the present invention [L]. And so. Production Example 7 Into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 1244 g (1.0 mol) of a 20 mol adduct of tribenzylphenol ethylene oxide and 4 g of boron trifluoride ether complex as a catalyst were charged, and then 228 g of allyl glycidyl ether was charged. (2.0 mol) was added dropwise, and after stirring at 80°C for 5 hours, the mixture was heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave,
Using caustic potassium as a catalyst, 5 mol of propylene oxide was added to the reaction composition at a pressure of 1.5 Kg/cm 2 and a temperature of 130°C, and the resulting composition was sulfated according to Production Example 1. The sulfuric acid ester ammonium salt obtained was designated as the surfactant of the present invention [M]. Example 1 The surface tensions of aqueous solutions of the surfactants [A] to [M] of the present invention obtained in Production Examples 1 to 7 were measured. In addition, the surface tension of a conventional surfactant is also shown as a comparative product. (Surface tension was measured by the Traube method.) The results are shown in Table 1. Example 2 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 2, taken out, and then dried with hot air at 120° C. for 30 minutes. The nonwoven fabric treated with the surfactant was suspended over a 100 ml beaker containing 50 ml of water, and 1 cm from the bottom of the nonwoven fabric 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. The results (after washing) are shown in Table 2.
【表】【table】
【表】【table】
Claims (1)
基、アルケニル基、もしくはアルキルアリール
基、アラルキルアリール基、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
０〜100の整数であり、ｍ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
なることを特徴とする繊維後加工処理剤。[Claims] 1 General formula, [However, in the above formula, R is an alkyl group having 8 to 30 carbon atoms, an alkenyl group, an alkylaryl group, or an aralkylaryl group, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, and n is 0 to 100 , m is an integer from 1 to 200, and M is an alkali metal atom, NH 4 , or an alkanolamine residue. ] A fiber post-processing agent characterized by comprising a compound represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20869087A JPS63203872A (en) | 1987-08-21 | 1987-08-21 | Novel fiber post-processing treatment agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20869087A JPS63203872A (en) | 1987-08-21 | 1987-08-21 | Novel fiber post-processing treatment agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63203872A JPS63203872A (en) | 1988-08-23 |
| JPH042714B2 true JPH042714B2 (en) | 1992-01-20 |
Family
ID=16560460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20869087A Granted JPS63203872A (en) | 1987-08-21 | 1987-08-21 | Novel fiber post-processing treatment agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63203872A (en) |
-
1987
- 1987-08-21 JP JP20869087A patent/JPS63203872A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63203872A (en) | 1988-08-23 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |