JP4781119B2 - 新規界面活性剤 - Google Patents
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- JP4781119B2 JP4781119B2 JP2006026204A JP2006026204A JP4781119B2 JP 4781119 B2 JP4781119 B2 JP 4781119B2 JP 2006026204 A JP2006026204 A JP 2006026204A JP 2006026204 A JP2006026204 A JP 2006026204A JP 4781119 B2 JP4781119 B2 JP 4781119B2
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- 239000004094 surface-active agent Substances 0.000 title claims description 43
- 238000012545 processing Methods 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 229910001868 water Inorganic materials 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000003599 detergent Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003921 oil Substances 0.000 description 39
- -1 halogen ions Chemical class 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 13
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 229910052742 iron Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 239000012964 benzotriazole Substances 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000002265 prevention Effects 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012459 cleaning agent Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000005520 cutting process Methods 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- 239000010687 lubricating oil Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 description 6
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000003254 anti-foaming effect Effects 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 150000004665 fatty acids Chemical group 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229920001983 poloxamer Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 3
- 229910001018 Cast iron Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229920002873 Polyethylenimine Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002359 Tetronic® Polymers 0.000 description 3
- 230000004931 aggregating effect Effects 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000008394 flocculating agent Substances 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- 229940043276 diisopropanolamine Drugs 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000010720 hydraulic oil Substances 0.000 description 2
- 239000002440 industrial waste Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LDTRLQFRPHFLGA-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;decanedioic acid Chemical compound OCCN(CCO)CCO.OC(=O)CCCCCCCCC(O)=O LDTRLQFRPHFLGA-UHFFFAOYSA-N 0.000 description 1
- 241001574381 Bactra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Lubricants (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
Description
1)研削加工、特に平面研削の場合
2)切粉分離のために遠心分離方式、スピクロン方式が採用されている場合
また、水溶性洗浄剤をスプレー方式で用いる場合も同様の問題が発生しやすい。
項1.下記一般式(1)で表される新規界面活性剤。
項3.項1記載の新規界面活性剤を含有する水溶性加工油剤。
項4.項1記載の新規界面活性剤を含有する水溶性洗浄剤。
項5.項1記載の新規界面活性剤を含有する水処理剤。
メタノール40mlを100mlビーカーに入れ、水酸化カリウム(純度86%)3.4gを加え溶解し、25℃になるまで放冷した。次いで、ベンゾトリアゾール7.3gを加え、撹拌しながら25℃になるまで放冷した。その後、下記の一般式(2)[ポリエチレンポリアミンとジクロロエチルエーテルとの共重合物の4級化物(分子量:約1500、塩素含有量:25重量%)]10.0gを加え10分間撹拌した。25℃まで冷却後、懸濁液をG4のグラスフィルターで濾過し、塩化カリウムの沈殿を分離した。ろ液のメタノールをロータリーエバポレーターを用いて減圧留去することによって、淡黄色透明ペースト状生成物11.8gを得た。この生成物をNMRで分析した。その結果を表1に示す。生成物中の下記一般式(3)の本発明の新規界面活性剤の含有量は約70重量%であった。他の成分としては、水、1,2,3−ベンゾトリアゾール、水酸化カリウム、塩化カリウムが確認された。
表2に示す配合処方により水溶性加工油剤1〜5を調製した。これらの水溶性加工油剤の油分離性、防錆性、消泡性および鉄イオン溶出の抑制性を以下の方法によって調べ、その結果を表2に示した。なお、表2中、配合量は重量%で示した。
共栓付きメスシリンダー(100ml)内に試験試料の10重量%水溶液50mlおよび「モービルバクトラオイルNo.2」(モービル株式会社製の摺動面潤滑油)5mlを入れ、密栓し、室温下で上下に10回激しく浸盪させた後静置し、該潤滑油の経時的な分離状態を目視で確認した。評価基準は次の通りである。
◎:潤滑油は静置後直ちに浮上し、油剤部分は透明である。
×:潤滑油は静置後浮上するが油剤部分は白濁する、あるいは潤滑油が分離しない。
シャーレ(直径:40mm)内に試験試料の10重量%水溶液約20mlを入れ、該水溶液中に鋳鉄(FC250)をドライカットすることで得られた切屑(8〜12メッシュ)5gを10分間浸漬させた後、該水溶液を排出し、該シャーレを恒温恒湿機(温度:30℃、湿度80%)内に放置し、シャーレ内の鋳鉄切屑の経時的な発錆状態を目視で観察した。評価基準は次の通りである。
◎:24時間経過後でも発錆は無い。
×:24時間以内に発錆する。
共栓付きメスシリンダー(100ml)内に試験試料の10重量%水溶液50ml(温度:25℃)を入れ、密栓し、上下に10回激しく浸盪させた後静置し、経時的な消泡状態を目視で確認した。評価基準は次の通りである。
◎:静置後1分未満に泡が消える。
○:静置後1〜5分未満の間で泡が消える。
△:静置後5〜10分未満の間で泡が消える。
×:静置後消泡に10分以上要する。
100ml蓋付きサンプル瓶に試験試料の10重量%水溶液50mlおよび鋳鉄(FC250)をドライカットすることで得られた切屑(8〜12メッシュ)5gを入れ、該サンプル瓶を恒温機(40℃)内に1週間放置した後、該水溶液中の鉄イオンの濃度を原子吸光光度計によって測定し、予め作成しておいた定量線からその濃度を求めた。
本発明の新規界面活性剤の調製方法に従い、下記一般式(4)および(5)で表される化合物を調製した。そして、以下の表3に示す配合処方により、水溶性加工油剤1〜9を調製し、これらの水溶性加工油剤の油分離性、防錆性、消泡性および鉄イオン溶出の抑制性を上記の実施例に記載の方法に従って調べ、その結果を表3に示した。なお、ポリエチレンイミンは油分離を目的として使用されており、比較例ではBASFジャパン社製のルガルバンG35を用いた。また、表3中、配合量は重量%で示した。
以下の成分を配合して常法により凝集剤を調製した。
実施例1の生成物 10重量%
ベンゾイソチアゾリン 1重量%
水 89重量%
以下の成分を配合して常法により水溶性洗浄剤を調製した。
実施例1の生成物 5重量%
トリエタノールアミン 30重量%
セバシン酸 5重量%
ポリオキシエチレンポリオキシプロピレンデシルエーテル 5重量%
(分子量700、EO/PO=80/20)
ベンゾイソチアゾリン 1重量%
水 54重量%
以下の成分を配合して常法により水処理剤を調製した。
実施例1の生成物 30重量%
水 70重量%
Claims (5)
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JP2006026204A JP4781119B2 (ja) | 2006-02-02 | 2006-02-02 | 新規界面活性剤 |
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JP2006026204A JP4781119B2 (ja) | 2006-02-02 | 2006-02-02 | 新規界面活性剤 |
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JP2007204647A JP2007204647A (ja) | 2007-08-16 |
JP4781119B2 true JP4781119B2 (ja) | 2011-09-28 |
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Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5072472B2 (ja) * | 2007-08-03 | 2012-11-14 | 株式会社ネオス | 中級カルボン酸残基を対イオンとする第4級アンモニウム塩の製造方法 |
JP2012062353A (ja) | 2010-09-14 | 2012-03-29 | Idemitsu Kosan Co Ltd | 水性洗浄剤 |
JP2013133458A (ja) * | 2011-12-27 | 2013-07-08 | Idemitsu Kosan Co Ltd | 水性洗浄剤 |
JP5972005B2 (ja) * | 2012-03-28 | 2016-08-17 | 株式会社ネオス | 水溶性消泡剤および低泡性加工油剤 |
JP7468847B2 (ja) | 2020-09-24 | 2024-04-16 | 株式会社片山化学工業研究所 | 廃水処理方法 |
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