JP2004182721A - フッ素系界面活性剤 - Google Patents
フッ素系界面活性剤 Download PDFInfo
- Publication number
- JP2004182721A JP2004182721A JP2003344323A JP2003344323A JP2004182721A JP 2004182721 A JP2004182721 A JP 2004182721A JP 2003344323 A JP2003344323 A JP 2003344323A JP 2003344323 A JP2003344323 A JP 2003344323A JP 2004182721 A JP2004182721 A JP 2004182721A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- compound
- materials
- general formula
- formula
- 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.)
- Granted
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 45
- 239000011737 fluorine Substances 0.000 title claims abstract description 42
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- -1 coatings Substances 0.000 claims abstract description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052744 lithium Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 150000002222 fluorine compounds Chemical class 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 7
- 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 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 32
- 239000003795 chemical substances by application Substances 0.000 abstract description 14
- 238000000576 coating method Methods 0.000 abstract description 13
- 239000011248 coating agent Substances 0.000 abstract description 12
- 239000000654 additive Substances 0.000 abstract description 11
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- 239000003599 detergent Substances 0.000 abstract description 2
- 150000002221 fluorine Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 230000000694 effects Effects 0.000 description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 150000003573 thiols Chemical class 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
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- 239000002904 solvent Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- GTPHVVCYEWPQFE-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-thiol Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCS GTPHVVCYEWPQFE-UHFFFAOYSA-N 0.000 description 5
- URJIJZCEKHSLHA-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecane-1-thiol Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCS URJIJZCEKHSLHA-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000012459 cleaning agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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Abstract
【解決手段】 1分子中に、F(CF2)2m(CH2)nS−(式中、m、nはそれぞれ同一または異なる1〜12の整数である。)と、−SO3M(式中、Mは水素原子、アンモニウムまたはアルカリ金属である。)を有するフッ素系化合物(A)からなることを特徴とするフッ素系界面活性剤。
【選択図】 なし
Description
本発明に係る界面活性効果としては、種々の界面活性効果、例えば、コーティング、モールディング用途における組成物の濡れ性、浸透性、はじき防止性、レベリング性、塗膜の均一性・均質性、表面改質性等が挙げられる。
F(CF2)2m(CH2)nSXSO3M (1)
(式中、m、nはそれぞれ同一または異なる1〜12の整数であり、Xは2価の連結基であり、Mは水素原子、アンモニウムまたはアルカリ金属である。)
で表されるフッ素系化合物が挙げられる。
−(CH2CH2O)p(CH2)q− (2)
(式中、pは0〜40の整数であり、qは3または4である。)
で表される基であることが好ましく、実用的な界面活性効果を有するフッ素系化合物が得られる点から前記一般式(2)中のpは0〜25の整数であることが好ましく、0〜15の整数であることが特に好ましい。また、前記一般式(2)中のqとしては原料の工業的入手および取り扱いが容易で製造時の安全性が高い点から4であることが好ましい。
F(CF2)2m(CH2)nSY (3)
[式中、m、nはそれぞれ同一または異なる1〜12の整数であり、Yは(CH2CH2O)pH(式中、pは0〜40の整数である。)である。]
で表される化合物(B)にスルトン化合物を反応させた後、中和して下記一般式(4)
F(CF2)2m(CH2)nS(CH2CH2O)p(CH2)qSO3M (4)
(式中、m、n、pは前記と同じであり、qは3または4であり、Mは水素原子、アンモニウムまたはアルカリ金属である。)
で表されるフッ素系化合物を製造する方法。
pが0の場合は、前記一般式(4)は、下記一般式(5)
F(CF2)2m(CH2)nS(CH2)qSO3M (5)
(式中、m、n、q、Mは前記と同じである。)
で表され、前記一般式(3)のYが水素原子であるチオール類にスルトン化合物を反応させた後、中和することで得ることができる。
この化合物は、前記一般式(3)中のYが水素原子であるチオール類に下記一般式(6)
Z(CH2CH2O)pH (6)
(式中、Zはハロゲン原子、pは1〜40の整数である。)
で表されるハロゲン化ポリオキシエチレンを反応させて下記一般式(7)
F(CF2)2m(CH2)nS(CH2CH2O)pH (7)
(式中、m、n、pは前記と同じである。)
で表される化合物とした後、スルトン化合物と反応させ、その後中和することで得ることができる。
前記一般式(6)で表されるハロゲン化ポリオキシエチレンとしては、式中のZとして、塩素原子、臭素原子、ヨウ素原子が挙げられ、反応性及び安定性の観点から、塩素原子、臭素原子が好ましく、また式中のpとしては、得られるフッ素系化合物に要求される疎水性、親水性のレベルに応じて適宜選択が可能である。
攪拌装置、還流冷却器および温度計を付した2リットルの四ツ口フラスコに、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ヘプタデカフルオロ−デカン−1−チオール480.2g(1mol)及び1,4−ブタンスルトン149.8g(1.1mol)を加え、窒素雰囲気下、120℃で4時間攪拌した。その後25℃に冷却し、反応液に10重量%水酸化リチウム水溶液460gを加えた。25℃で30分間攪拌した後、減圧下で水を留去した。得られた化合物をメタノールから再結晶することにより、フッ素系化合物(i)[4−(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-ヘプタデカフルオロデカンスルファニル)−ブタン−1−スルホン酸リチウム]529gを得た。
実施例1において、10重量%水酸化リチウム水溶液460gの代わりに、10重量%水酸化ナトリウム水溶液440gを用いる以外は実施例1と同様にして、フッ素系化合(ii)[4−(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-ヘプタデカフルオロデカンスルファニル)−ブタン−1−スルホン酸ナトリウム]574.6gを得た。
実施例1において、10重量%水酸化リチウム水溶液460gの代わりに、10重量%水酸化カリウム水溶液617gを用いる以外は実施例1と同様にして、フッ素系化合物(iii)[4−(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-ヘプタデカフルオロデカンスルファニル)−ブタン−1−スルホン酸カリウム]576gを得た。
実施例1において、10重量%水酸化リチウム水溶液460gの代わりに、25重量%アンモニア水溶液74.8g及びイオン交換水400gを用いる以外は実施例1と同様にして、フッ素系化合物(iv)[4−(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-ヘプタデカフルオロデカンスルファニル)−ブタン−1−スルホン酸アンモニウム]570gを得た。
実施例1において、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ヘプタデカフルオロ−デカン−1−チオール480.2g(1mol)の代わりに、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−オクタン−1−チオール380.2g(1mol)を用いる以外は実施例1と同様にして、フッ素系化合物(v)[4−(3,3,4,4,5,5,6,6,7,7,8,8,8-トリデカフルオロオクタンスルファニル)−ブタン−1−スルホン酸リチウム]550gを得た。
実施例1において、1,4−ブタンスルトン149.8g(1.1mol)の代わりに、1,3−プロパンスルトン134.4g(1.1mol)を用いる以外は実施例1と同様にして、フッ素系化合物(vi)[3−(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-ヘプタデカフルオロデカンスルファニル)−プロパン−1−スルホン酸リチウム]525gを得た。
攪拌装置、還流冷却器および温度計を付した2リットルの四ツ口フラスコに、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ヘプタデカフルオロ−デカン−1−チオール480.2g(1mol)及びクロロポリオキシエチレン(エチレンオキサイドの付加モル数:平均10モル)524.7gを加え、窒素雰囲気下、80℃で8時間攪拌した。その後、1,4−ブタンスルトン149.8g(1.1mol)を加えた後、窒素雰囲気下、120℃で4時間攪拌した。25℃に冷却した後、反応液に10重量%水酸化リチウム水溶液460gを加えた。25℃で30分間攪拌した後、減圧下で水を留去した。得られた化合物をメタノールから再結晶することにより、フッ素系化合物(vii)[4−{(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-ヘプタデカフルオロデカンスルファニル)−ポリオキシエチレン}−ブタン−1−スルホン酸リチウム]903gを得た。
実施例7において、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ヘプタデカフルオロ−デカン−1−チオール480.2g(1mol)の代わりに、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−オクタン−1−チオール380.2g(1mol)を用いる以外は実施例1と同様にして、フッ素系化合物(viii)[4−{(3,3,4,4,5,5,6,6,7,7,8,8,8-トリデカフルオロオクタンスルファニル)−ポリオキシエチレン}−ブタン−1−スルホン酸リチウム]870gを得た。
実施例7において、クロロポリオキシエチレン(エチレンオキサイドの付加モル数:平均10モル)524.7gの代わりに、クロロポリオキシエチレン(エチレンオキサイドの付加モル数:平均15モル)766.9gを用いる以外は実施例7と同様にして、フッ素系化合物(ix)[4−{(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-ヘプタデカフルオロデカンスルファニル)−ポリオキシエチレン}−ブタン−1−スルホン酸リチウム]1134gを得た。
実施例7において、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ヘプタデカフルオロ−デカン−1−チオール480.2g(1mol)の代わりに、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−オクタン−1−チオール380.2g(1mol)を用い、更に、クロロポリオキシエチレン(エチレンオキサイドの付加モル数:平均10モル)524.7gの代わりに、クロロポリオキシエチレン(エチレンオキサイドの付加モル数:平均15モル)766.9gを用いる以外は実施例7と同様にして、フッ素系化合物(x)[4−{(3,3,4,4,5,5,6,6,7,7,8,8,8-トリデカフルオロオクタンスルファニル)−ポリオキシエチレン}−ブタン−1−スルホン酸リチウム]989gを得た。
実施例1〜10で得られたフッ素系化合物からなるフッ素系界面活性剤の水溶液での表面張力を以下の方法で測定し試験例1〜10として表1に示す。
表面張力:自動表面張力計CBPV−Z(協和界面化学株式会社製)を用いて、ウィルヘルミー白金プレート法にて、20℃における各濃度(イオン交換水溶液、重量%)での表面張力を測定した。(単位:mN/m)
実施例7で得られたフッ素系化合物(vii)を用いて、炭化水素系界面活性剤との併用効果を確認した。フッ素系化合物(vii)と炭化水素系界面活性剤(ポリオキシエチレンオレイルエーテル:花王株式会社製エマルゲン430)との混合物の0.001重量%水溶液における表面張力を測定し、試験例11、12として結果を表2に示す。
Claims (7)
- 1分子中に、F(CF2)2m(CH2)nS−(式中、m、nはそれぞれ同一または異なる1〜12の整数である。)と、−SO3M(式中、Mは水素原子、アンモニウムまたはアルカリ金属である。)を有するフッ素系化合物(A)からなることを特徴とするフッ素系界面活性剤。
- フッ素系化合物(A)が、下記一般式(1)
F(CF2)2m(CH2)nSXSO3M (1)
(式中、m、nはそれぞれ同一または異なる1〜12の整数であり、Xは2価の連結基であり、Mは水素原子、アンモニウムまたはアルカリ金属である。)
で表されるフッ素系化合物である請求項1記載のフッ素系界面活性剤。 - 前記一般式(1)中のXが下記一般式(2)
−(CH2CH2O)p(CH2)q− (2)
(式中、pは0〜40の整数であり、qは3または4である。)
で表される基である請求項2記載のフッ素系界面活性剤。 - フッ素系化合物(A)が、下記一般式(3)
F(CF2)2m(CH2)nSY (3)
[式中、m、nは前記と同じであり、Yは(CH2CH2O)pH(式中、pは前記と同じである。)である。]
で表される化合物(B)にスルトン化合物を反応させた後、中和して得られる下記一般式(4)
F(CF2)2m(CH2)nS(CH2CH2O)p(CH2)qSO3M (4)
(式中、m、n、p、q、Mは前記と同じである。)
で表されるフッ素系化合物である請求項2記載のフッ素系界面活性剤。 - 前記一般式(1)中のmが3または4であり、nが2〜4の整数であり、MがNH4、リチウム、ナトリウムまたはカリウムである請求項2記載のフッ素系界面活性剤。
- 前記一般式(2)中のpが0〜15の整数である請求項3記載のフッ素系界面活性剤。
- 前記一般式(4)中のmが3または4であり、nが2〜4の整数であり、pが0〜15の整数であり、MがNH4、リチウム、ナトリウムまたはカリウムである請求項4記載のフッ素系界面活性剤。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2246324A1 (en) * | 2009-04-21 | 2010-11-03 | Maflon S.R.L. | Sulphonic function fluorine compounds and their use |
JP2011020924A (ja) * | 2009-07-13 | 2011-02-03 | Kri Inc | フッ素化合物及びその製造方法 |
JP2011144122A (ja) * | 2010-01-13 | 2011-07-28 | Agc Seimi Chemical Co Ltd | 含フッ素化合物、含フッ素界面活性剤およびその組成物 |
US20170071059A1 (en) * | 2014-06-03 | 2017-03-09 | Mitsui Mining & Smelting Co., Ltd. | Metal foil with releasing resin layer, and printed wiring board |
-
2003
- 2003-10-02 JP JP2003344323A patent/JP4411515B2/ja not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2246324A1 (en) * | 2009-04-21 | 2010-11-03 | Maflon S.R.L. | Sulphonic function fluorine compounds and their use |
JP2011020924A (ja) * | 2009-07-13 | 2011-02-03 | Kri Inc | フッ素化合物及びその製造方法 |
JP2011144122A (ja) * | 2010-01-13 | 2011-07-28 | Agc Seimi Chemical Co Ltd | 含フッ素化合物、含フッ素界面活性剤およびその組成物 |
US20170071059A1 (en) * | 2014-06-03 | 2017-03-09 | Mitsui Mining & Smelting Co., Ltd. | Metal foil with releasing resin layer, and printed wiring board |
US10863621B2 (en) * | 2014-06-03 | 2020-12-08 | Mitsui Mining & Smelting Co., Ltd. | Metal foil with releasing resin layer, and printed wiring board |
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JP4411515B2 (ja) | 2010-02-10 |
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