JP2006249130A - フッ素化アルキル基含有オリゴマーの製造方法 - Google Patents
フッ素化アルキル基含有オリゴマーの製造方法 Download PDFInfo
- Publication number
- JP2006249130A JP2006249130A JP2005063740A JP2005063740A JP2006249130A JP 2006249130 A JP2006249130 A JP 2006249130A JP 2005063740 A JP2005063740 A JP 2005063740A JP 2005063740 A JP2005063740 A JP 2005063740A JP 2006249130 A JP2006249130 A JP 2006249130A
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- Prior art keywords
- polymerization
- alkyl group
- oligomer
- fluorinated alkyl
- monomer
- 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
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- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 57
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 89
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 44
- 150000001451 organic peroxides Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 abstract description 42
- 238000000034 method Methods 0.000 abstract description 23
- 239000012986 chain transfer agent Substances 0.000 abstract description 8
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 65
- -1 thiol compounds Chemical class 0.000 description 43
- 229910052731 fluorine Inorganic materials 0.000 description 26
- 239000000243 solution Substances 0.000 description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 18
- 239000011737 fluorine Substances 0.000 description 18
- 239000004094 surface-active agent Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 125000001153 fluoro group Chemical group F* 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
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- 229920000728 polyester Polymers 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000009965 odorless effect Effects 0.000 description 5
- 238000006276 transfer reaction Methods 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical class CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007877 V-601 Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- 238000012719 thermal polymerization Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical class COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical class O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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- TXHZNLCKXHJYNX-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOC(=O)C(C)=C TXHZNLCKXHJYNX-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】 フッ素化アルキル基含有エチレン性不飽和単量体(A)を含有するエチレン性不飽和単量体類(I)中のエチレン性不飽和基1モルに対して、重合開始剤(C)を0.07〜0.70モル用いて前記単量体類(I)を重合してフッ素化アルキル基含有オリゴマーを得ることを特徴とするフッ素化アルキル基含有オリゴマーの製造方法。
【選択図】 なし
Description
本発明において、フッ素化アルキル基とはアルキル基中の全ての水素原子がフッ素原子に置換されたもの(パーフルオロアルキル基)と、アルキル基中の一部の水素原子がフッ素原子で置換されたもの〔例えば、−(CF2)6H等〕との総称であり、直鎖状でも分岐状であっても良い。更に、該フッ素化アルキル基中に酸素原子を含むもの〔例えば−OCF2CF2(OCF(CF3)CF2)2CF2CF3、−(OCF2CF2)8−等〕も本定義中に含めるものとする。
CH2=C(R1)COO(X)aRf (1)
(式中、R1は水素原子、メチル基、塩素原子、フッ素原子又はシアノ基であり、Xはフッ素原子を含まない2価の連結基であり、aは0または1の整数であり、Rfはフッ素化アルキル基である。)
にて表される単量体であることが好ましい。
A−1 :CH2=CHCOOCH2CH2C8F17
A−2 :CH2=C(CH3)COOCH2CH2C8F17
A−3 :CH2=CHCOOCH2CH2C12F25
A−4 :CH2=CHCOOCH2CH2C6F13
A−5 :CH2=CHCOOCH2CH2C4F9
A−6 :CH2=CFCOOCH2CH2C6F13
A−7 :CH2=CHCOOCH2CF3
A−8 :CH2=C(CH3)COOCH2CF(CF3)2
A−9 :CH2=C(CH3)COOCH2CFHCF3
A−10:CH2=CHCOOCH2(CF2)6H
A−11:CH2=CHCOOCH2CH(OH)CH2C8F17
A−12:CH2=CHCOOCH2CH2N(C3H7)SO2C8F17
A−13:CH2=CHCOOCH2CH2N(C2H5)COC7F15
A−14:CH2=CHCOOC2H4(CF(CF3)OCF2)3C2F5
A−15:CH2=CHCOOCH2(CF(CF3)OCF2)2C2F5
尚、本発明がこれら具体例によって何等限定されるものでないことは勿論である。また、フッ素化アルキル基含有エチレン性不飽和単量体(A)は、1種類であっても良いし、構造が異なる2種類以上の化合物の混合物であっても良い。
撹拌装置、コンデンサー、温度計、滴下ロートを備えたガラスフラスコに重合溶媒としてメチルイソブチルケトンを250g仕込む。一方、フッ素化アルキル基含有エチレン性不飽和単量体(A)としてA−4を40g(0.0957モル)、(A)以外のエチレン性不飽和単量体(B)として平均重合度4.5モルのポリエチレンオキシド鎖含有アクリレート(日本油脂株式会社製ブレンマーAE−200)を40g(0.1481モル)、2−ヒドロキシエチルアクリレートを20g(0.1724モル)、重合開始剤(C)としてt−ブチルパーオキシ−2―エチルヘキサノエート(日本油脂株式会社製パーブチルO、以下パーブチルOと略す。10時間半減期温度;72.1℃)を20g(0.0926モル)そしてメチルイソブチルケトン50重量部を予め混合し均一に溶解させ、滴下ロートに仕込み滴下液とする。
実施例1における滴下液中の単量体組成を、A−4を40g(0.0957モル)、平均重合度9モルで末端がメトキシ基であるポリエチレンオキシド鎖含有メタアクリレート(新中村化学株式会社製NKエステル M−90G)を60g(0.1210モル)とした以外は実施例1と同様に重合反応を行い、ほぼ無臭の含フッ素オリゴマー(オリゴマー2とする。)を得た。オリゴマー2の数平均分子量はMn=1,400平均重合度は2.5であった。オリゴマー2の1%水溶液は、沈殿は生じず僅かに濁る分散液体であった。オリゴマー2の0.1wt%水溶液のウィルヘルミー法にて測定した表面張力は20.8mN/mであり、低濃度で優れた表面張力低下能力を示した。
実施例1における滴下液中の単量体組成を、A−1を60g(0.0965モル)、平均重合度5モルのポリプロピレンオキシド鎖含有メタクリレート(日本油脂株式会社製ブレンマーPP−1000、以下PP−1000と略す。)を40g(0.1064モル)、パーブチルOを7.5g(0.0347モル)とした以外は実施例1と同様に重合反応を行い、ほぼ無臭の含フッ素オリゴマー(オリゴマー3)を得た。オリゴマー3の数平均分子量はMn=2,100であり、平均重合度は4.7であった。オリゴマー3の1%IPA溶液および1%プロピレングリコールモノメチルエーテル(PGME)溶液は透明な液体であった。オリゴマー3の0.1%PGME溶液のウィルヘルミー法により測定した表面張力は17.7mN/mであり、低濃度で優れた表面張力低下能力を示した。
実施例1における滴下液中の重合開始剤(C)としてジメチル2,2’−アゾビス(2−メチルプロピオネート)(和光純薬株式会社製V−601、10時間半減期温度;66℃)を20g(0.087モル)とした以外は実施例1と同様に重合反応を行い、ほぼ無臭の含フッ素オリゴマー(オリゴマー4とする。)を得た。オリゴマー4の数平均分子量はMn=910平均重合度は2.3であった。オリゴマー4の1%水溶液は、透明な液体であった。オリゴマー4の0.1wt%水溶液のウィルヘルミー法にて測定した表面張力は19.7mN/mであり、低濃度で優れた表面張力低下能力を示した。
実施例1における滴下液中のパーブチルOを2g(0.0093モル)とし、重合温度を80℃とした以外は実施例1と同様に重合反応を行い、ほぼ無臭の含フッ素オリゴマー(オリゴマー5)を得た。オリゴマー5の数平均分子量はMn=6,100であり、平均重合度は19.7であった。オリゴマー5の1%水溶液は白濁した。
実施例1における滴下液中のパーブチルOを2g(0.0093モル)、連鎖移動剤としてn−ラウリルメルカプタンを3g(0.0149モル)とした以外は実施例1と同様に重合反応を行い、含フッ素オリゴマー(オリゴマー6)を得た。オリゴマー6はn−ラウリルメルカプタン由来の強い特異臭を有していた。オリゴマー6の数平均分子量はMn=960であり、平均重合度は2.5であった。
実施例3における滴下液中のパーブチルOを3重量部(0.0139モル)とし、重合温度を80℃とした以外は実施例1と同様に重合反応を行い、ほぼ無臭の含フッ素オリゴマー(オリゴマー7)を得た。オリゴマー7の数平均分子量はMn=8,400であり、平均重合度は20.4であった。オリゴマー7は1%IPA溶液および1%プロピレングリコーロモノメチルエーテル溶液に溶解しなかった。
Claims (5)
- フッ素化アルキル基含有エチレン性不飽和単量体(A)を含有するエチレン性不飽和単量体類(I)中のエチレン性不飽和基1モルに対して、重合開始剤(C)を0.07〜0.7モル用いて前記単量体類(I)を重合してフッ素化アルキル基含有オリゴマーを得ることを特徴とするフッ素化アルキル基含有オリゴマーの製造方法。
- 単量体類(I)中にマクロモノマーであるエチレン性不飽和単量体(B)を含有する請求項1記載のフッ素化アルキル基含有オリゴマーの製造方法。
- マクロモノマーであるエチレン性不飽和単量体(B)が、ポリオキシアルキレン構造を有するエチレン性不飽和単量体(b1)である請求項2記載のフッ素化アルキル基含有オリゴマーの製造方法。
- 重合開始剤(C)が10時間半減期温度が40〜120℃の有機過酸化物(c1)である請求項1〜3の何れか1項記載のフッ素化アルキル基含有オリゴマーの製造方法。
- フッ素化アルキル基含有エチレン性不飽和単量体(A)を含有するエチレン性不飽和単量体類(I)中のエチレン性不飽和基1モルに対して、重合開始剤(C)を0.15〜0.5モル用いる請求項4記載のフッ素化アルキル基含有オリゴマーの製造方法。
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11130819A (ja) * | 1997-10-27 | 1999-05-18 | Denki Kagaku Kogyo Kk | 硬化性樹脂組成物及び常温硬化型アクリル系被覆材 |
JP2002517530A (ja) * | 1998-06-03 | 2002-06-18 | アトフィナ | 親水性フルオロポリマー |
JP2002327003A (ja) * | 2001-04-27 | 2002-11-15 | Kao Corp | フッ化アルキル基含有重合体の製造方法および製造装置 |
WO2004018535A1 (ja) * | 2002-08-22 | 2004-03-04 | Seimi Chemical Co., Ltd. | フッ素系界面活性剤 |
-
2005
- 2005-03-08 JP JP2005063740A patent/JP4997708B2/ja active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11130819A (ja) * | 1997-10-27 | 1999-05-18 | Denki Kagaku Kogyo Kk | 硬化性樹脂組成物及び常温硬化型アクリル系被覆材 |
JP2002517530A (ja) * | 1998-06-03 | 2002-06-18 | アトフィナ | 親水性フルオロポリマー |
JP2002327003A (ja) * | 2001-04-27 | 2002-11-15 | Kao Corp | フッ化アルキル基含有重合体の製造方法および製造装置 |
WO2004018535A1 (ja) * | 2002-08-22 | 2004-03-04 | Seimi Chemical Co., Ltd. | フッ素系界面活性剤 |
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JP2011074129A (ja) * | 2009-09-29 | 2011-04-14 | Neos Co Ltd | 撥水撥油組成物 |
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