JP2008137973A5 - - Google Patents
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- JP2008137973A5 JP2008137973A5 JP2006327769A JP2006327769A JP2008137973A5 JP 2008137973 A5 JP2008137973 A5 JP 2008137973A5 JP 2006327769 A JP2006327769 A JP 2006327769A JP 2006327769 A JP2006327769 A JP 2006327769A JP 2008137973 A5 JP2008137973 A5 JP 2008137973A5
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- JP
- Japan
- Prior art keywords
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- containing compound
- polymerizable functional
- hydroxyl group
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000010702 perfluoropolyether Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001983 dialkylethers Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- -1 methacryloyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Description
特許文献2には、酸ハライドに直接アルコールを反応させるという１段階の反応によって得られる、1分子中に2個以上の重合性官能基R 1 を有する含フッ素ポリエーテルカルボン酸エステルとして、一般式
R1OCOCF(CF3)[OCF2CF(CF3)]aO(CF2)bO[CF(CF3)CF2O]cCF(CF3)COOR1
で表わされる含フッ素ポリエーテルカルボン酸エステルが、本出願人によって開示されている。
R 1 OCOCF (CF 3 ) [OCF 2 CF (CF 3 )] a O (CF 2 ) b O [CF (CF 3 ) CF 2 O] c CF (CF 3 ) COOR 1
The fluorine-containing polyether carboxylic acid ester represented by this is disclosed by the present applicant.
この反応の主たる原料物質として用いられるパーフルオロポリエーテルジカルボン酸ジハライドにおいて、ハライド基Xとしては原料合成の容易さからフッ素原子であることが好ましく、またbの値は原料入手の容易さから2〜6であることが好ましい。さらに、a+cの値は28以下が好ましく、製造の容易さからは20以下であることが特に好ましい。a+cの値の調節は、一般的には対応するパーフルオロアルキルジカルボン酸ジフロライドに触媒の存在下でヘキサフルオロプロペンオキシドを反応させ、分布の生じたパーフルオロポリエーテル化合物を蒸留し、希望するa+cの値を有するジカルボン酸ジハライドを取得することによって行われる。 In the perfluoropolyether dicarboxylic acid dihalide used as the main raw material for this reaction, the halide group X is preferably a fluorine atom because of the ease of raw material synthesis, and the value of b is from 2 to 6 is preferred. Further, the value of a + c is preferably 28 or less, and particularly preferably 20 or less for ease of production. Adjustment of the value of a + c is generally achieved by reacting the corresponding perfluoroalkyldicarboxylic acid difluoride with hexafluoropropene oxide in the presence of a catalyst, distilling the perfluoropolyether compound in which the distribution has occurred, as desired. This is done by obtaining a dicarboxylic acid dihalide having a value of a + c.
このようなパーフルオロポリエーテルジカルボン酸ジハライドと順次等モルの割合で反応する水酸基含有化合物基は、まずエーテル基を有し得るフルオロアルキル基を有する水酸基含有化合物より嵩高い構造の重合性官能基を有する水酸基含有化合物が反応に供せられる。かかる水酸基含有化合物に含有される重合性官能基としては、ビニル基、アリル基、アクリロイル基、メタクリロイル基等の不飽和二重結合基またはグリシジル基によって代表されるエポキシアルキル基等のエポキシ基などの重合性官能基である。より好ましくは、次のような基が例示される。
CH2=CRCOO(CH2)dCH2-
(CH2=CRCOOCH2)2CH-
(CH2=CRCOOCH2)3CCH2-
R：水素原子またはメチル基
d：1〜3の整数
これらの例示された基において、(CH2=CRCOOCH2)基を2個または3個有する場合には、R基は必ずしも同一である必要はなく、例えば2個の場合
(CH2=CHCOOCH2)〔CH2=C(CH3)COOCH2〕CH-
としても用いられる。
Such perfluoropolyether dicarboxylic acid hydroxyl group-containing compound groups reactive sequentially at a ratio of equimolar and dihalide is first polymerizable functional groups of bulky structure than a hydroxyl group-containing compound having a fluoroalkyl group which may have an ether group A hydroxyl group-containing compound is provided for the reaction. Examples of the polymerizable functional group contained in the hydroxyl group-containing compound include an epoxy group such as an epoxy group represented by an unsaturated double bond group such as a vinyl group, an allyl group, an acryloyl group, and a methacryloyl group, or a glycidyl group. It is a polymerizable functional group. More preferably, the following groups are exemplified.
CH 2 = CRCOO (CH 2 ) d CH 2-
(CH 2 = CRCOOCH 2 ) 2 CH-
(CH 2 = CRCOOCH 2 ) 3 CCH 2-
R: hydrogen atom or methyl group
d: an integer of 1 to 3 In these exemplified groups, when two or three (CH 2 = CRCOOCH 2 ) groups are present, the R groups do not necessarily have to be the same, for example , in the case of two
(CH 2 = CHCOOCH 2 ) [CH 2 = C (CH 3 ) COOCH 2 ] CH-
Also used as
このようにしてジカルボン酸ジハライドの一方の末端基に重合性官能基を有するエステル基を導入した後、他方のカルボン酸ハライド基より嵩高ではない構造を有する、エーテル基を有し得るフルオロアルキル基を有する水酸基含有化合物との反応が行われる。この反応は、例えば約-40〜20℃、好ましくは約-10〜10℃の反応温度で行われ、他方の末端基としてエーテル基を有し得るフルオロアルキル基を有するエステル基が導入される。 In this way, after introducing an ester group having a polymerizable functional group into one terminal group of the dicarboxylic acid dihalide, a fluoroalkyl group having an ether group having a structure that is less bulky than the other carboxylic acid halide group is formed. The reaction with the hydroxyl group-containing compound is carried out. This reaction is carried out, for example, at a reaction temperature of about −40 to 20 ° C., preferably about −10 to 10 ° C., and an ester group having a fluoroalkyl group which can have an ether group as the other end group is introduced.
これら2段階の反応の反応溶媒としては、この反応に不活性なものであれば任意のものを使用し得るが、一般にはジアルキルエーテル、好ましくは沸点が低く、除去の容易なジエチルエーテル、ジイソプロピルエーテル、テトラヒドロフラン等が用いられる。さらに、C2F5CHCl2-CClF2CF2CHClF混合物(HCFC225)等の含フッ素系溶媒も好んで用いられる。 As the reaction solvent for these two-stage reactions, any solvent can be used as long as it is inert to this reaction. Generally, it is a dialkyl ether, preferably diethyl ether or diisopropyl ether having a low boiling point and easy to remove. , Tetrahydrofuran and the like are used. Furthermore, a fluorine-containing solvent such as a C 2 F 5 CHCl 2 —CClF 2 CF 2 CHClF mixture (HCFC225) is also preferably used.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006327769A JP2008137973A (en) | 2006-12-05 | 2006-12-05 | Fluorine-containing polyether carboxylic acid ester and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006327769A JP2008137973A (en) | 2006-12-05 | 2006-12-05 | Fluorine-containing polyether carboxylic acid ester and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008137973A JP2008137973A (en) | 2008-06-19 |
| JP2008137973A5 true JP2008137973A5 (en) | 2010-10-14 |
Family
ID=39599822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006327769A Withdrawn JP2008137973A (en) | 2006-12-05 | 2006-12-05 | Fluorine-containing polyether carboxylic acid ester and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2008137973A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102018008967A1 (en) * | 2018-08-21 | 2020-02-27 | Carl Zeiss Microscopy Gmbh | Chemical compounds and immersion mixtures |
-
2006
- 2006-12-05 JP JP2006327769A patent/JP2008137973A/en not_active Withdrawn
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