WO2007105633A1 - ポリフルオロアルキルアルコールまたはその(メタ)アクリル酸誘導体およびそれらの製造法 - Google Patents
ポリフルオロアルキルアルコールまたはその(メタ)アクリル酸誘導体およびそれらの製造法 Download PDFInfo
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- WO2007105633A1 WO2007105633A1 PCT/JP2007/054678 JP2007054678W WO2007105633A1 WO 2007105633 A1 WO2007105633 A1 WO 2007105633A1 JP 2007054678 W JP2007054678 W JP 2007054678W WO 2007105633 A1 WO2007105633 A1 WO 2007105633A1
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- Prior art keywords
- integer
- acrylic acid
- group
- reaction
- meth
- Prior art date
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003377 acid catalyst Substances 0.000 claims abstract description 6
- -1 fluoroalkyl iodide Chemical compound 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 33
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 21
- 239000007795 chemical reaction product Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000003999 initiator Substances 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 231100000693 bioaccumulation Toxicity 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 230000002940 repellent Effects 0.000 description 4
- 239000005871 repellent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- PGRFXXCKHGIFSV-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-iodobutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)I PGRFXXCKHGIFSV-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- RYRWDTRXCNOMOJ-UHFFFAOYSA-N dibutan-2-yl carbonate Chemical compound CCC(C)OC(=O)OC(C)CC RYRWDTRXCNOMOJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002497 iodine compounds Chemical group 0.000 description 1
- 239000012934 organic peroxide initiator Substances 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- YXTWPSHEGIZWEU-UHFFFAOYSA-N propoxy propyl carbonate Chemical compound CCCOOC(=O)OCCC YXTWPSHEGIZWEU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/38—Halogenated alcohols containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/16—Acyclic saturated compounds containing halogen atoms containing fluorine and iodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
- C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
Definitions
- the present invention relates to a polyfluoroalkyl alcohol or a (meth) acrylic acid derivative thereof and a method for producing them. More specifically, the present invention relates to a polyfluoroalkyl alcohol or a (meth) acrylic acid derivative thereof effectively used as a surfactant, a water / oil repellent raw material monomer and the like, and a production method thereof.
- Acrylic acid derivatives of polyperfluoroalkyl alcohols such as CF (CF) CH C
- H OCOCH CH is used in large quantities as a synthetic monomer for water and oil repellents for fibers.
- perfluoroalkyl alcohols which are precursors of attalylates, are widely used as surfactants and the like.
- Patent Document 1 Japanese Patent Publication No. 63-22237
- An object of the present invention is a compound having a perfluoroalkyl group having 6 or less carbon atoms, which is said to have low bioaccumulation, and can be used effectively as a surfactant or a water / oil repellent raw material monomer. It is an object of the present invention to provide a polyfluoroalkyl alcohol or a (meth) acrylic acid derivative thereof and a production method thereof.
- CF (CH CF) (CF CF) (CH CH) OR (I) (Where R is a hydrogen atom, an acrylic acid group or a methacrylic acid group, n is an integer from 1 to 6, a is an integer from 1 to 4, b is an integer from 1 to 3, c is an integer of 1 to 3, and a polyfluoroalkyl alcohol represented by (n 2n + 1 adjacent group of CF group is CH 2 CF group) or its (
- a meth) acrylic acid derivative is provided.
- a (meth) acrylic acid derivative of polyfluoroalkyl alcohol (R: acrylic acid group or methacrylic acid group) [Ib] is added to this polyfluoroalkyl alcohol [Ia]. It is produced by subjecting methacrylic acid to an ester reaction.
- the polyfluoroalkyl alcohol or a (meth) acrylic acid derivative thereof according to the present invention is a molecule that has a perfluoroalkyl group that has low bioaccumulation and is composed of 6 or less carbon atoms.
- CH CF group derived from fluorine-vinylidene in the HF easily de-HF
- polyfluoroalkyl alcohols are used as surfactants and their (meth) acrylic acid derivatives. Can be effectively used as a synthetic monomer for water and oil repellents.
- Polyfluoroalkyl alcohol [II] which is a starting material for the synthesis of polyfluoroalkyl alcohol [l a ], has the general formula
- the addition reaction of ethylene is carried out by subjecting the above compound [III] to addition reaction of pressurized ethylene in the presence of a peroxide initiator.
- the number of additions depends on the reaction conditions, but 1-3 1 is preferable.
- the reaction temperature is related to the decomposition temperature of the initiator used, the reaction is generally performed at about 80 to 120 ° C, and when a peroxide initiator that decomposes at a low temperature is used. The reaction at 80 ° C or below is possible.
- Peroxide initiators include tertiary butyl peroxide, di (tertiary butyl cyclohexyl) baroxydicarbonate, discetinoleperoxydicarbonate, di-n-propyl peroxycarbonate, Diisopropyl peroxycarbonate, di-secondary butyl carbonate and the like are used at a ratio of about 1 to 5 mol% with respect to the above compound [III] from the viewpoint of the inventive step and controllability of the reaction.
- a perfluoroalkyl iodide represented by C F I (n: 1 to 6) is converted into n 2n + l as described above.
- reaction temperature of the addition reaction of vinylidene fluoride and tetrafluoroethylene depends on the decomposition temperature of the initiator used, but by using a peroxide initiator that decomposes at a low temperature. Even under low pressure conditions, the reaction can be performed at 80 ° C or lower. Reaction is CFI or said
- Specific compounds [III] to which ethylene is added include the following compounds.
- This compound is a mixture of oligomers having various a and b values, and oligomers having specific a and b values can be isolated by distilling the mixture.
- the oligomer which does not have the predetermined a value and b value can be used again for the reaction of increasing the number of oligomers with vinylidene fluoride or tetrafluoroethylene, either isolated or in a mixture.
- Polyfluoroalkyl alcohol [Ia] which is one of the target substances of the present invention, is obtained by first reacting polyfluoroalkyl iodide [N] with N-methylformamide HCONH (CH 3),
- N-methylformamide preferably 5 to 10 times the molar amount
- an aqueous solution of P-toluenesulfonic acid is used as the acid catalyst.
- the reaction with N-methylformamide is carried out at a temperature of about 140 to 160 ° C for about 4 to 5 hours, and the subsequent hydrolysis reaction is carried out at a temperature of about 70 to 90 ° C for about 7 to 8 hours. Done It is.
- the obtained polyfluoroalkyl alcohol [Ia] can be esterified with acrylic acid or methacrylic acid to give a (meth) acrylic acid derivative [Ib].
- an aromatic hydrocarbon solvent such as toluene and benzene
- a catalyst such as P-toluenesulfonic acid
- hydroquinone as a polymerization inhibitor are added to polyfluoroalkyl alcohol, and about 90-100 ° C.
- After heating to about 1 to 2 times the molar amount of acrylic acid or methacrylic acid it is heated at about 110 to 120 ° C for about 2 to 5 hours to carry out dehydration and esterification reactions. Is called.
- the obtained product was separated by distillation under the conditions of a tower top temperature of 58 ° C and a pressure of 7.4 kPa (56 mmHg), and CF (CF) (CH CF) 1 (purity 99.5%) 203 g Got. This is a reference
- the obtained product was separated by distillation under the conditions of a tower top temperature of 71 ° C and a pressure of 2.6 kPa (20 mmHg), and CF (CF) (CH CF) (CF CF) 1 (purity 99.8%) 347 g was obtained.
- C F H (CF CF CF CF CF H) is an impurity contained in the raw material C F I.
- reaction product was distilled under reduced pressure under the conditions of an internal pressure of 0.2 kPa, an internal temperature of 100 to 144 ° C, and a tower top temperature of 58 to 59 ° C! ⁇ , 43.7g of purified reaction product (95.4GC%) (Distillation yield 88.2%) was obtained.
- the obtained purified reaction product was confirmed to be a compound represented by the following formula from the results of ⁇ -NMR and 19 F-NMR.
- reaction product was distilled under reduced pressure under the conditions of an internal pressure of 0.2 kPa, an internal temperature of 121 to 163 ° C, and a tower top temperature of 76 to 77 ° C, to obtain a purified reaction product (95.3GC%) 66.9g ( A distillation yield of 94.2%) was obtained.
- Example 3 The reaction product obtained in Example 1 (95.4GC%) 40.0 g (0.09 mol), toluene 21 g, p-toluenesulfonic acid 1.7 g and hydroquinone 0.05 g After charging the flask and heating the internal temperature to 100 ° C, 10.2 g (0.14 mol) of acrylic acid was added, and the mixture was stirred at an internal temperature of 115 ° C for 2 hours.
- This reaction product was distilled under reduced pressure under the conditions of an internal pressure of 0.2 kPa, an internal temperature of 103 to 143 ° C, and an overhead temperature of 60 to 61 ° C. ⁇ Purified reaction product (99.4GC%) 15.7g (Distillation yield 44%) was obtained.
- the obtained purified reaction product was confirmed to be a compound represented by the following formula from the results of ⁇ -NMR and 19 F-NMR.
- This reaction product was distilled under reduced pressure under the conditions of an internal pressure of 0.2 kPa, an internal temperature of 125 to 155 ° C, and a tower top temperature of 84 to 86 ° C to obtain a purified reaction product (99.4 GC%) 42.2 g (distillation yield 77%) was obtained.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/224,969 US7566801B2 (en) | 2006-03-10 | 2007-03-09 | Polyfluoroalkyl alcohol, or (METH)acrylic acid derivative thereof, and process for producing the same |
JP2007522338A JP4674604B2 (ja) | 2006-03-10 | 2007-03-09 | ポリフルオロアルキルアルコールまたはその(メタ)アクリル酸誘導体およびそれらの製造法 |
EP07738163A EP1995228B1 (en) | 2006-03-10 | 2007-03-09 | Polyfluoroalkyl alcohol or (meth)acrylic acid derivative thereof, and their production methods |
DE602007014332T DE602007014332D1 (de) | 2006-03-10 | 2007-03-09 | Polyfluoralkylalkohol bzw. (meth)acrylsäurederivat daraus und herstellungsverfahren |
CN2007800084607A CN101400633B (zh) | 2006-03-10 | 2007-03-09 | 多氟烷醇或其(甲基)丙烯酸衍生物及它们的制造方法 |
CA2643067A CA2643067C (en) | 2006-03-10 | 2007-03-09 | Polyfluoroalkyl alcohol, or (meth)acrylic acid derivative thereof, and process for producing the same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006-065188 | 2006-03-10 | ||
JP2006065188 | 2006-03-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007105633A1 true WO2007105633A1 (ja) | 2007-09-20 |
Family
ID=38509456
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2007/054678 WO2007105633A1 (ja) | 2006-03-10 | 2007-03-09 | ポリフルオロアルキルアルコールまたはその(メタ)アクリル酸誘導体およびそれらの製造法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7566801B2 (ja) |
EP (2) | EP2228356B1 (ja) |
JP (2) | JP4674604B2 (ja) |
CN (2) | CN101885666B (ja) |
CA (1) | CA2643067C (ja) |
DE (1) | DE602007014332D1 (ja) |
WO (1) | WO2007105633A1 (ja) |
Cited By (38)
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WO2010104065A1 (ja) * | 2009-03-13 | 2010-09-16 | ユニマテック株式会社 | ポリフルオロアルキルホスホン酸、その製造法およびそれを有効成分とする離型剤 |
EP2233462A1 (en) * | 2008-01-24 | 2010-09-29 | Unimatec Co., Ltd. | Fluoroalkyl alcohol mixture and method for producing the same |
EP2233464A1 (en) * | 2008-01-24 | 2010-09-29 | Unimatec Co., Ltd. | Mixture of fluoroalkyl alcohol-unsaturated carboxylic acid derivatives, polymer of the derivatives, and water repellent oil repellent agent containing the polymer as active ingredient |
JP2010215518A (ja) * | 2009-03-13 | 2010-09-30 | Unimatec Co Ltd | ポリフルオロアルキルホスホン酸およびその製造法 |
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WO2011030775A1 (ja) * | 2009-09-11 | 2011-03-17 | ユニマテック株式会社 | ポリフルオロアルキルホスホン酸オキシアルキレンエステル、その製造法およびそれを有効成分とする離型剤 |
JP2011056835A (ja) * | 2009-09-11 | 2011-03-24 | Unimatec Co Ltd | 離型剤 |
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WO2011055609A1 (ja) | 2009-11-04 | 2011-05-12 | ユニマテック株式会社 | ポリフルオロアルキルホスホン酸塩乳化剤およびこれを有効成分とする離型剤 |
JP2011098250A (ja) * | 2009-11-04 | 2011-05-19 | Unimatec Co Ltd | ポリフルオロアルキルホスホン酸塩乳化剤 |
WO2011148795A1 (ja) | 2010-05-25 | 2011-12-01 | ユニマテック株式会社 | 含フッ素ポリマー水性分散液 |
JP2012012616A (ja) * | 2011-10-19 | 2012-01-19 | Unimatec Co Ltd | 含フッ素ポリマーの製造法 |
JP2012041388A (ja) * | 2010-08-13 | 2012-03-01 | Shin-Etsu Chemical Co Ltd | 粘着剤用離型性組成物 |
WO2012035942A1 (ja) * | 2010-09-14 | 2012-03-22 | ユニマテック株式会社 | 新規含フッ素ビニルエーテル化合物およびその製造法 |
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JP2014084404A (ja) * | 2012-10-24 | 2014-05-12 | Shin Etsu Chem Co Ltd | 粘着剤用離型性組成物 |
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EP2228356A1 (en) | 2010-09-15 |
CN101400633B (zh) | 2013-05-29 |
CN101400633A (zh) | 2009-04-01 |
CA2643067C (en) | 2012-06-19 |
JP5152254B2 (ja) | 2013-02-27 |
US20090036706A1 (en) | 2009-02-05 |
EP2228356B1 (en) | 2016-06-22 |
US7566801B2 (en) | 2009-07-28 |
DE602007014332D1 (de) | 2011-06-16 |
CN101885666A (zh) | 2010-11-17 |
EP1995228A4 (en) | 2009-10-28 |
CN101885666B (zh) | 2013-07-24 |
EP1995228A1 (en) | 2008-11-26 |
JPWO2007105633A1 (ja) | 2009-07-30 |
JP2010189449A (ja) | 2010-09-02 |
CA2643067A1 (en) | 2007-09-20 |
EP1995228B1 (en) | 2011-05-04 |
JP4674604B2 (ja) | 2011-04-20 |
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