CN119013351A - Polymer composition containing fluoropolyether group, coating agent and article, and method for modifying surface of article - Google Patents
Polymer composition containing fluoropolyether group, coating agent and article, and method for modifying surface of article Download PDFInfo
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- CN119013351A CN119013351A CN202380034215.2A CN202380034215A CN119013351A CN 119013351 A CN119013351 A CN 119013351A CN 202380034215 A CN202380034215 A CN 202380034215A CN 119013351 A CN119013351 A CN 119013351A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 104
- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 239000011248 coating agent Substances 0.000 title claims description 66
- 238000000034 method Methods 0.000 title claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 31
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 229910052710 silicon Inorganic materials 0.000 claims description 17
- 238000012360 testing method Methods 0.000 claims description 14
- 229910000831 Steel Inorganic materials 0.000 claims description 12
- 239000010959 steel Substances 0.000 claims description 12
- 210000002268 wool Anatomy 0.000 claims description 9
- 238000011156 evaluation Methods 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002783 friction material Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000005259 measurement Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000004745 nonwoven fabric Substances 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 37
- 238000000576 coating method Methods 0.000 description 29
- 238000005299 abrasion Methods 0.000 description 23
- 239000005871 repellent Substances 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- -1 methoxymethoxy group Chemical group 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- 230000003373 anti-fouling effect Effects 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 125000005370 alkoxysilyl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 229910008314 Si—H2 Inorganic materials 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000000691 measurement method Methods 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000001680 brushing effect Effects 0.000 description 3
- 239000004566 building material Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 210000002374 sebum Anatomy 0.000 description 3
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000000572 ellipsometry Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002715 modification method Methods 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 2
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 1
- HUJRJVJYBSCYJD-UHFFFAOYSA-L CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC.CCCC[Sn](CCCC)(OC)OC Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC.CCCC[Sn](CCCC)(OC)OC HUJRJVJYBSCYJD-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940104873 methyl perfluorobutyl ether Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- LGUZHRODIJCVOC-UHFFFAOYSA-N perfluoroheptane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LGUZHRODIJCVOC-UHFFFAOYSA-N 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane 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)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- AQZYBQIAUSKCCS-UHFFFAOYSA-N perfluorotripentylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AQZYBQIAUSKCCS-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/46—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen
- C08G2650/48—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen containing fluorine, e.g. perfluropolyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Combustion & Propulsion (AREA)
- General Chemical & Material Sciences (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
Abstract
以特定比例含有(I)在单末端具有氟代氧烷基且在另一单末端具有反应性官能团的特定结构的聚合物、和(I I)在分子内具有氟代氧亚烷基且在两末端具有反应性官能团、不具有极性基团的特定结构的聚合物的含有氟聚醚基的聚合物组合物可形成拒水拒油性、磨损耐久性优异、且由于高摩擦系数而具有滑动抑制性的固化被膜。A fluoropolyether group-containing polymer composition containing (I) a polymer of a specific structure having a fluorooxyalkyl group at one end and a reactive functional group at the other end, and (II) a polymer of a specific structure having a fluorooxyalkylene group in the molecule and reactive functional groups at both ends and no polar group in a specific ratio can form a cured film having excellent water and oil repellency, wear durability, and slip-inhibiting properties due to a high friction coefficient.
Description
Technical Field
The present invention relates to a composition containing a fluoropolyether group-containing polymer (a compound having a fluorooxyalkyl group or a fluorooxyalkylene group in a molecule), and more particularly, to a fluoropolyether group-containing polymer composition capable of forming a cured coating film excellent in water and oil repellency, abrasion resistance, and slip inhibition, a coating agent containing the composition, and an article having a layer containing a cured product of the coating agent, and further, to a surface modification method of an article comprising a step of coating and curing the coating agent to form a layer.
Background
In recent years, touch panels for screens have been accelerated, including displays of mobile phones. However, the touch panel has a bare screen, and there are many opportunities for direct contact of fingers, cheeks, etc., and dirt such as sebum is likely to adhere to the touch panel. Therefore, in order to improve the appearance and visibility, the demands for techniques for making it difficult to attach fingerprints to the surface of a display and techniques for easily removing dirt have been increasing year by year, and it has been desired to develop a material capable of satisfying these demands. Recently, it has become a problem that dirt such as sebum is easily attached to not only the display surface but also the case, and it is desired to provide a water-repellent and oil-repellent layer to both the display and the case. However, the conventional water-repellent oil-repellent layer has a problem of deterioration in stain-proofing performance in use, although it has a high water-repellent oil-repellent property and excellent stain-removing property.
In general, a compound containing a fluoropolyether group has water-and oil-repellency, chemical resistance, lubricity, mold release property, stain resistance, and the like because of its very small surface free energy. By utilizing the properties, the composition is widely used in industry as a water-repellent, oil-repellent and stain-proofing agent for paper, fiber and the like, a lubricant for magnetic recording media, an oil-repellent agent for precision equipment, a mold release agent, a cosmetic, a protective film and the like. However, the properties of the coating composition mean non-adhesiveness and non-adhesiveness to other substrates, and even if the coating composition can be applied to the substrate surface, it is difficult to adhere the coating to the substrate.
On the other hand, as a substance for binding an organic compound to a substrate surface such as glass or cloth, a silane coupling agent is known and widely used as a coating agent for various substrate surfaces. The silane coupling agent has an organofunctional group and a reactive silyl group (generally, a hydrolyzable silyl group such as an alkoxysilyl group) in 1 molecule. The hydrolyzable silyl group undergoes a self-condensation reaction by moisture in the air or the like to form a film. The film is chemically and physically bonded to the surface of glass, metal, or the like through the hydrolyzable silyl group, and is a durable, strong film.
Accordingly, there has been disclosed a composition in which a fluoropolyether group-containing polymer having a hydrolyzable silyl group introduced into a fluoropolyether group-containing compound is used to easily adhere to the substrate surface and a coating film having water/oil repellency, chemical resistance, lubricity, releasability, stain resistance and the like can be formed on the substrate surface (patent documents 1 to 6: japanese patent application publication Nos. 2008-534696, 2008-537557, 2012-072272, 2012-157856, 2013-136833, 2015-199906).
The cured film (antifouling coating film layer) of a glass substrate surface or the like surface-treated with the composition containing the fluoropolyether group-containing polymer having a hydrolyzable silyl group introduced into the fluoropolyether group-containing compound is excellent in abrasion resistance to steel wool and high in sliding property. In addition to the performance of preventing dirt, the stain-proofing coating film layer on the surface of the touch panel display also pays attention to the feeling of use (good sliding and smooth touch) when the touch panel is used. A good feeling in use is associated with a low coefficient of friction (patent document 6: japanese patent application laid-open No. 2015-199906).
On the other hand, the low friction coefficient may be disadvantageous in the case surface of the portable electronic device terminal or the like. That is, if the friction coefficient is low, the possibility of dropping, vibration, or the like at the time of use of the terminal increases. Therefore, it is important to apply an antifouling coating film layer to various applications including portable electronic equipment terminals while maintaining antifouling performance and durability and controlling the friction coefficient (patent document 7: japanese patent application laid-open No. 2019-131808).
However, when the friction coefficient of the anti-fouling coating film layer is controlled to be high, the abrasion durability is insufficient.
Prior art literature
Patent literature
Patent document 1: japanese patent publication No. 2008-534696
Patent document 2: japanese patent publication No. 2008-537557
Patent document 3: japanese patent application laid-open No. 2012-072272
Patent document 4: japanese patent application laid-open No. 2012-157856
Patent document 5: japanese patent laid-open publication No. 2013-136833
Patent document 6: japanese patent laid-open No. 2015-199906
Patent document 7: japanese patent application laid-open No. 2019-131808
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made in view of the above-described circumstances, and an object thereof is to provide a fluoropolyether group-containing polymer composition capable of forming a cured film having excellent water and oil repellency and abrasion resistance and a high friction coefficient, a coating agent containing the composition, and an article having a layer containing a cured product of the coating agent, and further to provide a surface modification method of an article comprising a step of coating and curing the coating agent to form a layer.
Means for solving the problems
The present inventors have intensively studied in order to achieve the above object, and as a result, found that: in the above-mentioned polymer composition containing a fluoropolyether group, the present invention has been completed by combining two specific fluoropolyether group-containing polymers described later in a specific ratio, whereby a cured film excellent in water and oil repellency, abrasion durability and slip inhibition due to a high friction coefficient can be formed by combining the polymer and/or a partial (hydrolyzed) condensate thereof (particularly, a coating agent comprising the composition).
Accordingly, the present invention provides the following fluoropolyether group-containing polymer composition, coating agent and article, and method for modifying the surface of article.
[1]
A fluoropolyether group-containing polymer composition comprising: (I) A fluoropolyether group-containing polymer represented by the following general formula (1) and/or a partial (hydrolyzed) condensate thereof; and (I I) a fluoropolyether group-containing polymer represented by the following general formula (2) and/or a partial (hydrolysis) condensate thereof,
[ Chemical 1]
Wherein Rf1 is a fluorooxyalkyl group having a repeating unit of- (C 3F6O)b - (wherein the repeating unit C 3F6 O is a branched structure, b is an integer of 2 to 200. -, J is a single bond or a carbonyl group, Q is a single bond or-NH-group or an alkylene group having 1 to 4 carbon atoms of a group containing a nitrogen atom, L is independently a single bond or a divalent hetero atom, M is independently a divalent hydrocarbon group which may have a silicon atom and/or a siloxane bond, X is independently a hydroxyl group or a hydrolyzable group, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, n is independently an integer of 1 to 3 for each unit bonded to a silicon atom, a is 2 or 3,
W-O-CH2-Rf2-CH2-O-W(2)
Wherein Rf2 is a linear fluorooxyalkylene group having no branch and comprising a unit represented by- (C cF2cO)-(CcF2c O unit having a linear structure and C is an integer of 1 to 6), W is independently a monovalent group having a silyl group having a hydroxyl group or a hydrolyzable silyl group at the terminal and having no polar group,
Wherein the content of the component (I) in the total of the components (I) and (I I) is 65 to 95% by mass.
[2]
The fluoropolyether group-containing polymer composition according to [1], wherein the (I I) component is represented by the following general formula (3),
[ Chemical 2]
Wherein Rf2 is a linear fluorinated oxyalkylene group containing a unit represented by- (C cF2cO)-(CcF2c O unit being a linear structure, C being an integer of 1 to 6), and having no branching, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, n is independently an integer of 1 to 3 for each unit bonded to a silicon atom, Y is independently a hydrocarbon group having 2 to 6 valences, and may have a silicon atom and/or a siloxane bond, and m is independently an integer of 1 to 5.
[3]
The fluoropolyether group-containing polymer composition according to [1] or [2], wherein Rf1 of the formula (1) is a fluorooxyalkyl group represented by the following general formula (4),
[ Chemical 3]
Wherein A is a fluorine atom, a hydrogen atom, or a fluoroalkyl group having a-CF 3 group at the end, and b1 is an integer of 1 to 200.
[4]
The fluoropolyether group-containing polymer composition according to any one of [1] to [3], wherein X in the formula (1) is independently a group selected from the group consisting of a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxyalkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms and a halogen group.
[5]
The fluoropolyether group-containing polymer composition according to any one of [1] to [4], wherein the polymer represented by formula (1) is selected from polymers represented by the following formulae,
[ Chemical 4]
Wherein b1' is an integer of1 to 199.
[6]
The fluoropolyether group-containing polymer composition according to any one of [1] to [5], wherein Rf2 is represented by the following formula (5),
[ Chemical 5]
Wherein d is an integer of 0 to 5 independently for each unit, p, q, r, s, t, u is an integer of 0 to 200, p+q+r+s+t+u=an integer of 10 to 250, each of these units is linear, and each of the repeating units shown in brackets with p, q, r, s, t, u may be bonded randomly.
[7]
The fluoropolyether group-containing polymer composition according to any one of [1] to [6], wherein Rf2 is selected from polymers represented by the following formula,
[ Chemical 6]
-Cd′F2d′-O-(C2F4O)q′-Cd′F2d′-
-Cd′F2d′-O-(C3F6O)r′-Cd′F2d′-
-Cd′F2d′-O-(CF2O)p′(C2F4O)q′-Cd′F2d′-
-Cd′F2d′-O-(C2F4O)q′(C4F8O)s′-Cd′F2d′-
-Cd′F2d′-O-(CF2O)p′(C2F4O)q′(C3F6O)r′-Cd′F2d′-
-Cd′F2d′-O-(C2F4O)q′(C4F8O)s′(C6F12O)u′-Cd′F2d′-
-Cd′F2d′-O-(CF2O)p′(C2F4O)q′(C3F6O)r′(C5F10O)t′-Cd′F2d′-
-Cd′F2d′-O-(CF2O)p′(C2F4O)q′(C3F6O)r′(C4F8O)s′(C5F10O)t′(C6F12O)u′-Cd′F2d′-
Wherein p ', q ', r ', s ', t ' and u ' are integers of 1 to 200, the sum of p ', q ', r ', s ', t ' and u ' is 10 to 250, each of these units is linear, each of the repeating units shown in brackets with p ', q ', r ', s ', t ' and u ' may be randomly bonded, and d ' is independently an integer of 0 to 5 for each of these units, each of these units being linear.
[8]
The fluoropolyether group-containing polymer composition according to any one of [2] to [7], wherein in the formula (3), X is independently a group selected from the group consisting of a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxyalkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, and a halogen group.
[9]
The fluoropolyether group-containing polymer composition according to any one of [2] to [8], wherein the polymer represented by the formula (3) is selected from polymers represented by the following formulas,
[ Chemical 7]
(H3CO)3Si-H2CH2CH2C-O-CH2-CF2-o-(CF2O)p1(CF2O)q1-CF2-CH2-O-CH2CH2-Si(OCH3)3
Wherein p1 and q1 are integers of 1 to 199, and the total of p1 and q1 is 10 to 200.
[10]
A coating agent comprising the fluoropolyether group-containing polymer composition according to any one of [1] to [9 ].
[11]
An article having a layer containing a cured product of the coating agent according to [10 ].
[12]
The article according to [11], wherein the dynamic friction coefficient of the surface is 0.13 or more under the following measurement conditions, the wear durability is 5000 or more under the following test conditions,
[ Dynamic Friction coefficient measurement Condition ]
Determination by the method according to ASTM D1894
Load: 100gf
Stroke: 100mm of
Stretching speed: 500 mm/min
Contact area: 1X 3cm 2
Friction material: nonwoven (BEMCOT (manufactured by Asahi chemical Co., ltd.))
Test environmental conditions: 25 ℃ and relative humidity of 50%
[ Wear durability test conditions ]
Evaluation of Steel wool abrasion durability Using reciprocating abrasion tester
Friction material: steel wire #0000 (Bons tar)
Load: 1kgf
Reciprocating distance: 40mm
Reciprocating speed: 60 reciprocations per minute
Test environmental conditions: 25 ℃ and relative humidity of 50%
The water contact angle of the frictional worn portion was measured for 2500 times per frictional reciprocation, and the number of times of wear reciprocation at which the water contact angle was maintained at 100 degrees or more was set as the number of times of wear durability.
[13]
A method for modifying the surface of an article, comprising the steps of: a coating agent comprising the fluoropolyether-group-containing polymer composition according to any one of [1] to [9] is applied and cured to form a layer on the entire surface or a part of the surface of an article by a dry method or a wet method.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the fluoropolyether group-containing polymer composition of the present invention, a cured film having excellent water and oil repellency and high abrasion durability despite a high friction coefficient can be formed, and thus an article (for example, a portable electronic device terminal or the like) having a layer containing a cured product of the composition of the present invention (in particular, a coating agent containing the composition) is excellent in water and oil repellency and abrasion durability and has high slip inhibition.
Detailed Description
In the present invention, the term "partial (hydrolysis) condensate" refers to a partial condensate or a partial hydrolysis condensate.
The fluoropolyether group-containing polymer composition of the present invention comprises two specific fluoropolyether group-containing polymers in a specific ratio, wherein one of the fluoropolyether group-containing polymers has a component (I) of a polymer having a fluorooxyalkyl group in the molecule and a reactive functional group at one end of the polymer, and the other component (I I) has a fluorooxyalkylene group in the molecule and a reactive functional group at both ends of the polymer.
In the fluoropolyether group-containing polymer composition of the present invention, the polymer having a fluorooxyalkyl group in the molecule and a reactive functional group at one end of the polymer as the component (I) is a fluoropolyether group-containing polymer represented by the following general formula (1) and/or a partial (hydrolysis) condensate thereof.
[ Chemical 8]
(Wherein Rf1 is a fluorooxyalkyl group having a repeating unit of- (C 3F6O)b - (wherein the repeating unit C 3F6 O is a branched structure, b is an integer of 2 to 200.) -, J is a single bond or a carbonyl group, Q is a single bond or-NH-group or an alkylene group of 1 to 4 carbon atoms which may contain a group containing a nitrogen atom, L is independently a single bond or a divalent hetero atom (preferably an oxygen atom in an ether bond), M is independently a divalent hydrocarbon group which may have a silicon atom and/or a siloxane bond, X is independently a hydroxyl group or a hydrolyzable group, R is independently an alkyl group of 1 to 4 carbon atoms or a phenyl group, n is independently an integer of 1 to 3 for each unit bonded to a silicon atom, a is 2 or 3.)
In the fluoropolyether group-containing polymer composition of the present invention, the polymer having a fluorooxyalkylene group in the molecule and reactive functional groups at both ends of the polymer as the component (I I) is a fluoropolyether group-containing polymer represented by the following general formula (2) and/or a partial (hydrolyzed) condensate thereof.
W-O-CH2-Rf2-CH2-O-W(2)
(Wherein Rf2 is a linear fluorooxyalkylene group having no branch and comprising a unit represented by- (C cF2cO)-(CcF2c O unit having a linear structure and C is an integer of 1 to 6), and W is independently a monovalent group having a silyl group having a hydroxyl group or a hydrolyzable silyl group at the terminal and having no polar group.)
In the fluoropolyether group-containing polymer composition of the present invention, the content of the component (I) in the total of the component (I) and the component (I I) is 65 to 95% by mass, preferably 65 to 90% by mass, and more preferably 65 to 85% by mass. If the content of the component (I) in the total of the components (I) and (I I) is less than 65% by mass, the friction coefficient and wear durability of the cured film are reduced, and if it is more than 95% by mass, the friction coefficient is high, but the wear durability of the cured film is reduced.
The fluoropolyether group-containing polymer of the formula (1) has a structure in which a fluorinated oxyalkyl group is bonded to a hydrolyzable silyl group such as an alkoxysilyl group or a hydroxyl group-containing silyl group via a linking group, and has 2 or more hydrolyzable silyl groups such as alkoxysilyl groups or hydroxyl group-containing silyl groups in the molecule. Further, the main chain structure is composed of a group represented by- (C 3F6O)b - (wherein the repeating unit C 3F6 O is a branched structure) and b is an integer of 2 to 200) -whereby the friction coefficient is high (sliding is not easy).
In the above formula (1), rf1 is a fluorooxyalkyl group having a group (a repeating structure of hexafluoropropylene oxide) represented by- (C 3F6O)b - (a repeating unit C 3F6 O is a branched structure represented by-CF (CF 3)CF2 O) (i.e., a repeating unit structure of hexafluoropropylene oxide ring opening)), b is an integer of 2 to 200, preferably an integer of 3 to 100) as a main structure, preferably a fluorooxyalkyl group represented by the following general formula (4).
[ Chemical 9]
(Wherein A is a fluorine atom, a hydrogen atom or a fluoroalkyl group having a-CF 3 group at the end, and b1 is an integer of 1 to 200.)
In the above formula (4), A is a fluorine atom, a hydrogen atom, or a fluoroalkyl group having a-CF 3 group at the end, and examples of the fluoroalkyl group having a-CF 3 group at the end include CF3CF2CF2CF2-、CF3CF2CF2-、CF3CF2-、CF3-、CF3OCF2CFH-、CF3CF2CF2OCF2CFH-、CF3OCF2CF2CF2OCF2CFH-, and is preferably CF 3CF2CF2 -.
B1 is an integer of 1 to 200, preferably an integer of 3 to 100, more preferably an integer of 5 to 50. If b1 is smaller than the upper limit, the adhesion and curability are good, and handling is easy, and if b1 is larger than the lower limit, the characteristics of the fluorooxyalkyl group can be sufficiently exhibited, which is preferable.
As Rf1, specifically, the following groups can be exemplified.
[ Chemical 10]
(Wherein b1' is an integer of 1 to 199, preferably an integer of 3 to 100.)
In the above formula (1), J is a single bond or a carbonyl group (-C (=o) -).
In the above formula (1), Q is a single bond or-NH-group or an alkylene group having 1 to 4 carbon atoms which may contain a group containing a nitrogen atom, and the following groups are exemplified as specific examples other than the single bond of Q. It is preferable that the left bond end is bonded to J and the right bond end is bonded to a carbon atom.
[ Chemical 11]
(Wherein e1 is an integer of 1 to 4, preferably 1 or 2, and e2 is an integer of 1 to 4, preferably 1,2 or 3.)
In the above formula (1), L is independently a single bond or a divalent heteroatom, and examples of the divalent heteroatom include an oxygen atom, a nitrogen atom, and a sulfur atom, and preferably an oxygen atom (an oxygen atom in an ether bond). L is preferably a single bond or an oxygen atom.
In the above formula (1), M is independently a divalent hydrocarbon group which may have a silicon atom and/or a siloxane bond, and specifically, examples of M include an alkylene group having 3 to 10 carbon atoms such as a propylene group, a butylene group, a hexamethylene group, etc., an alkylene group having 3 to 10 carbon atoms including an arylene group having 6 to 8 carbon atoms such as a phenylene group (for example, an alkylene-arylene group having 8 to 16 carbon atoms, etc.), a divalent group in which alkylene groups having 3 to 10 carbon atoms are bonded to each other via a silylene structure or a silylene structure, a divalent group in which alkylene groups having 2 to 10 carbon atoms are bonded to each other via a silicon alkylene structure, preferably a divalent group in which alkylene groups having 2 to 10 carbon atoms are bonded to the bonding end of a linear divalent organopolysiloxane residue having 2 to 5 carbon atoms, etc., an alkylene group having 3 to 10 carbon atoms including a phenylene group, an alkylene group having 3 to 10 carbon atoms bonded to each other via a silylene structure, a divalent group having 3 to 10 carbon atoms are bonded to each other via a silicon alkylene group having 3 to 10 carbon atoms, and a divalent group having 3 to 10 carbon atoms bonded to each other via a divalent organopolysiloxane residue.
Among them, the following structures can be exemplified as the silylene structure and the silylene structure.
[ Chemical 12]
( Wherein R 1 is an alkyl group having 1 to 4 carbon atoms such as methyl, ethyl, propyl or butyl, or an aryl group having 6 to 10 carbon atoms such as phenyl, and R 1 may be the same or different. R 2 is an alkylene group having 1 to 6 carbon atoms such as methylene, ethylene or propylene (trimethylene or methylethylene), or an arylene group having 6 to 10 carbon atoms such as phenylene. )
The following groups can be exemplified as the linear divalent organopolysiloxane residue having 2 to 10 silicon atoms, preferably 2 to 5 silicon atoms.
[ Chemical 13]
( Wherein R 1 is the same as described above. g is an integer of 1 to 9, preferably an integer of 1 to 4. )
As M, a group represented by the following formula is exemplified.
[ Chemical 14]
-(CH2)f1-
(Wherein f1 is an integer of 3 to 10, preferably an integer of 3 to 6, f2 is an integer of 1 to 6, preferably an integer of 2 to 4, f3 is an integer of 3 to 10, preferably an integer of 3 to 6, g is an integer of 1 to 9, preferably an integer of 1 to 4.)
Specific examples of M include the following groups. It is preferable that the left-side bond end is bonded to L and the right-side bond end is bonded to a silicon atom.
[ 15]
-CH2CH2CH2-
-CH2CH2CH2CH2-
-CH2CH2CH2CH2CH2-
-CH2CH2CH2CH2CH2CH2-
[ 16]
In the above formula (1), X is independently a hydroxyl group or a hydrolyzable group, and specifically, examples thereof include an alkoxy group having 1 to 10 carbon atoms such as a hydroxyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a butoxy group, an alkoxyalkoxy group having 2 to 10 carbon atoms such as a methoxymethoxy group, and a methoxyethoxy group, an acyloxy group having 1 to 10 carbon atoms such as an acetoxy group, and an alkenyloxy group having 2 to 10 carbon atoms such as an isopropoxy group, a chloro group, a bromo group, and a halo group such as an iodo group. Among them, methoxy, ethoxy, isopropoxy, and chloro are preferable.
R is independently an alkyl group having 1 to 4 carbon atoms such as methyl, ethyl, propyl, butyl or the like, or phenyl group, and among these, methyl groups are preferred.
N is independently an integer of 1 to 3, preferably 2 or 3, for each unit bonded to a silicon atom, and more preferably 3 from the viewpoints of reactivity and adhesion to a substrate.
In the above formula (1), as-S iX n(R)3-n, a trialkoxysilyl group such as trimethoxysilyl group, triethoxysilyl group, tripropoxysilyl group, tris (isopropoxy) silyl group, tributoxysilyl group, tris (isobutoxy) silyl group, tris (sec-butoxy) silyl group, or tris (tert-butoxy) silyl group is preferable.
In the above formula (1), a is 2 or 3.
In the above formula (1), among 2 or 3L groups in 1 molecule, all of L groups are preferably single bonds, or 1L group is an oxygen atom, and the remaining 1 or 2L groups are preferably single bonds, in particular, when a is 2, one L group of L groups in 1 molecule is preferably an oxygen atom, and the other L group is preferably a single bond, and when a is 3, all L groups in 1 molecule are preferably single bonds.
As the fluoropolyether group-containing polymer represented by the above formula (1), a polymer represented by the following formula can be exemplified.
[ Chemical 17]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 18]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 19]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 20]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 21]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 22]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 23]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 24]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 25]
(Wherein b1' is an integer of 1 to 199.)
[ Chemical 26]
(Wherein b1' is an integer of 1 to 199.)
The fluoropolyether group-containing polymer represented by the above formula (1) is preferably a polymer represented by the following formula.
[ Chemical 27]
(Wherein b1' is an integer of 1 to 199.)
The fluoropolyether group-containing polymer of the above formula (2) has a structure in which a hydrolyzable silyl group such as a fluorooxyalkylene group and an alkoxysilyl group or a hydroxyl group-containing silyl group are bonded via a linking group having no polar group, and a simpler bonding system is achieved in which 1 or more hydrolyzable silyl groups such as alkoxysilyl groups or hydroxyl group-containing silyl groups are present at both ends of the polymer, and a total of 2 or more in total are present in the molecule, and in addition to the hydrolyzable silyl groups or hydroxyl group-containing silyl groups, no polar group, specifically no carbonyl group, -NH-group, amide group, hydroxyl group or the like is present in the molecule.
In the above formula (2), rf2 is represented by the formula: - (C cF2cO)-(CcF2c O unit is a linear structure, and C is an integer of 1 to 6), and a linear fluorooxyalkylene group having no branched chain. By using a linear fluorooxyalkylene group having no branch, the cured film can have high abrasion durability.
The fluorooxyalkylene group of Rf2 is preferably a group represented by the following formula (5).
[ Chemical 28]
( Wherein d is an integer of 0 to 5 independently for each unit, p, q, r, s, t, u is an integer of 0 to 200, and p+q+r+s+t+u=an integer of 10 to 250, and each unit is linear. In addition, the repeat units shown in brackets with p, q, r, s, t, u may be randomly bonded. )
In the above formula (5), d is independently an integer of 0 to 5, preferably an integer of 0 to 2, more preferably 1 or 2, for each unit.
P, q, r, s, t, u is an integer of 0 to 200, preferably, p is an integer of 10 to 150, q is an integer of 10 to 150, r is an integer of 0 to 20, s is an integer of 0 to 20, t is an integer of 0 to 20, u is an integer of 0 to 20, and p+q+r+s+t+u is an integer of 10 to 250, preferably, an integer of 20 to 150. If p+q+r+s+t+u is smaller than the upper limit, the adhesion between the base material and the cured film and the reactivity at the time of synthesis are good, and if it is larger than the lower limit, the water/oil repellency and abrasion durability of the cured film are good. Each of these units is linear. In addition, the repeat units shown in brackets with p, q, r, s, t, u may be randomly bonded.
The fluorooxyalkylene group of Rf2 can be represented by the following structure, for example.
[ Chemical 29]
-Cd′F2d′-O-(C2F4O)q′-Cd′F2d′-
-Cd′F2d′-O-(C3F6O)r′-Cd′F2d′-
-Cd′F2d′-O-(CF2O)p′(C2F4O)q′-Cd′F2d′-
-Cd′F2d′-O-(C2F4O)q′(C4F8O)s′-Cd′F2d′-
-Cd′F2d′-O-(CF2O)p′(C2F4O)q′(C3F6O)r′-Cd′F2d′-
-Cd′F2d′-O-(C2F4O)q′(C4F8O)s′(C6F12O)u′-Cd′F2d′-
-Cd′F2d′-O-(CF2O)p′(C2F4O)q′(C3F6O)r′(C5F10O)t′-Cd′F2d′-
-Cd′F2d′-O-(CF2O)p′(C2F4O)q′(C3F6O)r′(C4F8O)s′(C5F10O)t′(C6F12O)u′-Cd′F2d′-
( Wherein p ', q', r ', s', t 'and u' are integers of 1 to 200, and the total of p ', q', r ', s', t 'and u' is 10 to 250, and each of these units is linear. In addition, the repeat units shown in brackets with p ', q', r ', s', t 'and u' may be randomly bonded. d' is independently an integer of 0 to 5 for each unit, and each unit is linear. )
As Rf2, the following groups can be preferably used.
[ Chemical 30]
-CF2-O-(CF2O)p″(CF2CF2O)q″-CF2-
(Wherein p 'and q' are each an integer of 1 to 199, and the sum of p '+q' is an integer of 10 to 200, and the arrangement of the repeating units (CF 2CF2 O) and (CF 2 O) in the formula is random.)
In the above formula (2), W is independently a monovalent group having a silyl group or a hydrolyzable silyl group having a hydroxyl group at the terminal, and having no polar group, and is preferably a monovalent group composed of a silyl group or a hydrolyzable silyl group having a hydroxyl group at the terminal, and a linking group having no polar group (carbonyl, -NH-group, amide group, hydroxyl group, or the like) linking the silyl group to an O group (ether bond oxygen atom), and examples of such W include groups represented by the following formulas (6 a) to (6 e).
[ 31]
( Wherein X, R, n is the same as described above. D is a divalent organic group having 1 to 20 carbon atoms and being substituted with fluorine, v1 is an integer of 2 to 6, v2 is independently an integer of 2 to 10, and g1 is an integer of 1 to 9. )
In the above formulae (6 a) to (6 e), D is a divalent organic group which may be substituted with fluorine and has 1 to 20 carbon atoms, preferably 2 to 8 carbon atoms, and is preferably a divalent hydrocarbon group which may be substituted with fluorine and has 1 to 20 carbon atoms, more preferably 2 to 8 carbon atoms, and examples of the divalent hydrocarbon group include a methylene group, an ethylene group, a propylene group (trimethylene group, methylethylene group), a butylene group (tetramethylene group, methylpropylene group), an alkylene group such as hexamethylene group, octamethylene group, an arylene group such as phenylene group, a combination of 2 or more of these groups (alkylene-arylene group and the like), a group in which a part or all of hydrogen atoms of these groups are substituted with fluorine atoms, and the like. As D, ethylene, propylene, butylene, hexamethylene, phenylene are preferred.
In the above formulae (6 a) to (6 e), v1 is an integer of 2 to 6, preferably an integer of 2 to 4, v2 is independently an integer of 2 to 10, preferably an integer of 3 to 6, and g1 is an integer of 1 to 9, preferably an integer of 1 to 4.
As such W, specifically, the following groups can be exemplified.
[ Chemical 32]
-CH2CH2CH2-Si(OCH3)3
-CH2CH2CH2CH2-Si(OCH3)3
-CH2CH2CH2CH2CH2-Si(OCH3)3
-CH2CH2CH2CH2CH2CH2-Si(OCH3)3
[ 33]
The fluoropolyether group-containing polymer of the above formula (2) is more preferably a polymer represented by the following general formula (3).
[ Chemical 34]
( Wherein Rf2 and R, X, n are the same as defined above, and Y is independently a hydrocarbon group having 2 to 6 valences, and may have a silicon atom and/or a siloxane bond. m is independently an integer of 1 to 5. )
In the above formula (3), Y is independently a hydrocarbon group having a valence of 2 to 6, preferably 2 to 4, more preferably divalent, and may have a silicon atom and/or a siloxane bond, and a coating film excellent in water repellency and oil repellency can be formed by containing no polar group in the molecule.
Examples of Y include an alkylene group having 3 to 10 carbon atoms such as a propylene group, a butylene group, and a hexamethylene group, an alkylene group having 2 to 10 carbon atoms including an arylene group having 6 to 8 carbon atoms such as a phenylene group (for example, an alkylene-arylene group having 8 to 16 carbon atoms), a divalent group in which alkylene groups having 2 to 10 carbon atoms are bonded to each other via a silylene structure or a silylene structure, a linear, branched, or cyclic organopolysiloxane residue having 2 to 10 carbon atoms, and a group having 2 to 6 carbon atoms in which a linear, branched, or cyclic organopolysiloxane residue having 2 to 5 carbon atoms is bonded to the bonding end thereof, and preferably an alkylene group having 3 to 10 carbon atoms, an alkylene group having 2 to 10 carbon atoms including a phenylene group, a divalent group in which alkylene groups having 2 to 10 carbon atoms are bonded to each other via a silylene structure or a silylene structure, and a branched, or cyclic organopolysiloxane having 2 to 10 carbon atoms having 2 to 4 carbon atoms, and more preferably a terminal alkylene group having 2 to 4 carbon atoms bonded to3 carbon atoms.
Among them, as the silylene structure and the silylene structure, the same structure as that exemplified in M of formula (1) can be exemplified.
Examples of the organopolysiloxane residue having 2 to 6 valences, which is a linear, branched or cyclic residue having 2 to 10 silicon atoms, preferably 2 to 5 silicon atoms, include the following groups.
[ 35]
[ 36]
( Wherein R 1 is the same as described above. g1 is an integer of 1 to 9, preferably an integer of 1 to 4, h is an integer of 2 to 6, preferably an integer of 2 to 4, j is an integer of 0to 8, preferably 0 or 1, h+j is an integer of 3 to 10, preferably an integer of 3 to 5, and k is an integer of 1 to 3, preferably 2 or 3. )
Examples of Y include groups represented by the following formulas.
[ 37]
-(CH2)v-
( Wherein v1, v2 and g1 are the same as those described above. v is an integer of 3 to 10, preferably 3 to 6, and v0 is an integer of 2 to 10, preferably 3 to 6. )
Specific examples of Y include the following groups.
[ 38]
-CH2CH2CH2-
-CH2CH2CH2CH2-
-CH2CH2CH2CH2CH2-
-CH2CH2CH2CH2CH2CH2-
[ 39]
M is independently an integer of 1 to 5, and if m is less than 1, adhesion to a substrate is reduced, and if m is 6 or more, a terminal alkoxy value is excessively high, which adversely affects performance, and thus is preferably an integer of 1 to 3, particularly preferably 1.
The fluoropolyether group-containing polymer represented by the above formula (3) can be exemplified by a polymer represented by the following formula.
[ 40]
(H3CO)3Si-H2CH2CH2C-O-CH2-CF2-O-(CF2O)p1(CF2CF2O)q1-CF2-CH2-O-CH2CH2CH2-Si(OCH3)3
(Wherein p1 and q1 are integers of 1 to 199, and the total of p1 and q1 is 10 to 200.)
The present invention provides a coating agent comprising a polymer composition containing a fluoropolyether group, wherein the polymer composition contains a fluoropolyether group represented by the formula (1) and a polymer containing a fluoropolyether group represented by the formula (2), in particular a polymer containing a fluoropolyether group represented by the formula (3), in a specific ratio. The coating agent may contain a partially (hydrolyzed) condensate obtained by condensing hydroxyl groups of the polymer containing a fluoropolyether group represented by the above formula (1) and the above formula (2), or hydroxyl groups obtained by partially hydrolyzing terminal hydrolyzable groups of the polymer containing a fluoropolyether group by a known method in advance.
To the coating agent, if necessary, a hydrolysis condensation catalyst such as an organotin compound (dibutyltin dimethoxy, dibutyltin dilaurate, etc.), an organotitanium compound (tetra-n-butyl titanate, etc.), an organic acid (acetic acid, methanesulfonic acid, fluorine-modified carboxylic acid, etc.), an inorganic acid (hydrochloric acid, sulfuric acid, etc.) may be added. Among these, acetic acid, tetra-n-butyl titanate, dibutyltin dilaurate, fluorine-modified carboxylic acid, and the like are particularly preferable.
The amount of the hydrolytic condensation catalyst to be added is usually 0.01 to 5 parts by mass, particularly 0.1 to 1 part by mass, based on 100 parts by mass of the polymer composition containing the fluoropolyether group.
The coating agent may contain a suitable solvent. Examples of such solvents include fluorine-modified aliphatic hydrocarbon solvents (perfluoroheptane, perfluorooctane, etc.), fluorine-modified aromatic hydrocarbon solvents (1, 3-bis (trifluoromethyl) benzene, etc.), fluorine-modified ether solvents (methyl perfluorobutyl ether, ethyl perfluorobutyl ether, perfluoro (2-butyltetrahydrofuran), etc.), fluorine-modified alkylamine solvents (perfluorotributylamine, perfluorotripentylamine, etc.), hydrocarbon solvents (petroleum spirit, toluene, xylene, etc.), ketone solvents (acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.). Among these, from the viewpoints of solubility, wettability and the like, fluorine-modified solvents are preferable, and 1, 3-bis (trifluoromethyl) benzene, perfluoro (2-butyltetrahydrofuran), perfluoro tributylamine and ethyl perfluorobutyl ether are particularly preferable.
The solvent may be mixed with 2 or more of them, and it is preferable to uniformly dissolve the fluoropolyether group-containing polymer and a partial (hydrolyzed) condensate thereof. The optimum concentration of the fluoropolyether group-containing polymer composition (fluoropolyether group-containing polymer and partial (hydrolyzed) condensate thereof) dissolved in the solvent varies depending on the treatment method, and is preferably from 0.01 to 10 parts by mass, particularly preferably from 0.05 to 5 parts by mass, based on 100 parts by mass of the total of the solvent and the fluoropolyether group-containing polymer composition (fluoropolyether group-containing polymer and partial (hydrolyzed) condensate thereof) in the case of direct coating, and is preferably from 1 to 100 parts by mass, particularly preferably from 3 to 30 parts by mass, based on 100 parts by mass of the total of the solvent and the fluoropolyether group-containing polymer composition (fluoropolyether group-containing polymer and partial (hydrolyzed) condensate thereof) in the case of vapor deposition treatment.
The coating agent of the present invention can be applied to a substrate by a known method such as brushing, dipping, spraying, vapor deposition treatment, or the like. The heating method in the vapor deposition process may be a resistance heating method or an electron beam heating method, and is not particularly limited. The curing temperature varies depending on the curing method, and for example, in the case of direct coating (brushing, dipping, spraying, etc.), it is preferable to conduct the curing at 25 to 200 ℃, particularly 25 to 80 ℃ for 30 minutes to 36 hours, particularly 1 to 24 hours. In addition, when vapor deposition treatment is used, it is preferable to perform the vapor deposition treatment at a temperature in the range of 20 to 200 ℃, particularly 25 to 80 ℃ for 30 minutes to 36 hours, particularly 30 minutes to 24 hours. In addition, it may be cured under humidification. The thickness of the cured coating is appropriately selected depending on the type of the substrate, and is usually 0.1 to 100nm, particularly 1 to 20nm. In addition, for example, in the case of spray coating, if the spray coating is performed after dilution in a fluorine-based solvent to which water has been added in advance and hydrolysis, that is, formation of si—oh, the curing after the coating is fast.
The film thickness can be measured by, for example, a spectroscopic reflectance measurement method, an X-ray reflectance measurement method, an ellipsometry measurement method, a fluorescent X-ray measurement method, or the like.
The substrate treated with the coating agent of the present invention is not particularly limited, and may be a substrate of various materials such as paper, cloth, metal and oxides thereof, glass, plastic, ceramic, quartz, and the like. The coating agent of the present invention can impart water-and oil-repellency and steel wool abrasion resistance to the above-mentioned substrate. In particular, the coating composition can be suitably used as a coating agent for glass or film treated with SiO 2.
Examples of the article treated with the coating agent of the present invention include optical articles such as car navigation, cellular phones, smart phones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game machines, spectacle lenses, camera lenses, lens filters, medical instruments such as sunglasses and gastroscopes, copiers, PCs, liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, and antireflection films. In addition, from the viewpoint of difficulty in sliding, cases of mobile phones, smartphones, PCs, and the like can also be handled. The coating agent of the present invention can prevent fingerprints and sebum from adhering to the above-mentioned articles and further impart scratch resistance (abrasion resistance), and is therefore particularly useful as a water-repellent and oil-repellent layer for housings of mobile phones, smart phones, PCs, and the like.
The coating composition of the present invention can be used as an antifouling coating for sanitary products such as bathtubs and wash-basins, a glass pane or reinforced glass for automobiles, electric cars, airplanes, etc., an antifouling coating for front-lighting lamp covers, a water-repellent and oil-repellent coating for exterior building materials, an oil-repellent coating for kitchen building materials, an antifouling and anti-sticking paper for telephone booth, a coating for graffiti, a coating for artwork, etc., a fingerprint adhesion preventing coating for CDs, DVDs, etc., a mold release agent or coating additive, a resin modifier, a fluidity modifier or dispersibility modifier for inorganic fillers, a water-repellent and oil-repellent agent for tapes, films, etc. Further, from the viewpoint of difficulty in sliding, the present invention is also useful as an antifouling paint for building materials, particularly floor materials and wall materials.
According to the present invention, the coating agent comprising the fluoropolyether-based polymer composition of the present invention is applied and cured to form a layer by using a dry method (vapor deposition treatment) or a wet method (brushing, dipping, spraying, etc.) on the entire surface or a part of the surface of an article, whereby the surface of the article can be modified.
In the case of an article having a layer containing a cured product of the coating agent of the present invention, the dynamic friction coefficient of the surface of the article is preferably 0.13 or more, more preferably 0.18 or more under the following metering conditions. When the dynamic friction coefficient is less than 0.13, the surface of the cured film may be too slippery, and thus the coated article may be insufficiently held and fixed. In the present invention, in order to make the dynamic friction coefficient of the surface of the article equal to or higher than the above-mentioned value, the coating agent of the present invention containing the polymer composition containing a fluoropolyether group can be realized by making 65 mass% or higher of the polymer containing a fluoropolyether group represented by the above-mentioned formula (1).
[ Dynamic Friction coefficient measurement Condition ]
Determination by the method according to ASTM D1894
Load: 100gf
Stroke: 100mm of
Stretching speed: 500 mm/min
Contact area: 1X 3cm 2
Friction material: nonwoven (BEMCOT (manufactured by Asahi chemical Co., ltd.))
Test environmental conditions: 25 ℃ and relative humidity of 50%
In the case of an article having a layer containing a cured product of the coating agent of the present invention, the number of wear durability of the surface of the article is preferably 5000 or more, more preferably 7500 or more under the test conditions described below. In the present invention, in order to make the number of wear durability of the surface of the article equal to or greater than the above value, the coating agent of the present invention containing the polymer composition containing a fluoropolyether group can be realized by making the polymer containing a fluoropolyether group represented by the above formula (2) equal to or greater than 10 mass%.
[ Wear durability test conditions ]
Evaluation of Steel wool abrasion durability Using reciprocating abrasion tester
Friction material: steel wire #0000 (Bons tar)
Load: 1kgf
Reciprocating distance: 40mm
Reciprocating speed: 60 reciprocations per minute
Test environmental conditions: 25 ℃ and relative humidity of 50%
The water contact angle of the frictional worn portion was measured for 2500 times per frictional reciprocation, and the number of times of wear reciprocation at which the water contact angle was maintained at 100 degrees or more was set as the number of times of wear durability.
Examples
The present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to the examples. In the following formula, the film thickness is a value measured by ellipsometry using a spectroscopic ellipsometer.
Examples 1 to 54 and comparative examples 1 to 39
Preparation of coating agent and formation of cured coating film
A fluoropolyether group-containing polymer having a structure represented by the following formulas (A), (B) and (C) as component (I) is reacted with
[ Chemical 41]
[ Chemical 42]
[ Chemical 43]
A fluoropolyether group-containing polymer having a structure represented by the following formulas (D), (E), (F), (G), (H) and (I) as component (II)
[ 44]
(H3CO)3Si-H2CH2CH2C-O-CH2-CF2-o-(CF2O)21(CF2CF2O)21-CF2-CH2-O-CH2CH2CH2-Si(OCH3)3 (D)
[ 45]
[ Chemical 46]
[ 47]
(H3CO)3Si-H2CH2CH2C-O-CH2-CF2-O-(CF2O)p(CF2CF2O)q-CF2-CH2-O-CH2CH2CH2-Si(OCH3)3p/q＝1.03,p+q＝86 (G)
[ 48]
[ 49]
The mixture was mixed in the proportions shown in tables 1,2 and 3 to obtain a polymer composition containing a fluoropolyether group. The polymer composition was dissolved in Novec7200 (manufactured by 3M company, ethyl perfluorobutyl ether) so that the concentration became 20 mass%, to prepare a coating agent. For glass (Gor il 1a manufactured by Corning Co.) having its outermost surface treated with 10nm of Si0 2, 6. Mu.l of each coating agent was vacuum deposited (treatment conditions: 3.0X10 -3 Pa, heating temperature: 500 ℃ C.) and left at 80 ℃ C. In an atmosphere of 80% relative humidity for 30 minutes, and then cured for 12 hours or more in an atmosphere of 25 ℃ C. And 50% relative humidity to form a cured coating film having a film thickness of 13 nm.
[ Evaluation of initial Water repellency ]
The glass with the cured coating formed thereon was measured for the contact angle (water repellency) of the cured coating with respect to water using a contact angle meter Drop Mas (manufactured by co-ordinates interface science co.) (droplet: 2 μl, temperature: 25 ℃ C., relative humidity: 50%). The results (initial water contact angles) are shown in tables 1,2 and 3.
In the initial stage, examples and comparative examples all showed good water repellency of 110 ° or more.
[ Evaluation of slidability ]
As for the glass with a cured coating film formed as described above, the following method was used for evaluating the sliding properties, and the dynamic friction coefficient with respect to the nonwoven fabric was evaluated. Dynamic coefficient of friction for nonwoven fabric of glass having a cured coating formed thereon was measured according to ASTM D1894 using a surface texture measuring machine TYPE:14FW (manufactured by Xindong scientific Co., ltd.) under a load of 100gf and a stretching speed of 500 mm/min. Tables 1,2 and 3 show that the dynamic friction coefficient was 0.23 or more (excellent), 0.18 or more and less than 0.23 was good, 0.13 or more and less than 0.18 was delta (acceptable), and less than 0.13 was X (not acceptable), as an index of evaluation. The test environment conditions were 25℃and relative humidity 50%.
Slidability of the slide
Load: 100gf
Stroke: 100mm of
Contact area: 1X 3cm 2
Nonwoven fabric: BEMCOT (manufactured by Xuhua chemical Co., ltd.)
[ Evaluation of abrasion resistance ]
Evaluation of wear durability of Steel wool
The substrate having the anti-fouling coating film layer (cured film) obtained above was tested under the following conditions using a reciprocating abrasion tester (Type 40, manufactured by new east scientific).
Friction material: steel wire #0000 (Bons tar)
Load: 1kgf
Reciprocating distance: 40mm
Reciprocating speed: 60 reciprocations per minute
Total number of friction reciprocations: 10000 times
The water contact angle of the tribologically worn portion was measured 2500 times per frictional reciprocation. Tables 1,2 and 3 show that the number of abrasion reciprocations for maintaining a water contact angle of 100 ° or more is regarded as the number of steel wool abrasion durable times, that the number of steel wool abrasion durable times is 10000 or more is regarded as excellent, that 7500 or more and less than 10000 is regarded as good, that 5000 or more and less than 7500 is regarded as delta, and that less than 5000 is regarded as x (not possible). The test environment conditions were 25℃and relative humidity 50%.
TABLE 1
TABLE 2
TABLE 3
When the fluoropolyether-based polymer of component (I) is used alone, the dynamic friction coefficient is good, but the abrasion resistance is insufficient. In addition to the fluoropolyether group-containing polymer as the component (I), when the fluoropolyether group-containing polymer having a fluorinated oxyalkylene group in the molecule, a reactive functional group at both ends of the polymer and no polar group is used as the component (I I) in the ratio shown in the examples, the dynamic friction coefficient and abrasion resistance are both good. The following trends were found: if the mixing ratio of the component (I I) with respect to the component (I) is increased, the dynamic friction coefficient and the abrasion resistance are lowered.
Claims (13)
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| JP5669257B2 (en) * | 2009-10-27 | 2015-02-12 | 信越化学工業株式会社 | Fluorooxyalkylene group-containing polymer composition, surface treatment agent containing the composition, and article surface-treated with the surface treatment agent |
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