RU2519730C2 - Фторсодержащие выравнивающие средства - Google Patents
Фторсодержащие выравнивающие средства Download PDFInfo
- Publication number
- RU2519730C2 RU2519730C2 RU2010138842/04A RU2010138842A RU2519730C2 RU 2519730 C2 RU2519730 C2 RU 2519730C2 RU 2010138842/04 A RU2010138842/04 A RU 2010138842/04A RU 2010138842 A RU2010138842 A RU 2010138842A RU 2519730 C2 RU2519730 C2 RU 2519730C2
- Authority
- RU
- Russia
- Prior art keywords
- meth
- alkyl
- copolymer
- monomers
- acrylate
- Prior art date
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 34
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 5
- 229910052731 fluorine Inorganic materials 0.000 title description 5
- 239000011737 fluorine Substances 0.000 title description 5
- 239000000178 monomer Substances 0.000 claims abstract description 67
- 229920001577 copolymer Polymers 0.000 claims abstract description 32
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 22
- 239000008199 coating composition Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229920005989 resin Polymers 0.000 claims abstract description 18
- 239000011347 resin Substances 0.000 claims abstract description 18
- 239000011230 binding agent Substances 0.000 claims abstract description 9
- 150000003926 acrylamides Chemical class 0.000 claims abstract description 7
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims abstract description 6
- 238000000576 coating method Methods 0.000 claims description 43
- -1 2,2,3,3,3-pentafluoropropyl Chemical group 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- 239000003999 initiator Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 22
- 238000010526 radical polymerization reaction Methods 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000012634 fragment Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical group [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 230000000977 initiatory effect Effects 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 3
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- MJPPGVVIDGQOQT-UHFFFAOYSA-N 2-bromo-5-(2-bromo-2-nitroethenyl)furan Chemical compound [O-][N+](=O)C(Br)=CC1=CC=C(Br)O1 MJPPGVVIDGQOQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 150000002432 hydroperoxides Chemical class 0.000 claims description 2
- 229920005684 linear copolymer Polymers 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 2
- 101710141544 Allatotropin-related peptide Proteins 0.000 claims 2
- QAXDVKBGZRMSHF-UHFFFAOYSA-N 6-acetyl-5-hydroxy-4-methoxy-7,8-dihydro-3h-pyrrolo[3,2-e]indole-2-carboxylic acid Chemical compound C1=2C=C(C(O)=O)NC=2C(OC)=C(O)C2=C1CCN2C(C)=O QAXDVKBGZRMSHF-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 description 21
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 239000000654 additive Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 229920001400 block copolymer Polymers 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 7
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 229940105994 ethylhexyl acetate Drugs 0.000 description 4
- 238000013467 fragmentation Methods 0.000 description 4
- 238000006062 fragmentation reaction Methods 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 4
- DFVPUWGVOPDJTC-UHFFFAOYSA-N 2,2,3,4,4,4-hexafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)C(F)(F)F DFVPUWGVOPDJTC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- CLISWDZSTWQFNX-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)F CLISWDZSTWQFNX-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 0 CCC(C)(CC(C(C)C1(C)CC)=O)*1OC(C)c1ccccc1 Chemical compound CCC(C)(CC(C(C)C1(C)CC)=O)*1OC(C)c1ccccc1 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- XJOUCILNLRXRTF-UHFFFAOYSA-N 1,2,3,4,5,6-hexakis(bromomethyl)benzene Chemical compound BrCC1=C(CBr)C(CBr)=C(CBr)C(CBr)=C1CBr XJOUCILNLRXRTF-UHFFFAOYSA-N 0.000 description 1
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical group BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 1
- FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical group ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 1
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- AQQNNAXBGPWALO-UHFFFAOYSA-N 2-[butyl(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl)amino]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN(CCCC)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AQQNNAXBGPWALO-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OAAGDVLVOKMRCQ-UHFFFAOYSA-N 5-piperidin-4-yl-3-pyridin-4-yl-1,2,4-oxadiazole Chemical compound C1CNCCC1C1=NC(C=2C=CN=CC=2)=NO1 OAAGDVLVOKMRCQ-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920005692 JONCRYL® Polymers 0.000 description 1
- 229920003264 Maprenal® Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- VDLOXZRCFJZRJH-UHFFFAOYSA-N benzyl ethanedithioate Chemical compound CC(=S)SCC1=CC=CC=C1 VDLOXZRCFJZRJH-UHFFFAOYSA-N 0.000 description 1
- AGCPVOYGTAIJAP-UHFFFAOYSA-N benzyl pyrrole-1-carbodithioate Chemical compound C1=CC=CN1C(=S)SCC1=CC=CC=C1 AGCPVOYGTAIJAP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012711 chain transfer polymerization Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical class C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/24—Homopolymers or copolymers of amides or imides
- C09D133/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/47—Levelling agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08151780.7 | 2008-02-22 | ||
| EP08151780 | 2008-02-22 | ||
| PCT/EP2009/051180 WO2009103613A1 (en) | 2008-02-22 | 2009-02-03 | Fluoro levelling agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010138842A RU2010138842A (ru) | 2012-03-27 |
| RU2519730C2 true RU2519730C2 (ru) | 2014-06-20 |
Family
ID=39720237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010138842/04A RU2519730C2 (ru) | 2008-02-22 | 2009-02-03 | Фторсодержащие выравнивающие средства |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8669336B2 (enExample) |
| EP (1) | EP2247678B1 (enExample) |
| JP (1) | JP5591125B2 (enExample) |
| KR (1) | KR101560854B1 (enExample) |
| CN (1) | CN101952379B (enExample) |
| AT (1) | ATE535581T1 (enExample) |
| BR (1) | BRPI0907194A2 (enExample) |
| RU (1) | RU2519730C2 (enExample) |
| WO (1) | WO2009103613A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101734588B1 (ko) | 2009-01-14 | 2017-05-11 | 바스프 에스이 | 액체 광개시제 혼합물 |
| EP2387600B1 (en) | 2009-01-19 | 2014-04-02 | Basf Se | Organic black pigments and their preparation |
| JP2013527286A (ja) * | 2010-05-19 | 2013-06-27 | エヴォニク ゴールドシュミット ゲーエムベーハー | ポリシロキサンブロックコポリマーおよび化粧料配合物におけるその使用 |
| WO2012107249A1 (de) * | 2011-02-09 | 2012-08-16 | Basf Coatings Gmbh | Verfahren zur herstellung einer farb- und /oder effektgebenden mehrschichtigen lackierung |
| CN102153902B (zh) * | 2011-03-11 | 2013-05-29 | 安徽嘉智信诺化工有限公司 | 一种涂料油墨用氟碳抗缩孔流平剂 |
| CN102268108B (zh) * | 2011-05-13 | 2013-04-10 | 中科院广州化学有限公司 | 一种含氟丙烯酸酯型atrp小分子引发剂及其制备方法 |
| FR2986004B1 (fr) * | 2012-01-25 | 2014-03-14 | Seppic Sa | Nouveau polymere epaississant reduisant le caractere collant des formules cosmetiques a base de glycerine |
| EP3778768A1 (en) | 2012-02-23 | 2021-02-17 | Basf Se | Fluorinated acrylate block copolymers with low dynamic surface tension |
| CN104736583B (zh) * | 2012-10-04 | 2017-03-15 | 巴斯夫涂料有限公司 | 含氟非水性涂料组合物、涂覆方法和涂料组合物的用途 |
| JP2015214614A (ja) * | 2014-05-08 | 2015-12-03 | 日立化成株式会社 | ブロックポリマ及びその製造方法 |
| EP3233785A1 (de) * | 2014-12-19 | 2017-10-25 | Merck Patent GmbH | Fluorverbindungen |
| CN106366233B (zh) * | 2016-08-24 | 2019-04-05 | 六安科瑞达新型材料有限公司 | 一种疏水耐污功能固体丙烯酸消光树脂 |
| CN106279500A (zh) * | 2016-08-24 | 2017-01-04 | 六安科瑞达新型材料有限公司 | 一种高光疏水耐污功能固体丙烯酸树脂 |
| CN111278934B (zh) | 2017-10-23 | 2022-04-12 | 巴斯夫欧洲公司 | 硅氧烷聚合物水乳液 |
| CN109627403B (zh) * | 2018-12-11 | 2021-01-05 | 三明学院 | 一种短碳链含氟嵌段聚合物、制备方法及其应用 |
| CN110357996B (zh) * | 2019-07-31 | 2021-11-09 | 三明学院 | 一种用作流平剂的聚合物及其制备方法和应用 |
| CN110818826B (zh) * | 2019-10-29 | 2021-06-01 | 六安捷通达新材料有限公司 | 一种有机硅氟类流平剂及其制备工艺 |
| BE1027888B1 (nl) * | 2019-12-19 | 2021-07-27 | Unilin Bv | Gebruik van een coating materiaal op de randen van decoratieve panelen en werkwijze |
| JP2023538760A (ja) | 2020-08-25 | 2023-09-11 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | フッ素含有ポリマー |
| CN113176707B (zh) * | 2021-04-29 | 2024-08-16 | 湖南朝泰建材有限公司 | 一种感光干膜及其制备方法 |
| US20240287281A1 (en) | 2021-05-12 | 2024-08-29 | Basf Se | Compositions, comprising platelet-shaped transition metal particles |
| WO2023072740A1 (en) | 2021-10-26 | 2023-05-04 | Basf Se | A method for producing interference elements |
| CN115260803A (zh) * | 2022-08-02 | 2022-11-01 | 百草边大生物科技(青岛)有限公司 | 一种植物改性抗菌抗病毒大生物无机装饰涂料制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006074969A1 (en) * | 2005-01-11 | 2006-07-20 | Ciba Specialty Chemicals Holding Inc. | Process for the post-modification of homo and copolymers prepared by controlled free radical polymerization processes |
| RU2006124517A (ru) * | 2003-12-10 | 2008-01-27 | Циба Спешиалти Кемикэлз Холдинг Инк. (Ch) | Композиции покрытий, содержащие выравнивающие агенты, полученные полимеризацией, опосредуемой нитроксилом |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52155679A (en) * | 1976-06-21 | 1977-12-24 | Mitsubishi Rayon Co | Plastic moulding with metallic film and method of its manufacturing |
| WO2003027159A2 (en) | 2001-09-27 | 2003-04-03 | Ppg Industries Ohio, Inc. | Compositions containing a low surface tension (meth)acrylate containing block copolymer |
| US6841641B2 (en) | 2001-09-27 | 2005-01-11 | Ppg Industries Ohio, Inc. | Copolymers comprising low surface tension (meth) acrylates |
| AT410944B (de) | 2001-11-30 | 2003-08-25 | Solutia Austria Gmbh | Additive für pulverlacke |
| EP1333072A3 (en) * | 2002-01-30 | 2003-11-12 | Rohm And Haas Company | Ink composition |
| JP4147245B2 (ja) | 2003-07-08 | 2008-09-10 | 共栄社化学株式会社 | コーティング剤用表面張力制御剤およびそれを含有するコーティング剤 |
| JP2006063132A (ja) * | 2004-08-25 | 2006-03-09 | Fuji Photo Film Co Ltd | 有機溶剤系塗布改良剤 |
| CA2633263A1 (en) * | 2005-12-16 | 2007-07-12 | Arkema Inc. | Low surface energy block co-polymer preparation methods and applications |
| JP2007191507A (ja) * | 2006-01-17 | 2007-08-02 | Kyoeisha Chem Co Ltd | コーティング剤組成物 |
-
2009
- 2009-02-03 WO PCT/EP2009/051180 patent/WO2009103613A1/en not_active Ceased
- 2009-02-03 US US12/867,770 patent/US8669336B2/en not_active Expired - Fee Related
- 2009-02-03 JP JP2010547141A patent/JP5591125B2/ja not_active Expired - Fee Related
- 2009-02-03 RU RU2010138842/04A patent/RU2519730C2/ru not_active IP Right Cessation
- 2009-02-03 CN CN200980106000.7A patent/CN101952379B/zh not_active Expired - Fee Related
- 2009-02-03 EP EP09713532A patent/EP2247678B1/en not_active Not-in-force
- 2009-02-03 BR BRPI0907194-6A patent/BRPI0907194A2/pt not_active IP Right Cessation
- 2009-02-03 KR KR1020107021094A patent/KR101560854B1/ko not_active Expired - Fee Related
- 2009-02-03 AT AT09713532T patent/ATE535581T1/de active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2006124517A (ru) * | 2003-12-10 | 2008-01-27 | Циба Спешиалти Кемикэлз Холдинг Инк. (Ch) | Композиции покрытий, содержащие выравнивающие агенты, полученные полимеризацией, опосредуемой нитроксилом |
| WO2006074969A1 (en) * | 2005-01-11 | 2006-07-20 | Ciba Specialty Chemicals Holding Inc. | Process for the post-modification of homo and copolymers prepared by controlled free radical polymerization processes |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2247678B1 (en) | 2011-11-30 |
| EP2247678A1 (en) | 2010-11-10 |
| RU2010138842A (ru) | 2012-03-27 |
| JP5591125B2 (ja) | 2014-09-17 |
| US20110040018A1 (en) | 2011-02-17 |
| US8669336B2 (en) | 2014-03-11 |
| WO2009103613A1 (en) | 2009-08-27 |
| CN101952379B (zh) | 2014-02-26 |
| CN101952379A (zh) | 2011-01-19 |
| KR101560854B1 (ko) | 2015-10-15 |
| KR20100117126A (ko) | 2010-11-02 |
| JP2011514920A (ja) | 2011-05-12 |
| BRPI0907194A2 (pt) | 2015-07-14 |
| ATE535581T1 (de) | 2011-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2247678B1 (en) | Fluoro levelling agents | |
| US9944786B2 (en) | Method to lower the dynamic surface tension of a composition | |
| JP2002179991A (ja) | 表面コーティング用レベリング剤 | |
| JP2004043804A (ja) | 塗料組成物用レベリング剤 | |
| JP5296506B2 (ja) | 防錆塗料用エマルション | |
| JP2010539259A (ja) | 粉末塗装レベリング剤としてのポリプロピレンオキシド含有ポリエーテルおよびそれらのポリ（メタ）アクリル酸エステルとの混合物 | |
| TW200528511A (en) | Acrylic compositions | |
| JP6207071B2 (ja) | 艶消し遮熱塗料組成物及び該組成物を用いた塗膜形成方法 | |
| JP2010100706A (ja) | 水性塗料用のワキ防止剤 | |
| CN107075122A (zh) | 用于涂料组合物的流动改性剂 | |
| JPH07216241A (ja) | 不粘着性、耐引掻性で且つ耐薬品性の塗料のためのバインダーとしてのポリマー水性分散物 | |
| JP2006052284A (ja) | トリオルガノシリル基含有樹脂水分散体の製造方法 | |
| CA3122298C (en) | PRIMER WITH INTERNAL GUIDING LAYER | |
| JP2021091833A (ja) | 水性樹脂エマルション | |
| JP5343194B2 (ja) | 粘性改良剤 | |
| JP5555772B2 (ja) | ランダムに分枝したコポリマー、その調製及びコーティング材料中のレベリング剤としてのその使用 | |
| JP2000510500A (ja) | 放射線硬化型被覆材料 | |
| JP5347093B2 (ja) | 粘性改良剤 | |
| Bouscher | Advancements in Powder Coating Processing and in Real-time Film Formation Analysis of Thermoset Coatings | |
| JP2005248171A (ja) | 傾斜組成塗膜形成用被覆用組成物 | |
| JP2003096264A (ja) | 水性ハイソリッド型熱硬化性樹脂組成物 | |
| JP2009114347A (ja) | 粘性改良剤 | |
| JP2000309727A (ja) | 艶消し塗料用樹脂組成物及び塗料 | |
| JPH11263928A (ja) | 塗料組成物 | |
| JP2017057309A (ja) | 樹脂付着アルミニウム顔料、塗料、及びインキ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20160204 |