DE69719330T2 - Überzugsmittel die fluorierte ester enthalten - Google Patents
Überzugsmittel die fluorierte ester enthaltenInfo
- Publication number
- DE69719330T2 DE69719330T2 DE69719330T DE69719330T DE69719330T2 DE 69719330 T2 DE69719330 T2 DE 69719330T2 DE 69719330 T DE69719330 T DE 69719330T DE 69719330 T DE69719330 T DE 69719330T DE 69719330 T2 DE69719330 T2 DE 69719330T2
- Authority
- DE
- Germany
- Prior art keywords
- unsaturated
- mixture
- coating composition
- coating
- ssoy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000011248 coating agent Substances 0.000 title claims description 29
- 229910052731 fluorine Inorganic materials 0.000 title claims description 21
- 239000011737 fluorine Substances 0.000 title claims description 19
- -1 FLUORINE ESTER Chemical class 0.000 title description 24
- 239000000203 mixture Chemical group 0.000 claims description 60
- 239000008199 coating composition Substances 0.000 claims description 58
- 150000002148 esters Chemical class 0.000 claims description 58
- 238000000576 coating method Methods 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 46
- 229920000180 alkyd Polymers 0.000 claims description 31
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 22
- 238000001035 drying Methods 0.000 claims description 20
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 18
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000003892 spreading Methods 0.000 claims description 6
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229920006305 unsaturated polyester Polymers 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 22
- 238000012360 testing method Methods 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 15
- 238000001723 curing Methods 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 238000009838 combustion analysis Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 11
- 239000003973 paint Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 150000004694 iodide salts Chemical class 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 238000006116 polymerization reaction Methods 0.000 description 6
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- 238000006555 catalytic reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- 239000005871 repellent Substances 0.000 description 5
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- FMFKNGWZEQOWNK-UHFFFAOYSA-N 1-butoxypropan-2-yl 2-(2,4,5-trichlorophenoxy)propanoate Chemical compound CCCCOCC(C)OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl FMFKNGWZEQOWNK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
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- 230000001681 protective effect Effects 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 2
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000006701 autoxidation reaction Methods 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 229940043259 farnesol Drugs 0.000 description 2
- 229930002886 farnesol Natural products 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 1
- NTJGOGUJUWAZIB-UPHRSURJSA-N (Z)-2,3-bis(1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctan-2-yl)but-2-enedioic acid Chemical compound C(=C(\C(=O)O)/C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(F)(F)F)F)(\C(=O)O)/C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(F)(F)F)F NTJGOGUJUWAZIB-UPHRSURJSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
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- 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
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- 238000005669 hydrocyanation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 230000005291 magnetic effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- JEGNXMUWVCVSSQ-UHFFFAOYSA-N octadec-1-en-1-ol Chemical class CCCCCCCCCCCCCCCCC=CO JEGNXMUWVCVSSQ-UHFFFAOYSA-N 0.000 description 1
- YQBBOKLKQHKPIW-UHFFFAOYSA-N octadeca-1,3-dien-1-ol Chemical class CCCCCCCCCCCCCCC=CC=CO YQBBOKLKQHKPIW-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- RQFLGKYCYMMRMC-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O RQFLGKYCYMMRMC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical class 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
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester 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
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/695,159 US5670573A (en) | 1996-08-07 | 1996-08-07 | Coatings containing fluorinated esters |
| PCT/US1997/013668 WO1998005720A1 (en) | 1996-08-07 | 1997-08-04 | Coatings containing fluorinated esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69719330D1 DE69719330D1 (de) | 2003-04-03 |
| DE69719330T2 true DE69719330T2 (de) | 2003-09-18 |
Family
ID=24791860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69719330T Expired - Fee Related DE69719330T2 (de) | 1996-08-07 | 1997-08-04 | Überzugsmittel die fluorierte ester enthalten |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5670573A (enExample) |
| EP (1) | EP0917554B1 (enExample) |
| JP (1) | JP2000515579A (enExample) |
| KR (1) | KR100467404B1 (enExample) |
| CN (1) | CN1152936C (enExample) |
| AU (1) | AU730867B2 (enExample) |
| CA (1) | CA2262575C (enExample) |
| DE (1) | DE69719330T2 (enExample) |
| TW (1) | TW373009B (enExample) |
| WO (1) | WO1998005720A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5859126A (en) * | 1995-09-18 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Coatings containing fluorinated esters |
| US6475234B1 (en) | 1998-10-26 | 2002-11-05 | Medinol, Ltd. | Balloon expandable covered stents |
| JP4649689B2 (ja) * | 1999-07-09 | 2011-03-16 | ダイキン工業株式会社 | ポリフルオロアルキルエステル類の製造方法およびこのエステルを用いる含フッ素アクリル共重合体の製造方法 |
| DE19957678A1 (de) * | 1999-12-01 | 2001-06-07 | Nanogate Gmbh | Deckschichtharze |
| FR2812012B1 (fr) * | 2000-07-18 | 2003-06-13 | Lafarge Platres | Plaque de platre a resistance au feu amelioree et sa reparation |
| US7114621B2 (en) * | 2001-12-14 | 2006-10-03 | 3M Innovative Properties Company | Membrane module elements |
| KR100478628B1 (ko) * | 2002-06-20 | 2005-03-23 | 니카코리아 (주) | 무용제 수분산 불소계 에멀젼형 발수발유코팅용액의제조방법 |
| US7279215B2 (en) * | 2003-12-03 | 2007-10-09 | 3M Innovative Properties Company | Membrane modules and integrated membrane cassettes |
| US20070212491A1 (en) * | 2006-03-08 | 2007-09-13 | Yen Jessica C | Fluorochemical and lecithin additive for coatings |
| US20070212560A1 (en) * | 2006-03-08 | 2007-09-13 | Yen Jessica C | Fluorochemical and lecithin additive for coatings |
| KR100773135B1 (ko) * | 2006-12-21 | 2007-11-02 | (주)디피아이 홀딩스 | 수용성 도료 및 이를 이용한 도막 형성 방법 |
| CN102936448B (zh) * | 2012-11-23 | 2014-10-22 | 杭州市萧山区党山新世纪装饰卫浴研发中心 | 一种耐沾污人造石台盆表面保护材料 |
| MX2017005336A (es) | 2014-10-28 | 2017-08-15 | 3M Innovative Properties Co | Componentes de un sistema de aplicacion por pulverizacion que comprende una superficie repelente y metodos. |
| EP3368618B1 (en) | 2015-10-28 | 2020-11-25 | 3M Innovative Properties Company | Articles subject to ice formation comprising a repellent surface |
| BR112018008646A2 (pt) | 2015-10-28 | 2018-10-30 | 3M Innovative Properties Co | componentes de um sistema de aplicação de aspersões que compreende uma superfície repelente e métodos |
| JP2019512568A (ja) * | 2016-03-03 | 2019-05-16 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | 建築用コーティングのためのフッ素化エステル化合物添加剤 |
| JP6910365B2 (ja) * | 2016-03-03 | 2021-07-28 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | 建築用コーティングのための部分フッ素化エステル化合物添加剤 |
| EP3448944A4 (en) | 2016-04-26 | 2019-11-13 | 3M Innovative Properties Company | ARTISTS SUBJECT TO ICE FORMATION WITH A REPELLENT SURFACE COMPRISING SILOXONE MATERIAL |
| US11518894B2 (en) | 2017-06-26 | 2022-12-06 | The Chemours Company Fc, Llc | Fluorinated ester compound additives for architectural coatings |
| ES2908709T3 (es) | 2017-12-26 | 2022-05-03 | Akzo Nobel Coatings Int Bv | Un polímero de éter fluorado, su método de preparación y uso del mismo |
| CN112557540A (zh) * | 2020-12-04 | 2021-03-26 | 南通市产品质量监督检验所 | 一种气质联用法测定记忆保健枕中甲苯-2，6-二异氰酸酯的方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE634770A (enExample) * | 1961-05-03 | |||
| US3462296A (en) * | 1966-07-22 | 1969-08-19 | Du Pont | Fluorinated oil- and water-repellent copolymer and process for treating fibrous materials with said copolymer |
| US3491169A (en) * | 1966-07-22 | 1970-01-20 | Du Pont | Oil and water repellent |
| US3923715A (en) * | 1973-07-26 | 1975-12-02 | Du Pont | Aqueous dispersions of perfluoroalkyl esters and vinyl polymers for treating textiles |
| JPS5047912A (enExample) * | 1973-08-24 | 1975-04-28 | ||
| US4054592A (en) * | 1974-02-04 | 1977-10-18 | Ciba-Geigy Corporation | Urethanes containing two perfluoroalkylthio groups |
| US4097642A (en) * | 1975-11-12 | 1978-06-27 | Ciba-Geigy Corporation | Fabric coated with RF-glycols containing two perfluoroalkylthio groups |
| DE2821495C2 (de) * | 1978-05-17 | 1984-06-28 | Battelle-Institut E.V., 6000 Frankfurt | Mittel zur Antischmutzausrüstung von Lacken |
| DK162979C (da) * | 1981-06-26 | 1992-06-01 | Du Pont | Polyfluoralkylestere, deres fremstilling og anvendelse |
| US4401780A (en) * | 1982-02-03 | 1983-08-30 | Minnesota Mining And Manufacturing Company | Textile treatments |
| FR2540131B1 (fr) * | 1983-01-28 | 1986-04-04 | Atochem | Compositions et procede pour le traitement oleophobe et hydrophobe des materiaux de construction |
| US4539006A (en) * | 1983-09-13 | 1985-09-03 | Minnesota Mining And Manufacturing Company | Leather treatment |
| US4958039A (en) * | 1984-08-24 | 1990-09-18 | E. I. Du Pont De Nemours And Company | Modified fluorocarbonylimino biurets |
| JPS61240430A (ja) * | 1985-04-18 | 1986-10-25 | Tdk Corp | 磁気記録媒体 |
| US4595518A (en) * | 1985-07-10 | 1986-06-17 | E. I. Du Pont De Nemours And Company | Coating fibrous substrates with fluoropolymer amphoteric polymer and surfactants |
| CA1297738C (en) * | 1986-01-09 | 1992-03-24 | Hirofumi Kondo | Magnetic recording medium |
| US4946992A (en) * | 1988-06-20 | 1990-08-07 | Ciba-Geigy Corporation | Heteroatom containing perfluoroalkyl terminated neopentyl glycols and compositions therefrom |
| US5350878A (en) * | 1989-07-26 | 1994-09-27 | Dow Corning Corporation | Fluorinated compounds containing hetero atoms and polymers thereof |
| JPH03167158A (ja) * | 1989-11-27 | 1991-07-19 | Hitachi Maxell Ltd | 脂肪族カルボン酸フルオロ基含有アルキルエステル誘導体および脂肪族カルボン酸フルオロ基含有アルキルエステル誘導体を含む潤滑剤 |
| JP3114992B2 (ja) * | 1990-06-04 | 2000-12-04 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 官能化トリフルオロビニルエーテル類およびそれらのポリマー類 |
| US5087672A (en) * | 1990-06-13 | 1992-02-11 | Minnesota Mining And Manufacturing Company | Fluorine-containing acrylate and methacrylate side-chain liquid crystal monomers and polymers |
| US5188747A (en) * | 1990-09-04 | 1993-02-23 | Matsushita Electric Industrial Co., Ltd. | Fluorine-containing lubricant compounds |
| FR2683535B1 (fr) * | 1991-11-12 | 1994-10-28 | Atochem | Nouveaux copolymeres fluores et leur utilisation pour le revetement et l'impregnation de substrats divers. |
| JPH05232718A (ja) * | 1992-02-21 | 1993-09-10 | Mitsubishi Kasei Corp | 電子写真感光体 |
| JPH05246951A (ja) * | 1992-03-06 | 1993-09-24 | Kuraray Co Ltd | フッ素含有化合物 |
| CZ282973B6 (cs) * | 1993-03-09 | 1997-11-12 | Elf Atochem S.A. | Způsob výroby halogenovaných esterů karboxylových nebo dikarboxylových kyselin |
| EP0694532B1 (en) * | 1994-07-01 | 2000-05-31 | Ciba SC Holding AG | Perfluoroalkyl sulfide, sulfone, polysulfone and polysulfide diols |
| US5859126A (en) * | 1995-09-18 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Coatings containing fluorinated esters |
-
1996
- 1996-08-07 US US08/695,159 patent/US5670573A/en not_active Expired - Lifetime
-
1997
- 1997-07-23 TW TW086110504A patent/TW373009B/zh not_active IP Right Cessation
- 1997-08-04 AU AU38263/97A patent/AU730867B2/en not_active Ceased
- 1997-08-04 JP JP10508142A patent/JP2000515579A/ja active Pending
- 1997-08-04 CN CNB97198588XA patent/CN1152936C/zh not_active Expired - Fee Related
- 1997-08-04 CA CA002262575A patent/CA2262575C/en not_active Expired - Fee Related
- 1997-08-04 EP EP97935291A patent/EP0917554B1/en not_active Expired - Lifetime
- 1997-08-04 WO PCT/US1997/013668 patent/WO1998005720A1/en not_active Ceased
- 1997-08-04 DE DE69719330T patent/DE69719330T2/de not_active Expired - Fee Related
- 1997-08-04 KR KR10-1999-7001028A patent/KR100467404B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2262575A1 (en) | 1998-02-12 |
| AU3826397A (en) | 1998-02-25 |
| JP2000515579A (ja) | 2000-11-21 |
| CA2262575C (en) | 2007-02-20 |
| CN1232484A (zh) | 1999-10-20 |
| DE69719330D1 (de) | 2003-04-03 |
| TW373009B (en) | 1999-11-01 |
| EP0917554A1 (en) | 1999-05-26 |
| KR100467404B1 (ko) | 2005-01-24 |
| US5670573A (en) | 1997-09-23 |
| WO1998005720A1 (en) | 1998-02-12 |
| KR20000029864A (ko) | 2000-05-25 |
| AU730867B2 (en) | 2001-03-15 |
| EP0917554B1 (en) | 2003-02-26 |
| CN1152936C (zh) | 2004-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |