AU756298B2 - Silicon reactive oligomers and coating compositions made therefrom - Google Patents
Silicon reactive oligomers and coating compositions made therefrom Download PDFInfo
- Publication number
- AU756298B2 AU756298B2 AU24932/99A AU2493299A AU756298B2 AU 756298 B2 AU756298 B2 AU 756298B2 AU 24932/99 A AU24932/99 A AU 24932/99A AU 2493299 A AU2493299 A AU 2493299A AU 756298 B2 AU756298 B2 AU 756298B2
- Authority
- AU
- Australia
- Prior art keywords
- silicon
- composition
- hydroxyl
- groups
- oligomer
- 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.)
- Ceased
Links
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 96
- 229910052710 silicon Inorganic materials 0.000 title claims description 96
- 239000010703 silicon Substances 0.000 title claims description 96
- 239000008199 coating composition Substances 0.000 title claims description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 121
- 238000000034 method Methods 0.000 claims description 58
- 238000000576 coating method Methods 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 54
- 239000011248 coating agent Substances 0.000 claims description 48
- 229920000058 polyacrylate Polymers 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 28
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 27
- -1 hydrOxy Chemical class 0.000 claims description 27
- 238000004132 cross linking Methods 0.000 claims description 26
- 239000004971 Cross linker Substances 0.000 claims description 23
- 229910000077 silane Inorganic materials 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 18
- 239000012948 isocyanate Substances 0.000 claims description 18
- 150000002513 isocyanates Chemical class 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 9
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229920000608 Polyaspartic Polymers 0.000 claims description 2
- 150000004705 aldimines Chemical class 0.000 claims description 2
- 150000004658 ketimines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 150000003606 tin compounds Chemical class 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 6
- 101100291385 Drosophila melanogaster p38a gene Proteins 0.000 claims 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000000178 monomer Substances 0.000 description 14
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 14
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 13
- 238000005227 gel permeation chromatography Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000004756 silanes Chemical class 0.000 description 11
- 239000013638 trimer Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 9
- 239000012975 dibutyltin dilaurate Substances 0.000 description 9
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 9
- 229920000647 polyepoxide Polymers 0.000 description 9
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 5
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 5
- 239000005052 trichlorosilane Substances 0.000 description 5
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 4
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 4
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
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- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 3
- FERWBXLFSBWTDE-UHFFFAOYSA-N 3-aminobutan-2-ol Chemical compound CC(N)C(C)O FERWBXLFSBWTDE-UHFFFAOYSA-N 0.000 description 3
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- HZGIOLNCNORPKR-UHFFFAOYSA-N n,n'-bis(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCC[Si](OC)(OC)OC HZGIOLNCNORPKR-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- SHHGHQXPESZCQA-UHFFFAOYSA-N oxiran-2-ylmethylsilicon Chemical compound [Si]CC1CO1 SHHGHQXPESZCQA-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- AJMJSPWGPLXRSJ-UHFFFAOYSA-N silyl but-3-enoate Chemical class [SiH3]OC(=O)CC=C AJMJSPWGPLXRSJ-UHFFFAOYSA-N 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- BACYXSNZANMSGE-UHFFFAOYSA-N trichloro(2-cyclohex-3-en-1-ylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CCC1CCC=CC1 BACYXSNZANMSGE-UHFFFAOYSA-N 0.000 description 1
- FASXEYZULXXNRF-UHFFFAOYSA-N trichloro-[2-(4-trichlorosilylcyclohexyl)ethyl]silane Chemical compound Cl[Si](Cl)(Cl)CCC1CCC([Si](Cl)(Cl)Cl)CC1 FASXEYZULXXNRF-UHFFFAOYSA-N 0.000 description 1
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 description 1
- SHCGUUKICQTMGF-UHFFFAOYSA-N trimethoxy(8-trimethoxysilyloctyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCCC[Si](OC)(OC)OC SHCGUUKICQTMGF-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3212—Polyhydroxy compounds containing cycloaliphatic groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- 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
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/423—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4261—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups prepared by oxyalkylation of polyesterpolyols
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
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- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4692—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6295—Polymers of silicium containing compounds having carbon-to-carbon double bonds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7391298P | 1998-02-06 | 1998-02-06 | |
| US60/073912 | 1998-02-06 | ||
| PCT/US1999/002266 WO1999040140A1 (en) | 1998-02-06 | 1999-02-03 | Silicon reactive oligomers and coating compositions made therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2493299A AU2493299A (en) | 1999-08-23 |
| AU756298B2 true AU756298B2 (en) | 2003-01-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU24932/99A Ceased AU756298B2 (en) | 1998-02-06 | 1999-02-03 | Silicon reactive oligomers and coating compositions made therefrom |
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| EP (1) | EP1054916B1 (enExample) |
| JP (1) | JP2002502902A (enExample) |
| KR (1) | KR100564200B1 (enExample) |
| AU (1) | AU756298B2 (enExample) |
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| ES (1) | ES2255244T3 (enExample) |
| IL (1) | IL137075A0 (enExample) |
| NZ (1) | NZ505793A (enExample) |
| TW (1) | TW483927B (enExample) |
| WO (1) | WO1999040140A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20040077778A1 (en) * | 2002-08-07 | 2004-04-22 | Isidor Hazan | One-pack primer sealer compositions for SMC automotive body panels |
| US7771609B2 (en) | 2002-08-16 | 2010-08-10 | Aerogel Technologies, Llc | Methods and compositions for preparing silica aerogels |
| US20040071953A1 (en) * | 2002-09-30 | 2004-04-15 | Sobieski Robert T. | Ink formulations and methods |
| US6849682B2 (en) * | 2002-09-30 | 2005-02-01 | Omnova Solutions Inc. | VOC containment coating, methods and articles |
| CN1886232A (zh) * | 2003-11-26 | 2006-12-27 | 3M创新有限公司 | 研磨工件的方法 |
| WO2005105939A1 (en) * | 2004-04-27 | 2005-11-10 | E.I. Dupont De Nemours And Company | Preparation and use of reactive organosilicon compounds |
| US20050238899A1 (en) * | 2004-04-27 | 2005-10-27 | Isao Nagata | High solids clearcoat compositions containing silane functional compounds |
| US7732496B1 (en) | 2004-11-03 | 2010-06-08 | Ohio Aerospace Institute | Highly porous and mechanically strong ceramic oxide aerogels |
| US7858190B2 (en) | 2005-09-15 | 2010-12-28 | Basf Coatings Gmbh | Thermosetting coating compositions with multiple cure mechanisms |
| US20070243798A1 (en) * | 2006-04-18 | 2007-10-18 | 3M Innovative Properties Company | Embossed structured abrasive article and method of making and using the same |
| US7410413B2 (en) * | 2006-04-27 | 2008-08-12 | 3M Innovative Properties Company | Structured abrasive article and method of making and using the same |
| ES2672628T3 (es) | 2006-05-16 | 2018-06-15 | Coatings Foreign Ip Co. Llc | Composición de recubrimiento altamente productiva para la renovación del acabado de automóviles |
| MX325549B (es) * | 2006-06-14 | 2014-11-24 | Du Pont | Sustrato recubierto que tiene resistencia mejorada contra ralladuras y desgaste. |
| US9051473B2 (en) | 2006-06-14 | 2015-06-09 | Axalta Coating Systems Ip Co., Llc | Clear coating compositions comprising dispersed silica nono-particles and processes for using |
| US8207252B2 (en) | 2007-03-07 | 2012-06-26 | Momentive Performance Materials Inc. | Moisture-curable silylated polymer resin composition |
| US8206827B2 (en) * | 2007-03-15 | 2012-06-26 | Nanovere Technologies, Llc | Dendritic polyurethane coating |
| US8568888B2 (en) | 2007-03-15 | 2013-10-29 | Nanovere Technologies, Inc. | Dendritic polyurethane coating |
| US7569645B2 (en) * | 2007-06-27 | 2009-08-04 | Momentive Performance Materials Inc. | Curable silyl-containing polymer composition containing paint adhesion additive |
| US8038750B2 (en) | 2007-07-13 | 2011-10-18 | 3M Innovative Properties Company | Structured abrasive with overlayer, and method of making and using the same |
| US8314201B2 (en) | 2007-11-30 | 2012-11-20 | The United States Of America As Represented By The Administration Of The National Aeronautics And Space Administration | Highly porous ceramic oxide aerogels having improved flexibility |
| US8258251B2 (en) * | 2007-11-30 | 2012-09-04 | The United States Of America, As Represented By The Administrator Of The National Aeronautics And Space Administration | Highly porous ceramic oxide aerogels having improved flexibility |
| CN101925441B (zh) * | 2007-12-31 | 2013-08-14 | 3M创新有限公司 | 经等离子处理的磨料制品及其制造方法 |
| WO2009137929A1 (en) * | 2008-05-12 | 2009-11-19 | Superior Finishes Inc. | Siliconated polyesters and polyacrylates having a low voc |
| CN101579672A (zh) * | 2008-05-16 | 2009-11-18 | 3M创新有限公司 | 用于提高亲水性/透射率的二氧化硅涂层 |
| US20100092765A1 (en) * | 2008-10-10 | 2010-04-15 | 3M Innovative Properties Company | Silica coating for enhanced hydrophilicity |
| US9206335B2 (en) | 2008-10-10 | 2015-12-08 | 3M Innovation Properties Company | Silica coating for enhanced hydrophilicity |
| US8633263B2 (en) | 2009-03-31 | 2014-01-21 | 3M Innovative Properties Company | Coating composition and method of making and using the same |
| CN101941001B (zh) | 2009-07-03 | 2014-04-02 | 3M创新有限公司 | 亲水涂层、制品、涂料组合物和方法 |
| DE102009027623A1 (de) * | 2009-07-10 | 2011-01-13 | Evonik Röhm Gmbh | Halogenfreie Heißversiegelungsmasse für Aluminiumfolien gegen Polyvinylchlorid- und Polystyrolbehälter |
| WO2011006530A1 (en) * | 2009-07-14 | 2011-01-20 | Abb Research Ltd | Epoxy resin composition |
| US8348723B2 (en) * | 2009-09-16 | 2013-01-08 | 3M Innovative Properties Company | Structured abrasive article and method of using the same |
| CN102241899B (zh) | 2010-05-11 | 2014-05-14 | 3M创新有限公司 | 涂料组合物，改性基体表面的方法和制品 |
| US20140242399A1 (en) | 2011-10-27 | 2014-08-28 | Dsm Ip Assets B.V. | Polymer, compositions and process for preparing them |
| US20130165556A1 (en) * | 2011-12-22 | 2013-06-27 | Seung-Man Noh | Highly scratch resistant one-part clear coating composition comprising silane-modified blocked isocyanate for cars |
| EP2735578A1 (de) * | 2012-11-26 | 2014-05-28 | Evonik Industries AG | Beschichtungsmittel mit hoher Kratzbeständigkeit |
| EP2676982A1 (de) * | 2012-06-20 | 2013-12-25 | Evonik Industries AG | Beschichtungsmittel mit hoher Kratzbeständigkeit |
| EP2864383B1 (de) | 2012-06-20 | 2019-10-02 | Evonik Degussa GmbH | Beschichtungsmittel mit hoher kratzbeständigkeit |
| EP2866974B1 (en) | 2012-06-27 | 2017-07-26 | 3M Innovative Properties Company | Abrasive article |
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| KR102521247B1 (ko) * | 2018-08-02 | 2023-04-12 | 아크조노벨코팅스인터내셔널비.브이. | 소프트-필, 방오 코팅을 위한 폴리실록산-변형된 폴리우레탄을 포함하는 코팅 조성물 |
| CN111378346A (zh) * | 2019-01-01 | 2020-07-07 | 中环海化(厦门)船舶智能涂料有限公司 | 一种防腐耐候功能一体化水性石墨烯涂料及其制备方法 |
| CN116157477A (zh) * | 2020-08-04 | 2023-05-23 | 关西涂料株式会社 | 具有高固含量的涂料组合物和用于形成多层涂膜的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997044402A1 (en) * | 1996-05-17 | 1997-11-27 | E.I. Du Pont De Nemours And Company | Mar-resistant oligomeric-based coatings |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4732929A (en) | 1983-01-31 | 1988-03-22 | Ppg Industries, Inc. | Silicon-containing polyols |
| US4804732A (en) * | 1986-01-06 | 1989-02-14 | E. I. Du Pont De Nemours And Company | Polysiloxane graft copolymers, flexible coating compositions comprising same and branched polysiloxane macromers for preparing same |
| DE4491656T1 (de) * | 1993-03-19 | 1995-10-05 | Mazda Motor | Harzzusammensetzung vom Typ mit niedrigem Lösungsmittelgehalt, eine diese Harzzusammensetzung enthaltende Überzugszusammensetzung und ein Verfahren zum Auftragen dieser Überzugszusammensetzung |
| US6040009A (en) * | 1994-06-23 | 2000-03-21 | Mazda Motor Corporation | Low solvent content type-resin composition, coating composition containing such resin composition and process for coating such coating composition |
| IL116255A (en) * | 1995-01-05 | 2004-02-19 | Du Pont | High-solids coating composition |
| US5527936A (en) | 1995-02-17 | 1996-06-18 | E. I. Du Pont De Nemours And Company | Hydrosilylation of unsaturated compounds |
| NZ303624A (en) * | 1995-03-08 | 1999-01-28 | Du Pont | Reactive organosilicons as coatings, adhesives, and sealants |
| US6268456B1 (en) * | 1995-06-05 | 2001-07-31 | E. I. Du Pont De Nemours And Company | Coating composition containing silane functionality |
| US6080816A (en) * | 1997-11-10 | 2000-06-27 | E. I. Du Pont De Nemours And Company | Coatings that contain reactive silicon oligomers |
| US6221494B1 (en) * | 1998-11-03 | 2001-04-24 | E.I. Du Pont De Nemours And Company | Reactive oligomers for isocyanate coatings |
-
1999
- 1999-02-03 IL IL13707599A patent/IL137075A0/xx unknown
- 1999-02-03 CA CA002319547A patent/CA2319547A1/en not_active Abandoned
- 1999-02-03 DE DE69929306T patent/DE69929306T2/de not_active Expired - Fee Related
- 1999-02-03 NZ NZ505793A patent/NZ505793A/xx unknown
- 1999-02-03 WO PCT/US1999/002266 patent/WO1999040140A1/en not_active Ceased
- 1999-02-03 DK DK99904555T patent/DK1054916T3/da active
- 1999-02-03 KR KR1020007008592A patent/KR100564200B1/ko not_active Expired - Fee Related
- 1999-02-03 US US09/582,834 patent/US6428898B1/en not_active Expired - Lifetime
- 1999-02-03 JP JP2000530565A patent/JP2002502902A/ja active Pending
- 1999-02-03 EP EP99904555A patent/EP1054916B1/en not_active Expired - Lifetime
- 1999-02-03 BR BR9908131-8A patent/BR9908131A/pt not_active Application Discontinuation
- 1999-02-03 ES ES99904555T patent/ES2255244T3/es not_active Expired - Lifetime
- 1999-02-03 AU AU24932/99A patent/AU756298B2/en not_active Ceased
- 1999-03-29 TW TW088101832A patent/TW483927B/zh not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997044402A1 (en) * | 1996-05-17 | 1997-11-27 | E.I. Du Pont De Nemours And Company | Mar-resistant oligomeric-based coatings |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2319547A1 (en) | 1999-08-12 |
| WO1999040140A1 (en) | 1999-08-12 |
| US6428898B1 (en) | 2002-08-06 |
| EP1054916A1 (en) | 2000-11-29 |
| NZ505793A (en) | 2002-11-26 |
| IL137075A0 (en) | 2001-06-14 |
| DE69929306T2 (de) | 2006-09-21 |
| BR9908131A (pt) | 2000-11-28 |
| AU2493299A (en) | 1999-08-23 |
| KR20010040712A (ko) | 2001-05-15 |
| ES2255244T3 (es) | 2006-06-16 |
| EP1054916B1 (en) | 2006-01-04 |
| DK1054916T3 (da) | 2006-03-06 |
| DE69929306D1 (de) | 2006-03-30 |
| TW483927B (en) | 2002-04-21 |
| KR100564200B1 (ko) | 2006-03-28 |
| JP2002502902A (ja) | 2002-01-29 |
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