DE60208538T2 - Bei raumtemperatur härtende, schnelltrocknende, lösungsmittelhaltige beschichtungszusammensetzungen - Google Patents
Bei raumtemperatur härtende, schnelltrocknende, lösungsmittelhaltige beschichtungszusammensetzungen Download PDFInfo
- Publication number
- DE60208538T2 DE60208538T2 DE60208538T DE60208538T DE60208538T2 DE 60208538 T2 DE60208538 T2 DE 60208538T2 DE 60208538 T DE60208538 T DE 60208538T DE 60208538 T DE60208538 T DE 60208538T DE 60208538 T2 DE60208538 T2 DE 60208538T2
- Authority
- DE
- Germany
- Prior art keywords
- coating composition
- composition according
- acetoacetate
- polyamine
- glycol
- 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
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- 239000008199 coating composition Substances 0.000 title claims description 47
- 238000001035 drying Methods 0.000 title description 13
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 57
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
- -1 Triethylolpropane Chemical compound 0.000 claims description 48
- 229920000768 polyamine Polymers 0.000 claims description 48
- 229920005862 polyol Polymers 0.000 claims description 38
- 150000003077 polyols Chemical class 0.000 claims description 38
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 32
- 239000004606 Fillers/Extenders Substances 0.000 claims description 30
- 229920000647 polyepoxide Polymers 0.000 claims description 28
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 23
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 23
- 239000011230 binding agent Substances 0.000 claims description 21
- 239000003822 epoxy resin Substances 0.000 claims description 21
- 229920000728 polyester Polymers 0.000 claims description 21
- 238000000576 coating method Methods 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229920000058 polyacrylate Polymers 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 15
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 15
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 14
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 14
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 13
- 238000004132 cross linking Methods 0.000 claims description 13
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 13
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 235000011187 glycerol Nutrition 0.000 claims description 10
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 10
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims description 8
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 8
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 claims description 7
- LBZZJNPUANNABV-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)phenyl]ethanol Chemical compound OCCC1=CC=C(CCO)C=C1 LBZZJNPUANNABV-UHFFFAOYSA-N 0.000 claims description 7
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 claims description 7
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 claims description 7
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 5
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 5
- 150000002466 imines Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000001282 organosilanes Chemical class 0.000 claims description 2
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 22
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 17
- 239000000178 monomer Substances 0.000 description 16
- 239000003973 paint Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229940117969 neopentyl glycol Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-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 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 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 3
- 150000004658 ketimines Chemical class 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 2
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- BPRJQFIHEGORJE-UHFFFAOYSA-N 2-(1-hydroxypropan-2-yloxy)propan-1-ol 1-(2-hydroxypropoxy)propan-2-ol Chemical compound CC(O)COCC(C)O.CC(CO)OC(C)CO BPRJQFIHEGORJE-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- QSMHTOCQXUAUFB-UHFFFAOYSA-N 3-tert-butyl-4-[2-(2-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(C)(C)C1=CC(O)=CC=C1C(C)(C)C1=CC=C(O)C=C1C(C)(C)C QSMHTOCQXUAUFB-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4042—Imines; Imides
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (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)
- Epoxy Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26680701P | 2001-02-06 | 2001-02-06 | |
| US266807P | 2001-02-06 | ||
| PCT/US2002/003597 WO2002062909A1 (en) | 2001-02-06 | 2002-02-06 | Ambient cure fast dry solvent borne coating compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60208538D1 DE60208538D1 (de) | 2006-03-30 |
| DE60208538T2 true DE60208538T2 (de) | 2006-11-09 |
Family
ID=23016074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60208538T Expired - Fee Related DE60208538T2 (de) | 2001-02-06 | 2002-02-06 | Bei raumtemperatur härtende, schnelltrocknende, lösungsmittelhaltige beschichtungszusammensetzungen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6740359B2 (https=) |
| EP (1) | EP1358286B1 (https=) |
| JP (1) | JP2004532288A (https=) |
| CA (1) | CA2433001A1 (https=) |
| DE (1) | DE60208538T2 (https=) |
| WO (1) | WO2002062909A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003064152A (ja) * | 2001-08-23 | 2003-03-05 | Japan Epoxy Resin Kk | 変性エポキシ樹脂組成物とその製造法及びその組成物を用いた無溶剤型塗料 |
| EP1572446A2 (en) * | 2002-12-18 | 2005-09-14 | JohnsonDiversey, Inc. | Ultra-thin surface modification system |
| US20050010022A1 (en) * | 2003-07-09 | 2005-01-13 | Yasuo Chiba | Epoxy resin compositions |
| JP4765323B2 (ja) * | 2004-02-23 | 2011-09-07 | 三菱化学株式会社 | 変性エポキシ樹脂組成物及びその製造方法 |
| US9095878B2 (en) | 2006-08-02 | 2015-08-04 | Ford Motor Company | Coating compositions and methods of applying the same |
| DE102006039941A1 (de) * | 2006-08-25 | 2008-02-28 | Wacker Chemie Ag | Verfahren zur Behandlung von cellulosehaltigen Fasern oder Flächengebilde enthaltend cellulosehaltige Fasern |
| WO2010011714A2 (en) * | 2008-07-23 | 2010-01-28 | 3M Innovative Properties Company | Reactive liquid modifiers |
| EP2321370B1 (en) | 2008-07-23 | 2017-03-15 | 3M Innovative Properties Company | Two-part epoxy-based structural adhesives |
| CN102159615B (zh) | 2008-07-23 | 2014-10-01 | 3M创新有限公司 | 两部分的环氧基结构粘合剂 |
| CN102395632B (zh) * | 2009-02-17 | 2014-12-10 | 威士伯采购公司 | 包含乙酰酰基官能聚合物的溶剂型涂料组合物 |
| CN103068946B (zh) | 2010-08-10 | 2015-05-06 | 3M创新有限公司 | 环氧树脂结构粘合剂 |
| US20130034741A1 (en) * | 2011-08-04 | 2013-02-07 | Ppg Industries Ohio, Inc. | Branched polyester polymers comprising isophthalic acid and coatings comprising the same |
| CN103820006B (zh) * | 2014-02-28 | 2017-01-11 | 北京东方雨虹防水技术股份有限公司 | 一种tpo表面处理用涂料及其制备方法 |
| CN104710911B (zh) * | 2015-03-08 | 2017-05-03 | 宁波高新区夏远科技有限公司 | 一种毛巾架用防滑涂料及其制备方法 |
| TWI713498B (zh) | 2015-03-24 | 2020-12-21 | 美商羅門哈斯公司 | 核-殼水性乳膠 |
| CN106590320A (zh) * | 2015-10-16 | 2017-04-26 | 中兴通讯股份有限公司 | 一种铝合金压铸件缺陷修补剂及其制备方法 |
| US11732165B2 (en) | 2017-06-13 | 2023-08-22 | Eastman Chemical Company | Low-temperature curable compositions |
| KR102787540B1 (ko) | 2018-05-07 | 2025-03-31 | 에스더블유아이엠씨 엘엘씨 | 내부식성 프라이머 및 탑코트 조성물 |
| CN112912451B (zh) | 2018-09-26 | 2023-09-15 | Swimc有限公司 | 可固化涂料组合物 |
| CN113166033B (zh) | 2018-12-11 | 2024-05-24 | 伊士曼化工公司 | 可固化涂料组合物 |
| EP3894509B1 (en) | 2018-12-11 | 2024-03-20 | Eastman Chemical Company | Self-curable and low temperature curable coating compositions |
| WO2020123284A1 (en) | 2018-12-11 | 2020-06-18 | Eastman Chemical Company | Flexible substrates comprising curable compositions containing acetoacetylated resins |
| EP4031598A4 (en) | 2019-09-18 | 2023-10-25 | Swimc LLC | COATING COMPOSITIONS AND METHODS INVOLVING A POLYFUNCTIONAL CARBAMATE SALT |
| US11525059B2 (en) | 2019-10-15 | 2022-12-13 | Swimc, Llc | Intumescent coating compositions effective at low temperatures |
| CN114891317B (zh) * | 2022-05-16 | 2023-12-26 | 上纬新材料科技股份有限公司 | 一种可降解拉挤板材复合材料及其在风电叶片上的应用 |
| EP4464751B1 (de) * | 2023-05-16 | 2025-07-23 | STO SE & Co. KGaA | Reaktive 2k-beschichtungszusammensetzung |
| EP4563617A1 (de) | 2023-11-29 | 2025-06-04 | Sika Technology AG | Härtbare zusammensetzungen enthaltend funktionelle polyester und aldimine |
| US20250270407A1 (en) * | 2024-02-23 | 2025-08-28 | Swimc Llc | Multi-component direct to metal and plastic primer system |
| WO2026050463A1 (en) * | 2024-08-28 | 2026-03-05 | Ppg Industries Ohio, Inc. | Methods of curing (meth)acrylate-containing compositions |
| CN119798922A (zh) * | 2025-01-10 | 2025-04-11 | 上纬新材料科技股份有限公司 | 一种可降解环氧树脂组合物，缠绕树脂，应用及制备方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2621423A1 (de) | 1976-05-14 | 1977-12-01 | Huels Chemische Werke Ag | Form- und ueberzugsmassen |
| ATE40142T1 (de) | 1985-03-29 | 1989-02-15 | Akzo Nv | Fluessige ueberzugsmasse und verfahren zum ueberziehen von substraten mittels dieser ueberzugsmasse. |
| US4906684A (en) * | 1988-12-09 | 1990-03-06 | Rtz Chemicals, Ltd. | Ambient temperature curing polymer compositions containing acetoacetoxyethyl methacrylate, glycidyl methacrylate and a polymerizable acid |
| US5021537A (en) | 1990-04-27 | 1991-06-04 | Shell Oil Company | Polyacetoacetate-containing epoxy resin compositions |
| DE4032751A1 (de) | 1990-10-16 | 1992-04-23 | Hoechst Ag | Fluessiges beschichtungsmittel |
| US5288804A (en) * | 1992-01-03 | 1994-02-22 | Reichhold Chemicals, Inc. | Acetoacetate aromatic aldimine resin composition |
| DE4210333A1 (de) | 1992-03-30 | 1993-10-07 | Hoechst Ag | Flüssiges Beschichtungsmittel |
| US5288802A (en) | 1993-01-25 | 1994-02-22 | Ppg Industries, Inc. | Automotive refinish primer surfacer containing acetoacetate functional polyesterpolyol, a polyacrylate, and an amine functional epoxy resin |
| US5567761A (en) * | 1993-05-10 | 1996-10-22 | Guertin Bros. Coatings And Sealants Ltd. | Aqueous two-part isocyanate-free curable, polyurethane resin systems |
| US5451653A (en) * | 1994-12-28 | 1995-09-19 | Air Products And Chemicals, Inc. | Curable crosslinking system with monobenzaldimine as crosslinker |
| IL116255A (en) | 1995-01-05 | 2004-02-19 | Du Pont | High-solids coating composition |
| EP0828798B1 (en) * | 1995-05-26 | 2001-08-22 | AD Aerospace Finishes v.o.f. | Coating composition having improved adhesion to substrate |
| DE69941188D1 (de) | 1998-05-19 | 2009-09-10 | Du Pont | Verwendung einer Vernetzerkomponente enthaltend ein Polyamin und/oder ein Polyketimin |
| EP0969056A1 (en) | 1998-05-26 | 2000-01-05 | Aventis Research & Technologies GmbH & Co KG | Method for preparing an improved protein coating and articles thereof |
| EP0969029B1 (en) | 1998-06-05 | 2003-11-26 | Basf Corporation | Novel polycarbodiimide polymers and their use as adhesive intermediate layers in automotive coatings |
| US6365673B1 (en) | 1998-06-22 | 2002-04-02 | E. I. Du Pont De Nemours And Company | Low viscosity imine reactive diluents and coating compositions made therefrom |
| DE59903270D1 (de) | 1998-08-21 | 2002-12-05 | Ciba Sc Holding Ag | Photoaktivierbare stickstoffhaltige basen |
| AU1476200A (en) * | 1998-11-20 | 2000-06-13 | Sherwin-Williams Company, The | Curable compositions comprising acetoacetoxy and imine functionality |
| EP1036492A1 (en) | 1999-03-13 | 2000-09-20 | Aventis Research & Technologies GmbH & Co. KG | Seed treatment composition |
| ATE250112T1 (de) | 1999-05-05 | 2003-10-15 | Du Pont | Beschichtungszusammensetzungen enthaltend hochstrukturierte makromoleküle |
-
2002
- 2002-01-25 US US10/057,118 patent/US6740359B2/en not_active Expired - Fee Related
- 2002-02-06 WO PCT/US2002/003597 patent/WO2002062909A1/en not_active Ceased
- 2002-02-06 CA CA002433001A patent/CA2433001A1/en not_active Abandoned
- 2002-02-06 DE DE60208538T patent/DE60208538T2/de not_active Expired - Fee Related
- 2002-02-06 EP EP02724917A patent/EP1358286B1/en not_active Expired - Lifetime
- 2002-02-06 JP JP2002563253A patent/JP2004532288A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA2433001A1 (en) | 2002-08-15 |
| EP1358286A1 (en) | 2003-11-05 |
| US20020161162A1 (en) | 2002-10-31 |
| US6740359B2 (en) | 2004-05-25 |
| EP1358286B1 (en) | 2006-01-04 |
| JP2004532288A (ja) | 2004-10-21 |
| DE60208538D1 (de) | 2006-03-30 |
| WO2002062909A1 (en) | 2002-08-15 |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |