CA1089140A - Water-reduced urethane coating compositions - Google Patents
Water-reduced urethane coating compositionsInfo
- Publication number
- CA1089140A CA1089140A CA253,299A CA253299A CA1089140A CA 1089140 A CA1089140 A CA 1089140A CA 253299 A CA253299 A CA 253299A CA 1089140 A CA1089140 A CA 1089140A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- groups
- water
- prepolymer
- nco
- 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
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 229910001868 water Inorganic materials 0.000 title claims abstract description 65
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title description 6
- 239000008199 coating composition Substances 0.000 title description 4
- 229920000642 polymer Polymers 0.000 claims abstract description 100
- 239000004814 polyurethane Substances 0.000 claims abstract description 53
- 229920002635 polyurethane Polymers 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 47
- 239000000463 material Substances 0.000 claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 35
- 239000006185 dispersion Substances 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
- 150000003839 salts Chemical group 0.000 claims description 47
- 229920005862 polyol Polymers 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 34
- 150000003077 polyols Chemical class 0.000 claims description 34
- 239000005056 polyisocyanate Substances 0.000 claims description 28
- 229920001228 polyisocyanate Polymers 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 19
- 150000002500 ions Chemical class 0.000 claims description 18
- 239000012736 aqueous medium Substances 0.000 claims description 14
- 125000000129 anionic group Chemical group 0.000 claims description 12
- 239000003995 emulsifying agent Substances 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 229920005906 polyester polyol Polymers 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 5
- 229920003180 amino resin Polymers 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229920000768 polyamine Polymers 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 3
- 239000006184 cosolvent Substances 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims 1
- 125000000271 carboxylic acid salt group Chemical group 0.000 claims 1
- 125000005314 unsaturated fatty acid group Chemical group 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 55
- 238000006243 chemical reaction Methods 0.000 abstract description 53
- 239000011248 coating agent Substances 0.000 abstract description 31
- 150000004985 diamines Chemical class 0.000 abstract description 10
- 238000001035 drying Methods 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000001228 spectrum Methods 0.000 abstract description 2
- -1 poly(urethane-urea) Polymers 0.000 description 83
- 239000000047 product Substances 0.000 description 62
- 229920005989 resin Polymers 0.000 description 60
- 239000011347 resin Substances 0.000 description 60
- 239000002253 acid Substances 0.000 description 57
- 239000004970 Chain extender Substances 0.000 description 48
- 238000001723 curing Methods 0.000 description 32
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 30
- 239000008367 deionised water Substances 0.000 description 29
- 229910021641 deionized water Inorganic materials 0.000 description 29
- 239000002904 solvent Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 150000001412 amines Chemical class 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
- 239000000376 reactant Substances 0.000 description 19
- 150000002009 diols Chemical class 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 14
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 14
- 238000006386 neutralization reaction Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 125000002091 cationic group Chemical group 0.000 description 13
- 239000012948 isocyanate Substances 0.000 description 13
- 150000002513 isocyanates Chemical class 0.000 description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 229920001610 polycaprolactone Polymers 0.000 description 12
- 229920003009 polyurethane dispersion Polymers 0.000 description 12
- 238000005755 formation reaction Methods 0.000 description 11
- 239000004922 lacquer Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000499 gel Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 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 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000003010 ionic group Chemical group 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 230000003381 solubilizing effect Effects 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 229940012017 ethylenediamine Drugs 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000010008 shearing Methods 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229960002887 deanol Drugs 0.000 description 4
- 239000012972 dimethylethanolamine Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- 150000004072 triols Chemical class 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
- 229920003270 Cymel® Polymers 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- 150000002483 hydrogen compounds Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229960005337 lysine hydrochloride Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 230000009974 thixotropic effect Effects 0.000 description 3
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 2
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 description 2
- VYONOYYDEFODAJ-UHFFFAOYSA-N 2-(1-Aziridinyl)ethanol Chemical compound OCCN1CC1 VYONOYYDEFODAJ-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
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000007590 electrostatic spraying Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 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 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
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- 229920002554 vinyl polymer Polymers 0.000 description 2
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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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
-
- 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
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA345,185A CA1088236A (en) | 1975-06-02 | 1980-02-06 | Water-reduced urethane coating compositions |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/583,085 US4046729A (en) | 1975-06-02 | 1975-06-02 | Water-reduced urethane coating compositions |
| US583,085 | 1975-06-02 | ||
| US582,946 | 1975-06-02 | ||
| US05/582,946 US4066591A (en) | 1975-06-02 | 1975-06-02 | Water-reduced urethane coating compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1089140A true CA1089140A (en) | 1980-11-04 |
Family
ID=27078690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA253,299A Expired CA1089140A (en) | 1975-06-02 | 1976-05-26 | Water-reduced urethane coating compositions |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS51147597A (enrdf_load_stackoverflow) |
| AU (1) | AU502343B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1089140A (enrdf_load_stackoverflow) |
| DE (1) | DE2624442B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2355879A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1062319B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6555612B1 (en) | 1999-01-28 | 2003-04-29 | Basf Coatings Ag | Aqueous coating material and modular system for producing same |
| US6555613B1 (en) | 1999-03-10 | 2003-04-29 | Basf Coatings Ag | Polyurethane and its use for producing solvent-free coating substances |
| US6630537B1 (en) | 1997-07-22 | 2003-10-07 | Basf Coatings Ag | Coating agent and method for producing same |
| US10538613B2 (en) | 2009-10-27 | 2020-01-21 | Allnex Austria Gmbh | Aqueously dispersible polyurethane |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554308A (en) * | 1978-10-02 | 1985-11-19 | Wilmington Chemical Corporation | Crosslinked polyurethane dispersions |
| DE2843790A1 (de) * | 1978-10-06 | 1980-04-17 | Bayer Ag | Verfahren zur herstellung von waessrigen dispersionen oder loesungen von polyurethan-polyharnstoffen, die nach diesem verfahren erhaeltlichen dispersionen oder loesungen, sowie ihre verwendung |
| DE2920334A1 (de) * | 1979-05-19 | 1980-12-04 | Basf Ag | Magnetische aufzeichnungstraeger |
| US4387181A (en) * | 1980-04-09 | 1983-06-07 | Textron, Inc. | Polymer compositions and manufacture |
| JPS5785815A (en) * | 1980-11-14 | 1982-05-28 | Dainippon Ink & Chem Inc | Water-dispersible resin for paint |
| DE3344693A1 (de) * | 1983-12-10 | 1985-06-20 | Bayer Ag, 5090 Leverkusen | Waessrige loesungen oder dispersionen von polyisocyanat-polyadditionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als bzw. zur herstellung von klebemittel |
| IT1177161B (it) * | 1984-11-12 | 1987-08-26 | Resem Spa | Polimeri di monomeri etilenicamente insaturi modificati con oligouretani e dispersioni acquose da essi ottenute |
| JPS61278570A (ja) * | 1985-06-03 | 1986-12-09 | Dai Ichi Kogyo Seiyaku Co Ltd | 塗装組成物 |
| DE3545195A1 (de) * | 1985-12-20 | 1987-06-25 | Hoechst Ag | Isocyanatfreie polyurethan-dispersionen |
| DE3625605A1 (de) * | 1986-07-29 | 1988-02-11 | Hoechst Ag | Waessrige pigmentzubereitungen und ihre verwendung |
| DE3636974A1 (de) * | 1986-10-30 | 1988-05-05 | Bayer Ag | Poly-(ether-urethan-harnstoff)polyadditionsprodukte, ihre herstellung, abmischung enthaltend diese sowie ihre verwendung als abformmassen |
| DE3722005A1 (de) | 1987-07-03 | 1989-01-12 | Herberts Gmbh | Verfahren zur herstellung eines mehrschichtueberzuges und hierfuer geeignetes waessriges ueberzugsmittel |
| JPH02269723A (ja) * | 1989-04-12 | 1990-11-05 | Dai Ichi Kogyo Seiyaku Co Ltd | 水系ウレタン樹脂組成物 |
| DE4019171A1 (de) * | 1990-06-15 | 1991-12-19 | Henkel Kgaa | Beschichtungsmittel |
| DE4143688B4 (de) | 1991-03-30 | 2007-03-29 | Basf Coatings Ag | Verwendung eines Mischsystems sowie Verfahren zur Herstellung von Wasserbasislacken und von wasserverdünnbaren Überzugsmitteln |
| DE69205471T2 (de) * | 1991-04-05 | 1996-03-21 | Bayer Ag | Auf Bis-(4-isocyanatocyclohexyl)-Methan, das mit Trans, Trans-Isomer angereichert ist, basierende wässrige Polyurethanharnstoffdispersionen und die daraus hergestellte Beschichtungen oder Filme. |
| JP2700290B2 (ja) * | 1993-05-17 | 1998-01-19 | 三洋化成工業株式会社 | 塗料組成物 |
| JP3511306B2 (ja) * | 1994-02-17 | 2004-03-29 | 旭化成ケミカルズ株式会社 | 水系被覆組成物 |
| DE10152294A1 (de) | 2001-10-26 | 2003-05-08 | Solutia Austria Gmbh Werndorf | Hochmolekulare Polyurethan-Dispersionen |
| AT500555B1 (de) | 2003-06-13 | 2009-11-15 | Cytec Surface Specialties At | Selbstvernetzende wässrige polyurethandispersionen |
| AT412648B (de) | 2003-06-27 | 2005-05-25 | Surface Specialties Austria | Wasserverdünnbare polyurethandispersionen |
| US7691940B2 (en) * | 2004-12-10 | 2010-04-06 | Mitsui Chemicals, Inc. | Aqueous polyurethane resin and method for producing aqueous polyurethane resin and film |
| EP2115026B1 (en) * | 2007-01-30 | 2018-05-02 | Dow Global Technologies LLC | Amine-initiated polyols and rigid polyurethane foam made therefrom |
| ITVA20080025A1 (it) * | 2008-04-24 | 2009-10-25 | Lamberti Spa | Poliuretani cationici filmanti in dispersione acquosa |
| EP2690117A1 (en) | 2012-07-24 | 2014-01-29 | ALLNEX AUSTRIA GmbH | Aqueously Dispersible Polyurethane |
| US9499718B2 (en) * | 2013-03-21 | 2016-11-22 | Axalta Coating Systems Ip Co., Llc | Process for the production of an OEM base coat/clear top coat multi-layer coating |
| JP6124645B2 (ja) * | 2013-03-27 | 2017-05-10 | 第一工業製薬株式会社 | リチウム二次電池の電極用結着剤、該結着剤を用いて製造された電極を使用したリチウム二次電池 |
| EP3235844A1 (en) | 2016-04-20 | 2017-10-25 | ALLNEX AUSTRIA GmbH | Aqueous polyurethane dispersion |
| JP7393173B2 (ja) * | 2019-09-30 | 2023-12-06 | 第一工業製薬株式会社 | フィルムコーティング剤 |
| GB202102946D0 (en) * | 2021-03-02 | 2021-04-14 | Croda Int Plc | Quaternised polyol and polymer substrates containing the same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495745C3 (de) * | 1963-09-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung wäßriger, emulgatorfreier Polyurethan-Latices |
| DE1939911U (de) | 1966-04-07 | 1966-06-02 | Duerkoppwerke Ag | Kegelrollenlager. |
| DE1282962B (de) * | 1966-04-28 | 1968-11-14 | Bayer Ag | Verfahren zur Herstellung waessriger sedimentierender redispergierbaren Dispersionen vernetzter, Harnstoffgruppe aufweisender Polyadditionsprodukte |
| CA931688A (en) * | 1968-08-02 | 1973-08-07 | C. Carlson Robert | Sulfonated aromatic polyisocyanates and preparation of stable anionic polyurethane or polyurea latices therefrom |
| US3988278A (en) * | 1970-08-17 | 1976-10-26 | Minnesota Mining And Manufacturing Company | Stable polymer latex and process for making same |
| DE2314513C3 (de) * | 1973-03-23 | 1980-08-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von wäßrigen Polyurethandispersionen |
| DE2344135C2 (de) * | 1973-09-01 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen Herstellung von wäßrigen Polyurethandispersionen |
-
1976
- 1976-03-27 AU AU14352/76A patent/AU502343B2/en not_active Expired
- 1976-05-26 CA CA253,299A patent/CA1089140A/en not_active Expired
- 1976-06-01 IT IT6834676A patent/IT1062319B/it active
- 1976-06-01 DE DE19762624442 patent/DE2624442B2/de not_active Ceased
- 1976-06-01 FR FR7616535A patent/FR2355879A1/fr active Granted
- 1976-06-02 JP JP51065087A patent/JPS51147597A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6630537B1 (en) | 1997-07-22 | 2003-10-07 | Basf Coatings Ag | Coating agent and method for producing same |
| US6555612B1 (en) | 1999-01-28 | 2003-04-29 | Basf Coatings Ag | Aqueous coating material and modular system for producing same |
| US6555613B1 (en) | 1999-03-10 | 2003-04-29 | Basf Coatings Ag | Polyurethane and its use for producing solvent-free coating substances |
| US10538613B2 (en) | 2009-10-27 | 2020-01-21 | Allnex Austria Gmbh | Aqueously dispersible polyurethane |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2624442B2 (de) | 1981-04-09 |
| AU502343B2 (en) | 1979-07-19 |
| FR2355879A1 (fr) | 1978-01-20 |
| FR2355879B1 (enrdf_load_stackoverflow) | 1980-12-26 |
| DE2624442A1 (de) | 1976-12-09 |
| JPS51147597A (en) | 1976-12-17 |
| AU1435276A (en) | 1977-12-01 |
| JPS5422236B2 (enrdf_load_stackoverflow) | 1979-08-04 |
| IT1062319B (it) | 1984-10-10 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |