CA1089140A - Revetement en polyurethanne en presence d'eau - Google Patents

Revetement en polyurethanne en presence d'eau

Info

Publication number: CA1089140A
Authority: CA; Canada
Prior art keywords: weight; groups; water; prepolymer; nco
Prior art date: 1975-06-02
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

Application number

CA253,299A

Other languages

English (en)

Inventor

Roger L. Scriven

Wen-Hsuan Chang

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

PPG Industries Inc

Original Assignee

PPG Industries Inc

Priority date (The priority date 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 date listed.)

1975-06-02

Filing date

1976-05-26

Publication date

1980-11-04

1975-06-02 Priority claimed from US05/582,946 external-priority patent/US4066591A/en

1975-06-02 Priority claimed from US05/583,085 external-priority patent/US4046729A/en

1976-05-26 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1980-02-06 Priority to CA345,185A priority Critical patent/CA1088236A/fr

1980-11-04 Application granted granted Critical

1980-11-04 Publication of CA1089140A publication Critical patent/CA1089140A/fr

Status Expired legal-status Critical Current

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
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
UWXDDXOZBBELQX-UHFFFAOYSA-N (1-amino-3-hydroxypropyl)phosphonic acid Chemical compound OP(=O)(O)C(N)CCO UWXDDXOZBBELQX-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical class CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
ZUQBWPZNPMMWQK-UHFFFAOYSA-N 1-chloro-4-isocyanatocyclohexane Chemical compound ClC1CCC(N=C=O)CC1 ZUQBWPZNPMMWQK-UHFFFAOYSA-N 0.000 description 1
WIERREHJAVDNEX-UHFFFAOYSA-N 1-chloro-n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NC(Cl)NC1=CC=CC=C1 WIERREHJAVDNEX-UHFFFAOYSA-N 0.000 description 1
XHWHHMNORMIBBB-UHFFFAOYSA-N 2,2,3,3-tetrahydroxybutanedioic acid Chemical compound OC(=O)C(O)(O)C(O)(O)C(O)=O XHWHHMNORMIBBB-UHFFFAOYSA-N 0.000 description 1
PNJJKWLRMWJONM-UHFFFAOYSA-N 2,2,3-trihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)(O)C(O)=O PNJJKWLRMWJONM-UHFFFAOYSA-N 0.000 description 1
BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 1
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
ASKYWMOISVTUON-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;phosphoric acid Chemical compound OP(O)(O)=O.CCC(CO)(CO)CO ASKYWMOISVTUON-UHFFFAOYSA-N 0.000 description 1
MBIQENSCDNJOIY-UHFFFAOYSA-N 2-hydroxy-2-methylbutyric acid Chemical compound CCC(C)(O)C(O)=O MBIQENSCDNJOIY-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
WXLPKTIAUMCNDX-UHFFFAOYSA-N 2h-pyran-3-ol Chemical compound OC1=CC=COC1 WXLPKTIAUMCNDX-UHFFFAOYSA-N 0.000 description 1
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 1
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
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 1
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
101100025412 Arabidopsis thaliana XI-A gene Proteins 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
244000020518 Carthamus tinctorius Species 0.000 description 1
235000003255 Carthamus tinctorius Nutrition 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
ZAOHKACVOFGZOI-UHFFFAOYSA-N Fominoben hydrochloride Chemical compound [Cl-].ClC=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1CN(C)CC(=O)[NH+]1CCOCC1 ZAOHKACVOFGZOI-UHFFFAOYSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
239000005058 Isophorone diisocyanate Substances 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920001730 Moisture cure polyurethane Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000004347 Perilla Nutrition 0.000 description 1
244000124853 Perilla frutescens Species 0.000 description 1
229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
235000019485 Safflower oil Nutrition 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
JTXJZBMXQMTSQN-UHFFFAOYSA-N amino hydrogen carbonate Chemical class NOC(O)=O JTXJZBMXQMTSQN-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229920006318 anionic polymer Polymers 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
RNSLCHIAOHUARI-UHFFFAOYSA-N butane-1,4-diol;hexanedioic acid Chemical compound OCCCCO.OC(=O)CCCCC(O)=O RNSLCHIAOHUARI-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
229920006317 cationic polymer Polymers 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
230000008859 change Effects 0.000 description 1
238000010382 chemical cross-linking Methods 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
HHLUHHCJLNGYFC-UHFFFAOYSA-L dibutyltin(2+);dodecanoate;ethyl carbamate Chemical compound CCOC(N)=O.CCCC[Sn+2]CCCC.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O HHLUHHCJLNGYFC-UHFFFAOYSA-L 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000006260 foam Substances 0.000 description 1
229960004594 fominoben Drugs 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
238000007429 general method Methods 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
229960002989 glutamic acid Drugs 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
238000013007 heat curing Methods 0.000 description 1
125000000623 heterocyclic group Chemical class 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
WPEOOEIAIFABQP-UHFFFAOYSA-N hexanedioic acid;hexane-1,6-diol Chemical compound OCCCCCCO.OC(=O)CCCCC(O)=O WPEOOEIAIFABQP-UHFFFAOYSA-N 0.000 description 1
HBZAMAKYLQLIOT-UHFFFAOYSA-N hydroperoxy(methyl)phosphinic acid Chemical compound CP(O)(=O)OO HBZAMAKYLQLIOT-UHFFFAOYSA-N 0.000 description 1
125000001165 hydrophobic group Chemical group 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000003999 initiator Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 1
WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920006149 polyester-amide block copolymer Polymers 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
229920002578 polythiourethane polymer Polymers 0.000 description 1
229920005749 polyurethane resin Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000003847 radiation curing Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000013049 sediment Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000006557 surface reaction Methods 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1
229920002803 thermoplastic polyurethane Polymers 0.000 description 1
239000004634 thermosetting polymer Substances 0.000 description 1
UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
150000004998 toluenediamines Chemical class 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
239000002383 tung oil Substances 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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)

CA253,299A 1975-06-02 1976-05-26 Revetement en polyurethanne en presence d'eau Expired CA1089140A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA345,185A CA1088236A (fr)	1975-06-02	1980-02-06	Produits d'appret a base d'urethanne, reduits a l'eau

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/582,946 US4066591A (en)	1975-06-02	1975-06-02	Water-reduced urethane coating compositions
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

Publications (1)

Publication Number	Publication Date
CA1089140A true CA1089140A (fr)	1980-11-04

Family

ID=27078690

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA253,299A Expired CA1089140A (fr)	1975-06-02	1976-05-26	Revetement en polyurethanne en presence d'eau

Country Status (6)

Country	Link
JP (1)	JPS51147597A (fr)
AU (1)	AU502343B2 (fr)
CA (1)	CA1089140A (fr)
DE (1)	DE2624442B2 (fr)
FR (1)	FR2355879A1 (fr)
IT (1)	IT1062319B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
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 (31)

* Cited by examiner, † Cited by third party
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
ES2077901T3 (es) *	1991-04-05	1995-12-01	Bayer Ag	Dispersiones acuosas de poliuretano-urea basadas en bis-(4-isocianatociclohexil)-metano enriquecido en el isomero trans,trans y revestimientos y peliculas preparados a partir de las mismas.
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
CA2589849A1 (fr) *	2004-12-10	2006-06-15	Mitsui Chemicals Polyurethanes, Inc.	Resine de polyurethane en phase aqueuse, procede servant a produire une resine de polyurethane en phase aqueuse et film
PL2115026T3 (pl) *	2007-01-30	2018-12-31	Dow Global Technologies Llc	Poliole inicjowane aminą i wytworzona z nich sztywna pianka poliuretanowa
ITVA20080025A1 (it) *	2008-04-24	2009-10-25	Lamberti Spa	Poliuretani cationici filmanti in dispersione acquosa
EP2690117A1 (fr)	2012-07-24	2014-01-29	ALLNEX AUSTRIA GmbH	Polyuréthanne dispersible dans de l'eau
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 (fr)	2016-04-20	2017-10-25	ALLNEX AUSTRIA GmbH	Dispersion aqueuse de polyuréthanne
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
JP7826771B2 (ja) *	2022-03-22	2026-03-10	Ｕｂｅ株式会社	水性ポリウレタン樹脂分散体組成物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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/fr not_active Expired
- 1976-06-01 FR FR7616535A patent/FR2355879A1/fr active Granted
- 1976-06-01 DE DE19762624442 patent/DE2624442B2/de not_active Ceased
- 1976-06-01 IT IT6834676A patent/IT1062319B/it active
- 1976-06-02 JP JP51065087A patent/JPS51147597A/ja active Granted

Cited By (4)

* Cited by examiner, † Cited by third party
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
FR2355879B1 (fr)	1980-12-26
AU502343B2 (en)	1979-07-19
FR2355879A1 (fr)	1978-01-20
IT1062319B (it)	1984-10-10
AU1435276A (en)	1977-12-01
JPS5422236B2 (fr)	1979-08-04
DE2624442A1 (de)	1976-12-09
JPS51147597A (en)	1976-12-17
DE2624442B2 (de)	1981-04-09

Legal Events

Date	Code	Title	Description
1997-11-04	MKEX	Expiry

Publication	Publication Date	Title
US4066591A (en)	1978-01-03	Water-reduced urethane coating compositions
US4147679A (en)	1979-04-03	Water-reduced urethane coating compositions
US4046729A (en)	1977-09-06	Water-reduced urethane coating compositions
US5354807A (en)	1994-10-11	Anionic water dispersed polyurethane polymer for improved coatings and adhesives
CA1163040A (fr)	1984-02-28	Compositions aqueuses de polyurethane
KR100191952B1 (ko)	1999-06-15	수성의 무용매성 또는 저휘발성의 2성분 폴리우레탄 피복 조성물 분산액
US6166127A (en)	2000-12-26	Interpenetrating networks of polymers
CA2335579C (fr)	2005-09-27	Reseaux d'interpenetration partielle de polymeres
US5155163A (en)	1992-10-13	Aqueous polyurethane dispersion synthesis for adhesive thermoforming applications
EP2956495B1 (fr)	2017-11-08	Dispersion uréthane-polyamide à base d'eau
DE2624442A1 (de)	1976-12-09	Wasserhaltige dispersionen
CN101437863B (zh)	2012-03-21	油基含水聚氨酯分散体
US4098743A (en)	1978-07-04	Polylactone-polyurethanes and aqueous dispersions thereof
US9988555B2 (en)	2018-06-05	Water-borne polyamide-urea dispersions
JPH08512088A (ja)	1996-12-17	シロキサン・リンケージを含むポリウレタンの水性ディスパージョン、その製造、およびコーティング組成物における使用
JP5170499B2 (ja)	2013-03-27	ブロックイソシアネート含有エマルジョン組成物及びその製造方法並びに焼付け型塗料用又は接着剤用組成物
US6635706B1 (en)	2003-10-21	Urethane-acrylic hybrid polymer dispersion
US6429254B2 (en)	2002-08-06	Aqueous polyurethane dispersions containing polybutadiene units
US20020193507A1 (en)	2002-12-19	Polyurethane dispersion with high film hardness, process for preparing it, and its use
JPH09504335A (ja)	1997-04-28	モジュラーシステムおよび水性コーティング組成物の製造法
WO2001027179A1 (fr)	2001-04-19	Procede de preparation d'une dispersion aqueuse d'un polyurethane anionique exempt d'amines tertiaires volatiles
WO2002031021A1 (fr)	2002-04-18	Dispersions de compose organique faiblement volatile d'alkyde polyol et dispersions de polyurethanne
JPH05295076A (ja)	1993-11-09	ポリウレタン水性分散液の製造方法
JPH11106733A (ja)	1999-04-20	水系ポリウレタンエマルジョン並びにこれを用いた水系接着剤及び水系塗料
CA1088236A (fr)	1980-10-21	Produits d'appret a base d'urethanne, reduits a l'eau

CA1089140A - Revetement en polyurethanne en presence d'eau - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (4)

Publications (1)

Family

ID=27078690

Family Applications (1)

Country Status (6)

Cited By (4)

Families Citing this family (31)

Family Cites Families (7)

Cited By (4)

Also Published As

Similar Documents

Legal Events