EP3887423A1 - Polyisocyanatzusammensetzung für beschichtungen - Google Patents
Polyisocyanatzusammensetzung für beschichtungenInfo
- Publication number
- EP3887423A1 EP3887423A1 EP19805971.9A EP19805971A EP3887423A1 EP 3887423 A1 EP3887423 A1 EP 3887423A1 EP 19805971 A EP19805971 A EP 19805971A EP 3887423 A1 EP3887423 A1 EP 3887423A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyisocyanate
- weight
- diisocyanate
- polyisocyanate composition
- mixture
- 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.)
- Pending
Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 124
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 124
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 238000000576 coating method Methods 0.000 title claims description 32
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 63
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- ZDKYYMRLZONTFK-UHFFFAOYSA-N 3,4-bis(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2(CN=C=O)C(CN=C=O)CC1C2 ZDKYYMRLZONTFK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 claims description 4
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 4
- DUDXQIXWPJMPRQ-UHFFFAOYSA-N isocyanatomethylcyclohexane Chemical compound O=C=NCC1CCCCC1 DUDXQIXWPJMPRQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229920005862 polyol Polymers 0.000 description 13
- 150000003077 polyols Chemical class 0.000 description 13
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 12
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000007613 environmental effect Effects 0.000 description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 description 6
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 108010019160 Pancreatin Proteins 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 229940055695 pancreatin Drugs 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000006748 scratching Methods 0.000 description 3
- 230000002393 scratching effect Effects 0.000 description 3
- 238000005829 trimerization reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- -1 isocyanatomethyl Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- LLNKPQCCIIWJGJ-UHFFFAOYSA-N N(=C=O)CC1(OCCC1)CN=C=O Chemical compound N(=C=O)CC1(OCCC1)CN=C=O LLNKPQCCIIWJGJ-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000805 Polyaspartic acid Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- KVXNKFYSHAUJIA-UHFFFAOYSA-N acetic acid;ethoxyethane Chemical compound CC(O)=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000006120 scratch resistant coating Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000012855 volatile organic compound 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
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
-
- 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
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/02—Polyureas
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
Definitions
- the invention relates to a polyisocyanate composition based on pentamethylene diisocyanate.
- the invention further relates to a method for producing the polyisocyanate composition according to the invention and the use of the polyisocyanate composition according to the invention as a crosslinking agent in a coating composition.
- the invention also relates to the use of pentamethylene diisocyanate to increase the chemical resistance of the coating obtained.
- the invention also relates to a two-component system comprising the polyisocyanate composition according to the invention, coatings produced from the two-component system and the substrates coated therewith. In coatings, particularly in the automotive industry, both scratch resistance and chemical resistance of the coatings are important properties.
- the Amtec Kistler laboratory car wash and the gradient oven method have established themselves as recognized methods in Europe for testing scratch resistance.
- Amtec Kistler GmbH uses a laboratory car wash. This laboratory washing system is based on an original washing system in terms of its proportions (amount of water, speed of rotation of the brushes, brush material, relative movements).
- Polyurethane coatings have been known for a long time.
- coatings made of aliphatic polyisocyanates and polyols such as polyacrylate polyols, polyester polyols or polycarbonate polyols are used.
- high-quality coatings particularly low-monomer derivatives made from hexamethylene diisocyanate (HDI) are used as polyisocyanates.
- HDI hexamethylene diisocyanate
- Particularly suitable for elastic, highly resistant coatings are HDI isocyanurate polyisocyanates or HDI polyisocyanates containing iminooxadiazinedione and isocyanurate structures, as described, for example, in US Pat. B. H. J. Laas, R.
- polyisocyanates generally have isocyanate functionalities (FNCO) of 3 or more, isocyanate functionality being understood to mean the average number of NCO groups per molecule.
- FNCO isocyanate functionalities
- 1,5-pentamethylene diisocyanate has also long been known as a monomer, for example from W. Siefken, Liebigs Ann. Chem. 1949, 562, page 122 or in DE 1493360 B1 and DE 1900514 Al.
- EP 0 693 512 A1 describes the use of special mixtures of HDI-based polyisocyanates which, owing to a proportion of uretdione structures and cycloaliphatic isocyanurate polyisocyanates, have improved elasticity and tear strength compared to lacquers crosslinked solely by HDI polyisocyanate. However, it is not disclosed what the chemical resistance of these lacquers to environmental influences is.
- DE 197 52 691 discloses the use of a polyisocyanate mixture based on 2-methyl-1,5-pentane diisocyanate in combination with isophorone diisocyanate (IPDI).
- IPDI isophorone diisocyanate
- 2-methyl-l, 5-pentane diisocyanate is not available in a commercially relevant amount and is therefore not a practical substitute for HDI polyisocyanates.
- WO 96/40828 A1 discloses non-aqueous dispersions, particularly suitable for use as “enamel” automotive coatings, with the task of reducing the proportion of volatile organic compounds.
- Polyisocyanates are described as crosslinking agents for alkyd resins, only pure IPDI isocyanurate being used in the examples and no comparisons with other isocyanates possible.
- a disadvantage of pure IPDI isocyanurates, however, is that they have too little flexibility in coatings.
- the object of the present invention was therefore to provide a polyisocyanate composition from which flexible coatings can be obtained which, compared to the systems known in the prior art based on HDI or 2-methyl-1,5-pentane diisocyanate, have a higher chemical resistance with constant scratch resistance towards sodium hydroxide solution and / or pancreatin.
- a polyisocyanate composition comprising a mixture of> 60% by weight, based on the total weight of the mixture, of at least one polyisocyanate based on pentamethylene diisocyanate and ⁇ 40% by weight, based on the total weight of the mixture, at least one polyisocyanate based on a cycloaliphatic diisocyanate and / or at least one polyisocyanate based on pentamethylene diisocyanate and at least one cycloaliphatic diisocyanate, the polyisocyanate composition having a residual monomer content of monomeric diisocyanates below 0.5% by weight, based on the total weight of the polyisocyanate composition.
- pentamethylene diisocyanate in the polyisocyanate composition advantageously made it possible to reduce the proportion of cycloaliphatic diisocyanates without the scratch resistance deteriorating. In this way, improved chemical resistance can be achieved and the flexibility is retained.
- references to “comprising”, “containing” etc. preferably mean “essentially consisting of” and very particularly preferably “consisting of”.
- the further embodiments mentioned in the patent claims and in the description can be combined in any way, unless the context clearly indicates the opposite.
- the mixture contains> 70% by weight, preferably> 75% by weight and particularly preferably> 80% by weight, based on the total weight of the mixture, of the at least one polyisocyanate based on pentamethylene diisocyanate and 100% by weight of missing portions each consist of the at least one polyisocyanate based on a cycloaliphatic diisocyanate and / or the at least one polyisocyanate based on pentamethylene diisocyanate and at least one cycloaliphatic diisocyanate, preferably consist of the at least one polyisocyanate based on a cycloaliphatic diisocyanate or the at least one polyisocyanate based on pentamethylene diisocyanate and at least one cycloaliphatic diisocyanate and particularly preferably consist of the at least one polyisocyanate based on a cycloaliphatic diisocyanate.
- this has the advantage that the chemical resistance is further improved without
- the polyisocyanates based on pentamethylene diisocyanate are any oligomeric polyisocyanates obtainable by modifying pentamethylene diisocyanate (PDI) with uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structure or any mixture of such polyisocyanates.
- PDI pentamethylene diisocyanate
- the content of isocyanurate trimer can be adjusted by carrying out the reaction accordingly, so the trimerization reaction is preferably terminated after the desired content of isocyanurate trimer has been reached. This can be done, for example, by cooling the reaction mixture to room temperature. In general, however, the reaction is carried out by adding one or more catalyst poisons known to the person skilled in the art and, if appropriate, the following brief heating of the reaction mixture ended, for example, to a temperature above 80 ° C.
- polyisocyanate based on pentamethylene diisocyanate means that pentamethylene diisocyanate> 50% by weight, preferably> 70% by weight, particularly preferably> 90% by weight and very particularly preferably 100% by weight of the total for the Make up monomeric diisocyanates used polyisocyanate. This has the further advantage that the chemical resistance of the coatings obtained is further improved.
- the proportion which is 100% by weight can be composed of any aliphatic, araliphatic and / or aromatic diisocyanates other than pentamethylene diisocyanate, monomeric diisocyanates suitable for this purpose being in particular those of the molecular weight range 140 to 400, such as 1,4-diisocyanatobutane, 1,1 6-hexamethylene diisocyanate, 2-methyl
- the PDI used to produce the polyisocyanates based on pentamethylene diisocyanate can be prepared in various ways, for example by phosgenation in the liquid or gas phase or by a phosgene-free route, such as, for. B. by thermal urethane cleavage, starting from preferably obtained biotechnologically by decarboxylation of the naturally occurring amino acid lysine pentamethylene diamine (PDA).
- PDA amino acid lysine pentamethylene diamine
- the production of PDI from PDA by phosgenation in the gas phase is particularly preferred.
- the above-mentioned further diisocyanates can be prepared by various known methods, for example by phosgenation in the liquid or gas phase or by a phosgene-free route, such as, for. B. by thermal urethane cleavage can be obtained.
- the polyisocyanates based on a cycloaliphatic polyisocyanate are any oligomeric polyisocyanates obtainable by modifying suitable monomeric cycloaliphatic diisocyanates with uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structure or any mixtures of such polyisocyanates.
- These polyisocyanates are prepared by methods known per se for isocyanate oligomerization, as described, for example, in J. Prakt. Chem.
- 336 (1994) 185-200 are described by way of example by reacting part of the isocyanate groups of the monomeric diisocyanates to form polyisocyanate molecules which consist of at least two diisocyanate molecules and one itself usually subsequent distillative or extractive separation of the unreacted monomeric diisocyanates.
- Polyisocyanates can be prepared from various monomeric diisocyanates by known methods, as is known, for example, from EP 47452 A1.
- the mixture contains the
- Polyisocyanate composition > 1% by weight, preferably> 2% by weight, particularly preferably> 5% by weight, very particularly preferably> 10% by weight and most preferably> 20% by weight, based on the total weight of the Mixture of the at least one polyisocyanate based on a cycloaliphatic diisocyanate and / or the at least one polyisocyanate based on pentamethylene diisocyanate and at least one cycloaliphatic diisocyanate, preferably the at least one polyisocyanate based on a cycloaliphatic diisocyanate.
- Polyisocyanate composition > 1% by weight, preferably> 2% by weight, particularly preferably> 5% by weight, very particularly preferably> 10% by weight and most preferably> 20% by weight, based on the total weight of the Mixture of the at least one polyisocyanate based on a cycloaliphatic diisocyanate or the at least one polyisocyanate based on pentamethylene diisocyanate and at least one cycloaliphatic diisocyanate, preferably the at least one polyisocyanate based on a cycloaliphatic diisocyanate.
- “based on pentamethylene diisocyanate and at least one cycloaliphatic diisocyanate” means that the at least one cycloaliphatic diisocyanate is> 50% by weight, preferably> 60% by weight, particularly preferably> 70% by weight of the total monomeric diisocyanates used. This has the further advantage that the resistance to mechanical stress is further improved.
- the proportion which is 100% by weight can consist of any cycloaliphatic diisocyanates listed above other than pentamethylene diisocyanate.
- based on a cycloaliphatic diisocyanate means that> 50% by weight, preferably> 70% by weight, particularly preferably> 90% by weight and very particularly preferably 100% by weight of the cycloaliphatic monomers used overall Diisocyanates consist of a certain cycloaliphatic monomeric diisocyanate.
- the proportion which is 100% by weight can be composed of any cycloaliphatic diisocyanates other than this cycloaliphatic diisocyanate, suitable for this monomeric diisocyanates, in particular those of the molecular weight range 140 to 400, such as 1,3- and 1,4-diisocyanatocyclohexane, 2,4- and 2,6-diisocyanato-l-methylcyclohexane, 1,3- and 1,4- Bis- (isocyanatomethyl) cyclohexane, l-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), 4,4'-diisocyanatodicyclohexylmethane, 2,4'-diisocyanatodicyclohexylmethane, l-isocyanato-l-methyl -4 (3) isocyanato-methylcyclohexane, bis
- the cycloaliphatic diisocyanate from the group consisting of 1,3- and 1,4-diisocyanatocyclohexane, 2,4- and 2,6-diisocyanato-l-methylcyclohexane, 1,3- and 1,4-bis (isocyanatomethyl) cyclohexane, l-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 4,4'-diisocyanato-dicyclohexyl methane, 2,4'-diisocyanate anatodicyclohexyl methane, 1-isocyanato - 1 -methyl-
- isocyanato-methylcyclohexane and bis (isocyanatomethyl) norbornane is selected and is preferably l-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane.
- the polyisocyanate composition according to the invention consists of> 70% by weight, preferably> 85% by weight, particularly preferably> 95% by weight and very particularly preferably 100% by weight of the mixture.
- the polyisocyanate composition according to the invention can be solvent-free, but one or more solvents which are inert to the reactive groups of the components used can also be present.
- Suitable solvents are, for example, the conventional paint solvents known per se, such as. B. ethyl acetate, butyl acetate, ethylene glycol monomethyl or ethyl ether acetate, l-methoxypropyl-2- acetate, 3-methoxy-n-butyl acetate, acetone, 2-butanone, 4-methyl-2-pentanone, cyclohexanone, toluene, xylene, chlorobenzene, white spirit, more highly substituted aromatics, as described, for example, under the names Solventnaphtha, Solvesso®, Isopar ®, Nappar®, Varsol® (ExxonMobil Chemical Central Europe, Cologne, DE) and Shellsol ® (Shell Kunststoff Oil GmbH, Hamburg, DE) are commercially available, but also solvents such as propylene glycol diacetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol
- the solids content of the polyisocyanate composition according to the invention can be varied within wide limits with the preferred use of organic solvents. It is very particularly preferred here if the polyisocyanate composition according to the invention has a solids content of> 10 and ⁇ 95% by weight, preferably of> 25 and ⁇ 85% by weight.
- a process for the preparation of a polyisocyanate composition according to the invention wherein the at least one polyisocyanate based on pentamethylene diisocyanate is mixed with the at least one polyisocyanate based on a cycloaliphatic diisocyanate and / or at least one polyisocyanate based on pentamethylene diisocyanate and at least one cycloaliphatic diisocyanate and beforehand, simultaneously and / or afterwards one or more auxiliaries and additives can be added.
- a process for producing a polyisocyanate composition according to the invention is preferred, the at least one polyisocyanate based on pentamethylene diisocyanate being mixed with the at least one polyisocyanate based on a cycloaliphatic diisocyanate or at least one polyisocyanate based on pentamethylene diisocyanate and at least one cycloaliphatic diisocyanate and being mixed beforehand, simultaneously and / or afterwards one or more auxiliaries and additives can be added.
- a polyisocyanate composition according to any one of claims 1 to 5 or 6 as a crosslinking agent in a coating composition.
- the use of a polyisocyanate composition according to the invention as a crosslinking agent in a coating composition is a further subject of the invention.
- the use of pentamethylene diisocyanate in a polyisocyanate composition according to the invention to increase the chemical resistance of the coating obtained is a further subject of the invention.
- the polyisocyanate composition according to the invention is very well suited for producing a two-component system, so a two-component system containing a component A) comprising at least one polyisocyanate composition according to the invention and a component B) comprising at least one binder which is reactive toward isocyanate groups, the Component A) and / or component B) may contain at least one leveling aid and / or further auxiliaries and additives, a further subject of the invention.
- the two-component system according to the invention can be obtained, for example, by mixing the polyisocyanate composition according to the invention with the other compounds.
- the binder which is reactive toward isocyanate groups is a polyhydroxy compound, preferably a polyether polyol, polyester polyol, polycarbonate polyol or polyacrylate polyol.
- auxiliaries and additives which may be present can be, for example, cobinders, drying agents, fillers, cosolvents, colorants or effect pigments, thickeners, matting agents, calibration protection agents, tack additives, such as dispersants, thickeners, defoamers and other auxiliaries, known to the person skilled in the art act as adhesives, fungicides, bactericides, stabilizers or inhibitors and catalysts or emulsifiers.
- Another object of the invention is a method for producing a coating on a substrate, in which an inventive two-component system on the substrate applied and cured at a temperature> 25 ° C and ⁇ 150 ° C, preferably> 35 ° C and ⁇ 140 ° C, particularly preferably> 50 ° C and ⁇ 130 ° C.
- Suitable substrates are, for example, metal, glass, stone, ceramic materials, concrete, plastics, composites, textiles, leather or paper, which can optionally also be provided with conventional primers before coating.
- Particularly preferred substrates are substrates that have a surface made of metal and / or plastic.
- the polyisocyanate composition according to the invention can also be used with the blocking agents known from polyurethane chemistry, in the sense of one-component systems.
- coatings can be obtained which have improved chemical resistance, in particular with respect to sodium hydroxide solution or pancreatin, in comparison to coatings based on HDI or 2-methyl-l, 5-pentane diisocyanate.
- a coating, produced or producible by the method according to the invention, is therefore a further subject of the invention.
- a composite of the coating according to the invention and a substrate with a surface made of metal and / or plastic is a further subject of the invention.
- the NCO contents were determined titrimetrically in accordance with DIN EN ISO 11909: 2007 (binders for coating materials - isocyanate resins - general test methods).
- test sheets prepared in this way were provided with the appropriate test liquids in accordance with the gradient oven method and then subjected to a linear temperature gradient of 36 ° -68 ° C.
- the sheets thus stressed were then washed off with clear water and assessed after 1 and 24 hours in order to assess not only the direct damage but also the self-healing properties of the flare.
- the areas of a first recognizable attack of the clear lacquer were used for this assessment.
- the proportion of cyclo aliphatic polyisocyanate in the formulations is increased to a ratio of 1: 1, the formulations D, E and F show an almost similar level in terms of the tree resin resistance, but the comparative example formulation D (polyisocyanate 1 and 4) falls in the ratio 1: 1) in the caustic soda resistance, which is not desirable.
- a scratch-resistant coating is also desired, since scratches enormously impair the gloss of the surface (similar to the environmental influences).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP18208988.8A EP3660066A1 (de) | 2018-11-28 | 2018-11-28 | Polyisocyanatzusammensetzung auf basis von pentamethylendiisocyanat für beschichtungen |
PCT/EP2019/082055 WO2020109125A1 (de) | 2018-11-28 | 2019-11-21 | Polyisocyanatzusammensetzung für beschichtungen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3887423A1 true EP3887423A1 (de) | 2021-10-06 |
Family
ID=64556825
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP18208988.8A Ceased EP3660066A1 (de) | 2018-11-28 | 2018-11-28 | Polyisocyanatzusammensetzung auf basis von pentamethylendiisocyanat für beschichtungen |
EP19805971.9A Pending EP3887423A1 (de) | 2018-11-28 | 2019-11-21 | Polyisocyanatzusammensetzung für beschichtungen |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP18208988.8A Ceased EP3660066A1 (de) | 2018-11-28 | 2018-11-28 | Polyisocyanatzusammensetzung auf basis von pentamethylendiisocyanat für beschichtungen |
Country Status (6)
Country | Link |
---|---|
US (1) | US20220010053A1 (de) |
EP (2) | EP3660066A1 (de) |
JP (1) | JP2022508126A (de) |
KR (1) | KR20210097115A (de) |
CN (1) | CN113166361A (de) |
WO (1) | WO2020109125A1 (de) |
Families Citing this family (1)
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CN116640499B (zh) * | 2023-06-12 | 2023-11-17 | 东营海瑞宝新材料有限公司 | 一种聚脲防水组合物及其制备方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1493360B1 (de) | 1965-03-09 | 1970-01-15 | Upjohn Co | Verfahren zur Herstellung von an chlorhaltigen Verunreinigungen armen aliphatischen,cycloaliphatischen oder araliphatischen Polyisocyanaten |
DE1900514B2 (de) | 1969-01-07 | 1976-08-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von aliphatischen diisocyanaten |
DE3033860A1 (de) | 1980-09-09 | 1982-04-15 | Bayer Ag, 5090 Leverkusen | Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in polyurethanlacken |
DE3806276A1 (de) | 1988-02-27 | 1989-09-07 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
DE4426131A1 (de) | 1994-07-22 | 1996-01-25 | Bayer Ag | Lichtechte, lösemittelfreie Polyurethan-Beschichtungsmittel und ihre Verwendung |
DE4441418A1 (de) | 1994-11-22 | 1996-05-23 | Bayer Ag | Verfahren zur Herstellung von 3,5-Dimethylpyrazol-blockierten Polyisocyanaten |
EP0832159B1 (de) | 1995-06-07 | 2004-11-17 | The Sherwin-Williams Company | Für kraftwagen geeignete überzüge aus nicht-wässrigen dispersionen |
DE19611849A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
DE19752691A1 (de) | 1997-11-28 | 1999-06-02 | Huels Chemische Werke Ag | 2K-PUR-Beschichtungszusammensetzung |
WO2015119220A1 (ja) * | 2014-02-06 | 2015-08-13 | 三井化学株式会社 | 光学材料用重合性組成物および光学材料 |
JP6920999B2 (ja) * | 2015-03-16 | 2021-08-18 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | 1,5−ペンタメチレンジイソシアネート系ポリイソシアネート組成物 |
US11091584B2 (en) * | 2015-07-31 | 2021-08-17 | Covestro Deutschland Ag | Blocked polyisocyanate composition based on pentamethylene 1,5-diisocyanate |
US11384252B2 (en) * | 2017-02-08 | 2022-07-12 | Covestro (Netherlands) B.V. | Aqueous coating composition |
EP3585826B1 (de) * | 2017-02-22 | 2022-04-06 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur modifizierung von mindestens pentamethylendiisocyanat unter verwendung von spirocyclischen ammoniumsalzen als katalysator |
-
2018
- 2018-11-28 EP EP18208988.8A patent/EP3660066A1/de not_active Ceased
-
2019
- 2019-11-21 WO PCT/EP2019/082055 patent/WO2020109125A1/de unknown
- 2019-11-21 JP JP2021526544A patent/JP2022508126A/ja active Pending
- 2019-11-21 CN CN201980078639.2A patent/CN113166361A/zh active Pending
- 2019-11-21 US US17/294,777 patent/US20220010053A1/en active Pending
- 2019-11-21 EP EP19805971.9A patent/EP3887423A1/de active Pending
- 2019-11-21 KR KR1020217015744A patent/KR20210097115A/ko unknown
Also Published As
Publication number | Publication date |
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CN113166361A (zh) | 2021-07-23 |
US20220010053A1 (en) | 2022-01-13 |
KR20210097115A (ko) | 2021-08-06 |
EP3660066A1 (de) | 2020-06-03 |
JP2022508126A (ja) | 2022-01-19 |
WO2020109125A1 (de) | 2020-06-04 |
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