EP2912042A1 - Zusammensetzungen umfassend alkoxysilanhaltige isocyanate und saure stabilisatoren - Google Patents
Zusammensetzungen umfassend alkoxysilanhaltige isocyanate und saure stabilisatorenInfo
- Publication number
- EP2912042A1 EP2912042A1 EP13770445.8A EP13770445A EP2912042A1 EP 2912042 A1 EP2912042 A1 EP 2912042A1 EP 13770445 A EP13770445 A EP 13770445A EP 2912042 A1 EP2912042 A1 EP 2912042A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- halogen
- lewis acid
- formula
- acid
- bronstedt
- 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.)
- Withdrawn
Links
- 239000012948 isocyanate Substances 0.000 title claims abstract description 54
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title claims abstract description 50
- 239000002253 acid Substances 0.000 title claims abstract description 30
- 239000003381 stabilizer Substances 0.000 title abstract description 13
- 239000002841 Lewis acid Substances 0.000 claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 54
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 36
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000007848 Bronsted acid Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 23
- 239000004202 carbamide Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 150000001502 aryl halides Chemical class 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000003015 phosphoric acid halides Chemical class 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- -1 aliphatic hydrocarbon radical Chemical class 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 10
- 238000003776 cleavage reaction Methods 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 230000007017 scission Effects 0.000 description 10
- 239000006260 foam Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000008199 coating composition Substances 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- 229920005906 polyester polyol Polymers 0.000 description 6
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 4
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 4
- 239000010985 leather Substances 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 3
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 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
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011094 fiberboard Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- 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 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- JPIGSMKDJQPHJC-UHFFFAOYSA-N 1-(2-aminoethoxy)ethanol Chemical compound CC(O)OCCN JPIGSMKDJQPHJC-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- QPYKYDBKQYZEKG-UHFFFAOYSA-N 2,2-dimethylpropane-1,1-diol Chemical compound CC(C)(C)C(O)O QPYKYDBKQYZEKG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- HRWYHCYGVIJOEC-UHFFFAOYSA-N 2-(octoxymethyl)oxirane Chemical compound CCCCCCCCOCC1CO1 HRWYHCYGVIJOEC-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical class OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BUYHVRZQBLVJOO-UHFFFAOYSA-N 2-ethyl-2,4-dimethylhexane-1,3-diol Chemical compound CCC(C)C(O)C(C)(CC)CO BUYHVRZQBLVJOO-UHFFFAOYSA-N 0.000 description 1
- NTYQWXQLHWROSQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2,2,2-tris(sulfanyl)acetic acid Chemical compound OC(=O)C(S)(S)S.CCC(CO)(CO)CO NTYQWXQLHWROSQ-UHFFFAOYSA-N 0.000 description 1
- QOFLTGDAZLWRMJ-UHFFFAOYSA-N 2-methylpropane-1,1-diol Chemical compound CC(C)C(O)O QOFLTGDAZLWRMJ-UHFFFAOYSA-N 0.000 description 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
- IFPJFPROEPHIMI-UHFFFAOYSA-N 3-(2-hydroxyethylamino)propan-1-ol Chemical compound OCCCNCCO IFPJFPROEPHIMI-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
- GOCRPOKWZIVUQG-UHFFFAOYSA-N 3-(diethoxymethylsilyl)propan-1-amine Chemical compound CCOC(OCC)[SiH2]CCCN GOCRPOKWZIVUQG-UHFFFAOYSA-N 0.000 description 1
- ROSGJZYJHLVCJU-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propan-1-amine Chemical compound COC(OC)[SiH2]CCCN ROSGJZYJHLVCJU-UHFFFAOYSA-N 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- BUPLCMMXKFWTTA-UHFFFAOYSA-N 4-methylidene-1,3-dioxetan-2-one Chemical compound C=C1OC(=O)O1 BUPLCMMXKFWTTA-UHFFFAOYSA-N 0.000 description 1
- FVYMNKYNSBBJCT-UHFFFAOYSA-N 6-hydroxy-decanoic acid Chemical compound CCCCC(O)CCCCC(O)=O FVYMNKYNSBBJCT-UHFFFAOYSA-N 0.000 description 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XWSNOMORVOQOKF-UHFFFAOYSA-N COC(OC)[SiH2]CN Chemical compound COC(OC)[SiH2]CN XWSNOMORVOQOKF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OUQGOXCIUOCDNN-UHFFFAOYSA-N Glycidyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC1CO1 OUQGOXCIUOCDNN-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SQUHIDDWDVCWPV-UHFFFAOYSA-N OC1CCC(CC1)C(C)(C)C1CCC(CC1)O.C(C)(C)(C1=CC=C(OCCO)C=C1)C1=CC=C(OCCO)C=C1 Chemical compound OC1CCC(CC1)C(C)(C)C1CCC(CC1)O.C(C)(C)(C1=CC=C(OCCO)C=C1)C1=CC=C(OCCO)C=C1 SQUHIDDWDVCWPV-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-UHFFFAOYSA-N 0.000 description 1
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- ZDDAXDMVTIAONB-UHFFFAOYSA-N diethoxymethylsilylmethanamine Chemical compound CCOC(OCC)[SiH2]CN ZDDAXDMVTIAONB-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- QYMFNZIUDRQRSA-UHFFFAOYSA-N dimethyl butanedioate;dimethyl hexanedioate;dimethyl pentanedioate Chemical compound COC(=O)CCC(=O)OC.COC(=O)CCCC(=O)OC.COC(=O)CCCCC(=O)OC QYMFNZIUDRQRSA-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical class NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-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
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 239000013518 molded foam Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- NIJBJAZFTDPRQS-UHFFFAOYSA-N nonane-3,3-diol Chemical compound CCCCCCC(O)(O)CC NIJBJAZFTDPRQS-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- PTLZMJYQEBOHHM-UHFFFAOYSA-N oxiran-2-ylmethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC1CO1 PTLZMJYQEBOHHM-UHFFFAOYSA-N 0.000 description 1
- KYVUJPJYTYQNGJ-UHFFFAOYSA-N oxiran-2-ylmethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC1CO1 KYVUJPJYTYQNGJ-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000006223 plastic coating Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical class OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ROWWCTUMLAVVQB-UHFFFAOYSA-N triethoxysilylmethanamine Chemical compound CCO[Si](CN)(OCC)OCC ROWWCTUMLAVVQB-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
Definitions
- compositions comprising alkoxysilane-containing isocyanates
- the present invention relates to a composition
- a composition comprising (A) an isocyanate of the formula (I) OCN-A-SiR 1 R 2 R 3 (I), wherein A is a straight-chain, branched, substituted and / or unsubstituted aliphatic hydrocarbon radical having 1 to 12 Carbon atoms or a substituted or unsubstituted cycloaliphatic hydrocarbon radical having from 4 to 18 carbon atoms, wherein R 1 is selected from the group consisting of -O-R A k wherein R 2 and R 3 are each and independently selected from the group of substituents which comprise -RAII ⁇ and -O-R A i k , wherein -RAII ⁇ represents a hydrocarbon radical having 1 to 6 carbon atoms, and B) a Bronstedt or Lewis acid or a Bronstedt or Lewis acid releasing at room temperature Connection; as well as one
- a process for producing a stabilized alkoxysilane-containing isocyanate comprising the step of adding a Lewis or Bronsted acid or one at room temperature
- Alkoxysilane-containing isocyanates are valuable chemical compounds which permit the targeted formation of polymers which find versatile industrial use as silane-containing polycarbamates or silane-containing polyureas in foams, elastomers, thermoplastics, fibers, light-resistant polycarbamate coatings or adhesives.
- Synthetic access to isocyanates can be via a number of different routes.
- Dialkyl carbonate used (EP 18 586, EP 355 443, US 4,268,683, EP 990 644).
- urea route is the urea-mediated transfer of amines to isocyanates via a two-stage process.
- an amine is reacted with alcohol in the presence of urea or urea equivalents (eg, alkyl carbonates, alkyl carbamates) to form a biscarbamate, which is usually a
- the thermal cleavage of carbamates can be carried out in the gas or in the liquid phase, with or without solvent and with or without catalysts.
- Isophorone diisocyanate by cleavage of the corresponding biscarbamates in the gas phase in the tubular reactor in the presence of metallic packing at 410 ° C described.
- the preparation of carbamates in a one-pot reaction of amine, urea and alcohol with simultaneous removal of ammonia is known from EP 18 568.
- the teaching of EP 18 568 has been developed further and is described in EP 126 299, EP 126 300, EP 355 443, EP 566 925 and EP 568 782. More recent processes for the preparation of isocyanates are known from EP1512681, EP1512682, EP1512680, EP1593669, EP1602643, EP1634868, EP 209191 1.
- the reaction via the urea route leads to the formation of undesired by-products, for example in one-stage, two-stage and also alternatively multi-stage processes for the preparation of carbamates and in the subsequent thermal cleavage of the carbamates to isocyanates.
- a further object of the invention is to provide a process for the phosgene-free preparation of stabilized compositions comprising alkoxysilane-containing isocyanates, in particular to minimize the loss of reactive NCO groups and / or the formation of interfering byproducts such as isocyanate oligomers.
- composition comprising
- Substituents are selected which include -R A i k and -O-R A i k , wherein R A i k represents a hydrocarbon radical having 1 to 6 carbon atoms, and
- the problem is solved by a composition wherein B) is selected from the group comprising carboxylic acids, preferably dicarboxylic acids, mineral acids, preferably phosphoric acid, acid halides and alkyl or aryl halides.
- the problem is solved by a composition wherein the Bronsted or Lewis acid or the room temperature Bronsted or Lewis acid releasing compound is a compound of the formula (II)
- R 5 is selected from the group consisting of halogen
- R 6 is selected from the group comprising hydrogen, halogen, -CH 2 -halogen and -CO-halogen and preferably R 5 is -CH 2 -CI or -CO -CI and R 6 is hydrogen.
- the problem is solved by a composition wherein the proportion of the Bronstedt or Lewis acid or the room temperature Bronsted or Lewis acid releasing compound based on the mass of the isocyanate in the Composition 0.0001 to 1 weight percent, preferably 0.001 to 0.9 weight percent, most preferably 0.002 to 0.5 weight percent.
- the problem is solved by a composition wherein the isocyanate has the formula OCN- (CH 2 ) n -Si (OR 7 ) 3 and n 1 to 12, preferably 2 to 4 and R 7 is either methyl or ethyl.
- composition further comprising
- the problem is solved by a composition wherein the stoichiometric ratio between the total of the NCO-reactive hydroxy, thiol, -NH-, CH-acide and / or amine groups of C) to the total of the NCO groups of A) 2: 1 to 1: 2, preferably 1, 8: 1 to 1: 1, 8, most preferably 1, 6: 1 to 1: 1, 6.
- the problem underlying the invention is solved by a method for producing a polymer comprising the step of curing the
- composition according to the first aspect or an embodiment thereof.
- the problem is solved by a process for preparing a stabilized alkoxysilane-containing isocyanate comprising the step e) adding a Lewis or Bronsted acid or a Bronsted or Lewis acid-releasing compound at room temperature.
- the problem is solved by a method, further comprising the steps a1) reacting an alkoxysilanealkylamine of the formula (III)
- step a2) c) separating the alcohol of the formula R -OH after step b1) or a2) to form a reaction mixture separated from the alcohol, and d) thermal cracking of the reaction mixture separated off from the alcohol at temperatures of 180 to 280 ° C at a pressure of 0.1 to 200 mbar, wherein A is a straight-chain, branched, substituted and / or unsubstituted aliphatic hydrocarbon radical having 1 to 12
- the problem is solved by a method wherein the Bronstedt or Lewis acid or the room temperature Bronstedt or Lewis acid releasing compound of Group is selected which comprises carboxylic acids, preferably dicarboxylic acids, mineral acids, acid halides and alkyl and aryl halides.
- the problem is solved by a method wherein the Bronsted or Lewis acid or at room temperature
- R 5 is selected from the group consisting of halogen
- R 6 is selected from the group consisting of hydrogen, -CH 2 -halogen, halogen and
- R 5 is -CH 2 -CI or -CO-CI and R 6
- the problem is solved by a method wherein the proportion of the Bronstedt or Lewis acid or the Bronsted or Lewis acid releasing compound at room temperature based on the sum of the acid and the isocyanate 0.0001 to 1 weight percent, preferably 0.001 to 0.9 weight percent, most preferably 0.002 to 0.5 weight percent.
- the problem is solved by a method wherein the isocyanate has the formula OCN- (CH 2 ) n -Si (OMe) 3 and n 1 to 12, preferably 2 to 4.
- a seventh embodiment of the second aspect which is also an embodiment of the first to sixth embodiments, the problem is solved by a method wherein step b1) or step a) are carried out in a pressure distillation reactor with separation of generated ammonia.
- the problem underlying the invention is solved by using a Bronstedt or Lewis acid or a Bronstedt or Lewis acid-releasing compound at room temperature to stabilize an isocyanate of the formula (I)
- Substituents are selected which include R A i k and -O-R A i k k , wherein -RAII ⁇ is a hydrocarbon radical having 1 to 6 carbon atoms, and wherein the composition further comprises a Bronstedt or Lewis acid or a room temperature Bronsted or Lewis acid releasing compound.
- the problem is solved by a use wherein the Bronsted or Lewis acid or the room temperature Bronsted or Lewis acid releasing compound is selected from the group consisting of carboxylic acids, preferably dicarboxylic acids, mineral acids, Acid halides and alkyl and aryl halides.
- the problem is solved by use wherein the Bronsted or Lewis acid or the room temperature Bronsted or Lewis acid releasing compound is a compound of the formula (II)
- R 5 is selected from the group comprising halogen, -CO-halogen and -CH 2 -halogen, and wherein R 6 is selected from the group consisting of
- -CH 2 comprises -halogen, halogen and -CO-halogen is hydrogen and preferably R 5 is -CH 2 -Cl or -CO-CI and R 6 is hydrogen.
- Room temperature Bronstedt or Lewis acid releasing compound based on the sum of the acid and the isocyanate 0.0001 to 1 weight percent, preferably 0.001 to 0.9 weight percent, most preferably 0.002 to 0.5 weight percent.
- the problem is solved by use wherein the isocyanate has the formula OCN- (CH 2 ) n -Si (OR 7 ) 3 and n 1 to 12, preferably 2 to 4, and R 7 is either methyl or ethyl.
- the inventors of the present invention have discovered that acidic stabilizers improve the storage stability of alkoxysilane-containing products prepared by a phosgene-free process
- the inventors of the present invention have further found that the formation of undesirable by-products such as oligomers of the isocyanates in the presence of acid
- Stabilizers is surprisingly reduced.
- the invention relates to the stabilization of alkoxysilane-containing isocyanates by acid
- Stabilizers which constitute component B) of the composition according to the invention.
- a Bronsted or Lewis acid is used as component B) or substances which can release Bronstedt or Lewis acids at room temperature, for example carboxylic acids, mineral acids or halogen-containing substances such as acid halides or alkyl halides.
- Suitable compounds are still Benzyl halides such as benzyl chloride or benzyl bromide, furthermore benzoyl halides such as benzoyl chloride or benzoyl bromide, phthaloyl chloride, isophthalic acid dichloride,
- Terephthalic acid dichloride Terephthalic acid dichloride, toluic acid dichloride, oxalic acid, succinic acid or phosphoric acid.
- Particularly preferred are benzyl chloride and benzoyl chloride.
- the alkoxysilane-containing isocyanate is prepared according to the invention via a phosgene-free process.
- an acidic stabilizer more specifically, a Lewis or Bronsted acid, or a compound releasing such an acid at room temperature
- a Lewis or Bronsted acid or a compound releasing such an acid at room temperature
- the stabilizer is added to a precursor of the alkoxysilane-containing isocyanate during production, unless the stabilizer is removed or deactivated by the following synthesis steps.
- a single stabilizer may be used as well as a mixture comprising two or more stabilizers.
- Starting compounds for the process are diamines of the abovementioned formula (II), alcohols of the abovementioned formula (III) and also urea and / or urea equivalents prepared from urea.
- Suitable alkoxysilane-containing amines of the formula (II) are, for example
- Suitable alcohols of the formula R -OH are any primary and secondary aliphatic or cycloaliphatic alcohols which have a boiling point below 190 ° C. under atmospheric pressure.
- R 8 is a substituted or unsubstituted alkyl, cycloalkyl, aryl or aralkyl radical.
- C1 -C6 alkanols such as methanol, ethanol, 1-propanol, 1-butanol, 2-butanol, 1-hexanol or cyclohexanol.
- 1-butanol is used as the alcohol.
- Component A) may also contain additional di- and polyisocyanates.
- the di- and polyisocyanates used can consist of any desired aromatic, aliphatic, and / or cycloaliphatic di- and / or polyisocyanates.
- compositions of the invention may be solid, viscous, liquid and also
- compositions may also contain adjuvants and additives selected from inhibitors, organic solvents optionally containing unsaturated moieties, surfactants, oxygen and / or radical scavengers, catalysts,
- Sunscreens color whiteners, photoinitiators, photosensitizers, thixotropic agents, skin preventatives, defoamers, dyes, pigments, fillers and
- Matting agent included. The amount varies greatly from the field of application and type of auxiliary and additive.
- Suitable organic solvents are all liquid substances which do not react with other ingredients, eg. Acetone, ethyl acetate, butyl acetate, xylene, Solvesso 100, Solvesso 150, methoxypropyl acetate and dibasic ester.
- composition according to the invention may be the usual additives, such as leveling agents, for. As polysilicones or acrylates, light stabilizers, for. As sterically hindered amines, or other auxiliaries, such as. As described in EP 0 669 353, in a total amount of 0.05 to 5 wt .-% are added. Fillers and pigments such. Titanium dioxide may be added in an amount of up to 50% by weight of the total composition.
- the preparation of the composition according to the invention is preferably carried out by
- Room temperature and 220 ° C preferably between room temperature and 120 ° C and takes depending on the temperature and reaction components A) and B) between a few seconds and several hours.
- composition of the invention may be a
- Main component basic component or additive component of coating materials (eg textile, paper and leather coating), adhesives, paints, paints, powder coatings,
- thermoplastic elastomers in particular thermoplastic polyurethanes, thermosetting elastomers, foams (eg.
- Foams foams
- integral foams eg soft integral and rigid integral foams
- thermal insulation materials eg soft integral and rigid integral foams
- RIM materials materials for medical and hygienic
- composition of the invention may further comprise a main component
- composition according to the invention can be a main component
- Base component or additional component of coating compositions in particular primers, interlayers, topcoats, clearcoats, adhesives or sealing materials, particularly preferably with compounds of component C) represent.
- the composition according to the invention may be a main component, base component or additional component of liquid and pulverulent
- composition according to the invention can be a main component
- Base component or additive component of adhesive compositions for bonding metal, plastic, glass, wood, textile, paper, MDF (Medium Density Fiber Boards) or leather substrates represent.
- composition according to the invention can be a main component
- Basic component or additive component of metal coating compositions in particular for automobile bodies, motorcycles and bicycles, building parts and components
- the coating can either be used alone or be part of a layer of a multi-layer construction. It can be applied, for example, as a primer, as an intermediate layer or as a topcoat or clearcoat. The above or below the coating
- the composition according to the invention further comprises C) a compound having at least one, preferably two to four, NCO-reactive hydroxyl, thiol, -NH, CH-acid and / or amine groups.
- C) is an alcohol
- curing of the composition comprising A), B) and C) results in a polyurethane compound.
- Components A) and C) can be used in a mass ratio such that the OH: NCO ratio is between 2.0: 1, 0 and 1, 0: 2.0, preferably between 1, 8: 1, 0 and 1, 0: 1, 8 and more preferably between 1, 6: 1, 0 and 1, 0: 1, 6 is located.
- polymers and prepolymers can be obtained, preferably with an NCO number of 0-30% by weight and an OH number of 500-0 mg KOH / g and an acid number of 0-50 mg KOH / g) as well as thermoset or thermoplastic elastomers.
- compounds C in principle all compounds are suitable which have at least one, preferably at least two NCO groups reactive functional groups.
- Suitable as functional groups z For example, OH, NH 2 , NH, SH, CH-acidic groups.
- the compounds C) preferably contain 2 to 4 functional groups. Particularly preferred are alcohol groups and / or amino groups.
- Suitable diamines and polyamines are: 1,2-ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, 1,2-butylenediamine, 1,3-butylenediamine, 1,4-butylenediamine, 2- (ethylamino) ethylamine, 3- (methylamino) propylamine, 3- (cyclohexylamino) propylamine, 4,4'-diaminodicyclohexylmethane, isophoronediamine, 4,7-dioxadecane-1,10-diamine, N- (2-aminoethyl) -1,2-ethanediamine, N - (3-aminopropyl) -1, 3-propanediamine, N, N "-1, 2-ethanediylbis (1,3-propanediamine), adipic
- Tetraethylenepentamine pentaethylenehexamine, dipropylenetriamine, hydrazine, 1, 3- and 1, 4-phenylenediamine, 4,4'-diphenylmethanediamine, amino-functional polyethylene oxides or
- disecondary or primary / secondary diamines, as described, for. B. in a known manner from the corresponding diprimary diamines by reaction with a carbonyl compound, such as.
- a carbonyl compound such as.
- a ketone or aldehyde and subsequent hydrogenation or by addition of diprimary diamines to acrylic acid esters or maleic acid derivatives can be used.
- suitable amino alcohols are monoethanolamine, 3-amino-1-propanol, isopropanolamine, aminoethoxyethanol, N- (2-aminoethyl) ethanolamine, N-ethyl-ethanolamine, N-butylethanolamine, Diethanolamine, 3- (hydroxyethylamino) -1-propanol and diisopropanolamine also called mixtures.
- Examples of suitable compounds C) having SH groups are trimethylolpropane tri-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate, trimethylolpropane trimercaptoacetate and pentaerythritol tetramercaptoacetate.
- CH-acidic compounds for example, derivatives of malonic acid esters, acetylacetone and / or acetoacetic ester are suitable.
- Particularly suitable compounds C) are all in PU chemistry
- diols and polyols z.
- ethylene glycol 1, 2, 1, 3-propanediol, diethylene, dipropylene, triethylene, tetraethylene glycol, 1, 2, 1, 4-butanediol, 1, 3-Butylethylpropandiol, 1, 3-methylpropanediol, 1 , 5-pentanediol, bis (1,4-hydroxymethyl) cyclohexane (cyclohexanedimethanol), glycerol, hexanediol, neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, bisphenol A, B, C, F, norbornylene glycol, 1,4-benzyldimethanol, ethanol , 2,4-dimethyl-2-ethylhexane-1,3-diol, 1,4-and 2,3-butylene glycol, di- ⁇ -hydroxyethyl
- Suitable compounds C) are also diols and polyols which contain further functional groups contain. These are the linear or slightly branched hydroxyl-containing polyesters, polycarbonates, polycaprolactones, polyethers, polythioethers, polyesteramides, polyacrylates, polyvinyl alcohols, polyurethanes or polyacetals which are known per se. They preferably have a number-average molecular weight of from 134 to 20 000 g / mol, more preferably from 134 to 4000 g / mol. In the hydroxyl-containing polymers are preferably polyesters, polyethers, polyacrylates, polyurethanes, polyvinyl alcohols and / or
- Polycarbonates having an OH number of 5 - used 500 in mg KOH / gram).
- Dicarboxylic anhydrides corresponding dicarboxylic acid esters of lower alcohols, lactones or hydroxycarboxylic acids are prepared.
- Suitable diols and polyols for the preparation of the preferred polyester polyols are, in addition to the abovementioned diols and polyols, 2-methylpropanediol, 2,2-dimethylpropanediol, diethylene glycol, dodecanediol 1, 12, 1, 4-cyclohexanedimethanol and 1, 2 and 1, 4 -Cyclohexandiol.
- Dicarboxylic acids or derivatives suitable for preparing the polyester polyols may be aliphatic, cycloaliphatic, aromatic and / or heteroaromatic in nature and optionally substituted, e.g. B with halogen atoms, and / or unsaturated.
- Preferred dicarboxylic acids or derivatives include succinic, adipic, corkic, azelaic and sebacic acids, 2,2,4 (2,4,4) -trimethyladipic acid, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, terephthalic acid dimethyl ester, tetrahydrophthalic acid, Maleic acid, maleic anhydride and dimer fatty acids.
- Suitable polyester polyols are also those which are in a known manner by ring opening from lactones such as caprolactone and simple diols as starter molecules.
- lactones such as caprolactone and simple diols as starter molecules.
- mono- and polyesters from lactones eg. B. ⁇ -caprolactone or hydroxycarboxylic acids, eg. B. hydroxypivalic acid, ⁇ -hydroxydecanoic acid, ⁇ -hydroxycaproic acid, thioglycolic acid, can be used as starting materials for the preparation of polymers according to the invention.
- Polyesters of the polycarboxylic acids or their derivatives and polyphenols mentioned in this application the hydroquinone, bisphenol-A, 4,4'-dihydroxybiphenyl or bis (4-hydroxyphenyl) sulfone; Polyester of carbonic acid, which consists of hydroquinone, diphenylolpropane, p-xylylene glycol, ethylene glycol, butanediol or hexanediol-1, 6 and other polyols by conventional condensation reactions, eg. B.
- Polyphenols of the above type Polyester of boric acid; Polysiloxanes, such as.
- the products obtained by hydrolysis of dialkyldichlorosilanes with water and subsequent treatment with polyalcohols, the products obtainable by addition of polysiloxane dihydrides to olefins, such as allyl alcohol or acrylic acid, are suitable as starting materials for the preparation of the compounds C).
- the polyesters can be prepared in a conventional manner by condensation in one
- Method of organic chemistry Houben-Weyl; Vol. 14/2, pages 1 to 5, 21 to 23, 40 to 44, Georg Thieme Verlag, Stuttgart, 1963, or by C.R. Martens, Alkyd Resins, pages 51 to 59, Reinhold Plastics Appl. Series, Reinhold Publishing Comp., New York, 1961.
- OH-containing (meth) acrylates are also preferably used.
- Poly (meth) acrylates Be prepared by the co-polymerization of (meth) acrylates, with individual components carry OH groups, others not. Thus, a randomly distributed OH-containing polymer is generated which carries no, one or many OH groups.
- Such polymers are described under High solids hydroxyacrylics with tightly controlled molecular weight. van Leeuwen, Ben. SC Johnson Polymer, Neth.
- the diols and dicarboxylic acids or derivatives thereof used to prepare the polyesterpolyols can be used in any desired mixtures. It is also possible to use mixtures of polyester polyols and diols.
- Suitable compounds C) are also the reaction products of polycarboxylic acids and glycidic compounds, as z. B. in DE-OS 24 10 513 are described.
- glycidyl compounds that can be used are esters of 2,3-epoxy-1-propanol with monobasic acids having from 4 to 18 carbon atoms, such as
- Carbon atoms such as butylene oxide, and glycidyl ethers such as octyl glycidyl ether.
- Compounds C) may also be those compounds which carry at least one further functional group in addition to an epoxide group, such as.
- an epoxide group such as.
- carboxyl, hydroxyl, mercapto or amino groups which is capable of reacting with an isocyanate group.
- Particularly preferred are 2,3-epoxy-1-propanol and epoxidized soybean oil.
- Example 1 Preparation of the alkoxysilane-containing isocyanates according to the urea route
- IPMS isocyanatopropyltrimethoxysilane
- AMMO aminopropyltrimethoxysilane
- urea urea
- Tin dichloride of 50 ppm was performed.
- the fission gases IPMS and methanol were condensed out in two cascaded capacitors at 85 ° C and -25 ° C.
- the recovered, about 93% crude IPMS was fed to a purifying distillation, with 330 g / h IPMS were obtained with a purity of> 98.5%, which corresponds to a yield of 92%.
- 44 g / h of methanol were obtained as the top product of the cleavage and rectification.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102012219324.3A DE102012219324A1 (de) | 2012-10-23 | 2012-10-23 | Zusammensetzungen umfassend alkoxysilanhaltige Isocyanateund saure Stabilisatoren |
PCT/EP2013/069929 WO2014063895A1 (de) | 2012-10-23 | 2013-09-25 | Zusammensetzungen umfassend alkoxysilanhaltige isocyanate und saure stabilisatoren |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2912042A1 true EP2912042A1 (de) | 2015-09-02 |
Family
ID=49261525
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP13770445.8A Withdrawn EP2912042A1 (de) | 2012-10-23 | 2013-09-25 | Zusammensetzungen umfassend alkoxysilanhaltige isocyanate und saure stabilisatoren |
Country Status (6)
Country | Link |
---|---|
US (1) | US9593135B2 (de) |
EP (1) | EP2912042A1 (de) |
JP (1) | JP2015533842A (de) |
CN (1) | CN104718215A (de) |
DE (1) | DE102012219324A1 (de) |
WO (1) | WO2014063895A1 (de) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6878267B2 (ja) * | 2014-07-14 | 2021-05-26 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッドMomentive Performance Materials Inc. | 低着色および色安定なイソシアネートオルガノシランの製造プロセスおよびそれにより得られる生成物 |
EP2979851A1 (de) * | 2014-07-28 | 2016-02-03 | Evonik Degussa GmbH | Effiziente Herstellung von Composite-Halbzeugen und -Bauteilen im Nasspressverfahren unter Einsatz von hydroxyfunktionalisierten (Meth) Acrylaten, die mittels Isocyanaten oder Uretdionen duroplastisch vernetzt werden |
EP3263616B8 (de) | 2016-06-27 | 2020-01-15 | Evonik Operations GmbH | Alkoxysilan-funktionalisierte allophanat-haltige beschichtungsmittel |
US10844161B2 (en) | 2016-08-09 | 2020-11-24 | Covestro Deutschland Ag | Silane-functional polymeric polyurethanes |
KR101842254B1 (ko) * | 2017-05-17 | 2018-03-27 | 에스케이씨 주식회사 | 안정성 및 반응성이 개선된 자이릴렌디이소시아네이트 조성물, 및 이를 이용한 광학 렌즈 |
EP3501642A1 (de) | 2017-12-22 | 2019-06-26 | Covestro Deutschland AG | Verfahren zur herstellung gemischter silanterminierter polymere |
KR101954346B1 (ko) * | 2017-12-27 | 2019-03-05 | 에스케이씨 주식회사 | 안정성 및 반응성이 개선된 이소시아네이트 조성물, 및 이를 이용한 광학 렌즈 |
EP3546468B1 (de) * | 2018-03-28 | 2020-08-12 | Evonik Operations GmbH | Verfahren zur herstellung alkoxysilangruppen-haltiger isocyanate |
EP3546466B1 (de) * | 2018-03-28 | 2020-12-02 | Evonik Operations GmbH | Verfahren zur herstellung alkoxysilangruppen-haltiger isocyanate |
EP3546465B1 (de) * | 2018-03-28 | 2020-09-09 | Evonik Operations GmbH | Verfahren zur herstellung alkoxysilangruppen-haltiger isocyanate |
CN110872238B (zh) * | 2018-08-31 | 2022-07-12 | 万华化学集团股份有限公司 | 一种异氰酸酯稳定剂及其制备方法 |
JP2022505990A (ja) | 2018-10-30 | 2022-01-14 | コベストロ・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・アンド・コー・カーゲー | 層接着が改善された複層ペイント構造 |
WO2020089019A1 (de) | 2018-10-30 | 2020-05-07 | Covestro Deutschland Ag | Verfahren zur herstellung eines mehrschicht-lackaufbaus mit einer deckschicht aus silangruppen-enthaltenden prepolymeren |
EP3744748A1 (de) | 2019-05-27 | 2020-12-02 | Covestro Deutschland AG | Verfahren zur herstellung eines gemischten silanterminierten polymers |
CN112062786A (zh) * | 2020-09-15 | 2020-12-11 | 江苏华盛锂电材料股份有限公司 | 异氰酸酯硅烷偶联剂的提纯方法及异氰酸酯硅烷偶联剂 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2837770A1 (de) * | 1978-08-30 | 1980-03-13 | Basf Ag | Lagerbestaendige, fluessige carbodiimidgruppen aufweisende polyisocyanate und verfahren zu ihrer herstellung |
EP0505150A1 (de) * | 1991-03-19 | 1992-09-23 | MITSUI TOATSU CHEMICALS, Inc. | Verfahren zur Stabilisierung von Isocyanatderivaten und hierdurch stabilisierte Isocyanatzusammensetzungen |
Family Cites Families (74)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2220509A1 (en) | 1973-03-05 | 1974-10-04 | Du Pont | Glycidyl diesters of unsatd. dibasic acids - for coating compsns of low solvent content |
DE2917381A1 (de) | 1979-04-28 | 1980-11-13 | Basf Ag | Verfahren zur herstellung von imidazolen |
DE2917493A1 (de) | 1979-04-30 | 1980-11-13 | Basf Ag | Verfahren zur herstellung von aliphatischen und cycloaliphatischen di- und polyurethanen |
US4268683A (en) | 1980-02-21 | 1981-05-19 | The Dow Chemical Company | Preparation of carbamates from aromatic amines and organic carbonates |
DE3314790A1 (de) | 1983-04-23 | 1984-10-25 | Basf Ag, 6700 Ludwigshafen | Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat |
DE3314788A1 (de) | 1983-04-23 | 1984-10-25 | Basf Ag, 6700 Ludwigshafen | Mehrstufenverfahren zur herstellung von hexamethylendiisocyanat-1,6 und/oder isomeren aliphatischen diisocyanaten mit 6 kohlenstoffatomen im alkylenrest |
DE3828033A1 (de) | 1988-08-18 | 1990-03-08 | Huels Chemische Werke Ag | Kreislaufverfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
US4880845A (en) * | 1988-11-30 | 1989-11-14 | Ashland Oil, Inc. | Amino/ortho carboxylic acid ester catalyst system for isocyanate trimerization |
DE4213099A1 (de) | 1992-04-21 | 1993-10-28 | Basf Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von organischen Polyisocyanaten |
DE4231417A1 (de) | 1992-05-05 | 1993-11-11 | Huels Chemische Werke Ag | Kontinuierliches mehrstufiges Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
DE4342426A1 (de) | 1993-12-13 | 1995-06-14 | Bayer Ag | Verfahren zur Herstellung von Diurethanen und ihre Verwendung zur Herstellung von Diisocyanaten |
DE4406444A1 (de) | 1994-02-28 | 1995-08-31 | Huels Chemische Werke Ag | Hydroxyl- und uretdiongruppenhaltige Polyadditionsprodukte und Verfahren zu ihrer Herstellung sowie deren Verwendung zur Herstellung abspaltfreier Polyurethan-Pulverlacke hoher Reaktivität und die danach hergestellten Polyurethan-Pulverlacke |
US5525663A (en) * | 1994-08-18 | 1996-06-11 | Minnesota Mining And Manufacturing Company | Reactive hot-melt adhesive and/or sealing composition and method of using same |
DE19548771A1 (de) * | 1995-12-23 | 1997-06-26 | Basf Ag | Mikrozelluläres, harnstoffgruppenhaltiges Polyurethanelastomer |
JP4171530B2 (ja) * | 1996-04-15 | 2008-10-22 | 三井化学ポリウレタン株式会社 | ケイ素含有イソシアネート化合物の製造方法 |
JP4148481B2 (ja) * | 1997-11-17 | 2008-09-10 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | 室温硬化性ポリオルガノシロキサン組成物 |
JPH11343276A (ja) | 1998-03-31 | 1999-12-14 | Mitsui Chem Inc | 新規なウレタン化合物及び多環式脂肪族ジイソシアネ―トの製造方法 |
DE19857532A1 (de) | 1998-12-14 | 2000-06-15 | Degussa | Verfahren zur Herstellung von Carbamatoorganosilanen und Isocyanatoorganosilanen |
DE10015890A1 (de) | 2000-03-30 | 2001-10-11 | Degussa | Isocyanuratgruppenhaltige Polyisocyanate aus 1,4-Diisocyanato-2,2,6-trimethylcyclohexan, ein Verfahren zur Herstellung und Verwendung |
DE10058617A1 (de) | 2000-11-25 | 2002-05-29 | Degussa | UV-Härtbare Pulverlackzusammensetzungen |
DE10131525A1 (de) | 2001-07-02 | 2003-01-16 | Degussa | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten aus Isophorondiisocyanat |
DE10163826A1 (de) | 2001-12-22 | 2003-07-03 | Degussa | Strahlen härtbare Pulverlackzusammensetzungen und deren Verwendung |
DE10163825A1 (de) | 2001-12-22 | 2003-07-03 | Degussa | Pulverlackzusammensetzungen aus kristallinen Urethanacrylaten und deren Verwendung |
DE10163827A1 (de) | 2001-12-22 | 2003-07-03 | Degussa | Strahlen härtbare Pulverlackzusammensetzungen und deren Verwendung |
DE10205608A1 (de) | 2002-02-11 | 2003-08-21 | Degussa | Bei niedriger Temperatur härtbare feste uretdiongruppenhaltige Polyurethan-Pulverlackzusammensetzungen |
US7307134B2 (en) * | 2002-02-22 | 2007-12-11 | Henkel Corporation | Mixed alkoxysilyl functional polymers |
DE10253803A1 (de) | 2002-11-18 | 2004-05-27 | Degussa Ag | Verfahren zur Herstellung von aliphatischen Isocyanaten aus aromatischen Isocyanaten |
DE10338511A1 (de) | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
DE10338509A1 (de) | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
DE10338508A1 (de) | 2003-08-22 | 2005-03-17 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
DE10346957A1 (de) | 2003-10-09 | 2005-05-04 | Degussa | Hochreaktive, flüssige uretdiongruppenhaltige Polyurenthansysteme, die bei niedriger Temperatur härtbar sind |
CN100349902C (zh) * | 2003-12-22 | 2007-11-21 | 张家港市国泰华荣化工新材料有限公司 | 含异氰酸酯基团的硅烷的制备方法 |
DE102004011004A1 (de) | 2004-03-06 | 2005-09-22 | Degussa Ag | Verfahren zur Herstellung fester, hochreaktiver Uretdiongruppen haltiger Polyurethanzusammensetzungen |
DE102004011005A1 (de) | 2004-03-06 | 2005-09-22 | Degussa Ag | Bei niedriger Temperatur härtbare uretdiongruppenhaltige Polyurethanzusammensetzungen |
DE102004020451A1 (de) | 2004-04-27 | 2005-12-01 | Degussa Ag | Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten |
DE102004020429A1 (de) | 2004-04-27 | 2005-11-24 | Degussa Ag | Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten |
DE102004022626A1 (de) | 2004-05-07 | 2005-12-15 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
DE102004026451A1 (de) | 2004-05-29 | 2005-12-15 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
DE102004036499A1 (de) | 2004-07-28 | 2006-03-23 | Degussa Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von cycloaliphatischen Diisocyanaten |
DE102004048773A1 (de) | 2004-10-07 | 2006-04-13 | Degussa Ag | Hydroxylterminierte uretdiongruppenhaltige Polyurethanverbindungen |
DE102004048775A1 (de) | 2004-10-07 | 2006-04-13 | Degussa Ag | Hoch reaktive uretdiongruppenhaltige Polyurethanzusammensetzungen |
DE102004062588A1 (de) | 2004-12-24 | 2006-07-06 | Degussa Ag | Hochreaktive uretdiongruppenhaltige Polyurethanzusammensetzungen auf Basis von 1,4-Diisocyanatocyclohexylmethan |
JP4683581B2 (ja) * | 2005-02-02 | 2011-05-18 | 日本パーカライジング株式会社 | 水系金属材料表面処理剤、表面処理方法及び表面処理金属材料 |
DE102005013329A1 (de) | 2005-03-23 | 2006-11-16 | Degussa Ag | Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung |
US7825243B2 (en) * | 2005-06-03 | 2010-11-02 | Momentive Performance Materials Inc. | Process for the production of isocyanatosilane and silylisocyanurate |
DE102005031271A1 (de) | 2005-07-05 | 2007-01-18 | Degussa Ag | Verfahren zur Herstellung von strahlenhärtbaren Formulierungen mit erhöhtem Korrosionsschutz auf Metalluntergründen und solche Formulierungen |
US7060849B1 (en) * | 2005-09-15 | 2006-06-13 | General Electric Company | Method for production of isocyanatosilanes |
DE102005049916A1 (de) | 2005-10-17 | 2007-04-19 | Degussa Gmbh | Lagerstabile, reaktive Pulverlackzusammensetzungen mit kristallinen Bestandteilen |
DE102005050525A1 (de) | 2005-10-21 | 2007-04-26 | Degussa Gmbh | Metallfreie 1K-Polyurethansysteme |
JP4778844B2 (ja) * | 2006-06-20 | 2011-09-21 | 三井化学株式会社 | 珪素含有イソシアネート化合物の製造方法 |
DE102006042494A1 (de) | 2006-09-07 | 2008-03-27 | Evonik Degussa Gmbh | Bei niedriger Temperatur härtbare, uretdiongruppenhaltige Polyurethanzusammensetzungen mit quartären Ammoniumhalogeniden |
DE102006057118A1 (de) * | 2006-12-04 | 2008-06-05 | Wacker Chemie Ag | Verfahren zur Herstellung von Isocyanatoorganosilanen |
DE102006057838A1 (de) | 2006-12-08 | 2008-06-12 | Evonik Degussa Gmbh | Lagerstabile PUR-Pulverlackzusammensetzungen und ihre Verwendung für trübungsarme und flexible Polyurethan-Beschichtungen |
DE102006057837A1 (de) | 2006-12-08 | 2008-06-19 | Evonik Degussa Gmbh | Lagerstabile Pulverlackzusammensetzungen basierend auf säuregruppenhaltigen Polyestern, ihre Herstellung und ihre Verwendung für trübungsarme und flexible Pulverlacke |
DE102006061475A1 (de) | 2006-12-23 | 2008-06-26 | Evonik Degussa Gmbh | Verfahren zur kontinuierlichen Herstellung von (cyclo)aliphatischen Diisocyanaten |
KR20090113857A (ko) * | 2007-02-22 | 2009-11-02 | 미쓰이 가가쿠 가부시키가이샤 | 알콕시실레인 함유 수지, 변성 알콕시실레인 함유 수지 및 이들의 제조방법, 열용융 접착제 및 수지 경화물 |
US20080265201A1 (en) | 2007-04-26 | 2008-10-30 | Degussa Gmbh | Low-temperature-curable polyurethane compositions with uretdione groups, containing polymers based on polyols that carry secondary oh groups |
WO2008138855A1 (de) | 2007-05-11 | 2008-11-20 | Evonik Degussa Gmbh | Bei niedriger temperatur härtbare, uretdiongruppen aufweisende polyurethanzusammensetzungen enthaltend polymere auf der basis von sekundären oh-gruppen tragenden polyolen |
DE102007030669A1 (de) | 2007-07-02 | 2009-01-08 | Evonik Degussa Gmbh | Aminogruppenhaltige Polyester |
US20100227942A1 (en) | 2007-12-18 | 2010-09-09 | Emmanouil Spyrou | Dual-cure formulations with components containing uretdione groups |
DE102007062316A1 (de) | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | Reaktive Isocyanatzusammensetzungen |
DE102008000140A1 (de) * | 2008-01-23 | 2009-07-30 | Wacker Chemie Ag | Verfahren zur Herstellung Isocyanat-terminierter Siloxane |
DE102008007386A1 (de) | 2008-02-01 | 2009-08-06 | Evonik Degussa Gmbh | Verfahren zur Herstellung hochreaktiver uretdiongruppenhaltiger Polyurethanzusammensetzungen im Dryblend |
DE102008002703A1 (de) | 2008-06-27 | 2009-12-31 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die metallfreie Acetylacetonate enthalten |
DE102009027392A1 (de) | 2009-07-01 | 2011-01-05 | Evonik Degussa Gmbh | Zusammensetzung auf der Basis von Diisocyanaten aus nachwachsenden Rohstoffen |
DE102009027395A1 (de) | 2009-07-01 | 2011-01-05 | Evonik Degussa Gmbh | Reaktive Derivate auf Basis Dianhydrohexitol basierender Isocyanate |
DE102009027394A1 (de) | 2009-07-01 | 2011-01-05 | Evonik Degussa Gmbh | Verwendung von Isocyanaten auf der Basis von nachwachsenden Rohstoffen |
US8476376B2 (en) | 2010-03-11 | 2013-07-02 | Evonik Degussa Gmbh | Heat-curing powder-lacquer compositions yielding a matte surface after curing of the coating, as well as a simple method for production of same |
US20110237740A1 (en) * | 2010-03-29 | 2011-09-29 | Momentive Performance Materials Inc. | Blend of silylated polyurethane containing polydiorganosiloxane and silylated polyurethane and substrates containing same and process of making said substrates |
DE102010029235A1 (de) | 2010-05-21 | 2011-11-24 | Evonik Degussa Gmbh | Hydrophile Polyisocyanate |
DE102010029355A1 (de) | 2010-05-27 | 2011-12-01 | Evonik Degussa Gmbh | Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper |
DE102010041247A1 (de) | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung in Lösung |
DE102011006163A1 (de) | 2011-03-25 | 2012-09-27 | Evonik Degussa Gmbh | Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten |
CN102659830A (zh) * | 2012-04-23 | 2012-09-12 | 张家港市华盛化学有限公司 | 异氰酸酯基丙基三(三甲基硅氧基)硅烷的制备方法 |
-
2012
- 2012-10-23 DE DE102012219324.3A patent/DE102012219324A1/de not_active Withdrawn
-
2013
- 2013-09-25 WO PCT/EP2013/069929 patent/WO2014063895A1/de active Application Filing
- 2013-09-25 US US14/433,186 patent/US9593135B2/en not_active Expired - Fee Related
- 2013-09-25 JP JP2015538355A patent/JP2015533842A/ja active Pending
- 2013-09-25 CN CN201380054909.9A patent/CN104718215A/zh active Pending
- 2013-09-25 EP EP13770445.8A patent/EP2912042A1/de not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2837770A1 (de) * | 1978-08-30 | 1980-03-13 | Basf Ag | Lagerbestaendige, fluessige carbodiimidgruppen aufweisende polyisocyanate und verfahren zu ihrer herstellung |
EP0505150A1 (de) * | 1991-03-19 | 1992-09-23 | MITSUI TOATSU CHEMICALS, Inc. | Verfahren zur Stabilisierung von Isocyanatderivaten und hierdurch stabilisierte Isocyanatzusammensetzungen |
Non-Patent Citations (1)
Title |
---|
See also references of WO2014063895A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20150274760A1 (en) | 2015-10-01 |
JP2015533842A (ja) | 2015-11-26 |
CN104718215A (zh) | 2015-06-17 |
WO2014063895A1 (de) | 2014-05-01 |
DE102012219324A1 (de) | 2014-04-24 |
US9593135B2 (en) | 2017-03-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2912042A1 (de) | Zusammensetzungen umfassend alkoxysilanhaltige isocyanate und saure stabilisatoren | |
DE69911775T2 (de) | Phenylalkylaminderivate, ihre verwendung als härtungsmittel in epoxidharzzusammensetzungen und sie enthaltende härtbare epoxidharzzusammensetzungen | |
EP1404740B1 (de) | Verfahren zur herstellung von aliphatischen oligocarbonatdiolen | |
WO2017119443A1 (ja) | ポリカルボジイミド組成物、ポリカルボジイミド組成物の製造方法、水分散組成物、溶液組成物、樹脂組成物および樹脂硬化物 | |
EP2418198A1 (de) | Pentamethylen-1,5-diisocyanat | |
JPH0313270B2 (de) | ||
JP2012531507A (ja) | 再生原料からのジイソシアネートをベースとする組成物 | |
WO2011000586A1 (de) | Verwendung von isocyanaten auf der basis von nachwachsenden rohstoffen | |
EP2928938B1 (de) | Strahlungshärtbare wässrige polyurethandispersionen | |
WO2011072903A1 (de) | Zusammensetzungen aus (cyclo)aliphatischen diisocyanaten und aromatischen säurehalogeniden | |
DE4319948A1 (de) | Tertiäre Aminogruppen aufweisende Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren | |
DE2555535B1 (de) | Verfahren zur herstellung von ueberzuegen | |
WO2010112157A1 (de) | Schutzlack | |
WO2011000587A1 (de) | Reaktive derivate auf basis dianhydrohexitol basierender isocyanate | |
CN107075077B (zh) | 包含至少一个酰基脲单元的可固化有机聚合物、其制备及用途 | |
JP6393122B2 (ja) | ポリイソシアネート組成物、塗料組成物及び塗膜 | |
WO2007125029A1 (de) | Hochfunktionelle, hoch- oder hyperverzweigte polyester mit niedriger säurezahl sowie deren herstellung und verwendung | |
EP0868463B1 (de) | Verbindungen mit isocyanatgruppen und verkappten gegenüber isocyanaten reaktiven gruppen | |
DE3109276A1 (de) | Neues aliphatisches triisocyanat, verfahren zu seiner herstellung und seine verwendung | |
EP0818492B1 (de) | Wässrige Bindemittelkombination bestehend aus Polyaminen, Verfahren zu ihrer Herstellung und deren Verwendung in Lacken und Beschichtungen | |
EP3288993B1 (de) | Polyurethanummantelungen mit verminderter wasseraufnahme und deren verwendung | |
WO2014048701A1 (de) | Monomerarme nco-prepolymere und ihre verwendung | |
JP2015010183A (ja) | ジイソシアネート組成物 | |
US9102780B2 (en) | Catalysts for reaction between an isocyanate and an alcohol | |
DE2641448A1 (de) | Verfahren zur herstellung von urethan- und biuretgruppen enthaltenden polyisocyanaten |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20150327 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAX | Request for extension of the european patent (deleted) | ||
17Q | First examination report despatched |
Effective date: 20180328 |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: EVONIK OPERATIONS GMBH |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20200722 |