JP6824734B2 - イソシアネート−エポキシドハイブリッド樹脂 - Google Patents
イソシアネート−エポキシドハイブリッド樹脂 Download PDFInfo
- Publication number
- JP6824734B2 JP6824734B2 JP2016513297A JP2016513297A JP6824734B2 JP 6824734 B2 JP6824734 B2 JP 6824734B2 JP 2016513297 A JP2016513297 A JP 2016513297A JP 2016513297 A JP2016513297 A JP 2016513297A JP 6824734 B2 JP6824734 B2 JP 6824734B2
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- JP
- Japan
- Prior art keywords
- mixture
- polyisocyanate
- polyepoxide
- resin
- epoxides
- 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.)
- Active
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- 229920005989 resin Polymers 0.000 title claims description 63
- 239000011347 resin Substances 0.000 title claims description 63
- 239000005056 polyisocyanate Substances 0.000 claims description 85
- 229920001228 polyisocyanate Polymers 0.000 claims description 85
- 239000000203 mixture Substances 0.000 claims description 80
- 229920000647 polyepoxide Polymers 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 56
- 239000003054 catalyst Substances 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 27
- -1 bisphenol A epoxides Chemical class 0.000 claims description 24
- 230000003197 catalytic effect Effects 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 20
- 150000002118 epoxides Chemical class 0.000 claims description 17
- 239000002879 Lewis base Substances 0.000 claims description 16
- 150000007527 lewis bases Chemical class 0.000 claims description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 238000005507 spraying Methods 0.000 claims description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000001879 gelation Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 description 18
- 150000002513 isocyanates Chemical class 0.000 description 17
- 239000003085 diluting agent Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000582 polyisocyanurate Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004970 Chain extender Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 239000004743 Polypropylene Substances 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 239000011495 polyisocyanurate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-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
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- UTFSEWQOIIZLRH-UHFFFAOYSA-N 1,7-diisocyanatoheptane Chemical compound O=C=NCCCCCCCN=C=O UTFSEWQOIIZLRH-UHFFFAOYSA-N 0.000 description 1
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- YCUKMYFJDGKQFC-UHFFFAOYSA-N 2-(octan-3-yloxymethyl)oxirane Chemical compound CCCCCC(CC)OCC1CO1 YCUKMYFJDGKQFC-UHFFFAOYSA-N 0.000 description 1
- NWLUZGJDEZBBRH-UHFFFAOYSA-N 2-(propan-2-yloxymethyl)oxirane Chemical compound CC(C)OCC1CO1 NWLUZGJDEZBBRH-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- SFJRUJUEMVAZLM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxymethyl]oxirane Chemical compound CC(C)(C)OCC1CO1 SFJRUJUEMVAZLM-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 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
- 231100000716 Acceptable daily intake Toxicity 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 101100392078 Caenorhabditis elegans cat-4 gene Proteins 0.000 description 1
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 1
- 101001042415 Cratylia mollis Mannose/glucose-specific lectin Cramoll Proteins 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 229920003344 Epilox® Polymers 0.000 description 1
- KMHZPJNVPCAUMN-UHFFFAOYSA-N Erbon Chemical compound CC(Cl)(Cl)C(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl KMHZPJNVPCAUMN-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 102100029775 Eukaryotic translation initiation factor 1 Human genes 0.000 description 1
- 101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 1
- 101001012787 Homo sapiens Eukaryotic translation initiation factor 1 Proteins 0.000 description 1
- 101000643378 Homo sapiens Serine racemase Proteins 0.000 description 1
- 101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 1
- BESPHNLGXUYLDD-UHFFFAOYSA-N O=C1C=C(CC(C)(C)C1)C.CC1CCCCC1 Chemical compound O=C1C=C(CC(C)(C)C1)C.CC1CCCCC1 BESPHNLGXUYLDD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 101100208039 Rattus norvegicus Trpv5 gene Proteins 0.000 description 1
- 101150019148 Slc7a3 gene Proteins 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- AIXMJTYHQHQJLU-UHFFFAOYSA-N chembl210858 Chemical compound O1C(CC(=O)OC)CC(C=2C=CC(O)=CC=2)=N1 AIXMJTYHQHQJLU-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 230000006698 induction Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000011089 mechanical engineering Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- SKCNNQDRNPQEFU-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]-n,n,n'-trimethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)CCCN(C)C SKCNNQDRNPQEFU-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical class CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 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
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
- C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
-
- 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
- C08G18/48—Polyethers
- C08G18/487—Polyethers containing cyclic groups
- C08G18/4883—Polyethers containing cyclic groups containing cyclic groups having at least one oxygen atom in the ring
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- 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
- 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
- C08G2190/00—Compositions for sealing or packing joints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Organic Insulating Materials (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Sealing Material Composition (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Description
(i)少なくとも1種のポリイソシアネート、少なくとも1種のポリエポキシド、及び前記触媒システムを混合し、混合物(I)を得る工程、
(ii)前記混合物(I)を金型中へ、又は所望の反応部位へ、注入(pouring)、噴霧(spraying)、又は供給(distributing)によって配置する工程、
(iii)前記混合物(I)を、前記混合物が硬化するまで、70〜100℃の範囲の温度に加熱する工程、
を含む方法に関する。
(i)少なくとも1種のポリイソシアネート、少なくとも1種のポリエポキシド、及び前記触媒システムを混合し、混合物(I)を得る工程、
(ii)前記混合物(I)を金型中へ、又は所望の反応部位へ、注入、噴霧、又は供給によって配置する工程、
(iii)前記混合物(I)を、前記混合物が硬化するまで、70〜100℃の範囲の温度に加熱する工程、
を含む樹脂に関する。
(i)少なくとも1種のポリイソシアネート、少なくとも1種のポリエポキシド、及び前記触媒システムを混合し、混合物(I)を得る工程、
(ii)前記混合物(I)を金型中へ、又は所望の反応部位へ、注入、噴霧、又は供給によって配置する工程、
(iii)前記混合物(I)を、前記混合物が硬化するまで、70〜100℃の範囲の温度に加熱する工程、
を含む実施形態1又は2に記載の方法。
前記触媒システムが、使用される前記ポリイソシアネート及びポリエポキシドの合計に基づいて、0.01〜1質量%の量で使用される方法。
(i)少なくとも1種のポリイソシアネート、少なくとも1種のポリエポキシド、及び前記触媒システムを混合し、混合物(I)を得る工程、
(ii)前記混合物(I)を金型中へ、又は所望の反応部位へ、注入、噴霧、又は供給によって配置する工程、
(iii)前記混合物(I)を、前記混合物が硬化するまで、70〜100℃の範囲の温度に加熱する工程、を含む方法。
(i)少なくとも1種のポリイソシアネート、少なくとも1種のポリエポキシド、及び前記触媒システムを混合し、混合物(I)を得る工程、
(ii)前記混合物(I)を金型中へ、又は所望の反応部位へ、注入、噴霧、又は供給によって配置する工程、
(iii)前記混合物(I)を、前記混合物が硬化するまで、70〜100℃の範囲の温度に加熱する工程、を含む方法。
ISO1:Lupranat(登録商標) M20(BASF Polyurethanes GmbH製)、31.5%のNCO含有量を有するポリマーMDI;
ISO2:Prepolymer ISO137/28(BASF Polyurethanes GmbH製)、4,4’−MDI、カルボジイミド修飾MDI、及びポリプロピレングリエングリコールに基づき、18%のNCO含有量を有する;
ISO3:Lupranat(登録商標) MP102(BASF Polyurethanes GmbH製)、4,4’−MDIに基づくプレポリマー、22.9%のNCO含有量を有する;
ISO4:Prepolymer ISO136/144(BASF Polyurethanes GmbH製)、10%のNCO含有量を有する;
エポキシド:Baxxores(登録商標)ER5400(BASF製)、ビスフェノールAエポキシド、及び反応性希釈剤に基づくエポキシド混合物、172g/eqのエポキシ当量(EEW) を有する。
Cat2:1,8−ジアザビシクロ−5,4,0−ウンデセン−7−エン(DBU);
Cat3:Polycat(登録商標)9(Airproducts製)(ビス(3−ジメチルアミノプロピル)−n,n−ジメチルプロパンジアミン);
Cat4:N−(3−(ジメチルアミノ)プロピル)−N,N’,N’−トリメチルプロパン−1,3−ジアミン;
Cat5:Thorcat535;
Cat6:Addocat(登録商標)PP(Rhein Chemie製);
Cat7:フェノールでブロックされた1,8−ジアザビシクロ−5,4,0−ウンデセン−7−エン;
WM:Citrofol(登録商標)B1可塑剤(Jungbunzlauer製)
まず最初に、ポリエポキシド及び触媒の混合物を調製し、その後、イソシアネート成分を添加し、再度混合を行なった。全ての成分の温度は25℃であった。成分の粗製は、表1に開示している。オープンタイムは、室温でShyodu gel timerを使用して測定した。材料が、60分後、まだ固化していなかった場合、Shyodu gel timerによるオープンタイムの測定は、打ち切り、硬化を視覚的に評価した。材料が、まだ流動性を有していた場合、ゲル化点には、まだ到達していなかった。並行して、材料が固化するかどうかを見るため、対応する混合物を、80℃で、60分間加熱/硬化した。Cで符号化された実施例は、比較例である。
1,8−ジアザビシクロ−5,4,0−ウンデセン−7−エンの特定の濃度との組み合わせで、ポリイソシアネート及びポリエポキシドの比率が、本発明に必須であるので、この状況を以下の実験で説明する。この場合、室温でのオープンタイムは、視覚的に測定した。これらの実験において、目的としている限界値は、室温で、120分より大きいオープンタイムであり、試験は、その時間に到達したときに打ち切った。並行して、対応する混合物を、オーブン中で、90℃で、120分反応した。前の実験と同様に、まず、ポリエポキシドを触媒2と前混合した。その後、この混合物の一部を、ポリイソシアネートと混合した。表2は、反応混合物の定量的な画分、ポリエポキシド、ポリイソシアネート、及び触媒の混合物に基づいた触媒の割合、及びポリイソシアネートのポリエポキシドに対する当量比を示す。
C7は、純粋なDBUがポリイソシアネートと、非相溶性を示すことを明らかにしたので、以下の実験における目的は、ポリイソシアネート、ポリエポキシド、及び触媒の本発明の混合物が、硬化のために必要であり、DBUとポリイソシアネートの組み合わせが、望ましい結果につながらないことを示すことである。
ポリイソシアネート、ポリエポキシド、及び触媒の本発明の混合物がまた、極めて優れた機械的特性も有することを示すため、実験I11及びI12を実行した。この目的のため、成分を混合し、脱気した(真空高速ミキサー(vacuum Speedmixer)を使用した)。厚さ2mmの試験板(test plaque)を、結果として生じた混合物から生成した。硬化は、95℃で、2時間行なった。その後、材料を標準条件下で7日間保存し、その後、機械的特性を確認した。熱及び高湿条件下での時効(aging)を、加圧容器中で、水蒸気雰囲気下、130℃で、5、10、又は15時間実行した。これらの時間の後、試験試料を取り出し、乾燥し、機械的特性を確認する前に、標準条件下で24時間調整した。
Claims (10)
- 少なくとも1種のポリイソシアネートを、少なくとも1種のポリエポキシドと混合する工程を含み、前記混合する工程が、1,8−ジアザビシクロ−5,4,0−ウンデセン−7−エン、及びその誘導体からなる群から選択される、少なくとも1個の窒素原子を有する、金属を含まない少なくとも1種のルイス塩基に基づく触媒システムの存在下で行われる、樹脂を製造する方法であって、
前記触媒システムが、使用される前記ポリイソシアネート及びポリエポキシドの合計に基づいて、0.001〜1質量%の量で使用され、且つ
前記方法が、少なくとも以下の工程:
(i)少なくとも1種のポリイソシアネート、少なくとも1種のポリエポキシド、及び前記触媒システムを混合し、混合物(I)を得る工程、
(ii)前記混合物(I)を金型中へ、又は所望の反応部位へ、注入、噴霧、又は供給によって配置する工程、
(iii)前記混合物(I)を、前記混合物が硬化するまで、70〜100℃の範囲の温度に加熱する工程、
を含み、
前記少なくとも1種のポリイソシアネートと少なくとも1種のポリエポキシドとの反応中に、添加される水素酸性化合物がなく、且つ、
前記少なくとも1種のポリイソシアネートが、2〜30%のNCO含有量を有するプレポリマーである、
方法。 - 前記触媒システムが、使用される前記ポリイソシアネート及びポリエポキシドの合計に基づいて、0.005〜0.75質量%の量で使用される請求項1に記載の方法。
- 前記混合物(I)が、25℃の温度で、60分を超えるゲル化時間を有する請求項2に記載の方法。
- 前記少なくとも1種のポリエポキシドが、ビスフェノールAエポキシド、ビスフェノールFエポキシド、それらの誘導体、脂肪族のジ−、又はトリ−エポキシド、及びそれらの2種以上の混合物からなる群から選択される請求項1〜3のいずれか1項に記載の方法。
- 前記少なくとも1種のポリイソシアネートと少なくとも1種のポリエポキシドとの反応中に、使用されるエポキシド以外のイソシアネート反応性化合物がない請求項1〜4のいずれか1項に記載の方法。
- 前記少なくとも1種のポリイソシアネートの、前記少なくとも1種のポリエポキシドに対する当量比が、0.25:1〜5000:1の範囲である請求項1〜5のいずれか1項に記載の方法。
- 少なくとも1種のポリイソシアネートの、少なくとも1種のポリエポキシドとの混合を含む方法によって得られた樹脂であって、前記混合が、1,8−ジアザビシクロ−5,4,0−ウンデセン−7−エン、及びその誘導体からなる群から選択される、少なくとも1個の窒素原子を有する、金属を含まない少なくとも1種のルイス塩基に基づく触媒システムの存在下で行われ、
前記触媒システムが、使用される前記ポリイソシアネート及びポリエポキシドの合計に基づいて、0.001〜1質量%の量で使用され、且つ
前記方法が、少なくとも以下の工程:
(i)少なくとも1種のポリイソシアネート、少なくとも1種のポリエポキシド、及び前記触媒システムを混合し、混合物(I)を得る工程、
(ii)前記混合物(I)を金型中へ、又は所望の反応部位へ、注入、噴霧、又は供給によって配置する工程、
(iii)前記混合物(I)を、前記混合物が硬化するまで、70〜100℃の範囲の温度に加熱する工程、
を含み、且つ、
前記少なくとも1種のポリイソシアネートが、2〜30%のNCO含有量を有するプレポリマーである、
樹脂。 - 前記触媒システムが、使用される前記ポリイソシアネート及びポリエポキシドの合計に基づいて、0.01〜1質量%の量で使用される請求項7に記載の樹脂。
- 前記少なくとも1種のポリエポキシドが、ビスフェノールAエポキシド、ビスフェノールFエポキシド、それらの誘導体、脂肪族のジ−、又はトリ−エポキシド、及びそれらの2種以上の混合物からなる群から選択される請求項7又は8に記載の樹脂。
- 請求項1〜6のいずれか1項に記載の方法によって得られた樹脂の、又は請求項7〜9のいずれか1項に記載の樹脂の、シールを製造するための、動翼、船体、若しくは車体部分用の部品を製造するための、又はコーティングのための使用方法。
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EP13167490.5A EP2803684A1 (de) | 2013-05-13 | 2013-05-13 | Isocyanat-Epoxid-Hybridharze |
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PCT/EP2014/059424 WO2014184082A1 (de) | 2013-05-13 | 2014-05-08 | Isocyanat-epoxid-hybridharze |
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EP2803684A1 (de) * | 2013-05-13 | 2014-11-19 | Basf Se | Isocyanat-Epoxid-Hybridharze |
PT3137539T (pt) | 2014-04-30 | 2018-06-26 | Basf Se | Espuma de partículas de poliuretano com revestimento de poliuretano |
CA2979128C (en) | 2015-03-11 | 2023-08-08 | Basf Se | Method for producing compact polyurethanes with improved hydrolytic stability |
MX2020011821A (es) * | 2018-05-18 | 2021-02-09 | Dow Global Technologies Llc | Componente de poliisocianato, sistema de espuma de poliuretano y articulo elaborado a partir de estos. |
WO2021100649A1 (ja) | 2019-11-18 | 2021-05-27 | 東レ株式会社 | 繊維強化複合材料の成形方法、およびそれに用いられるエポキシ樹脂組成物 |
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DE3600764A1 (de) | 1986-01-14 | 1987-07-16 | Bayer Ag | Waermehaertbare reaktionsharzgemische und ein verfahren zur herstellung von formkoerpern unter verwendung dieser gemische |
US4699931A (en) | 1986-04-25 | 1987-10-13 | Olin Corporation | Oxazolidone-modified isocyanurate foams and a composition and method for their production |
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US7772353B2 (en) * | 2005-12-15 | 2010-08-10 | Bayer Materialscience Llc | Fast curing aliphatic RIM elastomers |
US20070142610A1 (en) * | 2005-12-15 | 2007-06-21 | Harasin Stephen J | Polyurethane elastomers comprising allophanate modified isocyanates |
BRPI0816499A2 (pt) * | 2007-10-05 | 2019-09-24 | Dow Global Technologies Inc | composição de resina epóxi de revestimento em pó e artigo |
BR112012015308A2 (pt) | 2009-12-22 | 2016-03-15 | Dow Global Technologies Llc | aduto contendo anel de oxazolidona, composição de revestimento em pó curável e produto |
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ES2719325T3 (es) | 2019-07-09 |
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CN105377928A (zh) | 2016-03-02 |
RU2015153254A (ru) | 2017-06-21 |
JP2016526063A (ja) | 2016-09-01 |
BR112015028273A2 (pt) | 2017-07-25 |
DK2997061T3 (en) | 2019-04-23 |
EP2997061A1 (de) | 2016-03-23 |
CN105377928B (zh) | 2021-03-09 |
MY179171A (en) | 2020-10-30 |
PT2997061T (pt) | 2019-04-01 |
RU2015153254A3 (ja) | 2018-03-26 |
CA2912117A1 (en) | 2014-11-20 |
MX2015015789A (es) | 2016-03-09 |
KR20160007641A (ko) | 2016-01-20 |
CA2912117C (en) | 2021-06-01 |
EP2997061B1 (de) | 2019-01-09 |
RU2673674C2 (ru) | 2018-11-29 |
BR112015028273B1 (pt) | 2020-12-15 |
US20160090436A1 (en) | 2016-03-31 |
AU2014267466A1 (en) | 2015-12-03 |
EP2803684A1 (de) | 2014-11-19 |
JP2019070139A (ja) | 2019-05-09 |
US10329370B2 (en) | 2019-06-25 |
WO2014184082A1 (de) | 2014-11-20 |
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