JP2016526063A - 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
- JP2016526063A JP2016526063A JP2016513297A JP2016513297A JP2016526063A JP 2016526063 A JP2016526063 A JP 2016526063A JP 2016513297 A JP2016513297 A JP 2016513297A JP 2016513297 A JP2016513297 A JP 2016513297A JP 2016526063 A JP2016526063 A JP 2016526063A
- Authority
- JP
- Japan
- Prior art keywords
- polyisocyanate
- polyepoxide
- resin
- mixture
- catalyst system
- 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.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 64
- 239000011347 resin Substances 0.000 title claims abstract description 64
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 85
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 85
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 64
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 239000002879 Lewis base Substances 0.000 claims abstract description 17
- 150000007527 lewis bases Chemical class 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 239000011248 coating agent Substances 0.000 claims abstract description 7
- 238000000576 coating method Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 75
- 238000002156 mixing Methods 0.000 claims description 24
- -1 bisphenol A epoxides Chemical class 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 150000002118 epoxides 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
- 238000010438 heat treatment Methods 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 238000005507 spraying Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000000565 sealant Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 description 18
- 150000002513 isocyanates Chemical class 0.000 description 17
- 239000000463 material Substances 0.000 description 10
- 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 8
- 239000003085 diluting agent Substances 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000011495 polyisocyanurate Substances 0.000 description 4
- 238000003860 storage Methods 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 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
- 229920000642 polymer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 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
- 230000001419 dependent effect Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 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
- 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
- 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- 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
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-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
- 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
- 229920003319 Araldite® Polymers 0.000 description 1
- 239000004604 Blowing Agent Substances 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
- 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
- 239000004593 Epoxy Substances 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 101100112369 Fasciola hepatica Cat-1 gene 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
- 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
- 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
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 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
- 239000012267 brine Substances 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
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 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
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-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
- 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
- 150000002739 metals Chemical class 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical group CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 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
- 230000002787 reinforcement Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material 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 compound 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 compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 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
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Abstract
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 (15)
- 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。
- 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%の量で使用される請求項1に記載の方法。
- 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、
を含む請求項1又は2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3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1〜4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1〜5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が、芳香族、芳香脂肪族、及び脂肪族ポリイソシアネートからなる群から選択される請求項1〜6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が、2〜30%のNCO含有量を有するプレポリマーである請求項1〜7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1〜8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、添加される水素酸性化合物がない請求項1〜9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によって得られる、又は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11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11又は12に記載の樹脂。
- 前記少なくとも1種のポリイソシアネートが、芳香族、芳香脂肪族、及び脂肪族ポリイソシアネートからなる群から選択される請求項11〜13のいずれか1項に記載の樹脂。
- 請求項1〜10のいずれか1項に記載の方法によって得られる、若しくは得られた樹脂の、又は請求項11〜14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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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07268051A (ja) * | 1994-03-31 | 1995-10-17 | Sunstar Eng Inc | 加熱硬化性ウレタン組成物 |
JP2010540754A (ja) * | 2007-10-05 | 2010-12-24 | ダウ グローバル テクノロジーズ インコーポレイティド | イソシアネート変性エポキシ樹脂及びそのエポキシ粉体コーティング組成物 |
JP2013515133A (ja) * | 2009-12-22 | 2013-05-02 | ダウ グローバル テクノロジーズ エルエルシー | オキサゾリドン環含有付加物 |
JP2019070139A (ja) * | 2013-05-13 | 2019-05-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | イソシアネート−エポキシドハイブリッド樹脂 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2601927A (en) * | 1950-08-07 | 1952-07-01 | Wilbur G Frenzel | Hydraulic crane structure |
JPS5183697A (ja) * | 1975-01-20 | 1976-07-22 | Hitachi Ltd | |
JPS5723620A (en) * | 1980-07-18 | 1982-02-06 | Hitachi Ltd | Thermosetting resin composition |
DE3323122A1 (de) | 1983-06-27 | 1985-05-23 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur herstellung von reaktionsharzformstoffen |
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 |
DE3942890A1 (de) * | 1989-12-23 | 1991-06-27 | Bayer Ag | Verfahren zur herstellung von kunststoff-formteilen |
GB9827367D0 (en) * | 1998-12-11 | 1999-02-03 | Dow Deutschland Inc | Adhesive resin composition |
US20070142610A1 (en) * | 2005-12-15 | 2007-06-21 | Harasin Stephen J | Polyurethane elastomers comprising allophanate modified isocyanates |
US7772353B2 (en) * | 2005-12-15 | 2010-08-10 | Bayer Materialscience Llc | Fast curing aliphatic RIM elastomers |
EP2531538A1 (de) | 2010-02-02 | 2012-12-12 | Bayer Intellectual Property GmbH | Polyisocyanat-polyadditionsprodukte, ein verfahren zu ihrer herstellung und ihre verwendung |
KR102228967B1 (ko) * | 2013-07-26 | 2021-03-17 | 바스프 에스이 | 이소시아네이트-에폭시-폼 계 |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07268051A (ja) * | 1994-03-31 | 1995-10-17 | Sunstar Eng Inc | 加熱硬化性ウレタン組成物 |
JP2010540754A (ja) * | 2007-10-05 | 2010-12-24 | ダウ グローバル テクノロジーズ インコーポレイティド | イソシアネート変性エポキシ樹脂及びそのエポキシ粉体コーティング組成物 |
JP2013515133A (ja) * | 2009-12-22 | 2013-05-02 | ダウ グローバル テクノロジーズ エルエルシー | オキサゾリドン環含有付加物 |
JP2019070139A (ja) * | 2013-05-13 | 2019-05-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | イソシアネート−エポキシドハイブリッド樹脂 |
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CA2912117C (en) | 2021-06-01 |
CN105377928A (zh) | 2016-03-02 |
TR201903281T4 (tr) | 2019-04-22 |
MX2015015789A (es) | 2016-03-09 |
CN105377928B (zh) | 2021-03-09 |
KR20160007641A (ko) | 2016-01-20 |
US10329370B2 (en) | 2019-06-25 |
BR112015028273B1 (pt) | 2020-12-15 |
ES2719325T3 (es) | 2019-07-09 |
CA2912117A1 (en) | 2014-11-20 |
EP2803684A1 (de) | 2014-11-19 |
RU2015153254A3 (ja) | 2018-03-26 |
EP2997061A1 (de) | 2016-03-23 |
WO2014184082A1 (de) | 2014-11-20 |
DK2997061T3 (en) | 2019-04-23 |
US20160090436A1 (en) | 2016-03-31 |
RU2673674C2 (ru) | 2018-11-29 |
BR112015028273A2 (pt) | 2017-07-25 |
AU2014267466B2 (en) | 2017-08-10 |
EP2997061B1 (de) | 2019-01-09 |
AU2014267466A1 (en) | 2015-12-03 |
JP2019070139A (ja) | 2019-05-09 |
RU2015153254A (ru) | 2017-06-21 |
JP6824734B2 (ja) | 2021-02-03 |
MY179171A (en) | 2020-10-30 |
PT2997061T (pt) | 2019-04-01 |
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