JP2020180169A - Polyurethane foam-forming composition - Google Patents
Polyurethane foam-forming composition Download PDFInfo
- Publication number
- JP2020180169A JP2020180169A JP2019081770A JP2019081770A JP2020180169A JP 2020180169 A JP2020180169 A JP 2020180169A JP 2019081770 A JP2019081770 A JP 2019081770A JP 2019081770 A JP2019081770 A JP 2019081770A JP 2020180169 A JP2020180169 A JP 2020180169A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane foam
- halogen
- examples
- molecular weight
- diisocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 19
- 239000004814 polyurethane Substances 0.000 title claims abstract description 19
- 229920005862 polyol Polymers 0.000 claims abstract description 67
- 150000003077 polyols Chemical class 0.000 claims abstract description 64
- -1 isocyanate compound Chemical class 0.000 claims abstract description 60
- 229920005830 Polyurethane Foam Polymers 0.000 claims abstract description 41
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 41
- 239000012948 isocyanate Substances 0.000 claims abstract description 41
- 239000011496 polyurethane foam Substances 0.000 claims abstract description 41
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 39
- 229920000570 polyether Polymers 0.000 claims abstract description 39
- 150000002367 halogens Chemical class 0.000 claims abstract description 38
- 239000004088 foaming agent Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical group 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 239000003063 flame retardant Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 239000002518 antifoaming agent Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000005056 polyisocyanate Chemical class 0.000 claims description 5
- 229920001228 polyisocyanate Chemical class 0.000 claims description 5
- 230000002542 deteriorative effect Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 15
- 239000006260 foam Substances 0.000 description 15
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 238000002156 mixing Methods 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000009413 insulation Methods 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 229920005906 polyester polyol Polymers 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000005187 foaming Methods 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 150000003014 phosphoric acid esters Chemical class 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011162 core material Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000012774 insulation material Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011968 lewis acid catalyst Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 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 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004114 Ammonium polyphosphate Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-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
- WOURXYYHORRGQO-UHFFFAOYSA-N Tri(3-chloropropyl) phosphate Chemical compound ClCCCOP(=O)(OCCCCl)OCCCCl WOURXYYHORRGQO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 2
- 229920001276 ammonium polyphosphate Polymers 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000003573 thiols Chemical group 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- AWYVETCHVQGXMB-UHFFFAOYSA-N (3-hydroxyphenyl) diphenyl phosphate Chemical compound OC1=CC=CC(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)=C1 AWYVETCHVQGXMB-UHFFFAOYSA-N 0.000 description 1
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- CXIGIYYQHHRBJC-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)CCC(F)(F)F CXIGIYYQHHRBJC-UHFFFAOYSA-N 0.000 description 1
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- FHOMEEJDPLXSBF-UHFFFAOYSA-N 1,2-dichloro-1-fluoroprop-1-ene Chemical compound ClC(=C(F)Cl)C FHOMEEJDPLXSBF-UHFFFAOYSA-N 0.000 description 1
- YAOMHRRYSRRRKP-UHFFFAOYSA-N 1,2-dichloropropyl 2,3-dichloropropyl 3,3-dichloropropyl phosphate Chemical compound ClC(Cl)CCOP(=O)(OC(Cl)C(Cl)C)OCC(Cl)CCl YAOMHRRYSRRRKP-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- WVWYODXLKONLEM-UHFFFAOYSA-N 1,2-diisocyanatobutane Chemical compound O=C=NC(CC)CN=C=O WVWYODXLKONLEM-UHFFFAOYSA-N 0.000 description 1
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
- UFXYYTWJETZVHG-UHFFFAOYSA-N 1,3-diisocyanatobutane Chemical compound O=C=NC(C)CCN=C=O UFXYYTWJETZVHG-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- BFIAIMMAHAIVFT-UHFFFAOYSA-N 1-[bis(2-hydroxybutyl)amino]butan-2-ol Chemical compound CCC(O)CN(CC(O)CC)CC(O)CC BFIAIMMAHAIVFT-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 1
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 description 1
- LHNAURKRXGPVDW-UHFFFAOYSA-N 2,3-diisocyanatobutane Chemical compound O=C=NC(C)C(C)N=C=O LHNAURKRXGPVDW-UHFFFAOYSA-N 0.000 description 1
- UKXROSORAUTSSH-UHFFFAOYSA-N 2-(1,2-dichloroethyl)oxirane Chemical compound ClCC(Cl)C1CO1 UKXROSORAUTSSH-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- VTEBTXIJWDIJMV-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol propane-1,3-diol Chemical compound C(CCO)O.CC(COC(C)COC(C)CO)O VTEBTXIJWDIJMV-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- CJWBPEYRTPGWPF-UHFFFAOYSA-N 2-[bis(2-chloroethoxy)phosphoryloxy]ethyl bis(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCOP(=O)(OCCCl)OCCCl CJWBPEYRTPGWPF-UHFFFAOYSA-N 0.000 description 1
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 1
- SMSVUYQRWYTTLI-UHFFFAOYSA-L 2-ethylhexanoate;iron(2+) Chemical compound [Fe+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O SMSVUYQRWYTTLI-UHFFFAOYSA-L 0.000 description 1
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- SPEHEHYVDRYEDX-UHFFFAOYSA-N 3-methyloxan-2-one Chemical compound CC1CCCOC1=O SPEHEHYVDRYEDX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-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-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
- 241000196324 Embryophyta Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical compound N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MDBVZFGSKMWJFD-UHFFFAOYSA-N OP(O)=O.OP(O)(O)=O Chemical compound OP(O)=O.OP(O)(O)=O MDBVZFGSKMWJFD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-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
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 1
- ZGHUDSLVQAGWEY-UHFFFAOYSA-N [2-[bis(2-chloroethoxy)phosphoryloxymethyl]-3-chloro-2-(chloromethyl)propyl] bis(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCC(CCl)(CCl)COP(=O)(OCCCl)OCCCl ZGHUDSLVQAGWEY-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- ITBPIKUGMIZTJR-UHFFFAOYSA-N [bis(hydroxymethyl)amino]methanol Chemical compound OCN(CO)CO ITBPIKUGMIZTJR-UHFFFAOYSA-N 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- KRJUSWXDFZSJQD-UHFFFAOYSA-N benzoic acid;lead Chemical compound [Pb].OC(=O)C1=CC=CC=C1 KRJUSWXDFZSJQD-UHFFFAOYSA-N 0.000 description 1
- ZCGHEBMEQXMRQL-UHFFFAOYSA-N benzyl 2-carbamoylpyrrolidine-1-carboxylate Chemical compound NC(=O)C1CCCN1C(=O)OCC1=CC=CC=C1 ZCGHEBMEQXMRQL-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-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
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- DEFMLLQRTVNBOF-UHFFFAOYSA-K butan-1-olate;trichlorotitanium(1+) Chemical compound [Cl-].[Cl-].[Cl-].CCCCO[Ti+3] DEFMLLQRTVNBOF-UHFFFAOYSA-K 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- UNQHMFJVBBWADE-UHFFFAOYSA-N butane-1,1-dithiol Chemical compound CCCC(S)S UNQHMFJVBBWADE-UHFFFAOYSA-N 0.000 description 1
- ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-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
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
- GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- JJPZOIJCDNHCJP-UHFFFAOYSA-N dibutyl(sulfanylidene)tin Chemical compound CCCC[Sn](=S)CCCC JJPZOIJCDNHCJP-UHFFFAOYSA-N 0.000 description 1
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 1
- QSHZUFRQHSINTB-UHFFFAOYSA-L dibutyltin(2+);dibromide Chemical compound CCCC[Sn](Br)(Br)CCCC QSHZUFRQHSINTB-UHFFFAOYSA-L 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- DHTQKXHLXVUBCF-UHFFFAOYSA-N diethyl phenyl phosphate Chemical compound CCOP(=O)(OCC)OC1=CC=CC=C1 DHTQKXHLXVUBCF-UHFFFAOYSA-N 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- XTBBZRRBOAVBRA-UHFFFAOYSA-N dimethyl phenyl phosphate Chemical compound COP(=O)(OC)OC1=CC=CC=C1 XTBBZRRBOAVBRA-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- AAOWICMKJHPGAG-UHFFFAOYSA-N ethoxy(triethyl)stannane Chemical compound CCO[Sn](CC)(CC)CC AAOWICMKJHPGAG-UHFFFAOYSA-N 0.000 description 1
- ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 description 1
- XCRHYAQWBYDRGV-JXMROGBWSA-N ethyl (e)-3-(4-propan-2-ylphenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=C(C(C)C)C=C1 XCRHYAQWBYDRGV-JXMROGBWSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom 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
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000001905 inorganic group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical group O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000010137 moulding (plastic) Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- NXFZDTAAMQLJEC-UHFFFAOYSA-M tributyl-(2,2,2-trichloroacetyl)oxytin(1-) Chemical compound CCCC[Sn-](CCCC)(CCCC)OC(=O)C(Cl)(Cl)Cl NXFZDTAAMQLJEC-UHFFFAOYSA-M 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- KVMPUXDNESXNOH-UHFFFAOYSA-N tris(1-chloropropan-2-yl) phosphate Chemical compound ClCC(C)OP(=O)(OC(C)CCl)OC(C)CCl KVMPUXDNESXNOH-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
本開示は、ポリウレタンフォーム形成性組成物に関する。 The present disclosure relates to polyurethane foam-forming compositions.
ポリウレタンフォームは、ポリエーテルポリオール及び／又はポリエステルポリオールにイソシアネート化合物と発泡剤を混合させ、反応および発泡させることにより製造されている。 Polyurethane foam is produced by mixing an isocyanate compound and a foaming agent with a polyether polyol and / or a polyester polyol, reacting and foaming.
従来、ポリウレタンフォームを難燃化するためには、難燃剤が添加使用されてきた。難燃剤としては、リン酸エステルモノマーに代表される常温で液状の難燃剤が主に使用されてきた。 Conventionally, in order to make polyurethane foam flame-retardant, a flame retardant has been added and used. As the flame retardant, a flame retardant that is liquid at room temperature, such as a phosphoric acid ester monomer, has been mainly used.
一般に常温で液状のリン酸エステルモノマーをポリウレタンフォームの難燃剤として使用した場合、可塑化作用があるため、難燃剤の使用量の増大に伴い、ポリウレタンフォームの成形性の低下を引き起こしやすいという問題があった。 Generally, when a phosphoric acid ester monomer that is liquid at room temperature is used as a flame retardant for polyurethane foam, it has a plasticizing effect, so that there is a problem that the moldability of polyurethane foam tends to decrease as the amount of the flame retardant used increases. there were.
上記問題を解決するため、３，４−ジクロロ−１，２−エポキシブタンを開環重合して得られる塩素化ポリエーテルポリオールを用いる方法が提案されている（特許文献１）。 In order to solve the above problems, a method using a chlorinated polyether polyol obtained by ring-opening polymerization of 3,4-dichloro-1,2-epoxybutane has been proposed (Patent Document 1).
しかしながら、このような塩素化ポリエーテルポリオールには、製造する際の副反応により生成する不飽和成分等の副生成物が多く含まれており、ポリウレタンフォームの成形性に課題があった。 However, such a chlorinated polyether polyol contains a large amount of by-products such as unsaturated components produced by a side reaction during production, and there is a problem in moldability of polyurethane foam.
そこで、本発明の一態様は、成形性を低下させることなく、難燃性に優れたポリウレタンフォームを製造することができるポリウレタンフォーム形成性組成物を提供することに向けられている。 Therefore, one aspect of the present invention is directed to providing a polyurethane foam-forming composition capable of producing a polyurethane foam having excellent flame retardancy without lowering the moldability.
本発明の各態様は以下に示す［１］〜［４］である。
［１］
式（１）で示される、数平均分子量が５００以上５，０００以下で、かつ、不飽和度が０．０２０ｍｅｑ／ｇ以下のハロゲン含有ポリエーテルポリオールと、イソシアネート化合物、及び発泡剤を含有するポリウレタンフォーム形成性組成物。
Each aspect of the present invention is [1] to [4] shown below.
[1]
Polyurethane containing a halogen-containing polyether polyol having a number average molecular weight of 500 or more and 5,000 or less and an degree of unsaturation of 0.020 meq / g or less, an isocyanate compound, and a foaming agent represented by the formula (1). Foam-forming composition.
（上記式（１）中、ｍは２〜８の整数、Ｒ１は活性水素含有化合残基、Ｘはハロゲン原子を表す。）
［２］
イソシアネート化合物が、芳香族イソシアネート化合物、脂肪族イソシアネート化合物、脂環族イソシアネート化合物、及びこれらのポリイソシアネート誘導体からなる群より選択される少なくとも一種であることを特徴とする［１］に記載の組成物。
［３］
［１］乃至［２］のいずれか１項に記載のポリウレタンフォーム形成性組成物に、他のポリオール、架橋剤、触媒、整泡剤、難燃剤のうち１種又は２種以上含む、ポリウレタンフォーム形成性組成物。
［４］
［１］乃至［３］のいずれかに記載の組成物の反応生成物からなるポリウレタンフォーム。
＜ポリウレタンフォーム形成性組成物＞
本発明の一態様にかかるポリウレタンフォーム形成性組成物は、
ハロゲン含有ポリエーテルポリオールとイソシアネート化合物、及び発泡剤をを含有する。
＜＜ハロゲン含有ポリエーテルポリオール＞＞
該ハロゲン含有ポリエーテルポリオールは、
式（１）で示され、
平均分子量が５００以上５，０００以下である。
(In the above formula (1), m is an integer of 2 to 8, R 1 is an active hydrogen-containing compound residue, and X is a halogen atom.)
[2]
The composition according to [1], wherein the isocyanate compound is at least one selected from the group consisting of aromatic isocyanate compounds, aliphatic isocyanate compounds, alicyclic isocyanate compounds, and polyisocyanate derivatives thereof. ..
[3]
The polyurethane foam-forming composition according to any one of [1] to [2] contains one or more of other polyols, cross-linking agents, catalysts, defoaming agents, and flame retardants. Formable composition.
[4]
A polyurethane foam comprising the reaction product of the composition according to any one of [1] to [3].
<Polyurethane foam-forming composition>
The polyurethane foam-forming composition according to one aspect of the present invention is
It contains a halogen-containing polyether polyol, an isocyanate compound, and a foaming agent.
<< Halogen-containing polyether polyol >>
The halogen-containing polyether polyol is
Expressed by equation (1)
The average molecular weight is 500 or more and 5,000 or less.
式（１）中、Ｒ１は、活性水素含有化合物残基を表し、
Ｘはハロゲン原子を表す。
In formula (1), R 1 represents an active hydrogen-containing compound residue.
X represents a halogen atom.
式（１）中、Ｘで表されるハロゲン原子は、特に限定されるものではないが、例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。これらのうち、取扱いの容易さからフッ素原子、塩素原子、臭素原子が好ましく、フッ素原子又は塩素原子であることがさらに好ましい。 In the formula (1), the halogen atom represented by X is not particularly limited, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Of these, a fluorine atom, a chlorine atom, and a bromine atom are preferable from the viewpoint of ease of handling, and a fluorine atom or a chlorine atom is more preferable.
式（１）中、Ｒ１で表される活性水素含有化合物残基としては、特に限定されるものではないが、例えばヒドロキシ残基、カルボン酸残基、チオール残基等が挙げられる。 In the formula (1), the active hydrogen-containing compound residue represented by R 1 is not particularly limited, and examples thereof include a hydroxy residue, a carboxylic acid residue, and a thiol residue.
ヒドロキシ残基としては、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール１，３−プロパンジオール、１，３−ブタンジオール、１，４−ブタンジオール、２，３−ブタンジオール、１，６−ヘキサンジオール、１，９−ノナンジオール、２，５−ヘキサンジオール、１，３−シクロヘキサンジオール、２−メチルペンタン−２，４−ジオール、２，５−ジメチル−２，５−ヘキサンジオール、グリセリン、トリメチロールプロパン、ヘキサントリオール、ペンタエリスリトール、ジグリセリン、ソルビトール、シュークロース、グルコース、２−ナフトール、ビスフェノール、水酸基を有するポリエーテルポリオール等の残基が挙げられる。 Examples of the hydroxy residue include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butanediol. , 1,6-hexanediol, 1,9-nonanediol, 2,5-hexanediol, 1,3-cyclohexanediol, 2-methylpentane-2,4-diol, 2,5-dimethyl-2,5- Residues such as hexanediol, glycerin, trimethylolpropane, hexanetriol, pentaerythritol, diglycerin, sorbitol, shoe cloth, glucose, 2-naphthol, bisphenol, and polyether polyols having hydroxyl groups can be mentioned.
アミン残基としては、例えば、エチレンジアミン、１，３−プロピレンジアミン、１，４−又は、１，２−ブチレンジアミン等の残基が挙げられる。 Examples of the amine residue include residues such as ethylenediamine, 1,3-propylenediamine, 1,4-, and 1,2-butylenediamine.
カルボン酸残基としては、例えば、フタル酸、アジピン酸等の残基が挙げられる。 Examples of the carboxylic acid residue include residues such as phthalic acid and adipic acid.
チオール残基としては、例えば、エタンジチオール、ブタンジチオール等の残基が挙げられる。 Examples of the thiol residue include residues such as ethanedithiol and butanedithiol.
これらの活性水素含有化合物残基のうち、ハロゲン含有ポリエーテルポリオールを効率よく製造することが可能となることから、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール、１，９−ノナンジオール、２，５−ヘキサンジオール、１，６−ヘキサンジオール、２−メチルペンタン−２，４−ジオール、分子量２００以上１，０００以下のポリエーテルポリオールの残基が好ましく、トリプロピレングリコール、２，５−ヘキサンジオール、１，９−ノナンジオール、分子量が２００以上１，０００以下のポリエーテルポリオールの残基が特に好ましい。 Among these active hydrogen-containing compound residues, halogen-containing polyether polyol can be efficiently produced. Therefore, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,9-nonane Residues of diols, 2,5-hexanediols, 1,6-hexanediols, 2-methylpentane-2,4-diols, polyether polyols having a molecular weight of 200 or more and 1,000 or less are preferable, and tripropylene glycol, 2, Residues of 5-hexanediol, 1,9-nonanediol, and polyether polyols having a molecular weight of 200 or more and 1,000 or less are particularly preferable.
ハロゲン含有ポリエーテルポリオールの数平均分子量は５００以上１０，０００以下であり、取扱い性、ポリウレタン生産効率に優れたものとなることから、数平均分子量５００以上５，０００以下であることが好ましく、５００以上３，０００以下であることが特に好ましい。 The number average molecular weight of the halogen-containing polyether polyol is 500 or more and 10,000 or less, and it is excellent in handleability and polyurethane production efficiency. Therefore, the number average molecular weight is preferably 500 or more and 5,000 or less, preferably 500. It is particularly preferable that the amount is 3,000 or less.
ハロゲン含有ポリエーテルポリオールの不飽和度は０．０２ｍｅｑ／ｇ以下であり、ポリウレタンとした際の硬化性が向上するため、０．０１ｍｅｑ／ｇ以下が特に好ましい。 The degree of unsaturation of the halogen-containing polyether polyol is 0.02 meq / g or less, and 0.01 meq / g or less is particularly preferable because the curability of polyurethane is improved.
ハロゲン含有ポリエーテルポリオールの質量平均分子量Ｍｗの数平均分子量Ｍｎに対する比（Ｍｗ／Ｍｎ）は、熱可塑性ポリウレタン樹脂としたとした際の硬化性が向上するため、２．００以下が好ましく、特に好ましくは１．５０以下である。ただし、ポリスチレンを標準物質としてゲルパーミエーションクロマトグラフィー測定から求めた数平均分子量をＭｎ、質量平均分子量をＭｗとする。
＜＜ハロゲン含有ポリエーテルポリオールの製造方法＞＞
ハロゲン含有ポリエーテルポリオールの製造方法としては、特に制限はなく、従来公知の製造方法で製造することができる。
The ratio (Mw / Mn) of the mass average molecular weight Mw of the halogen-containing polyether polyol to the number average molecular weight Mn is preferably 2.00 or less, and particularly preferably 2.00 or less, because the curability of the thermoplastic polyurethane resin is improved. Is 1.50 or less. However, using polystyrene as a standard substance, the number average molecular weight determined by gel permeation chromatography measurement is Mn, and the mass average molecular weight is Mw.
<< Manufacturing method of halogen-containing polyether polyol >>
The method for producing the halogen-containing polyether polyol is not particularly limited, and the halogen-containing polyether polyol can be produced by a conventionally known production method.
例えば、（Ａ）２官能以上の活性水素化合物にルイス酸触媒または複合金属シアン化物錯体触媒を用いて所定の分子量までハロゲン含有アルキレンオキシドを付加する方法；（Ｂ）２官能以上の活性水素含有化合物と、ホスファゼニウム塩又はアンモニウム塩やホスホニウム塩等のオニウム塩触媒と、ルイス酸触媒と、の存在下に、ハロゲン含有アルキレンオキシドの開環重合を行う方法；が挙げられる。 For example, (A) a method of adding a halogen-containing alkylene oxide to a bifunctional or higher functional hydrogen compound to a predetermined molecular weight using a Lewis acid catalyst or a composite metal cyanide complex catalyst; (B) a bifunctional or higher functional hydrogen-containing compound. A method of performing ring-opening polymerization of a halogen-containing alkylene oxide in the presence of an onium salt catalyst such as a phosphazenium salt or an ammonium salt or a phosphonium salt, and a Lewis acid catalyst;
ルイス酸触媒としては、例えば、アルミニウム化合物、亜鉛化合物、ホウ素化合物等が挙げられる。 Examples of the Lewis acid catalyst include aluminum compounds, zinc compounds, boron compounds and the like.
不飽和度が低く、分子量分布が狭いハロゲン含有ポリアルキレンオキシドが得やすくプレポリマーとする際のハンドリング性の向上や得られるプレポリマーの硬化性が優れやすいため、（Ｂ）に記載のハロゲン含有アルキレンオキシドの開環重合を行うことによりハロゲン含有ポリエーテルポリオールを製造することが好ましい。 The halogen-containing alkylene according to (B) is described in (B) because a halogen-containing polyalkylene oxide having a low degree of unsaturation and a narrow molecular weight distribution can be easily obtained, and the handling property of the prepolymer can be improved and the curability of the obtained prepolymer can be easily obtained. It is preferable to produce a halogen-containing polyether polyol by performing ring-opening polymerization of the oxide.
ハロゲン含有ポリエーテルポリオールの製造の際に用いられるホスファゼニウム塩の構造は特に限定されるものではない。 The structure of the phosphazenium salt used in the production of the halogen-containing polyether polyol is not particularly limited.
該ホスファゼニウム塩は、例えば、式（２）で表されるホスファゼニウム塩である： The phosphazenium salt is, for example, a phosphazenium salt represented by the formula (2):
式（２）中、
Ｒ２及びＲ３は、各々独立して、
水素原子、
炭素数１〜２０の炭化水素基、
Ｒ２とＲ３とが互いに結合した環構造、
Ｒ２同士もしくはＲ３同士が互いに結合した環構造を表し；
Ｚ−は、ヒドロキシアニオン、炭素数１〜４のアルコキシアニオン、カルボキシアニオン、炭素数２〜５のアルキルカルボキシアニオン、塩素アニオン、臭素アニオン、よう素アニオン又は炭酸水素アニオンを表し；
Ｙは、炭素原子又はリン原子を表し；
ａは、
Ｙが炭素原子のとき２であり、
Ｙがリン原子のとき３である。
In equation (2),
R 2 and R 3 are independent of each other.
Hydrogen atom,
Hydrocarbon groups with 1 to 20 carbon atoms,
A ring structure in which R 2 and R 3 are bonded to each other,
It represents a ring structure R 2 together or R 3 together are bonded to each other;
Z − represents a hydroxy anion, an alkoxy anion having 1 to 4 carbon atoms, a carboxy anion, an alkyl carboxy anion having 2 to 5 carbon atoms, a chlorine anion, a bromine anion, an iodine anion or a hydrogen carbonate anion;
Y represents a carbon atom or a phosphorus atom;
a is
When Y is a carbon atom, it is 2,
It is 3 when Y is a phosphorus atom.
アンモニウム塩又はホスホニウム塩の構造は、式（３）で表される： The structure of the ammonium salt or phosphonium salt is represented by the formula (3):
式（３）中、
Ｄは、窒素原子又はリン原子を表し；
Ｒ４、Ｒ５、Ｒ６及びＲ７は、それぞれ独立して、
炭素数１〜２０の、アルキル基、アリール基、アルコキシ基、もしくは、ジアルキルアミノ基、
ハロゲン原子、又は、
水素原子を表し；
Ｅ−は、無機又は有機の基からなる対イオンを表し；
Ｒ４〜Ｒ７のうち２〜４つが結合して環状構造を形成していてもよく、またその環状構造中にヘテロ原子を含んでいてもよい。
In equation (3),
D represents a nitrogen atom or a phosphorus atom;
R 4, R 5, R 6 and R 7 are each independently,
An alkyl group, an aryl group, an alkoxy group, or a dialkylamino group having 1 to 20 carbon atoms.
Halogen atom or
Represents a hydrogen atom;
E − represents a counterion consisting of an inorganic or organic group;
Two to four of R 4 to R 7 may be bonded to form a cyclic structure, or a hetero atom may be contained in the cyclic structure.
ハロゲン含有ポリエーテルポリオールを製造する際の重合温度としては、特に限定されるものではないが、ポリアルキレンオキシドが分解して分子量分布が広がりにくく触媒活性を発現しやすいため、７０〜１５０℃の範囲であることが好ましく、さらに好ましくは９０〜１１０℃の範囲である。 The polymerization temperature for producing the halogen-containing polyether polyol is not particularly limited, but is in the range of 70 to 150 ° C. because the polyalkylene oxide is decomposed and the molecular weight distribution is difficult to spread and the catalytic activity is easily exhibited. It is preferably in the range of 90 to 110 ° C.
ハロゲン含有ポリエーテルポリオールの製造方法において、重合反応は無溶媒で行うことが好ましいが、溶媒中で行うこともできる。使用する溶媒としては、ベンゼン、トルエン、キシレン、シクロヘキサン、１，２−ジクロロエタン、クロロベンゼン、ジクロロベンゼン、１，４−ジオキサン、１，２−ジメトキシエタン等が挙げられる。
＜＜イソシアネート化合物＞＞
本発明の一態様にかかるポリウレタンフォーム形成性組成物は、イソシアネート化合物を含み、イソシアネート化合物としては特に限定されず、少なくとも２個のイソシアネート基を持つ化合物が使用できる。例えば、芳香族イソシアネート化合物、脂肪族イソシアネート化合物、脂環族イソシアネート化合物、及びこれらのポリイソシアネート誘導体等が挙げられる。
In the method for producing a halogen-containing polyether polyol, the polymerization reaction is preferably carried out without a solvent, but it can also be carried out in a solvent. Examples of the solvent used include benzene, toluene, xylene, cyclohexane, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, 1,4-dioxane, 1,2-dimethoxyethane and the like.
<< Isocyanate compound >>
The polyurethane foam-forming composition according to one aspect of the present invention contains an isocyanate compound, and the isocyanate compound is not particularly limited, and a compound having at least two isocyanate groups can be used. Examples thereof include aromatic isocyanate compounds, aliphatic isocyanate compounds, alicyclic isocyanate compounds, and polyisocyanate derivatives thereof.
この中で、芳香族イソシアネート化合物としては。例えば、トリレンジイソシアネート
（２，４−又は２，６−トリレンジイソシアネ−ト若しくはその混合物）（ＴＤＩ）、フェニレンジイソシアネート（ｍ−，ｐ−フェニレンジイソシアネート若しくはその混合物、４，４’−ジフェニルジイソシアネート、ジフェニルメタンジイソシアネート（４，４’−、２，４’又は２，２’−ジフェニルメタンジイソシアネート若しくはその混合物）（ＭＤＩ）、４，４’−トルイジンイソシアネート（ＴＯＤＩ）、４，４’−ジフェニルエーテルジイソシアネート、キシリレンジイソシアネート（１，３−又は１，４−キシリレンジイソシアネート若しくはその混合物）（ＸＤＩ）、テトラメチルキシリレンジイソシアネート（１，３−又は１，４−テトラメチルキシリレンジイソシアネート若しくはその混合物）（ＴＭＸＤＩ）、ω，ω’−ジイソシアネート−１，４−ジエチルベンゼン、ナフタレンジイソシアネート（１，５−、１，４−又は１，８−ナフタレンジイソシアネート若しくはその混合物）（ＮＤＩ）、トリフェニルメタントリイソシアネート、トリス（イソシアネートフェニル）チオホスフェート、ポリメチレンポリフェニレンポリイソシアネート、ニトロジフェニル−４，４’−ジイソシアネート、３，３’−ジメチルジフェニルメタン−４，４’−ジイソシアネート、４，４’−ジフェニルプロパンジイソシアネート、３，３’−ジメトキシジフェニル−４，４’−ジイソシアネート等が挙げられる。
脂肪族イソシアネート化合物としては。例えば、トリメチレンジイソシアネート、１，２−プロピレンジイソシアネート、ブチレンジイソシアネート（テトラメチレンジイソシアネ−ト、１，２−ブチレンジイソシアネート、２，３−ブチレンジイソシアネート、１，３−ブチレンジイソシアネート）、ヘキサメチレンジイソシアネート、ペンタメチレンジイソシアネート、２，２，４−トリメチルヘキサメチレンジイソシアネート、２，４，−トリメチルヘキサメチレンジイソシアネート、２，６−ジイソシアネートメチルカプエート、リジンジイソシアネート、リジンエステルトリイソシアネート、１，６，１１−ウンデカントリイソシアネート、１，３，６−ヘキサメチレントリイソシアネート、トリメチルヘキサメチレンジイソシアネート、デカメチレンジイソシアネート等が挙げられる。
単環式脂環族イソシアネート化合物としては、例えば、１，３−シクロペンタンジイソシアネート、１，３−シクロペンテンジイソシアネート、シクロヘキサンジイソシアネート（１，４−シクロヘキサンジイソシアネ−ト、１，３−シクロヘキサンジイソシアネート）、３−イソシアネートメチル−３，５，５−トリメチルシクロヘキシルイソシアネート（イソホロンジイソシアネート、ＩＰＤＩ）、メチレンビス（シクロヘキシルイソシアネート（４，４’−、２，４’−又は２，２’−メチレンビス（シクロヘキシルイソシアネート若しくはこれらの混合物）（水添ＭＤＩ）、メチルシクロヘキサンジイソシアネート（メチル−２，４−シクロヘキサンジイソシアネート、メチル−２，６−シクロヘキサンジイソシアネート、ビス（イソシネートメチル）シクロヘキサン（１，３−又は１，４−ビス（イソシアネートメチル）シクロヘキサン若しくはその混合物）（水添ＸＤＩ）、ダイマー酸ジイソシアネート、トランスシクロヘキサン１，４−ジイソシアネート、水素添加トリレンジイソシアネート（水添ＴＤＩ）、水素添加テトラメチルキシリレンジイソシアネート（水加ＴＭＸＤＩ）等が挙げられる。
Among these, as an aromatic isocyanate compound. For example, tolylene diisocyanate (2,4- or 2,6-tolylene diisocyanate or a mixture thereof) (TDI), phenylenediisocyanate (m-, p-phenylenediisocyanate or a mixture thereof, 4,4'-diphenyldiisocyanate). , Diphenylmethane diisocyanate (4,4'-, 2,4'or 2,2'-diphenylmethane diisocyanate or a mixture thereof) (MDI), 4,4'-toluidine isocyanate (TODI), 4,4'-diphenyl ether diisocyanate, xyl Ranged isocyanate (1,3- or 1,4-xylylene diisocyanate or a mixture thereof) (XDI), Tetramethylxylylene diisocyanate (1,3- or 1,4-tetramethylxylylene diisocyanate or a mixture thereof) (TMXDI) , Ω, ω'-diisocyanate-1,4-diethylbenzene, naphthalenediocyanate (1,5-, 1,4- or 1,8-naphthalenediocyanate or a mixture thereof) (NDI), triphenylmethane triisocyanate, tris (isocyanate) Phenyl) thiophosphate, polymethylenepolyphenylene polyisocyanate, nitrodiphenyl-4,4'-diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, 4,4'-diphenylpropanediisocyanate, 3,3'- Examples thereof include dimethoxydiphenyl-4,4'-diisocyanate.
As an aliphatic isocyanate compound. For example, trimethylene diisocyanate, 1,2-propylene diisocyanate, butylene diisocyanate (tetramethylene diisocyanate, 1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate), hexamethylene diisocyanate, Pentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,-trimethylhexamethylene diisocyanate, 2,6-diisocyanate methylcapate, lysine diisocyanate, lysine ester triisocyanate, 1,6,11-undecantry Examples thereof include isocyanate, 1,3,6-hexamethylene triisocyanate, trimethylhexamethylene diisocyanate, and decamethylene diisocyanate.
Examples of the monocyclic alicyclic isocyanate compound include 1,3-cyclopentanediisocyanate, 1,3-cyclopentenediisocyanate, cyclohexanediisocyanate (1,4-cyclohexanediisocyanate, 1,3-cyclohexanediisocyanate), and the like. 3-Isocyanate Methyl-3,5,5-trimethylcyclohexylisocyanate (isophoronediisocyanate, IPDI), methylenebis (cyclohexylisocyanate (4,4'-, 2,4'-or 2,2'-methylenebis (cyclohexylisocyanate or these) Mixture) (hydrogenated MDI), methylcyclohexanediisocyanate (methyl-2,4-cyclohexanediisocyanate, methyl-2,6-cyclohexanediisocyanate, bis (isocyanatemethyl) cyclohexane (1,3- or 1,4-bis (1,3- or 1,4-bis) (Isocyanatemethyl) cyclohexane or a mixture thereof) (hydrogenated XDI), dimerate diisocyanate, transcyclohexane 1,4-diisocyanate, hydrogenated tolylene diisocyanate (hydrogenated TDI), hydrogenated tetramethylxylylene diisocyanate (hydrogenated TMXDI), etc. Can be mentioned.
架橋環式脂環族イソシアネート化合物としては、例えば、ノルボルネンジイソシアネート、ノルボルナンジイソシアネートメチル、ビシクロヘプタントリイソシアネート、シイソシアナートメチルビシクロヘプタン、ジ（ジイソシアナートメチル）トリシクロデカン等が挙げられる。 Examples of the crosslinked alicyclic isocyanate compound include norbornene diisocyanate, norbornane diisocyanate methyl, bicycloheptane triisocyanate, siisocyanatomethylbicycloheptane, and di (diisocyanatomethyl) tricyclodecane.
なお、上記のイソシアネート化合物又はその誘導体は単独で用いてもよいし、２種以上で用いてもよい。
＜＜発泡剤＞＞
発泡剤としては、市販の物理的発泡剤及び／又は化学的発泡剤等を使用できる。特に限定されないが、例えば、物理的発泡剤としては、クロロフルオロカーボン類、ハイドロクロロフルオロオレフィン類、ハイドロクロロフルオロカーボン類、ハイドロフルオロオレフィン類、ハイドロフルオロカーボン類、パーフルオロカーボン類、塩化メチレン等の低沸点のハロゲン系ハイドロカーボン類、ペンタン、シクロペンタン等のハイドロカーボン類、空気、窒素、二酸化炭素等の気体又は低温液体等が挙げられる。化学発泡剤としては、水、有機酸、硼酸等の無機酸類、アルカリ炭酸塩類、環状カーボネート類、ジアルキルカーボネートが挙げられ、また、ポリウレタン原料と反応または熱等により分解してガスを発生させるもの等が挙げられる。
The above-mentioned isocyanate compound or its derivative may be used alone or in combination of two or more.
<< Foaming agent >>
As the foaming agent, a commercially available physical foaming agent and / or a chemical foaming agent can be used. Although not particularly limited, for example, examples of the physical foaming agent include low boiling point halogens such as chlorofluorocarbons, hydrochlorofluoroolefins, hydrochlorofluorocarbons, hydrofluoroolefins, hydrofluorocarbons, perfluorocarbons, and methylene chloride. Examples thereof include fluorocarbons, hydrocarbons such as pentane and cyclopentane, gases such as air, nitrogen and carbon dioxide, and low-temperature liquids. Examples of the chemical foaming agent include inorganic acids such as water, organic acids and boric acid, alkaline carbonates, cyclic carbonates and dialkyl carbonates, and those which generate gas by reacting with a polyurethane raw material or by heat or the like. Can be mentioned.
なかでも、オゾン破壊係数（ＯＤＰ）が小さく、温暖化係数（ＧＷＰ）が小さいことから、ＨＣＦＯ−１２３３ｚｄ、そのトランス異性体、ＨＣＦＯ−１２３３ｘｆ、ジクロローフッ化プロペン等のハイドロクロロフルオロオレフィン類、ＨＣＦＣ−１４１ｂ等のハイドロクロロフルオロカーボン類等、ＯＤＰがゼロ、小さいＧＷＰを持つため、ＨＦＯ−１２３４ｚｆ、Ｅ−ＨＦＯ−１２３４ｚｅ、Ｚ−ＨＦＯ−１２３４ｚｅ、ＨＦＯ−１２３４ｙｆ、Ｅ−ＨＦＯ−１２５５ｙｅ、Ｚ−ＨＦＯ−１２５ｙｅ、Ｅ−ＨＦＯ−１３３６ｍｚｚ、Ｚ−ＨＦＯ−１３３６ｍｚｚ、ＨＦＯ−１４３８ｍｚｚ等のハイドロフルオロオレフィン類、ＨＦＣ−１３４ａ，ＨＦＣ−２４５、ＨＦＣ−２３６、ＨＦＣ−３５６、ＨＦＣ−３６５ｍｆｃ、ＨＦＣ−２２７ｅａ等のハイドロフルオロカーボン類、プロパン、ブタン、ペンタン、ヘキサン、シクロペンタン等のハイドロカーボン類等、又は水が好ましい。
＜＜添加剤＞＞
本発明の一態様にかかるポリウレタンフォーム形成性組成物をより良好に反応、発泡させ、ポリウレタンフォームを得るために、必要に応じて他のポリオール、架橋剤、触媒、整泡剤、難燃剤等の添加剤を配合することができる。
Among them, since the ozone destruction coefficient (ODP) is small and the warming coefficient (GWP) is small, HCFO-1233zd, its trans isomer, HCFO-1233xf, hydrochlorofluoroolefins such as dichlorofluoropropene, HCFC-141b Since the ODP is zero and the GWP is small, such as hydrochlorofluorocarbons such as HFO-1234zf, E-HFO-1234ze, Z-HFO-1234ze, HFO-1234yf, E-HFO-1255ye, Z-HFO-125ye, etc. Hydrofluoroolefins such as E-HFO-1336mzz, Z-HFO-1336mzz, HFO-1438mzz, hydrofluorocarbons such as HFC-134a, HFC-245, HFC-236, HFC-356, HFC-365mfc, HFC-227ea , Hydrocarbons such as propane, butane, pentane, hexane, cyclopentane, etc., or water is preferable.
<< Additives >>
In order to better react and foam the polyurethane foam-forming composition according to one aspect of the present invention to obtain polyurethane foam, other polyols, cross-linking agents, catalysts, defoaming agents, flame retardants and the like may be used as necessary. Additives can be added.
他のポリオールとしては、特に限定されないが、ポリウレタンの製造に用いられる市販のポリオール等が挙げられる。例えば、アルキレンオキシドの開環重合等により得られるポリエーテルポリオール類、ポリエーテルポリオール中でビニルモノマーをラジカル重合して得られるポリマーポリオール類、多価アルコールと多価カルボン酸類との重縮合により得られるポリエステルポリオール類、多価アルコール類と多価カルボン酸類とアミノアルコール類との重縮合により得られるポリエステルアミドポリオール類、ラクトン類の開環重合により得られるポリラクトンポリオール類、多価アルコール類とカーボネート類との重縮合により得られるポリカーボネートポリオール類、アクリルポリオール類、ポリブタジエンポリオール及びその水素添加物類、ポリイソプレンポリオール及びその水素添加物類、部分鹸化エチレン−酢酸ビニル共重合体、大豆油やひまし油等の天然油系ポリオール類、フェノール系ポリオール等が挙げられる。なかでも、難燃性に優れるため、ポリエステルポリオール類、ポリエーテルポリオール類、フェノール系ポリオールが好ましい。これらポリオールは、一種又は二種以上混合して使用してもよい。 The other polyol is not particularly limited, and examples thereof include commercially available polyols used in the production of polyurethane. For example, polyether polyols obtained by ring-opening polymerization of alkylene oxides, polymer polyols obtained by radical polymerization of vinyl monomers in polyether polyols, and polycondensation of polyhydric alcohols and polyvalent carboxylic acids. Polyester polyols, polyesteramide polyols obtained by polycondensation of polyhydric alcohols, polyhydric carboxylic acids and aminoalcohols, polylactone polyols obtained by ring-opening polymerization of lactones, polyhydric alcohols and carbonates. Polycarbonate polyols, acrylic polyols, polybutadiene polyols and their hydrogen additives, polyisoprene polyols and their hydrogen additives, partially saponified ethylene-vinyl acetate copolymers, soybean oil, castor oil, etc. Examples thereof include natural oil-based polyols and phenol-based polyols. Of these, polyester polyols, polyether polyols, and phenolic polyols are preferable because of their excellent flame retardancy. These polyols may be used alone or in admixture of two or more.
ポリエステルポリオール類としては、二塩基酸と多価アルコールより誘導される化合物が挙げられる。特に限定されないが、例えば、アジピン酸、オルトフタル酸、テレフタル酸、イソフタル酸、無水フタル酸、コハク酸、アゼライン酸、セバシン酸、リノシール酸、ジメチルテレフタレート、ポリエチレンテレフタレートから誘導されるポリエステルポリオール等が挙げられるが、ポリエチレンテレフタレート系廃棄物、ジメチルテレフタレート系プロセス廃棄物、ナイロン系廃棄物、トリメチロールプロパンやペンタエリスリトールの廃棄物、フタル酸系ポリエステルの廃棄物より製造されたポリエステルポリオールも含む。また、ε−カプロラクトン、メチルバレロラクトン等の環状エステルの開環重合によって得られるラクトン系ポリエステルポリオール等も挙げられる。ポリエステルポリオールのなかでも、難燃性が高いため、芳香族ポリエステルポリオールが好ましい。 Examples of polyester polyols include compounds derived from dibasic acids and polyhydric alcohols. Examples thereof include, but are not limited to, adipic acid, orthophthalic acid, terephthalic acid, isophthalic acid, phthalic anhydride, succinic acid, azelaic acid, sebacic acid, linoselic acid, dimethyl terephthalate, polyester polyol derived from polyethylene terephthalate and the like. However, it also includes polyester polyols produced from polyethylene terephthalate-based waste, dimethyl terephthalate-based process waste, nylon-based waste, trimethylolpropane and pentaerythritol waste, and phthalic acid-based polyester waste. In addition, lactone-based polyester polyols obtained by ring-opening polymerization of cyclic esters such as ε-caprolactone and methylvalerolactone can also be mentioned. Among polyester polyols, aromatic polyester polyols are preferable because they have high flame retardancy.
ポリエーテルポリオール類としては、例えば、エチレンジアミン、トリレンジアミン、シュークロース、アミノアルコール、ジエチレングリコール等の開始剤に対してエチレンオキサイド、プロピレンオキサイド等のアルキレンオキサイドを開環付加重合して得られるポリエーテルポリオール化合物等が挙げられる。 Examples of the polyether polyols include polyether polyols obtained by ring-opening addition polymerization of alkylene oxides such as ethylene oxide and propylene oxide with initiators such as ethylenediamine, tolylenediamine, shoe cloth, aminoalcohol and diethylene glycol. Examples include compounds.
フェノール系ポリオールとしては、例えば、フェノール、又はノニルフェノール、アルキルフェノール等のフェノール誘導体をホルムアルデヒドとジエタノールアミン等の２級アミンやアンモニア、１級アミン等を用いてマンニッヒ変性し、エチレンオキサイド、プロピレンオキサイド等のアルキレンオキサイドを開環付加重合して得られるマンニッヒ系ポリオール等が挙げられる。 As the phenolic polyol, for example, phenol or a phenol derivative such as nonylphenol or alkylphenol is Mannich-modified with formaldehyde, a secondary amine such as diethanolamine, ammonia, a primary amine or the like, and an alkylene oxide such as ethylene oxide or propylene oxide is used. Examples thereof include a Mannich-based polyol obtained by ring-opening addition polymerization.
架橋剤としては、特に限定されないが、公知の架橋剤を使用することができる。例えば、アルカノールアミン、グリセリン、トリメチロールプロパンなどの上記の低分子量ポリオール、および／または、そのアルキレンオキサイド付加ポリオール等が挙げられる。 The cross-linking agent is not particularly limited, but a known cross-linking agent can be used. For example, the above-mentioned low molecular weight polyols such as alkanolamine, glycerin, and trimethylolpropane, and / or alkylene oxide-added polyols thereof and the like can be mentioned.
アルカノールアミンとしては、例えば、トリメタノールアミン、トリエタノールアミン、トリプロパノールアミン、トリイソプロパノールアミン、トリブタノールアミンなどのトリアルカノールアミンや、ジエタノールアミンなどのジアルカノールアミンなどの、ポリアルカノールアミンが挙げられる。 Examples of the alkanolamine include trialkanolamines such as trimethanolamine, triethanolamine, tripropanolamine, triisopropanolamine and tributanolamine, and polyalkanolamines such as dialkanolamines such as diethanolamine.
上記架橋剤の中でも、ポリウレタンフォームの成形性が良好であるため、低分子量ポリオールおよび／またはそのアルキレンオキサイド付加ポリオールが好ましい。 Among the above cross-linking agents, a low molecular weight polyol and / or an alkylene oxide-added polyol thereof is preferable because the polyurethane foam has good moldability.
触媒としては、公知の触媒を使用することができる。例えば、三級アミン系化合物、有機金属系化合物等が挙げられる。 As the catalyst, a known catalyst can be used. For example, tertiary amine compounds, organometallic compounds and the like can be mentioned.
三級アミン系化合物としては、特に限定されないが、トリエチルアミン、トリエチレンジアミン、Ｎ，Ｎ−ジメチルベンジルアミン、Ｎ−メチルモルホリン、ジアザビシクロウンデセン（別名：ＤＢＵ）等が挙げられる。これらは、単独で、もしくは２種以上を組み合わせて使用できる。 The tertiary amine compound is not particularly limited, and examples thereof include triethylamine, triethylenediamine, N, N-dimethylbenzylamine, N-methylmorpholine, and diazabicycloundecene (also known as DBU). These can be used alone or in combination of two or more.
有機金属系化合物としては、特に限定されないが、錫系化合物、及び非錫系化合物が挙げられる。 The organometallic compound is not particularly limited, and examples thereof include tin-based compounds and non-tin-based compounds.
錫系化合物としては、特に限定されないが、例えば、ジブチル錫ジクロライド、ジブチル錫オキシド、ジブチル錫ジブロマイド、ジブチル錫ジマレエート、ジブチル錫ジラウレート（別名：ＤＢＴＤＬ）、ジブチル錫ジアセテート、ジブチル錫スルファイド、トリブチル錫スルファイド、トリブチル錫オキシド、トリブチル錫アセテート、トリエチル錫エトキサイド、トリブチル錫エトキサイド、ジオクチル錫オキシド、トリブチル錫クロライド、トリブチル錫トリクロロアセテート、ジオクチル錫ジラウリレート（別名：ＤＯＴＤＬ）、２−エチルヘキサン酸錫等が挙げられる。 The tin-based compound is not particularly limited, but for example, dibutyltin dichloride, dibutyltin oxide, dibutyltin dibromide, dibutyltin dimalate, dibutyltin dilaurate (also known as DBTDL), dibutyltin diacetate, dibutyltin sulfide, and tributyltin. Examples thereof include sulfide, tributyltin oxide, tributyltin acetate, triethyltin ethoxide, tributyltin ethoxide, dioctyltin oxide, tributyltin chloride, tributyltin trichloroacetate, dioctyltin dilaurylate (also known as DOTDL), tin 2-ethylhexanoate and the like. ..
非錫系化合物としては、特に限定されないが、例えば、ジブチルチタニウムジクロライド、テトラブチルチタネート、ブトキシチタニウムトリクロライド等のチタン系、オレイン酸鉛、２−エチルヘキサン酸鉛、安息香酸鉛、ナフテン酸鉛等の鉛系、２−エチルヘキサン酸鉄、鉄アセチルアセトネート等の鉄系、安息香酸コバルト、２−エチルヘキサン酸コバルト等のコバルト系、ナフテン酸亜鉛、２−エチルヘキサン酸亜鉛等の亜鉛系、ナフテン酸ジルコニウム等が挙げられる。 The non-tin compound is not particularly limited, and for example, titanium-based compounds such as dibutyltitanium dichloride, tetrabutyl titanate, butoxytitanium trichloride, lead oleate, lead 2-ethylhexanoate, lead benzoate, lead naphthenate and the like. Lead-based, iron-based such as iron 2-ethylhexanoate and iron acetylacetonate, cobalt-based such as cobalt benzoate and cobalt 2-ethylhexanoate, zinc-based such as zinc naphthenate and zinc 2-ethylhexanoate, Examples thereof include zirconium naphthenate.
上記ウレタン化触媒の中で、ジブチル錫ジラウレート（別名：ＤＢＴＤＬ）、ジオクチル錫ジラウレート（別名：ＤＯＴＤＬ）、２−エチルヘキサン酸錫等が、反応性及び衛生性の点で好ましい。 Among the urethanization catalysts, dibutyltin dilaurate (also known as DBTDL), dioctyltin dilaurate (also known as DOTDL), tin 2-ethylhexanoate and the like are preferable in terms of reactivity and hygiene.
上記三級アミン系化合物、有機金属系化合物等の触媒は、単独でも使用できるが、２種以上を併用することもできる。 The catalysts such as the tertiary amine compound and the organometallic compound can be used alone, but two or more of them can be used in combination.
整泡剤としては、特に限定されないが、ポリウレタンフォームの製造に用いられる市販の整泡剤等が挙げられ、例えば、整泡剤としては、界面活性剤が挙げられ、有機シロキサン−ポリオキシアルキレン共重合体、シリコーン−グリース共重合体等の非イオン系界面活性剤等の有機シリコーン系界面活性剤等が挙げられる。特に限定されないが、例えば、東レ・ダウコーニング社製ＳＺ−１３２８、ＳＺ−１６４２、ＳＺ−１７２０、エボニック デグサ ジャパン社製Ｂ８４８１、Ｂ８４４３、Ｂ８４６５、Ｂ８４８６、Ｂ８４６６、Ｂ８４５０等の市販品が挙げられる。整泡剤の添加量としては、気泡構造やサイズが安定しやすいため、ポリオール１００重量部に対して０．１以上５重量部以下の範囲が好ましい。 The defoaming agent is not particularly limited, and examples thereof include commercially available defoaming agents used in the production of polyurethane foam. Examples of the defoaming agent include surfactants, and both organic siloxane and polyoxyalkylene. Examples thereof include organic silicone-based surfactants such as nonionic surfactants such as polymers and silicone-grease copolymers. Although not particularly limited, examples thereof include commercially available products such as SZ-1328, SZ-1642, SZ-1720 manufactured by Toray Dow Corning, and B8841, B8443, B8465, B8486, B8466, B8450 manufactured by Evonik Degussa Japan. The amount of the defoaming agent added is preferably in the range of 0.1 or more and 5 parts by weight or less with respect to 100 parts by weight of the polyol because the bubble structure and size are easily stable.
難燃剤としては、特に限定されないが、ポリウレタンフォームに用いられる市販の難燃剤等を使用することができる。例えば、リン酸エステル類、ハロゲン含有有機化合物、無機化合物類等からなる市販の難燃剤が挙げられる。例えば、トリス（クロロエチル）ホスフェート、トリス（クロロプロピル）ホスフェート、トリス（ジクロロプロピル）ホスフェート、テトラキス（２−クロロエチル）エチレンジホスフェート、２，２−ビス（クロロメチル）−１，３−プロパンビス（クロロエチル）ホスフェート、トリス（２，３−ジブロモプロピル）ホスフェート、トリス（トリブロモネオペンチル）ホスフェート、２，２−ビス（クロロメチル）トリメチレンビス（ビス（２−クロロエチル）ホスフェート）、ポリオキシアルキレンビスジクロロアルキルホスフェート、含ハロゲン系ホスフェートホスホネートオリゴマーエステル（大八化学工業社製ＣＲ−５３０、ＣＲ−５７０、ＣＲ−５０９等）、トリフェニルホスフェート、トリクレジルホスフェート、クレジルジフェニルホスフェート、トリ２−エチルヘキシルホスフェート、トリメチルホスフェート、トリブチルホスフェート、トリキシレニルホスフェート、トリエチルホスフェート、トリオクチルホスフェート、ジエチルフェニルホスフォネート、ジメチルフェニルホスフォネート、レゾルシノールジフェニルホスフェート、亜リン酸エチル、亜リン酸ジエチル、芳香族系リン酸オリゴマーエステル（レゾルシノールビスジフェニルホスフェート、レゾルシノールビスジキシレニルホスフェート、ビスフェノールＡビスジフェニルホスフェート、大八化学工業社製ＣＲ−７３５等） 等のハロゲン系リン酸エステル又は非ハロゲン系リン酸エステル及びそのオリゴマー、ジブロモプロパノール、ジブロモネオペンチルグリコール、テトラブロモビスフェノールＡ 等のハロゲン含有有機化合物、炭酸マグネシウム、リン酸アルミニウム、ポリリン酸アンモニウム、水酸化アルミニウム、水酸化マグネシウム、水酸化カルシウム、メラミン樹脂、クレー、三酸化アンチモン、亜鉛華、炭酸カルシウム等の無機化合物等が挙げられる。なかでも、難燃性の高さから、ハロゲン系リン酸エステル又は非ハロゲン系リン酸エステル及びそれらのオリゴマー、ポリリン酸アンモニウムが好ましい。さらに好ましくは、混合の容易性から、ＧＰＣ法によるポリスチレン換算の数平均分子量が１，０００以下のハロゲン系リン酸エステル及びそのオリゴマー、又はＧＰＣ法によるポリスチレン換算の数平均分子量が１，０００以下の非ハロゲン系リン酸エステル及びそのオリゴマーである。これら難燃剤は一種又は二種以上混合して使用してもよい。
＜ポリウレタンフォーム＞
本発明の一態様にかかる組成物の反応生成物からなるポリウレタンフォームは、例えば、本発明の一態様にかかる組成物に含まれるポリアルキレンオキシドとイソシアネート化合物と発泡剤の存在下に反応させ発泡させることにより製造することができる。
The flame retardant is not particularly limited, but a commercially available flame retardant used for polyurethane foam or the like can be used. For example, a commercially available flame retardant composed of phosphoric acid esters, halogen-containing organic compounds, inorganic compounds and the like can be mentioned. For example, tris (chloroethyl) phosphate, tris (chloropropyl) phosphate, tris (dichloropropyl) phosphate, tetrakis (2-chloroethyl) ethylenediphosphate, 2,2-bis (chloromethyl) -1,3-propanebis (chloroethyl). ) Phosphate, Tris (2,3-dibromopropyl) phosphate, Tris (tribromoneopentyl) phosphate, 2,2-bis (chloromethyl) trimethylenebis (bis (2-chloroethyl) phosphate), polyoxyalkylene bisdichloro Alkyl phosphate, halogen-containing phosphate phosphonate oligomer ester (CR-530, CR-570, CR-509, etc. manufactured by Daihachi Chemical Industry Co., Ltd.), triphenyl phosphate, tricresyl phosphate, cresildiphenyl phosphate, tri2-ethylhexyl phosphate. , Trimethyl phosphate, tributyl phosphate, trixylenyl phosphate, triethyl phosphate, trioctyl phosphate, diethylphenyl phosphate, dimethylphenyl phosphate, resorcinol diphenyl phosphate, ethyl phosphite, diethyl phosphite, aromatic phosphate Halogen-based phosphorous acid esters such as oligomeric esters (resorcinol bisdiphenyl phosphate, resorcinol bisdiphenyl phosphate, bisphenol A bisdiphenyl phosphate, CR-735 manufactured by Daihachi Chemical Industry Co., Ltd.) or non-halogen phosphate esters and their oligomers, Halogen-containing organic compounds such as dibromopropanol, dibromoneopentyl glycol, tetrabromobisphenol A, magnesium carbonate, aluminum phosphate, ammonium polyphosphate, aluminum hydroxide, magnesium hydroxide, calcium hydroxide, melamine resin, clay, antimony trioxide , Zinc flower, inorganic compounds such as calcium carbonate and the like. Of these, halogen-based phosphoric acid esters or non-halogen-based phosphoric acid esters, their oligomers, and ammonium polyphosphate are preferable because of their high flame retardancy. More preferably, from the viewpoint of ease of mixing, a halogen-based phosphoric acid ester having a polystyrene-equivalent number average molecular weight of 1,000 or less by the GPC method and an oligomer thereof, or a polystyrene-equivalent number average molecular weight of 1,000 or less by the GPC method. Non-halogen polystyrene and its oligomers. These flame retardants may be used alone or in combination of two or more.
<Polyurethane foam>
The polyurethane foam composed of the reaction product of the composition according to one aspect of the present invention is, for example, reacted in the presence of the polyalkylene oxide, the isocyanate compound contained in the composition according to one aspect of the present invention and a foaming agent to foam. It can be manufactured by.
ポリウレタン系のフォームは、軟質系と硬質系に大別されるが、本発明の一態様にかかるポリウレタンフォーム形成性組成物を用いて、ポリウレタンフォームを得ようとすると、軟質、硬質いずれにおいても、従来公知の製造方法が適用できる。
例えば、軟質系のフォームを得ようとする際には、本発明の組成物に、必要に応じて、触媒、整泡剤、架橋剤、発泡剤、連通化剤を配合した室温液状の混合液を撹拌混合した後に、適当な金型内に注入し、発泡硬化させる方法が挙げられる。
Polyurethane-based foams are roughly classified into soft-based and hard-based ones, and when a polyurethane foam-forming composition according to one aspect of the present invention is used to obtain polyurethane foam, both soft and hard foams can be obtained. Conventionally known manufacturing methods can be applied.
For example, when trying to obtain a soft foam, a room temperature liquid mixed solution containing a catalyst, a foam stabilizer, a cross-linking agent, a foaming agent, and a communicating agent, if necessary, in the composition of the present invention. After stirring and mixing, the mixture is poured into an appropriate mold and foam-cured.
例えば、軟質系のフォームを得ようとする際には、本発明の組成物に、必要に応じて、触媒、整泡剤、架橋剤、発泡剤、連通化剤を配合した室温液状の混合液を撹拌混合した後に、適当な金型内に注入し、発泡硬化させる方法が挙げられる。 For example, when trying to obtain a soft foam, a room temperature liquid mixed solution containing a catalyst, a foam stabilizer, a cross-linking agent, a foaming agent, and a communicating agent, if necessary, in the composition of the present invention. After stirring and mixing, the mixture is poured into an appropriate mold and foam-cured.
ここで、発泡（反応）前の撹拌混合液を金型内に注入する際の金型温度としては、３０以上８０℃以下が一般的で、好ましくは、４５以上、６５℃以下である。金型温度が３０℃未満であると、ポリアルキレンオキシドとイソシアネート化合物と水の反応速度が低下し、生産速度の低下に繋がる。一方、金型温度が８０℃より高いと、ポリアルキレンオキシドとイソシアネート化合物の反応に対し、水とイソシアネート化合物の反応が過度に進行し、その結果、発泡途中においてフォームが崩れたり（成形不良）、ウレア結合の局所的な増大に基因してフォームの弾性回復性や触感が悪化したりする場合がある。 Here, the mold temperature at the time of injecting the stirring mixed solution before foaming (reaction) into the mold is generally 30 or more and 80 ° C. or less, preferably 45 or more and 65 ° C. or less. If the mold temperature is less than 30 ° C., the reaction rate of the polyalkylene oxide, the isocyanate compound, and water decreases, which leads to a decrease in the production rate. On the other hand, when the mold temperature is higher than 80 ° C., the reaction between water and the isocyanate compound proceeds excessively with respect to the reaction between the polyalkylene oxide and the isocyanate compound, and as a result, the foam collapses during foaming (molding failure). The elastic resilience and tactile sensation of the foam may deteriorate due to the local increase in urea bond.
また、上記の軟質系フォームを工業的な規模で製造するには、従来公知の高圧発泡機や低圧発泡機を用いて、本発明の組成物、及び必要に応じて各種配合剤を混合することができる。この際に、本発明の組成物におけるポリアルキレンオキシドとイソシアネート化合物とは発泡（反応）直前に混合することが好ましいが、それ以外の配合剤は組成物全体の貯蔵安定性や反応性の経時変化に影響しない範囲で、ポリアルキレンオキシド又はイソシアネート化合物と予め混合しておくこともできる、それらの事前混合物は、混合後直ちに使用しても、貯留した後に必要量を適宜使用してもよい。また、２成分を超える材料を同時に投入できる材料混合部を有する発泡装置では、ポリアルキレンオキシド、イソシアネート化合物、水、その他配合剤を個別に混合部に投入することもできる。 Further, in order to produce the above-mentioned soft foam on an industrial scale, the composition of the present invention and various compounding agents are mixed, if necessary, using a conventionally known high-pressure foaming machine or low-pressure foaming machine. Can be done. At this time, it is preferable that the polyalkylene oxide and the isocyanate compound in the composition of the present invention are mixed immediately before foaming (reaction), but the other compounding agents change the storage stability and reactivity of the entire composition with time. The premixture may be used immediately after mixing or may be used in an appropriate amount after storage, as long as it does not affect the polyalkylene oxide or isocyanate compound. Further, in an effervescent apparatus having a material mixing unit capable of simultaneously charging more than two components, polyalkylene oxide, an isocyanate compound, water and other compounding agents can be individually charged into the mixing unit.
さらに、材料の混合方法としては、発泡装置のマシンヘッド混合室内で混合を行うダイナミックミキシング、送液配管内で混合するスタテイックミキング等、従来公知のいずれの方法でもよく、両者を併用してもよい。 Further, as the material mixing method, any conventionally known method such as dynamic mixing in which mixing is performed in the machine head mixing chamber of the foaming device and static mixing in which the material is mixed in the liquid feeding pipe may be used, and both may be used in combination. May be good.
上記の撹拌混合液を金型に注入し、金型内で発泡硬化させた後に脱型し、フォームを得ることになるが、脱型を円滑に行うために、予め金型に離型剤を塗布しておくことも好適である。なお、その際に使用される離型剤は、プラスチックの成形加工分野で一般的に用いられるものでよい。 The above stirring mixture is injected into a mold, foamed and cured in the mold, and then demolded to obtain a foam. In order to smoothly demold, a mold release agent is previously applied to the mold. It is also preferable to apply it. The mold release agent used at that time may be one generally used in the field of plastic molding.
なお、脱型後のフォームは、そのままでも製品として使用できるが、適用される用途によっては、従来公知の圧縮又は減圧下でフォームのセル膜に孔を空け、製品外観や製品寸法を安定させることが好ましい。 The demolded foam can be used as it is as a product, but depending on the application, holes are formed in the cell membrane of the foam under conventionally known compression or decompression to stabilize the product appearance and product dimensions. Is preferable.
本発明の一態様にかかるポリウレタンフォームは、利用される用途に特別な制限が加わるものでなく、本発明の一態様にかかる組成物の反応生成物からなるポリウレタンフォームの特徴から、自動車・車両用のシートや枕、家具・インテリア、寝装具、シューソール、スポンジ、各種クッション、テニスボール、着地マット等、軟質系のポリウレタンフォームが適用される用途に用いることができる。また、本発明の組成物の反応生成物からなるポリウレタンフォームは、断熱・保冷材、防振・吸音材、緩衝材、浮力材等の硬質系のポリウレタンフォームが適用される用途に用いることができる。例えば、漁船・大型船・冷凍貨物船・ＬＮＧ船、ＬＰＧ船、液化ガス船、コンテナーの断熱材やＦＲＰボートの芯材、大型船舶・救命艇・ブイ・浮き類の浮力材として船舶用に、冷凍車・保冷車・鉄道のコンテナー、タンクローリーの断熱材、車両・トラックの天井の断熱材としての車両用に、化学工業設備タンク・配管の断熱材、重油タンク・配管等の保温材、ＬＰＧ・ＬＮＧ低温液化ガス保冷・配管の断熱材、断熱カバー、タンク蓋用としてプラント用に、冷蔵庫・冷凍機の断熱材、エアコンの断熱部材、ショーケース・ストッカー・自動販売機・温水器・貯湯槽等の各種断熱機器の断熱材用に、さらに、住宅・オフィスビルの断熱材（壁、床下、天井、屋根下等）、断熱建材（ラミネートボード、複合パネル、サイデイング材等）、浴槽（ステンレス・ＦＲＰ・ほうろう）の断熱材、冷凍倉庫・冷蔵倉庫・農業倉庫・畜舎等の断熱材、ボイド充填（断熱サッシ）、恒温室・地域集中冷暖房の断熱材としての建築・建材用に、道路床の断熱材や振動防止材としての土木用に、その他として、椅子芯材、ドアーパネル、装飾工芸品、娯楽用具（クーラーボックス・水筒）、教材（立体地図等）、型材・治具関係、サーフィンの芯材、ＲＩＭ方式製品（スキー芯材・ラケット芯材・ハウジング類）、梱包材等が挙げられる。 The polyurethane foam according to one aspect of the present invention is not particularly limited in its intended use, and is for automobiles and vehicles because of the characteristics of the polyurethane foam composed of the reaction product of the composition according to one aspect of the present invention. It can be used in applications where soft polyurethane foam is applied, such as seats and pillows, furniture / interior, bedding, shoe soles, sponges, various cushions, tennis balls, and landing mats. Further, the polyurethane foam composed of the reaction product of the composition of the present invention can be used in applications to which a hard polyurethane foam such as a heat insulating / cooling material, a vibration-proof / sound-absorbing material, a cushioning material, and a buoyancy material is applied. .. For example, for ships such as fishing boats, large ships, frozen freight ships, LNG ships, LPG ships, liquefied gas ships, container insulation materials, core materials for FRP boats, and buoyancy materials for large ships, lifeboats, buoys, and floats. For vehicles such as refrigeration vehicles, cold storage vehicles, railway containers, tank lorry insulation materials, and vehicle / truck ceiling insulation materials, chemical industry equipment tank / piping insulation materials, heavy oil tanks / piping insulation materials, LPG / LNG low temperature liquefied gas cold insulation / pipe insulation, insulation cover, for plants for tank lids, refrigerator / refrigerator insulation, air conditioner insulation, showcases / stockers / vending machines / water heaters / hot water tanks, etc. For heat insulating materials of various heat insulating devices, heat insulating materials for houses and office buildings (walls, underfloors, ceilings, under roofs, etc.), heat insulating building materials (laminated boards, composite panels, siding materials, etc.), bathtubs (stainless steel / FRP)・ Insulation of road floors for heat insulation of roof), heat insulation of frozen warehouses, refrigerated warehouses, agricultural warehouses, barns, etc., void filling (insulation sash), heat insulation of constant temperature greenhouses and regional centralized heating and cooling For civil engineering as materials and anti-vibration materials, as well as chair core materials, door panels, decorative crafts, entertainment equipment (cooler boxes / water cylinders), teaching materials (three-dimensional maps, etc.), mold materials / jigs, surfing cores Examples include materials, RIM method products (ski core materials, racket core materials, housings), packing materials, and the like.
以下、実施例により本発明を説明するが、本実施例は何ら本発明を制限するものではない。なお、以下の実施例及び比較例で使用した原料、及び評価方法は以下に示す通りである。
＜ポリオール＞
実施例、比較例では、式（１）に示される構造をもつハロゲン含有ポリエーテルポリオール、及び市販のＰＰＧを用いた。ハロゲン含有ポリエーテルポリオールの性状は表１に示す。
Hereinafter, the present invention will be described with reference to Examples, but the present Examples do not limit the present invention in any way. The raw materials used in the following Examples and Comparative Examples and the evaluation method are as shown below.
<Polyprethane>
In Examples and Comparative Examples, a halogen-containing polyether polyol having a structure represented by the formula (1) and a commercially available PPG were used. The properties of the halogen-containing polyether polyol are shown in Table 1.
表１〜表３に記載の原料としてはそれぞれ以下のものを使用した。
＜＜ハロゲン含有ポリエーテルポリオール（Ａ）、（Ｂ）＞＞
テトラノルマルブチルアンモニウムブロミド（富士フイルム和光純薬工業社製）と、トリイソプロポキシアルミニウムを併用して脱水・脱溶媒を十分に行い、分子量４００のポリプロピレングリコール（三洋化成工業社製、商品名：サンニックスＰＰ−４００）に対して、１７．３ｍｏｌ当量のエピクロロヒドリン（富士フイルム和光純薬工業社製）を付加することで、分子量が２，０００で２官能のハロゲン含有ポリエーテルポリオール（Ａ）を作製した。
The following raw materials were used as the raw materials shown in Tables 1 to 3.
<< Halogen-containing polyether polyols (A), (B) >>
Tetraoctylammonyl ammonium bromide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and triisopropoxyaluminum are used in combination to sufficiently dehydrate and desolvate, and polypropylene glycol having a molecular weight of 400 (manufactured by Sanyo Kasei Kogyo Co., Ltd., trade name: Sun) By adding 17.3 mol equivalent of epichlorohydrin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) to Knicks PP-400), a bifunctional halogen-containing polyether polyol (A) having a molecular weight of 2,000 ) Was prepared.
さらに、ハロゲン含有ポリエーテルポリオール（Ａ）の作製において、１７．３ｍｏｌ当量のエピクロロヒドリンに代えて６．５ｍｏｌ当量のエピクロロヒドリンを付加する以外は同様にすることで、分子量が１，０００で２官能のハロゲン含有ポリエーテルポリオール（Ｂ）を作製した。
＜＜ハロゲン含有ポリエーテルポリオール（Ｃ）＞＞
テトラノルマルブチルアンモニウムブロミド（富士フイルム和光純薬工業社製）と、トリイソプロポキシアルミニウムを併用して脱水・脱溶媒を十分に行い、分子量６００のポリプロピレングリセリルエーテル（三洋化成工業社製、商品名：サンニックスＧＰ−６００）に対して、エピクロロヒドリン（富士フイルム和光純薬工業社製）を１５．１ｍｏｌ当量付加することで、分子量が２０００で３官能のハロゲン含有ポリエーテルポリオール（Ｃ）を作製した。
＜＜ハロゲン含有ポリエーテルポリオール（Ｄ）＞＞
ルイス酸触媒のＢＦ３−Ｅｔ２Ｏを用いて、分子量４００のポリプロピレングリコール（三洋化成工業社製、商品名：サンニックスＰＰ−４００）にエピクロロヒドリンを付加することで、分子量が２，０００で２官能のポリエーテルポリオール（Ｄ）を作製した。
＜＜市販のＰＰＧ＞＞
分子量２０００の汎用ＰＰＧ：旭硝子社製、商品名：エクセノール２０２０（官能基数：２、不飽和度：０．０３９ｍｅｑ／ｇ）
分子量５０００の高純度ＰＰＧ：旭硝子社製、商品名：プレミノールＳ３００６（官能基数：３、不飽和度：０．００６ｍｅｑ／ｇ）
＜ポリマーポリオール＞
いずれの実施例、比較例においても、三洋化成工業製のサンニックスＦＡ−７２８Ｒを使用した。
＜架橋剤＞
いずれの実施例、比較例においても、三井化学社製のアクトコールＫＬ−２１０を使用した。
＜発泡剤＞
いずれの実施例、比較例においても、発泡剤として、イオン交換水を使用した。
＜整泡剤＞
いずれの実施例、比較例においても、シリコーン系整泡剤として、東レ・ダウコーニング社製のＳＺ−１３２７を使用した。
＜連通化剤＞
いずれの実施例、比較例においても、連通化剤として、東邦化学工業社製トーホーポリオールＱＢ８０００を使用した。
＜触媒＞
いずれの実施例、比較例においても、触媒としてトリエチレンジアミンをジプロピレングリコールに３３重量％の濃度で溶かした溶液（東ソー社製、ＴＥＤＡ−Ｌ３３）とビス（２−ジメチルアミノエチル）エーテルをジプロピレングリコールに７０重量％の濃度で溶かした溶液（東ソー社製、ＴＯＹＯＣＡＴ−ＥＴ）を使用した。
＜難燃剤＞
比較例７において、ＩＣＬ−ＩＰ社製トリス（クロロプロピル）ホスフェート（商品名：ＦＹＲＯＬＰＣＦ）
＜イソシアネート化合物＞
いずれの実施例、比較例においても、トリレンジイソシアネート（ＴＤＩ）とポリフェニレンポリメチレンポリイソシアネートが８０重量％と２０重量％の比率となる混合物（東ソー社製、コロネート１０２１）を使用した。
（ポリオール性状の分析）
＜不飽和度＞
ＪＩＳ−Ｋ１５５７−６の方法に従い、測定した。
＜分子量分布（Ｍｗ／Ｍｎ）＞
ポリオール１０ｍｇとＴＨＦ１０ｍｌをサンプル瓶に添加し、１終夜静置することで溶解し、ＰＴＦＥカートリッジフィルター（０．５μｍ）でろ過することでサンプルを得た。
Further, in the preparation of the halogen-containing polyether polyol (A), the molecular weight is 1, except that 6.5 mol equivalent of epichlorohydrin is added instead of 17.3 mol equivalent of epichlorohydrin. A bifunctional halogen-containing polyether polyol (B) was prepared at 000.
<< Halogen-containing polyether polyol (C) >>
Tetranormal butylammonium bromide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and triisopropoxyaluminum are used in combination for sufficient dehydration and desolvation, and polypropylene glyceryl ether with a molecular weight of 600 (manufactured by Sanyo Kasei Kogyo Co., Ltd., trade name: By adding 15.1 mol equivalent of epichlorohydrin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) to Sanniks GP-600), a trifunctional halogen-containing polyether polyol (C) having a molecular weight of 2000 can be obtained. Made.
<< Halogen-containing polyether polyol (D) >>
By adding epichlorohydrin to polypropylene glycol having a molecular weight of 400 (manufactured by Sanyo Chemical Industries, Ltd., trade name: Sanniks PP-400) using a Lewis acid catalyst BF 3- Et 2 O, the molecular weight is 2, A bifunctional polyether polyol (D) was prepared at 000.
<< Commercially available PPG >>
General-purpose PPG with a molecular weight of 2000: manufactured by Asahi Glass Co., Ltd., trade name: Excelol 2020 (number of functional groups: 2, degree of unsaturation: 0.039 meq / g)
High-purity PPG with a molecular weight of 5000: manufactured by Asahi Glass Co., Ltd., trade name: Preminol S3006 (number of functional groups: 3, degree of unsaturation: 0.006 meq / g)
<Polymer polyol>
In all of the examples and comparative examples, Sanniks FA-728R manufactured by Sanyo Chemical Industries was used.
<Crosslinking agent>
In all of the examples and comparative examples, ACTCALL KL-210 manufactured by Mitsui Chemicals, Inc. was used.
<foaming agent>
In all of the examples and comparative examples, ion-exchanged water was used as the foaming agent.
<Foaming agent>
In each of the Examples and Comparative Examples, SZ-1327 manufactured by Toray Dow Corning Co., Ltd. was used as the silicone-based defoaming agent.
<Tonghua agent>
In each of the examples and comparative examples, Toho polyol QB8000 manufactured by Toho Chemical Industry Co., Ltd. was used as a communicating agent.
<Catalyst>
In each of the Examples and Comparative Examples, a solution (TEDA-L33 manufactured by Tosoh Corporation) in which triethylenediamine was dissolved in dipropylene glycol at a concentration of 33% by weight and bis (2-dimethylaminoethyl) ether were used as a catalyst. A solution (TOYOCAT-ET manufactured by Tosoh Corporation) dissolved in glycol at a concentration of 70% by weight was used.
<Flame retardant>
In Comparative Example 7, Tris (chloropropyl) phosphate manufactured by ICL-IP (trade name: FYROLPCF)
<Isocyanate compound>
In each of the Examples and Comparative Examples, a mixture (Coronate 1021 manufactured by Tosoh Corporation) in which toluene diisocyanate (TDI) and polyphenylene polymethylene polyisocyanate had a ratio of 80% by weight and 20% by weight was used.
(Analysis of polyol properties)
<Degree of unsaturation>
The measurement was performed according to the method of JIS-K1557-6.
<Molecular weight distribution (Mw / Mn)>
10 mg of polyol and 10 ml of THF were added to the sample bottle, dissolved by allowing to stand overnight, and filtered through a PTFE cartridge filter (0.5 μm) to obtain a sample.
検出器としてＲＩ検出器ＲＩ８０２０、測定用カラムとしてＴＳＫｇｅｌＧＭＲ−ＨＨＲＬ×２本直列、ＨＬＣ−８０２０ＧＰＣを用いた（いずれも東ソー社製）。 The RI detector RI8020 was used as the detector, and TSKgelGMR-HHRL × 2 in series and HLC-8020GPC were used as the measurement column (both manufactured by Tosoh Corporation).
測定条件としては、カラム温度４０℃、流速１．０ｍｌ／ｍｉｎ、溶媒ＴＨＦの条件で測定し、東ソー社製標準ポリスチレンを用いた３次近似曲線を検量線として、分子量分布（Ｍｗ／Ｍｎ）の解析を行った。 The measurement conditions were a column temperature of 40 ° C., a flow velocity of 1.0 ml / min, and a solvent THF. The molecular weight distribution (Mw / Mn) was measured using a cubic approximation curve using standard polystyrene manufactured by Tosoh Corporation as a calibration curve. The analysis was performed.
調整例（プレミックスの調整）
表１に示すハロゲン含有ポリエーテルポリオールと水を混合し、さらに、その混合物に、触媒、ポリマーポリオール、架橋剤、シリコーン系の整泡剤、連通化剤を混合し、それらの混合物を小型の高速撹拌機（プライミクス社製ＰＲＩＭＩＸ）を用いて毎分２０００回転で２０分間撹拌混合し、イソシアネート化合物を除く撹拌混合物（以下、プレミックスと記す）を得た。
Adjustment example (premix adjustment)
The halogen-containing polyether polyol shown in Table 1 and water are mixed, and further, a catalyst, a polymer polyol, a cross-linking agent, a silicone-based foam stabilizer, and a communicating agent are mixed in the mixture, and the mixture thereof is compact and high-speed. A stirring mixture (hereinafter referred to as premix) excluding the isocyanate compound was obtained by stirring and mixing at 2000 rpm for 20 minutes using a stirrer (PRIMIX manufactured by Primix).
表２に記載の所定の原材料を、所定量用いた以外は組成物１の調整例と同様の操作にて、プレミックス２〜７を作製した。 Premixes 2 to 7 were prepared in the same manner as in the preparation example of Composition 1 except that the predetermined raw materials shown in Table 2 were used in a predetermined amount.
（ポリウレタンフォームの評価方法）
＜ポリウレタンフォームの作製＞
調整例にて得られた組成物に、をイソシアネート基の全量（ＮＣＯ基）と水に含まれる水酸基（ＯＨ基）を含めて当該ＮＣＯ基と反応しうるイソシアネート基反応性基（ＮＣＯ反応性基）の比率、すなわちＮＣＯ／ＮＣＯ反応性基＝１．０となるようにイソシアネート化合物を加え、小型の高速撹拌機（プライミクス社製ＰＲＩＭＩＸ）を用いて毎分４０００回転で８秒間撹拌混合した後、上面開放型アルミ製モールドに直ちに注入し、発泡挙動を観察した。
＜成形性＞
ポリウレタンフォームの最大高さと、組成物とイソシアネート混合５分後の高さの比（落ち込み率）を算出し、成形性とした。
Ａ（成形性合格）：５％未満
Ｂ（成形性合格）：５％以上２５％未満
Ｃ（成形性不合格）：２５％以上
＜難燃性＞
作製したポリウレタンフォームを１２５ｍｍ×１３ｍｍ×１ｍｍの試験片とし、片側をクランプで垂直に固定し、２０秒間の接炎を２回行い、燃焼挙動を観察した。試験回数は５回とし、有炎燃焼時間の合計を算出し、合計有炎燃焼時間とした。
Ａ（難燃性合格）：合計有炎燃焼時間が２５０秒未満で、クランプまでの残炎無し
Ｂ（難燃性合格）：合計有炎燃焼時間が２５０秒以上で、クランプまでの残炎無し
Ｃ（難燃性不合格）：合計有炎燃焼時間が２５０秒以上で、クランプまでの残炎有り
実施例１〜３．
ポリウレタンフォームの評価方法に従い、プレミックス１〜３を用いてポリウレタンフォームを作製し、評価を行った。いずれのポリウレタンフォームも、成形性が良好で、難燃性に優れるものだった。
(Evaluation method of polyurethane foam)
<Making polyurethane foam>
Isocyanate group-reactive groups (NCO-reactive groups) capable of reacting with the NCO groups, including the total amount of isocyanate groups (NCO groups) and hydroxyl groups (OH groups) contained in water, in the composition obtained in the preparation example. ), That is, the isocyanate compound is added so that the NCO / NCO reactive group = 1.0, and the mixture is stirred and mixed at 4000 rpm for 8 seconds using a small high-speed stirrer (PRIMIX manufactured by Primix). It was immediately injected into an open-top aluminum mold and the foaming behavior was observed.
<Moldability>
The ratio of the maximum height of the polyurethane foam to the height after 5 minutes of mixing the composition with the isocyanate (fall rate) was calculated and used as the moldability.
A (passed moldability): less than 5% B (passed moldability): 5% or more and less than 25% C (failed moldability): 25% or more <flame retardant>
The produced polyurethane foam was used as a test piece of 125 mm × 13 mm × 1 mm, one side was vertically fixed with a clamp, and flame contact was performed twice for 20 seconds, and the combustion behavior was observed. The number of tests was 5, and the total flame burning time was calculated and used as the total flame burning time.
A (pass flame retardant): total flame burning time less than 250 seconds, no afterflame to clamp B (pass flame retardant): total flame burn time 250 seconds or more, no residual flame to clamp C (Flame-retardant failure): Total flame burning time is 250 seconds or more, and there is residual flame until the clamp. Examples 1 to 3.
According to the evaluation method of polyurethane foam, polyurethane foam was prepared using premixes 1 to 3 and evaluated. All of the polyurethane foams had good moldability and excellent flame retardancy.
比較例１．
ポリウレタンフォームの評価方法に従い、プレミックス４を用いてポリウレタンフォームを作製し、評価を行った。当該ポリウレタンフォームは、難燃性に優れたが、成形性に劣るものだった。
Comparative example 1.
According to the evaluation method of polyurethane foam, polyurethane foam was prepared using premix 4 and evaluated. The polyurethane foam was excellent in flame retardancy, but inferior in moldability.
比較例２．
ポリウレタンフォームの評価方法に従い、プレミックス５を用いてポリウレタンフォームを作製し、評価を行った。当該ポリウレタンフォームは、難燃性及び、成形性に劣るものだった。
Comparative example 2.
According to the evaluation method of polyurethane foam, polyurethane foam was prepared using Premix 5 and evaluated. The polyurethane foam was inferior in flame retardancy and moldability.
比較例３．
ポリウレタンフォームの評価方法に従い、プレミックス６を用いてポリウレタンフォームを作製し、評価を行った。当該ポリウレタンフォームは、難燃性に劣るものだった。
Comparative example 3.
According to the evaluation method of polyurethane foam, polyurethane foam was prepared using Premix 6 and evaluated. The polyurethane foam was inferior in flame retardancy.
比較例４．
リウレタンフォームの評価方法に従い、プレミックス７を用いてポリウレタンフォームを作製し、評価を行った。当該ポリウレタンフォームは、難燃性に優れたが、成形性に劣るものだった。
Comparative example 4.
A polyurethane foam was prepared using Premix 7 and evaluated according to the method for evaluating a polyurethane foam. The polyurethane foam was excellent in flame retardancy, but inferior in moldability.
上記実施例１〜３及び、比較例１〜４の結果を表３及び表４に併せて示す。 The results of Examples 1 to 3 and Comparative Examples 1 to 4 are shown in Tables 3 and 4.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019081770A JP2020180169A (en) | 2019-04-23 | 2019-04-23 | Polyurethane foam-forming composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019081770A JP2020180169A (en) | 2019-04-23 | 2019-04-23 | Polyurethane foam-forming composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2020180169A true JP2020180169A (en) | 2020-11-05 |
Family
ID=73023204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019081770A Pending JP2020180169A (en) | 2019-04-23 | 2019-04-23 | Polyurethane foam-forming composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2020180169A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115339183A (en) * | 2022-08-11 | 2022-11-15 | 千年舟新材科技集团股份有限公司 | Wood composite acoustic board with aldehyde-purifying and flame-retardant functions and preparation method thereof |
| WO2023074676A1 (en) * | 2021-11-01 | 2023-05-04 | 東ソー株式会社 | Polyol composition for polyurethane foam |
| WO2023145697A1 (en) * | 2022-01-28 | 2023-08-03 | 東ソー株式会社 | Chlorine-containing polyether polyol composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018123294A (en) * | 2017-01-27 | 2018-08-09 | 東ソー株式会社 | Halogen-containing polyether polyol and polyurethane comprising the same |
| JP2019081775A (en) * | 2007-09-14 | 2019-05-30 | ロート製薬株式会社 | Ophthalmic composition |
-
2019
- 2019-04-23 JP JP2019081770A patent/JP2020180169A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019081775A (en) * | 2007-09-14 | 2019-05-30 | ロート製薬株式会社 | Ophthalmic composition |
| JP2018123294A (en) * | 2017-01-27 | 2018-08-09 | 東ソー株式会社 | Halogen-containing polyether polyol and polyurethane comprising the same |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023074676A1 (en) * | 2021-11-01 | 2023-05-04 | 東ソー株式会社 | Polyol composition for polyurethane foam |
| WO2023145697A1 (en) * | 2022-01-28 | 2023-08-03 | 東ソー株式会社 | Chlorine-containing polyether polyol composition |
| CN115339183A (en) * | 2022-08-11 | 2022-11-15 | 千年舟新材科技集团股份有限公司 | Wood composite acoustic board with aldehyde-purifying and flame-retardant functions and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3046942B1 (en) | Polyurethane foam and associated method and article | |
| JP2016526585A (en) | Isocyanate / siloxane polyether composition | |
| CA2979277C (en) | Method of forming a polyurethane foam article | |
| CN113557255A (en) | Polyol blends and their use in the production of PUR-PIR foam-forming compositions | |
| JP2020180169A (en) | Polyurethane foam-forming composition | |
| CN102388081B (en) | Polyester polyols from terephthalic acid and oligoalkyl oxides | |
| JP2023027084A (en) | Hydrohaloolefin (hfo)-containing pu formulation | |
| JP2017171760A (en) | Composition for rigid polyurethane foam and manufacturing method of rigid polyurethane foam using the composition | |
| JP3948014B2 (en) | Method for producing rigid polyisocyanurate foam | |
| JP2012528894A (en) | Polyester polyols made from isophthalic acid and / or terephthalic acid and oligoalkylene oxide | |
| WO2022158396A1 (en) | Halogen-containing polyetherester polyol | |
| JP6997931B2 (en) | How to make polyisocyanurate hard foam | |
| JP2016501949A (en) | Flame retardant foam formulation | |
| WO2021215327A1 (en) | Halogen-containing polyether polyol | |
| KR20140026488A (en) | Process for producing rigid polyurethane foams | |
| JP6768631B2 (en) | Flame-retardant polyisocyanurate foam | |
| JP6815704B2 (en) | Flame-retardant thermosetting polyurethane foam | |
| JP7072345B2 (en) | Polyurethane foam-forming composition | |
| JP2020180170A (en) | Halogen-containing polyether polyol composition | |
| KR20200091451A (en) | Method for producing continuous foam rigid foam comprising urethane groups and isocyanurate groups | |
| JP2003292560A (en) | Method for producing hard polyurethane foam | |
| WO2023074676A1 (en) | Polyol composition for polyurethane foam | |
| US20240279379A1 (en) | Open cell flexible isocyanate-based foams having a low exotherm during foaming | |
| JP2024140463A (en) | Polyurethane foam-forming composition, polyurethane foam, and method for producing polyurethane foam | |
| JP2023038106A (en) | Composition for polyurethane foam and use thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220321 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20230123 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230207 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230328 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20230425 |