JP2011529997A - 芳香族ポリエステル、それを含むポリオールブレンド、及びそれから得られる製品 - Google Patents
芳香族ポリエステル、それを含むポリオールブレンド、及びそれから得られる製品 Download PDFInfo
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- JP2011529997A JP2011529997A JP2011521565A JP2011521565A JP2011529997A JP 2011529997 A JP2011529997 A JP 2011529997A JP 2011521565 A JP2011521565 A JP 2011521565A JP 2011521565 A JP2011521565 A JP 2011521565A JP 2011529997 A JP2011529997 A JP 2011529997A
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- Prior art keywords
- polyol
- polyester
- aromatic
- glycol
- weight percent
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- 229920005862 polyol Polymers 0.000 title claims abstract description 98
- 150000003077 polyols Chemical class 0.000 title claims abstract description 98
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 title claims description 78
- 229920000728 polyester Polymers 0.000 title claims description 46
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 57
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 56
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 49
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 18
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 17
- 238000009472 formulation Methods 0.000 claims description 36
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 30
- 239000006260 foam Substances 0.000 claims description 22
- 239000012948 isocyanate Substances 0.000 claims description 22
- 150000002513 isocyanates Chemical class 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- -1 oxyalkylene glycol Chemical compound 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 13
- 229920001228 polyisocyanate Polymers 0.000 claims description 13
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 12
- 229920001971 elastomer Polymers 0.000 claims description 10
- 239000000806 elastomer Substances 0.000 claims description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 abstract description 24
- 239000004814 polyurethane Substances 0.000 abstract description 24
- 239000000463 material Substances 0.000 abstract description 17
- 239000011495 polyisocyanurate Substances 0.000 abstract description 10
- 229920000582 polyisocyanurate Polymers 0.000 abstract description 10
- 238000002156 mixing Methods 0.000 abstract description 4
- 239000000376 reactant Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 10
- 239000004604 Blowing Agent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004970 Chain extender Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 150000002334 glycols Chemical class 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229920013701 VORANOL™ Polymers 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004606 Fillers/Extenders Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-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
- 229920013708 Dow VORANOL™ CP 1421 Polyol Polymers 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- DUFKCOQISQKSAV-UHFFFAOYSA-N Polypropylene glycol (m w 1,200-3,000) Chemical compound CC(O)COC(C)CO DUFKCOQISQKSAV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
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- 239000010695 polyglycol Substances 0.000 description 2
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- 239000000565 sealant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011493 spray foam Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- MURCRDIZBLOGAE-UHFFFAOYSA-N 1,3-ditert-butylcyclohexa-3,5-diene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)(C(C)(C)C)C1O MURCRDIZBLOGAE-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-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
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- 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
- 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 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-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
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- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- BTQLWKNIJDKIAB-UHFFFAOYSA-N 6-methylidene-n-phenylcyclohexa-2,4-dien-1-amine Chemical compound C=C1C=CC=CC1NC1=CC=CC=C1 BTQLWKNIJDKIAB-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
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- WMTLVUCMBWBYSO-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 WMTLVUCMBWBYSO-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
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- 229920000388 Polyphosphate Polymers 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
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- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
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- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000004067 bulking agent 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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
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- LAGWVZPUXSKERV-UHFFFAOYSA-N cyclohexane;isocyanic acid Chemical compound N=C=O.C1CCCCC1 LAGWVZPUXSKERV-UHFFFAOYSA-N 0.000 description 1
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000002937 thermal insulation foam Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- LVPSBELIABHESA-UHFFFAOYSA-L zinc;n,n-dibutylcarbamothioate Chemical compound [Zn+2].CCCCN(C([O-])=S)CCCC.CCCCN(C([O-])=S)CCCC LVPSBELIABHESA-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
- C08G18/4213—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from terephthalic acid and dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
- C08G18/4252—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids derived from polyols containing polyether groups and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
Abstract
Description
A)テレフタル酸80モルパーセント以上を含む芳香族成分、
B)分子量150から1000を有するポリエチレングリコール、及び
C)B)のグリコールとは異なるグリコールの反応生成物を含み、
A、B、及びCが、重量パーセントベースで、A)20から60重量パーセント、B)40から75重量パーセント、及びC)0から40重量パーセントで反応に存在する、ポリエステルポリオールを提供する。
1)A)テレフタル酸80モルパーセント以上を含む芳香族成分、
B)分子量150から1000を有するポリエチレングリコール、及び
C)B)のグリコールとは異なるグリコール、
(A、B、及びCは、重量パーセントベースで、A)20から60重量パーセント、B)40から75重量パーセント、及びC)0から40重量パーセントで反応に存在する)の反応生成物であるポリオール、
2)ポリイソシアナート、並びに
3)場合により、それ自体公知である添加剤及び助剤を含む、ポリオール組成物を含む硬質フォームを生成するための反応系を提供する。そのような任意の添加剤又は助剤は、染料、顔料、内部離型剤、物理的発泡剤、化学的発泡剤、難燃剤、増量剤、強化剤、可塑剤、防煙剤、香料、帯電防止剤、殺生物剤、抗酸化剤、光安定剤、接着促進剤、及びこれらの組み合わせからなる群より選択される。
式中、Rは、水素、又は1から4個の炭素原子の低級アルキルであり、nは、1から5であり、ただしR部分の少なくとも10パーセントは低級アルキル基である。さらなる実施形態において、nは4以下である。さらなる実施形態において、nは3以下である。別の実施形態において、すべてのR部分は、低級アルキルである。さらなる実施形態において、Rはメチル基である。そのようなアルキレングリコールの例には、プロピレングリコール及びジ−プロピレングリコールが含まれる。さらなる実施形態において、グリコール成分C)は、全体の平均分子量180以下を有する。3官能性グリコールの例には、グリセリン及びトリメチロールプロパンが含まれる。
ジエチレングリコール(289.5g)、ポリエチレングリコール200(1800g)、及びテレフタル酸(910.5g)を、窒素導入管、空気圧攪拌機、温度計、及びコンデンサを備えた5000mlガラス製フラスコに充填する。加熱し、フラスコの内容物を230〜235℃に上昇させる。温度220℃で、チタンアセチルアセトナート触媒(Du PontのTyzor AA−105)(0.15g)を充填し、少量の窒素流を適用する。混合物を230〜235℃で5時間保つ。この時点でポリエステルポリオールは、酸価0.5mgKOH/g未満を有する。フラスコの内容物を大気条件下、室温に冷却する。
ポリエステル1に関して記載した器具に、ジエチレングリコール(1820g)及びテレフタル酸(1680g)を添加する。対照ポリエステルを生成する方法は、ポリエステル1の生成に関して示したとおりである。
上記のとおり調製したポリエステル1を、高圧機械(Cannon A40)を用いて、不連続パネルの硬質ポリイソシアヌラート断熱材を調製する配合物に用いる。対照配合物は、Terate 4026ポリエステルポリオール(Invista)、ヒドロキシル価約205及び粘度約2500mPa*s@25℃を有する芳香族ポリエステルポリオールを用いる。配合ポリオールを表1に示す。
ポリエステル1を、表5に示すとおり、エラストマーを生成するための配合物に用いる。エラストマーを生成する場合、一般に、高温での変形/応力を回避するために、最終エラストマーが高いTgを有することが好ましい。比較例は、芳香族ポリエステルStepanpol PS3152を用いる。
Claims (18)
- A)テレフタル酸80モルパーセント以上を含む芳香族成分、
B)分子量150から1000を有するポリエチレングリコール、及び
C)B)のグリコールとは異なるグリコールの反応生成物を含み、
A、B、及びCが、重量パーセントベースで、A)20から60重量パーセント、B)40から75重量パーセント、及びC)0から40重量パーセントで反応に存在するポリエステルポリオール。 - 前記芳香族含有成分が、テレフタル酸85モルパーセント以上を含む、請求項1に記載のポリオール。
- 前記芳香族含有成分が、テレフタル酸95モルパーセント以上を含む、請求項2に記載のポリオール。
- ポリエチレングリコールが、分子量500未満を有する、請求項1から3のいずれか一項に記載のポリオール。
- 成分C)が、反応混合物の1から30重量パーセント未満の量で存在する、請求項4に記載のポリオール。
- 成分Cが、エチレングリコール又はジエチレングリコールである、請求項6に記載のポリオール。
- UNI EN ISO 3219によって測定された25℃での粘度2500mPa*s未満、及びヒドロキシル価200から400を有する、芳香族ポリエステルポリオール。
- 前記ポリオールが、粘度2000mPa*s以下を有する、請求項8に記載のポリエステル。
- 前記ポリエステルの芳香族含有量の80モルパーセント以上が、テレフタル酸に由来する、請求項9に記載のポリエステル。
- 請求項1から7のいずれか一項に記載のポリオール10から90重量パーセントを含み、残部は少なくとも1種の第2ポリオールであり、前記第2ポリオールは、官能価2から8及び分子量100から10000を有するモノール又はポリエーテルポリオールである、ポリオール組成物。
- 前記第2ポリオールが、官能価2から6及びヒドロキシル価200から1200を有する少なくとも1種のポリオールを含有する、請求項11に記載のポリオール組成物。
- ポリオール配合物における粘度低下添加剤としての、請求項1から7のいずれか一項に記載の芳香族ポリエステルポリオールの使用。
- 硬質フォームを製造するためのポリオール配合物における、請求項1から7のいずれか一項に記載の芳香族ポリエステルポリオールの使用。
- 前記配合物が、硬質フォームを生成するためのスプレー配合物である、請求項14に記載の使用。
- エラストマーを製造するための配合物における、請求項1から7のいずれか一項に記載の芳香族ポリエステルポリオールの使用。
- 請求項12に記載のポリオール組成物及びポリイソシアナートを含む硬質フォームを生成するための反応系。
- 前記イソシアナートが、ジフェニルメタン−4,4’−ジイソシアナート系列のものである、請求項17に記載の反応系。
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IT001480A ITMI20081480A1 (it) | 2008-08-06 | 2008-08-06 | Poliesteri aromatici, miscele palioliche che li comprendono e prodotti risultanti |
PCT/EP2009/060123 WO2010015642A1 (en) | 2008-08-06 | 2009-08-04 | Aromatic polyesters, polyol blends comprising the same and resultant products therefrom |
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2009
- 2009-08-04 RU RU2011108556/04A patent/RU2503690C2/ru active
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- 2009-08-04 PL PL09804567T patent/PL2313449T3/pl unknown
- 2009-08-04 ES ES09804567.7T patent/ES2674257T3/es active Active
- 2009-08-04 EP EP09804567.7A patent/EP2313449B1/en active Active
- 2009-08-04 WO PCT/EP2009/060123 patent/WO2010015642A1/en active Application Filing
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- 2009-08-04 MX MX2011001389A patent/MX2011001389A/es active IP Right Grant
- 2009-08-04 US US13/056,671 patent/US20110133122A1/en not_active Abandoned
- 2009-08-04 JP JP2011521565A patent/JP5663478B2/ja active Active
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JP2014502651A (ja) * | 2010-12-21 | 2014-02-03 | ダウ グローバル テクノロジーズ エルエルシー | 硬質ポリウレタンフォームの改善された低温スキン硬化のためのポリオール配合物 |
JP2015520260A (ja) * | 2012-05-25 | 2015-07-16 | ダウ グローバル テクノロジーズ エルエルシー | ポリイソシアヌレート発泡体パネルの生成 |
Also Published As
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RU2011108556A (ru) | 2012-09-20 |
MX2011001389A (es) | 2011-07-20 |
CN102159613B (zh) | 2014-08-27 |
EP2313449B1 (en) | 2018-05-02 |
US20130289151A1 (en) | 2013-10-31 |
BRPI0912463B1 (pt) | 2019-10-01 |
BRPI0912463A2 (pt) | 2018-12-11 |
US20110133122A1 (en) | 2011-06-09 |
ITMI20081480A1 (it) | 2010-02-06 |
ES2674257T3 (es) | 2018-06-28 |
CN102159613A (zh) | 2011-08-17 |
TR201810716T4 (tr) | 2018-08-27 |
RU2503690C2 (ru) | 2014-01-10 |
US8912245B2 (en) | 2014-12-16 |
EP2313449A1 (en) | 2011-04-27 |
PL2313449T3 (pl) | 2018-09-28 |
JP5663478B2 (ja) | 2015-02-04 |
WO2010015642A1 (en) | 2010-02-11 |
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