JP2006265553A - ポリ(エーテル−エステル)ポリオール及びその製造方法 - Google Patents
ポリ(エーテル−エステル)ポリオール及びその製造方法 Download PDFInfo
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- JP2006265553A JP2006265553A JP2006073018A JP2006073018A JP2006265553A JP 2006265553 A JP2006265553 A JP 2006265553A JP 2006073018 A JP2006073018 A JP 2006073018A JP 2006073018 A JP2006073018 A JP 2006073018A JP 2006265553 A JP2006265553 A JP 2006265553A
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- Prior art keywords
- ester
- acid
- ether
- poly
- product
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- 229920005862 polyol Polymers 0.000 title claims abstract description 58
- 150000003077 polyols Chemical class 0.000 title claims abstract description 58
- 229920001693 poly(ether-ester) Polymers 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 36
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 34
- -1 dicarboxylic acid ester Chemical class 0.000 claims abstract description 32
- 125000004185 ester group Chemical group 0.000 claims abstract description 12
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 7
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 229920000570 polyether Polymers 0.000 claims description 34
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 238000005809 transesterification reaction Methods 0.000 claims description 27
- 150000002009 diols Chemical class 0.000 claims description 24
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 229920001228 polyisocyanate Polymers 0.000 claims description 2
- 239000005056 polyisocyanate Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 9
- 230000001105 regulatory effect Effects 0.000 abstract description 3
- 125000000962 organic group Chemical group 0.000 abstract 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 42
- 239000000047 product Substances 0.000 description 39
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 239000007858 starting material Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 4
- AFENDNXGAFYKQO-VKHMYHEASA-N (S)-2-hydroxybutyric acid Chemical compound CC[C@H](O)C(O)=O AFENDNXGAFYKQO-VKHMYHEASA-N 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 4
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 229960002510 mandelic acid Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 4
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 4
- 229960003656 ricinoleic acid Drugs 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 description 3
- MGMNPSAERQZUIM-UHFFFAOYSA-N 2-(hydroxymethyl)benzoic acid Chemical class OCC1=CC=CC=C1C(O)=O MGMNPSAERQZUIM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 238000007259 addition reaction Methods 0.000 description 3
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- 150000002596 lactones Chemical class 0.000 description 3
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- 238000010626 work up procedure Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
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- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical class OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
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- 239000002841 Lewis acid Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 2
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- 229930006000 Sucrose Natural products 0.000 description 2
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- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 239000005720 sucrose Substances 0.000 description 2
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- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- BRRSNXCXLSVPFC-UHFFFAOYSA-N 2,3,4-Trihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1O BRRSNXCXLSVPFC-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 238000012369 In process control Methods 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
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- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
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- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- MNUOZFHYBCRUOD-UHFFFAOYSA-N hydroxyphthalic acid Natural products OC(=O)C1=CC=CC(O)=C1C(O)=O MNUOZFHYBCRUOD-UHFFFAOYSA-N 0.000 description 1
- 238000010965 in-process control Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920006030 multiblock copolymer Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
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- 238000007127 saponification reaction Methods 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000012974 tin catalyst Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000008096 xylene Substances 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
- C08G18/48—Polyethers
- C08G18/4887—Polyethers containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03B—INSTALLATIONS OR METHODS FOR OBTAINING, COLLECTING, OR DISTRIBUTING WATER
- E03B7/00—Water main or service pipe systems
- E03B7/07—Arrangement of devices, e.g. filters, flow controls, measuring devices, siphons or valves, in the pipe systems
- E03B7/078—Combined units with different devices; Arrangement of different devices with respect to each other
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03B—INSTALLATIONS OR METHODS FOR OBTAINING, COLLECTING, OR DISTRIBUTING WATER
- E03B7/00—Water main or service pipe systems
- E03B7/07—Arrangement of devices, e.g. filters, flow controls, measuring devices, siphons or valves, in the pipe systems
- E03B7/074—Arrangement of water treatment devices
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03B—INSTALLATIONS OR METHODS FOR OBTAINING, COLLECTING, OR DISTRIBUTING WATER
- E03B7/00—Water main or service pipe systems
- E03B7/09—Component parts or accessories
- E03B7/10—Devices preventing bursting of pipes by freezing
- E03B7/12—Devices preventing bursting of pipes by freezing by preventing freezing
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Public Health (AREA)
- Water Supply & Treatment (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
本発明の方法は、下記工程を含んでなる。
(1)a)1 個以上のヒドロキシル基を含み、一般式:
を有する 1 種以上のモノカルボン酸エステル又はポリカルボン酸エステルと
b)1 種以上のアルキレンオキシドとを、
開環を伴って反応させて、対応する 1 個以上の結合ポリエーテル鎖を含むモノカルボン酸エステル又はポリカルボン酸エステルを得(アルキレンオキシド付加は、任意に
c)1 種以上のジオール及び/又はポリオール
及び任意に
d)1 種以上のジカルボン酸エステル
の存在下で行われる。)、
次いで、
(2)工程(1)で製造された生成物を下記工程の 1 つによって更に反応させる:
(i)工程(1)の生成物をエステル交換してヒドロキシル官能性ポリ(エーテル-エステル)を生ずる(エステル交換は、任意に
(a)1 種以上のジオール及び/又はポリオール、
又は任意に
(b)1 種以上のジオール、及びジカルボン酸又はジカルボン酸誘導体、
又は任意に
(c)1 種以上のジオール又はポリオール、及び 1 個以上のヒドロキシル基を含むモノカルボン酸エステル又はモノカルボン酸
の添加を伴って行われる);
(ii)工程(1)の生成物を、
(a)添加した、遊離ヒドロキシル基を含み得るモノカルボン酸エステル及び/又はポリカルボン酸エステル
によりエステル交換して、末端エステル基含有ポリ(エーテル-エステル)を生ずる;
又は
(iii)工程(1)の生成物を鹸化(即ち、加水分解)して対応する結合ポリ(エーテル)鎖を含むモノカルボン酸又はポリカルボン酸を生じ、これら酸を
(a)遊離ヒドロキシル基を含み得るモノカルボン酸及び/又はポリカルボン酸
の任意添加を伴ってエステル化して、末端カルボン酸基含有ポリ(エーテル-エステル)を生ずる。
実施例において、下記成分を使用した。
ポリオール A:プロピレングリコールへのプロピレンオキシド付加によって製造された、OH 価 260 の二官能性ポリエーテル
ポリオール B:グリセロールへのプロピレンオキシド付加によって製造された、OH 価 238 の三官能性ポリエーテル
DMC 触媒:米国特許第 5,482,908 号明細書及び同第 5,536,883 号明細書(欧州特許公開第 700 949 号公報に対応)に記載されているように製造された、ヘキサシアノコバルト酸亜鉛、t-ブタノール及び 1000 g/mol の数平均分子量を有するポリプロピレングリコールを含む複金属シアン化物触媒
0.105 g の DMC 触媒を、2 リットル容の加圧型オートクレーブ内の 333.1 g の p-ヒドロキシ安息香酸エチルエステルに添加した。雰囲気酸素を、排気と窒素供給を繰り返すことによって除去した。プロピレンオキシド添加開始時の反応器圧力は 0.1 bar であり、撹拌機速度は 800 rpm に設定し、反応温度は 130 ℃であった。下記のように、合計で 682 g のプロピレンオキシドを添加した。まず、132 g のプロピレンオキシドを、2 時間にわたって 3 等分して添加した。更に 20 g のプロピレンオキシドを添加した後、反応が開始したが、これは反応器内圧力の急激な低下によって示された。残りのプロピレンオキシドを 2 時間かけて添加した。プロピレンオキシドの添加完了後、反応器内の圧力が 0.8 bar の一定値になるまで、反応を継続した。次いで、生成物を 90 ℃、20 mbar で 30 分間加熱し、追加の後処理なしで更に反応させた。
得られた生成物の OH 価:105.5 mgKOH/g
得られた生成物の 25 ℃での粘度:225 mPas
247 g のポリオール A を、989 g の実施例 1 の生成物に添加した。100 mg のチタン酸 t-ブチルエステルの添加後、まず窒素雰囲気中で、次いで減圧下(1 mbar)で、撹拌しながら混合物を 200 ℃に加熱した。85 g のエタノールを留去した後、反応を終了した。
得られた生成物の OH 価:57.6 mgKOH/g
得られた生成物の 25 ℃での粘度:9360 mPas
0.3 g の DMC 触媒を、10 リットル容の加圧型オートクレーブ内の、840.4 g のポリオール B 及び 592.4 g の 4-ヒドロキシ安息香酸エチルエステルに添加した。反応器内容物を、減圧下、撹拌しながら(800 rpm)80 ℃で 53 分間加熱した。プロピレンオキシドの添加開始時、反応器圧力は 0.2 bar であり、反応の撹拌速度は 800 rpm で維持し、反応温度は 130 ℃であった。合計で 567.23 g のプロピレンオキシドを、一定速度で 2.67 時間にわたって添加した。189 g のプロピレンオキシドを添加した後、反応開始が反応器内圧力の急激な低下によって示された(到達した最大圧力:1.35 bar)。プロピレンオキシドの添加完了後、0.4 bar の一定圧力に達するまで、反応を 130 ℃で継続した。90 ℃に冷却後、反応器内容物を 20 mbar で 30 分間加熱した。次いで、オートクレーブを窒素での加圧によって常圧にし、内容物を 50 ℃に冷却した。OH 価及び粘度を測定するため、プロポキシレートの試料を取り出した。
得られた生成物の OH 価:196.15 mgKOH/g
得られた生成物の 25 ℃での粘度:301 mPas
この生成物に、197.7 mg のチタン酸 t-ブチルエステルを添加した。混合物を、まずは常圧で、次いで減圧下(1 mbar)で 200 ℃に加熱した。160 g のエタノールを留去した後、反応を終了した。
得られた生成物の OH 価:106.7 mgKOH/g
得られた生成物の 25 ℃での粘度:20,900 mPas
313 mg の DMC 触媒を、10 リットル容の加圧型オートクレーブ内の、568.2 g のポリオール B、400.5 g の 4-ヒドロキシ安息香酸エチルエステル及び 275 mg の 85 %リン酸に添加した。反応器内容物を、減圧下、撹拌しながら(800 rpm)80 ℃で 5 時間加熱した。窒素導入によって圧力を 1.5 bar に増加させ、206.55 g のプロピレンオキシドを、140 ℃で 1.43 時間かけて撹拌しながら(800 rpm)添加した。130 g のプロピレンオキシドを添加した後、反応開始が反応器内圧力の急激な低下によって示された(到達した最大圧力:3.2 bar)。プロピレンオキシドの添加直後、826.4 g のエチレンオキシドを、140 ℃で 2.13 時間かけて撹拌しながら(800 rpm)添加した。1.9 bar の一定最終圧力に達するまで、反応を 140 ℃で継続した。90 ℃に冷却後、反応器内容物を 20 mbar で 30 分間加熱した。次いで、オートクレーブを窒素での加圧によって常圧にし、内容物を 50 ℃に冷却した。OH 価及び粘度を測定するため、アルキレンオキシド付加生成物の試料を取り出した。
得られた生成物の OH 価:134.4 mgKOH/g
得られた生成物の 25 ℃での粘度:491 mPas
生成物中の一級 OH 基含有量:77 %
その後、183.1 mg のチタン酸 t-ブチルエステルを添加した。混合物を、まずは常圧で、次いで減圧下(1 mbar)で 200 ℃に加熱した。107.7 g のエタノールを留去した後、反応を終了した。
得られた生成物の OH 価:73.0 mgKOH/g
得られた生成物の 50 ℃での粘度:679 mPas
生成物中の一級 OH 基含有量:74 %
Claims (3)
- (1)a)1 個以上のヒドロキシル基を含み、一般式:
を有する 1 種以上のモノカルボン酸エステル又はポリカルボン酸エステルと
b)アルキレンオキシドとを、
任意に
c)1 種以上のジオール及び/又はポリオール
及び任意に
d)1 種以上のジカルボン酸エステル
の存在下で、開環を伴って反応させて、対応する 1 個以上の結合ポリエーテル鎖を含むモノカルボン酸エステル又はポリカルボン酸エステルを得、
(2)工程(1)で製造された生成物を下記工程によって更に反応させる:
(i)工程(1)の生成物をエステル交換して OH-官能性ポリ(エーテル-エステル)を生ずる(エステル交換は、任意に
(a)更なるジオール又はポリオール、
又は任意に
(b)更なるジオール、及びジカルボン酸又はジカルボン酸誘導体、
又は任意に
(c)更なるジオール又はポリオール、及び 1 個以上のヒドロキシル基を含むモノカルボン酸エステル又はモノカルボン酸
の添加を伴って行われる);
(ii)工程(1)の生成物を、
(a)添加した、遊離ヒドロキシル基を含み得るモノカルボン酸エステル又はポリカルボン酸エステル
によりエステル交換して、末端エステル基含有ポリ(エーテル-エステル)を生ずる;
又は
(iii)工程(1)の生成物を加水分解して対応する結合ポリ(エーテル)鎖を含むモノカルボン酸又はポリカルボン酸を生じ、これらを
(a)遊離ヒドロキシル基を含み得るモノカルボン酸又はポリカルボン酸
の任意添加を伴ってエステル化して、末端カルボン酸基含有ポリ(エーテル-エステル)を生ずる
ことを含んでなる、ポリ(エーテル-エステル)の製造方法。 - 請求項1に記載の方法によって製造されたポリ(エーテル-エステル)。
- ポリイソシアネート成分とイソシアネート反応性成分との反応を含んでなるポリウレタンの製造方法であって、イソシアネート反応性成分が請求項2に記載のポリ(エーテル-エステル)を含む方法。
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EP2350191B1 (en) * | 2008-11-14 | 2013-09-11 | Dow Global Technologies LLC | Modified natural oils and products made therefrom |
US8901187B1 (en) | 2008-12-19 | 2014-12-02 | Hickory Springs Manufacturing Company | High resilience flexible polyurethane foam using MDI |
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- 2006-03-17 KR KR1020060024698A patent/KR101325855B1/ko not_active IP Right Cessation
- 2006-03-20 CN CNA2006100682294A patent/CN1847284A/zh active Pending
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EP1702941A1 (de) | 2006-09-20 |
ES2309847T3 (es) | 2008-12-16 |
ATE401360T1 (de) | 2008-08-15 |
US20070155941A1 (en) | 2007-07-05 |
SG126086A1 (en) | 2006-10-30 |
US20060211830A1 (en) | 2006-09-21 |
US7687599B2 (en) | 2010-03-30 |
US20100137552A1 (en) | 2010-06-03 |
CA2539365A1 (en) | 2006-09-19 |
US7893189B2 (en) | 2011-02-22 |
DE502006001091D1 (de) | 2008-08-28 |
KR20060101344A (ko) | 2006-09-22 |
CN1847284A (zh) | 2006-10-18 |
EP1702941B1 (de) | 2008-07-16 |
BRPI0601020A (pt) | 2007-05-15 |
SG160421A1 (en) | 2010-04-29 |
JP5153078B2 (ja) | 2013-02-27 |
KR101325855B1 (ko) | 2013-11-05 |
DE102005012794A1 (de) | 2006-09-21 |
MXPA06002932A (es) | 2006-09-18 |
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