JP5217425B2

JP5217425B2 - 熱可塑性樹脂組成物、その製造方法およびそれからなる成形品

熱可塑性樹脂組成物、その製造方法およびそれからなる成形品 Download PDF

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Publication number: JP5217425B2
Authority: JP; Japan
Prior art keywords: compound; poly; thermoplastic resin; acid; group
Prior art date: 2007-12-26
Legal status : Expired - Fee Related

Application number

JP2007335402A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009155479A (ja

JP2009155479A5 (enrdf_load_stackoverflow

Inventor

貞紀熊澤

陽介尾上

裕千大目

Current Assignee

Toray Industries Inc

Original Assignee

Toray Industries Inc

Priority date

2007-12-26

Filing date

2007-12-26

Publication date

2013-06-19

2007-12-26 Application filed by Toray Industries Inc filed Critical Toray Industries Inc

2007-12-26 Priority to JP2007335402A priority Critical patent/JP5217425B2/ja

2009-07-16 Publication of JP2009155479A publication Critical patent/JP2009155479A/ja

2011-02-10 Publication of JP2009155479A5 publication Critical patent/JP2009155479A5/ja

2013-06-19 Application granted granted Critical

2013-06-19 Publication of JP5217425B2 publication Critical patent/JP5217425B2/ja

Status Expired - Fee Related legal-status Critical Current

2027-12-26 Anticipated expiration legal-status Critical

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229920005992 thermoplastic resin Polymers 0.000 title claims description 104
239000011342 resin composition Substances 0.000 title claims description 48
238000004519 manufacturing process Methods 0.000 title claims description 39
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125000000524 functional group Chemical group 0.000 claims description 176
150000001875 compounds Chemical class 0.000 claims description 147
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 58
239000004645 polyester resin Substances 0.000 claims description 31
229920001225 polyester resin Polymers 0.000 claims description 29
229920005989 resin Polymers 0.000 claims description 27
239000011347 resin Substances 0.000 claims description 27
238000002156 mixing Methods 0.000 claims description 25
239000003795 chemical substances by application Substances 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
239000011256 inorganic filler Substances 0.000 claims description 17
229910003475 inorganic filler Inorganic materials 0.000 claims description 17
239000002981 blocking agent Substances 0.000 claims description 14
239000007809 chemical reaction catalyst Substances 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
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125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004018 acid anhydride group Chemical group 0.000 claims description 5
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 description 91
229920000642 polymer Polymers 0.000 description 48
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 43
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 34
230000007062 hydrolysis Effects 0.000 description 32
238000006460 hydrolysis reaction Methods 0.000 description 31
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 30
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 21
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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 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
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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 18
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125000003277 amino group Chemical group 0.000 description 15
125000003118 aryl group Chemical group 0.000 description 15
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 14
238000006116 polymerization reaction Methods 0.000 description 14
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 14
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OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 13
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WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
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239000002904 solvent Substances 0.000 description 12
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229910019142 PO4 Inorganic materials 0.000 description 11
235000021317 phosphate Nutrition 0.000 description 11
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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 10
125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 10
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 10
UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 10
JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
230000009477 glass transition Effects 0.000 description 10
QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 10
239000010452 phosphate Substances 0.000 description 10
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 10
238000011156 evaluation Methods 0.000 description 9
229920000058 polyacrylate Polymers 0.000 description 9
229920002302 Nylon 6,6 Polymers 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
239000007983 Tris buffer Substances 0.000 description 8
RPHKINMPYFJSCF-UHFFFAOYSA-N benzene-1,3,5-triamine Chemical compound NC1=CC(N)=CC(N)=C1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
UYAUGHKQCCCFDK-UHFFFAOYSA-N cyclohexane-1,3,5-triamine Chemical compound NC1CC(N)CC(N)C1 UYAUGHKQCCCFDK-UHFFFAOYSA-N 0.000 description 8
150000002009 diols Chemical class 0.000 description 8
238000002347 injection Methods 0.000 description 8
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125000000896 monocarboxylic acid group Chemical group 0.000 description 8
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
229920001451 polypropylene glycol Polymers 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
239000003484 crystal nucleating agent Substances 0.000 description 7
235000014113 dietary fatty acids Nutrition 0.000 description 7
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229910052751 metal Inorganic materials 0.000 description 7
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229920000515 polycarbonate Polymers 0.000 description 7
239000004417 polycarbonate Substances 0.000 description 7
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 7
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
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FTHDNRBKSLBLDA-UHFFFAOYSA-N cyclohexane-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)CC(C(O)=O)C1 FTHDNRBKSLBLDA-UHFFFAOYSA-N 0.000 description 6
229940105990 diglycerin Drugs 0.000 description 6
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QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
230000007774 longterm Effects 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
125000005487 naphthalate group Chemical group 0.000 description 6
229920000647 polyepoxide Polymers 0.000 description 6
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LQGXMVHKZWQXKT-UHFFFAOYSA-N 2-methylpropane-1,2,3-triamine Chemical compound NCC(N)(C)CN LQGXMVHKZWQXKT-UHFFFAOYSA-N 0.000 description 5
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ZLVNIVAOTHPXFV-UHFFFAOYSA-N cyclohexane-1,2,4-triamine Chemical compound NC1CCC(N)C(N)C1 ZLVNIVAOTHPXFV-UHFFFAOYSA-N 0.000 description 5
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XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
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PZZICILSCNDOKK-UHFFFAOYSA-N propane-1,2,3-triamine Chemical compound NCC(N)CN PZZICILSCNDOKK-UHFFFAOYSA-N 0.000 description 5
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239000011593 sulfur Substances 0.000 description 5
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SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 description 4
KODVEKZCSDEPTL-UHFFFAOYSA-N butane-1,2,4-triamine Chemical compound NCCC(N)CN KODVEKZCSDEPTL-UHFFFAOYSA-N 0.000 description 4
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 4
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239000012986 chain transfer agent Substances 0.000 description 4
NCQXZCNJWTXVDX-UHFFFAOYSA-N cyclohexane-1,2,4,5-tetramine Chemical compound NC1CC(N)C(N)CC1N NCQXZCNJWTXVDX-UHFFFAOYSA-N 0.000 description 4
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
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ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
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BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
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230000003287 optical effect Effects 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
239000003505 polymerization initiator Substances 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 4
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 4
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GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 3
LPIQIQPLUVLISR-UHFFFAOYSA-N 2-prop-1-en-2-yl-4,5-dihydro-1,3-oxazole Chemical compound CC(=C)C1=NCCO1 LPIQIQPLUVLISR-UHFFFAOYSA-N 0.000 description 3
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
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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
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DOOPOMANTWCTIB-UHFFFAOYSA-M tris(2-methylpropyl)stannanylium;acetate Chemical compound CC([O-])=O.CC(C)C[Sn+](CC(C)C)CC(C)C DOOPOMANTWCTIB-UHFFFAOYSA-M 0.000 description 1
UNTJEZNVLMAXQI-UHFFFAOYSA-N tris(oxiran-2-ylmethyl) benzene-1,3,5-tricarboxylate Chemical compound C=1C(C(=O)OCC2OC2)=CC(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 UNTJEZNVLMAXQI-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
NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-UHFFFAOYSA-N 0.000 description 1
BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
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CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
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PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1