JP4925557B2 - Polyester resin composition - Google Patents
Polyester resin composition Download PDFInfo
- Publication number
- JP4925557B2 JP4925557B2 JP2003370237A JP2003370237A JP4925557B2 JP 4925557 B2 JP4925557 B2 JP 4925557B2 JP 2003370237 A JP2003370237 A JP 2003370237A JP 2003370237 A JP2003370237 A JP 2003370237A JP 4925557 B2 JP4925557 B2 JP 4925557B2
- Authority
- JP
- Japan
- Prior art keywords
- tert
- polyester resin
- butyl
- bis
- hydroxy
- 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.)
- Expired - Fee Related
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- 229920001225 polyester resin Polymers 0.000 title claims description 29
- 239000004645 polyester resin Substances 0.000 title claims description 29
- 239000000203 mixture Substances 0.000 title claims description 15
- -1 polyethylene terephthalate Polymers 0.000 claims description 44
- 239000003963 antioxidant agent Substances 0.000 claims description 18
- 230000003078 antioxidant effect Effects 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 4
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 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 3
- 230000000694 effects Effects 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-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
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 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 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000001261 hydroxy acids Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-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
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 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 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- QGMCRJZYVLHHHB-UHFFFAOYSA-N (1,2,2,6,6-pentamethylpiperidin-4-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 QGMCRJZYVLHHHB-UHFFFAOYSA-N 0.000 description 1
- UDZNBVQPXCTQBH-UHFFFAOYSA-N (1-dihydroxyphosphanylbiphenylen-2-yl)phosphonous acid Chemical compound C1=CC=C2C3=C(P(O)O)C(P(O)O)=CC=C3C2=C1 UDZNBVQPXCTQBH-UHFFFAOYSA-N 0.000 description 1
- JMUOXOJMXILBTE-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 JMUOXOJMXILBTE-UHFFFAOYSA-N 0.000 description 1
- HZVFRKSYUGFFEJ-YVECIDJPSA-N (2r,3r,4s,5r)-7-phenylhept-6-ene-1,2,3,4,5,6-hexol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=CC1=CC=CC=C1 HZVFRKSYUGFFEJ-YVECIDJPSA-N 0.000 description 1
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- WTJWFFXZUSGGKB-UHFFFAOYSA-N (4-octoxyphenyl)-phenylmethanone Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 WTJWFFXZUSGGKB-UHFFFAOYSA-N 0.000 description 1
- MYMRQBXYZBKPAE-UHFFFAOYSA-N (6,6-dihydroxycyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical class OC1(O)C=CC=CC1C(=O)C1=CC=CC=C1 MYMRQBXYZBKPAE-UHFFFAOYSA-N 0.000 description 1
- VKLDCBNUFZIAFK-UHFFFAOYSA-N 1,1-bis[2,4-bis(2-phenylpropan-2-yl)phenyl]-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C1=CC=CC=C1)C(C)(C)C1=CC=CC=C1 VKLDCBNUFZIAFK-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- MYMKXVFDVQUQLG-UHFFFAOYSA-N 1,3,7,9-tetratert-butyl-11-fluoro-5-methyl-5h-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound CC1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP(F)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C MYMKXVFDVQUQLG-UHFFFAOYSA-N 0.000 description 1
- SVNVBMPPWVBFTL-UHFFFAOYSA-N 1,4-bis(2,2,6,6-tetramethylpiperidin-4-yl)-2,3-di(tridecyl)butane-1,2,3,4-tetracarboxylic acid Chemical compound CCCCCCCCCCCCCC(C(C1CC(NC(C1)(C)C)(C)C)C(=O)O)(C(=O)O)C(CCCCCCCCCCCCC)(C(C2CC(NC(C2)(C)C)(C)C)C(=O)O)C(=O)O SVNVBMPPWVBFTL-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
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 1
- WLJWKXUQFXBFRX-UHFFFAOYSA-N 2,3,4-tributyl-5-methylphenol Chemical compound C(CCC)C1=C(C(=C(C=C1C)O)CCCC)CCCC WLJWKXUQFXBFRX-UHFFFAOYSA-N 0.000 description 1
- KMSQABAABGSUTH-UHFFFAOYSA-N 2,3-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=C(O)C=CC(C(O)=O)=C1C(C)(C)C KMSQABAABGSUTH-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- SIYKRXXNGPOWCQ-UHFFFAOYSA-N 2,4-bis(2,4-ditert-butylphenyl)-1,3,5-triazine Chemical compound C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C1=NC=NC(=N1)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C SIYKRXXNGPOWCQ-UHFFFAOYSA-N 0.000 description 1
- DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 1
- UUINYPIVWRZHAG-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 UUINYPIVWRZHAG-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- ROHFBIREHKPELA-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid;methane Chemical compound C.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O ROHFBIREHKPELA-UHFFFAOYSA-N 0.000 description 1
- ZSMMOCNTIRCAAL-UHFFFAOYSA-N 2-[2-[2-[2-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 2-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound C=1C(C)=C(O)C(C(C)(C)C)=CC=1C(C)C(=O)OCCOCCOCCOC(=O)C(C)C1=CC(C)=C(O)C(C(C)(C)C)=C1 ZSMMOCNTIRCAAL-UHFFFAOYSA-N 0.000 description 1
- LUNZMFXLUXABFZ-UHFFFAOYSA-N 2-[4,6-bis(2,4-ditert-butylphenyl)-1,3,5-triazin-2-yl]-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(=CC=2)C(C)(C)C)C(C)(C)C)=NC(C=2C(=CC(=CC=2)C(C)(C)C)C(C)(C)C)=N1 LUNZMFXLUXABFZ-UHFFFAOYSA-N 0.000 description 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
- NMAGCVWUISAHAP-UHFFFAOYSA-N 3,5-ditert-butyl-2-(2,4-ditert-butylphenyl)-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1C1=C(C(O)=O)C=C(C(C)(C)C)C(O)=C1C(C)(C)C NMAGCVWUISAHAP-UHFFFAOYSA-N 0.000 description 1
- WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 description 1
- BYRKZZJQBLXWPY-UHFFFAOYSA-N 3-(3-dodecanoyloxy-3-oxopropyl)sulfanylpropanoyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCSCCC(=O)OC(=O)CCCCCCCCCCC BYRKZZJQBLXWPY-UHFFFAOYSA-N 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- HPFWYRKGZUGGPB-UHFFFAOYSA-N 4,6-dichloro-n-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 HPFWYRKGZUGGPB-UHFFFAOYSA-N 0.000 description 1
- UQAMDAUJTXFNAD-UHFFFAOYSA-N 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine Chemical compound ClC1=NC(Cl)=NC(N2CCOCC2)=N1 UQAMDAUJTXFNAD-UHFFFAOYSA-N 0.000 description 1
- STEYNUVPFMIUOY-UHFFFAOYSA-N 4-Hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CC(O)CC(C)(C)N1CCO STEYNUVPFMIUOY-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- JJHKARPEMHIIQC-UHFFFAOYSA-N 4-octadecoxy-2,6-diphenylphenol Chemical compound C=1C(OCCCCCCCCCCCCCCCCCC)=CC(C=2C=CC=CC=2)=C(O)C=1C1=CC=CC=C1 JJHKARPEMHIIQC-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- QCBBOXGEDQONFF-UHFFFAOYSA-N 5-oxo-5-tridecoxypentane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCOC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O QCBBOXGEDQONFF-UHFFFAOYSA-N 0.000 description 1
- OWXXKGVQBCBSFJ-UHFFFAOYSA-N 6-n-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[2-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]ami Chemical compound N=1C(NCCCN(CCN(CCCNC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC(N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 OWXXKGVQBCBSFJ-UHFFFAOYSA-N 0.000 description 1
- HNKNVHRXMLUJGX-UHFFFAOYSA-N 6-n-[3-[[4,6-bis[butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[2-[[4,6-bis[butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[3-[[4,6-bis[butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]amino]pro Chemical compound N=1C(NCCCN(CCN(CCCNC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)=NC(N(CCCC)C2CC(C)(C)NC(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)NC(C)(C)C1 HNKNVHRXMLUJGX-UHFFFAOYSA-N 0.000 description 1
- BJMZKHIKOPPZAM-UHFFFAOYSA-N 6-n-[6,11-bis[[4,6-bis[butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]amino]undecyl]-2-n,4-n-dibutyl-2-n,4-n-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound N=1C(NCCCCCC(CCCCCNC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)NC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)N(CCCC)C2CC(C)(C)NC(C)(C)C2)=NC(N(CCCC)C2CC(C)(C)NC(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)NC(C)(C)C1 BJMZKHIKOPPZAM-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- QGWAYNUBVXRMEQ-UHFFFAOYSA-N CC1=C(C=C(C(=C1)O)C(C)(C)C)C(CC(C)C1=C(C=C(C(=C1)C(C)(C)C)O)C)C1=C(C=C(C(=C1)C(C)(C)C)O)C.C(C)(C1=C(C(=CC(=C1)C(C)CC)C(C)(C)C)O)C1=C(C(=CC(=C1)C(C)CC)C(C)(C)C)O Chemical compound CC1=C(C=C(C(=C1)O)C(C)(C)C)C(CC(C)C1=C(C=C(C(=C1)C(C)(C)C)O)C)C1=C(C=C(C(=C1)C(C)(C)C)O)C.C(C)(C1=C(C(=CC(=C1)C(C)CC)C(C)(C)C)O)C1=C(C(=CC(=C1)C(C)CC)C(C)(C)C)O QGWAYNUBVXRMEQ-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
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- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- IORUEKDKNHHQAL-UHFFFAOYSA-N [2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenyl] prop-2-enoate Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)OC(=O)C=C)=C1O IORUEKDKNHHQAL-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- DCBNMBIOGUANTC-UHFFFAOYSA-N [5-[(5-benzoyl-4-hydroxy-2-methoxyphenyl)methyl]-2-hydroxy-4-methoxyphenyl]-phenylmethanone Chemical compound COC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1CC(C(=CC=1O)OC)=CC=1C(=O)C1=CC=CC=C1 DCBNMBIOGUANTC-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 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
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZCGNNESZWJPBLW-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite 2-[2-(2-hydroxyphenyl)propan-2-yl]-3,4,5,6-tetra(tridecyl)phenol Chemical compound OP(O)OP(O)O.CCCCCCCCCCCCCC1=C(CCCCCCCCCCCCC)C(CCCCCCCCCCCCC)=C(O)C(C(C)(C)C=2C(=CC=CC=2)O)=C1CCCCCCCCCCCCC ZCGNNESZWJPBLW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- IAJNXBNRYMEYAZ-UHFFFAOYSA-N ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC)C1=CC=CC=C1 IAJNXBNRYMEYAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- CSWFWSPPZMEYAY-UHFFFAOYSA-N octadecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(O)O CSWFWSPPZMEYAY-UHFFFAOYSA-N 0.000 description 1
- AXRSHKZFNKUGQB-UHFFFAOYSA-N octyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC)OC1=CC=CC=C1 AXRSHKZFNKUGQB-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- JDKSZLFJOLSRHU-UHFFFAOYSA-N tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,1,1,2-tetracarboxylate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(CC)C(=O)OC1CC(C)(C)N(C)C(C)(C)C1 JDKSZLFJOLSRHU-UHFFFAOYSA-N 0.000 description 1
- NYKHQQHUHLNYLW-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,1,1,2-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(CC)C(=O)OC1CC(C)(C)NC(C)(C)C1 NYKHQQHUHLNYLW-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は、特定の構造を有するベンゾトリアゾール化合物とリン系酸化防止剤を添加したポリエステル樹脂組成物に関し、より詳細には、特定の構造を有するベンゾトリアゾール化合物を多量に配合したポリエステル樹脂マスターバッチであって、マスターバッチ製造時にリン系酸化防止剤を添加することにより乾燥時の着色が抑制されたポリエステル樹脂組成物に関する。 The present invention relates to a polyester resin composition to which a benzotriazole compound having a specific structure and a phosphorus-based antioxidant are added. More specifically, the present invention relates to a polyester resin master batch containing a large amount of a benzotriazole compound having a specific structure. In addition, the present invention relates to a polyester resin composition in which coloring during drying is suppressed by adding a phosphorus-based antioxidant during the production of a masterbatch.
従来から、ポリエチレンテレフタレートなどのポリエステル樹脂は、繊維、フィルム、ボトルなどに広く用いられてきた。 Conventionally, polyester resins such as polyethylene terephthalate have been widely used for fibers, films, bottles and the like.
これらポリエステル樹脂は、光により劣化することや、ボトルなどの容器に用いた場合に、内容物の光により変色して商品性を損なうため、紫外線吸収剤の添加が一般的に行われている。 These polyester resins are generally added with an ultraviolet absorber because they deteriorate due to light, or when used in a container such as a bottle, the color of the contents changes to impair the merchantability.
一方、紫外線吸収剤などの安定化剤を樹脂へ配合する方法として、樹脂へ均一分散させるために予めマスターバッチとして高濃度で添加した樹脂を未安定化樹脂へ添加して安定化する方法が広く知られている。 On the other hand, as a method of blending a stabilizer such as an ultraviolet absorber into a resin, there is a wide range of methods in which a resin previously added at a high concentration as a masterbatch is added to an unstabilized resin for uniform dispersion in the resin. Are known.
紫外線吸収剤の中で、２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールは特開昭６１−１１８３７３号公報に提案された優れた紫外線吸収剤であり、特開昭６１−１１３６４９号公報、特開昭６１−１１３６６７号公報、特開昭６１−１６３９５４号公報、特開昭６２−２２５５５４号公報、特開昭６２−１４６９５１号公報、特開昭６２−１７２０５８号公報、特開昭６３−１０６５３号公報などに種々の樹脂に対する利用が提案されている。 Among the ultraviolet absorbers, 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol is an excellent ultraviolet absorber proposed in Japanese Patent Application Laid-Open No. 61-118373. Japanese Unexamined Patent Publication Nos. 61-1113649, 61-1313667, 61-163954, 62-225554, 62-146951, 62-172058. No. 6, Japanese Patent Laid-Open No. 63-10653, etc. propose use for various resins.
しかし、２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールをポリエステル樹脂のマスターバッチとした場合、ポリエステル樹脂の乾燥工程において著しく着色するという問題があった。
ポリエステル樹脂の乾燥工程は、加水分解を防止する上で不可欠な工程であり、２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールは耐光性や耐抽出性に優れた紫外線吸収剤であり、本発明は２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールを配合したポリエステル樹脂のマスターバッチの乾燥工程における着色防止を防止するものである。 The drying process of the polyester resin is an indispensable process for preventing hydrolysis, and 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol is excellent in light resistance and extraction resistance. The present invention is to prevent coloration in the drying process of a masterbatch of a polyester resin blended with 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol. is there.
本発明者らは、上記の現状に鑑み鋭意検討を重ねた結果、ポリエステル樹脂に２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールとリン系酸化防止剤を添加することにより、着色性に優れたポリエステル樹脂組成物を提供できることを見出した。 As a result of intensive studies in view of the above situation, the present inventors have added 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol and a phosphorus-based antioxidant to the polyester resin. By doing this, it discovered that the polyester resin composition excellent in coloring property can be provided.
即ち、本発明の第一は、ポリエステル樹脂１００重量部に対して、下記一般式（Ｉ）で表わされる化合物（Ａ）とリン系酸化防止剤（Ｂ）を（Ａ）／（Ｂ）＝９９／１〜５０／５０（重量比）の範囲で、かつ両者の合計で５〜５０重量部を配合したポリエステル樹脂組成物からなるマスターバッチを提供する。
本発明の第三は、リン系酸化防止剤（Ｂ）が一般式（ＩＩ）で表される化合物である本発明の第一又は第二のマスターバッチを提供する。
3rd of this invention provides the 1st or 2nd masterbatch of this invention whose phosphorus antioxidant (B) is a compound represented by general formula (II).
本発明により、乾燥工程における着色が少ない高濃度に２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールが配合されたポリエステル樹脂組成物を提供できる。 According to the present invention, it is possible to provide a polyester resin composition in which 2,2'-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol is blended at a high concentration with little coloring in the drying step.
以下に本発明を詳細に説明する。 The present invention is described in detail below.
本発明に用いられるポリエステル樹脂としては、二塩基酸とジヒドロキシ化合物の構造を主成分に有するもの、またはこれらに加えてもしくは単独でヒドロキシ酸の構造を主成分もしくは副成分に有するポリエステルであり、二塩基酸としては、テレフタル酸、イソフタル酸などのフタル酸類、ナフタレンジカルボン酸、ビフェニルジカルボン酸などの芳香族二塩基酸；アジピン酸、マレイン酸、フマル酸などの脂肪族二塩基酸が挙げられる。ジヒドロキシ化合物としてはエチレングリコール、プロピレングリコール、１，３−トリメチレングリコール、１，２−ブタンジオール、１，３−ブタンジオール、１，４−ブタンジオール、ネオペンチルグリコール、１，６−ヘキサンジオール、シクロヘキサンジメタノール、シクロヘキサンジオールなどの脂肪族グリコール；ハイドロキノン、レゾルシノール、ビスフェノールA、ビスフェノールFなどの芳香族ジヒドロキシ化合物などが挙げられる。ヒドロキシ酸またはその構造を与えるものとしては、乳酸、グリコール酸、ヒドロキシビバリン酸、ヒドロキシカプロン酸などの脂肪族ヒドロキシ酸、その誘導体であるε−カプロラクトン等のラクトン、ｐ−ヒドロキシ安息香酸、ヒドロキシフェニル酢酸、ナフチルグリコール酸などの芳香族ヒドロキシ酸が挙げられる。
なお、トリメリット酸、ピロメリット酸、ブタンテトラカルボン酸などの多塩基酸やグリセリン、トリメチロールプロパン、ペンタエリスリトールなどの多価アルコールを架橋剤として配合してもよい。
The polyester resin used in the present invention is a polyester resin having a structure of a dibasic acid and a dihydroxy compound as a main component, or a polyester having a hydroxy acid structure as a main component or a subcomponent in addition to or alone. Examples of the basic acid include phthalic acids such as terephthalic acid and isophthalic acid, aromatic dibasic acids such as naphthalenedicarboxylic acid and biphenyldicarboxylic acid; and aliphatic dibasic acids such as adipic acid, maleic acid and fumaric acid. Dihydroxy compounds include ethylene glycol, propylene glycol, 1,3-trimethylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, Aliphatic glycols such as cyclohexanedimethanol and cyclohexanediol; aromatic dihydroxy compounds such as hydroquinone, resorcinol, bisphenol A, and bisphenol F. Examples of the hydroxy acid or its structure are aliphatic acid such as lactic acid, glycolic acid, hydroxybivalic acid and hydroxycaproic acid, lactone such as ε-caprolactone which is a derivative thereof, p-hydroxybenzoic acid, hydroxyphenyl Aromatic hydroxy acids such as acetic acid and naphthyl glycolic acid can be mentioned.
In addition, you may mix | blend polybasic acids, such as trimellitic acid, pyromellitic acid, butanetetracarboxylic acid, and polyhydric alcohols, such as glycerol, a trimethylol propane, and a pentaerythritol, as a crosslinking agent.
上記ポリエステル樹脂としては、分子量、分子量分布、重合触媒などは特に限定されず、分子量や分子量分布は加工条件や用途により適宜選択され、重合触媒は飲料ボトルなど食品と接触する用途にはゲルマニウムを触媒としたものが衛生上好ましい。 The molecular weight, molecular weight distribution, polymerization catalyst and the like are not particularly limited as the polyester resin, and the molecular weight and molecular weight distribution are appropriately selected according to processing conditions and applications. The polymerization catalyst is a catalyst for germanium for applications such as beverage bottles that come into contact with food. These are preferred for hygiene purposes.
本発明に用いられるリン系酸化防止剤としては、トリスノニルフェニルホスファイト、トリス（２，４−ジ第三ブチルフェニル）ホスファイト、トリス〔２−第三ブチル−４−（３−第三ブチル−４−ヒドロキシ−５−メチルフェニルチオ）−５−メチルフェニル〕ホスファイト、トリデシルホスファイト、オクチルジフェニルホスファイト、ジ（デシル）モノフェニルホスファイト、ジ（トリデシル）ペンタエリスリトールジホスファイト、ジ（ノニルフェニル）ペンタエリスリトールジホスファイト、ビス（２，４−ジ第三ブチルフェニル）ペンタエリスリトールジホスファイト、ビス（２，６−ジ第三ブチル−４−メチルフェニル）ペンタエリスリトールジホスファイト、ビス（２，４，６−トリ第三ブチルフェニル）ペンタエリスリトールジホスファイト、ビス（２，４−ジクミルフェニル）ペンタエリスリトールジホスファイト、テトラ（トリデシル）イソプロピリデンジフェノールジホスファイト、テトラ（トリデシル）−４，４’−n−ブチリデンビス（２−第三ブチル−５−メチルフェノール）ジホスファイト、ヘキサ（トリデシル）−１，１，３−トリス（２−メチル−４−ヒドロキシ−５−第三ブチルフェニル）ブタントリホスファイト、テトラキス（２，４−ジ第三ブチルフェニル）ビフェニレンジホスホナイト、９，１０−ジハイドロ−９−オキサ−１０−ホスファフェナンスレン−１０−オキサイド、２，２’−メチレンビス（４，６−第三ブチルフェニル）−２−エチルヘキシルホスファイト、２，２’−メチレンビス（４，６−第三ブチルフェニル）−オクタデシルホスファイト、２，２’−エチリデンビス（４，６−ジ第三ブチルフェニル）フルオロホスファイト、トリス（２−〔（２，４，８，１０−テトラキス第三ブチルジベンゾ〔ｄ，ｆ〕〔１，３，２〕ジオキサホスフェピン−６−イル）オキシ〕エチル）アミン、２−エチル−２−ブチルプロピレングリコールと２，４，６−トリ第三ブチルフェノールのホスファイトなどが挙げられる。 Examples of the phosphorus-based antioxidant used in the present invention include trisnonylphenyl phosphite, tris (2,4-ditertiarybutylphenyl) phosphite, tris [2-tertiarybutyl-4- (3-tertiarybutyl). -4-hydroxy-5-methylphenylthio) -5-methylphenyl] phosphite, tridecyl phosphite, octyl diphenyl phosphite, di (decyl) monophenyl phosphite, di (tridecyl) pentaerythritol diphosphite, di (Nonylphenyl) pentaerythritol diphosphite, bis (2,4-ditert-butylphenyl) pentaerythritol diphosphite, bis (2,6-ditert-butyl-4-methylphenyl) pentaerythritol diphosphite, Bis (2,4,6-tritert-butylphenyl) pentaerythri Diphosphite, bis (2,4-dicumylphenyl) pentaerythritol diphosphite, tetra (tridecyl) isopropylidenediphenol diphosphite, tetra (tridecyl) -4,4′-n-butylidenebis (2-secondary) Tributyl-5-methylphenol) diphosphite, hexa (tridecyl) -1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butanetriphosphite, tetrakis (2,4-diter Tributylphenyl) biphenylenediphosphonite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2′-methylenebis (4,6-tert-butylphenyl) -2- Ethylhexyl phosphite, 2,2'-methylenebis (4,6-tert-butylphenyl) Octadecyl phosphite, 2,2′-ethylidenebis (4,6-ditert-butylphenyl) fluorophosphite, tris (2-[(2,4,8,10-tetrakis tert-butyldibenzo [d, f] [1,3,2] dioxaphosphin-6-yl) oxy] ethyl) amine, phosphite of 2-ethyl-2-butylpropylene glycol and 2,4,6-tritert-butylphenol .
上記リン系酸化防止剤としては、前記一般式（II）で表される化合物が着色防止効果が大きく好ましい。また、リン系酸化防止剤の配合量は、２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノール／リン系酸化防止剤（重量比）で９９／１〜５０／５０、好ましくは９５／５〜７５／２５の範囲であり、ポリエステル樹脂１００重量部に対して２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールとの合計量で５〜５０重量部、好ましくは１０〜３０重量部になるように用いられる。２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールとの比で９９／１より少ないと十分な着色防止効果が得られず、５０／５０より多く用いても着色防止効果はほとんど向上せず経済的に不利になる。樹脂への配合量は、５重量部未満ではマスターバッチとして未安定化樹脂へ配合する場合に使用量が多くなりすぎて効率が悪く、５０重量部より多く用いると得られる樹脂組成物のペレット等の表面に２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールやリン系酸化防止剤が吹き出して、組成が均一に保てなくなりやすいので好ましくない。 As said phosphorus antioxidant, the compound represented by the said general formula (II) has a large coloring prevention effect, and is preferable. Moreover, the compounding quantity of phosphorus antioxidant is 99 / 1-50 / 2,2'-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol / phosphorus antioxidant (weight ratio). 50, preferably in the range of 95/5 to 75/25, with a total amount of 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol per 100 parts by weight of the polyester resin. 5 to 50 parts by weight, preferably 10 to 30 parts by weight. If the ratio to 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol is less than 99/1, a sufficient anti-coloring effect cannot be obtained, and even if it is used more than 50/50, it will be colored. The prevention effect is hardly improved and it becomes economically disadvantageous. If the amount of resin is less than 5 parts by weight, the amount used is too high when blended into an unstabilized resin as a masterbatch, resulting in poor efficiency. Since 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol and phosphorus antioxidant blow out on the surface of the film, the composition tends to be difficult to keep uniform.
本発明のポリエステル樹脂組成物は、必要に応じてフェノール系酸化防止剤、ヒンダードアミン系安定剤、２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノール以外の紫外線吸収剤などを添加することが好ましい。 The polyester resin composition of the present invention contains UV absorbers other than phenolic antioxidants, hindered amine stabilizers, and 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol as necessary. Etc. are preferably added.
上記フェノール系酸化防止剤としては、２，６−ジ第三ブチル−ｐ−クレゾール、２，６−ジフェニル−４−オクタデシロキシフェノール、ジステアリル（３，５−ジ第三ブチル−４−ヒドロキシベンジル）ホスホネート、１，６−ヘキサメチレンビス〔（３，５−ジ第三ブチル−４−ヒドロキシフェニル）プロピオン酸アミド〕、４，４’−チオビス（６−第三ブチル−ｍ−クレゾール）、２，２’−メチレンビス（４−メチル−６−第三ブチルフェノール）、２，２’−メチレンビス（４−エチル−６−第三ブチルフェノール）、４，４’−ブチリデンビス（６−第三ブチル−ｍ−クレゾール）、２，２’−エチリデンビス（４，６−ジ第三ブチルフェノール）、２，２’−エチリデンビス（４−第二ブチル−６−第三ブチルフェノール）、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−第三ブチルフェニル）ブタン、１，３，５−トリス（２，６−ジメチル−３−ヒドロキシ−４−第三ブチルベンジル）イソシアヌレート、１，３，５−トリス（３，５−ジ第三ブチル−４−ヒドロキシベンジル）イソシアヌレート、１，３，５−トリス（３，５−ジ第三ブチル−４−ヒドロキシベンジル）−２，４，６−トリメチルベンゼン、２−第三ブチル−４−メチル−６−（２−アクリロイルオキシ−３−第三ブチル−５−メチルベンジル）フェノール、ステアリル（３，５−ジ第三ブチル−４−ヒドロキシフェニル）プロピオネート、チオジエチレングリコールビス〔（３，５−ジ第三ブチル−４−ヒドロキシフェニル）プロピオネート〕、１，６−ヘキサメチレンビス〔（３，５−ジ第三ブチル−４−ヒドロキシフェニル）プロピオネート〕、ビス〔３，３−ビス（４−ヒドロキシ−３−第三ブチルフェニル）ブチリックアシッド〕グリコールエステル、ビス〔２−第三ブチル−４−メチル−６−（２−ヒドロキシ−３−第三ブチル−５−メチルベンジル）フェニル〕テレフタレート、１，３，５−トリス〔（３，５−ジ第三ブチル−４−ヒドロキシフェニル）プロピオニルオキシエチル〕イソシアヌレート、テトラキス〔メチレン−３−（３，５−ジ第三ブチル−４−ヒドロキシフェニル）プロピオネート〕メタン、３，９−ビス〔１，１−ジメチル−２−｛（３−第三ブチル−４−ヒドロキシ−５−メチルフェニル）プロピオニルオキシ｝エチル〕−２，４，８，１０−テトラオキサスピロ〔５．５〕ウンデカン、トリエチレングリコールビス〔（３−第三ブチル−４−ヒドロキシ−５−メチルフェニル）プロピオネート〕などが挙げられ、樹脂１００重量部に対して、０．００１〜１０重量部、より好ましくは、０．０５〜５重量部が用いられる。なお、これらの配合量割合は、以下のヒンダードアミン系安定剤、紫外線吸収剤においても同様である。 Examples of the phenolic antioxidant include 2,6-ditert-butyl-p-cresol, 2,6-diphenyl-4-octadecyloxyphenol, distearyl (3,5-ditert-butyl-4-hydroxy). Benzyl) phosphonate, 1,6-hexamethylenebis [(3,5-ditert-butyl-4-hydroxyphenyl) propionic acid amide], 4,4′-thiobis (6-tert-butyl-m-cresol), 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 2,2'-methylenebis (4-ethyl-6-tert-butylphenol), 4,4'-butylidenebis (6-tert-butyl-m -Cresol), 2,2'-ethylidenebis (4,6-ditert-butylphenol), 2,2'-ethylidenebis (4-secondarybutyl-6-tert-butylphenol) 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, 1,3,5-tris (2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl) ) Isocyanurate, 1,3,5-tris (3,5-ditert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (3,5-ditert-butyl-4-hydroxybenzyl) ) -2,4,6-trimethylbenzene, 2-tert-butyl-4-methyl-6- (2-acryloyloxy-3-tert-butyl-5-methylbenzyl) phenol, stearyl (3,5-ditert Tributyl-4-hydroxyphenyl) propionate, thiodiethylene glycol bis [(3,5-ditert-butyl-4-hydroxyphenyl) propionate], 1,6-hexamethylene bis (3,5-ditert-butyl-4-hydroxyphenyl) propionate], bis [3,3-bis (4-hydroxy-3-tert-butylphenyl) butyric acid] glycol ester, bis [2-tertiary] Butyl-4-methyl-6- (2-hydroxy-3-tert-butyl-5-methylbenzyl) phenyl] terephthalate, 1,3,5-tris [(3,5-ditert-butyl-4-hydroxyphenyl) ) Propionyloxyethyl] isocyanurate, tetrakis [methylene-3- (3,5-ditert-butyl-4-hydroxyphenyl) propionate] methane, 3,9-bis [1,1-dimethyl-2-{(3 -Tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy} ethyl] -2,4,8,10-tetraoxaspiro [5.5] un Decane, triethylene glycol bis [(3-tert-butyl-4-hydroxy-5-methylphenyl) propionate] and the like, 0.001 to 10 parts by weight, more preferably 0.05-5 parts by weight are used. In addition, these compounding quantity ratios are the same also in the following hindered amine stabilizers and ultraviolet absorbers.
上記ヒンダードアミン系安定剤としては、２，２，６，６−テトラメチル−４−ピペリジルステアレート、１，２，２，６，６−ペンタメチル−４−ピペリジルステアレート、２，２，６，６−テトラメチル−４−ピペリジルベンゾエート、ビス（２，２，６，６−テトラメチル−４−ピペリジル）セバケート、ビス（１，２，２，６，６−ペンタメチル−４−ピペリジル）セバケート、テトラキス（２，２，６，６−テトラメチル−４−ピペリジル）ブタンテトラカルボキシレート、テトラキス（１，２，２，６，６−ペンタメチル−４−ピペリジル）ブタンテトラカルボキシレート、ビス（２，２，６，６−テトラメチル−４−ピペリジル）・ジ（トリデシル）−１，２，３，４−ブタンテトラカルボキシレート、ビス（１，２，２，６，６−ペンタメチル−４−ピペリジル）・ジ（トリデシル）−１，２，３，４−ブタンテトラカルボキシレート、ビス（１，２，２，６，６−ペンタメチル−４−ピペリジル）−２−ブチル−２−（３，５−ジ第三ブチル−４−ヒドロキシベンジル）マロネート、１−（２−ヒドロキシエチル）−２，２，６，６−テトラメチル−４−ピペリジノール／コハク酸ジエチル重縮合物、１，６−ビス（２，２，６，６−テトラメチル−４−ピペリジルアミノ）ヘキサン／ジブロモエタン重縮合物、１，６−ビス（２，２，６，６−テトラメチル−４−ピペリジルアミノ）ヘキサン／２，４−ジクロロ−６−モルホリノ−ｓ−トリアジン重縮合物、１，６−ビス（２，２，６，６−テトラメチル−４−ピペリジルアミノ）ヘキサン／２，４−ジクロロ−６−第三オクチルアミノ−ｓ−トリアジン重縮合物、１，５，８，１２−テトラキス〔２，４−ビス（Ｎ−ブチル−Ｎ−（２，２，６，６−テトラメチル−４−ピペリジル）アミノ）−ｓ−トリアジン−６−イル〕−１，５，８，１２−テトラアザドデカン、１，５，８，１２−テトラキス〔２，４−ビス（Ｎ−ブチル−Ｎ−（１，２，２，６，６−ペンタメチル−４−ピペリジル）アミノ）−ｓ−トリアジン−６−イル〕−１，５，８，１２−テトラアザドデカン、１，６，１１−トリス〔２，４−ビス（Ｎ−ブチル−Ｎ−（２，２，６，６−テトラメチル−４−ピペリジル）アミノ）−ｓ−トリアジン−６−イルアミノ〕ウンデカン、１，６，１１−トリス〔２，４−ビス（Ｎ−ブチル−Ｎ−（１，２，２，６，６−ペンタメチル−４−ピペリジル）アミノ）−ｓ−トリアジン−６−イルアミノ〕ウンデカン等のヒンダードアミン化合物が挙げられる。 Examples of the hindered amine stabilizer include 2,2,6,6-tetramethyl-4-piperidyl stearate, 1,2,2,6,6-pentamethyl-4-piperidyl stearate, 2,2,6,6. -Tetramethyl-4-piperidylbenzoate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, tetrakis ( 2,2,6,6-tetramethyl-4-piperidyl) butanetetracarboxylate, tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) butanetetracarboxylate, bis (2,2,6 , 6-tetramethyl-4-piperidyl) -di (tridecyl) -1,2,3,4-butanetetracarboxylate, bis (1,2,2,6) 6-pentamethyl-4-piperidyl) .di (tridecyl) -1,2,3,4-butanetetracarboxylate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) -2-butyl- 2- (3,5-ditert-butyl-4-hydroxybenzyl) malonate, 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-piperidinol / diethyl succinate polycondensate, 1,6-bis (2,2,6,6-tetramethyl-4-piperidylamino) hexane / dibromoethane polycondensate, 1,6-bis (2,2,6,6-tetramethyl-4-piperidyl) Amino) hexane / 2,4-dichloro-6-morpholino-s-triazine polycondensate, 1,6-bis (2,2,6,6-tetramethyl-4-piperidylamino) hexane / 2,4-dichloro -6-tert-octylamino-s-triazine polycondensate, 1,5,8,12-tetrakis [2,4-bis (N-butyl-N- (2,2,6,6-tetramethyl-4 -Piperidyl) amino) -s-triazin-6-yl] -1,5,8,12-tetraazadodecane, 1,5,8,12-tetrakis [2,4-bis (N-butyl-N- ( 1,2,2,6,6-pentamethyl-4-piperidyl) amino) -s-triazin-6-yl] -1,5,8,12-tetraazadodecane, 1,6,11-tris [2, 4-bis (N-butyl-N- (2,2,6,6-tetramethyl-4-piperidyl) amino) -s-triazin-6-ylamino] undecane, 1,6,11-tris [2,4 -Bis (N-butyl-N- (1,2,2,6,6-pentamethyl-4 Hindered amine compounds such as -piperidyl) amino) -s-triazin-6-ylamino] undecane.
上記２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノール以外の紫外線吸収剤としては、２，４−ジヒドロキシベンゾフェノン、２−ヒドロキシ−４−メトキシベンゾフェノン、２−ヒドロキシ−４−オクトキシベンゾフェノン、５，５’−メチレンビス（２−ヒドロキシ−４−メトキシベンゾフェノン）等の２−ヒドロキシベンゾフェノン類；２−（２’−ヒドロキシ−５’−メチルフェニル）ベンゾトリアゾール、２−（２’−ヒドロキシ−３’，５’−ジ第三ブチルフェニル）−５−クロロベンゾトリアゾール、２−（２’−ヒドロキシ−３’−第三ブチル−５’−メチルフェニル）−５−クロロベンゾトリアゾール、２−（２’−ヒドロキシ−５’−第三オクチルフェニル）ベンゾトリアゾール、２−（２’−ヒドロキシ−３’，５’−ジクミルフェニル）ベンゾトリアゾール、２−（２’−ヒドロキシ−３’−第三ブチル−５’−カルボキシフェニル）ベンゾトリアゾール等の２−（２’−ヒドロキシフェニル）ベンゾトリアゾール類；フェニルサリシレート、レゾルシノールモノベンゾエート、２，４−ジ第三ブチルフェニル−３，５−ジ第三ブチル−４−ヒドロキシベンゾエート、２，４−ジ第三アミルフェニル−３，５−ジ第三ブチル−４−ヒドロキシベンゾエート、ヘキサデシル−３，５−ジ第三ブチル−４−ヒドロキシベンゾエート等のベンゾエート類；２−エチル−２’−エトキシオキザニリド、２−エトキシ−４’−ドデシルオキザニリド等の置換オキザニリド類；エチル−α−シアノ−β，β−ジフェニルアクリレート、メチル−２−シアノ−３−メチル−３−（ｐ−メトキシフェニル）アクリレート等のシアノアクリレート類；２−（２−ヒドロキシ−４−オクトキシフェニル）−４，６−ビス（２，４−ジ第三ブチルフェニル）−ｓ−トリアジン、２−（２−ヒドロキシ−４−メトキシフェニル）−４，６−ジフェニル−ｓ−トリアジン、２−（２−ヒドロキシ−４−プロポキシ−５−メチルフェニル）−４，６−ビス（２，４−ジ第三ブチルフェニル）−ｓ−トリアジン等のトリアリールトリアジン類が挙げられる。 Examples of ultraviolet absorbers other than the 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy- 2-hydroxybenzophenones such as 4-octoxybenzophenone and 5,5′-methylenebis (2-hydroxy-4-methoxybenzophenone); 2- (2′-hydroxy-5′-methylphenyl) benzotriazole, 2- ( 2′-hydroxy-3 ′, 5′-ditert-butylphenyl) -5-chlorobenzotriazole, 2- (2′-hydroxy-3′-tert-butyl-5′-methylphenyl) -5-chlorobenzo Triazole, 2- (2′-hydroxy-5′-tert-octylphenyl) benzotriazole, 2- 2- (2′-hydroxy) such as 2′-hydroxy-3 ′, 5′-dicumylphenyl) benzotriazole, 2- (2′-hydroxy-3′-tert-butyl-5′-carboxyphenyl) benzotriazole Phenyl) benzotriazoles; phenyl salicylate, resorcinol monobenzoate, 2,4-ditert-butylphenyl-3,5-ditert-butyl-4-hydroxybenzoate, 2,4-ditert-amylphenyl-3,5 -Benzoates such as di-tert-butyl-4-hydroxybenzoate and hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate; 2-ethyl-2'-ethoxyoxanilide, 2-ethoxy-4'- Substituted oxanilides such as dodecyl oxanilide; ethyl-α-cyano-β, β-diphenyl acrylate, Cyanoacrylates such as ru-2-cyano-3-methyl-3- (p-methoxyphenyl) acrylate; 2- (2-hydroxy-4-octoxyphenyl) -4,6-bis (2,4-di Tert-butylphenyl) -s-triazine, 2- (2-hydroxy-4-methoxyphenyl) -4,6-diphenyl-s-triazine, 2- (2-hydroxy-4-propoxy-5-methylphenyl)- And triaryltriazines such as 4,6-bis (2,4-ditert-butylphenyl) -s-triazine.
本発明のポリエステル樹脂組成物は、さらに、通常樹脂へ用いられるチオエーテル系酸化防止剤；リン酸エステル金属塩、ベンジリデンソルビトール、安息香酸誘導体の金属塩などの造核剤；重金属不活性化剤；脂肪酸金属塩；ハイドロタルサイト；充填剤；顔料；染料；難燃剤；加工性改良剤などを用いてもよい。 The polyester resin composition of the present invention further comprises a thioether antioxidant generally used for resins; nucleating agents such as phosphate metal salts, benzylidene sorbitol, metal salts of benzoic acid derivatives; heavy metal deactivators; fatty acids Metal salts; hydrotalcite; fillers; pigments; dyes; flame retardants;
本発明のポリエステル樹脂組成物の製造方法は特に制限されるものではなく、成分（Ａ）と成分（Ｂ）を容器中で不活性雰囲気下に加熱溶融して撹拌混合しながら、溶融状態のままアルミ製のトレーに移して冷却したり、フレーカーにより冷却粉砕する方法。成分（Ａ）と成分（Ｂ）を溶媒に溶解して均一になった後、脱溶媒して溶融混合して、取り出し冷却粉砕する方法、成分（Ａ）と成分（Ｂ）の粉末をヘンシェルミキサーなどで混合する方法などにより成分（Ａ）と成分（Ｂ）を予め混合したものをポリエステル樹脂に添加する方法、成分（Ａ）、成分（Ｂ）およびポリエステル樹脂を一度に混合する方法などいずれでもよく、混合物を加熱溶融混練して均一な組成物にする加工機としては、押出機、バンバリーミキサー等がある。一旦溶液化する方法は、脱溶媒が必要で工程が増えるため経済的には不利であるが処理温度が比較的低温ですむため成分（Ａ）や成分（Ｂ）が熱により着色や分解することを抑制できる。 The production method of the polyester resin composition of the present invention is not particularly limited, and the component (A) and the component (B) are heated and melted in an inert atmosphere in a container and stirred and mixed, and remain in a molten state. Transfer to an aluminum tray and cool, or cool and pulverize with a flaker. A method in which component (A) and component (B) are dissolved in a solvent to be uniform, and then desolvated, melted and mixed, taken out, cooled and pulverized, and powders of component (A) and component (B) are mixed in a Henschel mixer Any method such as a method of adding a component (A) and a component (B) premixed to a polyester resin, a method of mixing a component (A), a component (B) and a polyester resin at a time, etc. Often, processing machines that heat and knead the mixture to obtain a uniform composition include an extruder and a Banbury mixer. The solution method is disadvantageous economically because it requires solvent removal and increases the number of processes, but the processing temperature is relatively low, so that component (A) and component (B) are colored or decomposed by heat. Can be suppressed.
（実施例）
以下、実施例により本発明を詳細に説明する。
(Example)
Hereinafter, the present invention will be described in detail by way of examples.
実施例１
ポリエチレンテレフタレート（デュポン社製：Ｍｅｌｉｎａｒ Ｌａｓｅｒ＋）１００質量部に、２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノール１５質量部、表１記載のリン系酸化防止剤３重量部を配合して２８０℃で押出し成形してペレットとして、１６０℃オーブンで２４時間乾燥した。
Example 1
100 parts by mass of polyethylene terephthalate (manufactured by DuPont: Melinar Laser +), 15 parts by mass of 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol, phosphorus-based antioxidant 3 described in Table 1 Part by weight was blended and extruded at 280 ° C. to form pellets, which were dried in a 160 ° C. oven for 24 hours.
比較例１
リン系酸化防止剤を用いないか、リン系以外の酸化防止剤を用いたこと以外は実施例１と同様にして試験片を得た。
Comparative Example 1
A test piece was obtained in the same manner as in Example 1 except that no phosphorus antioxidant was used or an antioxidant other than phosphorus was used.
得られたペレットの乾燥前と乾燥後の黄色度を多光源分光測色計（スガ試験機株式会社製）で測定して着色性試験として評価した。結果を表１に示す。 The yellowness before and after drying of the obtained pellets was measured with a multi-light source spectrocolorimeter (manufactured by Suga Test Instruments Co., Ltd.) and evaluated as a coloring test. The results are shown in Table 1.
＊２：ビス（２，４−ジ第三ブチルフェニル）ペンタエリスリトールジホスファイト
＊３：ビス（２，６−ジ第三ブチル−４−メチルフェニル）ペンタエリスリトールジホスファイト
＊４：ビス（２，４−ビス（１−メチル−１−フェニルエチル）フェニル）ペンタエリスリトールジホスファイト
＊５：２，２’−メチレンビス（４，６−ジ第三ブチルフェニル）−２−エチルヘキシルホスファイト
＊６：テトラキス（３−（３，５−ジ第三ブチル−４−ヒドロキシフェニル）プロピオニルオキシメチル）メタン
＊７：ジラウロイルチオジプロピオネート
表１の比較例１−１〜１−３より明らかなように、２，２’−メチレンビス（４−第三オクチル−６−ベンゾトリアゾリル）フェノールを大量に配合したポリエステル樹脂は、乾燥工程により着色し、フェノール系酸化防止剤やチオエーテル系酸化防止剤では着色は防止できないが、実施例１−１〜１−４より明らかなようにリン系酸化防止剤を添加することにより乾燥時の着色が抑制されている。 As is clear from Comparative Examples 1-1 to 1-3 in Table 1, the polyester resin containing a large amount of 2,2′-methylenebis (4-tert-octyl-6-benzotriazolyl) phenol is a drying step. Although it cannot be colored with a phenolic antioxidant or a thioether antioxidant, it is clear when dried by adding a phosphorus antioxidant as is clear from Examples 1-1 to 1-4. Is suppressed.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003370237A JP4925557B2 (en) | 2003-10-30 | 2003-10-30 | Polyester resin composition |
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| JP2003370237A JP4925557B2 (en) | 2003-10-30 | 2003-10-30 | Polyester resin composition |
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| EP3670595A1 (en) * | 2018-12-19 | 2020-06-24 | Covestro Deutschland AG | Thermoplastic compositions with good thermal stability |
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