JP2017066139A - トリメリット酸のトリペンチルエステル - Google Patents
トリメリット酸のトリペンチルエステル Download PDFInfo
- Publication number
- JP2017066139A JP2017066139A JP2016189561A JP2016189561A JP2017066139A JP 2017066139 A JP2017066139 A JP 2017066139A JP 2016189561 A JP2016189561 A JP 2016189561A JP 2016189561 A JP2016189561 A JP 2016189561A JP 2017066139 A JP2017066139 A JP 2017066139A
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- Prior art keywords
- mixture
- trimellitic acid
- mol
- esters
- ester
- 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.)
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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 title claims abstract description 243
- 150000002148 esters Chemical class 0.000 title claims abstract description 170
- 239000000203 mixture Substances 0.000 claims abstract description 257
- 239000004014 plasticizer Substances 0.000 claims abstract description 104
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims abstract description 84
- 239000004800 polyvinyl chloride Substances 0.000 claims abstract description 43
- 229920000915 polyvinyl chloride Polymers 0.000 claims abstract description 40
- -1 trimellitic acid ester Chemical class 0.000 claims abstract description 33
- 229920001577 copolymer Polymers 0.000 claims abstract description 20
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 10
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 70
- 229920000642 polymer Polymers 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 23
- 229920003023 plastic Polymers 0.000 claims description 22
- 239000004033 plastic Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 18
- 125000005591 trimellitate group Chemical group 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 15
- 229920001944 Plastisol Polymers 0.000 claims description 13
- 239000004999 plastisol Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 10
- 238000009826 distribution Methods 0.000 claims description 8
- 239000012528 membrane Substances 0.000 claims description 8
- 239000000020 Nitrocellulose Substances 0.000 claims description 7
- 229910000831 Steel Inorganic materials 0.000 claims description 7
- 239000000853 adhesive Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 7
- 239000003086 colorant Substances 0.000 claims description 7
- 238000009413 insulation Methods 0.000 claims description 7
- 229920001220 nitrocellulos Polymers 0.000 claims description 7
- 239000005077 polysulfide Substances 0.000 claims description 7
- 229920001021 polysulfide Polymers 0.000 claims description 7
- 150000008117 polysulfides Polymers 0.000 claims description 7
- 239000010959 steel Substances 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 125000005498 phthalate group Chemical class 0.000 claims description 6
- 239000004626 polylactic acid Substances 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 5
- 239000008280 blood Substances 0.000 claims description 5
- 210000004369 blood Anatomy 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 238000001125 extrusion Methods 0.000 claims description 5
- 239000006260 foam Substances 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 239000000976 ink Substances 0.000 claims description 5
- 239000002649 leather substitute Substances 0.000 claims description 5
- 238000004806 packaging method and process Methods 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000000565 sealant Substances 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 229920002681 hypalon Polymers 0.000 claims description 4
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 3
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 3
- 150000002314 glycerols Chemical class 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 229960002479 isosorbide Drugs 0.000 claims description 3
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011814 protection agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 238000013508 migration Methods 0.000 abstract description 17
- 230000005012 migration Effects 0.000 abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 230000032050 esterification Effects 0.000 description 16
- 238000005886 esterification reaction Methods 0.000 description 16
- 238000005809 transesterification reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000002156 mixing Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 11
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- WTNDADANUZETTI-UHFFFAOYSA-N cyclohexane-1,2,4-tricarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C(C(O)=O)C1 WTNDADANUZETTI-UHFFFAOYSA-N 0.000 description 9
- 125000005590 trimellitic acid group Chemical class 0.000 description 9
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000004808 2-ethylhexylester Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KRADHMIOFJQKEZ-UHFFFAOYSA-N Tri-2-ethylhexyl trimellitate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)=C1 KRADHMIOFJQKEZ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000003490 calendering Methods 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000007037 hydroformylation reaction Methods 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RJIFVNWOLLIBJV-UHFFFAOYSA-N tributyl benzene-1,2,4-tricarboxylate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C(C(=O)OCCCC)=C1 RJIFVNWOLLIBJV-UHFFFAOYSA-N 0.000 description 4
- MJHNUUNSCNRGJE-UHFFFAOYSA-N trimethyl benzene-1,2,4-tricarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(C(=O)OC)=C1 MJHNUUNSCNRGJE-UHFFFAOYSA-N 0.000 description 4
- 239000004034 viscosity adjusting agent Substances 0.000 description 4
- 239000002759 woven fabric Substances 0.000 description 4
- BJQHLKABXJIVAM-UHFFFAOYSA-N Diethylhexyl phthalate Natural products CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 229940081735 acetylcellulose Drugs 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical class OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 229920005669 high impact polystyrene Polymers 0.000 description 3
- 239000004797 high-impact polystyrene Substances 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 238000004804 winding Methods 0.000 description 3
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- BJQHLKABXJIVAM-BGYRXZFFSA-N 1-o-[(2r)-2-ethylhexyl] 2-o-[(2s)-2-ethylhexyl] benzene-1,2-dicarboxylate Chemical compound CCCC[C@H](CC)COC(=O)C1=CC=CC=C1C(=O)OC[C@H](CC)CCCC BJQHLKABXJIVAM-BGYRXZFFSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XFDQLDNQZFOAFK-UHFFFAOYSA-N 2-benzoyloxyethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOC(=O)C1=CC=CC=C1 XFDQLDNQZFOAFK-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 2
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 2
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PEIIRIVDOVFUIW-UHFFFAOYSA-N bis(7-methyloctyl) benzene-1,4-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCC(C)C)C=C1 PEIIRIVDOVFUIW-UHFFFAOYSA-N 0.000 description 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 229920006248 expandable polystyrene Polymers 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
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- 239000004611 light stabiliser Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
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- 229950009195 phenylpropanol Drugs 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
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- 229920002647 polyamide Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000013615 primer Substances 0.000 description 2
- 239000002987 primer (paints) Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011265 semifinished product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 150000003900 succinic acid esters Chemical class 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 229920002397 thermoplastic olefin Polymers 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 150000005691 triesters Chemical class 0.000 description 2
- MXHBQKVKHGQWRB-UHFFFAOYSA-N trihexyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC)C(C(=O)OCCCCCC)=C1 MXHBQKVKHGQWRB-UHFFFAOYSA-N 0.000 description 2
- UNCANWJZJSLQNV-UHFFFAOYSA-N tripentyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCCCCOC(=O)C1CCC(C(=O)OCCCCC)C(C(=O)OCCCCC)C1 UNCANWJZJSLQNV-UHFFFAOYSA-N 0.000 description 2
- ZMZHHPWZDJMXEX-UHFFFAOYSA-N tris(3-methylbutyl) cyclohexane-1,2,4-tricarboxylate Chemical compound CC(C)CCOC(=O)C1CCC(C(=O)OCCC(C)C)C(C(=O)OCCC(C)C)C1 ZMZHHPWZDJMXEX-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 150000003754 zirconium Chemical class 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- MJFKUMUTRUNHDB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid Chemical class OC(=O)CC(O)(CC(O)=O)C(O)=O.OC(=O)CC(O)(CC(O)=O)C(O)=O.OC(=O)CC(O)(CC(O)=O)C(O)=O.OC(=O)CC(O)(CC(O)=O)C(O)=O MJFKUMUTRUNHDB-UHFFFAOYSA-N 0.000 description 1
- JQXYBDVZAUEPDL-UHFFFAOYSA-N 2-methylidene-5-phenylpent-4-enoic acid Chemical compound OC(=O)C(=C)CC=CC1=CC=CC=C1 JQXYBDVZAUEPDL-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 description 1
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- YAAQEISEHDUIFO-UHFFFAOYSA-N C=CC#N.OC(=O)C=CC=CC1=CC=CC=C1 Chemical compound C=CC#N.OC(=O)C=CC=CC1=CC=CC=C1 YAAQEISEHDUIFO-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical class [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- MNUSMUGFHGAOIW-UHFFFAOYSA-N cyclohexane-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1CCCCC1(C(O)=O)C(O)=O MNUSMUGFHGAOIW-UHFFFAOYSA-N 0.000 description 1
- 239000004806 diisononylester Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 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
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- CPYFCVVBZUCVKJ-UHFFFAOYSA-N tridodecyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCCC)=C1 CPYFCVVBZUCVKJ-UHFFFAOYSA-N 0.000 description 1
- DEIJHCATUHBNIH-UHFFFAOYSA-N trimethyl cyclohexane-1,2,4-tricarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)C(C(=O)OC)C1 DEIJHCATUHBNIH-UHFFFAOYSA-N 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- RCPMCMBYXMQBLR-UHFFFAOYSA-N tris(7-methyloctyl) cyclohexane-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCC(C(=O)OCCCCCCC(C)C)C(C(=O)OCCCCCCC(C)C)C1 RCPMCMBYXMQBLR-UHFFFAOYSA-N 0.000 description 1
- SMYKBXMWXCZOLU-UHFFFAOYSA-N tris-decyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCCCC)C(C(=O)OCCCCCCCCCC)=C1 SMYKBXMWXCZOLU-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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-
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Abstract
Description
・エステル中で結合されたペンチル基の異性体において異なる、トリメリット酸の純粋異性体トリペンチルエステルの少なくとも2種、
・エステル混合物中で結合された異性体ペンチル基の異性体分布において異なる、異性体ペンチル基を含有するトリメリット酸のトリイソペンチルエステルの混合物の少なくとも2種、又は
・トリメリット酸の純粋異性体トリペンチルエステルの少なくとも1種、及び異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物の少なくとも1種、
を相互に混合し、これによって一緒に混合したエステル混合物中で結合された異性体ペンチル基の5mol%超、好ましくは少なくとも15mol%、好適には少なくとも20mol%、より好ましくは少なくとも25mol%、特に好ましくは少なくとも50mol%、さらに好ましくは少なくとも67mol%、極めて特に好ましくは少なくとも75mol%、とりわけ少なくとも80mol%が、分枝状である。
撹拌機付撹拌フラスコ、試料採取支持部、滴下漏斗、浸漬管、温度計、及び強力冷却機が取り付けられた水分離器を有する装置(この際、水分離器にはC4トリメリテート製造の場合、20cmのラシヒリング塔が前接続されていた)に、トリメリット酸無水物(Sigma Aldrich、純度97%)576.0g(3mol)、及び量m1のアルコールAを充填した。この装置に1時間、窒素(6l/h)を浸漬管によりパージし、それからテトラ−n−ブチルチタネート(Sigma Aldrich、純度97%超)を0.8g(0.75mmol)添加した。反応終了まで持続的に窒素(6l/h)を吹き込む一方、混合物を撹拌しながら、沸騰するまで加熱した。反応により生じる水を、水分離器によって連続的に除去した。240℃の反応温度から、アルコールAの量m2、及びテトラ−n−ブチルチタネート0.8g(0.75mmol)を、反応温度が240℃未満に低下しない速度で計量供給した。水分離器によって108ml(6mol)の水が分離されたら直ちに、反応溶液の試料によって、DIN EN ISO 2114により酸価を測定した。測定した各酸価に応じて、反応混合物の酸価が試料1gあたり0.1mgKOH未満になるまで、反応混合物をさらに加熱した(合計反応時間t)。
GC分析は、以下のパラメータを用いて行った:
・キャピラリーカラム30m DB5;0.25mm ID;0.25μmの膜
・キャリアガス:ヘリウム
・カラム予圧:150kPa
・カラム注入部で冷却
・炉温プログラム(所要時間51分):50℃(1分)、15℃/分で350℃に加熱(14分間温度を維持)
・インジェクタ:50℃
・検知器(FID):425℃
・注入体積:0.3μl。
トリイソペンチルエステル混合物の組成(すなわち全ペンチル基の合計に対する様々な異性体ペンチル基の各割合)の特定は、例えば1H−NMR、及び13C−NMR分光分析によって行うことができる。ここで組成の測定は、1H−NMR分光分析によって、重クロロホルム(CDCl3)中のトリイソペンチルエステル混合物の溶液を用いて行った。スペクトル吸収のために、物質20mgを0.6mlのCDCl3中に(TMSを1質量%含有)溶解させ、直径5mmのNMR管に充填した。試験すべき物質も、使用するCDCl3も、まず分子ふるいによって乾燥させ、場合によって存在する水による測定値の変動を排除する。NMR分光分析試験は原則的に、あらゆる市販のNMR装置によって行うことができる。本願におけるNMR分光分析試験のためには、Bruker社のAvance 500 型装置を使用した。スペクトルは、303Kの温度で、遅延(遅れ)d1=5秒、32スキャン(往復)、パルス長さ約9.5μs(90°励起パルス)、及び5mmのBBO試料体(Broad Band Observer、広帯域観察)による掃射幅(スペクトル幅)10000Hzで記録した。共鳴シグナルは、テトラメチルシランの化学シフト(TMS=0ppm)を、内部標準として記録した。他の市販のNMR装置により、同じ稼働パラメータでは同等の結果が得られる。
以下の例に必要な試験体は、以下の処方を乾燥混合(ドライブレンド製造)、カレンダー成形(ローラ加工)、及びプレス成形することにより製造する:
・回転数プログラム:アクティブ
・特性:回転数50回転/分、維持時間9分
(回転数)増加時間:1分
回転数100回転/分、維持時間20分
・温度:88℃
・測定範囲:2Nm
・減衰:3。
段階 呼称 温度 時間 スリット幅 回転数
(℃) (秒) (mm) (rpm)
1 ドライブレンドの可塑化 165 60 0.2 5
2 スリットの増大 165 30 0.5 20
3 試料回転部の作動 165 170 0.5 20
4 巻取りシート最適化 165 30 0.5 25
5 巻取りシートの取り外し 165 60 0.5 7
段階 呼称 温度(℃) 圧力(bar) 時間(秒)
1 事前プレス 175 5 60
2 プレス成形 175 200 120
3 冷却 40 200 270
各ドライブレンドを製造する間、加工性の基準として用いられる可塑剤吸収速度を測定した。短い可塑剤吸収時間により、実際には低い加工温度、又は高い生成物バッチが、存在する設備で生じる。
可塑剤又は可塑剤組成物を含有する試験体のマイグレーション特性を測定するための試験により、可塑剤含有調製物がその適用において、別の材料と直接接触する際、例えば可塑化したPVC層を硬質PVC層と接触させる際に(いわゆる「多層系」)、どのような挙動を示すのかについて、帰納的な推論ができる。例えばある物品の内部で、可塑化したポリマー含有部材から、可塑化されていないポリマー含有部材に移行する場合、これは、可塑化された部材の不所望の脆性化、及び可塑化されていない部材の軟化につながり、このことが非緻密性、安定性の低下、及び物品の使用時間の短縮につながり得る。これに応じて、僅かなマイグレーション傾向は、多くの適用で使用可能な可塑剤又は可塑剤組成物のこれに相当する成分にとって重要な特性である。
例8で製造された、厚さ1mmのプレス成形プレートを、100mm×100mmの試験体に切断し、24時間、23℃で貯蔵してから、その質量を測定した。
Claims (14)
- 異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物において、エステル混合物中で結合された異性体ペンチル基の5mol%超が分枝状であることを特徴とする、前記混合物。
- エステル混合物中で結合された異性体ペンチル基の少なくとも15mol%、好適には少なくとも25mol%が分枝状であることを特徴とする、請求項1に記載の混合物。
- エステル混合物中で結合された分枝状異性体ペンチル基の少なくとも50mol%、好適には少なくとも80mol%が、2−メチルブチル基であることを特徴とする、請求項1又は2に記載の混合物。
- エステル混合物中で結合された異性体ペンチル基の10mol%超、好適には20mol%超が、直鎖状であることを特徴とする、請求項1から3までのいずれか1項に記載の混合物。
- 請求項1から4までのいずれか1項に記載された、異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物を製造する方法において、
トリメリット酸及び/又はトリメリット酸誘導体を異性体ペンタノールの混合物と反応させ、ここで異性体ペンタノールの混合物中で結合された異性体ペンチル基の5mol%超が分枝状であることを特徴とする、前記方法。 - エステル官能基のアルキル基がそれぞれ4個未満の炭素原子を有するトリメリット酸トリアルキルエステルの1種以上を、異性体ペンタノールの混合物によってエステル交換し、異性体ペンタノールの混合物中で結合された異性体ペンチル基の5mol%超が分枝状であることを特徴とする、請求項5に記載の方法。
- 反応に際して、反応混合物を沸騰するまで加熱し、エステル混合物中で結合された全ての異性体ペンチル基を導入するために必要な異性体ペンタノール混合物量に対して少なくとも0.2mol当量を、トリメリット酸及び/又はトリメリット酸誘導体を含有する前記反応混合物に、沸点に達した後に初めて添加することを特徴とする、請求項5又は6に記載の方法。
- 請求項1から4までのいずれか1項に記載された、異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物を製造する方法において、
・エステル中で結合されたペンチル基の異性体において異なる、トリメリット酸の純粋異性体トリペンチルエステルの少なくとも2種、
・エステル混合物中で結合された異性体ペンチル基の異性体分布において異なる、異性体ペンチル基を含有するトリメリット酸のトリイソペンチルエステルの混合物の少なくとも2種、又は
・トリメリット酸の純粋異性体トリペンチルエステルの少なくとも1種、及び異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物の少なくとも1種、
を相互に混合し、これによって一緒に混合したエステル混合物中で結合された異性体ペンチル基の5mol%超が、分枝状であることを特徴とする、前記方法。 - トリメリット酸及び/又はトリメリット酸誘導体をペンタノールと反応させ、反応混合物を沸騰するまで加熱する、トリメリット酸のトリペンチルエステルを製造するための方法において、エステル混合物中で結合された全てのペンチル基を導入するために必要なペンタノール量に対して少なくとも0.2mol当量を、トリメリット酸及び/又はトリメリット酸誘導体を含有する反応混合物に、沸点に達した後に初めて添加することを特徴とする、前記方法。
- 請求項1から4までのいずれか1項に記載された、異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物の使用であって、ポリマー用、とりわけPVC又は塩化ビニル含有コポリマー用の、可塑剤としての、又はトリメリット酸のトリイソペンチルエステルの混合物以外に、少なくとも1種のさらなるポリマー可塑化化合物を含有する可塑剤組成物の一部としての、前記使用。
- ポリマー用、とりわけPVC又は塩化ビニル含有コポリマー用の、可塑剤としての、又はトリメリット酸のトリペンチルエステルの1種以上以外に、少なくとも1種のさらなるポリマー可塑化化合物を含有する可塑剤組成物の一部としての、トリメリット酸のトリペンチルエステルの使用。
- 請求項10又は11に記載の使用において、異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物、又はトリメリット酸のトリペンチルエステルの1種以上を、可塑剤として、又は可塑剤組成物の一部として、接着剤、封止剤、被覆材料、塗料、着色剤、プラスチゾル、発泡体、人工皮革、床面被覆、例えばトップコート、屋根用の膜構造、基部保護剤、織布被覆、ケーブル、鋼線絶縁、ホース、押出成形品、シート、自動車内部領域、壁紙、インク、玩具、接触シート、食品包装、又は医薬品、例えばチューブ若しくは血液バッグにおいて使用することを特徴とする、前記使用。
- 請求項1から4までのいずれか1項に記載された、異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物、又はトリメリット酸のトリペンチルエステルの1種以上、並びにアルキルベンゾエート、ジアルキルアジペート、グリセリンエステル、クエン酸トリアルキルエステル、アシル化クエン酸トリアルキルエステル、グリコールジベンゾエート、本発明により記載された基とは異なる基を有するトリメリテート、ジアルキルテレフタレート、ジアルキルフタレート、フランジカルボン酸のエステル、ヘキシトール二無水物のジアルカノイルエステル、例えばイソソルビド、エポキシ化脂肪酸アルキルエステル、ポリマー可塑剤、例えばポリアジペートのポリマー可塑剤、及び1,2−、1,3−、又は1,4−シクロヘキサンジカルボン酸のジアルキルエステルの群からのさらなるポリマー可塑化化合物を少なくとも1種含有する、可塑剤組成物。
- 請求項1から4までのいずれか1項に記載された、異性体ペンチル基を含有する、トリメリット酸のトリイソペンチルエステルの混合物、又はトリメリット酸のトリペンチルエステルの1種以上、又は請求項13に記載の可塑剤組成物、並びにポリ塩化ビニル、塩化ビニルと酢酸ビニル若しくはアクリル酸ブチルとのコポリマー、ポリアルキルメタクリレート(PAMA)、ポリビニルブチラール(PVB)、クロロスルホン化ポリエチレン、ポリウレタン、ポリスルフィド、ポリ乳酸(PLA)、ポリヒドロキシブチラール(PHB)、及びニトロセルロースから形成される群からなる1種以上のポリマー1種以上を含有する、プラスチック組成物。
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JP2021073239A (ja) * | 2015-09-28 | 2021-05-13 | エボニック オペレーションズ ゲーエムベーハー | トリメリット酸のトリペンチルエステル |
JPWO2021124901A1 (ja) * | 2019-12-16 | 2021-06-24 | ||
JP7131718B2 (ja) | 2019-12-16 | 2022-09-06 | Dic株式会社 | 塩化ビニル樹脂用可塑剤、塩化ビニル樹脂組成物、並びに当該塩化ビニル樹脂組成物を用いた成形品及びワイヤーハーネス |
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