DK3147317T3 - Tripentylestere af trimellitsyre - Google Patents
Tripentylestere af trimellitsyre Download PDFInfo
- Publication number
- DK3147317T3 DK3147317T3 DK15187128.2T DK15187128T DK3147317T3 DK 3147317 T3 DK3147317 T3 DK 3147317T3 DK 15187128 T DK15187128 T DK 15187128T DK 3147317 T3 DK3147317 T3 DK 3147317T3
- Authority
- DK
- Denmark
- Prior art keywords
- esters
- isomeric
- mixture
- trimellitic acid
- mixtures
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 208
- 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 claims description 148
- 150000002148 esters Chemical class 0.000 claims description 119
- -1 coatings Substances 0.000 claims description 115
- 239000004014 plasticizer Substances 0.000 claims description 75
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 34
- 229920000642 polymer Polymers 0.000 claims description 30
- 239000004800 polyvinyl chloride Substances 0.000 claims description 29
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 27
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 11
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 229920001944 Plastisol Polymers 0.000 claims description 9
- 239000004999 plastisol Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 7
- 238000009826 distribution Methods 0.000 claims description 6
- 239000000020 Nitrocellulose Substances 0.000 claims description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 5
- 239000000976 ink Substances 0.000 claims description 5
- 229920001220 nitrocellulos Polymers 0.000 claims description 5
- 229920001021 polysulfide Polymers 0.000 claims description 5
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 4
- 238000009413 insulation Methods 0.000 claims description 4
- 125000005498 phthalate group Chemical class 0.000 claims description 4
- 239000004626 polylactic acid Substances 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002649 leather substitute Substances 0.000 claims description 3
- 238000004806 packaging method and process Methods 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 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 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- 229960002479 isosorbide Drugs 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 17
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 4
- 239000011888 foil Substances 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- BJXXCOMGRRCAGN-CLFAGFIQSA-N [2,2-bis(hydroxymethyl)-3-[(z)-octadec-9-enoyl]oxypropyl] (z)-octadec-9-enoate Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCC\C=C/CCCCCCCC BJXXCOMGRRCAGN-CLFAGFIQSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 229920002681 hypalon Polymers 0.000 claims 1
- 239000005077 polysulfide Substances 0.000 claims 1
- 150000008117 polysulfides Polymers 0.000 claims 1
- 239000000565 sealant Substances 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- 125000005591 trimellitate group Chemical group 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000013508 migration Methods 0.000 description 12
- 230000005012 migration Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 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 11
- 230000032050 esterification Effects 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 238000005809 transesterification reaction Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229920005669 high impact polystyrene Polymers 0.000 description 6
- 239000004797 high-impact polystyrene Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000005259 measurement Methods 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
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 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 5
- 239000000463 material Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000007037 hydroformylation reaction Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 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
- 125000005590 trimellitic acid group Chemical class 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
- 239000004808 2-ethylhexylester Substances 0.000 description 3
- 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
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 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
- 150000001860 citric acid derivatives Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 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 3
- 239000012074 organic phase Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- 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
- 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
- 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
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene 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
- BFKVXNPJXXJUGQ-UHFFFAOYSA-N [CH2]CCCC Chemical compound [CH2]CCCC BFKVXNPJXXJUGQ-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 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
- 238000003490 calendering Methods 0.000 description 2
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- 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
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- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical class OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
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- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/12—Preparation of carboxylic acid esters from asymmetrical anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/16—Esters of inorganic acids
- C08L1/18—Cellulose nitrate, i.e. nitrocellulose
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L23/32—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with compounds containing phosphorus or sulfur
- C08L23/34—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with compounds containing phosphorus or sulfur by chlorosulfonation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
1. Blandinger af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper, kendetegnet ved, at mere end 5 mol-% af de i esterblandingen bundne isomere pentylgrupper er forgrenede, kendetegnet ved, at i det mindste 50 mol-% af de i esterblandingen bundne forgrenede isomere pentylgrupper er 2-methylbutylgrupper.
2. Blandinger ifølge krav 1, kendetegnet ved, at i det mindste 15 mol-%, fortrinsvis i det mindste 25 mol-%, af de i esterblandingen bundne isomere pentylgrupper er forgrenede.
3. Blandinger ifølge et af kravene 1 eller 2, kendetegnet ved, at i det mindste 80 mol-% af de i esterblandingen bundne forgrenede isomere pentylgrupper er 2-methylbutylgrupper.
4. Blandinger ifølge et af kravene 1 til 3, kendetegnet ved, at mere end 10 mol-%, fortrinsvis mere end 20 mol-%, af de i esterblandingen bundne isomere pentylgrupper er lineære.
5. Fremgangsmåde til fremstilling af blandinger af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper ifølge krav 1 til 4, kendetegnet ved, at trimellitsyre og/eller et trimellitsyrederivat omsættes med en blanding af isomere pentanoler, idet mere end 5 mol-% af de i blandingen af de isomere pentanoler bundne isomere pentylgrupper er forgrenede.
6. Fremgangsmåde ifølge krav 5, kendetegnet ved, at en eller flere trimellitsyretrialkylestere, hvori alkylgrupperne fra esterfunktionerne hver især omfatter mindre end 4 carbonatomer, forestres med en blanding af isomere pentanoler, idet mere end 5 mol-% af de i blandingen af de isomere pentanoler bundne isomere pentylgrupper er forgrenede.
7. Fremgangsmåde ifølge et af kravene 5 eller 6, kendetegnet ved, at reaktionsblandingen ved reaktionen opvarmes til kogning, og i det mindste 0,2 mol-ækvivalent af mængden af blandingen af isomerer pentanoler, som er nødvendige til indføringen af alle i esterblandingen bundne isomere pentolgrupper, først tilsættes til reaktionsblandingen, som indeholder trimellitsyren og/eller trimellitsyrederivatet, når kogetemperaturen er opnået.
8. Fremgangsmåde til fremstilling af blandinger af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper ifølge krav 1 til 4, kendetegnet ved, at • i det mindste to isomerrene tripentylestere af trimellitsyre, som er forskellige i isomerien af de i esteren bundne pentylgrupper, • i det mindste to blandinger af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper, som er forskellige i isomerfordelingen af de i esterblandingen bundne isomere pentylgrupper eller • i det mindste en isomerren tripentylester af trimellitsyre og i det mindste en blanding af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper blandes med hinanden, således at mere end 5 mol-% af de i den sammenblandede esterblanding bundne isomere pentylgrupper er forgrenet.
9. Anvendelse af blandinger af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper ifølge et af kravene 1 til 4 som blødgører eller som en del af en blødgørersammensætning, som ud over blandingerne af triisopentylestere af trimellitsyre indeholder i det mindste en yderligere polymer-blødgørende forbindelse, til polymerer, navnlig til PVC eller vinylchlorid-holdige copolymerer.
10. Anvendelse ifølge krav 9, kendetegnet ved, at blandingen af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper som blødgører eller som en del af en blødgørersammensætning, anvendes i klæbestoffer, tætningsmasser, belægningsmasser, lakker, malinger, plastisoler, skum, kunstlæder, gulvbelægninger (f.eks. dæklag), tagbaner, gulvunderlagsbeskyttelse, vævsbelægninger, kabler, trådisoleringer, slanger, ekstruderingsartikler, folier, inden for bilinteriørområdet, i tapeter, blæk, legetøj, kontaktfolier, fødevareemballeringer eller medicinske artikler, eksempelvis slanger eller blodposer.
11. Blødgørersammensætning omfattende blandinger af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper ifølge et af kravene 1 til 4 samt i det mindste en yderligere polymer-blødgørende forbindelse fra gruppen af alkylbenzoater, dialkyladipater, glycerinestere, citronsyretrialkylestere, acylerede citronsyretrialkylestere, glykoldibenzoater, trimellitater med andre grupper end beskrevet i den foreliggende opfindelse, dialkylterephthalater, dialkylphthalater, estere af furandicarboxylsyre, dialkanoylestere af dianhydrohexitoler (f.eks. isosorbid), epoxiderede fedtsyrealkylestere, polymerblødgørere, eksempelvis polyadipater, og dialkylestere af 1,2-, 1,3- eller 1,4-cyclohexandicarboxylsyre.
12. Kunststofsammensætning indeholdende en blanding af triisopentylestere af trimellitsyre omfattende isomere pentylgrupper ifølge et af kravene 1 til 4 eller en blødgørersammensætning ifølge krav 11 og en eller flere polymerer fra gruppen, som dannes af polyvinylchlorid, co-polymerer af vinylchlorid med vinylacetat eller med butylacrylat, polyalkylmethacrylat (PAMA), polyvinylbutyral (PVB), chlorsulfuneret polyethylen, polyurethan, polysulfider, polymælkesyre (PLA), polyhydroxybutyral (PHB) og nitrocellulose.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15187128.2A EP3147317B1 (de) | 2015-09-28 | 2015-09-28 | Tripentylester der trimellitsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3147317T3 true DK3147317T3 (da) | 2017-12-04 |
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| Application Number | Title | Priority Date | Filing Date |
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| DK15187128.2T DK3147317T3 (da) | 2015-09-28 | 2015-09-28 | Tripentylestere af trimellitsyre |
| DK16185659.6T DK3147318T3 (da) | 2015-09-28 | 2016-08-25 | Tripentylestere af trimellitsyre |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| DK16185659.6T DK3147318T3 (da) | 2015-09-28 | 2016-08-25 | Tripentylestere af trimellitsyre |
Country Status (14)
| Country | Link |
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| US (2) | US10577479B2 (da) |
| EP (3) | EP3147317B1 (da) |
| JP (2) | JP6829036B2 (da) |
| KR (2) | KR102050944B1 (da) |
| CN (2) | CN107011535B (da) |
| CA (1) | CA2943327C (da) |
| DK (2) | DK3147317T3 (da) |
| ES (2) | ES2648806T3 (da) |
| HU (1) | HUE037333T2 (da) |
| NO (1) | NO3147317T3 (da) |
| PL (2) | PL3147317T3 (da) |
| SG (1) | SG10201607129TA (da) |
| SI (1) | SI3147317T1 (da) |
| TW (2) | TWI683805B (da) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DK3147317T3 (da) * | 2015-09-28 | 2017-12-04 | Evonik Degussa Gmbh | Tripentylestere af trimellitsyre |
| EP3440044A4 (en) * | 2016-04-07 | 2019-12-25 | Ascend Performance Materials Operations LLC | TRI-CARBON COMPOUNDS AS A VOC-LOW COALSCENT AND SOFTENER |
| US20190161597A1 (en) * | 2016-08-01 | 2019-05-30 | Basf Se | Plasticizer composition |
| EP3351526B1 (de) | 2017-01-20 | 2020-11-18 | Evonik Operations GmbH | Diisopentylterephthalat |
| TWI748055B (zh) | 2017-02-10 | 2021-12-01 | 南韓商Ｌｇ化學股份有限公司 | 塑化劑組成物及含彼之樹脂組成物 |
| CN107540550A (zh) * | 2017-09-28 | 2018-01-05 | 江苏正丹化学工业股份有限公司 | 一种偏苯三酸三辛酯的高效合成方法 |
| CN112300439B (zh) * | 2018-01-02 | 2022-04-29 | 揭阳市超越塑胶实业有限公司 | 一种酯类增塑剂及其应用 |
| KR102294862B1 (ko) * | 2018-06-12 | 2021-08-30 | 주식회사 엘지화학 | 가소제 조성물 및 이를 포함하는 수지 조성물 |
| US11827767B2 (en) | 2018-07-12 | 2023-11-28 | Lg Chem, Ltd. | Plasticizer composition comprising cyclohexane polyester-based substance and resin composition comprising the same |
| EP3875526B1 (en) * | 2018-10-29 | 2022-10-19 | Lg Chem, Ltd. | Cyclohexane triester-based plasticizer composition, and resin composition comprising the same |
| CN109970556B (zh) * | 2019-02-21 | 2022-02-22 | 南京林业大学 | 一种植物油基多酸醇醚酯及其制备方法和应用 |
| US12012499B2 (en) | 2019-05-02 | 2024-06-18 | Lg Chem, Ltd. | Cyclohexane triester-based plasticizer composition and resin composition including the same |
| ES2989679T3 (es) * | 2019-05-02 | 2024-11-27 | Lg Chemical Ltd | Composición plastificante y composición de resina que comprende la misma |
| KR102496350B1 (ko) * | 2019-06-05 | 2023-02-03 | 한화솔루션 주식회사 | 가소제 조성물 및 이를 포함하는 염화비닐계 수지 조성물 |
| 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 |
| PL3838888T3 (pl) | 2019-12-17 | 2022-07-11 | Evonik Operations Gmbh | Triestry kwasu cykloheksanotripropionowego |
| EP4105272A1 (de) | 2021-06-15 | 2022-12-21 | Evonik Operations GmbH | Weichmacherzusammensetzung umfassend tripentylester der 1,2,4-cyclohexantricarbonsäure |
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