MXPA01012835A - Uso de los acidos ciclohexanopolicarboxilicos como plastificantes para preparar plasticos clasificados como favorables toxicologicamente. - Google Patents
Uso de los acidos ciclohexanopolicarboxilicos como plastificantes para preparar plasticos clasificados como favorables toxicologicamente.Info
- Publication number
- MXPA01012835A MXPA01012835A MXPA01012835A MXPA01012835A MXPA01012835A MX PA01012835 A MXPA01012835 A MX PA01012835A MX PA01012835 A MXPA01012835 A MX PA01012835A MX PA01012835 A MXPA01012835 A MX PA01012835A MX PA01012835 A MXPA01012835 A MX PA01012835A
- Authority
- MX
- Mexico
- Prior art keywords
- ester
- acid
- cyclohexane
- hydrogenating
- cas
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 45
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000004014 plasticizer Substances 0.000 title claims abstract description 16
- 229920003023 plastic Polymers 0.000 title claims abstract description 13
- 239000004033 plastic Substances 0.000 title claims abstract description 13
- 150000007513 acids Chemical class 0.000 title abstract description 16
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 230000002349 favourable effect Effects 0.000 title abstract description 3
- 210000004185 liver Anatomy 0.000 claims abstract description 22
- 241001465754 Metazoa Species 0.000 claims abstract description 14
- 230000000694 effects Effects 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 102100026798 Peroxisomal acyl-coenzyme A oxidase 1 Human genes 0.000 claims abstract description 10
- 108010008746 palmitoyl CoA oxidase Proteins 0.000 claims abstract description 10
- 230000037396 body weight Effects 0.000 claims abstract description 8
- 241000283984 Rodentia Species 0.000 claims abstract description 5
- 238000011282 treatment Methods 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims description 101
- -1 isononyl Chemical group 0.000 claims description 37
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 claims description 30
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims description 29
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 14
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims description 14
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims description 9
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 claims description 7
- 210000002784 stomach Anatomy 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 claims description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- RKELNIPLHQEBJO-UHFFFAOYSA-N bis(5-methylhexyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCC(C)C RKELNIPLHQEBJO-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- MTYUOIVEVPTXFX-UHFFFAOYSA-N bis(2-propylheptyl) benzene-1,2-dicarboxylate Chemical compound CCCCCC(CCC)COC(=O)C1=CC=CC=C1C(=O)OCC(CCC)CCCCC MTYUOIVEVPTXFX-UHFFFAOYSA-N 0.000 claims description 2
- JANBFCARANRIKJ-UHFFFAOYSA-N bis(3-methylbutyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)C JANBFCARANRIKJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 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 claims 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 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 claims 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims 1
- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 description 28
- JEBXNNPMFYXVHS-UHFFFAOYSA-N cyclohexane-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1C(O)=O JEBXNNPMFYXVHS-UHFFFAOYSA-N 0.000 description 22
- FTHDNRBKSLBLDA-UHFFFAOYSA-N cyclohexane-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)CC(C(O)=O)C1 FTHDNRBKSLBLDA-UHFFFAOYSA-N 0.000 description 21
- 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 18
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 14
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 10
- 239000004808 2-ethylhexylester Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 125000005498 phthalate group Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004806 diisononylester Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 4
- 210000002824 peroxisome Anatomy 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 102000004316 Oxidoreductases Human genes 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 2
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
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- 231100000027 toxicology Toxicity 0.000 description 2
- WLMCLGZZUPUZNF-UHFFFAOYSA-N tris(10-methylundecyl) cyclohexane-1,2,3-tricarboxylate Chemical compound CC(C)CCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCCC(C)C)C1C(=O)OCCCCCCCCCC(C)C WLMCLGZZUPUZNF-UHFFFAOYSA-N 0.000 description 2
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- NYJHZXDGYBQHEW-UHFFFAOYSA-N bis(10-methylundecyl) cyclohexane-1,4-dicarboxylate Chemical compound CC(C)CCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCC(C)C)CC1 NYJHZXDGYBQHEW-UHFFFAOYSA-N 0.000 description 1
- RYZDRFARYDZAKG-UHFFFAOYSA-N bis(16-methylheptadecyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCCCCCCCCC(C)C RYZDRFARYDZAKG-UHFFFAOYSA-N 0.000 description 1
- ODPOQNZEVQLGDI-UHFFFAOYSA-N bis(16-methylheptadecyl) cyclohexane-1,4-dicarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCCCCCCCC(C)C)CC1 ODPOQNZEVQLGDI-UHFFFAOYSA-N 0.000 description 1
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- GXRDMEGSBKPONF-UHFFFAOYSA-N bis(2-methyloctyl) benzene-1,2-dicarboxylate Chemical compound CCCCCCC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)CCCCCC GXRDMEGSBKPONF-UHFFFAOYSA-N 0.000 description 1
- VBOCECROODHYBD-UHFFFAOYSA-N bis(2-methylpropyl) cyclohexane-1,4-dicarboxylate Chemical compound CC(C)COC(=O)C1CCC(C(=O)OCC(C)C)CC1 VBOCECROODHYBD-UHFFFAOYSA-N 0.000 description 1
- RCJYKEBCIPMBED-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,4-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCC(C(=O)OCCCCCCC(C)C)CC1 RCJYKEBCIPMBED-UHFFFAOYSA-N 0.000 description 1
- WZEFLOBFCQPVHR-UHFFFAOYSA-N bis(8-methylnonyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCC(C)C WZEFLOBFCQPVHR-UHFFFAOYSA-N 0.000 description 1
- WQXGVDQCRREHBZ-UHFFFAOYSA-N bis(8-methylnonyl) cyclohexane-1,3-dicarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCC(C)C)C1 WQXGVDQCRREHBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 230000008859 change Effects 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
- DGLJMIOAKPEPBF-UHFFFAOYSA-N cyclohexane-1,1,3,4-tetracarboxylic acid Chemical compound C1(C(CC(CC1)(C(=O)O)C(=O)O)C(=O)O)C(=O)O DGLJMIOAKPEPBF-UHFFFAOYSA-N 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- DQAIJLIWTPSECO-UHFFFAOYSA-N dibutyl cyclohexane-1,3-dicarboxylate Chemical compound CCCCOC(=O)C1CCCC(C(=O)OCCCC)C1 DQAIJLIWTPSECO-UHFFFAOYSA-N 0.000 description 1
- LJENFJPOMYLBLT-UHFFFAOYSA-N dicyclohexyl cyclohexane-1,3-dicarboxylate Chemical compound C1CCC(C(=O)OC2CCCCC2)CC1C(=O)OC1CCCCC1 LJENFJPOMYLBLT-UHFFFAOYSA-N 0.000 description 1
- QBEIDLSJFKAAPR-UHFFFAOYSA-N didecyl cyclohexane-1,4-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCC)CC1 QBEIDLSJFKAAPR-UHFFFAOYSA-N 0.000 description 1
- ZTUZDYWYNQDJKR-UHFFFAOYSA-N diethyl cyclohexane-1,2-dicarboxylate Chemical compound CCOC(=O)C1CCCCC1C(=O)OCC ZTUZDYWYNQDJKR-UHFFFAOYSA-N 0.000 description 1
- MAQGUOIUBYAVNL-UHFFFAOYSA-N diethyl cyclohexane-1,3-dicarboxylate Chemical compound CCOC(=O)C1CCCC(C(=O)OCC)C1 MAQGUOIUBYAVNL-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- AIACXWOETVLBIA-UHFFFAOYSA-N dimethyl cyclohexane-1,2-dicarboxylate Chemical compound COC(=O)C1CCCCC1C(=O)OC AIACXWOETVLBIA-UHFFFAOYSA-N 0.000 description 1
- BZUOYGUOKMUSPA-UHFFFAOYSA-N dimethyl cyclohexane-1,3-dicarboxylate Chemical compound COC(=O)C1CCCC(C(=O)OC)C1 BZUOYGUOKMUSPA-UHFFFAOYSA-N 0.000 description 1
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GVAAKRNEKNTVRW-UHFFFAOYSA-N dioctadecyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCCCCCCCCCCC GVAAKRNEKNTVRW-UHFFFAOYSA-N 0.000 description 1
- SWRYRUMCLDOLEO-UHFFFAOYSA-N dioctadecyl cyclohexane-1,4-dicarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCCCCCCCCCC)CC1 SWRYRUMCLDOLEO-UHFFFAOYSA-N 0.000 description 1
- FUXJJBJXVZIIMV-UHFFFAOYSA-N dioctyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCC FUXJJBJXVZIIMV-UHFFFAOYSA-N 0.000 description 1
- UMYBJJQPKODXDD-UHFFFAOYSA-N ditert-butyl cyclohexane-1,3-dicarboxylate Chemical compound CC(C)(C)OC(=O)C1CCCC(C(=O)OC(C)(C)C)C1 UMYBJJQPKODXDD-UHFFFAOYSA-N 0.000 description 1
- OACQFHLGZUHNQE-UHFFFAOYSA-N diundecyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCCCC OACQFHLGZUHNQE-UHFFFAOYSA-N 0.000 description 1
- RBRQHYROHMOKTH-UHFFFAOYSA-N diundecyl cyclohexane-1,3-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCCCC)C1 RBRQHYROHMOKTH-UHFFFAOYSA-N 0.000 description 1
- GILXYSUFIIWBIB-UHFFFAOYSA-N diundecyl cyclohexane-1,4-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCCC)CC1 GILXYSUFIIWBIB-UHFFFAOYSA-N 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MNBKLUUYKPBKDU-BBECNAHFSA-N palmitoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MNBKLUUYKPBKDU-BBECNAHFSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000004999 plastisol Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010972 statistical evaluation Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- KRVFDQLWSXYEOD-UHFFFAOYSA-N tetraethyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CCOC(=O)C1CC(C(=O)OCC)C(C(=O)OCC)CC1C(=O)OCC KRVFDQLWSXYEOD-UHFFFAOYSA-N 0.000 description 1
- WXORPFRDBYGNKY-UHFFFAOYSA-N tetramethyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound COC(=O)C1CC(C(=O)OC)C(C(=O)OC)CC1C(=O)OC WXORPFRDBYGNKY-UHFFFAOYSA-N 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- VWZLPQHRYOBKKQ-UHFFFAOYSA-N tributyl cyclohexane-1,2,3-tricarboxylate Chemical compound CCCCOC(=O)C1CCCC(C(=O)OCCCC)C1C(=O)OCCCC VWZLPQHRYOBKKQ-UHFFFAOYSA-N 0.000 description 1
- SAZDPSCWSFPDIX-UHFFFAOYSA-N tricyclohexyl cyclohexane-1,2,4-tricarboxylate Chemical compound C1CC(C(=O)OC2CCCCC2)C(C(=O)OC2CCCCC2)CC1C(=O)OC1CCCCC1 SAZDPSCWSFPDIX-UHFFFAOYSA-N 0.000 description 1
- BDYMDXVDZRBZIN-UHFFFAOYSA-N tricyclohexyl cyclohexane-1,3,5-tricarboxylate Chemical compound C1C(C(=O)OC2CCCCC2)CC(C(=O)OC2CCCCC2)CC1C(=O)OC1CCCCC1 BDYMDXVDZRBZIN-UHFFFAOYSA-N 0.000 description 1
- FLBJTLYDTXXCFH-UHFFFAOYSA-N triicosyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCCCCCCCCCCC)C1 FLBJTLYDTXXCFH-UHFFFAOYSA-N 0.000 description 1
- ZZNOMLSSCRBRJS-UHFFFAOYSA-N trimethyl cyclohexane-1,3,5-tricarboxylate Chemical compound COC(=O)C1CC(C(=O)OC)CC(C(=O)OC)C1 ZZNOMLSSCRBRJS-UHFFFAOYSA-N 0.000 description 1
- PBJWDMQGPRUJSJ-UHFFFAOYSA-N trioctadecyl cyclohexane-1,2,3-tricarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCCCCCCCCCCC)C1C(=O)OCCCCCCCCCCCCCCCCCC PBJWDMQGPRUJSJ-UHFFFAOYSA-N 0.000 description 1
- ZWPZLIAOPPNGFL-UHFFFAOYSA-N trioctyl cyclohexane-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCC)C1C(=O)OCCCCCCCC ZWPZLIAOPPNGFL-UHFFFAOYSA-N 0.000 description 1
- DMNWRCNEYDIESS-UHFFFAOYSA-N tripropyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCCOC(=O)C1CCC(C(=O)OCCC)C(C(=O)OCCC)C1 DMNWRCNEYDIESS-UHFFFAOYSA-N 0.000 description 1
- QBKXEBIQYCSZSZ-UHFFFAOYSA-N tris(2-methylpropyl) cyclohexane-1,2,4-tricarboxylate Chemical compound CC(C)COC(=O)C1CCC(C(=O)OCC(C)C)C(C(=O)OCC(C)C)C1 QBKXEBIQYCSZSZ-UHFFFAOYSA-N 0.000 description 1
- QGQWCWAEXXADQC-UHFFFAOYSA-N tris(2-methylpropyl) cyclohexane-1,3,5-tricarboxylate Chemical compound CC(C)COC(=O)C1CC(C(=O)OCC(C)C)CC(C(=O)OCC(C)C)C1 QGQWCWAEXXADQC-UHFFFAOYSA-N 0.000 description 1
- WFGQIWOAMQBBEH-UHFFFAOYSA-N tris(6-methylheptyl) cyclohexane-1,2,3-tricarboxylate Chemical compound CC(C)CCCCCOC(=O)C1CCCC(C(=O)OCCCCCC(C)C)C1C(=O)OCCCCCC(C)C WFGQIWOAMQBBEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
- C07C61/09—Completely hydrogenated benzenedicarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fodder In General (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19927977A DE19927977A1 (de) | 1999-06-18 | 1999-06-18 | Verwendung von Cyclohexanpolycarbonsäuren als Weichmacher zur Herstellung toxikologisch günstig zu bewertender Kunststoffe |
| PCT/EP2000/005609 WO2000078853A1 (de) | 1999-06-18 | 2000-06-16 | Verwendung von cyclohexanpolycarbonsäuren als weichmacher zur herstellung toxikologisch günstig zu bewertender kunststoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA01012835A true MXPA01012835A (es) | 2002-07-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA01012835A MXPA01012835A (es) | 1999-06-18 | 2000-06-16 | Uso de los acidos ciclohexanopolicarboxilicos como plastificantes para preparar plasticos clasificados como favorables toxicologicamente. |
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|---|---|
| EP (1) | EP1192212B1 (enExample) |
| JP (1) | JP2003503526A (enExample) |
| KR (1) | KR100670079B1 (enExample) |
| CN (1) | CN1221601C (enExample) |
| AT (1) | ATE315060T1 (enExample) |
| AU (1) | AU5974600A (enExample) |
| BR (1) | BR0011716A (enExample) |
| CA (1) | CA2376742A1 (enExample) |
| DE (2) | DE19927977A1 (enExample) |
| DK (1) | DK1192212T3 (enExample) |
| ES (1) | ES2254196T3 (enExample) |
| MX (1) | MXPA01012835A (enExample) |
| MY (1) | MY151162A (enExample) |
| NO (1) | NO333555B1 (enExample) |
| PL (1) | PL200275B1 (enExample) |
| PT (1) | PT1192212E (enExample) |
| TW (1) | TWI266784B (enExample) |
| WO (1) | WO2000078853A1 (enExample) |
| ZA (1) | ZA200110300B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP4898079B2 (ja) * | 2001-02-16 | 2012-03-14 | ビーエーエスエフ ソシエタス・ヨーロピア | シクロヘキサンジカルボン酸およびその誘導体を製造する方法 |
| DE10129129C1 (de) * | 2001-06-16 | 2002-12-05 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von Cyclohexandicarbonsäureestern |
| ES2318049T3 (es) | 2001-09-25 | 2009-05-01 | Exxonmobil Chemical Patents Inc. | Poli(cloruro de vinilo) plastificado. |
| DE10239737A1 (de) * | 2002-08-29 | 2004-03-18 | Rehau Ag + Co. | Medizinische Arbeitsmittel |
| ES2623384T5 (es) | 2003-03-14 | 2020-08-31 | Basf Se | Tintas para impresión con derivados de ácidos ciclohexanopolicarboxílicos |
| DE102004029732A1 (de) | 2004-06-21 | 2006-01-19 | Basf Ag | Hilfsmittel enthaltend Cyclohexanpolycarbonsäurederivate |
| JP4843999B2 (ja) * | 2005-04-28 | 2011-12-21 | 新日本理化株式会社 | 脂環族二価アルコールエステル |
| US20100028528A1 (en) | 2006-12-19 | 2010-02-04 | Basf Se | Use of cyclohexane polycarbonic acid esters for the production of coating materials for the coil coating method and the production of coated coils |
| DE102007037795A1 (de) | 2007-08-10 | 2009-02-12 | Nabaltec Ag | Stabilisatorsysteme für halogenhaltige Polymere |
| DE102008018872A1 (de) | 2008-04-14 | 2009-10-15 | Ika Innovative Kunststoffaufbereitung Gmbh & Co. Kg | Stabilisatorsystem für halogenhaltige Polymere |
| DE102008020203A1 (de) | 2008-04-22 | 2009-10-29 | Catena Additives Gmbh & Co. Kg | Lösemittelfreie High Solids (One-Pack)-Stabilisatoren für halogenhaltige Polymere |
| DE102009045701A1 (de) | 2009-10-14 | 2011-04-21 | Ika Innovative Kunststoffaufbereitung Gmbh & Co. Kg | Stabilisator-Kombinationen für halogenhaltige Polymere |
| WO2011054781A1 (de) | 2009-11-03 | 2011-05-12 | Basf Se | THERMOPLASTISCHE ZUSAMMENSETZUNGEN MIT VERBESSERTER FLIEßFÄHIGKEIT |
| DE102010011191A1 (de) | 2010-03-11 | 2011-09-15 | Ika Innovative Kunststoffaufbereitung Gmbh & Co. Kg | Stabilisatormischungen für halogenhaltige Kunststoffe durch Unterwassergranulierung |
| DE102010020486A1 (de) | 2010-05-14 | 2011-11-17 | Catena Additives Gmbh & Co. Kg | Flammgeschützte halogenhaltige Polymere mit verbesserter Thermostabilität |
| CN101962461B (zh) * | 2010-10-25 | 2015-05-06 | 欧阳伟 | 不含邻苯二甲酸酯的医用聚氯乙烯塑料 |
| CN101962460A (zh) * | 2010-10-25 | 2011-02-02 | 欧阳伟 | 耐辐照不含邻苯二甲酸酯的医用聚氯乙烯塑料 |
| KR101264148B1 (ko) * | 2011-01-18 | 2013-05-14 | 한화케미칼 주식회사 | 디에틸헥실사이클로헥산을 포함하는 벽지용 염화비닐계 수지 조성물 |
| DE102012001979A1 (de) | 2012-02-02 | 2013-08-08 | Voco Gmbh | Härtbares Gemisch umfassend Weichmacher mit einem polyalicyclischen Strukturelement zur Anwendung bei der Herstellung dentaler Werkstoffe |
| DE102012001978A1 (de) | 2012-02-02 | 2013-08-08 | Voco Gmbh | Dentale Kompositmaterialien enthaltend tricyclische Weichmacher |
| FR2990210B1 (fr) | 2012-05-03 | 2014-05-02 | Roquette Freres | Compositions plastifiantes comprenant des accelerateurs de gelification a base d'ester de 1,4 : 3,6-dianhydrohexitol de faible poids molaire |
| FR2998569B1 (fr) | 2012-11-26 | 2015-01-09 | Roquette Freres | Procede de fabrication de compositions de diesters de 1,4 : 3,6-dianhydrohexitol |
| FR3024735B1 (fr) | 2014-08-07 | 2016-08-26 | Roquette Freres | Composition plastifiante liquide |
| JP6425460B2 (ja) * | 2014-08-27 | 2018-11-21 | リケンテクノス株式会社 | 塩化ビニル系樹脂組成物 |
| JP2016074876A (ja) * | 2014-10-08 | 2016-05-12 | 新日本理化株式会社 | １，４−シクロヘキサンジカルボン酸ジエステルからなる塩化ビニル系樹脂用可塑剤 |
| PL3147317T3 (pl) * | 2015-09-28 | 2018-01-31 | Evonik Degussa Gmbh | Estry tripentylowe kwasu trimelitowego |
| HUE051339T2 (hu) * | 2016-03-18 | 2021-03-01 | Nouryon Chemicals Int Bv | Tárolásstabil vizes szerves peroxid emulziók |
| KR102260895B1 (ko) | 2018-06-12 | 2021-06-07 | 주식회사 엘지화학 | 가소제 조성물 및 이를 포함하는 수지 조성물 |
| EP3875526B1 (en) * | 2018-10-29 | 2022-10-19 | Lg Chem, Ltd. | Cyclohexane triester-based plasticizer composition, and resin composition comprising the same |
| KR102120301B1 (ko) | 2018-10-30 | 2020-06-08 | 상명대학교산학협력단 | 티몰 에스터계 유도체 화합물, 이의 제조 방법 및 이의 용도 |
| KR102122003B1 (ko) | 2018-11-26 | 2020-06-11 | 상명대학교산학협력단 | 스크린 타입의 노보난 유도체 화합물, 이의 제조 방법 및 이의 용도 |
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|---|---|---|---|---|
| US2070770A (en) * | 1935-10-18 | 1937-02-16 | Du Pont | Hydrogenation of alkyl phthalates |
| US3308086A (en) * | 1963-08-30 | 1967-03-07 | Union Carbide Corp | Ethylene copolymers with vinyl esters plasticized with phosphate and carboxylic esters |
| US3444237A (en) * | 1966-03-23 | 1969-05-13 | Grace W R & Co | Esters of cyclohexane-1,2,4-tricarboxylic acid |
| DE2823165A1 (de) * | 1978-05-26 | 1979-11-29 | Bayer Ag | Verfahren zur herstellung von cycloaliphatischen carbonsaeureestern |
| JPS58222136A (ja) * | 1982-06-18 | 1983-12-23 | New Japan Chem Co Ltd | 高重合度塩化ビニル系樹脂組成物 |
| JP3331673B2 (ja) * | 1993-04-23 | 2002-10-07 | 新日本理化株式会社 | 環状ポリオレフィン系樹脂組成物 |
| JP3456226B2 (ja) * | 1993-06-24 | 2003-10-14 | 新日本理化株式会社 | ポリオレフィン系樹脂組成物 |
| JP3401888B2 (ja) * | 1993-12-20 | 2003-04-28 | 新日本理化株式会社 | ポリオレフィン系樹脂組成物 |
| US5977223A (en) * | 1997-12-12 | 1999-11-02 | Ansell Healthcare Products, Inc. | Elastomeric articles |
| ES2199484T3 (es) * | 1997-12-19 | 2004-02-16 | Basf Aktiengesellschaft | Procedimiento para la hidrogenacion de acidos bencenopolicarboxilicos o derivados de estos utilizando un catalizador con macroporos. |
| JP2000053874A (ja) * | 1998-03-31 | 2000-02-22 | Daicel Chem Ind Ltd | 熱可塑性樹脂組成物、水性組成物、感熱性粘着剤及び感熱性粘着シ―ト |
-
1999
- 1999-06-18 DE DE19927977A patent/DE19927977A1/de not_active Ceased
-
2000
- 2000-06-16 JP JP2001505607A patent/JP2003503526A/ja active Pending
- 2000-06-16 PT PT00945771T patent/PT1192212E/pt unknown
- 2000-06-16 MX MXPA01012835A patent/MXPA01012835A/es active IP Right Grant
- 2000-06-16 AT AT00945771T patent/ATE315060T1/de active
- 2000-06-16 ES ES00945771T patent/ES2254196T3/es not_active Expired - Lifetime
- 2000-06-16 AU AU59746/00A patent/AU5974600A/en not_active Abandoned
- 2000-06-16 WO PCT/EP2000/005609 patent/WO2000078853A1/de not_active Ceased
- 2000-06-16 DE DE50012023T patent/DE50012023D1/de not_active Expired - Lifetime
- 2000-06-16 CA CA002376742A patent/CA2376742A1/en not_active Abandoned
- 2000-06-16 BR BR0011716-1A patent/BR0011716A/pt not_active Application Discontinuation
- 2000-06-16 MY MYPI20002722 patent/MY151162A/en unknown
- 2000-06-16 PL PL352273A patent/PL200275B1/pl unknown
- 2000-06-16 KR KR1020017016243A patent/KR100670079B1/ko not_active Expired - Fee Related
- 2000-06-16 CN CNB008091536A patent/CN1221601C/zh not_active Expired - Fee Related
- 2000-06-16 DK DK00945771T patent/DK1192212T3/da active
- 2000-06-16 EP EP00945771A patent/EP1192212B1/de not_active Revoked
- 2000-06-17 TW TW089111917A patent/TWI266784B/zh not_active IP Right Cessation
-
2001
- 2001-12-14 ZA ZA200110300A patent/ZA200110300B/en unknown
- 2001-12-17 NO NO20016148A patent/NO333555B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20016148L (no) | 2002-01-16 |
| JP2003503526A (ja) | 2003-01-28 |
| ATE315060T1 (de) | 2006-02-15 |
| CA2376742A1 (en) | 2000-12-28 |
| BR0011716A (pt) | 2002-03-05 |
| PL352273A1 (en) | 2003-08-11 |
| NO333555B1 (no) | 2013-07-08 |
| CN1357024A (zh) | 2002-07-03 |
| MY151162A (en) | 2014-04-30 |
| CN1221601C (zh) | 2005-10-05 |
| NO20016148D0 (no) | 2001-12-17 |
| PT1192212E (pt) | 2006-05-31 |
| DE50012023D1 (de) | 2006-03-30 |
| WO2000078853A1 (de) | 2000-12-28 |
| PL200275B1 (pl) | 2008-12-31 |
| AU5974600A (en) | 2001-01-09 |
| EP1192212B1 (de) | 2006-01-04 |
| KR20020019095A (ko) | 2002-03-09 |
| DK1192212T3 (da) | 2006-03-27 |
| ES2254196T3 (es) | 2006-06-16 |
| ZA200110300B (en) | 2003-02-26 |
| EP1192212A1 (de) | 2002-04-03 |
| DE19927977A1 (de) | 2000-12-21 |
| KR100670079B1 (ko) | 2007-01-17 |
| TWI266784B (en) | 2006-11-21 |
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