ZA200110300B - Use of cyclohexane polycarboxylic acids as plasticizers in the production of plastics which are rated toxicologically favourable. - Google Patents
Use of cyclohexane polycarboxylic acids as plasticizers in the production of plastics which are rated toxicologically favourable. Download PDFInfo
- Publication number
- ZA200110300B ZA200110300B ZA200110300A ZA200110300A ZA200110300B ZA 200110300 B ZA200110300 B ZA 200110300B ZA 200110300 A ZA200110300 A ZA 200110300A ZA 200110300 A ZA200110300 A ZA 200110300A ZA 200110300 B ZA200110300 B ZA 200110300B
- Authority
- ZA
- South Africa
- Prior art keywords
- ester
- cyclohexane
- acid
- hydrogenating
- cas
- Prior art date
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- 239000002253 acid Substances 0.000 title claims abstract description 31
- 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 17
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title abstract 3
- 230000002349 favourable effect Effects 0.000 title abstract 2
- 210000004185 liver Anatomy 0.000 claims abstract description 22
- 241001465754 Metazoa Species 0.000 claims abstract description 14
- 230000037396 body weight Effects 0.000 claims abstract description 12
- 230000000694 effects Effects 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 108010008746 palmitoyl CoA oxidase Proteins 0.000 claims abstract description 12
- 102100026798 Peroxisomal acyl-coenzyme A oxidase 1 Human genes 0.000 claims abstract description 11
- 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 44
- -1 isodecyl Chemical group 0.000 claims description 17
- 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
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 12
- 125000005498 phthalate group Chemical class 0.000 claims description 10
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 claims description 8
- 210000002784 stomach Anatomy 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 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 6
- 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 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 claims description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 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
- FTQQZEVRNWXZBS-UHFFFAOYSA-N bis(3-methylbutyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCOC(=O)C1CCCCC1C(=O)OCCC(C)C FTQQZEVRNWXZBS-UHFFFAOYSA-N 0.000 claims description 2
- NSRZVPYAJXTHBK-UHFFFAOYSA-N bis(5-methylhexyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCOC(=O)C1CCCCC1C(=O)OCCCCC(C)C NSRZVPYAJXTHBK-UHFFFAOYSA-N 0.000 claims description 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 4
- 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 4
- 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
- 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
- 239000004808 2-ethylhexylester Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 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 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 7
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 6
- 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 6
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 3
- 210000002824 peroxisome Anatomy 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 238000001061 Dunnett's test Methods 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 206010019695 Hepatic neoplasm Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241000700157 Rattus norvegicus Species 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
- 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
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- AFWGXDCDOCBMST-UHFFFAOYSA-N tetrakis(10-methylundecyl) cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CC(C)CCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCC(C)C)C(C(=O)OCCCCCCCCCC(C)C)CC1C(=O)OCCCCCCCCCC(C)C AFWGXDCDOCBMST-UHFFFAOYSA-N 0.000 description 2
- 231100000723 toxicological property Toxicity 0.000 description 2
- UQTSMEVFQYOVKB-UHFFFAOYSA-N tris(10-methylundecyl) cyclohexane-1,3,5-tricarboxylate Chemical compound CC(C)CCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCC(C)C)CC(C(=O)OCCCCCCCCCC(C)C)C1 UQTSMEVFQYOVKB-UHFFFAOYSA-N 0.000 description 2
- BKUSIKGSPSFQAC-RRKCRQDMSA-N 2'-deoxyinosine-5'-diphosphate Chemical compound O1[C@H](CO[P@@](O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(NC=NC2=O)=C2N=C1 BKUSIKGSPSFQAC-RRKCRQDMSA-N 0.000 description 1
- VHBBGWSGNBOYKG-UHFFFAOYSA-N 2,3-bis(10-methylundecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCCCCC(C)C VHBBGWSGNBOYKG-UHFFFAOYSA-N 0.000 description 1
- HHARKBWEDVCNIB-UHFFFAOYSA-N 2,3-bis(16-methylheptadecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCCCCCCCCCCC(C)C HHARKBWEDVCNIB-UHFFFAOYSA-N 0.000 description 1
- VCKGOKRLQMHJAW-UHFFFAOYSA-N 2,3-bis(2-methylpropoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)COC(=O)C1CCCC(C(O)=O)C1C(=O)OCC(C)C VCKGOKRLQMHJAW-UHFFFAOYSA-N 0.000 description 1
- NZEQOAZHSWGFNI-UHFFFAOYSA-N 2,3-bis(6-methylheptoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCC(C)C NZEQOAZHSWGFNI-UHFFFAOYSA-N 0.000 description 1
- DTZGZYPRNCBXKB-UHFFFAOYSA-N 2,3-bis(7-methyloctoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCC(C)C DTZGZYPRNCBXKB-UHFFFAOYSA-N 0.000 description 1
- XIZMZRIEXDJMRZ-UHFFFAOYSA-N 2,3-bis(8-methylnonoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCCC(C)C XIZMZRIEXDJMRZ-UHFFFAOYSA-N 0.000 description 1
- KIDXIFHPAFUXNU-UHFFFAOYSA-N 2,3-bis(butoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCC KIDXIFHPAFUXNU-UHFFFAOYSA-N 0.000 description 1
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- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 1
- GGLHXZYMYYBBHT-UHFFFAOYSA-N dinonyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCC GGLHXZYMYYBBHT-UHFFFAOYSA-N 0.000 description 1
- GVMYLYVIHYDFAT-UHFFFAOYSA-N dinonyl cyclohexane-1,3-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCC)C1 GVMYLYVIHYDFAT-UHFFFAOYSA-N 0.000 description 1
- IMMQUIWLYCDDQF-UHFFFAOYSA-N dinonyl cyclohexane-1,4-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCC)CC1 IMMQUIWLYCDDQF-UHFFFAOYSA-N 0.000 description 1
- UVRWLQXFVJTBMI-UHFFFAOYSA-N dioctadecyl cyclohexane-1,3-dicarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCCCCCCCCCCC)C1 UVRWLQXFVJTBMI-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
- BYGQIUHOWVUUPS-UHFFFAOYSA-N dioctyl cyclohexane-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCC)CC1 BYGQIUHOWVUUPS-UHFFFAOYSA-N 0.000 description 1
- GYKCZEHCUMJVKP-UHFFFAOYSA-N dipropyl cyclohexane-1,3-dicarboxylate Chemical compound CCCOC(=O)C1CCCC(C(=O)OCCC)C1 GYKCZEHCUMJVKP-UHFFFAOYSA-N 0.000 description 1
- YTZVKGLPOSQCML-UHFFFAOYSA-N dipropyl cyclohexane-1,4-dicarboxylate Chemical compound CCCOC(=O)C1CCC(C(=O)OCCC)CC1 YTZVKGLPOSQCML-UHFFFAOYSA-N 0.000 description 1
- AYCHZURENQEYAC-UHFFFAOYSA-N ditert-butyl cyclohexane-1,2-dicarboxylate Chemical compound CC(C)(C)OC(=O)C1CCCCC1C(=O)OC(C)(C)C AYCHZURENQEYAC-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
- DXOQACHRVLHPJR-UHFFFAOYSA-N ditert-butyl cyclohexane-1,4-dicarboxylate Chemical compound CC(C)(C)OC(=O)C1CCC(C(=O)OC(C)(C)C)CC1 DXOQACHRVLHPJR-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
- 229940047127 fiore Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 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 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003614 peroxisome proliferator Substances 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
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 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
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- GXRDPADRHDCAIM-UHFFFAOYSA-N tetracyclohexyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound C1C(C(=O)OC2CCCCC2)C(C(=O)OC2CCCCC2)CC(C(=O)OC2CCCCC2)C1C(=O)OC1CCCCC1 GXRDPADRHDCAIM-UHFFFAOYSA-N 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
- VYTKEEUJOWOOSF-UHFFFAOYSA-N tetraicosyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCCCCCCCCCCC)CC1C(=O)OCCCCCCCCCCCCCCCCCCCC VYTKEEUJOWOOSF-UHFFFAOYSA-N 0.000 description 1
- DWZVENSAZJKQFM-UHFFFAOYSA-N tetrakis(16-methylheptadecyl) cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCC(C)C)C(C(=O)OCCCCCCCCCCCCCCCC(C)C)CC1C(=O)OCCCCCCCCCCCCCCCC(C)C DWZVENSAZJKQFM-UHFFFAOYSA-N 0.000 description 1
- JYKJHYKJAYVHBS-UHFFFAOYSA-N tetrakis(2-methylpropyl) cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CC(C)COC(=O)C1CC(C(=O)OCC(C)C)C(C(=O)OCC(C)C)CC1C(=O)OCC(C)C JYKJHYKJAYVHBS-UHFFFAOYSA-N 0.000 description 1
- JTFPPBXXDGNMPE-UHFFFAOYSA-N tetrakis(6-methylheptyl) cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CC(C)CCCCCOC(=O)C1CC(C(=O)OCCCCCC(C)C)C(C(=O)OCCCCCC(C)C)CC1C(=O)OCCCCCC(C)C JTFPPBXXDGNMPE-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
- KDDLKHSVSTWKEN-UHFFFAOYSA-N tetranonyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCC)C(C(=O)OCCCCCCCCC)CC1C(=O)OCCCCCCCCC KDDLKHSVSTWKEN-UHFFFAOYSA-N 0.000 description 1
- PEIAXIJPJBHEGG-UHFFFAOYSA-N tetraoctadecyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCCCCCCCCC)CC1C(=O)OCCCCCCCCCCCCCCCCCC PEIAXIJPJBHEGG-UHFFFAOYSA-N 0.000 description 1
- BWFORYPESBGYPY-UHFFFAOYSA-N tetraoctyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)CC1C(=O)OCCCCCCCC BWFORYPESBGYPY-UHFFFAOYSA-N 0.000 description 1
- RJPGHOMHFZXMFB-UHFFFAOYSA-N tetrapropyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CCCOC(=O)C1CC(C(=O)OCCC)C(C(=O)OCCC)CC1C(=O)OCCC RJPGHOMHFZXMFB-UHFFFAOYSA-N 0.000 description 1
- VOABMBHHZYPUEU-UHFFFAOYSA-N tetratert-butyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CC(C)(C)OC(=O)C1CC(C(=O)OC(C)(C)C)C(C(=O)OC(C)(C)C)CC1C(=O)OC(C)(C)C VOABMBHHZYPUEU-UHFFFAOYSA-N 0.000 description 1
- JPPURJZDMNFVMH-UHFFFAOYSA-N tetraundecyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCC)CC1C(=O)OCCCCCCCCCCC JPPURJZDMNFVMH-UHFFFAOYSA-N 0.000 description 1
- 231100000027 toxicology 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
- HUTIXMKLGMBSPG-UHFFFAOYSA-N tributyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCCCOC(=O)C1CCC(C(=O)OCCCC)C(C(=O)OCCCC)C1 HUTIXMKLGMBSPG-UHFFFAOYSA-N 0.000 description 1
- NENGEDRGOSOOOW-UHFFFAOYSA-N tributyl cyclohexane-1,3,5-tricarboxylate Chemical compound CCCCOC(=O)C1CC(C(=O)OCCCC)CC(C(=O)OCCCC)C1 NENGEDRGOSOOOW-UHFFFAOYSA-N 0.000 description 1
- SFSXHKUSUUFQRY-UHFFFAOYSA-N tricyclohexyl cyclohexane-1,2,3-tricarboxylate Chemical compound C1CCC(C(=O)OC2CCCCC2)C(C(=O)OC2CCCCC2)C1C(=O)OC1CCCCC1 SFSXHKUSUUFQRY-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
- NSXIVTVTODNMKD-UHFFFAOYSA-N triethyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCOC(=O)C1CCC(C(=O)OCC)C(C(=O)OCC)C1 NSXIVTVTODNMKD-UHFFFAOYSA-N 0.000 description 1
- JQFXPGZFIFHJJV-UHFFFAOYSA-N triethyl cyclohexane-1,3,5-tricarboxylate Chemical compound CCOC(=O)C1CC(C(=O)OCC)CC(C(=O)OCC)C1 JQFXPGZFIFHJJV-UHFFFAOYSA-N 0.000 description 1
- HSCSZOOSAZOXRP-UHFFFAOYSA-N triicosyl cyclohexane-1,2,3-tricarboxylate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCCCCCCCCCCCCC)C1C(=O)OCCCCCCCCCCCCCCCCCCCC HSCSZOOSAZOXRP-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
- JQYIZTNNWSYZRG-UHFFFAOYSA-N triicosyl cyclohexane-1,3,5-tricarboxylate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCCCCCC)CC(C(=O)OCCCCCCCCCCCCCCCCCCCC)C1 JQYIZTNNWSYZRG-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
- WXLPYXOKSSFKFY-UHFFFAOYSA-N trinonyl cyclohexane-1,2,3-tricarboxylate Chemical compound CCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCC)C1C(=O)OCCCCCCCCC WXLPYXOKSSFKFY-UHFFFAOYSA-N 0.000 description 1
- CAMRDYLPCOAKSW-UHFFFAOYSA-N trinonyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCC)C(C(=O)OCCCCCCCCC)C1 CAMRDYLPCOAKSW-UHFFFAOYSA-N 0.000 description 1
- BZSAOSAGYPAACU-UHFFFAOYSA-N trinonyl cyclohexane-1,3,5-tricarboxylate Chemical compound CCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCC)CC(C(=O)OCCCCCCCCC)C1 BZSAOSAGYPAACU-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
- GEXPEVRJFRUVKT-UHFFFAOYSA-N trioctadecyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCCCCCCCCC)C1 GEXPEVRJFRUVKT-UHFFFAOYSA-N 0.000 description 1
- KWYDKNXKDJHBAE-UHFFFAOYSA-N trioctadecyl cyclohexane-1,3,5-tricarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCCCC)CC(C(=O)OCCCCCCCCCCCCCCCCCC)C1 KWYDKNXKDJHBAE-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
- WMZUMIKGVXZUJR-UHFFFAOYSA-N trioctyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)C1 WMZUMIKGVXZUJR-UHFFFAOYSA-N 0.000 description 1
- CZRYHSDJIFNQJP-UHFFFAOYSA-N trioctyl cyclohexane-1,3,5-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCC)CC(C(=O)OCCCCCCCC)C1 CZRYHSDJIFNQJP-UHFFFAOYSA-N 0.000 description 1
- LVDYPXGFTXRKAV-UHFFFAOYSA-N tripropyl cyclohexane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)C1CCCC(C(=O)OCCC)C1C(=O)OCCC LVDYPXGFTXRKAV-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
- IZACYUDSRVGIGQ-UHFFFAOYSA-N tripropyl cyclohexane-1,3,5-tricarboxylate Chemical compound CCCOC(=O)C1CC(C(=O)OCCC)CC(C(=O)OCCC)C1 IZACYUDSRVGIGQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BECNIVFTJQEMIV-UHFFFAOYSA-N tris(16-methylheptadecyl) cyclohexane-1,2,3-tricarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCCCCCCCCC(C)C)C1C(=O)OCCCCCCCCCCCCCCCC(C)C BECNIVFTJQEMIV-UHFFFAOYSA-N 0.000 description 1
- RCDSKPRFZVRJEP-UHFFFAOYSA-N tris(16-methylheptadecyl) cyclohexane-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCCCCCCCC(C)C)C(C(=O)OCCCCCCCCCCCCCCCC(C)C)C1 RCDSKPRFZVRJEP-UHFFFAOYSA-N 0.000 description 1
- VTTPBWWRZXHFEI-UHFFFAOYSA-N tris(16-methylheptadecyl) cyclohexane-1,3,5-tricarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCC(C)C)CC(C(=O)OCCCCCCCCCCCCCCCC(C)C)C1 VTTPBWWRZXHFEI-UHFFFAOYSA-N 0.000 description 1
- HOBBPZKHYWLHFT-UHFFFAOYSA-N tris(2-methylpropyl) cyclohexane-1,2,3-tricarboxylate Chemical compound CC(C)COC(=O)C1CCCC(C(=O)OCC(C)C)C1C(=O)OCC(C)C HOBBPZKHYWLHFT-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
- XPDFJVCVDRXYJN-UHFFFAOYSA-N tris(6-methylheptyl) cyclohexane-1,3,5-tricarboxylate Chemical compound CC(C)CCCCCOC(=O)C1CC(C(=O)OCCCCCC(C)C)CC(C(=O)OCCCCCC(C)C)C1 XPDFJVCVDRXYJN-UHFFFAOYSA-N 0.000 description 1
- CERWWLRAZNQAGX-UHFFFAOYSA-N tritert-butyl cyclohexane-1,2,3-tricarboxylate Chemical compound CC(C)(C)OC(=O)C1CCCC(C(=O)OC(C)(C)C)C1C(=O)OC(C)(C)C CERWWLRAZNQAGX-UHFFFAOYSA-N 0.000 description 1
- KTQJPTTXTMATKF-UHFFFAOYSA-N tritert-butyl cyclohexane-1,2,4-tricarboxylate Chemical compound CC(C)(C)OC(=O)C1CCC(C(=O)OC(C)(C)C)C(C(=O)OC(C)(C)C)C1 KTQJPTTXTMATKF-UHFFFAOYSA-N 0.000 description 1
- YWSNZWUWRXCWEU-UHFFFAOYSA-N tritert-butyl cyclohexane-1,3,5-tricarboxylate Chemical compound CC(C)(C)OC(=O)C1CC(C(=O)OC(C)(C)C)CC(C(=O)OC(C)(C)C)C1 YWSNZWUWRXCWEU-UHFFFAOYSA-N 0.000 description 1
- MTIYROBVDLLQRS-UHFFFAOYSA-N triundecyl cyclohexane-1,2,3-tricarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1CCCC(C(=O)OCCCCCCCCCCC)C1C(=O)OCCCCCCCCCCC MTIYROBVDLLQRS-UHFFFAOYSA-N 0.000 description 1
- HDYWDORHSIRFCL-UHFFFAOYSA-N triundecyl cyclohexane-1,2,4-tricarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCC)C1 HDYWDORHSIRFCL-UHFFFAOYSA-N 0.000 description 1
- DWXSUXXHEHSYLG-UHFFFAOYSA-N triundecyl cyclohexane-1,3,5-tricarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCC)CC(C(=O)OCCCCCCCCCCC)C1 DWXSUXXHEHSYLG-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)
- Materials For Medical Uses (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200110300B true ZA200110300B (en) | 2003-02-26 |
Family
ID=7911754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200110300A ZA200110300B (en) | 1999-06-18 | 2001-12-14 | Use of cyclohexane polycarboxylic acids as plasticizers in the production of plastics which are rated toxicologically favourable. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1192212B1 (da) |
| JP (1) | JP2003503526A (da) |
| KR (1) | KR100670079B1 (da) |
| CN (1) | CN1221601C (da) |
| AT (1) | ATE315060T1 (da) |
| AU (1) | AU5974600A (da) |
| BR (1) | BR0011716A (da) |
| CA (1) | CA2376742A1 (da) |
| DE (2) | DE19927977A1 (da) |
| DK (1) | DK1192212T3 (da) |
| ES (1) | ES2254196T3 (da) |
| MX (1) | MXPA01012835A (da) |
| MY (1) | MY151162A (da) |
| NO (1) | NO333555B1 (da) |
| PL (1) | PL200275B1 (da) |
| PT (1) | PT1192212E (da) |
| TW (1) | TWI266784B (da) |
| WO (1) | WO2000078853A1 (da) |
| ZA (1) | ZA200110300B (da) |
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|---|---|---|---|---|
| CN101024705B (zh) * | 2001-02-16 | 2012-06-20 | 巴斯福股份公司 | 环己烷二羧酸及其衍生物的制备方法 |
| DE10129129C1 (de) * | 2001-06-16 | 2002-12-05 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von Cyclohexandicarbonsäureestern |
| CN1558927A (zh) | 2001-09-25 | 2004-12-29 | ����ɭ���ڻ�ѧר����˾ | 增塑聚氯乙烯 |
| DE10239737A1 (de) * | 2002-08-29 | 2004-03-18 | Rehau Ag + Co. | Medizinische Arbeitsmittel |
| MXPA05009597A (es) | 2003-03-14 | 2006-03-21 | Basf Ag | Tintas de impresion que comprenden derivados de acido ciclohexanpolicarboxilico. |
| 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 |
| WO2008074594A1 (de) | 2006-12-19 | 2008-06-26 | Basf Se | Verwendung von cyclohexanpolycarbonsäureestern für die herstellung von beschichtungsstoffen für das coil-coating-verfahren und von beschichteten 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 |
| EP2496637B1 (de) | 2009-11-03 | 2015-10-07 | Styrolution Europe GmbH | 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 |
| DE102012001978A1 (de) | 2012-02-02 | 2013-08-08 | Voco Gmbh | Dentale Kompositmaterialien enthaltend tricyclische Weichmacher |
| 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 |
| 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 |
| SI3147317T1 (en) * | 2015-09-28 | 2018-01-31 | Evonik Degussa Gmbh | Tripentylester trimellitic acid |
| JP6698172B2 (ja) * | 2016-03-18 | 2020-05-27 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップＮｏｕｒｙｏｎ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 貯蔵安定性のある水性有機過酸化物エマルション |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| KR100688403B1 (ko) * | 1997-12-19 | 2007-03-09 | 바스프 악티엔게젤샤프트 | 매크로포어를 함유하는 촉매를 사용하는 벤젠폴리카르복실산 또는 그의 유도체의 수소화 방법 |
| 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 MX MXPA01012835A patent/MXPA01012835A/es active IP Right Grant
- 2000-06-16 ES ES00945771T patent/ES2254196T3/es not_active Expired - Lifetime
- 2000-06-16 PL PL352273A patent/PL200275B1/pl unknown
- 2000-06-16 JP JP2001505607A patent/JP2003503526A/ja active Pending
- 2000-06-16 EP EP00945771A patent/EP1192212B1/de not_active Revoked
- 2000-06-16 DK DK00945771T patent/DK1192212T3/da active
- 2000-06-16 WO PCT/EP2000/005609 patent/WO2000078853A1/de active Search and Examination
- 2000-06-16 KR KR1020017016243A patent/KR100670079B1/ko not_active IP Right Cessation
- 2000-06-16 DE DE50012023T patent/DE50012023D1/de not_active Expired - Lifetime
- 2000-06-16 MY MYPI20002722 patent/MY151162A/en unknown
- 2000-06-16 AU AU59746/00A patent/AU5974600A/en not_active Abandoned
- 2000-06-16 AT AT00945771T patent/ATE315060T1/de active
- 2000-06-16 BR BR0011716-1A patent/BR0011716A/pt not_active Application Discontinuation
- 2000-06-16 CN CNB008091536A patent/CN1221601C/zh not_active Expired - Fee Related
- 2000-06-16 CA CA002376742A patent/CA2376742A1/en not_active Abandoned
- 2000-06-16 PT PT00945771T patent/PT1192212E/pt unknown
- 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 |
|---|---|
| EP1192212B1 (de) | 2006-01-04 |
| NO333555B1 (no) | 2013-07-08 |
| DK1192212T3 (da) | 2006-03-27 |
| PL200275B1 (pl) | 2008-12-31 |
| ATE315060T1 (de) | 2006-02-15 |
| MY151162A (en) | 2014-04-30 |
| BR0011716A (pt) | 2002-03-05 |
| CA2376742A1 (en) | 2000-12-28 |
| AU5974600A (en) | 2001-01-09 |
| PT1192212E (pt) | 2006-05-31 |
| PL352273A1 (en) | 2003-08-11 |
| EP1192212A1 (de) | 2002-04-03 |
| DE19927977A1 (de) | 2000-12-21 |
| NO20016148D0 (no) | 2001-12-17 |
| TWI266784B (en) | 2006-11-21 |
| WO2000078853A1 (de) | 2000-12-28 |
| CN1357024A (zh) | 2002-07-03 |
| MXPA01012835A (es) | 2002-07-30 |
| DE50012023D1 (de) | 2006-03-30 |
| ES2254196T3 (es) | 2006-06-16 |
| JP2003503526A (ja) | 2003-01-28 |
| KR20020019095A (ko) | 2002-03-09 |
| CN1221601C (zh) | 2005-10-05 |
| KR100670079B1 (ko) | 2007-01-17 |
| NO20016148L (no) | 2002-01-16 |
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