CA2376742A1 - 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
- CA2376742A1 CA2376742A1 CA002376742A CA2376742A CA2376742A1 CA 2376742 A1 CA2376742 A1 CA 2376742A1 CA 002376742 A CA002376742 A CA 002376742A CA 2376742 A CA2376742 A CA 2376742A CA 2376742 A1 CA2376742 A1 CA 2376742A1
- Authority
- CA
- Canada
- Prior art keywords
- ester
- cyclohexane
- acid
- hydrogenating
- obtainable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002253 acid Substances 0.000 title claims abstract description 28
- 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 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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 12
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 230000037396 body weight Effects 0.000 claims abstract description 10
- 108010008746 palmitoyl CoA oxidase Proteins 0.000 claims abstract description 9
- 102100026798 Peroxisomal acyl-coenzyme A oxidase 1 Human genes 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 32
- -1 isodecyl Chemical group 0.000 claims description 22
- 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 7
- 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
- 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
- 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 1
- 238000012360 testing method Methods 0.000 description 11
- 239000004808 2-ethylhexylester Substances 0.000 description 9
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 8
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 8
- 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 5
- 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 5
- 238000000034 method Methods 0.000 description 5
- 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 4
- 108090000854 Oxidoreductases Proteins 0.000 description 3
- 102000004316 Oxidoreductases Human genes 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
- 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
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- GREBHBHIDSJJIV-UHFFFAOYSA-N 2,4,5-tris(10-methylundecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCC(C)C)C(C(=O)OCCCCCCCCCC(C)C)CC1C(O)=O GREBHBHIDSJJIV-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 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
- 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
- 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
- ZTAJBWITWSOBFQ-UHFFFAOYSA-N tris(10-methylundecyl) cyclohexane-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCCCOC(=O)C1CCC(C(=O)OCCCCCCCCCC(C)C)C(C(=O)OCCCCCCCCCC(C)C)C1 ZTAJBWITWSOBFQ-UHFFFAOYSA-N 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
- UWFZTJQXORNGCA-UHFFFAOYSA-N 2,3-bis(cyclohexyloxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCC(C(=O)OC2CCCCC2)C1C(=O)OC1CCCCC1 UWFZTJQXORNGCA-UHFFFAOYSA-N 0.000 description 1
- VGLQDWMSEDWYPK-UHFFFAOYSA-N 2,3-bis(decoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCCCCC VGLQDWMSEDWYPK-UHFFFAOYSA-N 0.000 description 1
- KLCXXAZFEOHBHA-UHFFFAOYSA-N 2,3-bis(ethoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCC KLCXXAZFEOHBHA-UHFFFAOYSA-N 0.000 description 1
- XXPIWCCRSJWWQS-UHFFFAOYSA-N 2,3-bis(icosoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCCCCCCCCCCCCCCC XXPIWCCRSJWWQS-UHFFFAOYSA-N 0.000 description 1
- YOOPRGJTLCUPOX-UHFFFAOYSA-N 2,3-bis(methoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound COC(=O)C1CCCC(C(O)=O)C1C(=O)OC YOOPRGJTLCUPOX-UHFFFAOYSA-N 0.000 description 1
- FQFGDCSGTWMDJZ-UHFFFAOYSA-N 2,3-bis(nonoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCCCC FQFGDCSGTWMDJZ-UHFFFAOYSA-N 0.000 description 1
- XZENZINXJUZBHW-UHFFFAOYSA-N 2,3-bis(octoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCCC XZENZINXJUZBHW-UHFFFAOYSA-N 0.000 description 1
- RHASCXRJYPUOLT-UHFFFAOYSA-N 2,3-bis(propoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCC RHASCXRJYPUOLT-UHFFFAOYSA-N 0.000 description 1
- CNZJCFNRKDTVOE-UHFFFAOYSA-N 2,3-bis(undecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCCCCOC(=O)C1CCCC(C(O)=O)C1C(=O)OCCCCCCCCCCC CNZJCFNRKDTVOE-UHFFFAOYSA-N 0.000 description 1
- JFJQTIQFUNXWAA-UHFFFAOYSA-N 2,3-bis[(2-methylpropan-2-yl)oxycarbonyl]cyclohexane-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)C1CCCC(C(O)=O)C1C(=O)OC(C)(C)C JFJQTIQFUNXWAA-UHFFFAOYSA-N 0.000 description 1
- TZOWFDSOHWUGLQ-UHFFFAOYSA-N 2,4,5-tris(16-methylheptadecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCC(C)C)C(C(=O)OCCCCCCCCCCCCCCCC(C)C)CC1C(O)=O TZOWFDSOHWUGLQ-UHFFFAOYSA-N 0.000 description 1
- GRVTZKLFSZJYOQ-UHFFFAOYSA-N 2,4,5-tris(2-methylpropoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)COC(=O)C1CC(C(=O)OCC(C)C)C(C(=O)OCC(C)C)CC1C(O)=O GRVTZKLFSZJYOQ-UHFFFAOYSA-N 0.000 description 1
- NKCBUDQHAANOOK-UHFFFAOYSA-N 2,4,5-tris(6-methylheptoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCOC(=O)C1CC(C(=O)OCCCCCC(C)C)C(C(=O)OCCCCCC(C)C)CC1C(O)=O NKCBUDQHAANOOK-UHFFFAOYSA-N 0.000 description 1
- OCOTWWJZLXQLOH-UHFFFAOYSA-N 2,4,5-tris(butoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCOC(=O)C1CC(C(=O)OCCCC)C(C(=O)OCCCC)CC1C(O)=O OCOTWWJZLXQLOH-UHFFFAOYSA-N 0.000 description 1
- PESCOZKAVNCALA-UHFFFAOYSA-N 2,4,5-tris(cyclohexyloxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CC(C(=O)OC2CCCCC2)C(C(=O)OC2CCCCC2)CC1C(=O)OC1CCCCC1 PESCOZKAVNCALA-UHFFFAOYSA-N 0.000 description 1
- WPADUAXLNBVMPM-UHFFFAOYSA-N 2,4,5-tris(ethoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCOC(=O)C1CC(C(=O)OCC)C(C(=O)OCC)CC1C(O)=O WPADUAXLNBVMPM-UHFFFAOYSA-N 0.000 description 1
- PXZMDALRLPLTRP-UHFFFAOYSA-N 2,4,5-tris(icosoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCCCCCCCCCCC)CC1C(O)=O PXZMDALRLPLTRP-UHFFFAOYSA-N 0.000 description 1
- ABONQFBBGFQJRT-UHFFFAOYSA-N 2,4,5-tris(methoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound COC(=O)C1CC(C(=O)OC)C(C(=O)OC)CC1C(O)=O ABONQFBBGFQJRT-UHFFFAOYSA-N 0.000 description 1
- PKVYNLFUPLHYSR-UHFFFAOYSA-N 2,4,5-tris(nonoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCC)C(C(=O)OCCCCCCCCC)CC1C(O)=O PKVYNLFUPLHYSR-UHFFFAOYSA-N 0.000 description 1
- TWBHECUGBDIVIP-UHFFFAOYSA-N 2,4,5-tris(octadecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCCCCCCCCC)CC1C(O)=O TWBHECUGBDIVIP-UHFFFAOYSA-N 0.000 description 1
- GDBIKEJLDKWZFG-UHFFFAOYSA-N 2,4,5-tris(octoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)CC1C(O)=O GDBIKEJLDKWZFG-UHFFFAOYSA-N 0.000 description 1
- UVSGBSILANHIRA-UHFFFAOYSA-N 2,4,5-tris(undecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CCCCCCCCCCCOC(=O)C1CC(C(=O)OCCCCCCCCCCC)C(C(=O)OCCCCCCCCCCC)CC1C(O)=O UVSGBSILANHIRA-UHFFFAOYSA-N 0.000 description 1
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- SPCMZKLWAQDUQI-UHFFFAOYSA-N 2-cyclohexyloxycarbonylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)OC1CCCCC1 SPCMZKLWAQDUQI-UHFFFAOYSA-N 0.000 description 1
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- KDZSDQFNNMOHSZ-UHFFFAOYSA-N 3,4-bis(10-methylundecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCCCCCOC(=O)C1CCC(C(O)=O)CC1C(=O)OCCCCCCCCCC(C)C KDZSDQFNNMOHSZ-UHFFFAOYSA-N 0.000 description 1
- NCXOLMDIAWIWQC-UHFFFAOYSA-N 3,4-bis(16-methylheptadecoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1CCC(C(O)=O)CC1C(=O)OCCCCCCCCCCCCCCCC(C)C NCXOLMDIAWIWQC-UHFFFAOYSA-N 0.000 description 1
- CAIPQCSIBWIXLA-UHFFFAOYSA-N 3,4-bis(2-methylpropoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)COC(=O)C1CCC(C(O)=O)CC1C(=O)OCC(C)C CAIPQCSIBWIXLA-UHFFFAOYSA-N 0.000 description 1
- DBWSFYBXCUIEIO-UHFFFAOYSA-N 3,4-bis(6-methylheptoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound CC(C)CCCCCOC(=O)C1CCC(C(O)=O)CC1C(=O)OCCCCCC(C)C DBWSFYBXCUIEIO-UHFFFAOYSA-N 0.000 description 1
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- 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
- UXMBTVGVNXFRPJ-UHFFFAOYSA-N tris(6-methylheptyl) cyclohexane-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCOC(=O)C1CCC(C(=O)OCCCCCC(C)C)C(C(=O)OCCCCCC(C)C)C1 UXMBTVGVNXFRPJ-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)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| 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 |
| DE19927977.2 | 1999-06-18 | ||
| 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 |
|---|---|
| CA2376742A1 true CA2376742A1 (en) | 2000-12-28 |
Family
ID=7911754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002376742A Abandoned CA2376742A1 (en) | 1999-06-18 | 2000-06-16 | 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 (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) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7816553B2 (en) | 2004-06-21 | 2010-10-19 | Basf Se | Cyclohexane polycarboxylic acid derivatives containing adjuvants |
| US10005894B2 (en) | 2012-05-03 | 2018-06-26 | Roquette Freres | Plasticiser compositions comprising gelification accelerators based on ester(s) of 1,4 : 3,6-dianhydrohexitol having low molar weight |
| US11059779B2 (en) | 2016-03-18 | 2021-07-13 | Nouryon Chemicals International B.V. | Storage stable aqueous organic peroxide emulsions |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7816553B2 (en) | 2004-06-21 | 2010-10-19 | Basf Se | Cyclohexane polycarboxylic acid derivatives containing adjuvants |
| US10005894B2 (en) | 2012-05-03 | 2018-06-26 | Roquette Freres | Plasticiser compositions comprising gelification accelerators based on ester(s) of 1,4 : 3,6-dianhydrohexitol having low molar weight |
| US11059779B2 (en) | 2016-03-18 | 2021-07-13 | Nouryon Chemicals International B.V. | Storage stable aqueous organic peroxide emulsions |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20016148L (no) | 2002-01-16 |
| JP2003503526A (ja) | 2003-01-28 |
| ATE315060T1 (de) | 2006-02-15 |
| 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 |
| MXPA01012835A (es) | 2002-07-30 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |