NO333555B1 - Anvendelse av cykloheksanpolykarboksylsyrer eller derivater derav som plastifiseringsmidler for fremstilling av toksikologisk fordelaktig plast - Google Patents
Anvendelse av cykloheksanpolykarboksylsyrer eller derivater derav som plastifiseringsmidler for fremstilling av toksikologisk fordelaktig plast Download PDFInfo
- Publication number
- NO333555B1 NO333555B1 NO20016148A NO20016148A NO333555B1 NO 333555 B1 NO333555 B1 NO 333555B1 NO 20016148 A NO20016148 A NO 20016148A NO 20016148 A NO20016148 A NO 20016148A NO 333555 B1 NO333555 B1 NO 333555B1
- Authority
- NO
- Norway
- Prior art keywords
- ester
- phthalate
- hydrogenation
- cas
- obtainable
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 24
- 239000004014 plasticizer Substances 0.000 title claims abstract description 15
- 229920003023 plastic Polymers 0.000 title claims abstract description 12
- 239000004033 plastic Substances 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 150000007513 acids Chemical class 0.000 title abstract description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title abstract description 12
- 230000009286 beneficial effect Effects 0.000 title description 2
- 210000004185 liver Anatomy 0.000 claims abstract description 20
- 241001465754 Metazoa Species 0.000 claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 12
- 102100026798 Peroxisomal acyl-coenzyme A oxidase 1 Human genes 0.000 claims abstract description 11
- 108010008746 palmitoyl CoA oxidase Proteins 0.000 claims abstract description 11
- 230000037396 body weight Effects 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 241000283984 Rodentia Species 0.000 claims abstract description 5
- 238000011282 treatment Methods 0.000 claims abstract description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 37
- 150000002148 esters Chemical class 0.000 claims description 24
- 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 20
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 16
- 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 11
- 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 10
- 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 7
- 210000002784 stomach Anatomy 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 6
- 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 5
- 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 4
- -1 phthalate ester Chemical class 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
- ILVKYQKHSCWQAW-UHFFFAOYSA-N 1-o-heptyl 2-o-undecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC ILVKYQKHSCWQAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 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 3
- 230000002349 favourable effect Effects 0.000 abstract 1
- 125000005498 phthalate group Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-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
- SPCMZKLWAQDUQI-UHFFFAOYSA-N 2-cyclohexyloxycarbonylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)OC1CCCCC1 SPCMZKLWAQDUQI-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
- 102000023984 PPAR alpha Human genes 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
- 125000000217 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
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 2
- 231100000723 toxicological property Toxicity 0.000 description 2
- 231100000027 toxicology Toxicity 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
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- BOVPVRGRPPYECC-UHFFFAOYSA-N 2-methoxycarbonylcyclohexane-1-carboxylic acid Chemical compound COC(=O)C1CCCCC1C(O)=O BOVPVRGRPPYECC-UHFFFAOYSA-N 0.000 description 1
- 102100035474 DNA polymerase kappa Human genes 0.000 description 1
- 101710108091 DNA polymerase kappa Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 229920001944 Plastisol Polymers 0.000 description 1
- KRADHMIOFJQKEZ-UHFFFAOYSA-N Tri-2-ethylhexyl trimellitate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)=C1 KRADHMIOFJQKEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- ILYWGWPJRBBODC-UHFFFAOYSA-N bis(10-methylundecyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCCC(C)C ILYWGWPJRBBODC-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
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- DIMOQAGSNHTROK-UHFFFAOYSA-N bis(2-ethylhexyl) cyclohexane-1,2-dicarboxylate Chemical compound CCCCC(CC)COC(=O)C1CCCCC1C(=O)OCC(CC)CCCC DIMOQAGSNHTROK-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
- QUKHPBOCBWDYMW-UHFFFAOYSA-N bis(2-methylpropyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)COC(=O)C1CCCCC1C(=O)OCC(C)C QUKHPBOCBWDYMW-UHFFFAOYSA-N 0.000 description 1
- OIDQOTHCTOVWOF-UHFFFAOYSA-N bis(6-methylheptyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCOC(=O)C1CCCCC1C(=O)OCCCCCC(C)C OIDQOTHCTOVWOF-UHFFFAOYSA-N 0.000 description 1
- TUOSWEIWIXJUAU-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,1-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1(C(=O)OCCCCCCC(C)C)CCCCC1 TUOSWEIWIXJUAU-UHFFFAOYSA-N 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- ANSWCYTXKAIJOK-UHFFFAOYSA-N dibutyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCOC(=O)C1CCCCC1C(=O)OCCCC ANSWCYTXKAIJOK-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- VKPGBQAXQBOSCY-UHFFFAOYSA-N dicyclohexyl cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OC2CCCCC2)C1C(=O)OC1CCCCC1 VKPGBQAXQBOSCY-UHFFFAOYSA-N 0.000 description 1
- ITKVMAXLADRPIZ-UHFFFAOYSA-N didecyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCCC ITKVMAXLADRPIZ-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
- 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
- GGLHXZYMYYBBHT-UHFFFAOYSA-N dinonyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCC GGLHXZYMYYBBHT-UHFFFAOYSA-N 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
- FUXJJBJXVZIIMV-UHFFFAOYSA-N dioctyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCC FUXJJBJXVZIIMV-UHFFFAOYSA-N 0.000 description 1
- AGEFUZCBLJQXIA-UHFFFAOYSA-N dipropyl cyclohexane-1,2-dicarboxylate Chemical compound CCCOC(=O)C1CCCCC1C(=O)OCCC AGEFUZCBLJQXIA-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
- OACQFHLGZUHNQE-UHFFFAOYSA-N diundecyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCCCC OACQFHLGZUHNQE-UHFFFAOYSA-N 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 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
- 230000008569 process Effects 0.000 description 1
- 230000001850 reproductive effect Effects 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
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)
- Fodder In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials For Medical Uses (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (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 (3)
| Publication Number | Publication Date |
|---|---|
| NO20016148D0 NO20016148D0 (no) | 2001-12-17 |
| NO20016148L NO20016148L (no) | 2002-01-16 |
| NO333555B1 true NO333555B1 (no) | 2013-07-08 |
Family
ID=7911754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20016148A NO333555B1 (no) | 1999-06-18 | 2001-12-17 | Anvendelse av cykloheksanpolykarboksylsyrer eller derivater derav som plastifiseringsmidler for fremstilling av toksikologisk fordelaktig plast |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1192212B1 (https=) |
| JP (1) | JP2003503526A (https=) |
| KR (1) | KR100670079B1 (https=) |
| CN (1) | CN1221601C (https=) |
| AT (1) | ATE315060T1 (https=) |
| AU (1) | AU5974600A (https=) |
| BR (1) | BR0011716A (https=) |
| CA (1) | CA2376742A1 (https=) |
| DE (2) | DE19927977A1 (https=) |
| DK (1) | DK1192212T3 (https=) |
| ES (1) | ES2254196T3 (https=) |
| MX (1) | MXPA01012835A (https=) |
| MY (1) | MY151162A (https=) |
| NO (1) | NO333555B1 (https=) |
| PL (1) | PL200275B1 (https=) |
| PT (1) | PT1192212E (https=) |
| TW (1) | TWI266784B (https=) |
| WO (1) | WO2000078853A1 (https=) |
| ZA (1) | ZA200110300B (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002066412A1 (de) * | 2001-02-16 | 2002-08-29 | Basf Aktiengesellschaft | Verfahren zur herstellung von cyclohexandicarbonsäuren und deren derivaten |
| 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 |
| PT1603982T (pt) | 2003-03-14 | 2017-05-03 | Basf Se | Tintas de impressão compreendendo derivados de ácido ciclohexano policarboxílico |
| 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 |
| US20120220678A1 (en) | 2009-11-03 | 2012-08-30 | Christof Mehler | Thermoplastic compositions having improved flowability |
| 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 |
| 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 |
| 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 |
| 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 |
| EP3147317B1 (de) * | 2015-09-28 | 2017-08-23 | Evonik Degussa GmbH | Tripentylester der trimellitsäure |
| KR102120091B1 (ko) | 2016-03-18 | 2020-06-09 | 누리온 케미칼즈 인터내셔널 비.브이. | 저장 안정한 수성 유기 퍼옥사이드 에멀젼 |
| KR102260895B1 (ko) | 2018-06-12 | 2021-06-07 | 주식회사 엘지화학 | 가소제 조성물 및 이를 포함하는 수지 조성물 |
| WO2020091361A1 (ko) * | 2018-10-29 | 2020-05-07 | 주식회사 엘지화학 | 사이클로헥산 트리에스터계 가소제 조성물 및 이를 포함하는 수지 조성물 |
| 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 |
| AU759882B2 (en) * | 1997-12-19 | 2003-05-01 | Basf Aktiengesellschaft | Method for hydrogenating benzene polycarboxylic acids or derivatives thereof by using a catalyst containing macropores |
| 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 ES ES00945771T patent/ES2254196T3/es not_active Expired - Lifetime
- 2000-06-16 JP JP2001505607A patent/JP2003503526A/ja active Pending
- 2000-06-16 AT AT00945771T patent/ATE315060T1/de active
- 2000-06-16 MX MXPA01012835A patent/MXPA01012835A/es active IP Right Grant
- 2000-06-16 AU AU59746/00A patent/AU5974600A/en not_active Abandoned
- 2000-06-16 CA CA002376742A patent/CA2376742A1/en not_active Abandoned
- 2000-06-16 MY MYPI20002722 patent/MY151162A/en unknown
- 2000-06-16 KR KR1020017016243A patent/KR100670079B1/ko not_active Expired - Fee Related
- 2000-06-16 EP EP00945771A patent/EP1192212B1/de not_active Revoked
- 2000-06-16 DK DK00945771T patent/DK1192212T3/da active
- 2000-06-16 DE DE50012023T patent/DE50012023D1/de not_active Expired - Lifetime
- 2000-06-16 WO PCT/EP2000/005609 patent/WO2000078853A1/de not_active Ceased
- 2000-06-16 PT PT00945771T patent/PT1192212E/pt unknown
- 2000-06-16 BR BR0011716-1A patent/BR0011716A/pt not_active Application Discontinuation
- 2000-06-16 PL PL352273A patent/PL200275B1/pl unknown
- 2000-06-16 CN CNB008091536A patent/CN1221601C/zh not_active Expired - Fee Related
- 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 |
|---|---|
| WO2000078853A1 (de) | 2000-12-28 |
| CA2376742A1 (en) | 2000-12-28 |
| NO20016148L (no) | 2002-01-16 |
| KR20020019095A (ko) | 2002-03-09 |
| PL200275B1 (pl) | 2008-12-31 |
| KR100670079B1 (ko) | 2007-01-17 |
| NO20016148D0 (no) | 2001-12-17 |
| ATE315060T1 (de) | 2006-02-15 |
| CN1357024A (zh) | 2002-07-03 |
| EP1192212A1 (de) | 2002-04-03 |
| MY151162A (en) | 2014-04-30 |
| BR0011716A (pt) | 2002-03-05 |
| DE19927977A1 (de) | 2000-12-21 |
| ZA200110300B (en) | 2003-02-26 |
| TWI266784B (en) | 2006-11-21 |
| PT1192212E (pt) | 2006-05-31 |
| AU5974600A (en) | 2001-01-09 |
| PL352273A1 (en) | 2003-08-11 |
| ES2254196T3 (es) | 2006-06-16 |
| EP1192212B1 (de) | 2006-01-04 |
| MXPA01012835A (es) | 2002-07-30 |
| DE50012023D1 (de) | 2006-03-30 |
| DK1192212T3 (da) | 2006-03-27 |
| CN1221601C (zh) | 2005-10-05 |
| JP2003503526A (ja) | 2003-01-28 |
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