WO2000078853A1 - Verwendung von cyclohexanpolycarbonsäuren als weichmacher zur herstellung toxikologisch günstig zu bewertender kunststoffe - Google Patents

Verwendung von cyclohexanpolycarbonsäuren als weichmacher zur herstellung toxikologisch günstig zu bewertender kunststoffe Download PDF

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Publication number
WO2000078853A1
WO2000078853A1 PCT/EP2000/005609 EP0005609W WO0078853A1 WO 2000078853 A1 WO2000078853 A1 WO 2000078853A1 EP 0005609 W EP0005609 W EP 0005609W WO 0078853 A1 WO0078853 A1 WO 0078853A1
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WO
WIPO (PCT)
Prior art keywords
cyclohexane
ester
acid
obtainable
cas
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PCT/EP2000/005609
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German (de)
English (en)
French (fr)
Inventor
Melanie Brunner
Lucien Thil
Boris Breitscheidel
Rainer Otter
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BASF SE
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BASF SE
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Priority to CA002376742A priority Critical patent/CA2376742A1/en
Priority to BR0011716-1A priority patent/BR0011716A/pt
Priority to EP00945771A priority patent/EP1192212B1/de
Priority to MXPA01012835A priority patent/MXPA01012835A/es
Priority to JP2001505607A priority patent/JP2003503526A/ja
Application filed by BASF SE filed Critical BASF SE
Priority to DE50012023T priority patent/DE50012023D1/de
Priority to AU59746/00A priority patent/AU5974600A/en
Priority to PL352273A priority patent/PL200275B1/pl
Publication of WO2000078853A1 publication Critical patent/WO2000078853A1/de
Priority to NO20016148A priority patent/NO333555B1/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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

Definitions

  • the present invention relates to the use of cyclohexane polycarboxylic acids and derivatives thereof, which are toxicologically favorable, e.g. Esters and / or anhydrides, as plasticizers for the production of toxicologically favorable plastics.
  • toxicologically favorable e.g. Esters and / or anhydrides
  • plasticizers in plastics such as PVC
  • plasticizers in plastics such as PVC
  • phthalic acid esters e.g. Dibutyl, dioctyl or diisononyl esters of phthalic acid used, e.g. emerges from FR-A 23 97 131.
  • phthalic acid esters e.g. Dibutyl, dioctyl or diisononyl esters of phthalic acid used, e.g. emerges from FR-A 23 97 131.
  • phthalates can lead to peroxisome proliferation, which is causally related to the liver tumors that occurred in mouse and rat in long-term studies.
  • PCT / EP 98/08346 discloses that cyclohexane polycarboxylic acids and derivatives thereof can be used as plasticizers.
  • cyclohexane polycarboxylic acids and derivatives thereof in comparison with the phthalates previously mainly used as plasticizers have a lower density and viscosity and, moreover, also lead to an improvement in the low-temperature flexibility of the plastic compared to the use of the corresponding phthalates as plasticizers.
  • the present invention was therefore based on the primary object of providing substances for use as plasticizers in plastics which are not only suitable for use as plasticizers in plastics because of their physical and material properties, but also because of their toxicological properties for such Use are to be classified as suitable.
  • liver tumors in rodents observed in connection with phthalates appears to be mediated via the peroxisome proliferator-activated receptor- ⁇ (PPAR ⁇ ; peroxisome proliferator-activated receptor-a).
  • PPAR ⁇ peroxisome proliferator-activated receptor-a
  • the peroxisome proliferation on which this mechanism is based can be determined using various indicators, including a significant increase in the absolute or relative liver weight and an increase in certain enzyme activities, such as the specific activity of the cyanide-insensitive palmitoyl-CoA oxidase (Pal-CoA oxidase), to prove.
  • the present invention is based on the surprising finding that, in contrast to various conventional plasticizers, in particular phthalates or phthalic acid derivatives, cyclohexane polycarboxylic acids and derivatives thereof, ie nucleus-hydrogenated benzene polycarboxylic acids and derivatives thereof, do not cause biologically significant peroxisome proliferation and therefore not only with regard to Their physical and material properties, but also from a toxicological point of view, can be assessed as favorable in comparison with these conventional plasticizers.
  • a cyclohexane polycarboxylic acid or a derivative thereof or a mixture of two or more thereof is considered to be toxicologically favorable in particular if, in animal experiments with rodents, an oral dose of 1000 mg / kg body weight is administered daily for at least 14 days this cyclohexane polycarboxylic acid or the derivative thereof or the mixture of two or more thereof by gavage, compared to the corresponding untreated control animals, neither a statistically significant increase in the absolute liver weight or the relative liver weight, ie of the liver weight based on the total body weight, a toxicologically relevant increase in the specific enzyme activity of the cyanide-insensitive palmitoyl-CoA oxidase is found.
  • a statistically significant increase in absolute or relative liver weight is e.g. In rats, it usually occurs when an increase in the absolute or relative liver weight of a test animal that has received an oral dose of 1000 mg test substance / kg body weight per gavage over a period of at least 14 days is more than 10% above the increase in the absolute or relative liver weight of a corresponding untreated control animal.
  • a statistically significant increase in the absolute or relative liver weight in the sense of the present invention exists in particular if the statistical increase in the absolute or relative liver weight of the test animal compared to that of the untreated control animal was determined by more than 10% by means of the Dunnett test (Dunnett, CW (1955), A multiple comparison procedure for comparing several treatments with a control, J. Am. Stat. Assoc. 50, 1096-1121; Dunnett, CW (1964), New tables for multiple comparisons with a control, Biometrics, 20 , 482-491).
  • the specific activity [mU / mg protein] of the cyanide-insensitive palmitoyl-CoA oxidase is determined according to Lazarow (1981), Enzymology 72, 315-319, the determination of the amount of protein in the liver homogenate routinely according to protein determination methods well known to the person skilled in the art, such as that Lowry method.
  • the present invention relates to the use of a cyclohexane polycarboxylic acid or a derivative thereof or a mixture of two or more thereof, which (s) in animal experiments with rodents at a daily oral dosage of 1000 mg / kg body weight of the corresponding cyclohexane polycarboxylic acid or the derivative thereof or the mixture of two or more of them by gavage over a period of at least 14 days compared to untreated control animals, neither a significant increase in liver weight after treatment nor a doubling of the liver
  • the specific activity of the cyanide-insensitive palmitoyl-CoA oxidase measured as a homogenate, leads as a plasticizer for the production of toxicologically favorable plastics.
  • cyclohexane polycarboxylic acids and derivatives thereof used according to the invention includes both the respective cyclohexane polycarboxylic acids themselves and derivatives thereof, mono, di or optionally tri or tetra esters and anhydrides of cyclohexane polycarboxylic acids being mentioned in particular.
  • the esters used are alkyl, cycloalkyl and alkoxyalkyl esters, where the alkyl, cycloalkyl and alkoxyalkyl groups generally comprise 1 to 30, preferably 2 to 20 and particularly preferably 3 to 18 carbon atoms and can be branched or linear.
  • Cyclohexane-l, 4-dicarboxylic acid alkyl esters such as, for example, cyclohexane-1,4-dicarboxylic acid monomethyl ester, cyclohexane-1, 4-dicarboxylic acid dimethyl ester, cyclohexane 1, 4-dicarboxylic acid diethyl ester, cyclohexane 1, 4-dicarboxylic acid di-n-hexane propyl ester 1, 4-dicarboxylic acid di-n-butyl ester, cyclohexane 1, 4-dicarboxylic acid di-tert-butyl ester, cyclohexane, 1,4-dicarboxylic acid diisobutyl ester, cyclohexane, 1,4-dicarboxylic acid monoglycol ester, cyclohexane 1, 4-dicarboxylic acid diglycol ester, Cyclohexane 1, 4-dicarboxylic acid di-n-o
  • Cyclohexane-1,3-dicarboxylic acid alkyl esters such as, for example, cyclohexane-1,3-dicarboxylic acid monomethyl ester, cyclohexane-1,3-dicarboxylic acid dimethyl ester, cyclohexane-1,3-dicarboxylic acid diethyl ester, cyclohexane-1,3-dicarboxylic acid di-n-propyl ester, Cyclohexane-1, 3-dicarboxylic acid di-n-butyl ester, cyclohexane 1, 3-dicarboxylic acid di-tert.-butyl ester, cyclohexane 1, 3-dicarboxylic acid diisobutyl ester, cyclohexane 1, 3-dicarboxylic acid monoglycol ester, cyclohexane 1 , 3-dicarboxylic acid diglycol ester, cyclohexane-1,3-
  • Cyclohexane 1,2,4-tricarboxylic acid alkyl esters such as, for example, cyclohexane 1, 2,4-tricarboxylic acid monomethyl ester, cyclohexane 1, 2,4-tricarboxylic acid dimethyl ester, cyclohexane 1, 2,4-tricarboxylic acid diethyl ester, cyclohexane 1, 2, 4-tricarboxylic acid di-n-propyl ester, cyclohexane 1, 2, 4-tricarboxylic acid di-n-butyl ester, cyclohexane 1, 2,4-tricarboxylic acid di-tert-butyl ester, cyclohexane 1,2,4-tricarboxylic acid diisobutyl ester, cyclohexane 1, 2,4-tricarboxylic acid monoglycol ester, cyclohexane 1, 2,4-tricarboxylic acid diglycol ester,
  • Cyclohexane-l, 3,5-tricarboxylic acid alkyl esters such as, for example, cyclohexane-1,3,5-tricarboxylic acid monomethyl ester, cyclohexane-1, 3,5-tricarboxylic acid dimethyl ester, cyclohexane-1,3,5-tricarboxylic acid diethyl ester, cyclohexane 1, 3, 5-tricarboxylic acid di-n-propyl ester, cyclohexane-1, 3,5-tricarboxylic acid di-n-butyl ester, cyclohexane 1,3, 5-tricarboxylic acid di-tert-butyl ester, cyclohexane 1, 3,5-tricarboxylic acid diisobutyl ester, cyclohexane 1, 3.5- tricarboxylic acid monoglycol esters, cyclohexane 1, 3, 5-tricarboxylic acid diglycol esters,
  • Cyclohexane 1,2,3-tricarboxylic acid alkyl esters e.g. Cyclohexane-l, 2,3-tricarboxylic acid monomethyl ester, cyclohexane 1, 2,3-tricarboxylic acid dimethyl ester, cyclohexane 1, 2,3-tricarboxylic acid diethyl ester, cyclohexane 1, 2,3-tricarboxylic acid di-n-propyl ester, cyclohexane 1, 2,3-tricarboxylic acid di-n-butyl ester, cyclohexane 1,2,3-tricarboxylic acid di-tert-butyl ester, cyclohexane 1, 2,3-tricarboxylic acid diisobutyl ester, cyclohexane 1, 2,3-tricarboxylic acid monoglycol ester, cyclohexane 1,2, 3 -tricarboxylic acid diglycol esters,
  • Cyclohexane-l, 2,4,5-tetracarboxylic acid alkyl ester such as, for example, cyclohexane-1, 2,4,5-tetracarboxylic acid monomethyl ester, cyclohexane-l, 2,4,5-tetracarboxylic acid dimethyl ester, cyclohexane-1, 2,4,5- tetracarboxylic acid diethyl ester, cyclohexane 1, 2,4,5-tetracarbonate di-n-propyl ester, cyclohexane 1, 2,4,5-tetracarboxylic acid di-n-butyl ester, cyclohexane 1, 2,4,5-tetracarboxylic acid di-tert.
  • Triethyl cyclohexane-1,2,4,5-tetracarboxylic acid tri-n-propyl cyclohexane-1,2,4,5-tetracarbonate, tri-n-butyl cyclohexane-1, 2,4,5-tetracarboxylate, cyclohexane-1, Tri-tert-butyl 2,4,5-tetracarboxylic acid, cyclohexane 1, triisobutyl 2,4,5-tetracarbonate, triglycol cyclohexane, 1,2,4,5-tetracarboxylic acid, tri- cyclohexane, 2,4,5-tetracarboxylic acid n-octyl ester, cyclohexane 1, 2,4,5-tetracarbonate, triisooctyl ester, cyclohexane 1, 2,4,5-tetracarboxylic acid, tri-2-ethylhexyl ester, cyclohex
  • cyclohexane-1,2-dicarboxylic acid Anhydrides of cyclohexane-1,2-dicarboxylic acid, cyclohexane-1, 2,4-tricarboxylic acid, cyclohexane-l, 2,3-tricarboxylic acid and cyclohexane-1, 2,4,5-tetracarboxylic acid.
  • the cyclohexane-1,2-dicarboxylic acid esters disclosed in PCT / EP 98/08346 and listed again in the following are also to be assessed as toxicologically favorable:
  • Cyclohexane-1, 2-dicarboxylic acid di (isononyl) ester obtainable by hydrogenating a di (isononyl) phthalate with CAS No. 28553-12-0 based on isobutene; a 1,2-di-C ester of cyclohexanedicarboxylic acid, obtainable by hydrogenation of a
  • a 1,2-di-C 9 -n-ester of cyclohexanedicarboxylic acid obtainable by hydrogenating a di-C 9 - ⁇ - phthalate with CAS No. 98515-43-5
  • a 1,2-di (isodecyl) cyclohexanedicarboxylic acid ester obtainable by hydrogenating a di (isodecyl) phthalate consisting mainly of di- (2-propylheptyl) phthalate
  • a 1,2-Di-C. 9- cyclohexanedicarboxylic acid ester obtainable by hydrogenation of the corresponding phthalic acid ester, the branched or linear C 7 .
  • 9 - has alkyl ester groups; Corresponding phthalates that can be used, for example, as starting products have the following CAS no .: Di-C 7; 9- alkyl phthalate with CAS no. 111 381-89-6; Di-C 7 alkyl phthalate with CAS No. 68515-44-6; and Di-C 9 alkyl phthalate with CAS No. 68515-45-7.
  • cyclohexane polycarboxylic acids and derivatives thereof which are toxicologically to be assessed as favorable in the sense of the present invention can be used in all plastics known to the person skilled in the art, in particular in bulk plastics such as PVC, PVB and PVAc.
  • Table 1 Results of the determination of the absolute and relative increase in liver weight and the determination of palmitoyl-CoA oxidase activity in female Wistar rats in (a) the control group (10 untreated animals) and (b) the test group (10 animals which have received an oral dose of 1000 mg / kg body weight of the test substance cyclohexane-1,2-dicarboxylic acid diisononyl ester per gavage for a period of at least 14 days).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (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)
PCT/EP2000/005609 1999-06-18 2000-06-16 Verwendung von cyclohexanpolycarbonsäuren als weichmacher zur herstellung toxikologisch günstig zu bewertender kunststoffe Ceased WO2000078853A1 (de)

Priority Applications (9)

Application Number Priority Date Filing Date Title
PL352273A PL200275B1 (pl) 1999-06-18 2000-06-16 Zastosowanie kwasów cykloheksanopolikarboksylowych albo ich pochodnych albo mieszaniny dwóch lub więcej spośród nich jako zmiękczaczy do wytwarzania tworzyw sztucznych ocenianych jako toksykologicznie korzystne
BR0011716-1A BR0011716A (pt) 1999-06-18 2000-06-16 Uso de um ácido ciclo hexanopolicarboxìlico ou de um derivado do mesmo ou de uma mistura preparada a partir de dois ou mais dos mesmos
EP00945771A EP1192212B1 (de) 1999-06-18 2000-06-16 Verwendung von cyclohexanpolycarbonsäuren als weichmacher zur herstellung toxikologisch günstig zu bewertender kunststoffe
MXPA01012835A MXPA01012835A (es) 1999-06-18 2000-06-16 Uso de los acidos ciclohexanopolicarboxilicos como plastificantes para preparar plasticos clasificados como favorables toxicologicamente.
JP2001505607A JP2003503526A (ja) 1999-06-18 2000-06-16 毒物学的に有利に評価されるべきプラスチックを製造するための可塑剤としてのシクロヘキサンポリカルボン酸の使用
CA002376742A 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
DE50012023T DE50012023D1 (de) 1999-06-18 2000-06-16 Verwendung von cyclohexanpolycarbonsäuren als weichmacher zur herstellung toxikologisch günstig zu bewertender kunststoffe
AU59746/00A AU5974600A (en) 1999-06-18 2000-06-16 Use of cyclohexane polycarboxylic acids as plasticizers in the production of plastics which are rated toxicologically favourable
NO20016148A NO333555B1 (no) 1999-06-18 2001-12-17 Anvendelse av cykloheksanpolykarboksylsyrer eller derivater derav som plastifiseringsmidler for fremstilling av toksikologisk fordelaktig plast

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19927977.2 1999-06-18
DE19927977A DE19927977A1 (de) 1999-06-18 1999-06-18 Verwendung von Cyclohexanpolycarbonsäuren als Weichmacher zur Herstellung toxikologisch günstig zu bewertender Kunststoffe

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WO2000078853A1 true WO2000078853A1 (de) 2000-12-28

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PCT/EP2000/005609 Ceased WO2000078853A1 (de) 1999-06-18 2000-06-16 Verwendung von cyclohexanpolycarbonsäuren als weichmacher zur herstellung toxikologisch günstig zu bewertender kunststoffe

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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=)

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US7297738B2 (en) 2001-09-25 2007-11-20 Exxonmobil Chemical Patents Inc. Plasticized polyvinyl chloride
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WO2011054781A1 (de) 2009-11-03 2011-05-12 Basf Se THERMOPLASTISCHE ZUSAMMENSETZUNGEN MIT VERBESSERTER FLIEßFÄHIGKEIT
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
EP2623087A2 (de) 2012-02-02 2013-08-07 VOCO GmbH Dentale Kompositmaterialien enthaltend tricyclische Weichmacher
EP2623086A2 (de) 2012-02-02 2013-08-07 VOCO GmbH Härtbares Gemisch umfassend Weichmacher mit einem polyalicyclischen Strukturelement zur Anwendung bei der Herstellung dentaler Werkstoffe.
WO2013164545A2 (fr) 2012-05-03 2013-11-07 Roquette Freres Compositions plastifiantes comprenant des accelerateurs de gelification a base d'ester de 1,4 : 3,6-dianhydrohexitol de faible poids molaire
WO2014080151A1 (fr) 2012-11-26 2014-05-30 Roquette Freres Compositions de diesters mixtes de 1,4 : 3,6-dianhydrohexitol
WO2016020624A1 (fr) 2014-08-07 2016-02-11 Roquette Freres Composition plastifiante liquide
EP1603982B1 (de) 2003-03-14 2017-01-25 Basf Se Druckfarben mit cyclohexanpolycarbonsäure-derivaten
EP2121202B1 (de) 2006-12-19 2017-03-22 Basf Se Verwendung von cyclohexanpolycarbonsäureestern für die herstellung von beschichtungsstoffen für das coil-coating-verfahren und von beschichteten coils
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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
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US7297738B2 (en) 2001-09-25 2007-11-20 Exxonmobil Chemical Patents Inc. Plasticized polyvinyl chloride
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EP1603982B1 (de) 2003-03-14 2017-01-25 Basf Se Druckfarben mit cyclohexanpolycarbonsäure-derivaten
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US7816553B2 (en) 2004-06-21 2010-10-19 Basf Se Cyclohexane polycarboxylic acid derivatives containing adjuvants
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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
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US10640626B2 (en) 2012-11-26 2020-05-05 Roquette Freres Compositions of mixed diesters of 1,4: 3,6-dianhydrohexitol
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DE19927977A1 (de) 2000-12-21
EP1192212A1 (de) 2002-04-03
MXPA01012835A (es) 2002-07-30
KR20020019095A (ko) 2002-03-09
PT1192212E (pt) 2006-05-31
ES2254196T3 (es) 2006-06-16
PL200275B1 (pl) 2008-12-31
CN1221601C (zh) 2005-10-05
CA2376742A1 (en) 2000-12-28
BR0011716A (pt) 2002-03-05
AU5974600A (en) 2001-01-09
TWI266784B (en) 2006-11-21
NO333555B1 (no) 2013-07-08
ATE315060T1 (de) 2006-02-15
ZA200110300B (en) 2003-02-26
JP2003503526A (ja) 2003-01-28
CN1357024A (zh) 2002-07-03
KR100670079B1 (ko) 2007-01-17
DK1192212T3 (da) 2006-03-27
NO20016148D0 (no) 2001-12-17

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