EP1761596A2 - Adjuvants contenant des derives d'acide cyclohexane polycarboxylique - Google Patents

Adjuvants contenant des derives d'acide cyclohexane polycarboxylique

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Publication number
EP1761596A2
EP1761596A2 EP05769030A EP05769030A EP1761596A2 EP 1761596 A2 EP1761596 A2 EP 1761596A2 EP 05769030 A EP05769030 A EP 05769030A EP 05769030 A EP05769030 A EP 05769030A EP 1761596 A2 EP1761596 A2 EP 1761596A2
Authority
EP
European Patent Office
Prior art keywords
acid ester
agents
cyclohexanedicarboxylic acid
weight
acid esters
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.)
Withdrawn
Application number
EP05769030A
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German (de)
English (en)
Inventor
Uwe Storzum
Boris Breitscheidel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP10177776.1A priority Critical patent/EP2377844B1/fr
Publication of EP1761596A2 publication Critical patent/EP1761596A2/fr
Withdrawn legal-status Critical Current

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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
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/75—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a six-membered ring

Definitions

  • the present invention relates to the use of 1, 2-cyclohexanedicarboxylic acid esters as auxiliaries or in auxiliaries selected from the group consisting of surface-active compositions, quenching aids, rheology aids, quenchers for chemical reactions, desensitizing agents, pharmaceutical products, plasticizers in adhesives, impact modifiers and fillers.
  • EP-A 0 541 788 discloses esters of lactic acid and 2-butoxyethanol, esters of phthalic acid and 2- (2-butoxy) ethanol, methylphenylcarbinol, ethylene glycol, diethylene glycol, diacetone alcohol, propylene glycol, mono- and diether of ethylene or propylene glycol or mixtures thereof to be used as flow or film formation aids in coating compositions.
  • These flow or film formation aids improve flow while minimizing foaming.
  • some of these flow aids are toxicologically unsafe, so it is desirable to replace them with toxicologically harmless compounds.
  • coating compositions can additionally contain internal coalescing agents, for example butyl octyl phthalate. It is also desirable to replace phthalates as coalescing agents that are toxicologically unsafe with toxicologically harmless compounds.
  • EP-A 0 523 122 relates to lubricant compositions which contain synthetic esters of aliphatic polyols and monocarboxylic acids as additives or oil phase. It is desirable to expand the range of possible additives so that the properties of lubricant compositions can be optimally adapted to their conditions of use.
  • phthalic acid diesters Defoamers, foam inhibitors and wetting agents often contain phthalic acid diesters. However, these have come into talk for environmental reasons, so that it is desirable to replace the phthalic acid diesters with compounds that are environmentally safe.
  • the object of the present application is therefore to provide toxicologically safe compounds which can be used in a variety of ways as auxiliaries or in auxiliaries and are suitable for replacing additives which are potentially toxicologically questionable, without negatively affecting the properties of the products in which the auxiliaries are used influence.
  • the object is achieved by using 1, 2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1, 2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1, 2-diisononylcyclohexanedicarboxylic acid ester in auxiliaries or as aids selected from the group consisting of the following aids: surface-active compositions selected from flow aids or film-forming aids, defoamers, foam inhibitors, wetting agents, coalescing agents and emulsifiers; Lubricants selected from the group consisting of; Kalandrierosmitteln; rheological; Quenchers for chemical reactions; desensitizing agents; pharmaceutical products; Plasticizers in adhesives; Impact modifiers and adjusting agents.
  • 1, 2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1,
  • 1,2-cyclohexanedicarboxylic acid esters have essentially been used as plasticizers for plastics, in particular PVC (e.g. WO 00/78853), whereas their use in other technical fields has hitherto been virtually unknown. Further uses of 1,2-cyclohexanedicarboxylic acid esters in general form are mentioned in the following documents:
  • DE-A 102 32 868 and DE-A 102 25 656 relate to the hydrogenation of aromatic compounds, in particular the production of alicyclic carboxylic acids or their esters by core hydrogenation of the corresponding aromatic polycarboxylic acids or their esters as well as suitable catalysts for the hydrogenation.
  • the polycarboxylic acid esters produced by means of the hydrogenation processes disclosed in DE-A 102 32 868 and DE-A 102 25 656 can be used in addition to being used as a plasticizer as a lubricating oil component, as a constituent of cooling liquids and metal working liquids. They can also be used as components in paints, varnishes, inks and adhesives.
  • WO 03/029168 discloses mixtures of alicyclic polycarboxylic esters with a high cis content, which are prepared by core hydrogenation of the corresponding aromatic polycarboxylic esters. In addition to its use as a plasticizer, WO 03/029168 discloses in general terms the use of the alicyclic polycarboxylic acid esters as a lubricating oil component, as a constituent of cooling liquids and metalworking liquids.
  • WO 03/029181 discloses mixtures of alicyclic polycarboxylic acid esters with a trans-isomer content of over 10 mol%, which are prepared by core hydrogenation of the corresponding aromatic polycarboxylic acid esters.
  • WO 03/029181 discloses in general terms the use of the alicyclic polycarboxylic acid esters as a lubricating oil component, as a component of cooling liquids and metalworking liquids.
  • JP-A 09 249 890 relates to special aliphatic cyclic carboxylic acid esters as lubricants in metalworking.
  • the aliphatic cyclic carboxylic acid esters can be cyclohexane or cyclohexenedicarboxylic acid esters.
  • 1,2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester, preferably 1 , 2-diisononylcyclohexanedicarboxylic acid esters, as or in auxiliaries, are suitable for various other applications which have not yet been mentioned in the prior art.
  • cyclohexane-1,2-dicarboxylic acid esters disclosed in WO 99/32427 and listed again below:
  • CycIohexan-1, 2-dicarboxylic acid di (isononyl) ester obtainable by hydrogenation of a di (isononyl) phthalate with the CAS No. 68515-48-0;
  • CycIohexan-1,2-dicarboxylic acid di (isononyl) ester obtainable by hydrogenation of a di (isononyl) phthalate with CAS No. 28553-12-0, based on n-butene; 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-C9 ester of cyclohexanedicarboxylic acid, obtainable by hydrogenating a di (nonyl) phthalate with CAS No. 68515-46-8.
  • 1,2-cyclohexanedicarboxylic acid esters are selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2- ethylhexyl) cyclohexanedicarboxylic acid esters and 1,2-diisononylcyclohexanedicarboxylic acid esters, the 1,2-cyclohexanedicarboxylic acid esters preferably having diisobutyl radicals.
  • 1,2-cyclohexanedicarboxylic acid esters are selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2- Di- (2-ethylhexyl) cyclohexanedicarboxylic acid esters and 1,2-diisononylcyclohexanedicarboxylic acid esters are used, the 1,2-cyclohexanedicarboxylic acid esters preferably having 2-ethylhexyl or isononyl radicals.
  • 1,2-cyclohexanedicarboxylic acid esters are selected from the group consisting of 1, 2-diisobutylcyclohexanedicarboxylic acid ester, 1, 2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononyl-cyclo-hexo-ester , used, the 1,2-cyclohexanedicarboxylic acid esters preferably having 2-ethylhexyl or isononyl radicals.
  • calendering aids and rheology aids or as calendering aids or rheology aids in quenchers or as quenchers, in pharmaceutical compositions, in time-release compositions 1, 2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid esters, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid esters, the 1,2-cyclohexanedicarboxylic acid esters preferably having isobutyl residues.
  • the 1,2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester are preferably prepared in accordance with the process disclosed in WO 99/32427 , This process comprises hydrogenating a benzene polycarboxylic acid or a derivative thereof or a mixture of two or more thereof by contacting the benzene polycarboxylic acid or the derivative thereof or the mixture of two or more thereof with a hydrogen-containing gas in the presence of a catalyst which is at least active metal a metal of subgroup VIII of the periodic table, alone or together with at least one metal of subgroup I or VII of the periodic table, applied to a carrier, the carrier having macropores.
  • the carrier has an average
  • a catalyst in which the amount of active metal is 0.01 to 30% by weight, based on the total weight of the catalyst, and 10 to 50% of the pore volume of the carrier of macropores with a pore diameter in the range from 50 nm to 10,000 nm and 50 to 90% of the pore volume of the support of mesopores with a pore diameter in the range from 2 to 50 nm are formed, the sum of the proportions of the pore volumes adding up to 100%.
  • the catalyst has 0.01 to 30% by weight, based on the total weight of the catalyst, of an active metal, applied to a support, the support having an average pore diameter of at least 0.1 ⁇ m and a BET surface area of at most 15 m 2 / g.
  • all supports which have macropores ie supports which only have macropores, and those which contain mesopores and / or micropores in addition to macropores can be used as supports.
  • all metals of subgroup VIII of the periodic table can be used as active metal.
  • Platinum, rhodium, palladium, cobalt, nickel or ruthenium or a mixture of two or more thereof are preferably used as active metals, ruthenium in particular being used as the active metal.
  • Copper and / or rhenium are preferably used among the metals of the I or VII or the I and VII subgroups of the periodic table which can also be used, and which can likewise all be used in principle.
  • macropores and “mesopores” are used in the context of the present application as used in Pure Appl. Chem., 45 p. 79 (1976), namely as pores whose diameter is above 50 nm (macropores) or whose diameter is between 2 nm and 50 nm (mesopores).
  • the content of the active metal is generally 0.01 to 30% by weight, preferably 0.01 to 5% by weight, particularly preferably 0.1 to 5% by weight, in each case based on the total weight of the catalyst used.
  • benzene polycarboxylic acid or a derivative thereof used in WO 99/32427 includes all benzene polycarboxylic acids per se, for example phthalic acid, I- sophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, hemimellitic acid and pyrromellitic acid and derivatives thereof, in particular mono-, di-, tri- and tetraesters, in particular alkyl esters, and anhydrides.
  • the 1,2-cyclohexanedicarboxylic acid esters preferably used according to the invention are selected from the group consisting of 1,2-diisobutyicyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester are generally reacted with benzene polycarboxylic acids the alcohols corresponding to the alkyl groups of the esters. Suitable reaction conditions for reacting the benzene polycarboxylic acids with the corresponding alcohols are known to the person skilled in the art.
  • Another object of the present application is therefore the use of 1,2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid esters, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester Auxiliaries or in auxiliaries selected from the group consisting of surface-active compositions, calendering aids, rheology aids, quenchers for chemical reactions, desensitizing agents, pharmaceutical products, plasticizers in adhesives, impact modifiers and adjusting agents, the 1,2-cyclohexanedicarboxylic acid esters being preparable by the following process
  • R is isobutyl, 2-ethylhexyl or isononyl
  • step b) A preferred embodiment of the hydrogenation of the phthalic acid ester of the formula III (step b)) has been mentioned above.
  • Phthalic acid is used as the benzene polycarboxylic acid. Phthalic acid is commercially available.
  • Isobutanol, 2-ethylhexanol or isononanol (C9 alcohol) are therefore used.
  • the alcohols used for the esterification with phthalic acid can be the corresponding individual isomers of C9 alcohol or mixtures of different C9 alcohols with isomeric alkyl radicals with the same number of carbon atoms.
  • Isobutanol and 2-ethylhexanol are each individual isomers, i.e. alcohols with an isobutyl or 2-ethylhexyl radical.
  • the alcohols or alcohol mixtures suitable for reaction with phthalic acid can be prepared by all processes known to the person skilled in the art. Suitable processes for the production of alcohols or process steps which are used in the production of alcohols are, for example:
  • carboxylic acids and carboxylic acid esters in particular fatty acids and fatty acid esters, for example as disclosed in US 5,463,143, US 5,475,159, WO 94/10112, CA 2,314,690, WO 94/06738, JP-A 06 065 125 and US 3,361,832.
  • Alcohols used - as mentioned above isobutanol, 2-ethylhexanol and isononanol.
  • 2-ethylhexanol and isononanol are particularly preferably prepared by catalytic hydroformylation (also referred to as oxo reaction) of olefins and subsequent hydrogenation of the aldehydes formed.
  • Suitable hydroformylation processes are known to the person skilled in the art and are disclosed in the documents mentioned above.
  • the alcohols and alcohol mixtures disclosed in the documents mentioned can be reacted with phthalic acid to give the desired 1,2-cyclohexanedicarboxylic acid esters or ester mixtures.
  • Cg alcohols or mixtures containing C 9 alcohols are preferably prepared by dimerization of butenes, hydroformylation of the octenes obtained and subsequent hydrogenation of the C 9 aldehydes obtained.
  • Suitable processes and mixtures containing Gg alcohol are described, for example, in WO 92/13818, DE-A 20 09 505, DE-A 199 24 339, EP-A 1 113 034, WO 2000/63151, WO 99/25668, JP- A 1 160 928, JP-A 03 083 935, JP-A 2000/053803, EP-A 0 278 407 and EP-A 1 178 029.
  • alkyl groups of the cyclohexanediisononyl ester have the same number of carbon atoms but have different branches and thus form isomer mixtures.
  • the proportion of the different isomers of the alkyl groups generally results from the composition of the C9 alcohols which are used for the esterification of phthalic acid and which, after esterification, are hydrogenated to the corresponding cyclohexanedicarboxylic acid esters. Suitable alcohol mix gene have already been mentioned above.
  • branched alkyl radicals having a certain number of carbon atoms are to be understood in addition to the individual isomers, isomer mixtures whose composition - as mentioned above - results from the composition of the alcohols used for the esterification of phthalic acid.
  • the isobutyl radical or the 2-ethylhexyl radical which, according to the present application, is used in the 1,2-diisobutylcyclohexanedicarboxylic acid ester or 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester used according to the invention is, as mentioned above, in each case by defined residues, not - as is possible in the case of the isononyl residue - by isomer mixtures.
  • alkyl radicals R of the 1,2-cyclohexanedicarboxylic acid ester is an isononyl radical
  • C9-alcohol mixtures with an ISO index of 1 to 1.5, in particular nonanol mixtures with an ISO index of 1.25 or 1.6, are very particularly preferably used.
  • the ISO index is a dimensionless quantity that was determined using gas chromatography.
  • Sample preparation 3 drops of the sample are kept in 1 ml MSTFA and at 80 ° C for 60 minutes
  • GC conditions capillary column: Ultra-1 - length: 50 m - inner diameter: 0.25 mm - film thickness: 0.1 micron carrier gas: helium column pre-pressure: 200 psi constant split: 80 ml / min septum rinse: 3 ml / min furnace temperature: 120 ° C, 25 min isothermal Injector temperature: 250 ° C Detector temperature: 250 ° C (FID) Injection volume: 0.5 microliter
  • the iso index is thus calculated from the degree of branching of the components contained in the alcohol mixture and the amount of the corresponding components (determined by means of gas chromatography).
  • the isononanols are prepared according to the above methods. It is particularly preferred to use a nonanol mixture in which 0 to 20% by weight, preferably 0.5 to 18% by weight, particularly preferably 6 to 16% by weight of the nonanol mixture have no branching, 5 to 90 % By weight, preferably 10 to 80% by weight, particularly preferably 45 to 75% by weight, a branch, 5 to 70% by weight, preferably 10 to 60% by weight, particularly preferably 15 to 35% by weight .-% have two branches, 0 to 10% by weight, preferably 0 to 8% by weight, particularly preferably 0 to 4% by weight three branches and 0 to 40% by weight, preferably 0.1 to 30 % By weight, particularly preferably 0.5 to 6.5% by weight. other components. Other components are generally understood to mean nonanols with more than three branches, decan
  • the present application also relates to 1,2-cyclohexanedicarboxylic acid esters which can be prepared by a process comprising the steps
  • R ' isobutyl, 2-ethylhexyl or isononyl
  • alkyl radicals R ' have degrees of branching from 0.1 to 4, preferably 0.5 to 3, particularly preferably 0.8 to 2, very particularly preferably 1 to 1.5 (ISO index),
  • Preferred alcohols R'-OH, in particular nonanol mixtures are the abovementioned alcohols and alcohol mixtures.
  • the 1, 2-cyclohexanedicarboxylic acid esters according to the invention selected from the group consisting of 1, 2-diisobutylcyclohexanedicarboxylic acid ester, 1, 2-di- (2-ethylhexyl) - cyclohexanedicarboxylic acid ester and 1, 2-diisononylcyclohexanedicarboxylic acid ester are particularly suitable as or in auxiliaries according to the present application ,
  • the 1, 2-cyclohexanedicarboxylic acid esters used according to the invention are particularly suitable for use in surface-active compositions selected from the group consisting of flow aids, film-forming aids, defoamers, anti-foaming agents, wetting agents, coalescing agents and emulsifiers.
  • the present application therefore also relates to surface-active compositions selected from the group consisting of flow aids, film-forming aids, defoamers, foam preventatives, wetting agents, coalescing agents and emulsifiers comprising at least one 1,2-cyclohexanedicarboxylic acid ester selected from the group consisting of 1,2- Diisobutylcyclohexanedicarboxylic acid ester, 1, 2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1, 2-diisononylcyclohexanedicarboxylic acid ester.
  • 1,2-cyclohexanedicarboxylic acid ester selected from the group consisting of 1,2- Diisobutylcyclohexanedicarboxylic acid ester, 1, 2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1, 2-diisononylcyclo
  • compositions of the surface-active compositions and preferred amounts of the individual components of the compositions are known to the person skilled in the art.
  • the 1, 2-cyclohexanedicarboxylic acid esters used according to the invention can also form the surface-active compositions on their own, without further additional compounds.
  • Flow or film-forming aids are suitable for improving the flow and minimizing foaming. They are preferably used in coating compositions in amounts customary for customary flow and film-forming aids. Suitable compositions and suitable amounts of flow and film-forming aids of coating compositions used therein are known to the person skilled in the art.
  • 1,2-Diisobutylcyclohexanedicarboxylic acid ester is preferably used in the flow and film-forming aids or as flow and film-forming aids.
  • 1, 2-cyclohexanedicarboxylic acid esters used according to the invention are selected from the group consisting of 1, 2-diisobutylcyclohexanedicarboxylic acid ester, 1, 2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1, 2-diisononylcyclohexanedicarboxylic acid ester as internal coalescing agents which can also be used in coating compositions and suitable amounts of flow and film-forming aids used therein.
  • the 1, 2- Cyclohexanedicarboxylic acid esters are used in the amounts customary for customary coalescing agents, which are known to the person skilled in the art, in the coating composition.
  • 1,2-Di- (2-ethylhexyl) -cyclohexanedicarboxylic acid esters and 1,2-diisononylcyclohexanedicarboxylic acid esters are preferably used in the coalescing agents or as coalescing agents.
  • 1, 2-cyclohexanedicarboxylic acid esters used according to the invention can be selected from the group consisting of 1, 2-diisobutylcyclohexanedicarboxylic acid ester, 1, 2-di ⁇ (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1, 2-diisononylcyclohexanedicarboxylic acid ester as defoamer or antifoam be used.
  • defoamers or antifoams are also used, for example, in coating compositions.
  • the defoamers and antifoam agents can be used as additives in detergent and cleaning agent compositions and other defoaming liquid media.
  • the 1,2-cyclohexanedicarboxylic acid esters are used in amounts customary for conventional defoamers or antifoams. Suitable amounts of defoamers or antifoams are dependent on the intended use and are easy to determine for the person skilled in the art. Further information regarding defoamers is e.g. in Ulimann (4.) 20, 411 to 414, and information regarding anti-foaming agents is e.g. in Adhesion 29, 21 (1985).
  • 1,2-Di- (2-ethylhexyl) -cyclohexanedicarboxylic acid esters and 1,2-diisononylcyclohexanedicarboxylic acid esters are preferably used in the defoamers or antifoams or as defoamers or antifoams.
  • 1,2-cyclohexanedicarboxylic acid esters used in accordance with the invention can be selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester in or as a wetting agent (s) are used.
  • wetting agents serve in particular as auxiliaries (additives) in the textile industry.
  • Suitable amounts of 1,2-cyclohexanedicarboxylic acid ester when used in or as wetting agent (s) correspond to the amounts customary for customary wetting agents and are known to the person skilled in the art.
  • 1,2-Di- (2-ethylhexyl) -cyclohexanedicarboxylic acid esters and 1,2-diisononylcyclohexanedicarboxylic acid esters are preferably used in the wetting agents or as wetting agents.
  • 1,2-cyclohexanedicarboxylic acid esters used according to the invention is selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester as emulsifiers of the present application.
  • the 1,2-cyclohexanedicarboxylic acid esters can be used to form emulsions for any purpose. Suitable amounts of cyclohexane polycarboxylic acid derivatives when used as an emulsifier correspond to the amounts customary for conventional emulsifiers. These are dependent on the intended use and are known to the person skilled in the art.
  • 1,2-Di- (2-ethylhexyl) cyclohexanedicarboxylic acid esters and 1,2-diisononylcyclohexanedicarboxylic acid esters are preferably used in the emulsifiers or as emulsifiers.
  • the 1,2-cyclohexanedicarboxylic acid esters when used in or as surface-active compositions, are used in an amount of up to 50% by weight, based on the particular composition in which the cyclohexane polycarboxylic acid derivatives are used in or as surface-active compositions ,
  • the proportion of the at least one cyclohexane polycarboxylic acid derivative is preferably 0.01 to 10% by weight, particularly preferably 0.1 to 5% by weight.
  • 1,2-cyclohexanedicarboxylic acid esters can be selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1, 2-diisononylcyclohexanedicarboxylic acid ester according to the present application as a calendering aid or rheology aid be used.
  • calendering aids these can improve the sliding and adhesive properties of the plastic to be processed during processing.
  • 1,2-cyclohexanedicarboxylic acid esters are used as calendering aids or rheology aids correspond to the customarily used amounts of conventional calendering or rheology aids and are known to the person skilled in the art.
  • 1,2-Diisobutylcyclohexanedicarboxylic acid ester is preferably used in the calendering aids or rheology aids or as a calendering aid or rheology aid.
  • Another object of the present application relates to the use of 1,2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester according to the present application as a quencher for chemical reactions or desensitizing agents.
  • 1,2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester according to the present application as a quencher for chemical reactions
  • the present application therefore further relates to quenchers for chemical reactions or desensitizing agents containing at least one cyclohexane1,2-cyclohexanedicarboxylic acid ester, preferably at least one 1,2-cyclohexanedicarboxylic acid ester, as disclosed in accordance with the present application.
  • the quencher or the desensitizing agent can contain the at least one 1,2-cyclohexanedicarboxylic acid ester as a single component or one of several components.
  • 1,2-cyclohexanedicarboxylic acid ester is used as a quencher for chemical reactions, preferred chemical reactions are the synthesis of acrylic acid or maleic anhydride.
  • preferred chemical reactions are the synthesis of acrylic acid or maleic anhydride.
  • reactive intermediates or products from the gas phase can be trapped.
  • the 1,2-cyclohexanedicarboxylic acid esters used according to the invention can advantageously be used for reactive intermediates or for the products because of their outstanding dissolving power.
  • the amount of 1,2-cyclohexanedicarboxylic acid esters corresponds to the amount of customary quenchers usually used and is known to the person skilled in the art.
  • 1,2-Diisobutylcyclohexanedicarboxylic acid ester is preferably used in the quenchers or as quencher.
  • the present application comprises the use of the 1,2-cyclohexanedicarboxylic acid esters disclosed above selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyciohexanedicarboxylic acid ester desensitizing agent.
  • the 1,2-cyclohexanedicarboxylic acid esters are particularly preferably used as desensitizing agents for organic peroxides or nitrocellulose. You can stabilize reactive / explosive products to ensure safe transportation and use of the products.
  • 1,2-cyclohexanedicarboxylic acid esters Due to their chemical affinity for reactive / explosive products, the 1,2-cyclohexanedicarboxylic acid esters are outstandingly suitable as desensitizing agents.
  • the 1,2-cyclohexanedicarboxylic acid esters are used in amounts customary for conventional desensitizing agents which are known to the person skilled in the art.
  • 1,2-Diisobutylcyclohexanedicarboxylic acid ester is preferably used in the desensitizing agents or as desensitizing agent.
  • compositions in which the 1,2-cyclohexanedicarboxylic acid esters disclosed above can be used as desensitizing agents are disclosed, for example, in EP-A 0772 609. Furthermore, the disclosed 1,2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester are suitable for use in pharmaceutical products.
  • Another object of the present application therefore relates to pharmaceutical products containing at least one 1,2-cyclohexanedicarboxylic acid ester selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) -cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarbonate klareester.
  • 1,2-cyclohexanedicarboxylic acid ester selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) -cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarbonate klareester.
  • the 1, 2-cyclohexanedicarboxylic acid esters used according to the invention can be used in the pharmaceutical compositions, for example because of their toxicological harmlessness, as plasticizers in plastics which are present in the pharmaceutical compositions.
  • plasticizers in plastics which are present in the pharmaceutical compositions.
  • suitable plastics and suitable amounts of the at least one 1,2-cyclohexanedicarboxylic acid ester used as plasticizer are known to the person skilled in the art.
  • 1,2-Diisobutylcyclohexanedicarboxylic acid ester is preferably used in the pharmaceutical compositions
  • 1,2-cyclohexanedicarboxylic acid esters used according to the invention can be selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester in what is known as time -release compositions are used, that is compositions with prolonged release of medicinal and / or nutritional active ingredients, for example for oral administration. Suitable compositions are disclosed, for example, in EP-A 0 709 087.
  • 1,2-Diisobutylcyclohexanedicarboxylic acid esters are preferably used in the time-release compositions
  • 1, 2-cyclohexanedicarboxylic acid esters selected from the group consisting of 1, 2-diisobutylcyclohexanedicarboxylic acid esters, 1, 2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid esters and 1, 2-diisononylcyclohexanedicarboxylic acid esters according to the present application can be used as plasticizers in adhesives.
  • Another object of the present application is therefore an adhesive containing at least one 1,2-cyclohexanedicarboxylic acid ester selected from the group consisting of 1, 2-diisobutylcyclohexanedicarboxylic acid ester, 1, 2-di- (2-ethylhexyl) - cyclohexanedicarboxylic acid ester and 1, 2-diisononylcyclohexanedicarboxylic acid ester.
  • the adhesives containing the disclosed 1,2-cyclohexanedicarboxylic acid esters can e.g. in the areas of paper and packaging, wood, construction, household, hobby and office, in the automotive industry, in medicine, in electronics, in shoe production, as well as in adhesive tapes in the application areas mentioned.
  • the adhesives containing 1,2-cyclohexanedicarboxylic acid esters are used in medicine. This is advantageous since the 1,2-cyclohexanedicarboxylic acid esters used according to the invention do not have an allergy-causing effect.
  • the 1,2-cyclohexanedicarboxylic acid esters according to the invention can be used in various types of adhesive for various applications.
  • the areas mentioned and the suitable adhesives are explained in more detail below:
  • the adhesives containing the 1, 2-cyciohexanedicarboxylic acid esters used according to the invention are used for the production of impermeable packaging materials such as composite films or for the hermetic sealing of packaging (e.g. coffee packaging) for the modern form of distribution, self-service, ready meals and frozen foods.
  • Low and high temperature resistant adhesives enable the production of freezer and microwave packaging.
  • the adhesives used to manufacture food packaging must meet the strict regulations of the Food Act.
  • Adhesives which are particularly suitable for use in the wood sector and which contain the 1,2-cyclohexanedicarboxylic acid esters used according to the invention are polycondensation tion, dispersion and hot melt adhesives.
  • the composition of these adhesives is known to the person skilled in the art.
  • the adhesives containing the 1, 2-cyclohexanedicarboxylic acid esters used according to the invention can be found in wallpapers, floor coverings, e.g. made of linoleum, rubber or textile, as well as tiles or parquet, or insulating glass windows.
  • the adhesives containing 1, 2-cyclohexanedicarboxylic acid esters used according to the invention can be used in all-purpose adhesives, glue sticks, paper and craft adhesives, contact adhesives, superglues, and adhesives for plastic and cardboard, cardboard, photos and labels. They are characterized by simple, clean, quick and environmentally friendly gluing, because they do not use solvents. Furthermore, the adhesives can be used as model construction adhesives, assembly adhesives and 2-component adhesives. Water-based or solvent-free adhesive systems are preferred.
  • the adhesives containing the 1,2-cyclohexanedicarboxylic acid esters used according to the invention are suitable for use in the automotive industry. You will e.g. used in adhesives based on polyurethane or in 2-component adhesives. The composition of such adhesives is known to the person skilled in the art.
  • the adhesives containing the 1, 2-cyclohexanedicarboxylic acid esters used according to the invention can be used, for example, in plasters, for gluing joint prostheses, in dentistry for gluing bridges, crowns, veneers and inlays and for the production of all types of hygiene articles such as diapers, pads, surgical drapes and Handkerchiefs are used. They are also used to package medicines in blister packs to protect the tablets from moisture, dirt and bacteria.
  • 1,2-cyclohexanedicarboxylic acid esters used according to the invention are e.g. used in photo-initiated adhesives, sealants and potting compounds for chip potting, in chip-on-board technology, for chip encapsulation and as flip-chip underfillers.
  • Natural or synthetic rubber adhesives dispersion adhesives based on plastic polymers and water-based adhesives made from starch, dextrin and cellulose derivatives are used for gluing in the interior of shoes. All of these adhesives are primarily processed using the wet adhesive process. According to the invention, the adhesives mentioned contain 1,2-cyclohexanedicarboxylic acid esters. Suitable compositions of the adhesives are known to the person skilled in the art.
  • Hot melt adhesives based on ethylene-vinyl acetate copolymers are used for lamination, polyamide adhesives for buggening. According to the invention, these adhesives likewise contain 1,2-cyclohexanedicarboxylic acid esters. Suitable compositions of the adhesives are known to the person skilled in the art.
  • connection between the upper of the shoe and the insole can be carried out using polyamide or polyester hotmelt adhesives, which also contain the 1,2-cyclohexanedicarboxylic acid esters used according to the invention.
  • the outsoles can be glued to the shoe upper with solvent-based or dispersion-based adhesives based on polychloroprene or polyurethane, which also contain the 1,2-cyclohexanedicarboxylic acid esters used according to the invention.
  • the adhesives containing the 1,2-cyclohexanedicarboxylic acid esters used according to the invention can furthermore be used in adhesive tapes.
  • Self-adhesive tapes are produced as problem-solving concepts for industry, for other commercial customers and for private needs.
  • the market has a large number of the latest adhesive technologies and offers individual problem solutions for all important applications with a focus on the packaging, electrical, transportation and paper industries.
  • adhesive tapes for covering must withstand high temperatures during industrial painting processes and can later be removed again without leaving any residue. With jackets and bundles, however, high strength and low elongation are important. On the other hand, high immediate adhesive strength is required when changing rolls in the paper industry. Outside of industrial application areas, these products are mainly used in schools, at home, in the office or in the do-it-yourself sector.
  • the adhesives according to the invention can contain one or more of the following constituents, a distinction being made fundamentally between adhesives based on natural and synthetic raw materials, combinations of these raw materials also being possible. Suitable raw materials are known to the person skilled in the art.
  • compositions of the adhesives in particular for use in medicine, e.g. as an adhesive for application to the skin of humans or animals are disclosed, for example, in EP-A 0 928 207.
  • 1,2-Diisobutylcyclohexanedicarboxylic acid ester is preferably used in the adhesives mentioned or as adhesives.
  • 1,2-cyclohexanedicarboxylic acid esters used according to the invention are selected from the group consisting of 1,2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester as a plasticizer for impact strength - difier, preferably for impact modifiers for thermoplastics, for example for polyamide.
  • Suitable amounts in which the at least one 1,2-cyclohexanedicarboxylic acid ester used according to the invention is used are the amounts customary for plasticizers and are therefore known to the person skilled in the art.
  • 1,2-Di- (2-ethylhexyl) cyclohexanedicarboxylic acid esters and 1,2-diisononylcyclohexanedicarboxylic acid esters are preferably used in the impact modifiers or as impact modifiers.
  • 1, 2-cyclohexanedicarboxylic acid esters used according to the invention can be selected from the group consisting of 1, 2-diisobutylcyclohexanedicarboxylic acid ester, 1,2-di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1, 2-diisononyIcycIohexanedicarboxylic acid ester as auxiliary agents in the Production of detergents can be used, for example as a setting agent, to keep detergent powder free-flowing and to bring it into an application-appropriate state.
  • Geeigne- te amounts correspond to the amounts of adjusting agents usually used in detergents and are known to the person skilled in the art.
  • 1,2-Di- (2-ethylhexyl) cyclohexanedicarboxylic acid ester and 1,2-diisononylcyclohexanedicarboxylic acid ester are preferably used in the detergents.
  • auxiliaries according to the invention which contain the 1,2-cyclohexanedicarboxylic acid esters used according to the invention are prepared in each case by processes known to the person skilled in the art.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Dental Preparations (AREA)
  • Lubricants (AREA)

Abstract

Utilisation d'esters d'acide 1,2-cyclohexane dicarboxylique choisi dans le groupe constitué par ester d'acide 1,2-diisobutylcyclohexane dicarboxylique, ester d'acide 1,2-di-(2-éthylhexyl)-cyclohexane dicarboxylique et ester d'acide 1,2-diisononylcyclohexane dicarboxylique dans des adjuvants ou en tant qu'adjuvants choisis dans le groupe constitué des adjuvants suivants: compositions tensioactives choisies parmi adjuvants de fluidité, adjuvants filmogènes, agents antimoussants, inhibiteurs de formation de mousse, agents de mouillage, agents de coalescence et émulsifiants ; lubrifiants choisis parmi les huiles lubrifiantes, les graisses lubrifiantes et les pâtes lubrifiantes ; adjuvants de calandrage ; adjuvants rhéologiques, agents d'extinction pour des réactions chimiques ; agents de stabilisation d'explosifs ; produits pharmaceutiques ; plastifiants dans des adhésifs ; modificateurs de résistance aux chocs et agents de fixation. La présente invention concerne également des compositions tensioactives, des adjuvants de calandrage, des adjuvants rhéologiques, des agents d'extinction pour des réactions chimiques, des agents de stabilisation d'explosifs, des produits pharmaceutiques, des plastifiants dans des adhésifs, des modificateurs de résistance aux chocs et des agents de fixation contenant des dérivés d'acide cyclohexane polycarboxylique.
EP05769030A 2004-06-21 2005-06-21 Adjuvants contenant des derives d'acide cyclohexane polycarboxylique Withdrawn EP1761596A2 (fr)

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EP10177776.1A EP2377844B1 (fr) 2004-06-21 2005-06-21 Moyen d'aide contenant des dérivés d'acide cyclohexane-polycarboxylique

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DE102004029732A DE102004029732A1 (de) 2004-06-21 2004-06-21 Hilfsmittel enthaltend Cyclohexanpolycarbonsäurederivate
PCT/EP2005/006682 WO2005123821A2 (fr) 2004-06-21 2005-06-21 Adjuvants contenant des dérivés d'acide cyclohexane polycarboxylique

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EP10177776.1A Previously-Filed-Application EP2377844B1 (fr) 2004-06-21 2005-06-21 Moyen d'aide contenant des dérivés d'acide cyclohexane-polycarboxylique

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CN (1) CN1989194A (fr)
CA (1) CA2570201C (fr)
DE (1) DE102004029732A1 (fr)
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CA2570201A1 (fr) 2005-12-29
ES2656138T3 (es) 2018-02-23
US20080039646A1 (en) 2008-02-14
CN1989194A (zh) 2007-06-27
DE102004029732A1 (de) 2006-01-19
WO2005123821A2 (fr) 2005-12-29
EP2377844B1 (fr) 2017-10-18
KR101169821B1 (ko) 2012-07-30
CA2570201C (fr) 2013-12-10
WO2005123821A3 (fr) 2006-09-08
MY146104A (en) 2012-06-29
JP2008503525A (ja) 2008-02-07
KR20070033362A (ko) 2007-03-26
JP4714215B2 (ja) 2011-06-29
EP2377844A3 (fr) 2012-05-16
US7816553B2 (en) 2010-10-19

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