WO2017215747A1 - 2-ocytlester as plasticizer - Google Patents

2-ocytlester as plasticizer Download PDF

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Publication number
WO2017215747A1
WO2017215747A1 PCT/EP2016/063741 EP2016063741W WO2017215747A1 WO 2017215747 A1 WO2017215747 A1 WO 2017215747A1 EP 2016063741 W EP2016063741 W EP 2016063741W WO 2017215747 A1 WO2017215747 A1 WO 2017215747A1
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WO
WIPO (PCT)
Prior art keywords
composition according
acid
octyl
alcohol
carboxylic acid
Prior art date
Application number
PCT/EP2016/063741
Other languages
French (fr)
Inventor
Peter Daute
Martin Schaefer
Original Assignee
Emery Oleochemicals Gmbh
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Publication date
Application filed by Emery Oleochemicals Gmbh filed Critical Emery Oleochemicals Gmbh
Priority to PCT/EP2016/063741 priority Critical patent/WO2017215747A1/en
Publication of WO2017215747A1 publication Critical patent/WO2017215747A1/en

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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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0016—Plasticisers
    • 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
    • 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
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids

Definitions

  • the present invention relates to a composition
  • a composition comprising at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and use of the at least one ester as plasticizer in thermoplastic polymer compositions.
  • Plasticizers can be modified by the usage of plasticizers. Flexible, plastic masses can be obtained thereby.
  • the amount of plasticizers can be so high that the PVC compositions can be processed as paste (Gachter/Muller,
  • WO 2014/209644 Al discloses self-wetting adhesive compositions.
  • JP 2012-020984 A discloses ester derivatives and cosmetic containing the ester derivatives, external preparation, coating material and ink composition.
  • thermoplastic polymer composition with improved properties and additionally (ii) a plasticizer with improved properties used in thermoplastic polymer compositions.
  • esters of 2-octanol which is obtainable from castor oil have excellent plasticizing properties. Additionally, the esters of 2- octanol have a surprisingly good compatibility with the polymers as defined herein. With said esters good plasticizing and low temperature properties of thermoplastic polymer compositions are obtained. Also exceptional is the stability of the esters to hydrolysis which is distinctly higher than that of plasticizer usually used in the state of the art.
  • the present invention provides a composition comprising:
  • At least one carboxylic acid ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol;
  • thermoplastic polymer (b) at least one thermoplastic polymer.
  • a further aspect of the invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition as defined herein.
  • a further aspect of the invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition as defined herein.
  • the at least one carboxylic acid comprises at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six carboxylic acid groups, preferably 1 to 6 carboxylic acid groups, preferably 1 or 2 carboxylic acid groups.
  • the at least one carboxylic acid is selected from the group consisting of a mono-, di-, tri-, tetra-, penta-, hexa- and polycarboxylic acid and any mixture thereof.
  • the at least one carboxylic acid is a CI to C30 carboxylic acid, preferably a C2 to C20 carboxylic acid, preferably a C4 to C18 carboxylic acid, preferably a C4, C5, C6, C7, C8, C9, CIO, Cl l, C12, C13, C14, C15, C16, C17 or C18 carboxylic acid, preferably a C4, C5, C8, C9, CIO, C12, C14, C16, or C18 carboxylic acid.
  • Cx carboxylic acid means that the carboxylic acid comprises x carbon atom(s), including the carbon atom(s) of the carboxyl group(s).
  • a C4 carboxylic acid is preferably succinic acid (C 4 H 6 O 4 ).
  • the at least one carboxylic acid is a saturated or unsaturated carboxylic acid.
  • the at least one carboxylic acid is an aliphatic and/or aromatic carboxylic acid.
  • the at least one carboxylic acid is a linear or branched carboxylic acid.
  • the unsaturated carboxylic acid comprises at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably 1, 2, 3, 4, 5, or 6 double bounds.
  • the at least one carboxylic acid comprises a saturated or unsaturated chain, by which the carboxyl groups are preferably linked.
  • the at least one carboxylic acid comprises a linear or branched chain, by which the carboxyl groups are preferably linked.
  • the at least one carboxylic acid comprises an aliphatic and/or aromatic chain, by which the carboxyl groups are preferably linked.
  • the at least one carboxylic acid comprises a saturated or unsaturated, linear or branched aliphatic chain and/or ring.
  • the at least one carboxylic acid comprises additionally or alternatively at least one aromatic ring.
  • the carboxylic acid has an aliphatic or aromatic structure which is branched or unbranched and comprises from 1 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, particularly preferably from 4 to 18 carbon atoms, including the carbon atoms of the one or more carboxyl groups.
  • the carbon atoms are bound directly to one another via single or double bonds in the aliphatic or aromatic structure.
  • the aliphatic structure preferably has solely single bonds between the carbon atoms.
  • the at least one carboxylic acid comprises an carbon chain, by which the carboxyl groups are preferably linked, wherein preferably at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably at most half of the carbon atoms, preferably 1, 2, 3, 4, 5 or 6 carbon atoms are substituted by the same or different hetero atoms, wherein the hetero atoms are preferably selected form nitrogen, sulfur and oxygen.
  • the carbon chain is free of heteroatoms.
  • the at least one carboxylic acid consists of at least one, preferably exactly one saturated or unsaturated, aliphatic and/or aromatic, linear or branched hydrocarbon chain and/or ring and at least one carboxylic acid group COOH.
  • the present invention relates to a composition according to the present invention, wherein the at least one carboxylic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids and any mixture thereof.
  • the present invention relates to a composition according to the present invention, wherein the monocarboxylic acids are selected from the group consisting of fatty acids.
  • the monocarboxylic acids preferably the fatty acids are obtainable from renewable materials.
  • the at least one monocarboxylic acid is an unsaturated fatty acid, a saturated fatty acid or any mixture thereof.
  • the saturated fatty acid is preferably a saturated C12 to C18 fatty acid.
  • the unsaturated fatty acid is preferably an unsaturated C12 to C18 fatty acid with one, two, three, four, five or six double bonds, preferably with exactly one double bond.
  • the at least one monocarboxylic acid is stearic acid, palmitic acid, oleic acid, lauric acid, myristic acid and any mixture thereof.
  • the at least one dicarboxylic acid is an alkane dicarboxylic acid, an alkene dicarboxylic acid or any mixture thereof.
  • the alkane dicarboxylic acid is preferably a C2 to CIO alkane dicarboxylic acid.
  • the alkene dicarboxylic acid is preferably a C4 to CIO alkene dicarboxylic acid with one, two or three double bonds.
  • the at least one dicarboxylic acid is an alkane dicarboxylic acid.
  • the present invention relates to a composition according to the present invention, wherein the dicarboxylic acids are selected from the group consisting of succinic acid, azelaic acid, sebacic acid, glutaric acid, suberic acid, adipic acid and any mixture thereof.
  • the dicarboxylic acids are selected from the group consisting of succinic acid, azelaic acid, sebacic acid, glutaric acid, suberic acid, adipic acid and any mixture thereof.
  • succinic acid, azelaic acid and/or sebacic acid are produced from a renewable material.
  • succinic acid is produced by fermentation of carbohydrates, preferably of starch.
  • azelaic acid is produced by ozonolysis of oleic acid.
  • sebacic acid is produced by pyrolysis of castor oil, preferably of ricinoleic acid or derivatives thereof.
  • the at least one carboxylic acid ester is obtainable by reacting at least one carboxylic acid with 2-octanol and at least one further alcohol.
  • the 2-octanol is reacted with the at least one carboxylic acid in form of a product, preferably obtained from a technical production process, which product comprises the 2-octanol in an amount of at least 50 % by weight, preferably at least 70 % by weight, preferably at least 80 % by weight, preferably at least 90% by weight, preferably at least 99 % by weight (based on the total weight of the product).
  • the present invention relates to a composition according to the present invention, wherein at least 50 mol-%, preferably at least 70 mol-%, preferably at least 80 mol-%, preferably at least 90 mol-%, preferably at least 99 mol-%, preferably 100 mol-% of the at least one alcohol is 2-octanol (based on the total amount of alcohols reacted with the at least one carboxylic acid).
  • the at least one further alcohol comprises at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six hydroxyl groups, preferably 1 to 6 hydroxyl groups, preferably 1, 2, 3, 4, 5, or 6 hydroxyl groups, preferably exactly one hydroxyl group.
  • the at least one further alcohol is a CI to C30 alcohol, preferably a C2 to C20 alcohol, preferably a C8 to C12 alcohol, preferably a C8, C9, CIO, Cl l or C12 alcohol, preferably a C8, CIO, or C12 alcohol.
  • the at least one further alcohol is a saturated or unsaturated alcohol.
  • the at least one further alcohol is an aliphatic and/or aromatic alcohol.
  • the at least one further alcohol is a linear or branched alcohol.
  • the unsaturated at least one further alcohol comprises at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably 1, 2, 3, 4, 5, or 6 double bounds.
  • the at least one further alcohol comprises a saturated or unsaturated chain.
  • the at least one further alcohol comprises a linear or branched chain.
  • the at least one further alcohol comprises a saturated or unsaturated chain which is linear or branched.
  • the at least one further alcohol comprises a saturated or unsaturated, linear or branched aliphatic chain and/or ring.
  • the at least one further alcohol comprises additionally or alternatively at least one aromatic ring.
  • the further alcohol has an aliphatic or aromatic structure which is branched or linear and comprises from 1 to 30 carbon atoms, more preferably from 8 to 12 carbon atoms.
  • the carbon atoms are bound directly to one another via single or double bonds in the aliphatic or aromatic structure.
  • the aliphatic structure preferably has solely single bonds between the carbon atoms.
  • the at least one further alcohol comprises an carbon chain, wherein preferably at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably at most half of the carbon atoms, preferably 1, 2, 3, 4, 5 or 6 carbon atoms are substituted by the same or different hetero atoms, wherein the hetero atoms are preferably selected form nitrogen, sulfur and oxygen.
  • the carbon chain is free of heteroatoms.
  • the at least one further alcohol consists of at least one, preferably exactly one saturated or unsaturated, aliphatic and/or aromatic, linear or branched hydrocarbon chain and/or ring and at least one hydroxyl group OH.
  • the at least one further alcohol is an alcohol produced from renewable materials.
  • the at least one further alcohol is preferably an aliphatic, preferably an alkyl, alcohol, preferably with 8, 10 or 12 carbon atoms, preferably a C8, CIO or C12 alkyl monoalcohol, or any mixture thereof.
  • the at least one carboxylic acid ester is obtainable by reacting a mono-, di-, tri-, tetra-, penta-, hexa- or polycarboxylic acid with one, two, three, four, five, six or more different alcohols, wherein the one or one of the two, three, four, five, six or more different alcohols is 2-octanol.
  • the alcohol different from 2-octanol is preferably an aliphatic, preferably an alkyl, alcohol, preferably with 8, 10 or 12 carbon atoms, preferably a C8, CIO or C12 alkyl monoalcohol, or any mixture thereof.
  • the alcohol different from 2-octanol is producible from renewable materials.
  • the at least one carboxylic acid ester is obtainable by reacting at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six, preferably (n - 3), preferably (n - 2), preferably (n - 1), preferably n carboxyl groups of the at least one carboxylic acid having n carboxyl groups.
  • all carboxyl groups of the at least one carboxylic acid have been reacted, i.e. esterfied, with 2-octanol and optionally with at least one further alcohol.
  • the at least one carboxylic acid ester is obtainable by reacting a monocarboxylic acid with an alcohol, wherein the alcohol is 2-octanol.
  • the at least one carboxylic acid ester is preferably obtainable by reacting a dicarboxylic acid with two different alcohols, wherein one of the two different alcohols is 2-octanol.
  • the at least one carboxylic acid ester is preferably obtainable by reacting a dicarboxylic acid with exactly one alcohol, wherein the alcohol is 2-octanol.
  • the at least one ester consists of
  • the composition comprises at least two, preferably at least three different esters according to the present invention. More preferably, the composition comprises exactly one or two, preferably exactly one ester according to the present invention.
  • the present invention relates to a composition according to the present invention, wherein the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di-2-octyl suberate, di- 2-octyl adipate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof.
  • the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di-2-octyl suberate, di- 2-octyl adipate, 2-octy
  • the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, 2-octyl stearate, 2- octyl palmitate, 2-octyl oleate and any mixture thereof.
  • the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate and any mixture thereof.
  • these esters can exclusively be obtained from renewable materials.
  • the present invention relates to a composition according to the present invention, wherein the at least one alcohol and optionally the at least one carboxylic acid have been obtained from a renewable source.
  • the 2-octanol is produced by the pyrolysis of castor oil, preferably of ricinoleic acid or derivatives thereof. Castor oil is a renewable source for 2-octanol.
  • the present invention relates to a composition according to the present invention, wherein the at least one ester has a high stability to hydrolysis.
  • the at least one ester has a higher stability to hydrolysis than an ester comprising the same carboxylic acid component and a different alcohol component, wherein the alcohol component is preferably selected from a group consisting of 1-octanol and 2-ethylhexanol.
  • the present invention relates to a composition according to the present invention, wherein the at least one thermoplastic polymer is selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof.
  • the at least one thermoplastic polymer is polyvinyl chloride (PVC).
  • the polyvinyl chloride (PVC) has a molecular weight (M w ) of 20.000 to 300.000 g/mol, preferably 100.000 to 200.000 g/mol.
  • the present invention relates to a composition according to the present invention, wherein the at least one rubber is a synthetic rubber.
  • the synthetic rubber has a molecular weight (M w ) of 50.000 to 500.000 g/mol, preferably 200.000 to 300.000 g/mol.
  • the present invention relates to a composition according to the present invention, wherein the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
  • NBR acrylonitrile butadiene rubber
  • BR polybutadiene rubber
  • CIIR chloro isobutylene isoprene rubber
  • CSM chlorosulfonated polyethylene
  • CR chloroprene rubber
  • PIB polyisobutylene rubber
  • IR fluorinated rubber
  • FKM fluorinated rubber
  • the present invention relates to a composition according to the present invention, wherein the content of polymers of methacrylate and/or acrylate is less than 50 % by weight.
  • the composition is preferably free of methacrylate and/or acrylate in monomer and/or polymer form.
  • the composition comprises
  • At least one carboxylic acid ester selected from the group consisting of di-2- octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di- 2-octyl suberate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof; and
  • thermoplastic polymer selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof
  • the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
  • composition comprises
  • the composition comprises at least two, preferably at least three different plasticizers.
  • the composition comprises exactly two different plasticizers.
  • the composition comprises the at least one ester and an epoxy plasticizer as plasticizers.
  • the composition further comprises at least one fatty acid ester which is different from the at least one ester according to the present invention, preferably an epoxidized soybean oil.
  • the composition further comprises a stabilizing agent, preferably a Sn stabilizer, and/or a lubricant.
  • a stabilizing agent preferably a Sn stabilizer, and/or a lubricant.
  • the composition is solid at a temperature of 22 °C.
  • the composition is free of a cross-linked polymer, preferably a cross-linked thermoplastic polymer, or comprises a cross-linked polymer, preferably a cross-linked thermoplastic polymer, in an amount of 50 % by weight or less, preferably 40 % by weight or less, preferably 30 % by weight or less, preferably 10% by weight or less, preferably 5% by weight or less, preferably 1 % by weight or less (based on the total weight of polymers in the composition).
  • the at least one rubber is cross-linked, preferably vulcanized.
  • the PVC is not cross-linked.
  • the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 0.1 to 60 % by weight (based on the total weight of the composition).
  • the at least one ester (a) is present in an amount of 10 to 50 % by weight, preferably 20 to 40 % by weight (based on the total weight of the composition).
  • the present invention relates to a composition according to the present invention, wherein the at least one polymer (b) is present in an amount of at least 40 % by weight (based on the total amount of the composition).
  • the at least one polymer (b) is present in an amount of at least 50 % by weight, preferably at least 60 % by weight, preferably at least 80 % by weight (based on the total amount of the composition).
  • the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 100 parts or less per 100 parts of resin.
  • the at least one ester (a) is present in an amount of 80 parts or less, preferably 60 to 20 parts per 100 parts of resin.
  • the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 100 parts or less per 100 parts of the thermoplastic polymer (b).
  • the at least one ester (a) is present in an amount of 80 parts or less, preferably 60 to 20 parts per 100 parts of the thermoplastic polymer (b).
  • the present invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid and at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition as defined herein.
  • the at least one ester is used for plasticizing at least one thermoplastic polymer, preferably polyvinyl chloride (PVC), at least one rubber and any mixture thereof, wherein the at least one rubber is preferably a synthetic rubber, wherein the synthetic rubber is preferably selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
  • the at least one ester is used for plasticizing polyvinyl chloride (PVC).
  • the present invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition as defined herein.
  • any technical feature, either alone or in combination with one or more further technical features, disclosed in context with the composition according to the present invention or according to one or more preferred embodiments is also preferably a technical feature for specifying the uses according to the present invention and/or one or more of their preferred embodiments.
  • any technical feature, either alone or in combination with one or more further technical features, disclosed in context with the composition according to the present invention or according to one or more preferred embodiments is also preferably a technical feature for specifying the uses according to the present invention and/or one or more of their preferred embodiments.
  • the alcohol, the carboxylic acid (each in the amount as listed in table 1, below) and 0.3 g tin- (Il)-oxalate (Goldschmidt) were heated under nitrogen atmosphere.
  • the ester reaction starts at about 170 °C with the production of water. After 3 hours the produced water was removed by applying vacuum and the vacuum was reduced within 4 hours up to about 15 mbar. The final reaction temperature was reached at about 230 °C. After having reached an acid number of less than 1, the excessive alcohol was distilled and the ester was cooled to a temperature of 90 °C, washed with 300 ml water for removing the catalyst, dried and filtered with 2 g bleaching earth (Tonsil, Sudchemie) being added.
  • the produced esters have the following properties/characteristics as shown in table 2, below.
  • Table 4 shows that by using the plasticizers of Examples 4 to 6, namely di-2-octyl succinate, di-2-octyl sebacate and di-2-octyl azelate, the same properties of PVC were obtained as by di-2-ethylhexyladipate (DOA), used an industrial standard.
  • DOA di-2-ethylhexyladipate

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Abstract

The present invention relates to a composition comprising at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and use of the at least one ester as plasticizer in thermoplastic polymer compositions.

Description

2-OCYTLESTER AS PLASTICIZER
The present invention relates to a composition comprising at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and use of the at least one ester as plasticizer in thermoplastic polymer compositions.
BACKGROUND OF THE INVENTION
Material properties of plastics can be modified by the usage of plasticizers. Flexible, plastic masses can be obtained thereby. In PVC compositions the amount of plasticizers can be so high that the PVC compositions can be processed as paste (Gachter/Muller,
Kunststoffadditive, 2nd edition, publisher: Carl Hanser Verlag). Recently, many companies attach importance to the usage of additives based on renewable materials. Some companies offer "green plasticizers" partially or completely produced from renewable materials, e.g. GRINDSTED® SOFT-N-SAFE of Danisco (http://www.danisco.com/softnsafe/doc/ snsbrochure.pdf) or isosorbid esters as disclosed in DE69906708T2. In addition to monocarboxylic acids, dicarboxylic acids are sold, which can be produced from renewable materials, such as fatty acids, succinic acid, sebacic acid and azelaic acid. The selection of renewable alcohols is nowadays restricted to n-C8 to n-C18 fatty alcohols, ethanol, 1,2- propandiol and butanol.
WO 2014/209644 Al discloses self-wetting adhesive compositions.
JP 2012-020984 A discloses ester derivatives and cosmetic containing the ester derivatives, external preparation, coating material and ink composition.
It was an object to the present invention to solve the aforementioned problems and preferably to provide (i) a thermoplastic polymer composition with improved properties and additionally (ii) a plasticizer with improved properties used in thermoplastic polymer compositions. SUMMARY OF THE INVENTION
It was an unexpected finding of the inventors that the esters of 2-octanol which is obtainable from castor oil have excellent plasticizing properties. Additionally, the esters of 2- octanol have a surprisingly good compatibility with the polymers as defined herein. With said esters good plasticizing and low temperature properties of thermoplastic polymer compositions are obtained. Also exceptional is the stability of the esters to hydrolysis which is distinctly higher than that of plasticizer usually used in the state of the art.
Thus, to solve the aforementioned problems, the present invention provides a composition comprising:
(a) at least one carboxylic acid ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and
(b) at least one thermoplastic polymer.
A further aspect of the invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition as defined herein.
A further aspect of the invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition as defined herein.
The technical problem has been, in particular, solved by the subject-matter of the independent claims. Preferred embodiments are the subject-matter of the dependent claims. DETAILED DESCRIPTION OF THE INVENTION
Before the present invention is described in detail below, it is to be understood that this invention is not limited to the particular methodology, protocols and reagents described herein as these may vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention which will be limited only by the appended claims. Unless defined otherwise, all technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art.
In the following passages different aspects of the invention are defined in more detail. Each aspect so defined may be combined with any other aspect or aspects unless clearly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features indicated as being preferred or advantageous.
Some documents are cited throughout the text of this specification. Each of the documents cited herein (including all patents, patent applications, scientific publications, manufacturer's specifications, instructions, DIN norms etc.), whether supra or infra, are hereby incorporated by reference in their entirety. Nothing herein is to be construed as an admission that the invention is not entitled to antedate such disclosure by virtue of prior invention.
In the following definitions of some terms are provided. These terms will, in each instance of its use, in the remainder of the specification have the respectively defined meaning and preferred meanings.
With the term "and/or" all members of a corresponding group are connected to each other alternatively, partially or completely commutatively. For instance, the term "A, B and/or C" is understood as "A or B or C or (A and B) or (A and C) or (B and C) or (A and B and O".
Preferably, the at least one carboxylic acid comprises at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six carboxylic acid groups, preferably 1 to 6 carboxylic acid groups, preferably 1 or 2 carboxylic acid groups. Preferably, the at least one carboxylic acid is selected from the group consisting of a mono-, di-, tri-, tetra-, penta-, hexa- and polycarboxylic acid and any mixture thereof.
Preferably, the at least one carboxylic acid is a CI to C30 carboxylic acid, preferably a C2 to C20 carboxylic acid, preferably a C4 to C18 carboxylic acid, preferably a C4, C5, C6, C7, C8, C9, CIO, Cl l, C12, C13, C14, C15, C16, C17 or C18 carboxylic acid, preferably a C4, C5, C8, C9, CIO, C12, C14, C16, or C18 carboxylic acid. In the context with the present invention the term "Cx carboxylic acid" means that the carboxylic acid comprises x carbon atom(s), including the carbon atom(s) of the carboxyl group(s). Accordingly, a C4 carboxylic acid is preferably succinic acid (C4H6O4).
Preferably, the at least one carboxylic acid is a saturated or unsaturated carboxylic acid. Preferably, the at least one carboxylic acid is an aliphatic and/or aromatic carboxylic acid. Preferably, the at least one carboxylic acid is a linear or branched carboxylic acid. Preferably, the unsaturated carboxylic acid comprises at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably 1, 2, 3, 4, 5, or 6 double bounds.
Preferably, the at least one carboxylic acid comprises a saturated or unsaturated chain, by which the carboxyl groups are preferably linked. Preferably, the at least one carboxylic acid comprises a linear or branched chain, by which the carboxyl groups are preferably linked. Preferably, the at least one carboxylic acid comprises an aliphatic and/or aromatic chain, by which the carboxyl groups are preferably linked.
Preferably, the at least one carboxylic acid comprises a saturated or unsaturated, linear or branched aliphatic chain and/or ring. Preferably, the at least one carboxylic acid comprises additionally or alternatively at least one aromatic ring.
In a preferred embodiment, the carboxylic acid has an aliphatic or aromatic structure which is branched or unbranched and comprises from 1 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, particularly preferably from 4 to 18 carbon atoms, including the carbon atoms of the one or more carboxyl groups. The carbon atoms are bound directly to one another via single or double bonds in the aliphatic or aromatic structure. The aliphatic structure preferably has solely single bonds between the carbon atoms. Preferably, the at least one carboxylic acid comprises an carbon chain, by which the carboxyl groups are preferably linked, wherein preferably at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably at most half of the carbon atoms, preferably 1, 2, 3, 4, 5 or 6 carbon atoms are substituted by the same or different hetero atoms, wherein the hetero atoms are preferably selected form nitrogen, sulfur and oxygen. Preferably, the carbon chain is free of heteroatoms. Preferably, the at least one carboxylic acid consists of at least one, preferably exactly one saturated or unsaturated, aliphatic and/or aromatic, linear or branched hydrocarbon chain and/or ring and at least one carboxylic acid group COOH.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one carboxylic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids and any mixture thereof.
Preferably, the present invention relates to a composition according to the present invention, wherein the monocarboxylic acids are selected from the group consisting of fatty acids. Preferably, the monocarboxylic acids, preferably the fatty acids are obtainable from renewable materials. Preferably, the at least one monocarboxylic acid is an unsaturated fatty acid, a saturated fatty acid or any mixture thereof. The saturated fatty acid is preferably a saturated C12 to C18 fatty acid. The unsaturated fatty acid is preferably an unsaturated C12 to C18 fatty acid with one, two, three, four, five or six double bonds, preferably with exactly one double bond. Preferably, the at least one monocarboxylic acid is stearic acid, palmitic acid, oleic acid, lauric acid, myristic acid and any mixture thereof.
Preferably, the at least one dicarboxylic acid is an alkane dicarboxylic acid, an alkene dicarboxylic acid or any mixture thereof. The alkane dicarboxylic acid is preferably a C2 to CIO alkane dicarboxylic acid. The alkene dicarboxylic acid is preferably a C4 to CIO alkene dicarboxylic acid with one, two or three double bonds. Preferably, the at least one dicarboxylic acid is an alkane dicarboxylic acid.
Preferably, the present invention relates to a composition according to the present invention, wherein the dicarboxylic acids are selected from the group consisting of succinic acid, azelaic acid, sebacic acid, glutaric acid, suberic acid, adipic acid and any mixture thereof.
Preferably, succinic acid, azelaic acid and/or sebacic acid are produced from a renewable material. Preferably, succinic acid is produced by fermentation of carbohydrates, preferably of starch. Preferably, azelaic acid is produced by ozonolysis of oleic acid. Preferably, sebacic acid is produced by pyrolysis of castor oil, preferably of ricinoleic acid or derivatives thereof.
Preferably, the at least one carboxylic acid ester is obtainable by reacting at least one carboxylic acid with 2-octanol and at least one further alcohol.
Preferably, the 2-octanol is reacted with the at least one carboxylic acid in form of a product, preferably obtained from a technical production process, which product comprises the 2-octanol in an amount of at least 50 % by weight, preferably at least 70 % by weight, preferably at least 80 % by weight, preferably at least 90% by weight, preferably at least 99 % by weight (based on the total weight of the product).
Preferably, the present invention relates to a composition according to the present invention, wherein at least 50 mol-%, preferably at least 70 mol-%, preferably at least 80 mol-%, preferably at least 90 mol-%, preferably at least 99 mol-%, preferably 100 mol-% of the at least one alcohol is 2-octanol (based on the total amount of alcohols reacted with the at least one carboxylic acid).
Preferably, the at least one further alcohol comprises at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six hydroxyl groups, preferably 1 to 6 hydroxyl groups, preferably 1, 2, 3, 4, 5, or 6 hydroxyl groups, preferably exactly one hydroxyl group.
Preferably, the at least one further alcohol is a CI to C30 alcohol, preferably a C2 to C20 alcohol, preferably a C8 to C12 alcohol, preferably a C8, C9, CIO, Cl l or C12 alcohol, preferably a C8, CIO, or C12 alcohol.
Preferably, the at least one further alcohol is a saturated or unsaturated alcohol. Preferably, the at least one further alcohol is an aliphatic and/or aromatic alcohol. Preferably, the at least one further alcohol is a linear or branched alcohol. Preferably, the unsaturated at least one further alcohol comprises at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably 1, 2, 3, 4, 5, or 6 double bounds.
Preferably, the at least one further alcohol comprises a saturated or unsaturated chain. Preferably, the at least one further alcohol comprises a linear or branched chain. Preferably, the at least one further alcohol comprises a saturated or unsaturated chain which is linear or branched.
Preferably, the at least one further alcohol comprises a saturated or unsaturated, linear or branched aliphatic chain and/or ring. Preferably, the at least one further alcohol comprises additionally or alternatively at least one aromatic ring.
In a preferred embodiment, the further alcohol has an aliphatic or aromatic structure which is branched or linear and comprises from 1 to 30 carbon atoms, more preferably from 8 to 12 carbon atoms. The carbon atoms are bound directly to one another via single or double bonds in the aliphatic or aromatic structure. The aliphatic structure preferably has solely single bonds between the carbon atoms.
Preferably, the at least one further alcohol comprises an carbon chain, wherein preferably at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably at most half of the carbon atoms, preferably 1, 2, 3, 4, 5 or 6 carbon atoms are substituted by the same or different hetero atoms, wherein the hetero atoms are preferably selected form nitrogen, sulfur and oxygen. Preferably, the carbon chain is free of heteroatoms. Preferably, the at least one further alcohol consists of at least one, preferably exactly one saturated or unsaturated, aliphatic and/or aromatic, linear or branched hydrocarbon chain and/or ring and at least one hydroxyl group OH.
Preferably, the at least one further alcohol is an alcohol produced from renewable materials. The at least one further alcohol is preferably an aliphatic, preferably an alkyl, alcohol, preferably with 8, 10 or 12 carbon atoms, preferably a C8, CIO or C12 alkyl monoalcohol, or any mixture thereof.
Preferably, the at least one carboxylic acid ester is obtainable by reacting a mono-, di-, tri-, tetra-, penta-, hexa- or polycarboxylic acid with one, two, three, four, five, six or more different alcohols, wherein the one or one of the two, three, four, five, six or more different alcohols is 2-octanol. Preferably, the alcohol different from 2-octanol is preferably an aliphatic, preferably an alkyl, alcohol, preferably with 8, 10 or 12 carbon atoms, preferably a C8, CIO or C12 alkyl monoalcohol, or any mixture thereof. Preferably, the alcohol different from 2-octanol is producible from renewable materials.
Preferably, the at least one carboxylic acid ester is obtainable by reacting at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six, preferably (n - 3), preferably (n - 2), preferably (n - 1), preferably n carboxyl groups of the at least one carboxylic acid having n carboxyl groups. Preferably, all carboxyl groups of the at least one carboxylic acid have been reacted, i.e. esterfied, with 2-octanol and optionally with at least one further alcohol.
Preferably, the at least one carboxylic acid ester is obtainable by reacting a monocarboxylic acid with an alcohol, wherein the alcohol is 2-octanol. Alternatively, the at least one carboxylic acid ester is preferably obtainable by reacting a dicarboxylic acid with two different alcohols, wherein one of the two different alcohols is 2-octanol. Alternatively, the at least one carboxylic acid ester is preferably obtainable by reacting a dicarboxylic acid with exactly one alcohol, wherein the alcohol is 2-octanol.
Preferably, the at least one ester consists of
(i) a mono-, di-, tri-, tetra-, penta-, hexa- or polycarboxylic acid
component, and
(ii) 2-octanol as alcohol component.
Preferably, the composition comprises at least two, preferably at least three different esters according to the present invention. More preferably, the composition comprises exactly one or two, preferably exactly one ester according to the present invention.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di-2-octyl suberate, di- 2-octyl adipate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof. Preferably, the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, 2-octyl stearate, 2- octyl palmitate, 2-octyl oleate and any mixture thereof. Preferably, the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate and any mixture thereof. Preferably, these esters can exclusively be obtained from renewable materials.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one alcohol and optionally the at least one carboxylic acid have been obtained from a renewable source. Preferably, the 2-octanol is produced by the pyrolysis of castor oil, preferably of ricinoleic acid or derivatives thereof. Castor oil is a renewable source for 2-octanol.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester has a high stability to hydrolysis. Preferably, the at least one ester has a higher stability to hydrolysis than an ester comprising the same carboxylic acid component and a different alcohol component, wherein the alcohol component is preferably selected from a group consisting of 1-octanol and 2-ethylhexanol.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one thermoplastic polymer is selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof. Preferably, the at least one thermoplastic polymer is polyvinyl chloride (PVC).
Preferably, the polyvinyl chloride (PVC) has a molecular weight (Mw) of 20.000 to 300.000 g/mol, preferably 100.000 to 200.000 g/mol.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one rubber is a synthetic rubber.
Preferably, the synthetic rubber has a molecular weight (Mw) of 50.000 to 500.000 g/mol, preferably 200.000 to 300.000 g/mol.
Preferably, the present invention relates to a composition according to the present invention, wherein the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
Preferably, the present invention relates to a composition according to the present invention, wherein the content of polymers of methacrylate and/or acrylate is less than 50 % by weight. Alternatively, the composition is preferably free of methacrylate and/or acrylate in monomer and/or polymer form.
Preferably, the composition comprises
(a) at least one carboxylic acid ester selected from the group consisting of di-2- octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di- 2-octyl suberate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof; and
(b) at least one thermoplastic polymer selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof, the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
More preferably, the composition comprises
(a) at least one carboxylic acid ester selected from the group consisting of di-2- octyl succinate, di-2-octyl sebacate, di-2-octyl azelate and any mixture thereof; and
(b) polyvinyl chloride (PVC).
Preferably, the composition comprises at least two, preferably at least three different plasticizers. Preferably, the composition comprises exactly two different plasticizers. Preferably, the composition comprises the at least one ester and an epoxy plasticizer as plasticizers.
Preferably, the composition further comprises at least one fatty acid ester which is different from the at least one ester according to the present invention, preferably an epoxidized soybean oil.
Preferably, the composition further comprises a stabilizing agent, preferably a Sn stabilizer, and/or a lubricant.
Preferably, the composition is solid at a temperature of 22 °C.
Preferably, the composition is free of a cross-linked polymer, preferably a cross-linked thermoplastic polymer, or comprises a cross-linked polymer, preferably a cross-linked thermoplastic polymer, in an amount of 50 % by weight or less, preferably 40 % by weight or less, preferably 30 % by weight or less, preferably 10% by weight or less, preferably 5% by weight or less, preferably 1 % by weight or less (based on the total weight of polymers in the composition).
Preferably, the at least one rubber is cross-linked, preferably vulcanized. Preferably, the PVC is not cross-linked.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 0.1 to 60 % by weight (based on the total weight of the composition). Preferably, the at least one ester (a) is present in an amount of 10 to 50 % by weight, preferably 20 to 40 % by weight (based on the total weight of the composition).
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one polymer (b) is present in an amount of at least 40 % by weight (based on the total amount of the composition). Preferably, the at least one polymer (b) is present in an amount of at least 50 % by weight, preferably at least 60 % by weight, preferably at least 80 % by weight (based on the total amount of the composition). Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 100 parts or less per 100 parts of resin. Preferably, the at least one ester (a) is present in an amount of 80 parts or less, preferably 60 to 20 parts per 100 parts of resin.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 100 parts or less per 100 parts of the thermoplastic polymer (b). Preferably, the at least one ester (a) is present in an amount of 80 parts or less, preferably 60 to 20 parts per 100 parts of the thermoplastic polymer (b).
In a second aspect the present invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid and at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition as defined herein.
Preferably, the at least one ester is used for plasticizing at least one thermoplastic polymer, preferably polyvinyl chloride (PVC), at least one rubber and any mixture thereof, wherein the at least one rubber is preferably a synthetic rubber, wherein the synthetic rubber is preferably selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof. Most preferred, the at least one ester is used for plasticizing polyvinyl chloride (PVC).
In a third aspect the present invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition as defined herein.
Preferably, any technical feature, either alone or in combination with one or more further technical features, disclosed in context with the composition according to the present invention or according to one or more preferred embodiments is also preferably a technical feature for specifying the uses according to the present invention and/or one or more of their preferred embodiments. Various modifications and variations of the invention will be apparent to those skilled in the art without departing from the scope of the invention. Although the invention has been described in connection with specific preferred embodiments, it should be understood that the invention as claimed should not be unduly limited to such specific embodiments.
The following examples are merely illustrative of the present invention and should not be construed to limit the scope of the invention as indicated by the appended claims in any way.
EXAMPLES
I. Production of esters
The alcohol, the carboxylic acid (each in the amount as listed in table 1, below) and 0.3 g tin- (Il)-oxalate (Goldschmidt) were heated under nitrogen atmosphere. The ester reaction starts at about 170 °C with the production of water. After 3 hours the produced water was removed by applying vacuum and the vacuum was reduced within 4 hours up to about 15 mbar. The final reaction temperature was reached at about 230 °C. After having reached an acid number of less than 1, the excessive alcohol was distilled and the ester was cooled to a temperature of 90 °C, washed with 300 ml water for removing the catalyst, dried and filtered with 2 g bleaching earth (Tonsil, Sudchemie) being added.
Table 1
Figure imgf000015_0001
The produced esters have the following properties/characteristics as shown in table 2, below.
Table 2
Figure imgf000016_0001
The acid numbers were determined pursuant to DIN EN ISO 2114.
II. Production of PVC compositions
The components as listed in table 3, below, were mixed in the amount (each in parts per weight) as listed in table 3, below, and rolled in a rolling mill at a temperature of 185 °C for 5 minutes. Pressed plates with a thickness of 3mm were produced from the rolled sheets at a temperature of 150 °C in a hydraulic press (50 bar for 9 min; 300 bar for 1 min).
Table 3
Figure imgf000016_0002
Emery)
di-2-octyl 40 - - - succinate
(Example 4)
di-2-octyl - 40 - - sebacate
(Example 5)
di-2-octyl azelate - - 40 -
(Example 6)
di-2- - - - 40
ethylhexyladipate
(abbreviated as
DOA; Plastomoll
DOA, BASF)
The transmission, the Shore hardness D and other properties of the pressed plates were measured (see table 4, below).
Table 4
Figure imgf000017_0001
Table 4 shows that by using the plasticizers of Examples 4 to 6, namely di-2-octyl succinate, di-2-octyl sebacate and di-2-octyl azelate, the same properties of PVC were obtained as by di-2-ethylhexyladipate (DOA), used an industrial standard.
III. Stability to hydrolysis of esters
In order to determining the stability to hydrolysis, 150 g ester and 15 g water were stored in closed containers at 90 °C. During the storage the esters hydrolyzed and free acid molecules were obtained. Accordingly, the acid numbers of each ester were tracked over days (see tables 5 and 6). As shown in tables 5 and 6 the 2-octyl esters have a higher stability to hydrolysis than the corresponding 1-octyl or 2-ethylhexyl ester.
i6 Table 5
Figure imgf000018_0001
Table 6
Figure imgf000018_0002
n.d. = not determined
The acid numbers were determined pursuant to DIN EN ISO 2114.

Claims

1. Composition comprising:
(a) at least one carboxylic acid ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and
(b) at least one thermoplastic polymer.
2. Composition according to claim 1 , wherein the at least one alcohol and optionally the at least one carboxylic acid have been obtained from a renewable source.
3. Composition according to claims 1 or 2, wherein the at least one ester has a high stability to hydrolysis.
4. Composition according to any one of the preceding claims, wherein at least 50 mol-% of the at least one alcohol is 2-octanol (based on the total amount of alcohols reacted with the at least one carboxylic acid).
5. Composition according to any one of the preceding claims, wherein the at least one thermoplastic polymer is selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof.
6. Composition according claim 5, wherein the at least one rubber is a synthetic rubber.
7. Composition according to claim 6, wherein the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
8. Composition according to any one of the preceding claims, wherein the content of polymers of methacrylate and/or acrylate is less than 50 % by weight.
i8
9. Composition according to any one of the preceding claims, wherein the at least one carboxylic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids and any mixture thereof.
10. Composition according to any one of the preceding claims, wherein the
monocarboxylic acids are selected from the group consisting of fatty acids, preferably stearic acid, palmitic acid, oleic acid, lauric acid, myristic acid and any mixture thereof.
11. Composition according to any one of the preceding claims, wherein the dicarboxylic acids are selected from the group consisting of succinic acid, azelaic acid, sebacic acid, glutaric acid, suberic acid, adipic acid and any mixture thereof.
12. Composition according to any one of the preceding claims, wherein the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di-2-octyl suberate, di-2-octyl adipate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof.
13. Composition according to any one of the preceding claims, wherein the at least one ester (a) is present in an amount of 0.1 to 60 % by weight (based on the total weight of the composition).
14. Composition according to any one of the preceding claims, wherein the at least one polymer (b) is present in an amount of at least 40 % by weight (based on the total amount of the composition).
15. Composition according to any one of the preceding claims, wherein the at least one ester (a) is present in an amount of 100 part or less per 100 part of resin.
16. Use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition according to any one of claims 1 to 15. Use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition according to any one of claims 1 to 15.
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