EP2688951A1 - Use of epoxidized arylalkylphenols as reactive resin diluents - Google Patents

Use of epoxidized arylalkylphenols as reactive resin diluents

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Publication number
EP2688951A1
EP2688951A1 EP12708815.1A EP12708815A EP2688951A1 EP 2688951 A1 EP2688951 A1 EP 2688951A1 EP 12708815 A EP12708815 A EP 12708815A EP 2688951 A1 EP2688951 A1 EP 2688951A1
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EP
European Patent Office
Prior art keywords
compounds
formula
mixture
characterized
compound
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Withdrawn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
EP12708815.1A
Other languages
German (de)
French (fr)
Inventor
Bodo Friedrich
Knut Hillner
Rolf Herzog
Peter MÜHLENBROCK
Manuela Grewing
Dirk Sichelschmidt
Martina Terhardt
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.)
RUETGERS GERMANY GMBH
Hexion GmbH
Original Assignee
RUETGERS GERMANY GmbH
Hexion GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DE201110015193 priority Critical patent/DE102011015193A1/en
Application filed by RUETGERS GERMANY GmbH, Hexion GmbH filed Critical RUETGERS GERMANY GmbH
Priority to PCT/EP2012/053890 priority patent/WO2012130570A1/en
Publication of EP2688951A1 publication Critical patent/EP2688951A1/en
Application status is Withdrawn legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62Alcohols or phenols
    • C08G59/621Phenols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring heteroatom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/04Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22Di-epoxy compounds
    • C08G59/223Di-epoxy compounds together with monoepoxy compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/15Heterocyclic compounds having oxygen in the ring
    • C08K5/151Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515Three-membered rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Abstract

Glycidylated mono(alkylaryl)phenols (styrenized phenols) or mixtures thereof are suitable for use as reactive diluents and reaction participants in the production of epoxy resins and have the structure of the general formula (I) shown below, in which R1 and R2 are each independently -H, C1-3-alkyl, C1-3-oxalkyl and glycidyl, but R1 and R2 are not both glycidyl, R3 is an optionally substituted styryl of the formula, R4 is a hydrogen radical or methyl and R5 and R6 are each a hydrogen radical, C1-3-alkyl, C1-2-oxalkyl.

Description

 USE OF EPOXYED ARYL ALKYLPHENOLS

 AS REACTIVE THINNER

FIELD OF THE INVENTION

The invention relates to the use of glycidylated mono (alkylaryl) -henols as reactive diluents for epoxy resin compositions, polymerizable compositions containing them and their use in epoxy resins.

BACKGROUND OF THE INVENTION

Glycidylated (epoxidized) compounds are used in various compositions for a wide variety of applications. Depending on their compositions, they are used for example for composite materials, electrical laminates, adhesives, paints, electro casting resins or in the construction sector.

In order for the desired processing properties to be achieved, the individual components of the compositions must be coordinated. Thus, a composition intended for the abovementioned uses usually contains one or more epoxy resin components (thus based on bisphenol A and F, cycloaliphatic resins, brominated resins, phenol novolak resins), hardeners (such as base amines, Adduct hardener, Mannich base hardener, polyaminoamide and polyaminoimidazole hardeners), accelerators (such as benzyldimethylamine and 2, 4, 6-tri (N, -dimethylaminomethyl) phenol) and fillers.

To improve the mechanical properties and cost ¬ reasons it is often desirable to increase the proportion of inorganic filler materials. However, too high Antr 1 - ~ reactive fillers lead to difficulties in vera: trapped in the preparation of the composition on site until application, for example, as a coating.

It is known to add benzyl alcohol or high-boiling solvents such as styrenated phenol (mono (alkylaryl) phenol) to reduce the mixing viscosity of the composition. Styrenated phenol can be used to improve the flow, to accelerate the curing reaction and to obtain better surface properties, for example in coating systems.

A disadvantage of the use of styrenated phenols is increased VOC

Values and / or reduced mechanical properties of the cured epoxy resin.

It is also known to add mono- or multifunctional reactive diluents as viscosity-reducing component. A reactive diluent serves to adjust the viscosity of the mixture and is chemically bound in the cured composition during the curing process so that, as a rule, the emission of solvents can be reduced.

For the production of epoxy resin, various reactive diluents are known. These include low-viscosity mono-, di- or polyfunctional epoxies or epoxy resins based on monofunctional fatty alcohols, di- or polyalcohols. A disadvantage of the use of monofunctional reactive diluents based on aliphatic compounds such as C 12 -C 14 fatty alcohols is a significant delay of the curing reaction (lower reactivity) compared to the non-reactive diluted system. In addition, aliphatic reactive diluents have a higher vapor pressure compared to the base resins, which can lead to limitations during processing.

It is also known to use epoxy compounds based on phenolic compounds as reactive diluents. Such include phenol, resol, bisphenol-A or p-tert. Butylphenol. These show a significantly higher reactivity than epoxy compounds based on aliphatic alcohols. They also impart high chemical resistance to the cured product but are undesirable because of their toxicological properties.

CH 324 686 describes the reaction of phenol with styrene and the reaction of the resulting product with a glycidyl ether in an alkaline medium to form an infusible product.

SUMMARY OF THE INVENTION

The object of the invention is to provide reactive diluents with high reactivity for epoxy resin compositions which do not have the disadvantages indicated above.

This object is achieved by the use of one or more compound (s) I

 I,

in which R 1 and R 2, independently of one another, denote -H, C 1-3 -alkyl, C 1-3 -alkyl and glycidyl, but R 1 and R 2 are not simultaneously glycidyl,

R 3 is an optionally substituted styryl of the formula

R 4 is a hydrogen radical or methyl,

R 5 and R 6 is a hydrogen radical, C 1 -.3-Alk.yl, Ci- 2 -Oxalkyl as reactive diluents in epoxy resin compositions.

Ci-3-alkyl include methyl, ethyl, propyl and isopropyl. C 1 -3 - oxalkyl include methoxy, ethoxy, propoxy and isopropoxy.

The invention further provides the use of a mixture of epoxidized mono (alkylaryl) phenols, i. styrenated phenols having a glycidyl radical as a reactive diluent for epoxy resin compositions.

This mixture contains several compounds of the following chemical formulas Ia, Ib and Ic:

being the connection

and the compound Ib R 1 , R 3 : H

and

 H

0-C-C-CH 2 the compound Ic R 1 :

and R 4 , R s and R 6 have the meanings given above.

The invention further provides a composition comprising one of the aforementioned compounds or a mixture of these compounds containing at least one crosslinkable polymer.

Surprisingly, a composition of one or more inventive epoxy compounds as Reakti diluent despite a high steric hindrance compared to conventional aromatic diluents such as phenol, cresol or p-tert. Butyl phenol a comparable reactivity. The reactivity of the reactive diluents according to the invention is higher than the aliphatic reactive diluents based on mono- or difunctional alcohols.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The mixture according to the invention which is used as reactive diluent preferably contains essentially the following compounds:

in which

 b) R i, R 3. H

R2: 0-CH 2 - CH 2 CH- and c) Ri: O- CH 2 - CH 2 CH-

 O

 R2: H

CH 3

These compounds may be present in at least 60% by weight, preferably at least 80% by weight, more preferably at least 90% by weight or at least 95% by weight in the mixture to be used according to the invention.

Preferably, a mixture, based on the sum of the masses of the compounds of the formula Ia, Ib and Ic, 30 to 60 wt .-% of Ia, 10 to 25 wt .-% of Ib and 20 to 40 wt .-% of Ic ,

The mixture used according to the invention can be obtained by epoxidation of styrenated phenol. The preparation of styrenated phenol by reacting a phenolic component with an olefin is known and described for example in EP 0 656 384 A2. These are essentially alkylation reactions in which the vinyl group of the styrenes is added ortho or para to the hydroxyl group of the phenol. In this reaction, Friedel-Crafts Catalysts, for example acids and Lewis acids used. The addition of the vinyl compound to phenols can be carried out at a molar ratio of the phenolic hydroxyl group in the phenol to the aromatic compound of 1: 1 to 1: 2.

Suitable aromatic vinyl compounds are, in particular, alpha-methylstyrene, styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, commercial vinyltoluene (mixture of isomers), 3,4-dimethylstyrene, 2-dimethylstyrene, 2,5-dimethylstyrene, 2,6-dimethylstyrene , o-ethylstyrene, m-ethylstyrene, p-ethylstyrene, 3,4-diethylstyrene, 2,4-diethylstyrene, 2,5-diethylstyrene, 2,6-diethylstyrene.

Mixtures of styrenated phenols are offered for example by the RÜTGERS Novares® GmbH under the brand "Novares® ®".

The cationically induced conversion to styrenated phenol results in a statistical distribution of 2-, 4- and 2,4-substituted phenol. To obtain the individual styrenated compounds, the monostyrrated compounds can first be separated from the distyrenated phenol by vacuum distillation. The mixture of monostyrenated compounds can then be separated by crystallization into the 2-styrenated and 4-styrenated phenol.

The styrenated phenol or a mixture of styrenated phenols is reacted with an oxirane compound to obtain the epoxidized compounds of this invention. The phenolic OH group reacts with the oxirane compound. The oxirane compound used is preferably epichlorohydrin. The reaction is generally carried out in the presence of alkali metal hydroxide, for example sodium hydroxide, at elevated temperature according to the theoretical equation with elimination of common salt and water to give the glycidyl compound according to the invention in accordance with the reaction scheme shown below:

This reaction is basically known, wherein R is the common basic building block of the substances Ia, Ib and Ic and the benzene ring has an OH group at the corresponding positions.

Surprisingly, the mixture used according to the invention can be used as a reactive compound, even if a hydrophobicizing effect is to be achieved. This can be done, for example, in coating compositions by using the mixture according to the invention as a resin constituent or as a reactive diluent with at least one further resin constituent. Likewise, the mixture can be used as a modifier in the polyester synthesis, for example for reducing acid groups or alcohol groups, while at the same time increasing the hydrophobicity. Furthermore, the mixture according to the invention can be used as a paper treatment agent without showing the known disadvantages of migration as in non-reactive phenolic components.

Surprisingly, it has also been found that the use of the mixture to be used according to the invention increases the resistance of composite materials, such as are increasingly used in the production of wind energy, to water or aqueous media.

Generally, this blend can be used to make reinforced or unreinforced plastics (e.g., thermosets, thermoplastics) and elastomers.

Particular preference is given to compositions which, as further component, comprise at least one crosslinkable plastic (thermopolast, Elastomer), in particular duroplastic plastic (such as polyester resin, epoxy resin, phenolic resin or melamine resin) have.

It is advantageous if the mixture according to the invention with at least one crosslinkable plastic in a ratio of 5:95 to 50:50 is present. The preparation of the composition takes place in üb Licher way.

It is particularly preferred if the mixture to be used according to the invention as a further component at least d) an epoxy resin selected from glycidyl ether based on bisphenol A, bisphenol F or novolaks, mono-, di- or polyfunctional alcohols, mono- or polyfunctional phenol len such as phenol, cresol, resorcinols, naphthols, p-tert-butylphenols, nonylphenols, cashew nut oil compounds, C 12 C14 alcohols, butanediols and / or hexanediols e) a hardener selected from aminic or acidic compounds and such Hardeners which can initiate a homopolymerization of epoxy compounds and f) optionally further additives, such as processing aids ¬ and inorganic fillers, preferably 5 to 20 parts by weight, based on all components of the composition.

The use of glycidyl ethers based on bisphenol A, bisphenol F or novolaks, mono-, di- or polyfunctional alcohols, mono- or polyfunctional phenols, such as phenol, cresol resorcinols, naphthols, p-tert. Butylphenols, nonylphenols, cashew nut oil compounds, C 2 -C 4 -alcohols, butanediol and / or Hexanediol as further component has the advantage that the composition is crystallization resistant and storable. In addition, the viscosity of this composition according to the invention can be adjusted in an appropriate range for the application.

Usual hardeners for Bpoxide can be used. Typical representatives of the amine hardeners are compounds with one, two or more free amine hydrogens. These may have cyclic, aliphatic or aromatic linkages or polyether groups. Typical representatives of this hardener class are amines such as isophoronediamine, xylylenediamine, trimethylene-hexamethylenediamine, polyetheramines. Also suitable hardeners according to the invention are so-called acidic hardeners based on organic acids such as phthalic anhydride, hexahydrophthalic anhydride, methylhydrophthalic anhydride and other compounds of this class. Also not excluded are latent systems which are applied via radiation curing and associated ionic hardening or by thermal curing ("latent 1-component system"). Preferred in the sense of the invention are amine hardeners for the range of curing

Room temperature, here in particular so-called adduct hardeners based on bisphenol A diglycidyl ether and isophoronediamine, which are further modified by the use of benzyl alcohol, accelerators and other additives to improve the processing properties or end uses. The mixing ratio with the epoxide-reactive components results from the stoichiometric conversion. The exact mixing ratio depends on the application and may include both a substoichiometric and a superstoichiometric implementation.

The epoxy resin composition of the present invention is prepared by mixing the individual components according to known methods. By mixing the components at a higher temperature, for example at 60 ° to 80 ° C, the mixing and filling process can be accelerated. Preferably, the epoxy resin component d) to the sum of components a) to c) in a ratio of 95: 5 to 50:50, more preferably 95: 5 to 85:20, before. In this area, excellent mechanical properties are achieved in the hardened state. Depending on the application, higher or lower proportions can also be used.

The mixture according to the invention can be used for the production of thermosetting products. Thus, coatings or even shaped bodies are conceivable. It is particularly preferred if the mixture according to the invention is used for coatings, in particular for self-leveling coatings. For example, coatings for industrial floors, paints, adhesives or electrical laminates would be conceivable. The use according to the invention thus takes place preferably for the treatment of paper, for the production of cured polymer products, for the production of coatings, for the production of reinforced and unreinforced plastics, elastomers and moldings.

The following examples serve to further illustrate the invention.

EXAMPLES

Example 1 Preparation of the Mixture to be Used According to the Invention

There are presented to 925 g of epichlorohydrin (10 mol) in a 2 1 laboratory reactor with drain cock. The temperature is raised to 65 ° C. Subsequently, 466 g (2 mol OH) Novares LS 500 ® (RÜTGERS Novares GmbH) (styrenated phenol) as well as 29.3 g (0.1 mol) of sodium hydroxide solution (20% strength) are added. After the dissolution process is heated to 100 ° C. The reaction mixture is stirred for 3 hours and then cooled to 45.degree. Now 50 g of isopropanol and 140 g of water are added to the reaction mixture. Within 120 min, 400 g of 20% sodium hydroxide solution {stoichiometric amount) are added. The temperature is maintained at a constant 45 ° C for two hours (2 h after-reaction).

36 g of NaCl are added and the mixture is allowed to react for a further 60 minutes. It is then heated to 60.degree.

The stirrer is switched off and after a Absitzezeit of 30 minutes, the lower aqueous phase is drained. The remaining organic phase in the reaction vessel is diluted with a further 200 g of epichlorohydrin and washed with 300 g of water, with a phase inversion takes place.

The organic phase is then distilled off under reduced pressure up to a temperature of 120 ° C and freed from traces of volatiles by steam distillation in vacuo.

The distillate contains epichlorohydrin, isopropanol, water and higher boiling impurities at a concentration of less than 1% and can be used for subsequent production. The distillation residue is taken up in 248 g of toluene, heated to 75 ° C and treated with 50% sodium hydroxide solution (MV 1: 2.5 - hydrolyzable chlorine: sodium hydroxide solution) within 30 minutes. Beforehand, the same amount of water is added. The reaction time with stirring is then 1 hour. 330 g of toluene are added for dilution. The stirrer is switched off and after a settling time of 10 minutes, the aqueous phase is separated off. The organic solution is washed several times with water until neutral. The toluene and remaining traces of volatiles are distilled off in vacuo to 125 ° C. The epoxide compound obtained as the distillation residue is purified by a pressure filter of organic and inorganic solid impurities. The yield, based on the precursor, is 95%.

Analysis results of the epoxy compound:

 Epoxide equivalent 384 g / eq

 Viscosity 25 ° C 545 mPas

 Hydrolyzed chlorine content 0.36%

 Color after Gardner

Example 2 - Application of the mixture

The glycidated "styrenated phenol" (B) produced in Example 1 is used for the preparation of epoxy resin mixtures. For this purpose, the bisphenol A diglycidyl ether is introduced into the mixing unit and the styrenated product (A) or the product (B) according to the invention is added with stirring. The temperature during the stirring is kept between 65 ° C and 70 ° C. This composition is optionally added after storage of the hardener in the indicated concentration (Table 1). On a floor coating (primer or self-leveling floor coating), the properties of compositions containing the product (A) (styrenated phenol) are compared with compositions containing the product (B) of the invention. Formulation ingredients I II

 (Invention)

Resin:

Bisphenol-A diglycidyl ether 80 80 EPIKOTE ® Resin 828LVEL

 Styrenated Phenol (A): 20 -

Styrenated phenol, glycidated 20 (B):

 Epoxide equivalent 232 202

 Harder:

EPIKURE ® Curing Agent 551

(Adduct hardener of bisphenol A diglycidyl ether and isophoronediamine,

modified u.a. with benzyl alcohol)

 Amine equivalent 93 93

Resin: Hardener [parts by weight] 100: 40 100: 46

Properties :

 Relative waste f loss 0 -31%

[Curing 96h at 23 ° C, determination

of evaporation loss by weight measurement lh after application and after storage [2h, 100 ° C, layer thickness 200

μπι]]

To determine the evaporation loss, the coating composition is applied with a doctor blade to a glass plate in a layer thickness of 200 μm. After one hour, the glass plate is weighed. The glass plate is then stored for 96 hours at room temperature and then for two hours at 100 ° C in a drying oven. Then the weight is determined and the difference the two weight measurements determined the relative weight loss.

It has been demonstrated that the proportion of volatile compounds during curing is drastically reduced according to the invention, since the mixture II according to the invention is incorporated into the organic matrix, which is shown by the determination of the evaporation loss.

Furthermore, an improvement in the property profile in self-leveling coatings was observed (Table 2). The compositions were prepared as previously described

Table 2:

 Recipe components Reference: I II III

 invention

 Resin:

 Bisphenol A 100 90 90 90 diglycidyl ether

EPIKOTE ® Resin 828LVEL

 Ci2-ci4 glycidyl ether: 10

Styrenated phenol, 10

glycidated (B):

 Hexanediol diglycidyl ether 10

Epoxide equivalent 186 193 194 180 [g / Aquiv. ]

 Viscosity [25 ° C, Pas] 10.6 1.6 6.6 2.3

Harder :

 Addukthärter based

of bisphenol A diglycidyl ether and

Isophoronediamine modifi- decorated with benzyl alcohol

and accelerator

EPICURE ® Curing Agent

F205

 Amine equivalent 105 105 105 105

Resin. "Hardener [Mass: 100: 56 100: 54 100: 54 100: 58 le]

Properties :

 Pot life [100 g, t to 39 44 43 37 Tmax, min], DIN 16945

 Gel time [23 ° C, min], DIN 103 166 133 156 16945

Early water resistance - / - / o / o _ / _ / _ / 0 0/0 / + / + - / 0/0 / + 10 ° C [4/8/24/48 hours], ISO 2812-4

 Early water resistance - / o / o / o - / 0/0 / + 0 / + / +++ / + 0 / + / + / + 23 ° C [4/8/24/48 hours], ISO 2812-4

 Surface 10 ° C [48 h] Matt Matt Light Matt Visually DIN 53230 Matt

 Surface 23 ° C [48 h] Good Good Glossy Good visually DIN 53230

By using the mixture II according to the invention (styrenated phenol, glycidated (B)), a significant acceleration of the curing reaction is found in direct comparison to the aliphatic reactive diluents (III). At the same time the

Early water resistance (resistance against undesired Ne ¬ benreaktionen by water during the curing, for example Carbamatbil- formation) - measured in comparison to the reference significantly improved. Table 3 shows the improvement in mechanical properties. Table 3:

 Recipe ingredients I II

 (Invention)

resin

Bisphenol A diglycidyl ether 85 85 EPIKOTE ® Resin 828LVEL

 Neodecanoic acid glycidyl ether 15 -

Styrenated phenol, glycated (B). - 15

 Resin:

 Epoxide equivalent 193 198

Viscosity [25 ° C, Pas] 1.5 5.6

Harder :

 Adduct hardener based on bisphenol 54 53 A diglycidyl ether and isophoronediamine

modified with benzyl alcohol and accelerator

EPIKURE ® Curing Agent F205

(Amine equivalent 105 g / equiv.)

Table 4

 Initial values: I II

 (Invention)

Mechanical properties

[Hardening 7 days 23 ° C]

 Shore D hardness, DIN EN ISO 868 79 83

Bending strength [MPa], DIN EN ISO 178 69 93

Modulus of elasticity [MPa], DIN EN ISO 178 1900 2700

Tensile strength [MPa], DIN EN ISO 527 45 62

Elongation [MPa], DIN EN ISO 527 3.1 2.7

Compressive strength [MPa], DIN EN ISO 604 67 87

Tg [° C, DSC], IEC 1006 42 46

Tg [° C, DMA], IEC 1006 58 60 DSC: Dynamic Differential Scalometry

 DMA: Dynamic Mechanical Analysis Although both are monofunctional reactive diluents, higher mechanical values are achieved using (B).

The chemical resistance test first shows that the measured Shore D values (hardness) are comparable using the monofunctional reactive diluents. However, using (B) it takes twice as long to cause mechanical damage (4 instead of 2 weeks) (Table 5).

Table 5:

 In brackets:% of initial value (7d 23 ° C)

Claims

 Patent claims
Use of a formula
I in which R 1 and R 2, independently of one another, denote -H, C 1-2-alkyl, ci-oxyalkyl and glycidyl, but R 1 and R 2 are not simultaneously glycidyl,
R 3 is an optionally substituted styryl of the formula
 R is a hydrogen radical or methyl,
R 5 and R 6 are each a hydrogen radical, C 1-3 -alkyl, C 1-3 -alkyl,
Oxalkyl is or one
A mixture of glycidylated mono (alkylaryl) -heols containing compounds of the general formula I as reactive diluents for epoxy resin compositions.
2. Use according to claim 1, characterized by the general formula Ia wherein R R 2 and R 3 are a hydrogen radical and R 4 , R 5 and R 6 have the meaning given above.
3. Use according to claim 1, characterized by the general formula Ib
H
0-C-C-CH 2 , R 1 and R 3 are a hydrogen radical and R 4 , R 5 and R 6 have the meaning given above.
4. Use according to claim 1, characterized by the general formula Ic wherein R1
R 2 is a hydrogen radical and R 3 is a radical of the formula
and wherein R 4 , R 5 and R 6 have the meaning given above.
5. Use according to claim 1, characterized in that in
Mixture of the compounds of formula I, the compounds of formulas Ia, Ib and Ic are included.
6. Use according to claim 5, characterized in that the mixture 30 to 60 wt .-% of the compound of formula Ia, 10 to 25 wt .-% of the compound of formula Ib and 20 to 40 wt .-% of the compound of formula Ic contains.
7. Use according to one of claims 1 to 6 for the treatment of paper, for the production of cured polymer products, for the production of coatings, for the production of reinforced and unreinforced plastics, elastomers and moldings. Composition, characterized in that it contains a compound of formula I or a mixture of compounds of formula I and at least one crosslinkable polymer.
Composition according to Claim 8, characterized in that the mass ratio of a compound of Claims 1 to 4 or a mixture of Claims 5 to 7 and a crosslinkable polymer is 95: 5 to 50:50, in particular 95: 5 to 85:15.
A composition according to claim 9 or 10, characterized in that as the crosslinkable polymer at least d) an epoxy resin selected from alcoholic compounds capable of forming glycidic compounds, in particular glycidyl ethers based on bisphenol A, bisphenol F or novolaks, mono-, di-, or polyfunkti ¬ tional alcohols, mono- or polyfunctional phenols, such as phenol, cresol, resorcinols, naphthols, p-tert-butyl phenols, nonyl phenols, cashew-oil compounds, C 2 -C 4 alcohols , Butanediols, hexanediols and e) a hardener selected from aminic or acidic compounds and those hardeners which can initiate homopolymerization of epoxide compounds and f) optionally further additives.
EP12708815.1A 2011-03-25 2012-03-07 Use of epoxidized arylalkylphenols as reactive resin diluents Withdrawn EP2688951A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE201110015193 DE102011015193A1 (en) 2011-03-25 2011-03-25 Epoxidized arylalkylphenols
PCT/EP2012/053890 WO2012130570A1 (en) 2011-03-25 2012-03-07 Use of epoxidized arylalkylphenols as reactive resin diluents

Publications (1)

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EP (1) EP2688951A1 (en)
JP (1) JP2014515045A (en)
KR (1) KR20140041470A (en)
CN (1) CN103459482A (en)
DE (1) DE102011015193A1 (en)
WO (1) WO2012130570A1 (en)

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KR20140041470A (en) 2014-04-04
DE102011015193A1 (en) 2012-09-27

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