KR101877491B1 - AN α-METHYL STYRENATED PHENOL MIXTURE, A NON-REACTIVE DILUENT COMPRINSING THE SAME, AND A METHOD FOR MANUFACTURING THE SAME - Google Patents

Abstract

An aspect of the present invention provides a method for manufacturing an α-methyl styrenated phenol mixture which comprises the steps of: (a) manufacturing an intermediate by reacting one equivalent of phenol and 0.1-3.0 equivalent of α-methylstyrene (AMS) in the presence of 0.0001-0.005 acid catalyst; and (b) obtaining a mixture including a first product containing a hydroxyl and a second product not containing the hydroxyl by neutralizing and filtering the intermediate.

Description

METHOD FOR MANUFACTURING THE SAME, AND NON-REACTIVE DILUENT COMPRISING THE SAME, AND AN A METHOD FOR MANUFACTURING THE SAME,

The present invention relates to an alpha methyl styrene-naphthol phenol mixture, a non-reactive diluent comprising the same, and a process for preparing the same.

A variety of non-reactive diluents have conventionally been used to impart plasticity to compositions of conventional epoxy coatings and for use in diluent applications. Representative non-reactive diluents include alkylphenol compounds such as nonylphenol, dodecylphenol, and octylphenol; benzyl alcohol; C5 to C9 hydrocarbon resins; and mixtures of phenol and alpha methylstyrene oligomers.

Among them, alkylphenol compounds have been widely used as additives for epoxy coatings or surfactants which require plasticity in terms of molecular structure and chemical properties. However, these alkylphenol compounds are known as renal toxins and endocrine disrupters, and they are currently prohibited from being used worldwide or their use is gradually limited.

In addition, since benzyl alcohol has low boiling point, environmental hazard due to volatile organic compounds (VOC) is problematic. In the case of alpha methylstyrene oligomer, a large amount of unreacted petroleum VOC such as benzene, xylene, etc. remains and oligomer structure There is a problem that it is complicated and the composition is not uniform.

In order to solve this problem, a mixture of alpha methyl styrene-phenol, which is produced by reacting phenol with alpha methyl styrene in the presence of an acid catalyst, is used as a diluent for an epoxy paint. However, There is a limitation that the acid catalyst which can be used is limited and some of the components included in such a mixture optionally react with the amine curing agent and the like contained in the paint to cause unnecessary discoloration in the paint composition.

In addition, since phenol and alpha methyl styrene are used in high boiling point solvent such as benzene and xylene, it is necessary not only to remove the solvent in the purification process but also to cause the solvent to remain in the final product, .

Accordingly, there is a need to develop an alpha-methyl styrene-phenol mixture which is useful as a non-reactive diluent for an epoxy paint and a method for producing the same, by solving the problem of VOC generation caused by the use of a solvent and uniformly maintaining the composition of the product.

SUMMARY OF THE INVENTION The present invention has been made in order to solve the problems of the prior art described above, and it is an object of the present invention to provide a process for producing an alpha methyl styrene- , And to provide a non-reactive diluent capable of originally blocking a chemical mechanism causing discoloration of an epoxy paint composition.

One aspect of the present invention relates to an alpha methyl styrene-naphthol phenol mixture comprising a first component containing a hydroxyl group and a second component containing no hydroxyl group, wherein the first component containing a hydroxyl group is selected from the group consisting of p-cumylphenol and Dicumylphenol, wherein the content of the p-cumylphenol and the dicumylphenol is 20 to 60% by weight based on the total weight of the alpha-methyl styrene-naphthol phenol mixture, to provide.

In one embodiment, the content of the first component may be greater than or equal to 65% by weight, based on the total weight of the alpha methyl styrene naphthophenol mixture.

In one embodiment, the second component may comprise an alpha methyl styrene dimer (AMS dimer) and an alpha methyl trimer (AMS trimer).

In one embodiment, the content of the second component may be 25% by weight or less based on the total weight of the alpha methyl styrene naphthophenol mixture.

In one embodiment, the alpha methyl styrene naphthophenol mixture may further comprise one third component selected from the group consisting of phenol, alpha methyl styrene, and mixtures thereof.

In one embodiment, the content of the third component may be less than or equal to 1% by weight based on the total weight of the alpha methyl styrene naphthophenol mixture.

Another aspect of the present invention provides a non-reactive diluent for an epoxy paint comprising the alpha methyl styrene naphthophenol mixture.

Another aspect of the present invention is a process for preparing an intermediate product comprising the steps of: (a) reacting 1 equivalent of phenol and 0.1 to 3.0 equivalents of alpha methyl styrene (AMS) in the presence of 0.0001 to 0.005 equivalents of an acid catalyst; And (b) neutralizing and filtering the intermediate to obtain a mixture comprising a first product containing a hydroxyl group, a second product containing no hydroxyl groups, and an unreacted material, Phenol < / RTI >

In one embodiment, the acid catalyst is selected from the group consisting of sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, phosphoric acid, polyphosphoric acid, nitric acid, hydrochloric acid, boron trifluoride complexes, acid clay, ion exchange resins and mixtures of two or more thereof Lt; / RTI >

In one embodiment, the first product may comprise p-cumylphenol and dicumylphenol.

In one embodiment, the content of the p-cumylphenol and the dicumylphenol may be 20 to 60 wt%, respectively, based on the total weight of the mixture.

In one embodiment, the second product may comprise an alpha methyl styrene dimer and an alpha methyl trimer.

In one embodiment, the content of the second product may be 25% by weight or less based on the total weight of the mixture.

In one embodiment, the content of the unreacted material may be up to 1% by weight based on the total weight of the mixture.

According to one aspect of the present invention, by adjusting the composition ratio of some components among a plurality of components present in the alpha-methyl styrene-naphthyl phenol mixture to a predetermined range, it is possible to improve the reaction with an amine-based curing agent when applied as a non-reactive diluent in an epoxy paint It is possible to prevent the discoloration which may be caused by the above-mentioned defects, and to improve the stability of the epoxy paint.

According to another aspect of the present invention, the amount of the reactants and the catalyst used is adjusted to a predetermined range in the production of the alpha methyl styrene-substituted phenol, thereby maintaining the composition of the product constantly, thereby improving the reproducibility and reliability. In addition, since no additional solvent is used in the production of alpha methyl styrene-naphthyl phenol, it is advantageous in environmental and economic aspects.

It should be understood that the effects of the present invention are not limited to the effects described above, but include all effects that can be deduced from the description of the invention or the composition of the invention set forth in the claims.

The present invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Throughout the specification, when a part is referred to as being "connected" to another part, it includes not only "directly connected" but also "indirectly connected" . Also, when an element is referred to as "comprising ", it means that it can include other elements, not excluding other elements unless specifically stated otherwise.

One aspect of the present invention relates to an alpha methyl styrene-naphthol phenol mixture comprising a first component containing a hydroxyl group (-OH) and a second component containing no hydroxyl group (-OH) Wherein the one component comprises p-cumylphenol and dicumylphenol, and the content of the p-cumylphenol and the dicumylphenol is 20 to 60% by weight based on the total weight of the alpha-methylstyrene-phenol mixture, Alpha methyl styrene naphthophenol mixture.

Generally, the alpha methyl styrene naphthophenol mixture is produced by an alkylation reaction of phenol and alpha methyl styrene, and this alkylation reaction can be represented by the following reaction formula (1).

<Reaction Scheme 1>

Referring to Reaction Scheme 1, the alpha methyl styrene-naphthol phenol mixture is a mixture of cumene phenol with one molecule of phenol and one molecule of alpha methyl styrene, dicumylphenol with one molecule of phenol and two molecules of alphamethylstyrene , AMS dimer in which two molecules of alpha methyl styrene are bonded, AMS trimer in which three molecules of alpha methyl styrene are bonded, and other unreacted substances Lt; / RTI &gt; That is, not only phenol and alpha methylstyrene can be reacted to produce various types of styrene-substituted phenols, but also alpha-methylstyrene may react with each other to produce dimers, trimers, and the like.

The cumyl phenol may be present as a mixture of o-cumyl phenol, m-cumyl phenol, and p-cumyl phenol with alpha methyl styrene bonded at the ortho, meta, and para positions of the phenol , P-cumylphenol can predominantly be generated by the steric factor of alpha methylstyrene and phenol due to the hydroxyl group of the above-mentioned phenol which is the electron-hole excitation (EDG).

The alpha methylstyrene dimer can be produced by reacting the alphamethylstyrene with two molecules and depending on the bonding position, trimethylphenylindane (TMPI) and diphenylmethylpentene (DMP) Wherein the trimethylphenylindane is 1,1,3-trimethyl-3-phenyl, the diphenylmethylpentene is 4-methyl-2,4-diphenyl-1-pentene and 4-methyl- Diphenyl-2-pentene.

The alpha methyl styrene reacts with cumyl phenol in the product to form dicumyl phenol. Specifically, the alpha-methylstyrene may react with p-cumylphenol to produce 2,4-dicumylphenol and react with o-cumylphenol to produce 2,6-dicumylphenol.

In addition, alpha methylstyrene can be reacted with diphenylmethylpentene (DMP) in the product to produce alpha methyl trimer. Specifically, the alpha methylstyrene may react with 4-methyl-2,4-diphenyl-1-pentene to produce 2,4,6-triphenyl-4,6-dimethylhept- 4-methyl-2,4-diphenyl-2-pentene to give 2,4,6-triphenyl-4,6-dimethylhept-2-ene.

As described above, the alpha methyl styrene naphthophenol mixture may include a first component containing a hydroxyl group and a second component not containing a hydroxyl group.

Wherein the first component containing hydroxyl groups may comprise p-cumylphenol and dicumylphenol and wherein the content of p-cumylphenol and the amount of dicumylphenol is in the range of And the content of the first component including the p-cumylphenol and the dicumylphenol may be 65% by weight or more based on the total weight of the alpha methyl styrene-naphthol phenol mixture .

On the other hand, the second component not containing a hydroxyl group may include an alpha methyl styrene dimer (AMS dimer) and an alpha methyl trimer (AMS trimer), and the content of the second component may be less than the alpha methyl styrene 0.0 &gt; 25% &lt; / RTI &gt; by weight based on the total weight of the phenol mixture.

When the content of the first and second components is out of the above range, when the alpha methyl styrene-naphthophenol mixture and the amine-based component are mixed, the alpha methyl styrene-naphthophenol mixture and the amine- Lt; / RTI &gt;

Alkylphenol-based compounds, nonylphenol, C5-C9 hydrocarbon resins and the like, which are conventionally used as an additive in epoxy coating compositions, for example, as a diluent, can be prepared by reacting an amine component contained as a curing agent in an epoxy coating composition, The hydrogen atoms in the hydroxyl groups of the phenol are reacted to give radicals to the alkyl groups bonded at the para positions of the phenol and the radicals are mutually reacted to transform the molecular structure into the stilbenquinone type resonance structure, The transparent epoxy coating composition may be discolored to brown, red, pink, yellow, and the like.

On the other hand, the first component contained in the alpha methyl styrene-naphthyl phenol mixture according to the present invention is one in which the para position of phenol is substituted with alpha methyl styrene, which is an aromatic hydrocarbon compound structurally stable as compared with the conventional alkyl group, An arbitrary reaction with the amine-based component in the epoxy coating composition and consequent discoloration can be fundamentally blocked. The content of the first component is more than 50% by weight, preferably not less than 60% by weight, more preferably not less than 70% by weight, of the alphamethylstyrene-phenol mixture, %, It is possible to maximize the effect of preventing discoloration.

On the other hand, the alpha methyl styrene naphthophenol mixture may include one third component selected from the group consisting of phenol, alphamethylstyrene, and mixtures thereof, which are unreacted matters remaining after the reaction. The content of the third component may be up to 1% by weight based on the total weight of the alpha methyl styrene-naphthol phenol mixture.

Another aspect of the present invention provides a non-reactive diluent for an epoxy paint comprising the alpha methyl styrene naphthophenol mixture. In the alpha methyl styrene-substituted phenol mixture, the first component is a non-reactive component that does not optionally react with the amine-based component, and the first component is excessive relative to the second component, Can be applied as a substantially non-reactive diluent in an epoxy coating composition. For example, the alphamethylstyrene-phenol mixture may be mixed with the main and / or curing agent portions of the epoxy paint at a ratio of 1 to 50% by weight and applied as a non-reactive diluent.

Another aspect of the present invention is a process for preparing an intermediate product comprising the steps of: (a) reacting 1 equivalent of phenol and 0.1 to 3.0 equivalents of alpha methyl styrene (AMS) in the presence of 0.0001 to 0.005 equivalents of an acid catalyst; And (b) neutralizing and filtering the intermediate to obtain a mixture comprising a first product containing a hydroxyl group, a second product containing no hydroxyl groups, and an unreacted material, Phenol &lt; / RTI &gt;

In the step (a), an intermediate may be prepared by reacting 1 equivalent of phenol and 0.1-3.0 equivalents of alpha methyl styrene (AMS) in the presence of 0.0001-0.005 equivalents of an acid catalyst.

The phenol may be used alone or in admixture with derivatives thereof to obtain a greater variety of alphamethylstyrene-based phenol compounds. Wherein the phenol derivative is at least one selected from the group consisting of o-cresol, m-cresol, p-cresol, 2,5-xylenol, 3,5-xylenol, 3,4- Ethylphenol, m-ethylphenol, p-ethylphenol, p-tert-butylphenol, p-octylphenol, m-methoxyphenol, p-methoxyphenol, 3,4-dimethoxyphenol, Propoxyphenol, m-butoxyphenol, p-butoxyphenol, 2-methyl-4-isopropylphenol, p-methoxyphenol, But is not limited to, one or more selected from the group consisting of phenol, o-chlorophenol, m-chlorophenol, p-chlorophenol, dihydroxybiphenyl, bisphenol A, phenylphenol, resorcinol, and naphthol no.

The compositional ratio of the alpha methyl styrene-phenol mixture prepared by neutralization and filtration of the intermediate product may vary depending on the equivalence ratio of the reactant phenol and alpha methyl styrene, the kind and content of the catalyst, the reaction temperature, and the reaction time. As used herein, the term "equivalent" refers to the relative proportion of the weight of reactants or catalysts used in the preparation of the alpha methyl styrene-naphthol phenol mixture, such as phenol, alpha methyl styrene, do.

The step (a) may be performed at a temperature of 50 to 200 ° C, preferably 70 to 150 ° C, since the temperature increases during the reaction corresponding to the exothermic reaction. If the temperature is lower than 50 캜, the catalytic activity may be lowered and the reaction rate may be lowered. If the temperature is higher than 200 캜, discoloration may occur in the product during the reaction.

In the step (a), the equivalence ratios of the phenol and the acid catalyst may be 1: 0.0001 to 0.005, preferably 0.0001 to 0.002. If the amount of the acid catalyst is less than 0.0001 equivalent based on 1 equivalent of the phenol, the reaction rate may decrease. If the amount of the acid catalyst exceeds 0.005 equivalent, the composition ratio of the alpha methyl styrene nitrile phenol mixture prepared by neutralizing and filtering the intermediate, Range.

In the step (a), the equivalent ratio of the phenol and the alphamethylstyrene may be 1: 0.1 to 3.0, preferably 1: 0.1 to 2.5. If the equivalent amount of the alpha methylstyrene per one equivalent of the phenol is less than 0.1, the unreacted phenol may remain in excess and the economical efficiency may be lowered. On the other hand, if the equivalent amount exceeds 3.0, the alpha methylstyrene dimer and alpha methylstyrene trimer And viscosity increase and crystallization can be induced.

Wherein the acid catalyst is one selected from the group consisting of sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, phosphoric acid, polyphosphoric acid, nitric acid, hydrochloric acid, boron trifluoride complex compound, acidic clay, ion exchange resin, Preferably sulfuric acid or p-toluenesulfonic acid, but is not limited thereto.

After completing the reaction of step (a), the neutralization reaction is performed by adding a basic aqueous solution to the intermediate in step (b), and then the resulting solution is concentrated under reduced pressure to remove moisture, By removing the neutralized salt, a purified alpha methyl styrene naphthophenol mixture can be obtained.

The basic aqueous solution may be at least one selected from the group consisting of an aqueous solution of sodium carbonate, an aqueous solution of potassium carbonate, an aqueous solution of sodium hydrogencarbonate, an aqueous solution of sodium hydroxide and an aqueous solution of potassium hydroxide, but is not limited thereto. If there is, suffice it. The basic aqueous solution may be used in a proportion of 0.1 to 3.0 equivalents based on 1 equivalent of the phenol, but is not limited thereto.

Wherein the first and second products correspond to the first and second components of the alpha methyl styrene-naphthophenol mixture, respectively, with respect to the composition of the first and second products, Lt; / RTI &gt; Further, the unreacted product corresponds to the third component of the alpha methyl styrene-naphthophenol mixture, and the composition of the unreacted product is the same as that described above for the third component.

Hereinafter, embodiments of the present invention will be described in detail.

Example  One

Sulfuric acid catalyst (0.313 g, 0.001 eq) was added to phenol (PhOH, 300 g, 1 eq) and alpha methyl styrene (AMS, 452.08 g, 1.2 eq) was added dropwise while heating from 80 ° C to 90 ° C for 300 minutes. After the dropping of the alpha methylstyrene was completed, the reaction was further continued at the same temperature for 60 minutes.

Subsequently, sodium bicarbonate (0.268 g, 0.001 eq) was dissolved in distilled water, and the mixture was added at 90 to 100 ° C for neutralization for 60 minutes. The resulting solution was concentrated under reduced pressure at 120 DEG C for 120 minutes to remove water, and then the neutralized salt was removed using a filter to obtain a purified alpha methyl styrene-phenol mixture.

Example  2

Toluenesulfonic acid (0.606 g, 0.001 eq) was added to phenol (PhOH, 300 g, 1 eq), and alpha methylstyrene (AMS, 452.08 g, 1.2 eq) Respectively. After the dropping of the alpha methylstyrene was completed, the reaction was further continued at the same temperature for 60 minutes.

Subsequently, sodium bicarbonate (0.268 g, 0.001 eq) was dissolved in distilled water, and the mixture was added at 90 to 100 ° C for neutralization for 60 minutes. The resulting solution was concentrated under reduced pressure at 120 DEG C for 120 minutes to remove water, and then the neutralized salt was removed using a filter to obtain a purified alpha methyl styrene-phenol mixture.

Example  3

Sulfuric acid catalyst (0.313 g, 0.001 eq) was added to phenol (PhOH, 300 g, 1 eq) and alpha methylstyrene (AMS, 565.09 g, 1.5 eq) was added dropwise while heating from 80 ° C to 90 ° C for 300 minutes. After the dropping of the alpha methylstyrene was completed, the reaction was further continued at the same temperature for 60 minutes.

Subsequently, sodium bicarbonate (0.268 g, 0.001 eq) was dissolved in distilled water, and the mixture was added at 90 to 100 ° C for neutralization for 60 minutes. The resulting solution was concentrated under reduced pressure at 130 캜 for 90 minutes to remove water, and then the neutralized salt was removed by using a filter filter to obtain a purified alpha methyl styrene-phenol mixture.

Example  4

Sulfuric acid catalyst (0.313 g, 0.001 eq) was added to phenol (PhOH, 300 g, 1 eq) and alpha methylstyrene (AMS, 753.46 g, 2.0 eq) was added dropwise while heating from 80 占 폚 to 90 占 폚 for 300 minutes. After the dropping of the alpha methylstyrene was completed, the reaction was further continued at the same temperature for 60 minutes.

Subsequently, sodium bicarbonate (0.268 g, 0.001 eq) was dissolved in distilled water, and the mixture was added at 90 to 100 ° C for neutralization for 60 minutes. The resulting solution was concentrated under reduced pressure at 130 캜 for 90 minutes to remove water, and then the neutralized salt was removed by using a filter filter to obtain a purified alpha methyl styrene-phenol mixture.

Example  5

Sulfuric acid catalyst (0.313 g, 0.001 eq) was added to phenol (PhOH, 300 g, 1 eq) and alpha methylstyrene (AMS, 828.80 g, 2.2 eq) was added dropwise while heating from 80 占 폚 to 90 占 폚 for 300 minutes. After the dropping of the alpha methylstyrene was completed, the reaction was further continued at the same temperature for 60 minutes.

Subsequently, sodium bicarbonate (0.268 g, 0.001 eq) was dissolved in distilled water, and the mixture was added at 90 to 100 ° C for neutralization for 60 minutes. The resulting solution was concentrated under reduced pressure at 130 캜 for 90 minutes to remove water, and then the neutralized salt was removed by using a filter filter to obtain a purified alpha methyl styrene-phenol mixture.

Example  6

Sulfuric acid catalyst (0.563 g, 0.0018 eq) was added to phenol (PhOH, 300 g, 1 eq) and alpha methylstyrene (AMS, 828.80 g, 2.2 eq) was added dropwise while heating from 130 캜 to 140 캜 for 300 minutes. After the dropping of the alpha methylstyrene was completed, the reaction was further continued at the same temperature for 60 minutes.

Subsequently, sodium bicarbonate (0.268 g, 0.001 eq) was dissolved in distilled water, and the mixture was added at 90 to 100 ° C for neutralization for 60 minutes. The resulting solution was concentrated under reduced pressure at 135 ° C for 60 minutes to remove water, and then the neutralized salt was removed using a filter to obtain a purified alpha methyl styrene-phenol mixture.

Comparative Example

Phosphoric acid catalyst (1.873 g, 0.006 eq) was added to phenol (PhOH, 300 g, 1 eq) and alpha methylstyrene (AMS, 941.84 g, 2.5 eq) was added dropwise while heating from 130 占 폚 to 140 占 폚 for 300 minutes. After the dropping of the alpha methylstyrene was completed, the reaction was further continued at the same temperature for 60 minutes.

The composition of the alpha methyl styrene-naphthol phenol mixture prepared according to Examples 1 to 6 and Comparative Examples, before and after neutralization and concentration of the product, was analyzed by GC, and the results are shown in Tables 1 and 2, respectively.

division PhOH AMS AMS dimer OCP PCP DCP Example 1 4.67 0.16 4.95 3.28 58.16 27.2 Example 2 6.52 0.16 8.00 4.05 54.85 24.55 Example 3 1.56 0.73 11.66 2.49 47.49 32.34 Example 4 1.21 0.21 17.06 2.44 31.53 39.94 Example 5 1.06 0.3 20.04 2.34 28.04 39.25 Example 6 0.0 1.3 18.07 3.01 20.38 49.17 Comparative Example 7.92 7.41 62.97 0.2 19.23 0.88

(unit: %)

division PhOH AMS AMS dimer OCP PCP DCP Example 1 0.0 0.0 2.95 3.46 57.77 33.32 Example 2 0.0 0.0 6.91 3.61 54.93 28.97 Example 3 0.0 0.0 8.50 2.37 45.35 40.14 Example 4 0.0 0.0 14.43 2.46 30.16 45.81 Example 5 0.0 0.0 17.45 2.24 26.70 44.84 Example 6 0.0 0.0 16.57 3.07 20.05 51.28 Comparative Example 0.0 0.0 47.81 0.17 18.43 1.09

(unit: %)

Referring to Tables 1 and 2, the content of p-cumylphenol and dicumylphenol in the alpha methyl styrene-naphthol phenol mixture prepared through the production methods of Examples 1 to 6 was 20 to 60 wt% , Preferably, the content of p-cumylphenol and dicumylphenol is constantly in the range of 20 to 60 wt% and 30 to 60 wt%, respectively.

The total content of trimethylphenylindane (TMPI), diphenylmethylpentene (DMP) isomer, dicumene, AMS trimer and the like without hydroxyl group (-OH) in the resulting mixture of alpha methyl styrene naphthophenol By weight or less and 25% by weight or less, it can be advantageously applied as a non-reactive diluent excellent in plasticity and compatibility when added to the main part, the curing agent part, and the like of the epoxy coating composition.

It will be understood by those skilled in the art that the foregoing description of the present invention is for illustrative purposes only and that those of ordinary skill in the art can readily understand that various changes and modifications may be made without departing from the spirit or essential characteristics of the present invention. will be. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.

The scope of the present invention is defined by the appended claims, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be construed as being included within the scope of the present invention.

Claims (14)

An alpha methyl styrene-phenol mixture comprising a first component containing a hydroxyl group and a second component containing no hydroxyl group,
Wherein the first component comprises p-cumylphenol and dicumylphenol,
The content of the p-cumylphenol and the content of the dicumylphenol is 20 to 60% by weight based on the total weight of the alpha-methylstyrene-naphthol phenol mixture,
Wherein the content of the first component is at least 65% by weight based on the total weight of the alpha methyl styrene-naphthophenol mixture,
Wherein the second component comprises an alpha methyl styrene dimer (AMS dimer) and an alpha methyl styrene trimer (AMS trimer)
The content of the second component is 25% by weight or less based on the total weight of the alpha methyl styrene-naphthol phenol mixture,
Wherein the alpha methyl styrene naphthophene mixture does not comprise phenol. delete delete delete The method according to claim 1,
Wherein the alpha methyl styrene naphthophene mixture further comprises alpha methyl styrene. 6. The method of claim 5,
Wherein the content of alpha methyl styrene is 1 wt% or less based on the total weight of the alphamethyl styrene naphthophenol mixture. A non-reactive diluent for an epoxy paint, comprising an alpha methyl styrene naphthophenol mixture according to any one of claims 1, 5 and 6. (a) reacting 1 equivalent of phenol and 0.1-3.0 equivalents of alpha methyl styrene (AMS) in the presence of 0.0001 to 0.002 equivalents of an acid catalyst to produce an intermediate; And
(b) neutralizing and filtering said intermediate to obtain a mixture comprising a first product containing hydroxyl groups, a second product containing no hydroxyl groups, and an unreacted material,
Wherein the first product comprises p-cumylphenol and dicumylphenol,
Wherein the content of the p-cumylphenol and the dicumylphenol is 20 to 60% by weight based on the total weight of the mixture,
Wherein the content of the first product is at least 65% by weight based on the total weight of the mixture,
Wherein said second product comprises an alpha methyl styrene dimer and an alpha methyl trimer,
Wherein the content of the second product is 25% by weight or less based on the total weight of the mixture,
Wherein the unreacted material does not comprise phenol. &Lt; Desc / Clms Page number 24 &gt; 9. The method of claim 8,
Wherein the acid catalyst is one selected from the group consisting of sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, phosphoric acid, polyphosphoric acid, nitric acid, hydrochloric acid, boron trifluoride complex compound, acidic clay, ion exchange resin, A process for preparing an alpha methyl styrene substituted phenol mixture. delete delete delete delete 9. The method of claim 8,
Wherein the content of the unreacted material is 1 wt% or less based on the total weight of the mixture.