Polymer composition and coating composition comprising same

Abstract

The present invention provides a polymer composition comprising a polymer that comprises a unit derived from alpha-methyl styrene-based monomers, wherein the content of an indene-based compound derived from two alpha-methyl styrene-based monomers is 5 wt % or less relative to the total weight of the polymer composition, and the content of an indene-based compound derived from three alpha-methyl styrene-based monomers is 0.1 wt % or less relative to the total weight of the polymer composition. A coating film manufactured from the coating composition comprising the polymer composition may have excellent bending resistance, impact resistance, and chemical resistance.

Description

Polymer composition and paint composition comprising the same

[0001] The present invention relates to a polymer composition and a paint composition comprising the same.

[0002] Ships and heavy-duty structures are coated with a coating to protect the structure from harsh environments. Unlike land-based structures, this coating must not only withstand harsh corrosive environments, but also ensure safety and ease of maintenance.

[0003] The performance of the above paint is greatly influenced by the properties of the diluent mixed in. Conventional diluents for heavy-duty epoxy paints include various non-reactive components, such as alkyl phenol compounds such as nonyl phenol, dodecyl phenol, and octyl phenol, C5-C9 hydrocarbon resins, and oligomers of phenol and α-methylstyrene.

[0004] In particular, the above-mentioned alkyl phenol compounds have been widely used as additives or surfactants for heavy-duty epoxy paints requiring plasticity. However, the above-mentioned alkyl phenol compounds are known to be nephrotoxic and endocrine disruptors, and their use is currently banned worldwide or their scope of use is gradually being restricted.

[0005] Moreover, during the recent substance evaluation under EU REACH, alpha-methylstyrenated phenol (ALP) in phenol compounds was classified as a Substance of Very High Concern (SVHC), and in particular, the triaryl indane structure substance among ALP was confirmed to be very persistent (vP) and very bioaccumulative (vB). Accordingly, the need for the development of new diluents that do not fall under SVHC regulations by controlling the content of vPvB substances is increasing.

[0006] The present invention provides a polymer composition suitable for a paint composition by controlling the content of vPvB substances. In addition, the present invention provides a polymer composition capable of improving the bending resistance, impact resistance, and chemical resistance of a coating film prepared from the paint composition.

[0007] One aspect of the present invention relates to a polymer composition comprising a polymer including a unit derived from an alpha-methyl styrene monomer, wherein the content of an indene compound derived from two alpha-methyl styrene monomers is 5 wt% or less based on the total weight of the polymer composition, and the content of an indene compound derived from three alpha-methyl styrene monomers is 0.1 wt% or less based on the total weight of the polymer composition.

[0008] Another aspect of the present invention relates to a paint composition comprising the polymer composition.

[0009] The polymer composition according to the present invention comprises a polymer including a unit derived from an alpha-methyl styrene monomer, and the content of an indene compound derived from two alpha-methyl styrene monomers in the polymer composition is 5 wt% or less based on the total weight of the polymer composition, and the content of an indene compound derived from three alpha-methyl styrene monomers is 0.1 wt% or less based on the total weight of the polymer composition, so that a coating film manufactured from a paint composition including the polymer composition can have excellent bending resistance, impact resistance, and chemical resistance.

[0010] In addition, the polymer composition satisfies the content of the indene compound derived from three alpha-methyl styrene monomers of 0.1 wt% or less based on the total weight of the polymer composition, and thus can be applied as a diluent for an SVHC (Substance of Very High Concern) free eco-friendly paint.

[0011] Below, various aspects and various implementation examples of the present invention are described in more detail.

[0012] Terms or words used in this specification and claims should not be interpreted as limited to their usual or dictionary meanings, but should be interpreted as meanings and concepts that conform to the technical idea of ​​the present invention, based on the principle that the inventor can appropriately define the concept of the term to explain his or her own invention in the best way.

[0013] The terminology used herein is merely used to describe specific embodiments and is not intended to limit the present invention. The singular expression includes the plural expression unless the context clearly indicates otherwise. In the present invention, it should be understood that the terms "comprise" or "have" are intended to specify the presence of a feature, number, step, operation, component, part, or combination thereof described in the specification, but do not exclude in advance the possibility of the presence or addition of one or more other features, numbers, steps, operations, components, parts, or combinations thereof.

[0014] In the present invention, an alkyl group having 1 to 15 carbon atoms includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a pentene group, an octyl group, a nonyl group, a decene group, and the like.

[0015] In the present invention, the alkenyl group having 2 to 15 carbon atoms includes at least one unsaturated double bond. The alkenyl group having 2 to 15 carbon atoms includes an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a pentadiene, a hexenyl group, a hexadiene, a hexatriene, and the like.

[0016] Specifically, a polymer composition according to one aspect of the present invention is a polymer composition comprising a polymer including a unit derived from an alpha-methyl styrene monomer, wherein the content of an indene compound derived from two alpha-methyl styrene monomers may be 5 wt% or less based on the total weight of the polymer composition, and the content of an indene compound derived from three alpha-methyl styrene monomers may be 0.1 wt% or less based on the total weight of the polymer composition.

[0017] For example, the polymer composition satisfies the content of the indene compound derived from three alpha-methyl styrene monomers of 0.1 wt% or less based on the total weight of the polymer composition, and thus can be applied as a diluent for an SVHC (Substance of Very High Concern) free eco-friendly paint.

[0018] For example, the content of the indene compound derived from two alpha-methyl styrene monomers is 5 wt% or less, and the content of the indene compound derived from three alpha-methyl styrene monomers is 0.1 wt% or less, based on the total weight of the polymer composition, so that the coating film manufactured from the coating composition including the polymer composition can have excellent bending resistance, impact resistance, and chemical resistance.

[0019] For example, the content of the indene compound derived from three alpha-methyl styrene monomers in the polymer composition may be 0.05 wt% or less, 0.04 wt% or less, 0.03 wt% or less, 0.02 wt% or less, or 0.01 wt% or less based on the total weight of the polymer composition. For example, as the content of the indene compound derived from three alpha-methyl styrene monomers included in the polymer composition satisfies the above range, the polymer composition can be more easily applied as a diluent for an SVHC (Substance of Very High Concern) Free eco-friendly paint.

[0020] The above polymer composition can control the content of the indene compound derived from two alpha-methyl styrene monomers and the content of the indene compound derived from three alpha-methyl styrene monomers included in the polymer composition by using two or more types of catalysts together in the preparation process.

[0021] The above two or more catalysts may include PTSA (para-toluene sulfonic acid) and MAO solution (methylaluminoxane in toluene). When the above two or more catalysts include PTSA (para-toluene sulfonic acid) and MAO solution (methylaluminoxane in toluene), the content of the indene compound derived from two alpha-methyl styrene monomers included in the polymer composition and the content of the indene compound derived from three alpha-methyl styrene monomers can easily satisfy different ranges.

[0022] Preparation of the above polymer composition can be performed at a temperature range of 20 to 150°C.

[0023] According to one embodiment, the alpha-methyl styrene monomer may be represented by the following chemical formula 1.

[0024] <Chemical Formula 1>

[0025]

[0026] In the above chemical formula 1-1, R1 is hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, and a1 is an integer of 1 to 5.

[0027] For example, in the above chemical formula 1-1, R1 may be hydrogen, an alkyl group having 1 to 3 carbon atoms, or an alkenyl group having 2 to 3 carbon atoms, and a1 may be an integer of 1 to 5. In the above chemical formula 1-1, R1 may be hydrogen, a methyl group, or an isopropenyl group.

[0028] For example, the alpha-methyl styrene monomer may include alpha-methyl styrene.

[0029] According to one embodiment, the polymer composition may comprise only polymers comprising units derived from the alpha-methyl styrene monomer. For example, the polymer composition may not comprise units derived from a phenolic monomer.

[0030] According to one embodiment, the indene compound derived from three alpha-methyl styrene monomers can be represented by the following chemical formula 2.

[0031] <Chemical Formula 2>

[0032]

[0033] In the above chemical formula 2, R 21 Inland R 23 are each independently hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, a21 is an integer from 1 to 4, and a22 to a23 are each independently integers from 1 to 5.

[0034] For example, in the above chemical formula 2, R 21 Inland R 23 are independently hydrogen, an alkyl group having 1 to 3 carbon atoms, or an alkenyl group having 2 to 3 carbon atoms, a21 is an integer from 1 to 4, and a22 to a23 are independently integers from 1 to 5.

[0035] In the above chemical formula 2, R 21 Inland R 23 can be independently hydrogen, methyl or isopropenyl groups. In the above chemical formula 2, R 21 Inland R 23 Each can be hydrogen.

[0036] According to one embodiment, the indene compound derived from three alpha-methyl styrene monomers may include 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene.

[0037] According to one embodiment, the indene compound derived from two alpha-methyl styrene monomers may be represented by the following chemical formula 3.

[0038] <Chemical Formula 3>

[0039]

[0040] In the above chemical formula 3, R 31 and R 32 are independently hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, a31 is an integer from 1 to 4, and a32 is an integer from 1 to 5.

[0041] For example, in the above chemical formula 3, R 31 and R 32 are independently hydrogen, an alkyl group having 1 to 3 carbon atoms, or an alkenyl group having 2 to 3 carbon atoms, a31 may be an integer from 1 to 4, and a32 may be an integer from 1 to 5.

[0042] According to one embodiment, in the chemical formula 3, R 31 and R 32 can be hydrogen, methyl or isopropenyl group. In the above chemical formula 3, R 31 and R 32 Each can be hydrogen.

[0043] According to one embodiment, the indene compound derived from two alpha-methyl styrene monomers may include 1,3,3-trimethyl-1-phenylindene.

[0044] For example, the content of the indene compound derived from the two alpha-methyl styrene monomers included in the polymer composition may be 4.9 wt% or less, 4.85 wt% or less, 4.5 wt% or less, 4.0 wt% or less, 3.5 wt% or less, 3.0 wt% or less, 2.9 wt% or less, or 2.5 wt% or less. For example, the content of the indene compound derived from the two alpha-methyl styrene monomers included in the polymer composition is 0.01 to 5 wt%, 0.01 to 4.9 wt%, 0.01 to 4.85 wt%, 0.01 to 4.5 wt%, 0.01 to 4.0 wt%, 0.01 to 3.5 wt%, 0.01 to 3.0 wt%, 0.01 to 2.9 wt%, 0.01 to 2.5 wt%, 0.05 to 5 wt%, 0.05 to 4.9 wt%, 0.05 to 4.85 wt%, 0.05 to 4.5 wt%, 0.05 to 4.0 wt%, 0.05 to 3.5 wt%, 0.05 to 3.0 wt%, 0.05 It may be 2.9 wt% or 0.05 to 2.5 wt%.

[0045] According to one embodiment, the polymer composition may further comprise a pentene compound derived from two of the alpha-methyl styrene monomers.

[0046] For example, the pentene compound derived from the two alpha-methyl styrene monomers may include compounds represented by the following chemical formulas 4-1 and 4-2.

[0047] <Chemical Formula 4-1>

[0048]

[0049] <Chemical Formula 4-2>

[0050]

[0051] Among the above chemical formulas 4-1 to 4-2, R 41 and R 42are each independently hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, and a41 and a42 are each independently an integer from 1 to 5.

[0052] For example, among the chemical formulas 4-1 to 4-2, R 41 and R 42 are independently hydrogen, an alkyl group having 1 to 3 carbon atoms, or an alkenyl group having 2 to 3 carbon atoms, and a41 and a42 are independently integers of 1 to 5. In the above chemical formulas 4-1 to 4-2, R 41 and R 42 can be independently hydrogen, methyl or isopropenyl groups. In the above chemical formulas 4-1 to 4-2, R 41 and R 42 Each can be hydrogen.

[0053] According to one embodiment, the pentene compound derived from two of the alpha-methyl styrene monomers may include 2,4-diphenyl-4-methyl-1-pentene or 2,4-diphenyl-4-methyl-2(E)-pentene.

[0054] According to one embodiment, the content of the pentene compound derived from the two alpha-methyl styrene monomers may be 20 to 80 wt% based on the total weight of the polymer composition. The content of the pentene compound may be the sum of the content of the compound represented by the chemical formula 4-1 and the content of the compound represented by the chemical formula 4-2. The content of the pentene compound may be the sum of the content of 2,4-diphenyl-4-methyl-1-pentene and the content of 2,4-diphenyl-4-methyl-2(E)-pentene.

[0055] For example, the content of the pentene compound derived from the two alpha-methyl styrene monomers may be 25 to 80 wt%, 30 to 80 wt%, 32 to 80 wt%, 35 to 80 wt%, 20 to 70 wt%, 20 to 65 wt%, 20 to 63 wt%, or 30 to 65 wt% based on the total weight of the polymer composition.

[0056] According to one embodiment, the total content of the pentene compound derived from the two alpha-methyl styrene monomers and the indene compound derived from the two alpha-methyl styrene monomers may be 25 to 85 wt% based on the total weight of the polymer composition. For example, the total content of the pentene compound derived from the two alpha-methyl styrene monomers and the indene compound derived from the two alpha-methyl styrene monomers may be 30 to 85 wt%, 32 to 85 wt%, 25 to 70 wt%, 25 to 65 wt%, or 30 to 65 wt% based on the total weight of the polymer composition.

[0057] According to one embodiment, the polymer composition may further comprise a heptene compound derived from three of the alpha-methyl styrene monomers.

[0058] According to one embodiment, the heptene compound derived from three alpha-methyl styrene monomers may include a compound represented by the following chemical formula 5-1 or 5-2.

[0059] <Chemical Formula 5-1>

[0060]

[0061] <Chemical Formula 5-2>

[0062]

[0063] Among the above chemical formulas 5-1 to 5-2, R 51 Inland R 52are each independently hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, and a51 to a53 are each independently an integer from 1 to 5.

[0064] For example, among the chemical formulas 5-1 to 5-2, R 51 Inland R 62 5 are independently hydrogen, an alkyl group having 1 to 3 carbon atoms, or an alkenyl group having 2 to 3 carbon atoms, and a51 to a53 are independently integers of 1 to 5. In the above chemical formulas 5-1 to 5-2, R 51 Inland R 52 can be independently hydrogen, methyl or isopropenyl groups. In the above chemical formulas 5-1 to 5-2, R 51 Inland R 52 Each can be hydrogen.

[0065] According to one embodiment, the heptene compound derived from the three alpha-methyl styrene monomers may include 2,4,6-triphenyl-4,6-dimethyl-1-heptene or 2,4,6-triphenyl-4,6-dimethyl-2-heptene.

[0066] According to one embodiment, the content of the heptene compound derived from the three alpha-methyl styrene monomers may be 30 to 70 wt% with respect to the total weight of the polymer composition. The content of the heptene compound derived from the three alpha-methyl styrene monomers may be the sum of the content of the compound represented by the chemical formula 5-1 and the content of the compound represented by the chemical formula 5-2. The content of the heptene compound derived from the three alpha-methyl styrene monomers may be the sum of the content of 2,4,6-triphenyl-4,6-dimethyl-1-heptene and the content of 2,4,6-triphenyl-4,6-dimethyl-2-heptene.

[0067] For example, the content of the heptene compound derived from the three alpha-methyl styrene monomers may be 33 to 70 wt%, 35 to 70 wt%, 30 to 68 wt%, 30 to 65 wt%, or 33 to 68 wt% based on the total weight of the polymer composition.

[0068] According to one embodiment of the present invention, the viscosity of the polymer composition may be 20 to 3,000 cps. When the viscosity of the polymer composition satisfies the above range, the polymer composition for paint can be more easily introduced as a diluent for a paint composition described later. In addition, the processability and application properties of the paint composition described later can be improved. For example, the viscosity of the polymer composition may be 20 to 2,000 cps, 30 to 3,000 cps, 40 to 3,000 cps, or 40 to 2,000 cps.

[0069] According to one embodiment, the Gardner color value of the polymer composition may be 4 or less. For example, the Gardner color value of the polymer composition may be 3 or less, 2 or less, or 1.5 or less.

[0070] According to one embodiment, the weight average molecular weight (Mw) of the polymer composition may be from 100 g / mol to 400 g / mol, and the number average molecular weight (Mn) of the polymer composition may be from 100 g / mol to 400 g / mol.

[0071] For example, the weight average molecular weight (Mw) of the polymer composition may be 150 to 400 g / mol, 200 to 400 g / mol, 100 to 300 g / mol, or 200 to 300 g / mol.

[0072] For example, the number average molecular weight (Mn) of the polymer composition may be 50 to 400 g / mol, 200 to 400 g / mol, 100 to 300 g / mol, or 200 to 300 g / mol.

[0073] According to one embodiment, the polymer composition may be a polymer composition for an epoxy paint. For example, the polymer composition may be applied to a paint composition comprising an epoxy polymer.

[0074] Another aspect of the present invention provides a paint composition comprising the polymer composition for paint.

[0075] According to one embodiment, the coating composition may include an epoxy polymer and the above-described coating polymer composition. According to one embodiment, the epoxy polymer may be a bisphenol-A type epoxy polymer. For example, the bisphenol-A type epoxy polymer may be a polymerization reaction product of bisphenol A and epichlorohydrin.

[0076] According to one embodiment, the content of the paint polymer composition may be 1 to 30 wt% based on the total weight of the paint composition.

[0077] According to one embodiment, the paint composition may further comprise a pigment, a solvent or an additive.

[0078] Examples of the pigments include inorganic pigments or organic pigments. The inorganic pigments may be at least one selected from the group consisting of chromates (cyanide, chromium vermillion), ferrocyanide (cyanide), sulfides (cadmium yellow, cadmium red), oxides (titanium oxide, bengala, iron black, zinc oxide), sulfates (barium sulfate, lead sulfate), silicates (ultraviolet, calcium silicate), carbonates (calcium carbonate, magnesium carbonate), phosphates (cobalt violet), metal powders (aluminum powder, bronze), and carbon (carbon black).

[0079] The above organic pigment may be at least one selected from the group consisting of azo pigments (benzidine yellow, hanja yellow, vulcan orange, permanent red F5R, carmine 6B, lake red C, chromophthalic red, chromophthalic yellow) and phthalocyananiline pigments (phthalocyanine blue, phthalocyananiline green).

[0080] Examples of the above solvents include aromatic hydrocarbon solvents such as toluene, xylene, Solvexo #100, and Solvexo #150; aliphatic hydrocarbon solvents such as hexane, heptane, octane, and decane; and ester solvents such as methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, amyl acetate, ethyl formate, and butyl propionate. In addition, examples of water-miscible organic solvents that can be used include alcohol solvents such as methanol, ethanol, propanol, and butanol; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Examples of glycol ether solvents include ethylene glycol (mono, di) methyl ether, ethylene glycol (mono, di) ethyl ether, ethylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, monobutyl ether, diethylene glycol (mono, di) methyl ether, diethylene glycol (mono, di) ethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, triethylene glycol (mono, di) methyl ether, propylene glycol (mono, di) methyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, and dipropylene glycol (mono, di) methyl ether.

[0081] The above additives may include various lubricants, antifoaming agents, leveling agents, lubricants, curing agents, curing aids, etc. The curing agent may include an amine curing agent or an amide curing agent. The curing aid may include a melamine polymer, a benzoguanamine polymer, an isocyanate polymer, etc.

[0082] Hereinafter, the present invention will be described in more detail through examples. These examples are intended solely to illustrate the present invention more specifically, and it will be apparent to those skilled in the art that the scope of the present invention is not limited by these examples.

[0083] Example 1 (PTSA+MAO catalyst)

[0084] In a four-necked flask equipped with a stirrer, condenser, and thermometer, 333 g of xylene, 9 g (0.052 mol) of PTSA (Para-Toluene Sulfonic Acid), and 9 g of 10% MAO solution (Methylaluminoxane in Toluene) were added, the temperature was raised to 65°C, and the mixture was stirred for 30 minutes. At 65°C, 1,000 g (8.462 mol) of AMS (α-Methyl Styrene) was added dropwise evenly over 4 hours, and the mixture was aged for 1 hour.

[0085] After the reaction was completed, 4.2 g of 50% caustic soda and 173 g of water were added, the temperature was raised to 80°C, and stirred for 30 minutes. After allowing to stand for 30 minutes, water separation was performed to remove the lower layer of water. This process was repeated twice for washing, and the washing process was performed until the final lower layer reached a pH of 6 to 8. To remove the solvent (xylene), degassing was performed at 175°C and a pressure of less than 20 torr, thereby preparing a polymer composition.

[0086] The yield of the prepared polymer composition was 98.9%, the viscosity was 132 cps (@25°C), the NV was 98.42%, the color was Gardner color 0.7, the weight average molecular weight (Mw) was 235 g / mol, and the number average molecular weight (Mn) was 208 g / mol. As a result of GC-MS analysis, the content of TMPI (Trimethylphenylindane) included in the polymer composition was 2.88 wt%, and 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene was not detected. The contents of other components are shown in Table 1 below.

[0087] Example 2 (PTSA+MAO catalyst)

[0088] A polymer composition was prepared in the same manner as in Example 1, except that the reaction temperature was changed from 65°C to 30°C. The yield of the prepared polymer composition was 98.1%, the viscosity was 1970 cps (@25°C), the NV was 99.02%, the color was Gardner color 1.4, the weight average molecular weight (Mw) was 297 g / mol, and the number average molecular weight (Mn) was 280 g / mol. As a result of GC-MS analysis, the content of TMPI included in the polymer composition was 0.08 wt%, and 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene was not detected. The contents of other components are shown in Table 1 below.

[0089] Example 3 (PTSA+MAO catalyst)

[0090] A polymer composition was prepared in the same manner as in Example 1, except that the reaction temperature was changed from 65°C to 95°C. The yield of the prepared polymer composition was 98.7%, the viscosity was 87 cps (@25°C), the NV was 98.74%, the color was Gardner color 0.9, the weight average molecular weight (Mw) was 228 g / mol, and the number average molecular weight (Mn) was 201 g / mol. As a result of GC-MS analysis, the content of TMPI included in the polymer composition was 4.85 wt%, and 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene was not detected. The contents of other components are shown in Table 1 below.

[0091] Comparative Example 1 (BF 3· Phenolate catalyst)

[0092] BF instead of PTSA (Para-Toluene Sulfonic Acid) and 10% MAO solution (Methylaluminoxane in Toluene) as catalysts 3·A polymer composition was prepared in the same manner as in Example 1, except that the reaction was performed by changing 9 g of phenolate. The yield of the prepared polymer composition was 95.4%, the viscosity was 54 cps (@25°C), the NV was 96.35%, the color was Gardner color 3.2, the weight average molecular weight (Mw) was 229 g / eq, and the number average molecular weight (Mn) was 207 g / eq. As a result of GC-MS analysis, the content of TMPI contained in the polymer composition was 23.13 wt%, and the content of 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene was 4.58 wt%. The contents of other components are shown in Table 1.

[0093] Comparative Example 2 (BF3·Phenolate catalyst)

[0094] A polymer composition was prepared in the same manner as in Example 2, except that the reaction was performed using 9 g of BF3·Phenolate instead of PTSA (Para-Toluene Sulfonic Acid) and 10% MAO solution (Methylaluminoxane in Toluene) as a catalyst. The yield of the prepared polymer composition was 95.3%, the viscosity was 2180 cps (@25°C), the NV was 96.85%, the color was Gardner color 3.2, the weight average molecular weight (Mw) was 295 g / mol, and the number average molecular weight (Mn) was 273 g / mol. As a result of GC-MS analysis, the content of TMPI contained in the polymer composition was 15.65 wt%, and the content of 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene was 34.14 wt%. The contents of other components are shown in Table 1.

[0095] Comparative Example 3 (PTSA + 85% phosphoric acid catalyst)

[0096] A polymer composition was prepared in the same manner as in Example 3, except that 9 g (0.052 mol) of PTSA (Para-Toluene Sulfonic Acid) and 9 g of 85% phosphoric acid were used instead of PTSA (Para-Toluene Sulfonic Acid) and 10% MAO solution (Methylaluminoxane in Toluene) as a catalyst, and the reaction temperature was changed from 95°C to 115°C. The yield of the prepared polymer composition was 94.8%, the viscosity was 41 cps (@25°C), the NV was 96.29%, the color was Gardner color 3.4, the weight average molecular weight (Mw) was 228 g / mol, and the number average molecular weight (Mn) was 197 g / mol. According to the GC-MS analysis results, the TMPI content in the polymer composition was 6.11 wt%, and the 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene content was 0.82 wt%. The contents of other components are shown in Table 1.

[0097] Compound Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 1,3-Dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene NDNDND 4.58 34.14 0.82 Trimethylphenylindene (TMPI) 2.88 0.08 4.85 23.13 15.65 6.11 2,4-Diphenyl-4-methyl-1-pentene 23.77 10.58 16.31 12.39 4.78 22.292,4-Diphenyl-4-methyl-2(E)-pentene39.0221.3533.2828.579.0342.182,4,6-Triphenyl-4,6-dimethyl-1-heptene22.6242.8331.3522.3022.8418.472,4,6-Triphenyl-4,6-dimethyl-2-heptene11.1424.4813.668.1612.979.76

[0098] Evaluation Example 1 (Film Performance Evaluation)

[0099] Film formation

[0100] Liquid paints were prepared using the polymer compositions of Examples 1 to 3 and Comparative Examples 1 to 3 as a diluent, and a coating film was formed.

[0101] In a circular plastic container, 284 g of liquid bisphenol-A type epoxy resin (KE-8128, commercially available from Kolon Industries) and 28.4 g of the polymer compositions prepared according to Examples 1 to 3 and Comparative Examples 1 to 3 were each added, along with 42 g of xylene and 10 g of MIBK, and stirred.

[0102] 0.6g of wetting agent was added to each circular plastic container, and 21.5g of bentonite (Viscogen138) was added little by little using a high-speed mixer, and the mixture was stirred vigorously until the bentonite particles were no longer visible. Next, 117g of TiO2, 358g of talc, 4.8g of iron oxide black, and 113g of barium sulfate (BaSO4) were added, and then 23g of solvent xylene and 25g of MIBK were additionally added, and the mixture was stirred at a speed of 1000 rpm for 15 minutes.

[0103] Glass beads were added to the stirred mixture at a rate of 1.5 paper cups. The mixture was dispersed using a shaker, and the particle size was measured every 20 minutes. Dispersion was terminated when the particle size was 40 μm or less. The glass beads were filtered out to prepare a paint composition.

[0104] A composition was prepared by mixing a phenalkamine-based hardener LITE 2002 (AHEW = 104 g / eq) and a prepared paint composition at an epoxy and active hydrogen equivalent ratio of 1:1. Thereafter, the composition was applied to glass and iron specimens in thicknesses of 75 μm and 120 μm, respectively, and completely dried at room temperature to form a coating film.

[0105] The physical properties of the formed film were measured using the following method.

[0106] (1) Flexural adhesion (flexural resistance) (ASTM E643, Erichsen Cupping test): When each of the above coating films was subjected to gradual deformation by indentation (pressing and pushing), the resistance to cracking and peeling from the metal substrate was evaluated. The measurement results are shown in Table 2 below.

[0107] (2) Impact resistance (ASTM D2794): Using a Dupont impact tester, a weight with a load of 1 kg was dropped from a low height (400 mm) on each of the above coatings, and the height at which each coating peeled (cracked) was measured. The measurement results are shown in Table 2 below.

[0108] (3) Content resistance and acid / alkali resistance: Xylene, 5% sulfuric acid solution, and 5% caustic soda were dropped onto the surface of each coating, and left at room temperature for 72 hours. The degree of damage to the coating was visually assessed. If the degree of damage to the coating was high, it was evaluated as 1 (Bad), and if it was low, it was evaluated as 10 (Good). The measurement results are shown in Table 2 below.

[0109] Flexural strength (mm) Impact resistance (1000N*mm) Chemical resistance Acid / base resistance Example 16.2365099 / 9 Example 26.8965099 / 9 Example 36.0265088 / 8 Comparative example 14.0845066 / 6 Comparative example 24.2145077 / 7 Comparative example 35.4650077 / 7

[0110] As shown in Table 2 above, the paint composition including the polymer composition according to the example improved the bending resistance, impact resistance, and chemical resistance of the produced coating film.

[0111] Therefore, the paint composition according to the present invention can easily realize a paint film with improved bending resistance, impact resistance, and chemical resistance.

[0112] The above-described examples and comparative examples are illustrative of the present invention and are not intended to limit the scope of the present invention. Those skilled in the art will be able to implement the present invention by making various modifications based on the examples provided. Therefore, the technical protection scope of the present invention should be defined by the appended claims.

Claims

1. A polymer composition comprising a polymer including a unit derived from an alpha-methyl styrene monomer, The content of the indene compound derived from two alpha-methyl styrene monomers is 5 wt% or less based on the total weight of the polymer composition, A polymer composition, wherein the content of an indene compound derived from three alpha-methyl styrene monomers is 0.1 wt% or less based on the total weight of the polymer composition.

2. In paragraph 1, The above alpha-methyl styrene monomer is a polymer composition represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, R1 is hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, a1 is an integer from 1 to 5.

3. In paragraph 1, The indene compound derived from the three alpha-methyl styrene monomers is a polymer composition represented by the following chemical formula 2: <Chemical Formula 2> In the above chemical formula 2, R 21 Inland R 23 are independently hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, a21 is an integer from 1 to 4, a22 and a23 are integers from 1 to 5, independently of each other.

4. In paragraph 1, A polymer composition comprising an indene compound derived from three of the above alpha-methyl styrene monomers, wherein the indene compound comprises 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindene.

5. In paragraph 1, The indene compound derived from the two alpha-methyl styrene monomers is a polymer composition represented by the following chemical formula 3: <Chemical Formula 3> In the above chemical formula 3, R 31 and R 32 are independently hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, a31 is an integer from 1 to 4, a32 is an integer from 1 to 5.

6. In paragraph 1, A polymer composition comprising an indene compound derived from two of the above alpha-methyl styrene monomers, wherein the indene compound comprises 1,3,3-trimethyl-1-phenylindene.

7. In paragraph 1, A polymer composition further comprising a pentene compound derived from two alpha-methyl styrene monomers.

8. In paragraph 7, A polymer composition comprising a pentene compound derived from two alpha-methyl styrene monomers, the compound represented by the following chemical formulae 4-1 to 4-2: <Chemical Formula 4-1> <Chemical Formula 4-2> Among the above chemical formulas 4-1 to 4-2, R 41 and R 42 are independently hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, a41 and a42 are integers from 1 to 5, independently of each other.

9. In paragraph 7, A polymer composition in which the content of the pentene compound derived from the two alpha-methyl styrene monomers is 20 to 80 wt% based on the total weight of the polymer composition.

10. In paragraph 7, A polymer composition in which the total content of the pentene compound derived from the two alpha-methyl styrene monomers and the indene compound derived from the two alpha-methyl styrene monomers is 25 to 85 wt% based on the total weight of the polymer composition.

11. In paragraph 1, A polymer composition further comprising a heptene compound derived from three alpha-methyl styrene monomers.

12. In paragraph 11, A polymer composition comprising a heptene compound derived from three alpha-methyl styrene monomers, the compound represented by the following chemical formula 5-1 or 5-2: <Chemical Formula 5-1> <Chemical Formula 5-2> Among the above chemical formulas 5-1 to 5-2, R 51 Inland R 52 are independently hydrogen, an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, a51 to a53 are integers from 1 to 5, independently of each other.

13. In paragraph 12, A polymer composition in which the content of the heptene compound derived from the three alpha-methyl styrene monomers is 30 to 70 wt% based on the total weight of the polymer composition.

14. A paint composition comprising a polymer composition according to paragraph 1.

15. In paragraph 14, A paint composition further comprising an epoxy polymer.

Images