WO2016080503A1 - Matériau de revêtement en poudre - Google Patents

Matériau de revêtement en poudre Download PDF

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Publication number
WO2016080503A1
WO2016080503A1 PCT/JP2015/082610 JP2015082610W WO2016080503A1 WO 2016080503 A1 WO2016080503 A1 WO 2016080503A1 JP 2015082610 W JP2015082610 W JP 2015082610W WO 2016080503 A1 WO2016080503 A1 WO 2016080503A1
Authority
WO
WIPO (PCT)
Prior art keywords
powder coating
epoxy resin
hours
coating material
type epoxy
Prior art date
Application number
PCT/JP2015/082610
Other languages
English (en)
Japanese (ja)
Inventor
弘光 根岸
文幸 佐々木
Original Assignee
ソマール株式会社
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
Application filed by ソマール株式会社 filed Critical ソマール株式会社
Priority to JP2016560293A priority Critical patent/JP6732657B2/ja
Publication of WO2016080503A1 publication Critical patent/WO2016080503A1/fr

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
    • C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
    • C09D161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/03—Powdery paints

Definitions

  • the present invention relates to a powder coating, and more particularly to a powder coating suitable for forming a coating film on a molded product such as an automobile part.
  • resin-based coatings are used for automobiles, including insulation coatings for motors and generators.
  • the methods for producing these coatings include a method using a liquid varnish and a method using a powder coating. From the viewpoint of production efficiency, work environment, reuse of coating, etc., powder coating using a powder coating is used. Is considered advantageous.
  • Patent Document 1 discloses an epoxy resin having a naphthalene skeleton in 100 parts by weight of an epoxy resin powder containing an epoxy resin having a melting point of 90 ° C. to 140 ° C., an average molecular weight of 1000 to 4000, and an epoxy equivalent of 800 to 4000, and a curing agent.
  • a thermosetting epoxy resin powder coating containing 1 to 10 parts by weight of is disclosed.
  • Patent Document 1 as a curing agent, an amine curing agent, an acid curing agent, an acid anhydride curing agent, a polyamide curing agent, a phenolic hydroxyl group-containing curing agent, a dicyandiamide curing agent, a cationic polymerization reaction curing agent.
  • a curing agent an amine curing agent, an acid curing agent, an acid anhydride curing agent, a polyamide curing agent, a phenolic hydroxyl group-containing curing agent, a dicyandiamide curing agent, a cationic polymerization reaction curing agent.
  • hydrazine-based curing agents and the like are shown.
  • an object of this invention is to provide the powder coating material for manufacturing the coating film which is excellent in heat resistance and can maintain the outstanding performance over a long period of time in the high temperature environment of 250 degreeC or more.
  • the present inventors have found that the above problems can be solved by using a powder coating containing an epoxy resin having an naphthalene skeleton and an aralkyl resin, and have arrived at the present invention.
  • the powder coating material of the present invention contains a naphthalene type epoxy resin and an aralkyl resin.
  • the aralkyl resin is preferably a phenol aralkyl resin.
  • the time required for the residual weight to reach 95% of the initial weight at 250 ° C. calculated by the Flynn-Wall-Ozawa method of the powder coating of the present invention is preferably 10 hours or more.
  • the molded article of the present invention is provided with a coating film coated with the above powder coating material.
  • the powder coating of the present invention can provide a coating film that has excellent heat resistance and can maintain excellent performance over a long period of time in a high temperature environment of 250 ° C. or higher.
  • the powder coating material of the present invention contains a naphthalene type epoxy resin and an aralkyl resin. Below, the detail of the powder coating material of this invention is demonstrated.
  • Epoxy resin In the powder coating of the present invention, a naphthalene type epoxy resin is used as the main epoxy resin.
  • a naphthalene type epoxy resin having a rigid skeleton exhibits a high glass transition temperature (Tg).
  • Tg glass transition temperature
  • a naphthalene type epoxy resin having a naphthalene skeleton having a planar structure has a small steric hindrance, so that the nucleophilic attack of the curing agent is hardly inhibited. For this reason, the curing reaction proceeds in a relatively short time. Since naphthalene type epoxy resin has a condensed ring structure, it has long-term heat resistance.
  • the naphthalene type epoxy resin used for this invention is not specifically limited, The naphthalene type epoxy resin represented by Formula (1), Formula (2), Formula (3), etc., and mixtures thereof can be used. Examples of commercially available products include EPICLON HP-4700, HP-4710, HP-4770, HP-6000 (above, manufactured by DIC Corporation) and the like. In order to improve the brittleness of the resulting coating film, the number of functional groups of the naphthalene type epoxy resin is preferably 2 to 4, and is particularly preferably 2.
  • the softening point of the naphthalene type epoxy resin used in the present invention is preferably 60 ° C. or higher and 120 ° C. or lower.
  • the temperature is lower than 60 ° C., the storage stability after the powder coating material may be deteriorated.
  • the temperature is higher than 120 ° C., it may cause the roughness of the coating surface.
  • a powder coating using a naphthalene type epoxy resin having a softening point in the above range a coating film having an excellent appearance is obtained, and productivity is improved.
  • problems such as powder melting and solidifying during storage hardly occur, and storage stability is improved.
  • you may add epoxy resins other than a naphthalene type epoxy resin if desired in the range which does not impair the effect of this invention. It is preferable that the compounding quantity is 40 mass% or less of all the epoxy resins.
  • an aralkyl resin is used as a curing agent.
  • an aralkyl resin as a curing agent for a naphthalene type epoxy resin
  • the long-term stability of the cured film is improved, and the performance of the film is maintained even after being held for a long time in a high-temperature environment. This is because there are few structures that cause thermal decomposition in the cured product. Since the powder coating material of the present invention has such a high heat-resistant structure and good film formability and adhesiveness, a coating film having high heat resistance can be easily obtained by coating.
  • the aralkyl resin is represented by the following general formula (4). Among these, a phenol aralkyl resin in which Ar 2 is phenol is preferable because it is easily available and has excellent oxygen barrier properties.
  • Ar 1 is a phenyl group, a biphenyl group, a fluorenyl group, or a naphthyl group
  • Ar 2 is a group represented by the following general formula (5-1) or (5-2).
  • R represents a hydrogen atom, a hydrocarbon group having 1 to 15 carbon atoms, a trifluoromethyl group, an allyl group or an aryl group, and may be the same or different from each other.
  • m represents an integer of 0 to 3, and may be the same or different. If they are different, they may be arranged in any order.
  • n represents an average value of the number of repetitions of 1 to 10.
  • the curing agent has the aralkyl skeleton.
  • an epoxy-modified aralkyl resin was added to the main agent, the excellent effect of the present invention could not be obtained when no aralkyl resin was used as a curing agent.
  • the same effect as in the present invention can be obtained.
  • the proportion of the aralkyl resin used is preferably 0.6 to 1.2 equivalents, more preferably 0.7 to 1.0 equivalents, in terms of functional group equivalents per epoxy equivalent of the naphthalene type epoxy resin. preferable.
  • additives can be added to the powder coating material of the present invention as necessary within a range not impairing the effects of the invention.
  • the additive include a filler, a leveling agent, a colorant, a curing accelerator, an antifoaming agent, an adhesion improver, and an impact modifier.
  • the filler examples include silica, alumina, aluminum hydroxide, magnesium oxide, calcium carbonate, talc, mica, clay, and cellulose. By adding these fillers, the flow of the powder coating material can be more suitably controlled. In addition, these fillers may be used individually by 1 type, or may mix and use 2 or more types.
  • the manufacturing method of the powder coating material of this invention is not specifically limited, For example, it can manufacture with the following method.
  • a filler to a powder coating material
  • a naphthalene type epoxy resin and a filler are mixed.
  • the mixing method include melt mixing using a kneader or an extruder.
  • the mixing temperature and mixing time are not particularly limited, and are set according to the type and composition ratio of the raw materials.
  • the mixing temperature is preferably 70 ° C. to 150 ° C., more preferably 100 ° C. to 140 ° C.
  • the mixing time depends on the mixing method and the like, but in the case of a kneader, it is preferably 15 minutes to 60 minutes, more preferably 30 minutes to 50 minutes. In the case of an extruder, it is preferably 60 seconds or shorter, and more preferably 30 seconds or shorter. Thereafter, the obtained mixture is cooled and solidified, and coarsely pulverized. An aralkyl resin and other additives as required are added to the coarsely pulverized product, melt mixed, and then cooled and solidified. Thereafter, the solidified mixture is pulverized and classified to obtain a powder coating material.
  • the powder coating of the present invention contains a naphthalene type epoxy resin and an aralkyl resin. Depending on the mixing conditions, partial polymerization proceeds, and a polymer containing a structural unit derived from a naphthalene type epoxy resin and a structural unit derived from an aralkyl resin is contained.
  • the particle diameter of the powder coating material of the present invention is not particularly limited, but the volume average particle diameter by laser diffraction / scattering method (JIS 8825-1) is preferably in the range of 30 ⁇ m to 70 ⁇ m.
  • the volume average particle size can be measured using a laser diffraction particle size distribution analyzer (manufactured by SYMPATEC, HELOS and PODOS analysis software: WINDOX5).
  • a laser diffraction particle size distribution analyzer manufactured by SYMPATEC, HELOS and PODOS analysis software: WINDOX5
  • the horizontal flow rate of the powder coating of the present invention is preferably in the range of 1 to 50%.
  • a powder paint having a large horizontal flow rate has a low viscosity when melted and the paint flows easily, whereas a powder paint having a small horizontal flow rate has a high viscosity and hardly flows when melted.
  • the horizontal flow rate of the powder coating is more preferably 5% to 30%. The horizontal flow rate is calculated by the following method.
  • 1 g of the powder coating material is put into a tablet molding die having an inner diameter of 16 mm ⁇ , and the diameter (a) of the tablet obtained by pressurizing with a load of 90 MPa for 60 seconds is measured with a caliper.
  • the tablet is placed on a slide glass, heated in a hot air dryer at 140 ° C. for 10 minutes, and the tablet diameter (b) is measured in the same manner.
  • the horizontal flow rate (%) is obtained by multiplying the value obtained by dividing the increase in diameter (ba) by heating by the diameter (a) before heating by 100.
  • the softening temperature of the powder coating material of the present invention is preferably 60 ° C. or higher and 120 ° C. or lower.
  • the softening point of the powder coating within the above range, the productivity of the coating film is improved, and a coating film having a more excellent appearance can be obtained.
  • dissolving and solidifying during storage do not arise easily and storage stability improves.
  • the time required for the residual weight to reach 95% of the initial weight at 250 ° C. is preferably 10 hours or more.
  • this value can be calculated by the Flynn-Wall-Ozawa method using the result of the thermogravimetric change of the powder paint measured using a differential thermothermogravimetric simultaneous analysis (TG / DTA) apparatus.
  • TG / DTA differential thermothermogravimetric simultaneous analysis
  • the behavior of the thermogravimetric change can be adjusted by the kind and blending amount of the naphthalene type epoxy resin used for the powder coating material of the present invention.
  • the method of applying the powder coating of the present invention is not particularly limited, and a known coating method can be applied. Specifically, electrostatic coating, triboelectric charging, non-charged coating, fluid immersion, and the like can be given. According to the above method, a coating film can be obtained by applying a powder coating on the surface of the object to be coated and then curing. If necessary, the adhesion of the coating film can be improved by applying a surface treatment to the object to be coated in advance. Although the film thickness of the coating film obtained from the powder coating material of this invention is not specifically limited, 50 micrometers or more and 500 micrometers or less are preferable.
  • Examples 1-2, Comparative Examples 1-3 The main component and curing agent were mixed together with a leveling agent and a curing accelerator at a blending ratio (mass) shown in Table 1 with a mixer, and then melt mixed with an extruder.
  • the mixing temperature was 110 ° C.
  • the mixing time was 30 seconds or less.
  • the mixture was cooled and solidified, and then finely pulverized to obtain powder coating materials of Examples and Comparative Examples.
  • a filler such as an inorganic filler is not added.
  • 1 mass part of imidazole was added with respect to 100 mass parts of main agents as a hardening accelerator. Table 1 shows the result of calculating the estimated time until the residual weight of the obtained powder coating material reaches 95% at 250 ° C. by the method described later.
  • Example 4 Comparative Examples 4 to 6, Reference Example 1
  • the above main agent and filler were melt-mixed with an extruder at the blending ratio (mass) shown in Table 2, then cooled and solidified, and coarsely pulverized.
  • the curing agent shown in Table 2 was added together with a leveling agent and a curing accelerator, mixed with a mixer, and then melt mixed with an extruder.
  • the mixing temperature was 110 ° C.
  • the mixing time was 30 seconds or less.
  • the mixture was cooled and solidified, and then finely pulverized to obtain powder coating materials of Examples, Comparative Examples, and Reference Examples.
  • silica was used as the filler.
  • thermogravimetric change of the powder coating sample of an Example, a comparative example, and a reference example was measured using the differential thermal thermogravimetric simultaneous analysis (TG / DTA) apparatus.
  • TG / DTA differential thermal thermogravimetric simultaneous analysis
  • the temperature increase rate was measured at 5 K / min, 10 K / min, 20 K / min, and 30 K / min, respectively. From each of the results, the temperature when the residual amount reached 95% by weight of the initial weight was read, and the residual amount was 95% of the initial weight at 250 ° C. by the Flynn-Wall-Ozawa method, which is one of the equivariant rate methods. Estimated time to be calculated.
  • Example 4 of the present invention using a naphthalene type epoxy resin and biphenyl aralkyl phenol, the tensile strength maintenance ratios after holding for 200 hours and after holding for 1000 hours were 63% and 59%, respectively.
  • the coating film tensile strength maintenance rate is required to be 50% or more after both 200 hours and 1000 hours.
  • the above requirement may be satisfied. all right.
  • the value of the tensile strength maintenance ratio after holding for 1000 hours / the tensile strength maintenance ratio after holding for 200 hours is as high as 0.94. After holding for 200 hours, the physical properties of the coating film at high temperature It was confirmed that the change was remarkably suppressed.
  • the values of the tensile strength maintenance ratio after holding for 1000 hours / the tensile strength maintenance ratio after holding for 200 hours were 0.83, 0.83, and 0.76, which were not as high as those of Example 4.
  • biphenylaralkyl type epoxy resin was used as the main agent, but sufficient effects were not obtained. From this, it is considered effective to use a resin having an aralkyl skeleton as the curing agent as in the present invention.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Laminated Bodies (AREA)

Abstract

Le problème de l'invention concerne un matériau de revêtement en poudre pour produire un revêtement qui présente une meilleure résistance à la chaleur et qui peut maintenir des propriétés supérieures sur une longue période de temps dans un environnement à haute température de 250°C ou plus. La solution porte sur la préparation d'un matériau de revêtement en poudre contenant une résine époxy de naphtalène et une résine d'aralkyle. Une résine d'aralkyle de phénol est utilisée en tant que résine aralkyle. Le matériau de revêtement en poudre est préparé de manière telle qu'il faut au moins 10 heures pour que le poids résiduel représente 95 % du poids initial, à 250°C, comme calculé par le procédé de Flynn-Wall-Ozawa (FWO).
PCT/JP2015/082610 2014-11-20 2015-11-19 Matériau de revêtement en poudre WO2016080503A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2016560293A JP6732657B2 (ja) 2014-11-20 2015-11-19 粉体塗料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014235943 2014-11-20
JP2014-235943 2014-11-20

Publications (1)

Publication Number Publication Date
WO2016080503A1 true WO2016080503A1 (fr) 2016-05-26

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PCT/JP2015/082610 WO2016080503A1 (fr) 2014-11-20 2015-11-19 Matériau de revêtement en poudre

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JP (1) JP6732657B2 (fr)
TW (1) TWI675076B (fr)
WO (1) WO2016080503A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017002208A (ja) * 2015-06-11 2017-01-05 ソマール株式会社 粉体塗料
WO2018163929A1 (fr) * 2017-03-08 2018-09-13 三菱マテリアル株式会社 Composition liquide filmogène à faible indice de réfraction et procédé de formation d'un film à faible indice de réfraction en utilisant celle-ci

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06116514A (ja) * 1992-10-02 1994-04-26 Nippon Kayaku Co Ltd 可撓性粉体塗料組成物
JPH1017793A (ja) * 1996-07-02 1998-01-20 Mitsui Petrochem Ind Ltd エポキシ樹脂系粉体塗料組成物
JP2003286436A (ja) * 2002-03-28 2003-10-10 Kansai Paint Co Ltd 熱硬化型エポキシ樹脂粉体塗料
JP2004256622A (ja) * 2003-02-25 2004-09-16 Dainippon Ink & Chem Inc エポキシ樹脂用硬化剤
JP2012229312A (ja) * 2011-04-25 2012-11-22 Air Water Inc フェノール系重合体、その製法およびその用途

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06116514A (ja) * 1992-10-02 1994-04-26 Nippon Kayaku Co Ltd 可撓性粉体塗料組成物
JPH1017793A (ja) * 1996-07-02 1998-01-20 Mitsui Petrochem Ind Ltd エポキシ樹脂系粉体塗料組成物
JP2003286436A (ja) * 2002-03-28 2003-10-10 Kansai Paint Co Ltd 熱硬化型エポキシ樹脂粉体塗料
JP2004256622A (ja) * 2003-02-25 2004-09-16 Dainippon Ink & Chem Inc エポキシ樹脂用硬化剤
JP2012229312A (ja) * 2011-04-25 2012-11-22 Air Water Inc フェノール系重合体、その製法およびその用途

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017002208A (ja) * 2015-06-11 2017-01-05 ソマール株式会社 粉体塗料
WO2018163929A1 (fr) * 2017-03-08 2018-09-13 三菱マテリアル株式会社 Composition liquide filmogène à faible indice de réfraction et procédé de formation d'un film à faible indice de réfraction en utilisant celle-ci
CN110291165A (zh) * 2017-03-08 2019-09-27 三菱综合材料株式会社 低折射率膜形成用液体组合物及使用该组合物的低折射率膜的形成方法

Also Published As

Publication number Publication date
TWI675076B (zh) 2019-10-21
JP6732657B2 (ja) 2020-07-29
JPWO2016080503A1 (ja) 2017-09-28
TW201619301A (zh) 2016-06-01

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