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WO2018025669A1 - Composition de revêtement - Google Patents

Composition de revêtement Download PDF

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Publication number
WO2018025669A1
WO2018025669A1 PCT/JP2017/026501 JP2017026501W WO2018025669A1 WO 2018025669 A1 WO2018025669 A1 WO 2018025669A1 JP 2017026501 W JP2017026501 W JP 2017026501W WO 2018025669 A1 WO2018025669 A1 WO 2018025669A1
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WO
WIPO (PCT)
Prior art keywords
polyester resin
parts
acid
production example
resin varnish
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.)
Ceased
Application number
PCT/JP2017/026501
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English (en)
Japanese (ja)
Inventor
瑛 齋藤
翔矢 佐藤
歩未 小澤
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.)
Toyochem Co Ltd
Artience Co Ltd
Original Assignee
Toyo Ink SC Holdings Co Ltd
Toyochem Co Ltd
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 Toyo Ink SC Holdings Co Ltd, Toyochem Co Ltd filed Critical Toyo Ink SC Holdings Co Ltd
Publication of WO2018025669A1 publication Critical patent/WO2018025669A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B32B15/09—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyesters
    • 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
    • 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
    • C09D161/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols with polyhydric 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds

Definitions

  • the present invention relates to a coating composition.
  • BPA type epoxy resin synthesized from bisphenol A (hereinafter also referred to as “BPA”) and epichlorohydrin forms a coating film with excellent steam sterilization resistance (retort resistance), processability and adhesion.
  • BPA bisphenol A
  • epichlorohydrin forms a coating film with excellent steam sterilization resistance (retort resistance), processability and adhesion.
  • retort resistance steam sterilization resistance
  • adhesion resistance As a result, it has been widely used as a coating for coating the inner and outer surfaces of cans.
  • BPA has the effect of disrupting the endocrine activity of organisms, and it was listed in 67 substances in the list of “chemical substances suspected of having endocrine disrupting activity” published by the Ministry of the Environment.
  • BPA eluted into the contents from the coating film covering the inner surface of the can. Therefore, a can coating material that does not use any BPA-derived raw material has been demanded.
  • the paint that coats the inner surface of the can can be processed at the time of molding of the can member in addition to flavor resistance, corrosion resistance, retort resistance, etc. that do not impair the flavor of the contents.
  • the lid member has a shape with many irregularities and is subjected to advanced molding processing as compared with other members. Therefore, the coating film formed on the lid member requires particularly high workability. .
  • the coating film needs to have acid resistance and alkali resistance, and in addition to the above-mentioned physical properties, a paint satisfying acid resistance and alkali resistance is required. It was.
  • beverage cans and food cans may be subjected to high temperature retort treatment for the purpose of sterilizing the contents after filling the contents into the can depending on the type of the contents. Therefore, when the retort resistance of the inner surface coating film is not sufficient, components in the coating film may be eluted in the contents during the retort treatment, which is not preferable for hygiene. In addition, when the retort resistance of the coating film is poor, the coating film component may be eluted into the contents even when the retort treatment is not performed and the film is stored at room temperature. As described above, the inner surface coating film of the can is required to have such resistance that the component hardly dissolves into the contents.
  • the property of the components in the coating film that hardly dissolve into the content is referred to as “content contamination resistance”.
  • This resistance to content contamination is usually estimated by the amount of organic components eluted from the coating film. The smaller the amount of the organic component to be eluted, the better the resistance to content contamination.
  • beverage cans filled with carbonated beverages are returned to room temperature after the contents are filled at a low temperature of about 5 ° C. and a lid is attached.
  • the carbonic acid volatilizes and the pressure inside the can increases, so the lid portion of the can swells outward due to the pressure from the inside.
  • the volatilization from the filler of carbonic acid and the dissolution in the filler are repeated due to the change in the ambient temperature, and the lid repeats the uneven change.
  • the lid is deformed in a state in which the contents are filled, and corrosion of the deformed portion is likely to occur. Therefore, various processes are performed on the lid portion in consideration of such deformation due to pressure.
  • the coating composition Since these various processes are performed after the coating film is provided on both sides of the lid material, the coating composition has high processability so as not to cause a coating film defect in various processes, and the lid is uneven after filling the contents. High corrosion resistance is required so that corrosion does not occur even when the state changes are repeated. In particular, as a recent consumer trend, beverages that appeal to strong stimulation with strong carbonic acid are increasing, and high low-temperature workability that can withstand this high gas pressure is required.
  • Patent Document 1 includes a polyester resin having a glass transition temperature of 35 to 100 ° C., a mixed polyester resin obtained by mixing a polyester resin having a glass transition temperature of ⁇ 20 to 25 ° C., a curing agent, and a curing catalyst.
  • a coating composition is disclosed.
  • Patent Document 2 discloses a coating composition comprising a polyester resin having a glass transition temperature of 0 ° C. or higher, a mixed polyester resin in which a polyester resin having a glass transition temperature of less than 0 ° C. is mixed, a resol type phenol resin, and an acidic curing catalyst. Things are disclosed.
  • the paint of Patent Document 1 improves the workability of the coating film over time by using two types of polyester resins having different glass transition temperatures, but on the other hand, the workability at low temperatures is reduced. There was a problem.
  • the paint of Patent Document 2 also improves the workability of the coating film over time by using two types of polyester resins having different glass transition temperatures. In addition, there is a problem that the alkali resistance decreases.
  • An object of the present invention is to provide a coating composition capable of forming a coating film having excellent processability at low temperatures and alkali resistance, and further having excellent adhesion to metal.
  • the coating composition of the present invention comprises a polyester resin (A) having an acid value of 30 mgKOH / g or less and a glass transition temperature of 30 to 130 ° C., a polyester resin (B) having an acid value of 30 mgKOH / g or less and a glass transition temperature of less than ⁇ 20 ° C. ) And phenol resin (C).
  • a coating composition capable of forming a coating film having excellent processability at low temperatures and alkali resistance, and having excellent adhesion to metal.
  • the polycarboxylic acid (a) includes a compound in which a carboxyl group in the polycarboxylic acid is esterified with a monoalcohol such as methanol or ethanol, and an acid anhydride of the polycarboxylic acid.
  • a monoalcohol such as methanol or ethanol
  • an acid anhydride of the polycarboxylic acid an acid anhydride of the polycarboxylic acid.
  • trimellitic anhydride is a compound having three carboxyl groups.
  • the content resistance property refers to the property that the coating film is not easily damaged by the contents of the can, and the main contents that affect the inner surface of the can are acidic food, salt, fish meat, and the like. Acidic foods corrode iron, the material of cans, and salt oxidizes iron. Fish meat also contains trace amounts of sulfur compounds, which react with iron and turn the can black. “Coating film” and “coating layer” are synonymous.
  • the coating composition of the present invention contains a polyester resin (A), a polyester resin (B), and a phenol resin (C).
  • a polyester resin (A) By including the polyester resin (A), the content contamination resistance of the coating film is improved.
  • the low temperature processability of a coating film, the adhesive force with a metal, and alkali resistance improve by including a polyester resin (B).
  • the polyester resin (A) is synthesized by reacting the polycarboxylic acid (a) and the polyol (b).
  • polycarboxylic acid (a) examples include aromatic dibasic acids, aliphatic dibasic acids, alicyclic dibasic acids and ⁇ , ⁇ -unsaturated dibasic acids, other dibasic acids and acid anhydrides thereof, These alkyl esters are also preferred.
  • the alkyl ester of the dibasic acid preferably has an alkyl group having 1 to 3 carbon atoms in terms of the synthesis reaction.
  • aromatic dibasic acid include terephthalic acid, isophthalic acid, orthophthalic acid, naphthalenedicarboxylic acid, and biphenyldicarboxylic acid.
  • Examples of the aliphatic dibasic acid include succinic acid, adipic acid, azelaic acid, sebacic acid, dodecanedioic acid, and dimer acid.
  • Examples of the alicyclic dibasic acid include 1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, and the like.
  • Examples of the ⁇ , ⁇ -unsaturated dibasic acid include fumaric acid, maleic acid, itaconic acid, citraconic acid and the like.
  • Examples of other dibasic acids include 2,5-norbornene dicarboxylic acid anhydride and tetrahydrophthalic anhydride.
  • the polycarboxylic acid (a) can be used alone or in combination of two or more.
  • the polyester resin (A) may have a branched structure as well as a linear structure.
  • a method in which a dibasic acid and a tri- or higher functional acid are used in combination is exemplified.
  • the trifunctional or higher functional acid is represented by, for example, (anhydrous) trimellitic acid [trimellitic acid and trimellitic anhydride together are referred to as “(anhydrous) trimellitic acid”. The same applies hereinafter. ], (Anhydrous) pyromellitic acid, ethylene glycol bis trimellitate dianhydride, etc. are mentioned.
  • the trifunctional or higher functional acid is preferably used in an amount of 0.1 to 10 mol% in 100 mol% of the synthesis of the polycarboxylic acid (a).
  • polycarboxylic acid (a) can be used in combination with a monobasic acid.
  • monobasic acid include benzoic acid.
  • an aliphatic diol having 2 to 10 carbon atoms, an alicyclic diol having 6 to 12 carbon atoms, a diol containing an ether bond, and other polyols are preferable.
  • Examples of the aliphatic diol having 2 to 10 carbon atoms include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, 1, Examples include 6-hexanediol, 3-methyl-1,5-pentanediol, 1,9-nonanediol, and 2-ethyl-2-butylpropanediol.
  • Examples of the alicyclic diol having 6 to 12 carbon atoms include 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol and the like.
  • Examples of the diol containing an ether bond include diethylene glycol, triethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, and polytetramethylene glycol.
  • Examples of other polyols include alicyclic polyalcohols such as tricyclodecane glycols and hydrogenated bisphenols.
  • Polyol (b) can be used alone or in combination of two or more.
  • a method of using a diol and a trifunctional or higher functional alcohol in combination is exemplified.
  • the tri- or higher functional alcohol include trimethylolpropane, glycerin, trimethylolethane, mannitol, sorbitol, pentaerythritol, and ⁇ -methylglucoside.
  • monoalcohol can be used in combination with the polyol (b).
  • Trifunctional or higher functional alcohol is preferably used in an amount of 0.1 to 10 mol% in 100 mol% of the synthesis of polycarboxylic acid (a).
  • the polyester resin (A) used in the present invention can be synthesized by a known reaction using a polycarboxylic acid (a) and a polyol (b).
  • the synthesis method can be synthesized by a condensation reaction or a transesterification reaction at a high temperature. It can also be synthesized by self-condensation of hydroxycarboxylic acid.
  • an acid anhydride is used for polycarboxylic acid (a)
  • an addition reaction also partially occurs. The end point of the reaction is usually determined by the acid value.
  • the glass transition temperature of the polyester resin (A) is 30 to 130 ° C, more preferably 45 to 85 ° C. When the glass transition temperature is within this range, a coating film that is excellent in resistance to content contamination and alkali resistance and whose workability is unlikely to deteriorate with time can be formed.
  • the number average molecular weight of the polyester resin (A) is preferably 5,000 to 30,000, more preferably 8,000 to 25,000. If the number average molecular weight is within this range, the processability and alkali resistance are further improved, and the solubility of the resin in the solvent can be further improved, so that the paintability of the coating composition is further improved.
  • the number average molecular weight in this invention is a value of standard polystyrene conversion by GPC (gel permeation chromatography).
  • the polyester resin (A) and the polyester resin (B) preferably have an acid value in order to improve the adhesion of the coating composition to the metal and the reactivity with the curing agent.
  • the acid value of the polyester resin (A) is 30 mgKOH / g or less, preferably 15 mgKOH / g or less. If the acid value is within this range, the content contamination resistance and alkali resistance are excellent, and in addition to forming a coating film whose workability is less likely to deteriorate with time, the acid resistance is also improved.
  • the lower limit of the acid value is 0 mgKOH / g.
  • the polyester resin (A) In order for the polyester resin (A) to have an acid value, it is preferable to use a polycarboxylic acid anhydride for the synthesis of the polyester resin (A), and the polycarboxylic acid anhydride is added after or during the polymerization reaction.
  • the acid value may be imparted by a method or the like.
  • the polycarboxylic acid anhydride include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, ethylene glycol bistrimellitic dianhydride, and the like.
  • polyester resin (A) Commercially available products of the polyester resin (A) include, for example, Byron 103, Byron 200, Byron 270, Byron 600, Byron GK360, Byron GK640, Byron GK880 manufactured by Toyobo Co., Ltd., Eliter UE3200, Eliter UE3201, Eriter UE3203, Unitika Eritre UE3500, Eritre UE3600, Eritre UE3660, Eritre UE9800, Eritre UE9900; EVONIK's Dynapole L205, Dynapole L206, Dynapole L208, Dynapole L912, Dynapole L952; and SK Chemical's Skybon ES100, Skybon ES250, Skybon ES410, Skybon ES660, Skybon ES901, Skybon ES955, etc. It is done.
  • the polyester resin (B) is a resin that is a reaction product of the polycarboxylic acid (a) and the polyol (b), like the polyester resin (A).
  • the glass transition temperature of the polyester resin (B) is less than ⁇ 20 ° C., and is adjusted by appropriately selecting the types of the polycarboxylic acid (a) and polyol (b) used as raw materials.
  • the polyester resin (B) used in the present invention is a resin that is a reaction product of the polycarboxylic acid (a) and the polyol (b).
  • 0 to 60 mol% of aromatic dibasic acid and 40 to 100 mol% of aliphatic dibasic acid are preferably contained.
  • ethylene glycol, 1,4-butanediol, neopentyl glycol, 3-methyl-1,5-pentanediol and 1,6-hexanediol in a total of 100 mol% of the polyol (b).
  • a coating film having excellent resistance to contamination of contents, alkali resistance and low temperature workability can be formed by combining with the above-described polyester resin (A) and phenol resin (C).
  • the compounds exemplified in the description of the polyester resin (A) can be used, and they can be synthesized by the same method.
  • the polyester resin (B) may have not only a linear structure but also a branched structure, like the polyester resin (A).
  • the method of branching is preferably the same method as the polyester resin (A).
  • the blending ratio of the polycarboxylic acid (a) and the polyol (b) in the polyester resin (A) and the polyester resin (B) is such that the hydroxyl group in the polyol (b) when the polycarboxylic acid (a) does not contain an esterified product.
  • NB / NA 1.10 to 2.40 is preferable, and 1.20 to 2.10 is more preferable.
  • the ratio of NB and NA is in the above range, the content contamination resistance and alkali resistance are further improved, and the workability is less likely to be lowered.
  • the esterified product of the polycarboxylic acid (a) include dimethyl terephthalic acid.
  • the total amount (molar ratio) exceeds 100 mol% because it indicates the actual mixing ratio.
  • the glass transition temperature of the polyester resin (B) is less than ⁇ 20 ° C., preferably ⁇ 60 to ⁇ 30 ° C., and more preferably ⁇ 50 to ⁇ 35 ° C. If the glass transition temperature is within this range, a coating film having excellent processability at low temperatures, adhesion to metals, retort resistance and alkali resistance can be obtained by combining with the polyester resin (A) and phenol resin (C) described above. Can be formed.
  • the number average molecular weight of the polyester resin (B) is preferably 5,000 to 100,000, and more preferably 10,000 to 90,000. If the number average molecular weight is within this range, the processability and alkali resistance are further improved, and the solubility of the resin in the solvent can be further improved.
  • the acid value of the polyester resin (B) is 30 mgKOH / g or less, preferably 15 mgKOH / g or less.
  • the acid value is within this range, in addition to being able to form a coating film that is excellent in resistance to content contamination and alkali resistance and hardly deteriorates in workability, acid resistance is also improved.
  • the acid value may be imparted by the same method as the polyester resin (A).
  • polyester resin (B) examples include Byron GM913, Byron GM920, Byron GM920, Byron GA6400, Byron 30P manufactured by Toyobo Co., Ltd .;
  • the polyester resin (A) and the polyester resin (B) are preferably blended so that the average glass transition temperature calculated by the following formula is 30 to 90 ° C, more preferably 35 to 80 ° C, More preferred is ⁇ 75 ° C.
  • the average glass transition temperature is within this range, it is possible to form a coating film that is particularly excellent in resistance to content contamination and alkali resistance and whose workability is unlikely to deteriorate with time.
  • Tg W (A) / Tg (A) + W (B) / Tg (B)
  • Tg is the average glass transition temperature (K) obtained
  • Tg (A) is the glass transition temperature (K) of the polyester resin (A)
  • Tg (B) is the glass transition temperature (K) of the polyester resin (B).
  • W (A) represents the weight ratio of the polyester resin (A)
  • W (B) represents the weight ratio of the polyester resin (B).
  • the phenol resin (C) used in the present invention is a curing agent for crosslinking the polyester resin.
  • the phenol resin is a resin synthesized by an addition condensation reaction between a phenol monomer and an aldehyde such as formaldehyde.
  • the phenol resin (C) can be synthesized by a known method.
  • phenol monomer examples include phenol, o-cresol, p-cresol, p-tert-butylphenol, p-phenylphenol, p-nonylphenol, 2,3-xylenol, 2,5-xylenol, m-cresol, 3,5 -Xylenol, resorcinol, bisphenol A, bisphenol F, bisphenol B, bisphenol E, bisphenol H, bisphenol S, catechol, hydroquinone and the like.
  • phenol, o-cresol, m-cresol, p-cresol and the like which are excellent in curability and reactivity, are preferable, and m-cresol is more preferable.
  • a phenol monomer may be used independently and may use 2 or more types together.
  • the ortho-position and the para-position serve as reaction sites with respect to the phenolic hydroxyl group. Therefore, o-cresol, p-cresol, p-tert-butylphenol, p-phenylphenol, p-nonylphenol, 2,3-xylenol, 2,5-xylenol, etc. have two reactive sites in one molecule. , A phenol monomer having an equivalent number of 2 and a functional group of 2. In addition, phenol, m-cresol, 3,5-xylenol, resorcinol, and the like have three reactive sites in one molecule, and thus are phenol monomers having an equivalent number of 3 and have a functional group of 3.
  • bisphenol such as bisphenol A, bisphenol F, bisphenol B, bisphenol E, bisphenol H, bisphenol S, catechol, hydroquinone, etc. are phenol monomers with 4 equivalents because there are 4 reactive sites in one molecule.
  • the functional group is 4.
  • a phenol monomer having an equivalent number of less than 4 it is easy to obtain a phenol resin having an appropriate molecular weight. Therefore, when such a phenol resin is used for a coating material, the solubility with respect to a solvent improves and it is hard to produce the aggregate derived from a phenol resin on the coating-film surface.
  • the phenol resin (C) is preferably a resin obtained by reacting m-cresol and an aldehyde. Since this phenol resin is excellent in curability with a polyester resin, retort resistance and alkali resistance are further improved.
  • the phenol resin (C) Commercially available products of the phenol resin (C) include, for example, Sumitrite Resin PR-55317 (metacresol phenol resin, nonvolatile concentration 50% by weight) manufactured by Sumitomo Bakelite Co., Ltd. Shounol CKS-3898 (metacresol system manufactured by Showa Denko KK). Phenol resin, nonvolatile content concentration of 50% by weight) and the like.
  • the metacresol-based resin is a resin obtained by using m-cresol as a raw material for the phenol resin (C).
  • the coating composition of the present invention can be blended with a lubricant such as wax, an additive such as a curing catalyst, a leveling agent and a plasticizer, and an organic solvent as needed.
  • a lubricant such as wax
  • an additive such as a curing catalyst, a leveling agent and a plasticizer
  • an organic solvent such as water
  • the waxes are animal and plant waxes such as carnauba wax, lanolin wax, palm oil, candelilla wax and rice wax; petroleum waxes such as paraffin wax, microcrystalline wax and petrolatum; Examples thereof include synthetic waxes such as polyolefin wax and Teflon (registered trademark) wax.
  • the curing catalyst include dodecylbenzenesulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, dinonylnaphthalenedisulfonic acid, trifluoromethanesulfonic acid, sulfuric acid, and phosphoric acid compounds, and neutralized products thereof.
  • the coating composition of the present invention can be used regardless of the inner and outer surfaces of the can, and is preferably used as an inner coating of the can by taking advantage of its high workability, and particularly used for the inner surface coating of can lid members. It is preferable to do.
  • the can lid of the present invention can be obtained by providing a coating layer, which is a cured product of the coating composition of the present invention, on at least one surface of a metal or plastic member.
  • the thickness of the coating layer is about 1 to 100 ⁇ m.
  • the thickness of the member is about 0.05 to 5 mm.
  • the coating composition of the present invention has good adhesion to plastic films in addition to the above properties, it is also preferably used as an adhesive for laminating plastic films and metals in film laminated metal cans. it can.
  • the thickness of the adhesive layer is 0.01 to 10 ⁇ m.
  • the can for food and drink of the present invention includes a can lid and a can body member.
  • Food and beverage cans are cans including beverage cans and food cans, and can contain beverages or foods other than beverages as contents. And it is preferable to provide the can lid
  • a can for food and drink forms a coating layer by coating a can coating material on the inner surface or outer surface of a metal or plastic can body, and further on a film-laminated metal can and curing it.
  • an adhesive layer formed when used as an adhesive for bonding a plastic film and a metal in a film-laminated metal can is also included in the category of the coating layer.
  • the metal is preferably a metal plate such as aluminum, tin-plated steel plate, chrome-treated steel plate, or nickel-treated steel plate.
  • the plastic is preferably polyolefin, polyester or the like.
  • polyester, particularly PET (polyethylene terephthalate) is preferable.
  • spray coating such as air spray, airless spray, and electrostatic spray, roll coater coating, immersion coating, and electrodeposition coating can be used.
  • the coating composition When the coating composition is applied to metal, it is preferably baked at a temperature of 200 to 300 ° C. for 10 seconds to 2 minutes, more preferably 20 to 40 seconds.
  • the food and beverage can of the present invention comprises the can lid and can body member of the present invention.
  • the can for food and drink is preferably a two-piece can constituted by one can lid and one can body member, and a three-piece can constituted by two upper and lower can lids and one can body member.
  • the beverage is preferably drinking water, soft drink, coffee, tea, beer, Chuhai, sake, whiskey, water split, and the like.
  • foods other than beverages are preferably used for storing foods such as fish meat, livestock meat, vegetables, fruits, oils, and sauces.
  • the can provided with a coating film using the coating composition of the present invention can be used for storing non-food such as engine oil, paint and ink.
  • parts represents “parts by weight” and “%” represents “% by weight” unless otherwise specified.
  • Mn represents the number average molecular weight
  • Mw represents the weight average molecular weight.
  • the measurement was performed using a high-speed GPC device 8020 series (tetrahydrofuran solvent, column temperature 40 ° C., polystyrene standard) manufactured by Tosoh Corporation. Specifically, it is a measured value obtained by connecting four columns of G1000HXL, G2000HXL, G3000HXL, and G4000HXL manufactured by Tosoh in series and measuring at a flow rate of 1.0 ml / min.
  • GPC device 8020 series tetrahydrofuran solvent, column temperature 40 ° C., polystyrene standard
  • Polyester Resin (A) [Production Example (A) -1 (Direct Polymerization Method)] 86.3 parts terephthalic acid, 201.3 parts isophthalic acid, 21.5 parts ethylene glycol, 101.3 parts 2-methyl-1,3-propanediol, 87.3 parts 1,4-cyclohexanedimethanol, trimethylol
  • the polymerization reactor was charged with 2.3 parts of propane and 0.01 part of titanium butoxide, and the temperature was gradually raised to 250 ° C. in a nitrogen atmosphere, and an esterification reaction was performed over 6 hours. Next, the pressure was reduced to 5 mmHg or less over 30 minutes, and a polymerization reaction was performed for 2 hours in that state. Thereafter, the resin was cooled to 200 ° C.
  • the polyester resin of the present invention was obtained.
  • polymerization is described in Table 1 as molar ratio. Other production examples are also expressed in molar ratios in Tables 1 and 2 as described above.
  • the polyester resin of the present invention was obtained.
  • Polyester Resin (B) [Production Example (B) -1 (Direct Polymerization Method)] 54.9 parts of terephthalic acid, 54.9 parts of isophthalic acid, 200.4 parts of sebacic acid, 23.6 parts of ethylene glycol, 111.6 parts of 1,4-butanediol, 52.4 parts of 1,4-cyclohexanedimethanol Then, 2.2 parts of trimethylolpropane and 0.01 part of titanium butoxide were charged into a polymerization reactor, and the temperature was gradually raised to 250 ° C. in a nitrogen atmosphere, and an esterification reaction was performed over 4 hours.
  • Example 1 435.1 parts of polyester resin varnish of Production Example (A) -1; 48.3 parts of polyester resin varnish of Production Example (B) -1; Sumilite Resin PR-55317 (metacresol phenol resin, non-volatile content as phenol resin) 43.1 parts of 50% n-butanol solution (manufactured by Sumitomo Bakelite), 153.4 parts of Flexisolv DBE esters (manufactured by Invista), 191.1 parts of xylene, 23.6 parts of butyl cellosolve, 28 of n-butanol 0.4 part and 76.8 parts of cyclohexanone were mixed, and 0.4 part of dodecylbenzenesulfonic acid was added as a curing catalyst to obtain a paint having a nonvolatile content of 21.5%.
  • Sumilite Resin PR-55317 metalacresol phenol resin, non-volatile content as phenol resin
  • 43.1 parts of 50% n-butanol solution manufactured by Sumito
  • Example 2 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -2 and 48.3 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 3 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -3 and 48.3 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 4 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -4 and 48.3 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 5 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -5 and 48.3 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 6 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Production Example (B) -2 were used.
  • Example 7 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Production Example (B) -3 were used.
  • Example 8 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Production Example (B) -4 were used.
  • Example 9 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Production Example (B) -5 were used.
  • Example 10 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Production Example (B) -6 were used.
  • Example 11 A coating material was obtained in the same manner as in Example 1 except that 386.7 parts of the polyester resin varnish of Production Example (A) -1 and 96.7 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 12 A coating material was obtained in the same manner as in Example 1 except that 338.4 parts of the polyester resin varnish of Production Example (A) -1 and 145.0 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 13 A coating material was obtained in the same manner as in Example 1 except that 290.0 parts of the polyester resin varnish of Production Example (A) -1 and 193.4 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 14 A coating material was obtained in the same manner as in Example 1 except that 241.7 parts of the polyester resin varnish of Production Example (A) -1 and 241.7 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 15 A coating material was obtained in the same manner as in Example 1 except that 386.7 parts of the polyester resin varnish of Production Example (A) -1 and 96.7 parts of the polyester resin varnish of Production Example (B) -2 were used.
  • Example 16 A coating material was obtained in the same manner as in Example 1 except that 338.4 parts of the polyester resin varnish of Production Example (A) -1 and 145.0 parts of the polyester resin varnish of Production Example (B) -2 were used.
  • Example 17 A coating material was obtained in the same manner as in Example 1 except that 386.7 parts of the polyester resin varnish of Production Example (A) -1 and 96.7 parts of the polyester resin varnish of Production Example (B) -3 were used.
  • Example 18 A coating material was obtained in the same manner as in Example 1 except that 386.7 parts of the polyester resin varnish of Production Example (A) -2 and 96.7 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 19 A coating material was obtained in the same manner as in Example 1 except that 386.7 parts of the polyester resin varnish of Production Example (A) -3 and 96.7 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 20 A coating material was obtained in the same manner as in Example 1 except that 338.4 parts of the polyester resin varnish of Production Example (A) -3 and 145.0 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 21 A coating material was obtained in the same manner as in Example 1 except that 241.7 parts of the polyester resin varnish of Production Example (A) -3 and 241.7 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 22 A coating material was obtained in the same manner as in Example 1 except that 193.4 parts of the polyester resin varnish of Production Example (A) -3 and 290.0 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 23 386.8 parts of polyester resin varnish of Production Example (A) -1; 43.0 parts of polyester resin varnish of Production Example (B) -1; Sumilite Resin PR-55317 (metacresol phenolic resin, 50% nonvolatile content)
  • a coating material was obtained in the same manner as in Example 1 except that 86.0 parts of n-butanol solution (manufactured by Sumitomo Bakelite Co., Ltd.) and 201.8 parts of xylene were used.
  • Example 24 449.7 parts of polyester resin varnish of Production Example (A) -1; 50.0 parts of polyester resin varnish of Production Example (B) -1; Sumilite Resin PR-55317 (metacresol phenolic resin, 50% nonvolatile content) A coating material was obtained in the same manner as in Example 1 except that 30.1 parts of n-butanol solution (manufactured by Sumitomo Bakelite Co., Ltd.) and 187.8 parts of xylene were used.
  • Example 1 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Comparative Production Example (A) -6 and 48.3 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 2 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Comparative Production Example (A) -7 and 48.3 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 3 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Comparative Production Example (A) -8 and 48.3 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 4 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Comparative Production Example (B) -7 were used.
  • Example 5 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Comparative Production Example (B) -8 were used.
  • Example 6 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Comparative Production Example (B) -9 were used.
  • Example 7 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Comparative Production Example (B) -10 were used.
  • Example 8 A coating material was obtained in the same manner as in Example 1 except that 435.1 parts of the polyester resin varnish of Production Example (A) -1 and 48.3 parts of the polyester resin varnish of Comparative Production Example (B) -11 were used.
  • Example 9 A coating material was obtained in the same manner as in Example 1 except that 386.7 parts of the polyester resin varnish of Production Example (A) -6 and 96.7 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 10 A coating material was obtained in the same manner as in Example 1 except that 338.4 parts of the polyester resin varnish of Production Example (A) -6 and 145.0 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 11 A coating material was obtained in the same manner as in Example 1 except that 386.7 parts of the polyester resin varnish of Production Example (A) -8 and 96.7 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 12 A coating material was obtained in the same manner as in Example 1 except that 338.4 parts of the polyester resin varnish of Production Example (A) -8 and 145.0 parts of the polyester resin varnish of Production Example (B) -1 were used.
  • Example 13 A coating material was obtained in the same manner as in Example 1 except that 386.7 parts of the polyester resin varnish of Production Example (A) -1 and 96.7 parts of the polyester resin varnish of Production Example (B) -7 were used.
  • Example 14 A coating material was obtained in the same manner as in Example 1 except that 338.4 parts of the polyester resin varnish of Production Example (A) -1 and 145.0 parts of the polyester resin varnish of Production Example (B) -7 were used.
  • Example 15 A coating material was obtained in the same manner as in Example 1 except that 290.0 parts of the polyester resin varnish of Production Example (A) -1 and 193.4 parts of the polyester resin varnish of Production Example (B) -7 were used.
  • Example 16 A coating material was obtained in the same manner as in Example 1 except that 483.4 parts of the polyester resin varnish of Production Example (A) -1 was used and the polyester resin (B) was not used.
  • Example 17 A coating material was obtained in the same manner as in Example 1 except that 483.4 parts of the polyester resin varnish of Production Example (A) -2 was used and the polyester resin (B) was not used.
  • Example 18 A coating material was obtained in the same manner as in Example 1 except that 483.4 parts of the polyester resin varnish of Production Example (A) -3 was used and the polyester resin (B) was not used.
  • Example 19 A coating material was obtained in the same manner as in Example 1 except that 483.4 parts of the polyester resin varnish of Production Example (B) -1 was used and the polyester resin (A) was not used.
  • Example 20 A coating material was obtained in the same manner as in Example 1 except that 483.4 parts of the polyester resin varnish of Production Example (B) -2 was used and the polyester resin (A) was not used.
  • Example 21 A coating material was obtained in the same manner as in Example 1 except that 483.4 parts of the polyester resin varnish of Production Example (B) -3 was used and the polyester resin (A) was not used.
  • test panel The paints obtained in Examples 1 to 24 and Comparative Examples 1 to 24 were coated on a 0.26 mm thick aluminum plate with a bar coater so that the dry weight was 80 mg / dm 2 .
  • a test panel provided with a coating film was produced by passing through a double-type conveyor oven having a temperature of 286 ° C. and a temperature of the second zone of 326 ° C. in 24 seconds, followed by drying and curing. The obtained test panel was evaluated as follows.
  • the test panel was prepared in a size of 30 mm in width and 50 mm in length.
  • a round bar 2 having a diameter of 3 mm is attached to a position having a longitudinal length of 30 mm with the coating film of the test panel 1 on the outside as shown in FIG. And then.
  • the test panel 2 was folded in two along the round bar 2 to prepare a test piece 3. Two pieces of 0.26 mm thick aluminum plates (omitted) are sandwiched between the test pieces 3 folded in half, and as shown in FIG. 1 (c), a rectangular solid 1 kg of 15 cm in width, 5 cm in height and 5 cm in depth.
  • the weight 4 was dropped from a height of 40 cm onto the bent portion of the test piece 3 and completely bent.
  • the bent portion of the test piece 3 was immersed in a saline solution having a concentration of 1%.
  • a current was measured for 6.0 V ⁇ 6 seconds.
  • a coated plate similar to that used for evaluation of “bending workability” was cut into a size of 30 mm ⁇ 50 mm (length ⁇ width). Next, it is immersed in water at a water temperature of 4 ° C., and after 1 hour, with the coating film facing outward in water, bent by hand so that the width of 50 mm is 20 mm and 30 mm, and then the bending tip of the test piece The part was immersed in a 1% strength saline solution, and the current value was measured after applying electricity 10 times at 6.0 V for 6 seconds between the metal part of the test piece not immersed in the saline solution and the saline solution.
  • a test panel was prepared in a size of 50 mm long ⁇ 50 mm wide.
  • a mold was formed into a shape of a general steion tab opening with a beverage can on the painted surface of the test panel, and used as a sample.
  • the aluminum plate was peeled off along the shape of the opening from the uncoated surface side of the sample, and the opening was magnified with a microscope and visually judged.
  • the opening property is poor, the coating film tends to remain in the peripheral part of the opening, and the width of the film protruding into the opening becomes large.
  • “Openness is good” means that the coating film does not protrude into the opening at all, or even if it protrudes, its protruding width is very small.
  • the width of the protruding coating film was measured and evaluated according to the following evaluation criteria.
  • Corrosion resistance was evaluated by acid resistance test and alkali resistance test.
  • ⁇ Very thin whitening (can be used)
  • ⁇ Slightly whitened (cannot be used)
  • ⁇ Remarkably whitened (defect)
  • ⁇ Content contamination test> A test panel was placed in a retort kettle and immersed in water. Next, a retort treatment was performed at 125 ° C. for 30 minutes. The ratio of the area of the test panel (that is, the area of the coating film) and water was such that water was 100 mL with respect to 100 cm 2 of the test panel. The water after the retort treatment was analyzed using “TOC-L CPH” (manufactured by Shimadzu Corporation), and the total amount of organic carbon (TOC) was measured. In addition, the amount of TOC is the total amount of organic matter present in water expressed as the amount of carbon in the organic matter.
  • ⁇ Aging processability test> The test panel was left in a 37 ° C. constant temperature bath for 60 days, and then the panel was processed in the same manner as in the bending workability test, and the current value was measured. Next, the difference between the current value obtained in the bending workability test and the current value after aging of the panel (current value after aging of the panel ⁇ current value before aging of the panel) was determined to evaluate the workability with time.
  • X 10 mA or more (defect)
  • Tables 3 and 4 show the physical property evaluation results of each coating composition.
  • a polyester resin shows the compounding ratio of a polyester resin (A) and a polyester resin (B) by weight ratio.
  • the coating material has shown the compounding part of the polyester resin and the compounding part of a phenol resin contained in a total of 100 weight part of a polyester resin and a phenol resin.
  • Test panel 2 Round bar 3 Test piece 4 Weight

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)
  • Laminated Bodies (AREA)
  • Details Of Rigid Or Semi-Rigid Containers (AREA)

Abstract

L'objet de la présente invention est de produire une composition de revêtement permettant de former des films de revêtement qui sont excellents en termes d'aptitude au traitement à basse température, de résistance aux alcalis et d'adhérence sur des métaux. La composition de revêtement comprend une résine polyester (A) ayant un indice d'acide inférieur ou égal à 30 mg-KOH/g et une température de transition vitreuse comprise entre 30 et 110 °C, une résine polyester (B) ayant un indice d'acide inférieur ou égal à 30 mg-KOH/g et une température de transition vitreuse inférieure à -20 °C, et une résine phénolique (C). La résine de polyester (B) est obtenue par réaction d'un acide polycarboxylique (a) avec un polyol (b).
PCT/JP2017/026501 2016-08-01 2017-07-21 Composition de revêtement Ceased WO2018025669A1 (fr)

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JP7117709B2 (ja) * 2017-12-14 2022-08-15 ユニチカ株式会社 ポリエステル樹脂および塗料用樹脂組成物
JP7730676B2 (ja) * 2021-06-28 2025-08-28 旭化成株式会社 金属顔料組成物の梱包体
JP7680286B2 (ja) * 2021-06-28 2025-05-20 旭化成株式会社 金属顔料組成物の梱包体

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JP2009221316A (ja) * 2008-03-14 2009-10-01 Unitika Ltd ポリエステル樹脂水性分散体、それから得られる被膜、および該被膜を利用した包装袋
WO2013111814A1 (fr) * 2012-01-27 2013-08-01 Dic株式会社 Composition de revêtement, revêtement pour boîte de conserve la contenant et matériau métallique de revêtement de surface interne revêtu par ledit revêtement
JP2013249376A (ja) * 2012-05-31 2013-12-12 Toyo Seikan Co Ltd 塗料組成物及びこの塗料組成物を塗布して成る塗装金属板、金属容器及び金属蓋
WO2016125445A1 (fr) * 2015-02-06 2016-08-11 東洋インキＳｃホールディングス株式会社 Composition de matériau de revêtement, couvercle de boîte et boîte pour aliments et boissons

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JP2006037014A (ja) * 2004-07-29 2006-02-09 Nippon Ester Co Ltd 塗料用組成物
JP2009221316A (ja) * 2008-03-14 2009-10-01 Unitika Ltd ポリエステル樹脂水性分散体、それから得られる被膜、および該被膜を利用した包装袋
WO2013111814A1 (fr) * 2012-01-27 2013-08-01 Dic株式会社 Composition de revêtement, revêtement pour boîte de conserve la contenant et matériau métallique de revêtement de surface interne revêtu par ledit revêtement
JP2013249376A (ja) * 2012-05-31 2013-12-12 Toyo Seikan Co Ltd 塗料組成物及びこの塗料組成物を塗布して成る塗装金属板、金属容器及び金属蓋
WO2016125445A1 (fr) * 2015-02-06 2016-08-11 東洋インキＳｃホールディングス株式会社 Composition de matériau de revêtement, couvercle de boîte et boîte pour aliments et boissons

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US20230287173A1 (en) * 2020-07-01 2023-09-14 Ppg Industries Ohio, Inc. Methods of preparing coated substrates and non-aqueous, curable film-forming compositions used therefor
US12415887B2 (en) * 2020-07-01 2025-09-16 Ppg Industries Ohio, Inc. Methods of preparing coated substrates and non-aqueous, curable film-forming compositions used therefor

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