WO2021157726A1 - 基材接着性良好なポリウレタン樹脂、及びこれを用いた接着剤、インキバインダーまたはコーティング剤用組成物 - Google Patents
基材接着性良好なポリウレタン樹脂、及びこれを用いた接着剤、インキバインダーまたはコーティング剤用組成物 Download PDFInfo
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- WO2021157726A1 WO2021157726A1 PCT/JP2021/004434 JP2021004434W WO2021157726A1 WO 2021157726 A1 WO2021157726 A1 WO 2021157726A1 JP 2021004434 W JP2021004434 W JP 2021004434W WO 2021157726 A1 WO2021157726 A1 WO 2021157726A1
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- Prior art keywords
- polyurethane resin
- mass
- diisocyanate
- parts
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- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 52
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 239000000853 adhesive Substances 0.000 title claims abstract description 24
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 24
- 239000011248 coating agent Substances 0.000 title claims abstract description 17
- 239000011230 binding agent Substances 0.000 title claims abstract description 16
- 239000000463 material Substances 0.000 title abstract description 10
- 238000000576 coating method Methods 0.000 title abstract description 6
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- 229920005862 polyol Polymers 0.000 claims abstract description 31
- 150000003077 polyols Chemical class 0.000 claims abstract description 28
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 26
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 14
- 239000004970 Chain extender Substances 0.000 claims abstract description 13
- 230000009477 glass transition Effects 0.000 claims abstract description 7
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
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- 150000002009 diols Chemical class 0.000 description 16
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
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- 125000003118 aryl group Chemical group 0.000 description 4
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- 150000002739 metals Chemical class 0.000 description 4
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- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
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- 229920001342 Bakelite® Polymers 0.000 description 2
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
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- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2150/00—Compositions for coatings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2170/00—Compositions for adhesives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2475/00—Presence of polyurethane
Definitions
- the present invention relates to a polyurethane resin having good adhesiveness to various substrates using a polycarbonate diol having a specific skeleton and an organic diisocyanate, and a composition for a film adhesive, an ink binder or a coating agent using the resin.
- polyurethane resin is widely used as an adhesive to a base material such as a polyethylene terephthalate film or a polycarbonate film. This is because it is possible to design a wide range of physical properties, forms, and curing modes, and it is also excellent in chemical properties such as chemical resistance (Patent Document 1).
- the above-mentioned adhesive contains a large amount of linear aliphatic skeleton in its constituents to soften the membrane and improve the reactivity.
- due to its flexibility, heat load, hot water treatment, etc. As a result, there are problems of deterioration of adhesion and surface hardness due to outflow and decomposition.
- the base materials that exhibit adhesion are limited, and base material selectivity has become an issue.
- the present invention has been made to solve the above problems of the prior art. That is, the present invention relates to a composition for a film adhesive, an ink binder or a coating agent using a polyurethane resin having excellent heat resistance, surface hardness and good adhesiveness to various substrates.
- the present inventors have found that a composition using a polyurethane resin containing a polycarbonate diol having a specific skeleton as a main raw material is excellent in adhesiveness to various substrates, heat resistance, and surface hardness. This led to the present invention. That is, the present invention has the following configuration.
- the polyurethane resin (X) containing a polycarbonate polyol (A), an organic diisocyanate (B) and a chain extender (C), and a cross-linking agent (Y) are contained as copolymerization components, and the glass transition temperature of the polyurethane resin (X). Is 50 ° C. or higher, 60 mol% or more of the structure represented by the following general formula (1) is contained in the polycarbonate polyol (A), and the cross-linking agent (Y) is added to 100 parts by mass of the polyurethane resin (X).
- the organic diisocyanate (B) is preferably isophorone diisocyanate, 4,4'-diphenylmethane diisocyanate or hexamethylene diisocyanate, and the chain extender (C) is preferably a glycol compound having 7 or less carbon atoms.
- composition containing the polyurethane resin (X) of the present invention is excellent in adhesiveness to various substrates, heat resistance, outflow property, and surface hardness. Therefore, it is suitable for applications such as film adhesives, screen inks, ink binders for decorative molding, and coating agents for surface protection.
- the polyurethane resin (X) of the present invention contains a polycarbonate polyol (A), an organic diisocyanate (B), and a chain extender (C) as copolymerization components.
- the polycarbonate polyol (A) used in the present invention needs to include a structure represented by the following general formula (1).
- the polycarbonate polyol (A) used in the present invention needs to include a structure represented by the following general formula (1).
- the total content of the polycarbonate polyol (A) is 100 mol%, it is necessary to contain 60 mol% or more of the structure represented by the general formula (1), preferably 70 mol% or more, and more. It is preferably 80 mol% or more, more preferably 90 mol% or more, particularly preferably 95 mol% or more, and may be 100 mol% or more.
- flexibility can be imparted to the polyurethane resin (X), and excellent adhesiveness, heat resistance, and surface hardness can be exhibited.
- n represents an integer of 1 to 20.
- N is preferably 2 or more, more preferably 3 or more, and even more preferably 5 or more. Further, it is preferably 18 or less, more preferably 15 or less, and further preferably 10 or less. Within the above range, the cohesive force of the obtained polyurethane resin (X) is improved, and excellent adhesiveness and heat resistance can be exhibited.
- polycarbonate polyol (A) other than the polycarbonate polyol having the structure represented by the general formula (1) an aliphatic polycarbonate polyol, an alicyclic polycarbonate or an aromatic polycarbonate polyol can be used.
- these polycarbonate polyols are preferably 40 mol% or less, more preferably 30 mol% or less, still more preferably 20 mol% or less, and even more. It is preferably 10 mol% or less, particularly preferably 5 mol% or less, and may be 0 mol% or less.
- the aliphatic polycarbonate polyol is not particularly limited, and linear or branched aliphatic glycols such as butanediol, pentanediol, hexanediol, polycaprolactone, polytetramethylene glycol, propylene glycol, and neopentyl glycol and carbonate diesters and the like are used. Polycarbonate diol obtained by the reaction can be used.
- the alicyclic polycarbonate polyol is not particularly limited, and a polycarbonate diol obtained by reacting an alicyclic glycol such as isosorbide with a carbonic acid diester or the like can be used.
- the aromatic polycarbonate diol is not particularly limited, and a polycarbonate diol obtained by reacting an aromatic glycol such as benzenedimethanol or naphthalenedimethanol with a carbonic acid diester can be used. Polycarbonate diols made of one of the above glycols or a combination thereof can be used.
- the number average molecular weight of the polycarbonate polyol (A) is preferably 300 to 2,500, more preferably 500 to 1,500.
- the number average molecular weight of the polycarbonate diol (A) was calculated by the following formula.
- Number average molecular weight (56.1 x 1000 x valence) / hydroxyl value [mgKOH / g]
- the valence is the number of hydroxyl groups in one molecule, and [mgKOH / g] is a unit of hydroxyl valence.
- Organic diisocyanate (B) used in the present invention is tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), 2-methyl-1,5-pentane diisocyanate, decamethylene diisocyanate, 3-methyl-1,5-pentane diisocyanate, lysine.
- Alibo diisocyanates such as diisocyanates; alicyclic diisocyanates such as isophorone diisocyanates (IPDI), hydrogenated tolylene diisocyanates, hydrogenated diphenylmethane diisocyanates, hydrogenated xylylene diisocyanates, hydrogenated tetramethylxylylene diisocyanates, cyclohexyl diisocyanates; 2,4 -Torylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate (MDI), 2,4'-diphenylmethane diisocyanate, 2,2'-diphenylmethane diisocyanate, 1,5-naphthylene diisocyanate, 1, 4-naphthylene diisocyanate, o-phenylenediocyanate, p-phenylenediocyanate, m-phenylenedi isocyan
- a mixture containing two or more of the organic diisocyanates, urethane modified products of these organic diisocyanates, allophanate modified products, urea modified products, biuret modified products, uretdione modified products, uretoimine modified products, isocyanurate modified products, carbodiimide modified products, etc. can be mentioned.
- Hexamethylene diisocyanate, isophorone diisocyanate, and 4,4'-diphenylmethane diisocyanate are preferable as the organic diisocyanate in the present invention, and the obtained polyurethane resin (X) has good solvent solubility and may cause gelation during production.
- Isophorone diisocyanate which is small in size and has excellent weather resistance and mechanical strength of the resin, is particularly preferable.
- the copolymerization amount of the organic diisocyanate (B) is preferably 1 part by mass or more, more preferably 2 parts by mass or more, and further preferably 5 parts by mass or more with respect to 100 parts by mass of the polycarbonate polyol (A). It is particularly preferably 10 parts by mass or more. Further, it is preferably 60 parts by mass or less, more preferably 50 parts by mass or less, further preferably 45 parts by mass or less, and particularly preferably 40 parts by mass or less. Within the above range, a polyurethane resin (X) having excellent adhesiveness, heat resistance, and surface hardness can be obtained.
- the chain extender (C) used in the present invention is not particularly limited as long as it extends the molecular chain of the polyurethane resin (X), and preferably has a group that reacts with the organic diisocyanate (B).
- the chain extender (C) is not particularly limited, but is preferably a polyol compound, more preferably a glycol compound, from the viewpoint of gelation and reactivity during production.
- the glycol compound may be any of an aliphatic glycol compound, an aromatic glycol compound or an alicyclic glycol compound, but an aliphatic glycol compound is preferable.
- a linear or branched aliphatic glycol compound having 10 or less carbon atoms is preferable, and a linear or branched aliphatic glycol compound having 7 or less carbon atoms is more preferable.
- ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol examples thereof include 1,6-hexanediol, 3-methyl-1,5-pentanediol, neopentyl glycol, 2-ethyl-4-butyl-1,3-propanediol, diethylene glycol, dipropylene glycol, neopentyl glycol and the like. .. In the present invention, neopentyl glycol or 1,6-hexanediol is preferable from the viewpoint of re
- the copolymerization amount of the chain extender (C) is preferably 1 part by mass or more, more preferably 2 parts by mass or more, and further preferably 3 parts by mass with respect to 100 parts by mass of the polycarbonate polyol (A).
- the above is more preferably 4 parts by mass or more. Further, it is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, further preferably 10 parts by mass or less, and particularly preferably 8 parts by mass or less.
- a polyurethane resin (X) having excellent adhesiveness, heat resistance, and surface hardness can be obtained.
- the glass transition temperature of the polyurethane resin (X) of the present invention needs to be 50 ° C. or higher. It is preferably 55 ° C. or higher, and more preferably 60 ° C. or higher. By setting the value to the lower limit or more, it is possible to suppress a decrease in adhesiveness to the base material due to a heat load and suppress the occurrence of outflow. Further, it is preferably 120 ° C. or lower. It is more preferably 110 ° C. or lower, further preferably 100 ° C. or lower, and particularly preferably 95 ° C. or lower. By setting the value to the upper limit or less, it is possible to suppress a decrease in adhesiveness to the base material.
- the number average molecular weight of the polyurethane resin (X) of the present invention is preferably 5,000 to 50,000, more preferably 8,000 to 30,000, and even more preferably 12,000 to 22,000. be.
- the number average molecular weight is preferably 5,000 to 50,000, more preferably 8,000 to 30,000, and even more preferably 12,000 to 22,000. be.
- the total amount of the polycarbonate polyol (A), the organic diisocyanate (B) and the chain extender (C) is preferably 80% by mass or more, more preferably 90% by mass. % Or more, more preferably 95% by mass, particularly preferably 99% by mass or more, and 100% by mass may be used. Within the above range, excellent adhesiveness, heat resistance, and surface hardness can be exhibited.
- a polycarbonate diol (A) having a specific skeleton, an organic diisocyanate (B), and a chain extender (C) may be collectively charged into a reaction vessel. It may be divided and prepared. The total hydroxyl value of the polycarbonate diol (A) and the chain extender (C) in the system and the total isocyanate group of the organic diisocyanate (B) are reacted when the ratio of the functional group of the isocyanate group / hydroxyl group is 1 or less. Is preferable. It is more preferably 0.99 or less, still more preferably 0.98 or less.
- this reaction can be stably produced by reacting in the presence or absence of a solvent that is inert to the isocyanate group.
- the solvent is not particularly limited, but is an ester solvent (ethyl acetate, butyl acetate, ethyl butyrate, etc.), an ether solvent (dioxane, tetrahydrofuran, diethyl ether, etc.), a ketone solvent (cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone, etc.). ), Aromatic hydrocarbon solvents (benzene, toluene, xylene, etc.) and mixed solvents thereof.
- the reaction device not only a reaction can equipped with a stirrer but also a mixing and kneading device such as a kneader and a twin-screw extruder can be used.
- a catalyst used in a normal urethanization reaction can be used.
- catalysts include tin-based catalysts (trimethyltin laurate, dimethyltin dilaurate, trimethyltin hydroxide, dimethyltin dihydroxide, stanas octoate, etc.), bismuth-based catalysts, and lead-based catalysts (red oleate, red-2-). Ethylhexoate, etc.)
- Amine-based catalysts triethylamine, tributylamine, morpholine, diazabicyclooctane, etc.
- These catalysts may be used alone or in combination of two or more.
- the cross-linking agent (Y) used in the present invention is not particularly limited as long as it reacts with the polyurethane resin (X) to cross-link. It is preferably a compound having two or more functional groups in one molecule, and examples of the functional group include an isocyanate group, an epoxy group, an amino group, a methylol group, an alkoxymethyl group, an imino group, a metal chelating group, and an aziridinyl group. Can be mentioned. Specific examples of the compound include a polyfunctional isocyanate compound, a polyfunctional epoxy compound, a polyfunctional melamine compound, a metal cross-linking agent, and a polyfunctional aziridine compound.
- the polyfunctional isocyanate compound is a compound having two or more isocyanate groups per molecule.
- Specific examples include tolylene diisocyanate (TDI), 4,4'-diphenylmethane diisocyanate (MDI), hexamethylene diisocyanate, orthoxylylene diisocyanate, metaxylylene diisocyanate, paraxylylene diisocyanate, 1,5-naphthalenedisocyanate, 1 , 4-Naphthalenediocyanate, 1,8-naphthalenediocyanate, hydride diphenylmethane diisocyanate, hydrogenated tolylene diisocyanate, hydride xylylene diisocyanate, isophorone diisocyanate and other diisocyanate compounds, and polyisocyanate compounds composed of these are examples of organic diisocyanates.
- Examples thereof include urethane modified products, allophanate modified products, urea modified products, biuret modified products, uretdione modified products, uretoimine modified products, isocyanurate modified products, and carbodiimide modified products. These may be used alone or in combination of two or more.
- a polyfunctional epoxy compound is a compound having two or more epoxy groups per molecule.
- Specific examples include diglycidyl ethers of aliphatic diols such as 1,6-hexanediol, neopentyl glycol and polyalkylene glycol, sorbitol, sorbitan, polyglycerol, pentaerythritol, diglycerol, glycerol, trimethylolpropane and the like.
- Aliphatic polyol polyglycidyl ether such as cyclohexanedimethanol, terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, trimellitic acid, adipic acid, sebacic acid and other aliphatic or aromatic Diglycidyl ester or polyglycidyl ester of polyvalent carboxylic acid can be mentioned.
- resorcinol bis- (p-hydroxyphenyl) methane, 2,2-bis- (p-hydroxyphenyl) propane, tris- (p-hydroxyphenyl) methane, 1,1,2,2-tetrakis (p-).
- Metal cross-linking agents include metals such as aluminum, zinc, cadmium, nickel, cobalt, copper, calcium, barium, titanium, manganese, iron, lead, zirconium, chromium and tin, as well as acetylacetone, methyl acetoacetate and ethyl acetoacetate. Examples thereof include metal chelate compounds coordinated with ethyl lactate, methyl salicylate and the like. These may be used alone, or two or more kinds may be used in combination.
- a polyfunctional aziridine compound is a compound having two or more aziridine groups per molecule.
- Specific examples include N, N'-hexamethylene-1,6-bis (1-aziridinecarboxamide), trimethylpropan-tri- ⁇ -aziridinyl propionate, and bisisophthaloyl-1- (2).
- -Methylaziridine tri-1-aziridinylphosphonoxide, N, N'-diphenylethane-4,4'-bis (1-aziridinecarboxamide) and the like. These may be used alone, or two or more kinds may be used in combination.
- the cross-linking agent (Y) is preferably a polyfunctional isocyanate compound. More preferably, it is xylylene diisocyanate or a modified product thereof.
- the content of the cross-linking agent (Y) needs to be 1 part by mass or more, preferably 2 parts by mass or more, and more preferably 3 parts by mass or more with respect to 100 parts by mass of the polyurethane resin (X). Is. Further, it is necessary to be 30 parts by mass or less, preferably 25 parts by mass or less, and more preferably 20 parts by mass or less. Within the above range, excellent adhesiveness, heat resistance, and surface hardness can be exhibited.
- composition for a film adhesive, an ink binder or a coating agent of the present invention is a composition containing the polyurethane resin (X) and the cross-linking agent (Y), and in particular, a film.
- Suitable for adhesives, ink binders or coatings The content of the polyurethane resin (X) in the solid content of the composition is preferably 60% by mass or more, more preferably 70% by mass or more, and further preferably 80% by mass or more. Further, it is preferably 98% by mass or less, more preferably 95% by mass or less, and further preferably 93% by mass or less.
- the composition of the present invention can be diluted with an organic solvent to form a varnish.
- the organic solvent is not particularly limited, but is an ester solvent (ethyl acetate, butyl acetate, ethyl butyrate, etc.), an ether solvent (dioxane, tetrahydrofuran, diethyl ether, etc.), a ketone solvent (cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone, etc.). ), Aromatic hydrocarbon solvents (benzene, toluene, xylene, etc.) and mixed solvents thereof.
- the organic solvent is preferably 50 parts by mass or more, more preferably 100 parts by mass or more, and further preferably 200 parts by mass or more with respect to 100 parts by mass of the polyurethane resin (X). Further, it is preferably 2000 parts by mass or less, more preferably 1000 parts by mass or less, and further preferably 500 parts by mass or less. Within the above range, the storage stability of the composition is good, and the coatability on the substrate is improved. It is also advantageous in terms of cost.
- composition can contain known additives such as UV absorbers and antioxidants as long as the effects of the present invention are not impaired.
- the composition of the present invention has excellent adhesiveness to all kinds of substrates including polyester and polycarbonate and also has excellent heat resistance, it is useful for pre-coating film adhesive applications such as steel sheets.
- the film is not particularly limited, and examples thereof include a resin film and a metal film. That is, the composition of the present invention is suitable for an adhesive between a resin film and a resin film, a resin film and a metal film, or a resin film and a metal film.
- the composition of the present invention can be applied to one of the films, dried to form an adhesive layer, and then the other film can be attached.
- the resin film examples include films such as polyester resin, polyamide resin, polyimide resin, polyamideimide resin, polycarbonate resin, liquid crystal polymer, polyphenylene sulfide, syndiotactic polystyrene, polyolefin resin, and fluorine resin. Of these, a polycarbonate resin film is preferable.
- the thickness of the resin film is not particularly limited, but is preferably 1 ⁇ m or more, more preferably 3 ⁇ m or more, and further preferably 10 ⁇ m or more. Further, it is preferably 100 ⁇ m or less, more preferably 50 ⁇ m or less, and further preferably 20 ⁇ m or less.
- the metal film examples include various metals such as SUS, copper, aluminum, iron, steel, zinc and nickel, and various films such as alloys, plated products and metals treated with other metals such as zinc and chromium compounds. ..
- the thickness of the metal film is not particularly limited, but is preferably 1 ⁇ m or more, more preferably 3 ⁇ m or more, and further preferably 10 ⁇ m or more. Further, it is preferably 50 ⁇ m or less, more preferably 30 ⁇ m or less, and further preferably 20 ⁇ m or less.
- the thickness of the adhesive layer after drying is not particularly limited, but is preferably 1 ⁇ m or more, more preferably 2 ⁇ m or more, and further preferably 5 ⁇ m or more. Further, it is preferably 20 ⁇ m or less, more preferably 15 ⁇ m or less, and further preferably 5 ⁇ m or less. Within the above range, the adhesiveness and heat resistance are improved.
- the composition of the present invention has excellent adhesiveness to all kinds of substrates including polyester and polycarbonate, and also has excellent heat resistance, so that the outflow of the coating film can be suppressed, which is useful for ink binder applications. Is. It is especially useful for screen inks and ink binders for decorative molding.
- the composition of the present invention is also useful for coating agents because it has excellent adhesiveness to a metal substrate such as aluminum and has excellent surface hardness.
- it is useful as a coating agent for protecting the surface of ink and parts inside and outside automobiles.
- composition of polyurethane resin (X)> The molar ratio of the monomer components constituting the polyurethane resin (X) was quantified using a 1 H-nuclear magnetic resonance spectrum apparatus (NMR) at 400 MHz. Deuterated chloroform was used as the solvent.
- the glass transition temperature was defined as the temperature at the refraction point of the storage elastic modulus (E').
- the obtained polyurethane resin (X) solution is applied to a polypropylene film (P2161, manufactured by Toyobo Co., Ltd., thickness 50 ⁇ m) with a wet film thickness (thickness before drying) of 200 ⁇ m, and heated at 120 ° C. for 1 hour to volatilize (dry) the solvent. ). Then, after the polyurethane resin (X) solution was dried, the film was peeled off from the polypropylene film to obtain a sample film of the polyurethane resin (X).
- the glass transition temperature of the sample film was measured.
- a dynamic viscoelasticity measuring device DVA-220 manufactured by IT Measurement Control Co., Ltd. was used, and the temperature dependence of 0 ° C. to 150 ° C. (4 ° C./min, 10 Hz) was measured.
- polyurethane resin (U1) 100 parts of UC-100 (polycarbonate diol manufactured by Ube Kosan), 5 parts of neopentyl glycol, methyl ethyl ketone (in a reaction vessel equipped with a thermometer, agitator, a reflux condenser and a distillation tube) 204 parts of MEK) was charged, and after dissolution, 31 parts of isophorone diisocyanate was added and stirred to obtain a uniform solution. Then, 0.5 part of BiCAT8210 (manufactured by The Shepherd Chemical Company) was added as a catalyst, and the mixture was reacted at 75 ° C. for 5 hours.
- UC-100 polycarbonate diol manufactured by Ube Kosan
- Examples 1 to 11 Comparative Examples 1 to 4 Laminates were prepared using the polyurethane resins (U1) to (U11), and the initial adhesive strength (adhesiveness), heat resistance, and pencil hardness were evaluated.
- D-110N manufactured by Mitsui Chemicals, solid content concentration 75% by mass
- Preparation of laminate A solution of polyurethane resin (P1) was applied to a polycarbonate film (manufactured by Sumitomo Bakelite, EC105, 0.5 mm) with a bar coater so that the dry film thickness (film thickness after drying) was 5 ⁇ m, and the temperature was 120 ° C. The solvent was volatilized (dried) by heating for 3 minutes. Next, a polycarbonate film (manufactured by Sumitomo Bakelite, EC105, 0.5 mm) was pressure-bonded (dry lamination) to the polyurethane resin surface of the film using a dry laminator.
- a polycarbonate film manufactured by Sumitomo Bakelite, EC105, 0.5 mm
- Dry lamination was performed at a roll temperature of 120 ° C., a roll load of 3 kg / cm, and a speed of the object to be crimped at 1 m / min. Then, it was aged at 80 ° C. for 1 hour to obtain a laminate.
- Pencil hardness test The laminate was prepared on a tin plate (JIS G3303 (2017)) by the same method, and evaluated by a pencil hardness test method according to JIS standard (K5600-5-4 (1999)). (evaluation) ⁇ : 2H or more ⁇ : less than 2H, H or more ⁇ : less than H, F or more ⁇ : less than F
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Abstract
Description
本発明に用いるポリカーボネートポリオール(A)は、下記一般式(1)で表される構造を含むことが必要である。含有量はポリカーボネートポリオール(A)全体を100モル%としたとき、一般式(1)で表される構造を60モル%以上含有することが必要であり、好ましくは70モル%以上であり、より好ましくは80モル%以上であり、さらに好ましくは90モル%以上であり、特に好ましくは95モル%以上であり、100モル%でも差し支えない。一般式(1)で表される構造を含有することでポリウレタン樹脂(X)に柔軟性を付与し、優れた接着性、耐熱性、および表面硬度を発現することができる。
ポリカーボネートジオール(A)の数平均分子量は下記式により算出した。
数平均分子量=(56.1×1000×価数)/水酸基価[mgKOH/g]
前記式中において、価数は1分子中の水酸基の数であり、[mgKOH/g]は水酸基価の単位である。
本発明で用いられる有機ジイソシアネート(B)は、テトラメチレンジイソシアネート、ヘキサメチレンジイソシアネート(HDI)、2-メチル-1,5-ペンタンジイソシアネート、デカメチレンジイソシアネート、3-メチル-1,5-ペンタンジイソシアネート、リジンジイソシアネート等の脂肪族ジイソシアネート;イソホロンジイソシアネート(IPDI)、水素添加トリレンジイソシアネート、水素添加ジフェニルメタンジイソシアネート、水素添加キシリレンジイソシアネート、水素添加テトラメチルキシリレンジイソシアネート、シクロヘキシルジイソシアネート等の脂環族ジイソシアネート;2,4-トリレンジイソシアネート、2,6-トリレンジイソシアネート、4,4’-ジフェニルメタンジイソシアネート(MDI)、2,4’-ジフェニルメタンジイソシアネート、2,2’-ジフェニルメタンジイソシアネート、1,5-ナフチレンジイソシアネート、1,4-ナフチレンジイソシアネート、o-フェニレンジイソシアネート、p-フェニレンジイソシアネート、m-フェニレンジイソシアネート、o-キシリレンジイソシアネート、m-キシリレンジイソシアネート、p-キシリレンジイソシアネート、テトラメチルキシリレンジイソシアネート、4,4’-ジフェニルエーテルジイソシアネート、2-ニトロジフェニル-4,4’-ジイソシアネート、2,2’-ジフェニルプロパン-4,4’-ジイソシアネート、3,3’-ジメチルジフェニルメタン-4,4’-ジイソシアネート、4,4’-ジフェニルプロパンジイソシアネート、3,3’-ジメトキシジフェニル-4,4’-ジイソシアネート等の芳香族ジイソシアネートが挙げられる。また、前記有機ジイソシアネートを2種類以上含む混合物、これらの有機ジイソシアネートのウレタン変性体、アロファネート変性体、ウレア変性体、ビウレット変性体、ウレトジオン変性体、ウレトイミン変性体、イソシアヌレート変性体、カルボジイミド変性体等が挙げられる。本発明で好ましい有機ジイソシアネートは、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、4,4’-ジフェニルメタンジイソシアネートが好ましく、さらには、得られるポリウレタン樹脂(X)の溶剤溶解性が良く、また製造時のゲル化のおそれが小さく耐候性及び樹脂の機械的強度に優れるイソホロンジイソシアネートが特に好ましい。
本発明で用いられる鎖延長剤(C)は、ポリウレタン樹脂(X)の分子鎖を延ばすものであれば特に限定されず、有機ジイソシアネート(B)と反応する基を有するものであることが好ましい。鎖延長剤(C)としては、特に限定されないが、製造時のゲル化や反応性の観点から、ポリオール化合物であることが好ましく、より好ましくはグリコール化合物である。グリコール化合物としては、脂肪族グリコール化合物、芳香族グリコール化合物または脂環族グリコール化合物のいずれでも構わないが、脂肪族グリコール化合物であることが好ましい。なかでも炭素数が10以下の直鎖または分岐の脂肪族グリコール化合物であることが好ましく、炭素数が7以下の直鎖または分岐の脂肪族グリコール化合物であることがより好ましい。具体的には、エチレングリコール、1,2-プロパンジオール、1,3-プロパンジオール、1,2-ブタンジオール、1,3-ブタンジオール、1,4-ブタンジオール、1,5-ペンタンジオール、1,6-ヘキサンジオール、3-メチル-1,5-ペンタンジオール、ネオペンチルグリコール、2-エチル-4-ブチル-1,3-プロパンジオール、ジエチレングリコール、ジプロピレングリコール、ネオペンチルグリコール等が挙げられる。本発明においては、反応性、耐熱性の観点からネオペンチルグリコールまたは1,6-ヘキサンジオールが好ましい。
本発明のポリウレタン樹脂(X)のガラス転移温度は50℃以上であることが必要である。好ましくは55℃以上であり、より好ましくは60℃以上である。前記下限値以上にすることにより、熱負荷による基材との接着性低下を抑え、流れ出しの発生を抑制することができる。また、120℃以下であることが好ましい。より好ましくは110℃以下であり、さらに好ましくは100℃以下であり、特に好ましくは95℃以下である。前記上限値以下にすることにより、基材に対する接着性の低下を抑えることができる。
本発明で用いる架橋剤(Y)は、前記ポリウレタン樹脂(X)と反応して架橋するものであれば特に限定されない。好ましくは1分子中に2個以上の官能基を有する化合物であり、官能基としては、イソシアネート基、エポキシ基、アミノ基、メチロール基、アルコキシメチル基、イミノ基、金属キレート基、アジリジニル基等が挙げられる。具体的な化合物としては、多官能イソシアネート化合物、多官能エポキシ化合物、多官能メラミン化合物、金属架橋剤、多官能アジリジン化合物等が挙げられる。
本発明のフィルム接着剤、インキバインダーまたはコーティング剤用組成物(以下、単に組成物ともいう。)は、前記ポリウレタン樹脂(X)および前記架橋剤(Y)を含有する組成物であり、特にフィルム接着剤、インキバインダーまたはコーティング剤用途に適している。組成物の固形分中、ポリウレタン樹脂(X)の含有量は60質量%以上であることが好ましく、より好ましくは70質量%以上であり、さらに好ましくは80質量%以上である。また、98質量%以下であることが好ましく、より好ましくは95質量%以下であり、さらに好ましくは93質量%以下である。前記範囲内で含有することにより、優れた接着性、耐熱性、および表面硬度を発現することができる。
本発明の組成物はポリエステルやポリカーボネートを含めたあらゆる種類の基材への接着性に優れ、また、耐熱性にも優れることから、鋼板などにおけるプレコーティング方式のフィルム接着剤用途に有用である。フィルムとしては、特に限定されないが、樹脂フィルムまたは金属フィルムが挙げられる。すなわち、本発明の組成物は、樹脂フィルムと樹脂フィルム、樹脂フィルムと金属フィルム、または樹脂フィルムと金属フィルムとの接着剤に好適である。前記一方のフィルムに本発明の組成物を塗布、乾燥し、接着剤層を形成した後、他方のフィルムを貼り合わせることができる。
本発明の組成物は、ポリエステルやポリカーボネートを含めたあらゆる種類の基材への接着性に優れ、また、耐熱性にも優れることから、塗膜の流れ出しを抑えることができ、インキバインダー用途に有用である。特にスクリーンインキや加飾成形用のインキバインダーに有用である。
本発明の組成物は、アルミなどの金属基材への接着性にも優れ、また、優れた表面硬度を有していることから、コーティング剤用途に有用である。特にインキや自動車内外部品の表面保護用のコーティング剤に有用である。
400MHzの1H-核磁気共鳴スペクトル装置(NMR)を用い、ポリウレタン樹脂(X)を構成するモノマー成分のモル比定量を行った。溶媒には重クロロホルムを使用した。
4mlのテトラヒドロフラン(テトラブチルアンモニウムクロライド5mM添加)に試料(ポリカーボネートポリオール(A)またはポリウレタン樹脂(X))4mgを溶解した後、0.2μmのメンブレンフィルターでろ過して試料溶液とした。試料溶液をゲル浸透クロマトグラフィーで分析を行った。装置はTOSOH HLC-8220、検出器は示差屈折率検出器を用い、流速1mL/分、カラム温度40℃で測定した。分子量標準には単分散ポリスチレンを使用し、数平均分子量は標準ポリスチレン換算値とし、分子量1000未満に相当する部分を省いて算出した。
ガラス転移温度は動的粘弾性の温度依存性測定結果より、保存弾性率(E’)の屈折点における温度をガラス転移温度とした。得られたポリウレタン樹脂(X)溶液をポリプロピレンフィルム(東洋紡社製P2161、厚み50μm)にウェット膜厚(乾燥前の厚み)200μmで塗布し、120℃で1時間加熱を行い、溶媒を揮発(乾燥)させた。次いで、ポリプロピレンフィルムからポリウレタン樹脂(X)溶液の乾燥後フィルムを剥がし、ポリウレタン樹脂(X)の試料フィルムとした。該試料フィルムのガラス転移温度を測定した。装置は、アイティー計測制御株式会社製の動的粘弾性測定装置DVA-220を使用し、0℃~150℃(4℃/min、10HHz)の温度依存性を測定した。
温度計、攪拌機、還流式冷却管および蒸留管を具備した反応容器に、UC-100(宇部興産製ポリカーボネートジオール)を100部、ネオペンチルグリコールを5部、メチルエチルケトン(MEK)を204部仕込み、溶解後、イソホロンジイソシアネート31部を投入し、撹拌して均一溶液とした。その後、触媒としてBiCAT8210(The Shepherd Chemical Company製)を0.5部加え75℃で5時間反応させた。充分に反応させて、メチルエチルケトン(MEK)を113部投入し攪拌後、目的とする固形分濃度(NV)30質量%のポリウレタン樹脂(U1)の溶液を得た。この様にして得られたポリウレタン樹脂(U1)の特性を表1に示す。
ポリウレタン樹脂(U1)の製造例と同様にして、但し、原料の種類と配合比率を変更して、ポリウレタン樹脂(U2)~(U11)を得た。それらの特性を表1に示す。
前記ポリウレタン樹脂(U1)~(U11)を用いて積層体を作製し、初期接着力(接着性)、耐熱性、および鉛筆硬度の評価を行った。なお、実施例1~10については、架橋剤としてD-110N(三井化学製、固形分濃度75質量%)をポリウレタン樹脂100質量部(固形分換算)に対し、1~30質量部(固形分換算)添加して評価した。
ポリカーボネートフィルム(住友ベークライト製、EC105、0.5mm)にポリウレタン樹脂(P1)の溶液をドライ膜厚(乾燥後の膜厚)が5μmになるようにバーコーターで塗布し、120℃で3分間加熱を行い、溶媒を揮発(乾燥)させた。次いで、前記フィルムのポリウレタン樹脂面にポリカーボネートフィルム(住友ベークライト製、EC105、0.5mm)をドライラミネーターを用いて圧着(ドライラミネーション)させた。ドライラミネーションは、ロール温度120℃、ロール荷重3kg/cm、被圧着物速度1m/分で行った。次いで、80℃、1時間のエージングを行ない、積層体を得た。
前記積層体を幅15mmの短冊状に切り取り、テンシロン(登録商標)(東洋測器(株)製、UTM-IV)での剥離(T型ピール剥離、引っ張り速度100mm/分)を行い、剥離の様子を観察して接着性を評価した。評価結果を表2に示す。
(評価)
○:接着剤凝集破壊または材料破壊となった。
△:界面剥離で、かつ接着強度が10N/15mmであった。
×:接着強度が10N/15mm未満であった。
前記積層体を105℃で300時間処理(静置)を行い、初期接着力試験と同様に接着性を評価した。
(評価)
◎:浮きは発生せず、接着剤凝集破壊または材料破壊となった。
○:浮きは発生せず、主に凝集剥離であるが、一部界面剥離となった。
△:浮きは発生せず、界面剥離となった。
×:浮きが発生した。
ブリキ板(JIS G3303(2017))上に前記積層体を同様の方法で作製し、JIS規格(K5600-5-4(1999))にのっとった鉛筆硬度試験法により評価した。
(評価)
◎:2H以上
○:2H未満、H以上
△:H未満、F以上
×:F未満
UC-100:宇部興産製ポリカーボネートジオール、数平均分子量=1000、ポリカーボネートポリオール(A)における、一般式(1)で示される構造の含有比率100モル%
UH-100:宇部興産製ポリカーボネートジオール、数平均分子量=1000、ポリカーボネートポリオール(A)における、一般式(1)で示される構造の含有比率0モル%
PH-100:宇部興産製ポリカーボネートジオール、数平均分子量=1000、ポリカーボネートポリオール(A)における、一般式(1)で示される構造の含有比率0モル%
UM-90(3/1):1,4-シクロヘキサンジメタノールと1,6-ヘキサンジオールをベースとした宇部興産製のポリカーボネートジオール、数平均分子量=900、ポリカーボネートポリオール(A)における、一般式(1)で示される構造の含有比率75モル%
UM-90(1/1):1,4-シクロヘキサンジメタノールと1,6-ヘキサンジオールをベースとした宇部興産製のポリカーボネートジオール、数平均分子量=900、ポリカーボネートポリオール(A)における、一般式(1)で示される構造の含有比率50モル%
D-110N:三井化学製、メタキシリレンジイソシアネートのトリメチロールプロパンアダクト体、固形分比率75質量%
IPDI:イソホロンジイソシアネート
MDI:ジフェニルメタンジイソシアネート
HDI:ヘキサメチレンジイソシアネート
NPG:ネオペンチルグリコール
HD:1,6-ヘキサンジオール
Claims (3)
- 前記有機ジイソシアネート(B)がイソホロンジイソシアネート、4,4’-ジフェニルメタンジイソシアネートまたはヘキサメチレンジイソシアネートである請求項1に記載のフィルム接着剤、インキバインダーまたはコーティング剤用組成物。
- 前記鎖延長剤(C)が炭素数7以下のグリコール化合物である請求項1または2に記載のフィルム接着剤、インキバインダーまたはコーティング剤用組成物。
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- 2021-02-05 WO PCT/JP2021/004434 patent/WO2021157726A1/ja unknown
- 2021-02-05 KR KR1020227028375A patent/KR20220136370A/ko active Search and Examination
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Publication number | Publication date |
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TW202134308A (zh) | 2021-09-16 |
CN115003771B (zh) | 2023-08-04 |
CN115003771A (zh) | 2022-09-02 |
JPWO2021157726A1 (ja) | 2021-08-12 |
US20230081425A1 (en) | 2023-03-16 |
EP4101904A4 (en) | 2024-01-24 |
KR20220136370A (ko) | 2022-10-07 |
EP4101904A1 (en) | 2022-12-14 |
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