JPWO2019244980A1 - ポリマーと被接着物との接着積層体の製造方法 - Google Patents
ポリマーと被接着物との接着積層体の製造方法 Download PDFInfo
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- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
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- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
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- 229920006231 aramid fiber Polymers 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
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- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
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- 238000001746 injection moulding Methods 0.000 description 1
- BIZCJSDBWZTASZ-UHFFFAOYSA-N iodine pentoxide Inorganic materials O=I(=O)OI(=O)=O BIZCJSDBWZTASZ-UHFFFAOYSA-N 0.000 description 1
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- 239000012948 isocyanate Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- KAGBQTDQNWOCND-UHFFFAOYSA-M lithium;chlorite Chemical compound [Li+].[O-]Cl=O KAGBQTDQNWOCND-UHFFFAOYSA-M 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- NWAPVVCSZCCZCU-UHFFFAOYSA-L magnesium;dichlorite Chemical compound [Mg+2].[O-]Cl=O.[O-]Cl=O NWAPVVCSZCCZCU-UHFFFAOYSA-L 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- 239000000113 methacrylic resin Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910000127 oxygen difluoride Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- LLYCMZGLHLKPPU-UHFFFAOYSA-N perbromic acid Chemical compound OBr(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-N 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- 229920000739 poly(3-hydroxycarboxylic acid) polymer Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- VISKNDGJUCDNMS-UHFFFAOYSA-M potassium;chlorite Chemical compound [K+].[O-]Cl=O VISKNDGJUCDNMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
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- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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- 239000008213 purified water Substances 0.000 description 1
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- 229910052761 rare earth metal Inorganic materials 0.000 description 1
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000013464 silicone adhesive Substances 0.000 description 1
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- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Images
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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
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
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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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Laminated Bodies (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
ポリマーをハロゲン酸化物ラジカルと反応させる、表面処理工程、および、
前記表面処理工程後の前記ポリマーの表面および被接着物の表面の少なくとも一方に、接着剤を塗布して、前記ポリマーと前記被接着物とを接着する接着工程を含み、
前記ポリマーが、主鎖に芳香環を有するポリマーであることを特徴とする。
本発明において、前記表面処理工程に供するポリマー(以下、処理前ポリマーともいう。)は、主鎖に芳香環を有するポリマーである。後述する表面処理工程によれば、例えば、前記ポリマーの主鎖に含まれる芳香環の側鎖が、改質される。前記芳香環の種類は、特に制限されず、例えば、ナフチレン基、アントラセニレン基、フェナントリレン基、クリセニレン基、ピレニレン基、ベンゾアントラセニレン基、フルオランテニレン基、ベンゾフルオランテニレン基、ペリレニレン基、コロネリレン基、ピセニレン基、ジフェニルアントラセニレン基、フルオレニレン基、トリフェニリレン基、ルビセニレン基、フェニルアントラセニレン基、ビスアントラセニレン基、ジアントラセニルベンジニレン基、ジベンゾアントラセニレン基等があげられ、好ましくは、ナフチレン基、アントラセニレン基、フェナントリレン基、クリセニレン基、ピレニレン基、ベンゾアントラセニレン基等があげられる。前記処理前ポリマーは、例えば、エンジニアプラスチックがあげられ、具体例として、液晶ポリマーがあげられる。
前記ハロゲン酸化物ラジカルは、ハロゲン酸化物のラジカルであって、その種類は特に制限されず、例えば、F2O・(二フッ化酸素ラジカル)、F2O2 ・(二フッ化二酸素ラジカル)、ClO2 ・(二酸化塩素ラジカル)、BrO2 ・(二酸化臭素ラジカル)、I2O5 ・(酸化ヨウ素(V)ラジカル)等があげられる。
前記表面処理工程は、例えば、前記処理前ポリマーを配置した反応系に、前記ハロゲン酸化物ラジカルを共存させることで行うことができる。前記処理前ポリマーは、前記ハロゲン酸化物を含む反応系に配置すればよい。前記ハロゲン酸化物ラジカルは、例えば、前記反応系において生成させることで、前記反応系に含ませてもよいし、別途生成させた前記ハロゲン酸化物ラジカルを前記反応系に導入してもよい。前記ハロゲン酸化物ラジカルの発生方法は、特に制限されず、具体例を後述する。前記反応系は、例えば、気体反応系でも、液体反応系でもよい。
前記気体反応系の場合、例えば、前記ハロゲン酸化物ラジカルを含む気体反応系中に、前記処理前ポリマーを配置し、光照射する。前記気体反応系における気相の種類は、特に制限されず、例えば、空気、窒素、希ガス、酸素等である。前記気体反応系を収容する反応器は、例えば、光照射を外部から行う場合、光透過性の容器が好ましく、光照射を内部から行う場合、光透過性の容器には限られない。
前記液体反応系は、例えば、有機相を含む。前記液体反応系は、例えば、前記有機相のみを含む一相反応系でも、前記有機相と水相とを含む二相反応系でもよい。
前記表面処理工程は、前述のとおり、前記処理前ポリマーをハロゲン酸化物ラジカルと反応させて、その表面が改質された処理済ポリマー(以下、改質ポリマーともいう)を得る工程である。本発明の表面処理工程によれば、前記処理前ポリマーの表面を前記ハロゲン酸化物ラジカルと反応させることで、前記処理前ポリマーの表面が改質された改質ポリマーが得られる。前記改質ポリマーの改質の程度(例えば、酸化の程度)は、例えば、前記ハロゲン酸化物ラジカルの量、光照射の時間の長さ等により調整できる。また、前記改質ポリマーの改質の程度を調整することで、例えば、過剰な改質による前記改質ポリマーにおけるポリマーの分解を抑制でき、前記改質ポリマーにおける前記処理前ポリマーが本来有する特性を維持できる。
前記接着工程は、前記表面処理工程後の前記改質ポリマーの表面および被接着物の表面の少なくとも一方に、接着剤を塗布して、前記ポリマーと前記被接着物とを接着する。本発明によれば、前述のように、前記表面処理工程により前記ポリマーを改質できるため、例えば、接着剤を塗布しても前記被接着物と接着できなかったポリマーについて、前記接着剤との親和性が向上し、前記接着剤による前記被接着物との接着が可能になる。前記被接着物および前記接着剤は、特に制限されず、後述のようなものが例示できる。
前記接着剤は、特に限定されず、様々な接着剤が利用できる。前記前処理工程によれば、例えば、前記改質ポリマーは、ハロゲン酸化物ラジカルとの反応によって、改質(例えば、酸化)される。このため、前記改質ポリマーの表面に含まれる改質により形成された官能基(例えば、ヒドロキシ基等)によって、前記接着剤との親和性を向上することができる。接着剤は、特に限定されず、市販のものを用いてもよい。
前記被接着物は、特に限定されず、例えば、金属、ポリマー、セラミック、ガラス、布、紙等があげられる。前記金属は、特に限定されず、例えば、アルミニウム、ニッケル、鉄、金、銀、銅等、また、ジュラルミン、高張力鋼、ステンレス鋼などの合金等があげられる。前記ポリマーは、例えば、前記処理前ポリマーと同じポリマーでもよいし、その他の異なるポリマーでもよい。前記セラミックは、特に限定されず、例えば、ジルコニア、酸化アルミニウム、フェライト、チタン酸バリウム、窒化ホウ素、炭化ケイ素、窒化ケイ素、ステアタイト等があげられる。
本発明は、例えば、さらに、前記ハロゲン酸化物ラジカルを生成させる生成工程を含んでもよい。前記生成工程は、例えば、前記表面処理工程の前に行ってもよいし、前記表面処理工程と同時に行ってもよい。前記ハロゲン酸化物ラジカルの生成方法は、特に制限されない。
本発明は、例えば、前記前処理工程後、前記接着工程の前、さらに、前記改質ポリマーの改質された領域に、官能基を導入する工程を含んでもよい。本発明によれば、さらに、官能基化することによって、前記改質ポリマー層の物性をさらに変えることもできる。
液晶ポリマーフィルムを改質し、接着剤を介した被接着物との接着性を確認した。
長さ50mm×幅15mm×厚み2mmの液晶ポリマー(LCP)フィルム(商品名UENO LCP、6030G-MF、上野製薬社製)を準備し、一方の表面に、以下に示すようにして改質処理を行った。
前記改質LCPフィルムと未改質LCPフィルムとについて、それぞれの表面の濡れ性を確認した。具体的には、各フィルムの表面に、水5μLを滴下して、水滴の形状から濡れ性を判断した。図2(A)に、前記未改質LCPフィルム上の液滴の写真を示し、図2(B)に、前記改質LCPフィルム上の液滴の写真を示す。図2に示すように、前記改質LCPフィルムの液滴は接触角が、前記未改質LCPフィルムよりも小さくなっていることから、濡れ性が向上したといえる。そして、濡れ性の向上は、前記改質LCPフィルムにおいて、前記未改質LCPよりも水酸基が多く導入されていることを意味すると解される。
図3の斜視図に示すように、前記改質LCPフィルムと前記被接着物とを接着させ、積層体を製造した。
前記積層体について、図3(B)に示すように、前記改質LCPフィルムの端部と前記被接着物の端部とを、それぞれ反対方向に30N/minの強さで引張り、引張強度(せん断応力)を測定した。この結果を、下記表1に示す。
前記液晶ポリマーフィルムに代えて、PETフィルムを改質し、前記実施例1と同様にして、改質PETフィルムと、前記被接着物である未改質PETフィルムとの接着剤による接着を確認した。その結果、前記未改質PETフィルムは、被接着物(未改質PETフィルム)との界面が剥離したのに対して、前記改質PETフィルムは、被接着物(未改質PETフィルム)と接着し、引張強度は1.2MPa(N/mm2)であった。
2 水相
10 改質LCPフィルム
11 接着剤
12 被接着物
Claims (10)
- ポリマーをハロゲン酸化物ラジカルと反応させる、表面処理工程、および、
前記表面処理工程後の前記ポリマーの表面および被接着物の表面の少なくとも一方に、接着剤を塗布して、前記ポリマーと前記被接着物とを接着する接着工程を含み、
前記ポリマーが、主鎖に芳香環を有するポリマーであることを特徴とする前記ポリマーと前記被接着物との接着積層体の製造方法。 - 前記ポリマーが、液晶ポリマーである、請求項1に記載の接着積層体の製造方法。
- 前記接着剤が、水親和性の接着剤である、請求項1に記載の接着積層体の製造方法。
- 前記接着剤が、水を開始剤として重合するモノマーを含む、請求項1に記載の接着積層体の製造方法。
- 前記モノマーが、シアノアクリレートモノマーである、請求項4に記載の接着積層体の製造方法。
- 前記接着剤が、エポキシ系接着剤である、請求項1から4のいずれか一項に記載の接着積層体の製造方法。
- 前記表面処理工程の反応系が、気体反応系または液体反応系である、請求項1から6のいずれか一項に記載の接着積層体の製造方法。
- 前記ハロゲン酸化物ラジカルが、二酸化塩素ラジカルである、請求項1から7のいずれか一項に記載の接着積層体の製造方法。
- 前記表面処理工程に供する前記ポリマーが、シート、フィルム、プレート、チューブ、パイプ、棒、ビーズ、ブロック、織布、不織布および糸からなる群から選択された少なくとも一つの成形体である、請求項1から8のいずれか一項に記載の接着積層体の製造方法。
- 前記被接着物が、金属またはポリマーである、請求項1から9のいずれか一項に記載の接着積層体の製造方法。
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