JPS62260868A - Coating composition - Google Patents
Coating compositionInfo
- Publication number
- JPS62260868A JPS62260868A JP10419086A JP10419086A JPS62260868A JP S62260868 A JPS62260868 A JP S62260868A JP 10419086 A JP10419086 A JP 10419086A JP 10419086 A JP10419086 A JP 10419086A JP S62260868 A JPS62260868 A JP S62260868A
- Authority
- JP
- Japan
- Prior art keywords
- coating composition
- acid
- compsn
- solvent
- coating
- 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.)
- Pending
Links
- 239000008199 coating composition Substances 0.000 title claims description 11
- -1 methylsilyl Chemical group 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 229920005989 resin Polymers 0.000 claims abstract description 8
- 239000011347 resin Substances 0.000 claims abstract description 8
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 11
- 239000011248 coating agent Substances 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract description 3
- 229920001577 copolymer Polymers 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract 2
- OSPSWZSRKYCQPF-UHFFFAOYSA-N dibutoxy(oxo)phosphanium Chemical compound CCCCO[P+](=O)OCCCC OSPSWZSRKYCQPF-UHFFFAOYSA-N 0.000 abstract 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 19
- 230000000704 physical effect Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OVOUKWFJRHALDD-UHFFFAOYSA-N 2-[2-(2-acetyloxyethoxy)ethoxy]ethyl acetate Chemical compound CC(=O)OCCOCCOCCOC(C)=O OVOUKWFJRHALDD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 2
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- FJSRPVWDOJSWBX-UHFFFAOYSA-N 1-chloro-4-[1-(4-chlorophenyl)-2,2,2-trifluoroethyl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)C1=CC=C(Cl)C=C1 FJSRPVWDOJSWBX-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔発明の技術分野〕
本発明はフッ素樹脂系室温硬化型被覆剤、特にシリルイ
ソシアネートと特定の硬化剤を使用したー液性室温硬化
被覆剤に係るものである。DETAILED DESCRIPTION OF THE INVENTION [Technical Field of the Invention] The present invention relates to a fluororesin-based room temperature curing coating material, particularly a liquid room temperature curing coating material using a silyl isocyanate and a specific curing agent.
各種樹脂をベースにした被覆剤が広く使用されているが
、特にフッ素樹脂系重合体をベースとした被覆剤厚電子
部品や精密機械から車輌構造物として注目されている。Coatings based on various resins are widely used, but coatings based on fluororesin polymers are particularly attracting attention for use in electronic parts, precision machinery, and vehicle structures.
これはフッ素樹脂本来の耐候性、耐薬品性や欠粒性に優
れた素材であるが硬化工程に厳しい条件が必要とされる
傾向にあった。このフッＲＪｆＡ脂の中でも特に良好な
物性が期待されるフルオロオレフィンと炭化水素系ビニ
ールエーテルの交互共重合体は樹脂中に導入されたＯ
ＨＩを介した硬化が行なわれているが、非常に繁雑であ
った。又同様にパークロロ基をもつアクリレートやポリ
エステルアルキッド系の樹脂でも同様であった。Although this material has excellent weather resistance, chemical resistance, and particle chipping properties inherent to fluororesins, it tends to require strict conditions in the curing process. Among these fluoro-RJfA resins, alternating copolymers of fluoroolefins and hydrocarbon vinyl ethers, which are expected to have particularly good physical properties, are
Curing via HI has been performed, but was very complicated. Similarly, acrylate and polyester alkyd resins having perchloro groups were also found to have the same effect.
例示されている硬化方法ではメチロール化メラミンと酸
触媒を用い（３０分１４０℃）（５分２１０℃）で焼付
ける１液焼付硬化方法や有機イソシアネートとｆｉ機ス
ズ触媒を用いた常温３日硬化の２液性方法がある。これ
らのｈ法は被覆剤に適用する硬化方法とは温度が畠すぎ
るとか、硬化時間が長ずぎると言う欠点があり一般的に
は適用し難いものであった。Examples of curing methods include a one-component baking curing method using methylolated melamine and an acid catalyst (30 minutes at 140°C) and (5 minutes at 210°C), and a 3-day curing method at room temperature using an organic isocyanate and a fi machine tin catalyst. There is a two-component method. These H methods have drawbacks such as the temperature being too high and the curing time being too long compared to curing methods applied to coating materials, and are generally difficult to apply.
特開昭６０−１２７３７３号公報には、ヒドロキシ基を
有するフッ素樹脂をテトラブトキシチタンとともに、ブ
タノールを含むＯＲ溶媒に溶解して被覆組成物とする例
が示されているが、硬化物の物性が３日経過後に測定さ
れているように、その硬化速度は遅い。又この場合チタ
ン化合物特有の経口的黄変現象が不可避であり本来のフ
ッ素樹脂の特性が損なわれるという欠点も予見され、満
足すべきものではない。JP-A-60-127373 discloses an example in which a coating composition is prepared by dissolving a fluororesin having a hydroxyl group together with tetrabutoxytitanium in an OR solvent containing butanol, but the physical properties of the cured product are Its curing rate is slow, as measured after 3 days. Further, in this case, the disadvantage that oral yellowing phenomenon peculiar to titanium compounds is unavoidable and the original characteristics of the fluororesin is impaired is also foreseen, which is not satisfactory.
又特開昭６０−１０６８６２号公報記載の発明ではパー
クロロアルキル基を持つエチルシリケートでフッ素樹脂
を変性しているが、シリケートは反応が低いため、加圧
下１２０℃で３時間保持して物性を測定しているように
きびしい硬化条件でなければ硬化しなかった。Furthermore, in the invention described in JP-A-60-106862, a fluororesin is modified with ethyl silicate having a perchloroalkyl group, but since silicate has a low reactivity, the physical properties were maintained at 120°C for 3 hours under pressure. As measured, it did not cure unless the curing conditions were severe.
そこで本発明者らはフッ素樹脂のもつ優れた特性を活用
でき穏やかな硬化条件で硬化しうる被覆組成物を提供す
ることを目的として種々研究を重樹脂系組成物は一液室
温硬化性であり硬化被膜の経口変色や物性の低下しなく
好ましい被覆組成物であることを見出して本発明に至っ
た。Therefore, the present inventors have conducted various studies with the aim of providing a coating composition that can take advantage of the excellent properties of fluororesins and can be cured under mild curing conditions. The inventors have discovered that the coating composition is a preferable coating composition that does not cause oral discoloration of the cured film or deterioration of physical properties, and has led to the present invention.
よって本発明はヒドロキシル基をもつフル第１コオレフ
イン系樹脂に、シリルイソシアネートと、酸性リン酸エ
ステル化合物ないしホスホン酸化合物と、有機溶剤とを
加えて調製してなる被覆組成物に関するものである。Accordingly, the present invention relates to a coating composition prepared by adding a silyl isocyanate, an acidic phosphoric acid ester compound or a phosphonic acid compound, and an organic solvent to a full primary corelefin resin having a hydroxyl group.
本発明について詳しく説明すれば、ヒドロキシ基を右す
るフルオロオレフィン系樹脂としてはたとえばテトラク
ロロエチレンとヒト０キシプ［１ピルエーテルの共重合
体、パークロロアルキルアクリレートとにドロキシプロ
ピルエーテルとのへ重゛合体を例として挙げることがで
きる。この樹脂としてはヒドロキシ基の外にパークロロ
アルキル１店或はカルボキシル基やエポキシ基等の官能
基をもつことが望ましく又有礪溶剤に可溶性の重合体で
あることが望ましい。To explain the present invention in detail, examples of the fluoroolefin resin having a hydroxyl group include a copolymer of tetrachloroethylene and human oxypyl ether, a copolymer of perchloroalkyl acrylate and droxypropyl ether, etc. can be cited as an example. This resin preferably has a functional group such as a perchloroalkyl monomer, a carboxyl group, or an epoxy group in addition to the hydroxyl group, and is preferably a polymer soluble in a solvent.
かかるフッ素系樹脂に対して用いられるシリルイソシア
ネートは５ｉ−ＮＧＯ結合を有する一般式 ＲＳ ｌ
（Ｎ Ｃｏ ） ４−ｎ （式中ＲはＣ−１〜１８のア
ルキル、アリール又はアルケニル基を示し、ｎ＝Ｏ〜３
）のシリルイソシアネ−１・やその綜合物や反応物例え
ばメチルシリルトリイソシアネート、ジメチルシリルジ
イソシアネート、トリメチルシリルモノイソシアネート
、ビニルシリルトリイソシアネート、メチルビニルシリ
ルジイソシアネート、フェニルジリルトリイソシアネー
ト、メチシフ１ニルシリルジイソシアネート、ｎ−オク
チルシリルトリイソシアネート、オクタデシルシリルト
リイソシアネートやこれらの縮重合体やエポキシ化合物
との反応物を挙げる事が出来る。The silyl isocyanate used for such a fluororesin has a general formula RS l having a 5i-NGO bond.
(N Co ) 4-n (wherein R represents a C-1-18 alkyl, aryl or alkenyl group, n = O-3
), and their composites and reactants, such as methylsilyl triisocyanate, dimethylsilyl diisocyanate, trimethylsilyl monoisocyanate, vinylsilyl triisocyanate, methylvinylsilyl diisocyanate, phenyldylyl triisocyanate, methysif-1-nylsilyl diisocyanate, Examples include n-octylsilyl triisocyanate, octadecylsilyl triisocyanate, condensation polymers thereof, and reactants with epoxy compounds.
これらは一種単独で又は数種混合して用いられる。These may be used alone or in combination.
更に硬化剤として本発明では酸性リン酸エステル化合物
ないしホスホン酸化合物が一種又は数種用いられる。こ
こで用いられる酸性リン酸エステル化合物は一般式
％式％）
（ここにＲはＣ＝１〜１０のアルキル、アリール、又は
アルケニルを示し、ｎ＝１又は２）で表わされる化合物
であり、一方ホスホン酸化合物は一般式
％式％（）
（Ｒは上記と同じ）で表わされる化合物である。Further, as a curing agent, one or more kinds of acidic phosphoric acid ester compounds or phosphonic acid compounds are used in the present invention. The acidic phosphoric acid ester compound used here is a compound represented by the general formula % (where R represents C=1 to 10 alkyl, aryl, or alkenyl, and n=1 or 2); The phosphonic acid compound is a compound represented by the general formula % (R is the same as above).
酸性リン酸エステル化合物としてはたとえば酸性ブチル
リン酸エステル、酸性ジブチルリン酸エステル、酸性オ
クチルリン酸エステルが挙げられる。又ホスホン酸とし
てはモノ又はジブチルボスホン酸、モノ又はジブチルボ
スホン酸、フにルホスホン酸があげられる。Examples of the acidic phosphate compound include acidic butyl phosphate, acidic dibutyl phosphate, and acidic octyl phosphate. Examples of the phosphonic acid include mono- or dibutylbosphonic acid, mono- or dibutylbosphonic acid, and mono- or dibutylbosphonic acid.
これらフッ素樹脂と硬化剤を溶解する有機溶剤どしては
たとえばトルエン、キシレン、１．１゜２−トリクロ０
１，２．２−トリフルオロエタン、酢酸エチル、酢酸イ
ソプロピル、酢酸ブチル、ジブチルニーアル、メチルエ
チルケトン、メチルイソブチルケトン等を挙げることが
できる。この外溶剤の一成分としてジエチレングリコー
ルジメチルエーテル、トリエチレングリコールジメチル
エーテル、ジエチレングリコールジアセテート、トリエ
チレングリコールジアセテート等のポリアルキレングリ
コールジエーテル又はポリアルキレングリコールジエス
テル等を一種又は数種用いることができ、これらは沈澱
を防ぐ安定化剤としての働きをする。Examples of organic solvents that dissolve these fluororesins and curing agents include toluene, xylene, 1.1゜2-trichloro
Examples include 1,2,2-trifluoroethane, ethyl acetate, isopropyl acetate, butyl acetate, dibutylnial, methyl ethyl ketone, methyl isobutyl ketone, and the like. As a component of this external solvent, one or more types of polyalkylene glycol diethers or polyalkylene glycol diesters such as diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol diacetate, and triethylene glycol diacetate can be used, and these can be used as precipitates. Acts as a stabilizer to prevent
これら各成分から被覆組成物を調製するときの各成分の
ｔ比は期待する物性に対応して選択することができる。When preparing a coating composition from these components, the t ratio of each component can be selected depending on the expected physical properties.
このようにしてえられた組成物は塗Ｍ １１常圧下室温
または低温で短時間に硬化させることができる。従って
本発明の被覆組成物は穏やかな硬化条件で硬化させるこ
とができる。しかもその被膜は透明性、耐薬品性にとみ
、金属、セラミック、ガラス材等に対する付着力も特に
良好である。The composition thus obtained can be cured as a coating M11 under normal pressure at room temperature or at low temperature in a short period of time. Therefore, the coating composition of the present invention can be cured under mild curing conditions. Furthermore, the coating has excellent transparency and chemical resistance, and has particularly good adhesion to metals, ceramics, glass materials, etc.
（実施例−１）
フルオロオレフィンとヒト［１キシアルキルビニルニー
デルとの交互共重合体市販品（ルミフロン ＬＦ−１０
０、旭硝子（株）製、Ｏｌ−１価（ｍｇＫＯＨ／ｇ）２
６）１００部、キシレン１００部、酢酸ブチル１００部
を混合して均一に溶解し、これにメチルシリルトリイソ
シアネート６０部、酸性混合ブチルリン酸ニスデル０．
５部及びジエチレングリコールジメチルエーテル６０部
を加えて溶剤の還流下で４時間反応させ、その後１０℃
以Ｆで１日静δする。生成物をン濾過して無色透明の溶
液を得た。(Example-1) Commercially available alternating copolymer of fluoroolefin and human [1-xyalkylvinyl needle (Lumiflon LF-10)
0, manufactured by Asahi Glass Co., Ltd., Ol-1 value (mgKOH/g)2
6) Mix 100 parts of xylene, 100 parts of butyl acetate and dissolve them uniformly, and add 60 parts of methylsilyl triisocyanate and 0.0 parts of acidic mixed butyl nitride phosphate.
5 parts and 60 parts of diethylene glycol dimethyl ether were added and reacted for 4 hours under reflux of the solvent, and then heated at 10°C.
From then on, it will be quiet for 1 day at F. The product was filtered to obtain a clear colorless solution.
（実施例−２）
（実施例−１）に於いてメチルシリルトリイソシアネー
トの代りにテトラシリルイソシアネートとメチルシリル
トリイソシアネートを同量混合して使用し、ジエチレン
グリコールジメチルエーテルの代りにトリエチレングリ
コールジアセテートを用い同様に処理し、無色透明の溶
液を得た。(Example-2) In (Example-1), the same amounts of tetrasilyl isocyanate and methylsilyl triisocyanate were used instead of methylsilyl triisocyanate, and triethylene glycol diacetate was used instead of diethylene glycol dimethyl ether. A colorless and transparent solution was obtained by treatment in the same manner as before.
（実施例−３）
テトラクロロエチレンとイソブチルビニルエーテル及び
ヒドロキシブチルビニルエーテルをモル比５０：４０：
１０の比率で重合して得たヒドロキシ含有フッ素樹脂５
０部と酢酸ブチル１００部、キシレン１００部を均一に
混合し、これにメチルシリルトリイソシアネート、トリ
メチルシリルモノイソシアネート、テトラシリルイソシ
アネートをｌｆｆ１比で各２０部宛混合し硬化剤として
フェニルホスホンＭ０．５部とトリエチレングリコール
ジメチルエーテル６０部を加え（実施例−１）と同様処
理して無色透明溶液を得た。(Example-3) Tetrachloroethylene, isobutyl vinyl ether, and hydroxybutyl vinyl ether in a molar ratio of 50:40:
Hydroxy-containing fluororesin obtained by polymerization at a ratio of 5 to 10
0 parts, 100 parts of butyl acetate, and 100 parts of xylene were uniformly mixed, and 20 parts each of methylsilyltriisocyanate, trimethylsilyl monoisocyanate, and tetrasilyl isocyanate were mixed in lff1 ratio, and 0.5 parts of phenylphosphophone M was added as a curing agent. and 60 parts of triethylene glycol dimethyl ether were added and treated in the same manner as in Example 1 to obtain a colorless and transparent solution.
（性能例−１）
洗浄したガラス板にロールコ−１−で実施例の各組成物
をコートし２５℃で静置して乾燥させ、物性テストを行
なった。(Performance Example 1) A cleaned glass plate was coated with each of the compositions of the Examples using Roll Coat 1, and then left standing at 25° C. to dry, and a physical property test was conducted.
乾燥時間 付着性＊１ 硬 度＊３ 耐キシレン性＊
３実施例−１２０分 １００／１００ Ｈ〜２Ｈ変
化なし２ ２０分 １００／１００ ２１１〜３Ｉ−１
３４５分 １００／１００ ト１〜２Ｈ１１
１ゴバン目剥頗１テスト
＊２ 鉛筆硬度
本３３０℃４ジレンに２４時間浸漬した旧の外観変化
又６塗装膜は透明であり各試片共透過率の変化減少は２
〜３％であり良好であった。Drying time Adhesion*1 Hardness*3 Xylene resistance*
3 Example - 120 minutes 100/100 H~2H No change 2 20 minutes 100/100 211~3I-1
345 minutes 100/100 To1~2H11
1st goblin 1st test *2 Pencil hardness Book 330℃ 4 Change in appearance of old model after 24 hours immersion in gelatin 6 The paint film is transparent and the change in transmittance of each specimen decreases by 2
~3%, which was good.
本発明に係る被覆組成物は実施例からも明らかなように
常圧、常温で２０〜４５分間Ｐｉ！麿のごく短時間で硬
化する等穏やかな硬化条件で硬化し付着性も良好な被膜
を与えることができ、しかｂ ｉ＋４薬品性、透明性に
°ｂすぐれており、かくて本発明は誠に有効な′ＰＩＩ
ｍ組成物を提供するものである。As is clear from the examples, the coating composition according to the present invention has a Pi! It cures under mild curing conditions, such as curing in a very short time, and can provide a film with good adhesion, and has excellent chemical properties and transparency, and thus the present invention is very effective. na'PII
m composition.
Claims (1)
、シリルイソシアネートと、酸性リン酸エステル化合物
ないしホスホン酸化合物と、有機溶剤とを加えて調製し
てなる被覆組成物。 ２、有機溶剤の一成分としてポリアルキレングリコール
ジエーテルとポリアルキレングリコールジエステルの一
種又は数種を混合してなる特許請求の範囲第１項記載の
被覆組成物。[Claims] 1. A coating composition prepared by adding silyl isocyanate, an acidic phosphoric acid ester compound or a phosphonic acid compound, and an organic solvent to a fluoroolefin resin having a hydroxyl group. 2. The coating composition according to claim 1, which comprises a mixture of one or more types of polyalkylene glycol diether and polyalkylene glycol diester as one component of the organic solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10419086A JPS62260868A (en) | 1986-05-07 | 1986-05-07 | Coating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10419086A JPS62260868A (en) | 1986-05-07 | 1986-05-07 | Coating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62260868A true JPS62260868A (en) | 1987-11-13 |
Family
ID=14374066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10419086A Pending JPS62260868A (en) | 1986-05-07 | 1986-05-07 | Coating composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62260868A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6330571A (en) * | 1986-07-23 | 1988-02-09 | Showa Highpolymer Co Ltd | Moisture curing paint resin composition |
| EP0271876A2 (en) * | 1986-12-19 | 1988-06-22 | Asahi Glass Company Ltd. | Coating composition and coated product |
| JPS63254171A (en) * | 1987-04-10 | 1988-10-20 | Asahi Glass Co Ltd | Coating composition |
| JPS63264675A (en) * | 1986-12-19 | 1988-11-01 | Asahi Glass Co Ltd | Coating composition and painted article |
| US4879345A (en) * | 1988-07-27 | 1989-11-07 | Ppg Industries, Inc. | Fluoropolymer based coating composition for adhesion direct to glass |
| JPH0229449A (en) * | 1988-07-19 | 1990-01-31 | Asahi Glass Co Ltd | Coating composition |
| WO2007033786A1 (en) * | 2005-09-22 | 2007-03-29 | Basf Coatings Ag | Use of phosphonic acid diesters and diphosphonic acid diesters and silane group-containing, curable mixtures containing phosphonic acid diesters and diphosphonic acid diesters |
| US8138249B2 (en) | 2007-03-23 | 2012-03-20 | Basf Coatings Japan Ltd. | Phosphonate-containing two-component coating system and the production and use thereof |
| US9018330B2 (en) | 2006-05-29 | 2015-04-28 | Basf Coatings Gmbh | Use of curable mixtures comprising silane group-containing compounds and phosphonic acid diester or diphosphonic acid diester as adhesives |
| US10294389B2 (en) | 2005-09-22 | 2019-05-21 | Basf Coatings Gmbh | Use of phosphonic acid diesters and diphosphonic acid diesters and thermally curable mixtures containing phosphonic acid diesters and diphosphonic acid diesters |
-
1986
- 1986-05-07 JP JP10419086A patent/JPS62260868A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6330571A (en) * | 1986-07-23 | 1988-02-09 | Showa Highpolymer Co Ltd | Moisture curing paint resin composition |
| EP0271876A2 (en) * | 1986-12-19 | 1988-06-22 | Asahi Glass Company Ltd. | Coating composition and coated product |
| JPS63264675A (en) * | 1986-12-19 | 1988-11-01 | Asahi Glass Co Ltd | Coating composition and painted article |
| JPS63254171A (en) * | 1987-04-10 | 1988-10-20 | Asahi Glass Co Ltd | Coating composition |
| JPH0229449A (en) * | 1988-07-19 | 1990-01-31 | Asahi Glass Co Ltd | Coating composition |
| US4879345A (en) * | 1988-07-27 | 1989-11-07 | Ppg Industries, Inc. | Fluoropolymer based coating composition for adhesion direct to glass |
| WO2007033786A1 (en) * | 2005-09-22 | 2007-03-29 | Basf Coatings Ag | Use of phosphonic acid diesters and diphosphonic acid diesters and silane group-containing, curable mixtures containing phosphonic acid diesters and diphosphonic acid diesters |
| US8013099B2 (en) | 2005-09-22 | 2011-09-06 | Basf Coatings Ag | Use of phosphonic acid diesters and diphosphonic acid diesters and silane group containing, curable mixtures containing phosphonic acid diesters and diphosphonic acid diesters |
| KR101320004B1 (en) * | 2005-09-22 | 2013-10-22 | 바스프 코팅스 게엠베하 | Use of phosphonic acid diesters and diphosphonic acid diesters and silane group-containing, curable mixtures containing phosphonic acid diesters and diphosphonic acid diesters |
| US10294389B2 (en) | 2005-09-22 | 2019-05-21 | Basf Coatings Gmbh | Use of phosphonic acid diesters and diphosphonic acid diesters and thermally curable mixtures containing phosphonic acid diesters and diphosphonic acid diesters |
| US9018330B2 (en) | 2006-05-29 | 2015-04-28 | Basf Coatings Gmbh | Use of curable mixtures comprising silane group-containing compounds and phosphonic acid diester or diphosphonic acid diester as adhesives |
| US8138249B2 (en) | 2007-03-23 | 2012-03-20 | Basf Coatings Japan Ltd. | Phosphonate-containing two-component coating system and the production and use thereof |
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