JP4876580B2 - 含フッ素エラストマー塗料組成物 - Google Patents
含フッ素エラストマー塗料組成物 Download PDFInfo
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- JP4876580B2 JP4876580B2 JP2005515627A JP2005515627A JP4876580B2 JP 4876580 B2 JP4876580 B2 JP 4876580B2 JP 2005515627 A JP2005515627 A JP 2005515627A JP 2005515627 A JP2005515627 A JP 2005515627A JP 4876580 B2 JP4876580 B2 JP 4876580B2
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- Prior art keywords
- fluorine
- group
- crosslinking
- coating
- coating composition
- Prior art date
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229920006169 Perfluoroelastomer Polymers 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
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- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000005468 ion implantation Methods 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- GRPIQKZLNSCFTB-UHFFFAOYSA-N n-[bis(dimethylamino)-fluoroimino-$l^{5}-phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(=NF)(N(C)C)N(C)C GRPIQKZLNSCFTB-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- SANRKQGLYCLAFE-UHFFFAOYSA-H uranium hexafluoride Chemical compound F[U](F)(F)(F)(F)F SANRKQGLYCLAFE-UHFFFAOYSA-H 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
- C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
Description
化合物(A)は、架橋構造を形成するために一般式(1):
含フッ素エラストマー(B)は、一般式(1)で示される架橋性反応基と反応可能な架橋部位を有するものであればよく、特に限定されるものではない。
CF2=CFO(CF2CF(CF3)O)m(CF2)n−X1 (4)
(式中、mは、0〜5の整数、nは、1〜3の整数、X1は、シアノ基、カルボキシル基、アルコキシカルボニル基)で表される単量体などがあげられ、これらをそれぞれ単独で、または任意に組合わせて用いることができる。
CF2=CFO(CF2CFY2O)p−(CF2CF2CF2O)q−Rf 1 (5)
(式中、Y2は、FまたはCF3、Rf 1は、炭素数1〜5のパーフルオロアルキル基、pは、0〜5の整数、qは、0〜5の整数)で表されるパーフルオロビニルエーテルなどがあげられる。
CF2=CF(CF2)rX2 (6)
(式中、rは、1〜10の整数、X2は、フッ素原子または塩素原子)で表される化合物、パーフルオロ−2−ブテンなどのパーハロオレフィンなどがあげられる。
CF2=CF−Rf 2 (7)
(式中、Rf 2は、Rf 3または−ORf 3であり、Rf 3は、炭素数1〜5のパーフルオロアルキル基)で表される化合物0〜15モル%からなる非エラストマー性ポリマー鎖があげられる。
CH2=CX3−(CF2)s−X3 (8)
(式中、X3は、水素原子またはフッ素原子、sは、1〜10の整数)で表される化合物、CH2=C(CF3)2などの部分フッ素化オレフィンなどがあげられる。
本発明に使用される含フッ素エラストマー(B)は、常法により製造することができ、乳化重合法、懸濁重合法、溶液重合法などの重合法により製造することができる。重合時の温度、時間などの重合条件としては、モノマーの種類や目的とするエラストマーにより適宜決定すればよい。
本発明に使用できる溶剤としては、特に限定されず、含フッ素エラストマーを充分にとかすことができるものであればよい。また、含フッ素エラストマーとして、パーフルオロエラストマーを使用する場合は、パーフルオロエラストマーを充分にとかすことができる点で、化学構造から計算される水素濃度が3%以下のフッ素系溶剤が好ましく、水素濃度が0%である完全フッ素化溶剤がより好ましい。水素濃度が3%をこえる溶剤であると、パーフオロエラストマーの溶解性に乏しい傾向がある。
本発明の塗料組成物は、溶剤以外の各成分を、通常のゴム用加工機械、たとえば、オープンロール、バンバリーミキサー、ニーダーなどを用いて混合し、コンパウンドとした後、溶剤に溶解または分散させることにより調製することができる。この他、ボールミル等の密閉式混合機を用い、各成分を混合する方法によっても調製することができる。
着火源をもたない内容積3mLのステンレススチール製オートクレーブに、純水1Lおよび乳化剤として
内容積1Lの電磁攪拌式ガラスオートクレーブに、純水500ミリリットルおよび乳化剤として
製造例1で得られたシアノ基含有する含フッ素エラストマーとジャーナル・オブ・ポリマー・サイエンスのポリマー・ケミストリー編、Vol.20、2381〜2393頁(1982)に記載の方法で合成した架橋剤である2,2−ビス[3−アミノ−4−(N−フェニルアミノ)フェニル]ヘキサフルオロプロパン(AFTA−Ph)とカーボンブラック(Cancarb社製 Thermax N−990)とを重量比100/0.8/20(重量部)で、オープンロールにて混合した後に、パーフロ溶剤であるフロリナートFC−77(登録商標、住友スリーエム株式会社製、主成分:C8F16O)に溶解させ、固形分濃度が10重量%の塗料組成物を調整した。
得られた塗装膜をフロリナートFC−77(登録商標、住友スリーエム株式会社製、主成分:C8F16O)に40℃で24時間浸漬し、表面状態を目視で観察し、以下の基準により評価した。
○:溶解しなかった。
△:塗膜の表面部分が溶解した。
×:塗膜がほぼ完全に溶解した。
得られた塗装膜をフロリナートFC−77(登録商標、住友スリーエム株式会社製、主成分:C8F16O)に40℃で24時間浸漬した後の液の状態(色、にごり具合)を目視で観察し、以下の基準により評価した。
○:無色透明であり、変化はなかった(塗膜の溶解、カーボンブラックの脱落はない)。
△:黒い浮遊物があった(塗膜の溶解によるカーボンブラックの脱落が少ない)。
×:液が真っ黒になった(塗膜の溶解によるカーボンブラックの脱落が多い)。
製造例2で得られた末端にヨウ素を含有する含フッ素エラストマーと、パーヘキサ25B(日本油脂(株)製)とトリアリルイソシアヌレート(TAIC)(日本化成(株)製)とカーボンブラック(Cancarb社製 Thermax N−990)とを重量比100/1/3/20(重量部)で、オープンロールにて混合した後に、パーフロ溶剤であるフロリナートFC−77(登録商標、住友スリーエム株式会社製、主成分:C8F16O)に溶解させ、固形分濃度を10重量%の塗料組成物を調整した以外は、実施例1と同様にして、塗装板を得た。
200℃で10分間焼成を行うかわりに、スチーム加硫缶中にて150℃で60分間加熱した以外は、比較例1と同様にして、塗装板を得た。
ポリオール系架橋剤含有の含フッ素エラストマー(ダイエルG−701、ダイキン工業株式会社製)、酸化マグネシウム(MA−150、協和化学工業株式会社製)、水酸化カルシウム(CALDIC#2000、近江化学工業株式会社製)、MTカーボンブラック(N990、Cancarb LTD.製)とを重量比100/3/6/20(重量部)で、オープンロールにて混練し、架橋可能なフッ素ゴム組成物を得た。
比較例3で得られたフッ素ゴムシートの表面に、実施例1で作製した塗料組成物を刷毛で塗布し、30分風乾した後、80〜100℃に設定したオーブンで30分間乾燥し、さらに、その後、200℃で10分間焼成を行った。この操作を3回繰り返した後、さらに、230℃で5時間の焼成を行い、表面が完全に塗膜で覆われたフッ素ゴムシートを得た。
Claims (3)
- (A)一般式(1):
(B)シアノ基、カルボキシル基およびアルコキシカルボニル基からなる群から選択される少なくとも1つの基からなる架橋部位を有するパーフルオロエラストマー、および
(C)完全フッ素化溶剤
からなる含フッ素エラストマー塗料組成物。 - 請求の範囲第1項記載の含フッ素エラストマー塗料組成物を空気中で架橋することにより得られる塗膜。
- 金属、樹脂、ゴムまたはそれらの複合体からなる物品の一部または全面に、請求の範囲第1項記載の塗料組成物からなる塗膜を有する塗装物品。
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JP2005515627A JP4876580B2 (ja) | 2003-11-21 | 2004-11-17 | 含フッ素エラストマー塗料組成物 |
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JP2003392174 | 2003-11-21 | ||
JP2005515627A JP4876580B2 (ja) | 2003-11-21 | 2004-11-17 | 含フッ素エラストマー塗料組成物 |
PCT/JP2004/017086 WO2005049746A1 (ja) | 2003-11-21 | 2004-11-17 | 含フッ素エラストマー塗料組成物 |
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JPWO2005049746A1 JPWO2005049746A1 (ja) | 2007-11-29 |
JP4876580B2 true JP4876580B2 (ja) | 2012-02-15 |
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Cited By (1)
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US20190118221A1 (en) * | 2017-10-24 | 2019-04-25 | The Boeing Company | Conformal fluoropolymer coatings |
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US20090018275A1 (en) * | 2007-01-26 | 2009-01-15 | Greene, Tweed Of Delaware, Inc. | Method of Bonding Perfluoroelastomeric Materials to a Surface |
JP2008296549A (ja) * | 2007-06-04 | 2008-12-11 | Daikin Ind Ltd | パーフルオロエラストマー塗膜を有するフッ素樹脂成形品 |
JP5711870B2 (ja) * | 2008-11-05 | 2015-05-07 | 株式会社森清化工 | 封止材 |
JP2011086920A (ja) | 2009-10-14 | 2011-04-28 | Greene Tweed Of Delaware Inc | プラズマ耐性に優れた処理装置 |
WO2014167797A1 (ja) * | 2013-04-09 | 2014-10-16 | ニチアス株式会社 | 架橋フルオロエラストマーの製造方法 |
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US11712716B2 (en) | 2017-10-24 | 2023-08-01 | The Boeing Company | Conformal fluoropolymer coatings |
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WO2005049746A1 (ja) | 2005-06-02 |
JPWO2005049746A1 (ja) | 2007-11-29 |
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