JP2005154625A - ゲルコート組成物 - Google Patents
ゲルコート組成物 Download PDFInfo
- Publication number
- JP2005154625A JP2005154625A JP2003397017A JP2003397017A JP2005154625A JP 2005154625 A JP2005154625 A JP 2005154625A JP 2003397017 A JP2003397017 A JP 2003397017A JP 2003397017 A JP2003397017 A JP 2003397017A JP 2005154625 A JP2005154625 A JP 2005154625A
- Authority
- JP
- Japan
- Prior art keywords
- group
- gel coat
- compound
- meth
- coat composition
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- -1 peroxide compound Chemical class 0.000 claims abstract description 43
- 229920005989 resin Polymers 0.000 claims abstract description 37
- 239000011347 resin Substances 0.000 claims abstract description 37
- 125000000524 functional group Chemical group 0.000 claims abstract description 21
- 239000004202 carbamide Substances 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000013008 thixotropic agent Substances 0.000 claims description 7
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 81
- 238000010526 radical polymerization reaction Methods 0.000 abstract description 3
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
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- 150000007513 acids Chemical class 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 4
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
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- 230000002000 scavenging effect Effects 0.000 description 4
- 229940058015 1,3-butylene glycol Drugs 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
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- 238000011156 evaluation Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
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- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
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- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 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
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical class C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Macromonomer-Based Addition Polymer (AREA)
Abstract
【解決手段】 1分子中にエチレン性不飽和二重結合を有する樹脂(A)と、エチレン性不飽和二重結合を有する単量体(B)と、分子中にヒドラゾ基、尿素結合又はウレタン結合のいずれかの官能基を有する化合物、β−ジケトン化合物等及びパーオキサイド化合物からなる群から選ばれる少なくとも1種の化合物(C)とを含有してなるゲルコート組成物に関する。
【選択図】 なし
Description
このラジカル重合性樹脂は、ガラスマット、ガラスロービングマット等の所謂繊維強化材と共に積層せしめて得られる繊維強化プラスチックとして、繊維強化プラスチック成形品の様々な用途に用いられている。
このゲルコート層は、繊維強化プラスチック成形品の性能及び外観品質を向上するため、繊維強化プラスチック成形品の最外面に通常300μm〜500μmの厚みで塗布されており、様々な機能性を持たせるには有利な成形手段となっている。
これらゲルコート組成物によって被覆された繊維強化プラスチック成形品として、防水パン、浴槽、カウンター、仕切板、壁材、車両部材、室内部材等、室内外用途含め、幅広く用いられている。
しかしながら、かかるラジカル硬化性樹脂を重合硬化させる際にホルムアルデヒドが発生することが知られており(例えば非特許文献1参照)、ゲルコート層からもホルムアルデヒドが発生する場合がある。
Stanford Research Institute Volume1 Number 7 July,1968; Frank R. Mayo
本発明に使用する1分子中にエチレン性不飽和二重結合を有するラジカル重合性樹脂(A)[以下ラジカル硬化性樹脂(A)という]としては、例えば、不飽和ポリエステル、エポキシ(メタ)アクリレート、ウレタン(メタ)アクリレート、ポリエステル(メタ)アクリレート等が挙げられる。これらの樹脂の数平均分子量は300より大きいものであり、樹脂硬化物の物性の点で、500〜5000のものが好ましい。これらの樹脂は単独で使用しても良いし、必要に応じ2種以上併用しても良い。
エポキシ樹脂は、例えばビスフェノール・タイプのエポキシ樹脂、ノボラックタイプのエポキシ樹脂等が挙げられる。これらのエポキシ樹脂の単独、または両者を混合したものなどである。かかるエポキシ樹脂の平均エポキシ当量が、150〜450なる範囲内のものが好ましい。
また、上記ノボラックタイプのエポキシ樹脂として代表的なものは、フェノールノボラック又はクレゾールノボラックと、エピクロルヒドリン又はメチルエピクロルヒドリンとの反応により得られるエポキシ樹脂などがある。
前記ポリオールとしては、例えばポリプロピレンオキシド、ポリエチレンオキシド、ポリテトラメチレングリコール、ビスフェノールAエチレンオキシド付加物、ビスフェノールAプロピレンオキシド付加物等のポリエーテルポリオール、ポリブタジエンジオール、ポリイソプレンジオール、ポリエステルエーテルポリオール、ポリエステルポリオール等が挙げられる。
R7−NH−Y (3)
R7がアルキル基であり、かつYが−CO−NH−を含む1価の官能基である一般式(1)で表される化合物(C)としては、例えば尿素、モノメチル尿素、モノメチロール尿素、ジメチロール尿素、ジメチル尿素、ジフェニル尿素、メチレン尿素、エチレン尿素、プロピレン尿素、アルコシキメチル尿素等が挙げられる。これらのうち、ホルムアルデヒド捕捉効果の大きい点でエチレン尿素が好ましい。
さらにR7がウレタン結合を有する1価の官能基であり、かつYが−COO−を含む1価の官能基を有する化合物(C)としては、ウレタン(メタ)アクリレート等のビニルウレタン化合物等が挙げられる。
重合禁止剤としては、例えばトリハイドロベンゼン、トルハイドロキノン、14−ナフトキノン、パラベンゾキノン、ハイドロキノン、ベンゾキノン、ハイドロキノンモノメチルエーテル、p−tert−ブチルカテコール、2,6−ジ−tert−ブチル−4−メチルフェノール等を挙げることができる。重合禁止剤の添加量は、本発明に用いられる樹脂に対して10〜1000ppm添加するのが好ましく、50〜200ppm添加するのがさらに好ましい。かかる範囲で使用することで貯蔵安定性、作業性、強度発現性の優れた樹脂組成物を得ることができる。
また、本発明によるゲルコート組成物の粘度は、好ましくは5〜100dPa.s、より好ましくは粘度10〜40dPa.s(JIS−K−6901 4、5)であり、その揺変性は、好ましくは2.0〜9.0、より好ましくは4.0〜7.0(JIS−K−6901 4、5)であり、これらの粘度及び揺変性が、この範囲であるとスプレーによる吹きつけが容易である。
ゲルコート組成物により形成されるゲルコート層は、成形品の加色性、意匠性を付与させる効果があり、通常有機顔料、無機顔料を添加し用い、所謂、着色ゲルコートとして用いることが多い。顔料は耐熱性に優れ、樹脂の硬化を阻害するものでないものが好ましい。
(参考例1) 不飽和ポリエステルの調製
窒素ガス導入管、還流コンデンサ、攪拌機を備えた2Lのガラス製フラスコに、プロピレングリコール304部、無水マレイン酸196部、無水フタル酸296部を仕込み、窒素気流下、加熱を開始した。内温200℃にて、常法にて脱水縮合反応を行い、ガードナー粘度がQ〜R(樹脂固形分/スチレン=70/30重量比率で希釈し樹脂の縮合度を確認)、酸価が24KOHmg/gになったところで、180℃まで冷却し、トルハイドロキノン、ターシャリブチルカテコールを添加した。さらに150℃まで冷却し、不飽和ポリエステルを得た。これをスチレンで希釈溶解させ、不飽和ポリエステルを得た。以下この不飽和ポリエステルをラジカル硬化性樹脂(1)という。
窒素ガス導入管、還流コンデンサ、攪拌機を備えた2Lのガラス製フラスコに、プロピレングリコール304部、ネオペンチルグリコール88部、イソフタル酸166部仕込み、窒素気流下、加熱を開始した。内温210℃にて、常法にて脱水縮合反応を行い、ソリッド酸価が5KOHmg/gになるまで反応を行った。その後、樹脂温度を180℃まで冷却し、無水マレイン酸1.0モルを同フラスコに仕込み、同様に窒素気流下、加熱を開始し、内温200℃にて、常法にて脱水縮合反応を行い、ガードナー粘度がQ〜R(樹脂固形分/スチレン=70/30重量比率で希釈し樹脂の縮合度を確認)、酸価が15KOHmg/gになったところで、180℃まで冷却し、トルハイドロキノン、ターシャリブチルカテコールを添加し、さらに150℃まで冷却し、不飽和ポリエステルを得た。この不飽和ポリエステルをスチレンで希釈溶解させた。以下この不飽和ポリエステルをラジカル硬化性樹脂(2)という。
ラジカル硬化性樹脂(1)100部に、レオロシールQS−20L(チキソ性付与剤、(株)トクヤマ製)3部添加し、分散撹拌機にて撹拌混合し、エチレン尿素[以下捕捉剤(1)という]を0.2部添加(メタノールに加熱溶解添加)し、スチレンにて、粘度調整を行った。粘度23dPa・s、揺変度5.4のゲルコート組成物を得た。このゲルコート組成物100部に対し、6%ナフテン酸コバルト0.5部添加混合し、パーメックN(硬化剤、日本油脂(株)製)1.0部を加え混合し、カップガンスプレー機(岩田塗装機(株)製スプレーガンW−77(φ2.5mm))を用い、アルミ板(150×150mm)にゲルコートウエット厚さ0.5mmで、吹き付け塗布した。ゲル化した後、50℃の乾燥機にて30分間、後硬化させた。再び室温にて24時間放置し、ゲルコート層を作製し、後述する方法にてホルムアルデヒド放散量の測定、評価を行った。
ラジカル硬化性樹脂(1)の代わりにラジカル硬化性樹脂(2)を用いた以外は、実施例1と同様にしてゲルコート層を作製し、実施例1と同様に評価した。
(実施例3)
ラジカル硬化性樹脂(1)100部に対し、硬化剤としてパーメックN1.0部を用い、トリゴノックス40(アセチルアセトンパーオキサイド、化薬アクゾ社製)[以下捕捉剤(2)という]を1.0部用いた以外は、実施例1と同様にしてゲルコート層を作製し、実施例1と同様に評価した。
エチレン尿素の代わりに、アセトアセトキシエチルメタクリレート[以下捕捉剤(3)という]を2部用いた以外は、実施例1と同様にしてゲルコート層を作製し、実施例1と同様に評価した。
実施例1のゲルコート組成物にホルムアルデヒド捕捉剤としての化合物(C)を添加しない以外は、実施例1と同様に、ゲルコート層を作製し、ホルムアルデヒド放散量の評価を行った。
(比較例2)
実施例2のゲルコート組成物にホルムアルデヒド捕捉剤としての化合物(C)を添加しない以外は、実施例2と同様に、ゲルコート層を作製し、ホルムアルデヒド放散量の評価を行った。
測定方法及び評価基準は以下のとおりである。
<硬化性評価>
硬化性は、ゲルコート層のゲルタイムの延長の有無により評価した。
容量100mlのデスカップに各実施例で得られたゲルコート組成物を50g計量し、これに6%ナフテン酸コバルトを添加して25℃温度に調整した後、パーメックN[メチルエチルケトンパーオキサイド(日本油脂社製)]を混合添加した。これを25℃の恒温槽に浸漬し、ゲルが発生して攪拌棒から樹脂が糸切れ状態になるまでの時間をゲルタイムとした。ホルムアルデヒド捕捉剤を含まない樹脂である比較例1におけるゲルタイムに比較して、ゲルタイムの延長、あるいは硬化した後の硬化物の状態変化の有無を確認した。著しいゲルタイムの延長がないものを「〇」とした。
前記実施例で得られた150mm×150mmのゲルコート層付アルミ板(厚さ3mm)を試験片として、室温(23℃)、湿度50%の環境試験室内(4m×4m×2m)で、24時間放置し、1日後のホルムアルデヒドの揮散量を測定した。測定法は、JIS K 5601−4−1デシケーター法に準じて行い、アルミ板の表面積により、測定値を除し、mg/リッターを単位として算出した。
Claims (5)
- 1分子中にエチレン性不飽和二重結合を有する樹脂(A)と、エチレン性不飽和二重結合を有する単量体(B)と、分子中にヒドラゾ基、尿素結合又はウレタン結合のいずれかの官能基を有する化合物、一般式(1)で表される化合物及び一般式(2)で表される化合物からなる群から選ばれる少なくとも1種の化合物(C)と、チキソ性付与材(D)とを含有してなるゲルコート組成物。
- 前記ヒドラゾ基、尿素結合又はウレタン結合のいずれかの官能基を有する化合物が、一般式(3)で表される化合物である請求項1記載のゲルコート組成物。
R7−NH−Y (3)
(式中、R7は、水素原子、アルキル基、アルケニル基、アルキニル基、ヒドロキシル基で置換されたアルキル基、アミノ基で置換されたアルキル基、アルコキシ基で置換されたアルキル基、アミノ基、フェニル基、カルボキシル基、ウレタン結合を有する1価の官能基及び−NHNH−R8を表す。Yは−NH−、−CO−NH−及び−COO−を含む1価の官能基を表す。但しR8は、水素原子又はアルキル基である。また、R7とYとは結合して環を形成していてもよい。) - 前記一般式(1)で表される化合物が、アセトアセトキシエチルアクリレートである請求項1記載のゲルコート組成物。
- 前記一般式(2)で表される化合物が、アセチルアセトンパーオキサイドである請求項1記載のゲルコート組成物。
- 前記一般式(3)で表される化合物が、エチレン尿素である請求項2記載のゲルコート組成物。
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US11014066B2 (en) | 2015-12-15 | 2021-05-25 | Awi Licensing Llc | VOC and odor reducing coating composition |
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