JP2010144123A - ポリエステル(メタ)アクリレート樹脂組成物、塗布構造体及びその施工方法 - Google Patents
ポリエステル(メタ)アクリレート樹脂組成物、塗布構造体及びその施工方法 Download PDFInfo
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- JP2010144123A JP2010144123A JP2008325413A JP2008325413A JP2010144123A JP 2010144123 A JP2010144123 A JP 2010144123A JP 2008325413 A JP2008325413 A JP 2008325413A JP 2008325413 A JP2008325413 A JP 2008325413A JP 2010144123 A JP2010144123 A JP 2010144123A
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- meth
- polyester
- acrylate
- acrylate resin
- resin composition
- Prior art date
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- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 47
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 15
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 14
- 238000010276 construction Methods 0.000 claims abstract description 11
- 239000007921 spray Substances 0.000 claims abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 25
- 238000002156 mixing Methods 0.000 claims description 5
- 238000005507 spraying Methods 0.000 claims description 4
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- -1 alicyclic alcohol compound Chemical class 0.000 description 25
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- 150000001875 compounds Chemical class 0.000 description 18
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- 230000015572 biosynthetic process Effects 0.000 description 9
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- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
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- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000001361 adipic acid Substances 0.000 description 8
- 235000011037 adipic acid Nutrition 0.000 description 8
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- 239000011261 inert gas Substances 0.000 description 8
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- 238000007605 air drying Methods 0.000 description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 6
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- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- 229920006395 saturated elastomer Polymers 0.000 description 5
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- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
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- 125000000524 functional group Chemical group 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
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- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000007519 polyprotic acids Polymers 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 2
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
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- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
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Landscapes
- Application Of Or Painting With Fluid Materials (AREA)
- Polyesters Or Polycarbonates (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
【解決手段】 本発明は、ポリエステル(メタ)アクリレート樹脂(A)、ジシクロペンテニルオキシエチル(メタ)アクリレート(B)を含むポリエステル(メタ)アクリレート樹脂組成物において、前記ポリエステル(メタ)アクリレート樹脂(A)が、そのポリエステル構造の酸成分として、脂環式二塩基酸(A1)及び/又は脂肪族二塩基酸(A2)を40モル%以上使用するものであることを特徴とするポリエステル(メタ)アクリレート樹脂組成物を提供する。
【選択図】 なし
Description
前記ポリエステル(メタ)アクリレート樹脂(A)が、そのポリエステル構造の酸成分として、脂環式二塩基酸(A1)及び/又は脂肪族二塩基酸(A2)を40モル%以上使用するものであることを特徴とするポリエステル(メタ)アクリレート樹脂組成物に関する。
また、ジビニルベンゼン、ジアリルフタレート、ジアリルイソフタレート、ジアリルテトラブロムフタレート、トリアリルフタレート等も、発明の効果を損なわない範囲で使用することができる。
その際添加されるオキシム化合物とは、例えば、メチルエチルケトンオキシムであり、その添加量は、前記(A)と(B)からなる樹脂組成物100質量部に0.01以上1質量部未満である。好ましくは0.02〜0.8質量部である。この範囲を外れると長期保存安定性が得られないものとなる。また、コバルト石鹸(C)とオキシム化合物(D)との質量比は、1:0.01〜1:1であることが好ましく、より好ましくは1:0.08〜1:0.75である。この範囲を外れると長期保存安定性が得られないものとなる。
前記ラジカル硬化剤の使用量は、樹脂組成物の合計量100質量部に対して、0.1〜6質量部であることが好ましい。
アジピン酸3モル、ジエチレングリコール2モルを温度計、攪拌機、不活性ガス導入口および還流冷却器を備えた四口フラスコに仕込み、エステル化触媒としてモノブチルチンオキサイドを0.5重量%添加し、205℃で11時間反応させた。その後、140℃まで冷却し、次いでグリシジルメタクリレート2モルを投入し、10時間反応させ、ポリエステルメタアクリレート樹脂(A)を得た。
アジピン酸1.2モル、無水フタル酸1.8モル、ジエチレングリコール2モルを温度計、攪拌機、不活性ガス導入口および還流冷却器を備えた四口フラスコに仕込み、エステル化触媒としてモノブチルチンオキサイドを0.5重量%添加し、205℃で11時間反応させた。その後、140℃まで冷却し、次いでグリシジルメタクリレート2モルを投入し、10時間反応させ、ポリエステルメタアクリレート樹脂(B)を得た。
アジピン酸2モル、ヘキサヒドロ無水フタル酸1モル、ネオペンチルグリコール2モルを温度計、攪拌機、不活性ガス導入口および還流冷却器を備えた四口フラスコに仕込み、エステル化触媒としてモノブチルチンオキサイドを0.5重量%添加し、205℃で11時間反応させた。その後、140℃まで冷却し、次いでグリシジルメタクリレート2モルを投入し、10時間反応させ、ポリエステルメタアクリレート樹脂(C)を得た。
アジピン酸2モル、メチルテトラヒドロ無水フタル酸1モル、ネオペンチルグリコール2モルを温度計、攪拌機、不活性ガス導入口および還流冷却器を備えた四口フラスコに仕込み、エステル化触媒としてモノブチルチンオキサイドを0.5重量%添加し、205℃で11時間反応させた。その後、140℃まで冷却し、次いでグリシジルメタクリレート2モルを投入し、10時間反応させ、ポリエステルメタアクリレート樹脂(D)を得た。
合成例1〜4で得られたポリエステルメタアクリレート樹脂(A)〜(D)を用いて、以下の相溶性試験を行った。
(相溶性試験方法)
ポリエステルメタアクリレート樹脂(A)〜(D)とジシクロペンテニルオキシエチルメタクリレートを混合比率60/40、50/50、40/60にて、60℃で加温混合した後、室温25℃まで冷却し、目視で濁りの有無を確認する。
良:25℃目視で透明か否か確認する。
悪:25℃目視で濁っているか否か確認する。
○:範囲内
×:範囲外
アジピン酸0.9モル、無水フタル酸2.1モル、ジエチレングリコール2モルを温度計、攪拌機、不活性ガス導入口および還流冷却器を備えた四口フラスコに仕込み、エステル化触媒としてモノブチルチンオキサイドを0.5重量%添加し、205℃で11時間反応させた。その後、140℃まで冷却し、次いでグリシジルメタクリレート2モルを投入し、10時間反応させ、ポリエステルメタアクリレート(a)を得た。
アジピン酸0.6モル、無水フタル酸2.4モル、ジエチレングリコール2モルを温度計、攪拌機、不活性ガス導入口および還流冷却器を備えた四口フラスコに仕込み、エステル化触媒としてモノブチルチンオキサイドを0.5重量%添加し、205℃で11時間反応させた。その後、140℃まで冷却し、次いでグリシジルメタクリレート2モルを投入し、10時間反応させ、ポリエステルメタアクリレート(b)を得た。
アジピン酸0.3モル、無水フタル酸2.7モル、ジエチレングリコール2モルを温度計、攪拌機、不活性ガス導入口および還流冷却器を備えた四口フラスコに仕込み、エステル化触媒としてモノブチルチンオキサイドを0.5重量%添加し、205℃で11時間反応させた。その後、140℃まで冷却し、次いでグリシジルメタクリレート2モルを投入し、10時間反応させ、ポリエステルメタアクリレート(c)を得た。
無水フタル酸3モル、ジエチレングリコール2モルを温度計、攪拌機、不活性ガス導入口および還流冷却器を備えた四口フラスコに仕込み、エステル化触媒としてモノブチルチンオキサイドを0.5重量%添加し、205℃で11時間反応させた。その後、140℃まで冷却し、次いでグリシジルメタクリレート2モルを投入し、10時間反応させ、ポリエステルメタアクリレート(d)を得た。
良:25℃目視で透明か否か確認する。
悪:25℃目視で濁っているか否か確認する。
○:範囲内
×:範囲外
Claims (5)
- ポリエステル(メタ)アクリレート樹脂(A)、ジシクロペンテニル(メタ)アクリレート(B)を含むポリエステル(メタ)アクリレート樹脂組成物において、
前記ポリエステル(メタ)アクリレート樹脂(A)が、そのポリエステル構造の酸成分として、脂環式二塩基酸(A1)及び/又は脂肪族二塩基酸(A2)を40モル%以上使用するものであることを特徴とするポリエステル(メタ)アクリレート樹脂組成物。 - 前記ポリエステル(メタ)アクリレート樹脂(A)が60〜30質量%で、前記ジシクロペンテニル(メタ)アクリレート(B)が40〜70質量%である請求項1記載のポリエステル(メタ)アクリレート樹脂組成物。
- 前記ポリエステル(メタ)アクリレート樹脂(A)の脂環式二塩基酸(A1)及び脂肪族二塩基酸(A2)の混合質量割合が、90〜10:10〜90(質量部)のいずれかである請求項1記載のポリエステル(メタ)アクリレート樹脂組成物。
- 請求項1〜3いずれか1項に記載のポリエステル(メタ)アクリレート樹脂組成物をスプレー塗布したことを特徴とする塗布構造物。
- 請求項1〜3いずれか1項に記載のポリエステル(メタ)アクリレート樹脂組成物を土木建築構造体にスプレーすることを特徴とする施工方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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DE624609C (de) * | 1936-01-24 | Johannes Jacobsen | Verfahren und Strahlrohr zum Spritzen von Gasen, insbesondere Feuerloeschgasen | |
JPS56152877A (en) * | 1980-04-30 | 1981-11-26 | Mitsubishi Petrochem Co Ltd | Photocurable coating composition |
EP0624609A2 (de) * | 1993-05-12 | 1994-11-17 | BASF Aktiengesellschaft | Emissionsarme ungesättigte Polyesterharze |
JPH09290567A (ja) * | 1996-02-28 | 1997-11-11 | Nippon Kayaku Co Ltd | 液状組成物、レーザーマーキング用物品及びマーキング方法 |
JP2005154688A (ja) * | 2003-11-28 | 2005-06-16 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物 |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE624609C (de) * | 1936-01-24 | Johannes Jacobsen | Verfahren und Strahlrohr zum Spritzen von Gasen, insbesondere Feuerloeschgasen | |
JPS56152877A (en) * | 1980-04-30 | 1981-11-26 | Mitsubishi Petrochem Co Ltd | Photocurable coating composition |
EP0624609A2 (de) * | 1993-05-12 | 1994-11-17 | BASF Aktiengesellschaft | Emissionsarme ungesättigte Polyesterharze |
JPH09290567A (ja) * | 1996-02-28 | 1997-11-11 | Nippon Kayaku Co Ltd | 液状組成物、レーザーマーキング用物品及びマーキング方法 |
JP2005154688A (ja) * | 2003-11-28 | 2005-06-16 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物 |
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