TWI237052B - Radiation curable powder coating compositions - Google Patents
Radiation curable powder coating compositions Download PDFInfo
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- TWI237052B TWI237052B TW91115426A TW91115426A TWI237052B TW I237052 B TWI237052 B TW I237052B TW 91115426 A TW91115426 A TW 91115426A TW 91115426 A TW91115426 A TW 91115426A TW I237052 B TWI237052 B TW I237052B
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- 239000000843 powder Substances 0.000 title claims abstract description 55
- 239000008199 coating composition Substances 0.000 title claims abstract description 26
- 230000005855 radiation Effects 0.000 title claims abstract description 13
- 229920000728 polyester Polymers 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 238000000576 coating method Methods 0.000 claims abstract description 36
- 239000000178 monomer Substances 0.000 claims abstract description 35
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 31
- -1 acrylfluorenyl groups Chemical group 0.000 claims description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 29
- 239000011248 coating agent Substances 0.000 claims description 27
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 26
- SCWNYUDYCSFNTK-UHFFFAOYSA-N 1-(9h-fluoren-1-yl)prop-2-en-1-one Chemical compound C1C2=CC=CC=C2C2=C1C(C(=O)C=C)=CC=C2 SCWNYUDYCSFNTK-UHFFFAOYSA-N 0.000 claims description 23
- 229920006243 acrylic copolymer Polymers 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000004814 polyurethane Substances 0.000 claims description 18
- 229920002635 polyurethane Polymers 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 239000003973 paint Substances 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 15
- 150000003077 polyols Chemical class 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
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- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 230000007704 transition Effects 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
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- 238000010894 electron beam technology Methods 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 230000009477 glass transition Effects 0.000 claims description 5
- 239000004922 lacquer Substances 0.000 claims description 5
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 5
- 239000005056 polyisocyanate Substances 0.000 claims description 5
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- 239000007795 chemical reaction product Substances 0.000 claims description 4
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- 229920000570 polyether Polymers 0.000 claims description 4
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- 238000010438 heat treatment Methods 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 abstract 4
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- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 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 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000010960 cold rolled steel Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QOOXGUCQYVVEFD-UHFFFAOYSA-N 2-butyl-2-methylpropane-1,3-diol Chemical compound CCCCC(C)(CO)CO QOOXGUCQYVVEFD-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- ODWASQWJJUOKNN-UHFFFAOYSA-N 2-phenoxyprop-2-enoic acid Chemical compound OC(=O)C(=C)OC1=CC=CC=C1 ODWASQWJJUOKNN-UHFFFAOYSA-N 0.000 description 2
- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical class CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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- 238000006068 polycondensation reaction Methods 0.000 description 1
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- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000009718 spray deposition Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012144 step-by-step procedure Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Description
1237052 五、發明說明(1 ) 本案關係一種可由輻射硬化而作爲油漆或淸漆之粉狀組 成物,由一種混合物構成,至少有一種含(甲基)丙烯醯基 之聚苯氧樹脂;和至少一種含(甲基)丙烯醯基而與聚苯氧 樹脂並與含(甲基)丙烯醯基非晶質聚酯不同之樹脂;和至 少一種依需要而加入之含(甲基)丙烯醯單體或寡聚物。 本發明粉狀組成物特別適合用於塗複金屬且有熱敏感性 之基質,結合在低的溫度熔融而於輻射中固化,有良好流 性而具出眾之耐溶劑性和撓性等一系列性質。 粉狀塗料爲乾而細分,自由流動,在室溫爲固體之材料 ,近年來已超越液狀塗料普受歡迎。雖然具有許多優點, 目前熱固性粉狀塗料通常至少在1 40°c之溫度固化。低於 此建議之溫度則塗層外觀不良、物理和化學性質欠佳。受 此限制之結果使粉狀塗料一般不適於塗複對溫度敏感之基 質,其如木材與塑膠,或含熱敏感性化合物之整合金屬件 。熱敏感性基質或化合物兩者要求低的固化溫度,較佳爲 低於14(TC,避免明顯之降解及/或變形。在低的溫度可以 輻射固化之粉料近來已有提出以解決此項問題。 使用不飽和樹脂以至於結合不飽和寡聚物而作爲用於可 輻射固化之粉狀塗料之膠合劑,已經成爲許多專利和專利 申請案之主題。 ‘ 衍生自含乙烯不飽和基之聚酯、丙烯酸共聚物或環氧樹 脂等之紫外光可固化之粉狀塗料組成物已經具有大量事例。 美國專利3,9 74,3 03 (Kansei油漆公司)說明各種不飽和 樹脂如含甲基丙烯醯基之聚酯或丙烯酸共聚物。 1237052 五、發明說明(2) 德國專利2 1 6 4 2 5 4 (B A S F)說明基於不飽和聚酯、丙烯酸 共聚物、環氧樹脂和其他含不飽和雙鍵之聚合物所成之粉 狀塗料。 美國專利4,1 29,488(SCM公司,N.Y.)揭示適用於紫外 光固化而含有乙烯不飽和聚合物之特定空間排列之粉狀油 漆塗料。(甲基)丙烯酸不飽和聚合物是一種空間排列之環 氧-聚酯聚合物,產自逐步之程序,具有在1〇〇〇與1〇,〇〇〇 間之數量平均分子量,具備適合之結晶性而爲自由流動粉 體,展現明銳之熔點,在80與200 °C之間,流性優異。 衍生自空間排列之環氧聚酯聚合物之粉狀油漆證明有優 異之硬度,合於所求之撓性和良好之MEK(甲基乙基酮)耐 性。 可輻射固化之粉狀塗料,尤其經發展而用於需要優異撓 性和耐化學性者,在涉及戶外耐久性之時全部未能如願。 現已令人驚訝而發現一種可輻射固化之粉狀塗料組成物 ,基於一種膠合劑,包含一種特別混合物,有至少一種含 (甲基)丙儲醯基之聚苯氧樹脂,至少一種含(甲基)丙烯醯 基而與聚苯氧樹脂並與含(甲基)丙烯醯基之非晶質聚酯不 同之樹脂,和依需要加入至少一種含(甲基)丙烯醯基單體 或寡聚物,在使用和固化時展現撓性和耐溶劑性之優異結 合。因此本發明之目的爲提供可輻射固化之粉狀塗料組成 物,含有: a) 10至90重量%至少一種含(甲基)丙烯醯基之聚苯氧樹脂; b) 10至90重量%至少一種與含(甲基)丙烯醯基之聚苯氧樹 -4- 1237052 五、發明說明(3) 脂a)並與含(甲基)丙烯醯基之非晶質聚酯不同之樹脂; c)〇至30重量%含(甲基)丙烯醯基之單體或寡聚物。 含(甲基)丙烯醯基之樹脂b)選自半結晶聚酯、聚酯醯胺 、聚氨基甲酸酯或聚丙嫌酸共聚物,單獨使用或混合使用。 含(甲基)丙烯醯基之聚苯氧樹脂是製自以聚苯氧樹脂之 縮水甘油基反應於: -(甲基)丙烯酸 -一種由(曱基)丙烯酸之羥基烷酯,其如(甲基)丙烯酸羥 乙酯,與酸酐如酞酸酐或琥珀酸酐者反應之生成物。 對於含(甲基)丙烯醯基之聚苯氧樹脂之製備,通常所用 者是構成於一習用反應器,裝有攪拌器,氧輸入管,含 (曱基)丙烯醯基之含羧酸基化合物之輸入管,和連接熱調 節器之溫度計。於保持在100與15(TC間溫度之環氧樹脂 ,加入自由基聚合抑制劑,其對環氧樹脂重量之比例例如 爲0.01至1%。然後緩慢加入貫質相當用量之含(甲基)丙 烯醯基之含羧酸基化合物至熔融之環氧樹脂。可依需要使 用催化劑以供酸/環氧基反應。此種催化劑例如胺類(例如 2-苯基咪唑啉),膦類(例如三甲基膦),銨鹽(例如是溴化 四丁基銨或氯化四丙基銨),錢鹽(例如溴化乙基三苯基鱗 或氯化四丙基鱗)。這些催化劑用於對環氧樹脂重量之 0.0 5至1 %之用量爲較佳。 反應進行程度是以所得含乙烯不飽和基之樹脂性質之測 定予以鑑測,其如利用酸數、羥數和不飽和度。 根據本發明配入於組成物內之含(甲基)丙烯醯基之聚苯 1237052 五、發明說明(4) 氧樹脂,較佳爲具〇 · 2至6 · 0之不飽和度,尤其是0.5至 4.5之每克樹脂雙鍵毫當量。且在一特佳具體例中另外具 有如下之特性:
-數量平均分子量(Μη)爲自450至5000,較佳在650與 3 500之間,依凝膠滲透色層分析法(GPC)所測 -玻璃轉移溫度(Tg)由微分掃描熱量計法(DSC)依ASTM D 3418測定,自30至80°C -在融態中之黏度,用錐/板黏度計(稱爲ICI黏度)於200 °c 依ASTM D 4287測定者,爲小於20000百萬巴斯葛•秒 (mPa· s) 〇 本發明含(甲基)丙烯醯基之聚酯是半結晶狀,製自以羥 基或羧酸官能性之半晶性聚酯與含(甲基)丙烯醯基且具可 與聚酯之官能基反應之官能基之單體之反應。 羥基或羧酸官能性半晶性聚酯之製備,習常上是製自一 或多種脂肪族、環脂性或芳香族多元酸與一或多種脂肪族 或環脂性多元醇。適合之脂肪族、環脂性或芳香族酸中之 例包括:酞酸、異酞酸、對酞酸、1,2-環己烷二羧酸、 1.3- 環己烷二羧酸、1,4-環己烷二羧酸、琥珀酸、戊二酸 、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、1,12_十 二烷二酸、苯偏三酸、苯均四酸及其中之酸酐,單獨或爲 混合物。 適合之脂肪族或環脂性多元醇之例中包括:乙二醇、 1.3- 丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,7_ 庚二醇、1,8·辛二醇、1,9-壬二醇、1,1〇_癸二醇、I,1卜十 1237052 五、發明說明(5) 一烷二醇' 1,12-十二烷二醇、2-甲基-1,3-丙二醇、新戊二 醇、2-丁基-2-甲基-1,3-丙二醇、新戊二醇之羥基特戊酸 酯、1,4-環己烷二醇、1,4-環己烷二甲醇、氫化雙酚A、 2,2,4,4-四甲基-1,3-環丁烷二醇、4,8-雙(羥甲基)三環-[5,2,1,02·6]癸烷。 本發明含羥或羧酸基之半晶性聚酯製自包含一或多個反 應步驟之程序。 在縮聚反應完成時,含羥或羧酸基之半晶性聚酯在反應 器內是熔融狀態,經冷卻至1⑽與160°C間之溫度,加入 相對於聚酯重量例如〇.〇1至1%之自由基聚合抑制劑,其 如酚噻嗪,或氫醌型之抑制劑,並以氧之輸入取代氮。 當從含羥基之半晶性聚酯開始時,實質上加入相當用量 之羥烷基(甲基)丙烯酸酯至其中。在所有的羥烷基(甲基) 丙烯酸酯被加入時,慢慢加入相當用量之二異氰酸酯至混 合物內。視需要而加入用於羥基/異氰酸酯反應之催化劑 。此種催化劑之例包含有機錫化合物(例如二丁基錫二月 桂酸酯、氧化二丁基錫、辛酸亞錫、1,3-二乙醯氧-1,1,3, 3-四丁基二錫氧烷)。這些催化劑之用量相對於聚酯重量 較佳爲〇至1 %。 另一方面,如由含羧酸基之半晶性聚酯開始,則實質加 入相當用量之縮水甘油基(甲基)丙烯酸酯至其中。可視需 要加入用於酸/環氧基反應之催化劑。此種催化劑包括例 如胺類(如2-苯基咪唑啉),膦類(如三苯基膦),銨鹽(例如 溴化四丁基銨或氯化四丙基銨)。此等催化劑之較佳用量 1237052 五、發明說明(6) 相對於聚酯重量爲0.05至1%。 反應進行程度是由所得半晶性聚酯性質,例如羥數 '酸 數、不飽和度及/或縮水甘油基(甲基)丙烯酸酯或羥烷基 (甲基)丙烯酸酯之含量等之測定予以鑑別。 本發明含(甲基)丙烯醯基之半晶性聚酯是以800至 16000之數量平均分子量(Μη),較佳爲自1300至8500 ; 熔融溫度自60至150t ;玻璃轉移溫度低於50°C ;不飽 和度範圍自0.15至2.00且較佳自0.35至1.50毫當量雙 鍵/克聚酯;ICI錐/板黏度在200°C測得者小於 50,000mPa*s等爲特徵。 本發明含(甲基)丙烯醯基之聚酯醯胺是製自以縮水甘油 基(甲基)丙烯酸酯與有羧基爲終端之聚酯醯胺之反應。該 聚酯醯胺則製自以羧基爲終端之聚酯與二胺之反應。 用於聚酯醯胺合成之羧基終端聚酯是製自以脂肪族、環 脂類或芳香族多元酸於其混合物或單獨使用’使其與脂肪 族或環脂類多元醇於其混合物或單獨使用而反應。多元酸 和多元醇兩者是選自稍早提示用於製備含(甲基)丙嫌醯基 之半晶性聚酯之事例者。 製備聚酯醯胺可用之二胺類,不論單獨或合倂,例如選 自乙烯二胺、丙烷二胺、1,5_戊烷二胺、1,6-己烷二胺 、1,2-環己烷二胺、1,3-環己烷二胺、1,4-環己烷二胺、 2,2-二甲基-1,3·丙烷二胺、N_(2·胺基乙基卜1,2·己烷二胺 、3,3,-二甲基_4,4’-二胺基二環己基甲烷、4,4’_二胺基二 環己基甲院、3,3’-二甲基-4,4’-二胺基二苯基甲院、4,4’- 1237052 五、發明說明(7) 二胺基二苯基甲烷和類似之化合物。 製備含(甲基)丙烯醯基之聚酯醯胺所用聚酯醯胺因而製 自如美國專利5,3 06,7 86所揭示之一種或多步驟程序之方 法。 在含羧基之聚酯醯胺之合成完成時,加入實質上對應用 量之縮水甘油基(甲基)丙烯酸酯至其中,因而開啓上述製 備含(甲基)丙烯醯基半晶性聚酯之程序,從有羧酸基官能 之聚酯始以至於以含(甲基)丙烯醯基之聚酯醯胺止,其特 徵爲數量平均分子量(Μη)爲自800至1 6000而較佳自 1 3 00至8 500 ;玻璃轉移溫度(Tg)自40至70 °C ;不飽和度 範圍自0.15至2.00而較佳自0.3 5至1.50毫當量雙鍵於 每克聚酯醯胺;且ICI錐/板黏度量測於200°C者小於 50000mPa*s 〇 本發明含(甲基)丙烯醯基聚氨基甲酸酯是製自以羥烷基 (甲基)丙烯酸酯和多元醇與聚異氰酸酯之反應。 製備含(甲基)丙烯醯基之聚氨基甲酸酯所用多元醇是選 自C2-C15之脂肪族或環脂類二醇、聚酯多元醇或聚醚多 元醇。 C2-C15脂肪族或環脂類二醇之例,爲乙二醇、1,3-丙二 醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,7-庚二醇、 1,8-辛二醇、1,9-壬二醇、1,1〇-癸二醇、1,11-十一烷二醇 、1,12-十二烷二醇、2-甲基-1,3-丙二醇、新戊二醇、2-丁 基-2-甲基-1,3-丙二醇、新戊二醇之羥基特戊酸酯、1,4-環 己烷二醇、1,4-環己烷二甲醇、氫化雙酚A、2,2,4,4-四甲基 1237052 五、發明說明(8) -1,3-環丁烷二醇、4,8-雙(羥甲基)三環-[5,2,1,0 2 6]癸烷。 聚酯多元醇,其以數量平均分子量(Μη)自8200至4000 爲特徵者,製自以化學計算起量之脂肪族或環脂類多元醇 ,與一種芳香族、脂肪族或環脂類多元酸。各多元酸或多 元醇是選自稍先所述用於製備含(甲基)丙烯醯基之半晶性 聚酯或聚酯醯胺者。 聚醚多元醇之例,如聚氧化乙二醇、聚氧化丙二醇、聚 氧化丁二醇、聚四伸甲基二醇、嵌塊共聚物如聚氧化丙二 醇與聚氧化乙二醇,聚1,2-聚氧化丁二醇與聚氧化乙二醇 ,聚1,4-四伸甲基二醇與聚氧化乙二醇等之結合,且各共 聚物二醇是製自以二或多種烯之氧化物之摻合物或次第加 合物。聚烯聚醚多元醇可以製自任何已知方法,如在 Interscience 出版社(1951)印行之 Encyclopedia Technology 第7冊,第25 7-2 62頁所揭示之方法。 在製備本發明含(甲基)丙烯醯基之聚氨基甲酸酯中可用 之聚異氰酸酯之例,爲1-異氰酸根絡合3,3,5-三甲基-5-異 氰酸根絡合甲基環己烷(異佛爾酮二異氰酸酯,IPDI),四 甲基二甲苯二異氰酸酯(TMXDI),六伸甲基二異氰酸酯 (HDI),三甲基六伸甲基二異氰酸酯,4,4’-二異氰酸根絡 合二環己基甲烷,4,4’-二異氰酸根絡合二苯基甲烷,其間 與2,4-二-異氰酸根絡二苯基曱烷之技術性混合物,以及 上述各二異氰酸酯之較高類似物,2,4 -二異氰酸根絡甲苯 與其和2,6-二異氰酸根絡甲苯之技術混合物,以及α,α 二甲基-間-異丙烯基苯甲基異氰酸酯之共聚合生成物(ΤΜΙ)。 -10- 1237052 五、發明說明(9) 供製含(甲基)丙烯醯基之聚氨基甲酸酯所用之羥烷基(甲 基)丙烯酸酯爲丙烯酸或甲基丙烯酸之羥烷基酯,較佳具 有2至4個碳原子於羥烷基內,其如羥乙基(甲基)丙烯酸 酯、2-和3 _羥丙基(甲基)丙烯酸酯、和2-、3-與4-羥丁基 (甲基)丙烯酸酯。 使上述起始成分反應製備聚氨基甲酸酯,是進行於惰性 溶劑如丙酮、乙酸乙酯、乙酸丁酯或甲苯之中’較佳之反 應溫度爲20至。反應最好進行於使聚異氰酸酯與 羥烷基(甲基)丙烯酸酯反應於第一步驟中,然後使所得生 成物與多元醇反應。 反應可以用適當催化劑加速,其如用辛酸酯、二丁基錫 二月桂酸酯或三級胺類如二甲基苯甲基胺。成爲反應生成 物所得之聚氨基甲酸酯或氨基甲酸酯丙烯酸酯可以加入合 適之抑制劑和抗氧化劑如酚類及/或氫醌類以防早變和不 宜之聚合作用,其用量基於聚氨基甲酸酯重量爲0·001至 0.30 0%。在製成聚氨基甲酸酯之前、之中及/或之後’可 以加入此等助劑。 本發明含(甲基)丙烯醯基之聚氨基曱酸酯之特性’如數 量平均分子量(Μη)爲自800至15000,較佳自1300至 8 5 00 ;玻璃轉移溫度(Tg)爲自40至100°C ;不飽和度範圍 自0.15至0.20而較佳爲0.35至1.50毫當量雙鍵每克聚 氨基甲酸酯;且ICI錐/板黏度在200°C測定者小於1 00000 mPa· s 〇 本發明粉狀組成物之含(甲基)丙烯醯基之丙_酸共聚物 -11- 1237052 五、發明說明(1 0 ) ,是製自於以具有官能基之含(甲基)丙烯醯基之單體,與 具有能夠與含(甲基)丙烯醯基之單體官能基反應之官能基 之丙烯酸共聚物之反應。 具有能夠反應之官能基之丙烯酸共聚物是由40至95莫 耳%之至少一種丙烯酸或甲基丙烯酸單體,0至60莫耳% 至少一種其他乙烯基不飽和單體,和自5至60莫耳%具 有選自環氧基、羧基、羥基或異氰酸基等之官能基而含 (甲基)丙烯醯基之單體等等所構成。 本發明粉狀組成物之含(甲基)丙烯醯基之丙烯酸共聚物 因而於一種兩步驟方法製成。 在第一步驟中以習知聚合方法製成丙烯酸酯共聚物,其 如聚合於本體中、在乳質中、或在有機溶劑之溶液中,在 其中某些部份之有官能基單體經共聚合而獲得官能基化之 丙烯酸酯共聚物。此種官能基單體,通常用5與60莫耳 %間之量,較佳爲環氧官能基單體,例如以縮水甘油基(甲 基)丙烯酸酯爲基礎。然而,酸官能性之單體,例如也可 以以(甲基)丙烯酸爲基礎;羥官能基單體例如以羥乙基 (甲基)丙烯酸酯爲基礎;或異氰酸官能基,例如以TMI(苯 ,1-(1-異氰酸根絡_1_甲基乙基)-4-(1-甲基乙烯基))或MOI (2-異氰酸根絡(甲基)丙烯酸酯)爲基礎。 各單體聚合於用自由基起始劑,其如過氧化苯醯、過氧 化三級丁基、過氧化十二烷醯、偶氮-雙-異丁醯腈等,其 用量爲單體重量之0.1至5%。製備丙烯酸共聚物所用之 適合單體爲(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基) -12- 1237052 五、發明說明(11) 丙烯酸丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯 、(甲基)丙烯酸三級丁酯、(甲基)丙烯酸2 -乙基己酯、(甲 基)丙烯酸硬脂酯、(甲基)丙烯酸三癸酯、(甲基)丙烯酸環 己酯、(甲基)丙烯酸苯甲酯、(甲基)丙烯酸苯酯、二甲基 胺基乙基(甲基)丙烯酸酯、二乙基胺基乙基(甲基)丙烯酸 酯、聚矽氧烷(甲基)丙烯酸酯和己內酯(甲基)丙烯酸酯。 通常此等單體是以在40與95莫耳%間之量存在。 可以在〇與60莫耳%之用量存在之其他可共聚合之單 體’例如爲苯乙嫌、α -甲基苯乙儲、乙嫌基甲苯、丙儲 腈、甲基丙烯腈、乙酸乙烯酯、丙酸乙烯酯、丙烯醯胺、 甲基丙烯醯胺、羥甲基甲基丙烯醯胺、氯乙烯、乙烯、丙 烯和C4_2〇之α烯烴。 在第二步驟中加成反應進行於獲自第一步驟之丙烯酸酯 共聚物之官能基化單體與能夠與該官能性單體反應之含 (甲基)丙烯醯基化合物之間。能夠反應之化合物例如特別 爲(甲基)丙烯酸、馬來酸酐、(Θ -甲基)縮水甘油基(甲基) 丙烯酸酯、烯丙基縮水甘油基醚、ΜΟΙ、羥乙基(甲基)丙 烯酸酯、羥丁基乙烯基醚、烯丙醇。 第二步驟之加戊反應可以完成於本質中或在溶劑內。常 用之溶劑爲甲苯、二甲苯、乙酸正丁酯等。可與官能基化 丙烯酸酯聚合物反應之含(甲基)丙烯醯基化合物是在50 與1 50°C間之溫度加入。混合物被攪拌歷數小時。反應之 進程以滴定跟監。 本發明粉狀組成物之含(甲基)丙烯醯基之丙烯酸共聚物 -13 - 1237052 五、發明說明(12) 有如下之特性: -數量平均分子量(Μη)爲自1〇〇〇至8000,較佳自2000 至6000之間,以GPC測定 -不飽和度爲自0.35至3.50,較佳自〇.5至2.5毫當量雙 鍵每克丙烯酸共聚物 -ICI錐/板丨谷融黏度’在2 0 0 °C依A S T M D 4 2 8 7所測定爲 小於 5 0,000mPa*s -玻璃轉移溫度(Tg)爲自45至l〇〇°C,由DSC依ASTM D 3 4 1 8測定 除此之外,本發明組成物有高達30重量%可以構成自 含(甲基)丙嫌酿基之卓體或募聚物,選自於参(2_經乙基) 異氰尿酸酯之三丙烯酸酯和三(甲基)丙烯酸酯;環氧基丙 烯酸酯和甲基丙烯酸酯,其係形成於由環氧化合物(例如 ,雙酚A之二縮水甘油醚)與丙烯酸或甲基丙烯酸之反應 。氨基甲酸酯之丙烯酸酯和甲基丙烯酸酯,其爲形成於由 一種有機之二-或聚異氰酸酯與一種羥烷基丙烯酸酯或羥 烷基甲基丙烯酸酯之反應,其中視需要而定並有單一及/ 或多羥基化醇(例如,羥乙基(甲基)丙烯酸酯與甲苯二異氰 酸酯或異佛爾酮二異氰酸酯之反應生成物),丙烯基丙烯 酸或甲基丙烯酸酯酯,其爲例如由(甲基)丙烯酸與含縮水 甘油基和甲基丙烯酸甲酯之共聚物之反應生成物,等等。 聚苯氧樹脂、半晶性聚酯及/或聚酯醯胺及/或聚氨基甲 酸酯及/或丙烯酸共聚物,適當倂同一或多種皆含(甲基)丙 烯醯基且全如上述之單體或寡聚物,於以紫外光或加速之 -14- 1237052 五、發明說明(1 3 ) 電子束可固化之粉狀組成物之製備中用作爲膠合劑,使該 組成物特別可以用作淸漆和油漆,其爲例如應用於根據擦 電或靜電噴槍方法之沉積技術;或根據在流化床中之沉積 技術。可輻射固化之粉狀組成物可以依所期望,加入其他 用於粉狀淸漆和油漆的製備中之習知成分而用作淸漆或油 漆。 因此’本發明也關係利用此等組成物所得之粉狀淸漆或 油漆。 最後,本發明也關係一種用於塗複物件之方法,特別是 對金屬物件,包括諸如以擦電或靜電噴槍噴灑沉積,或於 流化床中沉積,而將本發明之可輻射固化之粉狀組成物施 加於該物件上。繼而諸如以加熱於80至1 50°C之溫度經 過例如大約〇. 5至1 0分鐘之時間,使所得塗層熔融,並 用紫外光或加速之電子束照射在融態中之塗層固化。 對於用加速電子束使本發明粉狀組成物作輻射固化,其 爲不必使用光起始劑,可見此種輻射本身單獨提供自由基 之產生,足以快速充份高度固化。反之,若用波長在200 與600奈米之間的輻射(紫外光輻射),則本發明粉狀組成 物之固化必須至少有一種光起始劑存在。 可以用於本發明之光起始劑是選自於一般用於此目的者。 可用之適當光起始劑爲芳香族羰基化合物,其如二苯甲 酮及其烷基化或鹵化之衍生物,蒽醒及其衍生物,噻噸酮 及其衍生物,苯偶姻醚,芳香族或非芳香族^ -二酮類, 苯偶醯二烷基縮醛類,乙醯苯衍生物’和膦之氧化物。 -15- 1237052 五、發明說明(14) 可以適用之光起始劑例如爲2,2,-二乙氧基乙醯苯,2-,3-或4-溴乙醯苯’ 2,3-戊烷二酮,羥環己基苯基酮,苯甲 醛,苯偶姻’二苯甲酮,9,10-二溴蒽,2 -羥-2-甲基-1-苯 基丙烷-1 -酮,4,4 ’ -二氯二苯甲酮,咕噸酮,噻噸酮,苯 偶醯二甲基縮醛,二苯基(2,4,6-三甲基苯甲基)膦化氧, 等等。其中可以依有利情形使用光活化劑,其如三丁基胺 ,2-(2-胺基乙基胺基)乙醇,環己基胺,二苯基胺,三苯 甲基胺或胺基丙烯酸酯,其如例如由二甲基胺、二乙基胺 、二乙醇胺等二級胺,與多元醇聚丙烯酸酯如三羥甲基丙 烷、1,6-己二醇等之二丙烯酸酯等所成之加成生成物。在 本發明中之粉狀組成物可以含有0至15而較佳0.5至8.0 份光起始劑於1 〇〇重量份本發明組成物之膠合劑內。 根據本發明之可輻射固化之粉狀組成物和粉狀油漆與淸 漆,分別可以含有各種習用於粉狀油漆和淸漆製造中之添 加物。視需要而加至本發明可輻射固化之粉狀組成物內之 添加物,例如製成粉狀淸漆或油漆,尤其是吸收紫外光輻 射之化合物,其如TinUVin900(Ciba),基於位阻胺之光安 定劑(例如Ciba之Tinuvin 144),流性調節劑如Resiflow PV5(Worlee)、Modaflow(Monsanto)、Acrorial 4F(BASF) 或Crylcoat 1 09(UCB),除氣劑如苯偶姻等。 本發明可輻射固化之粉狀組成物另可加入各種改善塗複 性質之物質,其如以聚四氟乙烯改質之聚乙烯躐(例如 Lubrizol 之 Lanco Wax TF 1 83 0),聚乙烯蠟(例如 ΒΎΚ Chemie 之 Cera flour 961),聚丙烯鱲(例如 Lubrizol 之 Lanco Wax PP 1 362),聚醯胺蠟(例如 ELF Ato Chem 之 -16- 1237052 五、發明說明(15) Orgasol 3202D NAT),有機矽樹脂(例如 Protex 之 Modarez S 3 04P)等,或其摻合物。此等改質物是依需要就本發明組 成物內膠合劑爲1 00重量份而加入0至1 0份。各種顏料 和無機塡料也可以加至本發明可輻射固化之粉狀組成物。 須提示者,作爲顏料和塡料之事例,爲金屬氧化物者,如 氧化鈦、氧化鐵、氧化鋅等;金屬氧化物;金屬粉、硫化 物、硫酸鹽、碳酸鹽;矽酸鹽,其例如矽酸鋁;炭黑、滑 石、高嶺土、重晶石、鐵藍、鉛藍、有機紅、有機栗等。 此等添加物依習常用量使用,須知如果本發明可輻射固 化之粉狀組成物爲用作淸漆者,添加物之加入,其所具有 之不透明性質須予忽略。 用於本發明可輻射固化之粉狀組成物之製備,聚苯氧樹 月旨、半晶性聚酯及/或聚酯醯胺及/或聚氨基甲酸酯及/或丙 烯酸共聚物,依需要倂同一或多種單體或寡聚物,其全爲 含有(甲基)丙烯醯基’依需要而有光起始劑,依需要使用 習知用於粉狀油漆和淸漆製造之各種添加物,並依需要將 各種塗複性質改質物乾混合例如轉筒混合機內。然後將混 合物在自60至150°C之溫度範圍內勻化於擠押機內,例 如在 Buss Ko-Kneter 單螺桿擒押機或 Werner Pfeiderer, APV-Baker或Prism型之雙螺桿擠押機內。然後冷卻擠押 物’並硏磨過篩使獲得粒度較佳在1 〇與1 5 0微米間之粉 末。 代替以上各方法,也可以溶解/懸浮本發明膠合劑系統 之各種不飽和成分,視需要使用之光起始劑,和各種添加 -17- 1237052 五、發明說明(16) 物等於如二氯甲烷之溶劑內,硏磨以使獲得均勻懸浮液, 含有大約3 0重量%之固體物質,隨後蒸除溶劑,例如噴 灑乾燥於大約5(TC之溫度,根據已知之各種方法。 如此所得之粉狀油漆和淸漆,完全適合用於以習知技術 塗複物件,可謂以熟知之技術,例如在流化床中,或利用 擦電或靜電噴槍,予以沉積。 在已施用於相關物件之後,已沉積之塗料被加熱於例如 強迫循環烘箱內,或用紅外光燈,在8 0至1 5 0 °C之溫度 ,歷經大約0.5至1 0分鐘之時間,使獲得粉粒之熔融和 分散而成爲平滑、一致而連續之塗層於該物件之表面上。 然後以輻射固化,其如例如用中壓汞蒸汽紫外光輻射器發 射紫外光,較佳至少爲80至250瓦/直線厘米,或業者熟 知之任何其他光源,在例如大約5至20厘米之距離,經 充份時間固化塗料,其如1至60秒。 熔融之塗料也可被固化於加速之電子束,較佳至少爲 150仟電子伏特(keV),所用裝置之功率爲聚合固化組成物 層厚度之直接函數。 本發明也關係以塗覆方法塗覆物件之一部或全部。 本發明可輻射固化之粉狀組成物可以施加於大多數不同 基質,其如金屬、紙張、紙板、木材、纖維板、紡織物、 塑膠如聚碳酸酯、聚(甲基)丙烯酸酯、聚烯烴、聚苯乙烯 、聚氯乙烯、聚酯、聚氨基甲酸酯、聚醯胺,共聚物如丙 烯腈-丁二烯-苯乙烯(ABS),或乙酸丁酸纖維素等。 本發明可輻射固化之粉狀組成物也可被調製爲色調組成 -18- 1237052
五、發明說明(17) 物。 如下各實施例說明本發明而非予限制。除另有指明者, 全文及各實施例所指之份爲重量份。 竇施例1 含終端甲基丙烯醯基之半晶性聚酯三步驟之合成 第一步驟 將25 8.4份1,6·己二醇,10.4份三羥甲基丙烷和1.9份 作爲催化劑之三辛酸正丁基錫加入至四口圓底燒瓶內,裝 有攪拌器、連接至水冷冷凝器之蒸餾柱、氮氣輸入管和連 接熱調節器之溫度計。於氮氣氛下加熱於混合物,攪拌於 大約140°C之溫度,然後加入484.4份對酞酸,繼續攪拌 ,並加熱於混合物至1 90°C之溫度,於其時開始蒸餾所形 成之水。然後繼續逐漸加熱以至物體達到2 3 0 °C之溫度。 在大約已收集所形成之水量達95%理論量時,獲得透明之 聚酯。 如是獲得之含終端羥基之半晶性聚酯有如下之特性: AN(酸數)=9.5毫克KOH/克 OHN(羥數)=42毫克KOH/克 ICI 175°c =700mPa*s 第二步驟 使在第一步驟所得含羥基聚酯冷卻至200°C,加入75 份異酞酸至其中。然後逐漸加熱反應混合物至23 (TC之溫 度。保持此反應混合物於此溫度大約二小時,直至混合物 變爲透明,然後在23 〇°C逐漸減壓三小時。 -19- 1237052 五、發明說明(18) 如是所得含終端羧酸基之半晶性聚酯有如下之特性: AN =3 1毫克KOH/克 OHN 二1毫克KOH/克 ICI 1 75〇C -7450mPa*s Mn(GPC) -45 5 0 第三步驟
使在第二步驟所得含終端羧酸基之聚酯冷卻至1 5 0 °C, 加入〇.4份二-三級丁基氫醌,作爲聚合抑制劑;和4.1份 乙基三苯基錢,作爲催化劑,至於其中;在氧氣氛下攪拌 中緩慢加入62.2份縮水甘油基(甲基)丙烯酸酯。一小時後 加入完成,所得含終端甲基丙烯醯基之半晶性聚酯有如下 之特性: AN =1.5 毫克 KOH/克 OHN =32 毫克 KOH/克 不飽和度 =0.5毫當量/克 ICI 1 7 5 °C =5300mPa*s
Tm(淬冷-DSC 20°C /分)=1 0 1°C Mn(GPC) -4890 實施例2 以22 1 · 3份乙酸正丁酯加至雙壁5公升圓底燒瓶內,裝 有攪拌器、水冷冷凝器、氮氣輸入管和附於熱調節器之探 溫頭。 在氮氣通過溶劑衝冒之際,連續加熱至攪拌燒瓶內容物 。在ll〇°C之溫度,加入由234.7份乙酸正丁酯和13.4份 -20- 1237052 五、發明說明(19) 2,2’-偶氮雙(2-甲基丁腈)之混合物至燒瓶內,用蠕動泵於 2 1 5份鐘內加入。在開始此項進料五分鐘後,用另一泵開 始加入如下之混合物: -102.7份甲基丙烯酸羥乙酯 -88.5 份丙烯酸異冰片酯 -162.9份甲基丙烯酸甲酯 -88.5 份甲基丙烯酸正丁酯 此項進料費時180分鐘。 具有羥官能基之丙烯酸共聚物特性如下: OHN =96 毫克 KOH/克 ICI 125〇C =22500mPa*s Tg(淬冷-DSC,20°C/分)=53°C 然後成爲溶液被轉入至一圓底單壁燒瓶內。 加熱於溶液至40°C並以空氣連續衝冒。30分鐘後在 180分鐘內加入0.09份Norsocryl 200(EH Achem所售抑 制劑)和87.6份2-異氰酸根絡乙基甲基丙烯酸酯。經由二 丁基胺與鹽酸反滴定,規則核看異氰酸根數。若異氰酸根 含量少於原始値之0.3%,則冷卻燒瓶內容物,並於30°C 乾燥於旋轉蒸發器內。 如是所製乙烯不飽和之丙烯酸共聚物有如下之特性: 不飽和性 =1.45毫當量/克 ICI 100°c -50000mPa*s Tg(淬冷-DSC,20°C/分) Mn(GPC) =3 125 -21 - 1237052 五、發明說明(2〇 ) 實施例3 在一裝有攪拌器,氧氣輸入管、(甲基)丙烯酸輸入管和 連接熱調節器之熱電偶等之四口圓底燒瓶中,9 1 0份 Araldite GT7 0 04,一種雙酚A型環氧樹脂,在氧氣中加 加熱14CTC之溫度。隨後加入0.8份之乙基三苯基鳞化溴 ,並開始加入9 0份含0.2份二-三級-丁基氫醌之丙烯酸。 丙烯酸之加入完成於3小時之內。丙烯酸之加入完成後一 個半小時,獲得具有如下特性之樹脂: AN =7毫克KOH/克 不飽和性 =1.24毫當量/克 ICI 200°C =700mPa*s Tg(淬冷-DSC,20°C/分)=49°C Mn(GPC) =1650 實施例4與5 兩種白色粉末,可以用靜電噴槍噴灑而製造塗層,其爲 製自分別以實施例1和2之含甲基丙烯醯基之樹脂,與實 施例3含甲基丙烯醯基之聚苯氧樹脂所成之摻合物,此等 粉末之配方如下: 膠合劑 750.0份 二氧化鈦(Kronos 2310(Kronos)) 250.0 份 α_ 經基酮(Irgacure2959(Ciba)) 12.5 份 雙醯基膦化氧(Irgacure 819(Ciba)) 12.5 份 流性調節齊!J (R e s i f 1 〇 w P V 5 (W 〇 r 1 e e C h e m i e)) 1 0 · 0 份 此等粉狀組成物製自於乾混合成分。所得混合物在 -22- 1237052 五、發明說明(21) Prism之16毫米(L/D= 15/1)之雙螺桿擠押機(Prism公司所 製)內於大約70至140 °C之溫度勻化,並硏磨擠押物於 Alpine 100 UPZ磨機內(Alpine公司所供)。完成後,將粉 末過篩以獲得粒度在1 0與1 1 〇微米之間。 如是所得粉末分別含有一種膠合系統,組自: 實施例4 實施例5 實施例1 : 563份 實施例2 : 3 75份 實施例3 : 187份 實施例3 : 3 75份 實施例6 以實施例4和5所述配製之粉末,用靜電噴槍於60仟 伏之電壓施加於未處理之冷軋鋼上,成爲40至100微米 厚度之薄膜。 然後使所沉積之塗層在中度紅外線/對流爐(Triab)內接 受14(TC溫度於大約3分鐘時間之內。然後接受由160瓦/ 厘米鎵所摻雜而發射之紫外光照射,繼用160瓦/厘米中 壓汞蒸汽紫外光燈泡(Fusion UV System Ltd.),紫外光總 劑量爲4000毫焦耳/厘米2。 試驗所得粉末塗層,得有如下之結果: -外觀評價:實施例4 =良;實施例5 =良。兩種粉末均有 平滑而有光澤之外觀,無任何疵病。 -MEK耐性:實施例4>200次雙抹拭,實施例5>200次 雙抹拭,其爲相當於用浸漬MEK(甲基乙基酮)之棉拭墊 抹拭運動二倍(往與回復)之數,MEK對固化膜表面之外 觀無不良影響。 -23- 1237052 五、發明說明(22) -反向衝擊:實施例4=160公斤•厘米,實施例5 = 60公斤 •厘米,耐反向衝擊(RI)之値以公斤·厘米計,依據 ASTM D 2795,於冷軋鋼上。 -直接衝擊:實施例4=160公斤•厘米,實施例5 = 80公斤 •厘米,耐直接衝擊(DI)之値以公斤·厘米計,依據 AS TM D 2 795,於冷軋鋼上。 雖然本發明已詳細說明,並參考其特別之具體例,顯然 熟悉此技術者將能夠在不離其精神與範圍從中作成各種變 更和修改。 -24-
Claims (1)
- ^ FI__ 六、申請專利範圍 第9 1 1 1 5426號「可由輻射固化之粉狀被覆組成物」專利案 (94年3月修正) 六申請專利範圍: 1 . 一種可輻射固化之粉狀被覆組成物,其係包含: a) 10至90重量%含(甲基)丙烯醯基之聚苯氧樹脂; b) l〇至90重量%含(甲基)丙烯醯基之樹脂,其係選 自含(甲基)丙烯醯基之聚酯醯胺及/或聚氨基甲酸 酯及/或丙烯酸共聚物。 2 ·如申請專利範圍第1項之可輻射固化之粉狀被覆組 成物,其中含(甲基)丙烯醯基之聚苯氧樹脂a)是由 (甲基)丙烯酸與含縮水甘油基之聚苯氧樹脂之反應 生成物。 3 .如申請專利範圍第1或2項之可輻射固化之粉狀被 覆組成物,其中含(甲基)丙烯醯基之聚苯氧樹脂a) 至少以如下性質之一爲特徵: -數量平均分子量範圍自450至5000 ; -玻璃轉移溫度範圍自30至80°C ; -不飽和度範圍自0.2至6.0毫當量之雙鍵於每克 含(甲基)丙烯醯基之聚苯氧樹脂; -熔融黏度(錐/板,於200°C )小於20000mPa· s。 4 ·如申請專利範圍第丨或2項之可輻射固化之粉狀被 S組成物,其中含(甲基)丙烯醯基之聚苯氧樹脂a) 至少以如下性質之一爲特徵: 1237052 六、申請專利範圍 -數量平均分子量範圍自650至3500; -玻璃轉移溫度範圍自30至80°C ; -不飽和度範圍自0.5至4.5毫當量之雙鍵於每克 含(甲基)丙烯醯基之聚苯氧樹脂; -熔融黏度(錐/板,於200°C )小於20000mPa· s。 5 .如申請專利範圍第1或2項之可輻射固化之粉狀被 覆組成物,其中含(甲基)丙烯醯基之聚酯醯胺是獲 自以縮水甘油基(甲基)丙烯酸酯與以羧基爲終端之 聚酯醯胺之反應。 6 .如申請專利範圍第5項之可輻射固化之粉狀被覆組 成物,其中用以製備以(甲基)丙烯醯基爲終端之聚 酯醯胺之以羧基爲終端之聚酯醯胺,是獲自以二胺 與含羧基之聚酯反應,該聚酯則製自以一或多種脂 肪族、環脂類或芳香族多元酸與一或多種脂肪族或 環脂類多元醇之反應。 7 .如申請專利範圍第1或2項之可輻射固化之粉狀被 覆組成物,其中含(甲基)丙烯醯基之聚酯醯胺至少 以如下性質之一爲特徵: -數量平均分子量範圍自800至16000; -終端不飽和度爲0.15至2.00毫當量之雙鍵於每 克聚酯; -玻璃轉移溫度範圍自40至70°C ; -熔融黏度(錐/板,於200°C )小於50000mPa· s。 1237052 六、申請專利範圍 8·如 申請專利範圍第1或2項之可輻射固 化 之 粉 狀 被 覆 組成物,其中含(甲基)丙烯醯基之聚 酯 醯 胺 至 少 以 如下性質之一爲特徵: - 數量平均分子量範圍自1 300至8500; - 終端不飽和度爲0.35至1.50毫當量 之 雙 鍵 於 每 克聚酯; - 玻璃轉移溫度範圍自40至70°C ; - 熔融黏度(錐/板,於200°C)小於50000mPa· 丨S 0 9.如 申請專利範圍第1或2項之可輻射固 化 之 粉 狀 被 覆 組成物,其中含(甲基)丙烯醯基之聚 氨 基 甲 酸 酯 獲 自於以羥烷基(甲基)丙烯酸酯和多元 醇 與 一 聚 異 氰 酸酯之反應。 10.如 申請專利範圍第9項之可輻射固化之 粉 狀 被 覆 組 成 物,其中用以製備含(甲基)丙烯醯基 之 聚 氨 基 甲 酸 酯之多元醇是02-(:15脂肪族或環脂二 醇 聚 酯 多 元 醇或聚醚多元醇。 11 ·如 申請專利範圍第1或2項之可輻射固 化 之 粉 狀 被 覆 組成物,其中含(甲基)丙烯醯基之聚 氛 基 甲 酸 酯 是 以如下性質之至少一項爲特徵: - 數量平均分子量範圍自800至1 5000; - 終端不飽和度爲0.15至2.00毫當量 之 雙 鍵 於 每 克聚酯內; 玻璃轉移溫度範圍自40至10CTC ; -3-1237052 六、申請專利範圍 -熔融黏度(錐/板於200°C )小於l〇〇〇〇〇mPa*s。 1 2 .如申請專利範圍第1或2項之可輻射固化之粉狀被 覆組成物,其中含(甲基)丙烯醯基之聚氨基甲酸酯 是以如下性質之至少一項爲特徵: -數量平均分子量範圍自13 00至8500; -終端不飽和度爲0.35至1.50毫當量之雙鍵於每 克聚酯內; -玻璃轉移溫度範圍自40至100°C ; -熔融黏度(錐/板於200°C)小於1 0000 0mPa*s。 1 3 ·如申請專利範圍第1或2項之可輻射固化之粉狀被 覆組成物,其中含(甲基)丙烯醯基之丙烯酸共聚物 是獲自下列反應: --種具有官能基之丙烯酸共聚物,其獲自以40至 95莫耳%之至少一種具有丙烯酸或甲基丙烯酸基之 單體、和5至60莫耳%之具有能夠與環氧基、羧 基、羥基異氰酸酯基反應之官能基的乙烯不飽和 單體; -一種具有(甲基)丙烯醯基和能夠與羧基、環氧基、 異氰酸酯基或羥基反應之官能基的單體。 1 4 ·如申請專利範圍第丨或2項之可輻射固化之粉狀被 覆組成物,其中含(甲基)丙烯醯基之丙烯酸共聚物 是獲自下列反應: -一種具有官能基之丙烯酸共聚物,其獲自以至 -4- 1237052 $'申請專利範圍 95莫耳%之至少一種具有丙烯酸或甲基丙烯酸基之 單體、0.001至60莫耳%之另一種乙烯不飽和單體 、和5至60莫耳%之具有能夠與環氧基、羧基、 羥基異氰酸酯基反應之官能基的乙烯不飽和單體 -一種具有(甲基)丙烯醯基和能夠與羧基、環氧基 、異氰酸酯基或羥基反應之官能基的單體。 1 5 ·如申請專利範圍第1或2項之可輻射固化之粉狀被 覆組成物,其中含(甲基)丙烯醯基之丙烯酸共聚物 至少有如下性質之一項爲特徵: -數量平均分子量範圍自1〇〇〇至8000 ; -玻璃轉移溫度範圍自45至100°C ; -不飽和度範圍自0.35至3.50毫當量之雙鍵於每 克丙烯酸共聚物; -熔融黏度(錐/板,於200°C )小於50000mPa· s。 1 6 .如申請專利範圍第1或2項之可輻射固化之粉狀被 覆組成物,其中含(甲基)丙烯醯基之丙烯酸共聚物 至少有如下性質之一項爲特徵: —數量平均分子量範圍自2000至6000 ; -玻璃轉移溫度範圍自4 5至1 0 0 °c ; -不飽和度範圍自〇·5至2.5毫當量之雙鍵於每克 丙烯酸共聚物; -熔融黏度(錐/板,於200°c )小於50000mPa· s。 1237052 六、申請專利範圍 17 如 甲師 專 利 範 圍第1或2項之可輻射固化之粉 狀 被 覆 組成 物 其 中含有自0.001至30重量%之含(甲基) 丙 烯酸 基 之 單 體或寡聚物。 18 如 申請 專 利 範 圍第1或2項之可輻射固化之粉 狀 被 覆 組成 物 其 對於總計100重量份之含(甲基)丙 烯 醯 基 之聚 苯 氧 和 含(甲基)丙烯醯基之聚酯醯胺及/ 或 含 (甲基)丙 烯 醯 基之聚氨基甲酸酯及/或含(甲基)丙 Μ 醯 基之 丙 烯 酸 共聚物及/或含(甲基)丙烯醯基之 單 mm 體 或 寡聚 物 (如若存在),另含0.5至15重量份之 光起 始 劑, 並 選 擇 性含有一光活化劑。 19 . .如 申請 專 利 範 圍第1或2項之可輻射固化之粉 狀 被 覆 組成 物 > 其 對於總計100重量份之含(甲基)丙 烯 醯 基 之聚 苯 氧 和 含(甲基)丙烯醯基之聚酯醯胺及/ 或 含 (甲基)丙 醯 基之聚氨基甲酸酯及/或含(甲基)丙 嫌 醯 基之 丙 烯 酸 共聚物及/或含(甲基)丙烯醯基之 單 體 或 寡聚 物 (如若存在),另含0.5至8.0重量份 之光 起 始劑 , 並 選 擇性含有一光活化劑。 20 •如 申請 專 利 範 圍第1或2項之可輻射固化之粉 狀 被 覆 組成 物 其係用於粉狀淸漆或粉狀油漆。 21 # 一 種塗 覆 物 件 之方法,其中如申請專利範圍第 1 至 19 1項中任- -項之可輻射固化之粉狀被覆組成物 或 如 申請 專 利 範 圍第20項之粉狀淸漆或粉狀油漆 係 被 沉 積於物件 :上 .,繼而熔融如是所得之塗層,並 -6- 於 熔 1237052 六、申請專利範圍 融態中以輻射固化塗層。 22 ·如申請專利範圍第2 1項之方法,其中塗層之熔融是 以在80至150°C之溫度加熱塗層,經歷0.5至10.0 分鐘之時間而達成;及/或熔融狀態之塗層的硬化是 以曝露該塗層於紫外光輻射或於加速之電子束,經 歷足以形成固化塗層之時間而達成。 23 ·如申請專利範圍第21或22項之方法,其係用於塗 覆一具有局部或全部塗層之物件。
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US20150335568A1 (en) * | 2012-06-22 | 2015-11-26 | Mycone Dental Corporation | Radiation-curable, stable nail gel compositions and methods of preparation and use |
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US20170088665A1 (en) | 2015-09-25 | 2017-03-30 | Eastman Chemical Company | POLYMERS CONTAINING CYCLOBUTANEDIOL AND 2,2 BIS(HYDROXYMETHYL) AlKYLCARBOXYLIC ACID |
US9988553B2 (en) | 2016-02-22 | 2018-06-05 | Eastman Chemical Company | Thermosetting coating compositions |
US10011737B2 (en) | 2016-03-23 | 2018-07-03 | Eastman Chemical Company | Curable polyester polyols and their use in thermosetting soft feel coating formulations |
US10941302B2 (en) | 2018-03-07 | 2021-03-09 | Ppg Industries Ohio, Inc. | Powder coating composition |
CN111423809B (zh) * | 2020-04-13 | 2022-02-11 | 上海君子兰新材料股份有限公司 | 一种led-uv喷涂哑光面漆及其制备方法 |
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JPS565276B2 (zh) * | 1973-10-29 | 1981-02-04 | ||
US4129488A (en) * | 1976-11-08 | 1978-12-12 | Scm Corporation | Ultraviolet curable epoxy-polyester powder paints |
NL9200506A (nl) * | 1992-03-19 | 1993-10-18 | Dsm Nv | Bindmiddelsamenstelling voor poedercoatings. |
BE1010712A3 (fr) * | 1996-10-25 | 1998-12-01 | Ucb Sa | Compositions en poudre a base de polyesters semi-cristallins et de polyesters amorphes, contenant des groupes methacrylyle terminaux. |
BE1010713A3 (fr) * | 1996-10-25 | 1998-12-01 | Ucb Sa | Compositions en poudre a base de polyesters semi-cristallins et de copolymeres acryliques; contenant des groupes (meth)acrylyle. |
EP1125996A1 (en) * | 2000-02-09 | 2001-08-22 | Ucb, S.A. | Radiation curable powder compositions |
-
2002
- 2002-07-11 TW TW91115426A patent/TWI237052B/zh not_active IP Right Cessation
- 2002-07-23 WO PCT/EP2002/008190 patent/WO2003010248A1/en not_active Application Discontinuation
- 2002-07-23 CN CNB028146867A patent/CN1257237C/zh not_active Expired - Fee Related
- 2002-07-23 EP EP20020754930 patent/EP1427785A1/en not_active Withdrawn
- 2002-07-23 US US10/484,791 patent/US6995194B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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CN1257237C (zh) | 2006-05-24 |
US20040225027A1 (en) | 2004-11-11 |
EP1427785A1 (en) | 2004-06-16 |
CN1535302A (zh) | 2004-10-06 |
US6995194B2 (en) | 2006-02-07 |
WO2003010248A1 (en) | 2003-02-06 |
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