CN1535289A - 涂覆底材的方法 - Google Patents
涂覆底材的方法 Download PDFInfo
- Publication number
- CN1535289A CN1535289A CNA018183948A CN01818394A CN1535289A CN 1535289 A CN1535289 A CN 1535289A CN A018183948 A CNA018183948 A CN A018183948A CN 01818394 A CN01818394 A CN 01818394A CN 1535289 A CN1535289 A CN 1535289A
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- Prior art keywords
- acid
- coating
- group
- component
- sealing
- 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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- 238000000576 coating method Methods 0.000 title claims abstract description 27
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000007789 sealing Methods 0.000 claims description 19
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- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 7
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- 229910000831 Steel Inorganic materials 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
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- 125000005594 diketone group Chemical group 0.000 description 2
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Abstract
本发明涉及一种涂覆底材的方法，包括在将某些液态涂覆剂组合物涂布在物体(底材)上后，用紫外线(UV)照射并进行加热后反应固化。
Description
本发明涉及一种涂覆底材的方法，包括在将某些液态的涂覆剂组合物涂覆在物体(底材)上之后，用紫外线(UV)进行照射并进行加热后反应固化。
用紫外线进行的诸如漆类的涂层的固化由于其消耗较低的能量和溶剂并且高速，所以是十分有效的。但是缺点是在某些基底尤其是金属上该涂层常常附着的不充分。例如EP-A 0 928 800公开了一种具有由紫外线固化的异氰酸酯基团的尿烷(甲基)丙烯酸异氰酸酯组成的涂覆系统，该化合物具有游离的异氰酸酯(NCO)基团和与NCO基团反应的基团。因此，制备了两种组分的所述涂覆系统，就在涂覆涂层前将两种组分进行混合。混合后在几小时内使用。
US-A 4 961 960公开了一种从储存液态涂覆组合物(涂覆剂)角度考虑的一元系统。该系统主要由下列两种组分组成：a)具有多个烯属不饱和基团的可光硬化的单体或聚合物和b)由多异氰酸酯、用于多异氰酸酯的封闭剂和具有至少一个烯属不饱和基团的可光聚合的醇组成的加成物。另外，限制条件是组分a)不含NCO基团或封闭的NCO基团，并且a)和b)两者总的烯属不饱和基团数至少为4。该专利公开了使用不具有烯属不饱和基团的多异氰酸酯b)不进行加热后固化形成不稳定的膜并且经加热后固化形成光学性能不足的膜。
因为难以制备既含烯属不饱和基团又含封闭的NCO基团的多异氰酸酯产物，因此，本发明的目的是提供一种涂层方法，在同时采用封闭的多异氰酸酯与紫外线可固化的低聚物或聚合物时，在经紫外线固化后形成稳定的涂层并且在经进一步的热固化后形成外观无可挑剔的涂层。
因此，本发明提供一种涂覆底材的方法，该方法通过涂布由至少下列组分组成的涂覆剂：
A)至少一种含至少两个(甲基)丙烯酸酯基团的化合物，他们不含异氰酸酯基和封闭的异氰酸酯基，
B)至少一种封闭的多异氰酸酯和
C)至少一种光敏引发剂，
接着进行紫外线固化并通过提高涂层的温度进行后固化，其特征在于：组分A)含有至少一种与异氰酸酯基团反应的基团，组分B)不含烯属不饱和基团。
本发明中使用的术语“(甲基)丙烯酸酯”是指丙烯酸和/或甲基丙烯酸的酯及其它们的混合物。
本发明方法中使用的涂覆剂的成分(组分)A)选自本身已知的光照可固化的粘合剂，条件是该粘合剂含有至少一种与异氰酸酯反应的基团，优选至少含有羟基基团。这种粘合剂例如是环氧丙烯酸酯、聚酯丙烯酸酯、聚醚丙烯酸酯或部分(甲基)丙烯酸化的分子量低于600的三-或更高官能化醇。优选使用羟基基团的平均数为1.5-3的环氧丙烯酸酯。组分A)可任选含有至多4个烯属不饱和基团。
在制备环氧丙烯酸酯时，例如在P.K.T.Oldring(Ed.)，Chemistry & Technologyof UV & EB Formulations For Coatings，Inks & Paints，第2卷，1991，SITA Technology，伦敦，第37-68页和在EP-A 816 412中描述的，通常缩水甘油醚与羧酸反应，形成具有仲羟基的产物。这种产物特别适合于本发明的方法。
另外，可以使用含羟基的聚酯丙烯酸酯作为组分A)，其OH含量为60-300mgKOH/g。在制备羟基官能化聚酯丙烯酸酯时，总共可使用7组单体组分：
1、分子量为62-286的(环)链烷二醇(即具有(环)脂肪连接的羟基的二元醇)如乙二醇、1，2-和1，3-丙二醇、1，2-、1，3-和1，4-丁二醇、1，5-戊二醇、1，6-己二醇、新戊二醇、环己基-1，4-二甲醇、1，2-和1，4-环己烷二醇、2-乙基-2-丁基丙二醇，含醚氧的二醇如二乙二醇、三乙二醇、四乙二醇、二丙二醇、三丙二醇、聚乙二醇、聚丙二醇或聚丁二醇，其最大分子量约为2000，优选约1000，特别优选约500。前面提到的二醇与ε-己内酯或其他内酯的反应产物同样可作为二醇使用；
2、分子量为92-254的三元-和更多元醇如甘油、三羟甲基丙烷、季戊四醇、二季戊四醇和山梨醇或基于这些醇的聚醚如1摩尔三羟甲基丙烷与4摩尔环氧乙烷的反应产物；
3、一元醇如乙醇、1-和2-丙醇、1-和2-丁醇、1-己醇、2-乙基己醇、环己醇和苄醇等；
4、分子量为104-约600的二羧酸和/或其酸酐，例如邻苯二甲酸、邻苯二甲酸酐、间苯二甲酸、四氢邻苯二甲酸、四氢邻苯二甲酸酐、六氢邻苯二甲酸、六氢邻苯二甲酸酐、环己基二羧酸、马来酸酐、富马酸、丙二酸、琥珀酸、琥珀酸酐、戊二酸、己二酸、庚二酸、辛二酸、癸二酸、十二烷二酸、氢化的二聚脂肪酸；
5、多官能的羧酸或其酸酐如苯偏三酸和苯偏三酸酐；
6、一元羧酸，例如苯甲酸、环己基羧酸、2-乙基己酸、己酸、辛酸、癸酸、月桂酸、天然和合成的脂肪酸和
7、丙烯酸、甲基丙烯酸或二聚丙烯酸。
含羟基的聚酯丙烯酸酯包括至少一种1或2组的组分与至少一种4或5组的组分和至少一种7组的组分的反应产物。
另外，部分(过量的)羧基，尤其是(甲基)丙烯酸上的羧基可与单-、二-或多环氧化物反应。该反应可用以提高聚酯丙烯酸酯的OH-数，因为在环氧乙烷-酸发生反应时，总是形成OH-基团。形成产物的酸值在20mg KOH/g以下，优选在10mgKOH/g以下和更优选在5mg KOH/g以下。
例如在P.K.T.Oldring(Ed.)，Chemistry & Technology of UV & EB FormulationsFor Coatings，Inks & Paints，第2卷，1991，SITA Technology，伦敦，第123-135页中描述了聚酯丙烯酸酯的制备。
也可以使用分子量低于600的所述环氧基丙烯酸酯、聚酯丙烯酸酯、聚醚丙烯酸酯或部分(甲基)丙烯酸化的三-或多官能醇与二-或多异氰酸酯的反应产物，只要反应产物含有至少一个可与异氰酸酯反应的基团，优选至少一个羟基。合适的二-或多异氰酸酯主要是脂族、芳脂族和芳香族化合物，例如亚丁基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、异佛尔酮二异氰酸酯(IPDI)、三甲基六亚甲基二异氰酸酯(2，2，4-和/或2，4，4-三甲基六亚甲基二异氰酸酯)、二(异氰酸根合环己基)甲烷、甲苯二异氰酸酯、二苯基甲烷二异氰酸酯、异氰酸根合甲基-1，8-辛烷二异氰酸酯或其具有尿烷(Urethan)、异氰脲酸酯、脲基甲酸酯、缩二脲、Uretdion、亚氨基噁二嗪二酮结构的衍生物和它们的混合物。
不含烯属不饱和基团的组分B)的封闭的多异氰酸酯是人们熟悉的，例如描述于Progress in Organic Coatings，第36卷，3，1999，第148-172页。典型的是通过多异氰酸酯与封闭剂发生反应制备封闭的多异氰酸酯。
合适的多异氰酸酯主要是脂族、芳脂族和芳香化合物，其中优选脂族化合物，例如亚丁基二异氰酸酯、六亚甲基二异氰酸酯(HDI)、异佛尔酮二异氰酸酯(IPDI)、三甲基六亚甲基二异氰酸酯(＝2，2，4-和/或2，4，4-三甲基六亚甲基二异氰酸酯)、二(异氰酸根合环己基)甲烷、异氰酸根合甲基-1，8-辛烷二异氰酸酯或具有尿烷、异氰脲酸酯、脲基甲酸酯、缩二脲、Uretdion、亚氨基噁二嗪二酮结构的衍生物和它们的混合物。特别优选地是具有异氰脲酸酯结构单元的HDI和/或IPD的衍生物。
作为封闭剂使用的是已知的单官能封闭剂，例如丙二酸、乙酰乙酸乙酯、内酰胺、肟、吡唑、三唑、咪唑、胺或这些化合物的任意混合物。优选使用在至180℃，优选至160℃的温度下裂解的封闭剂。优选的是二异丙铵、丁酮肟、环己酮肟和/或3，5-二甲基-吡唑。特别优选的是二异丙胺。
B)中封闭的NCO基团与A)中与NCO基团反应的基团的比例为1∶0.2～1∶2，优选1∶0.5～1∶1.2，更优选1∶0.9～1∶1。
光敏引发剂C)是已知的引发剂，这种引发剂在用高能射线例如紫外线照射后可以引发游离基聚合反应。例如在P.K.T.Oldring(Ed.)，Chemistry & Technology ofUV & EB Formulations For Coatings，Inks & Paints，第3卷，1991，SITA Technology，伦敦，第61-325页中描述了这种光敏引发剂。实例是提到的2-羟基苯基酮如1-羟基环己基-苯基酮，苯偶酰酮缩醇如苯偶酰甲基酮缩醇，酰基膦氧化物如双-(2，4，6-三甲基苯甲酰基)-苯基膦氧化物，二酰基膦氧化物，二苯酮和其衍生物。光敏引发剂可以单独使用，也可与其他的加速剂或辅助引发剂混合使用，添加量按涂料体系的固体计为0.1-10重量份，优选2-7重量份，更优选3-4重量份。
按常规方法混合组分A)、B)和C)以制备涂覆剂。混合物的成分还可以有涂漆工艺，尤其是可辐射硬化漆工艺和聚氨酯化学中通常使用的助剂和添加剂。
为了增强硬化的漆层和任选底材的耐候性，可以添加紫外线吸收剂，优选具有吸收范围至max.390纳米的吸收剂和稳定剂，已知这些试剂用作HALS(HALS＝“受阻胺光稳定剂”)。合适的紫外线吸收剂是三苯基三嗪型，例如Tinuvin400(Ciba)或草酸二(N-酰苯胺)型，例如Sanduvor3206(Clariant)。紫外线吸收剂的添加量按固态粘合剂计优选为0.5～3.5％。合适的HALS是市场销售的类型，例如Tinuvin292或Tinuvin123(Ciba)或Sanduvor3058(Clariant)。HALS的优选用量按固态粘合剂计为0.5～2.5％。HALS和紫外线吸收剂与光敏引发剂组合的用途是已知的，例如公开在A.Valet，Lichtschutzmittel für Lacke，Vincentz Verlag，Hannover，1996中。
在后固化中释放出的异氰酸酯基团和与NCO基团发生反应的成分之间的加成反应可按已知的方法借助合适的催化剂如辛酸锡、二月桂酸二丁基锡或叔胺加速。
作为其他的漆添加剂的实例包括：
脱气剂如聚丙烯酸酯，粘合剂如氨基烷基三烷氧基硅烷和均化剂如聚硅氧烷。
除了制备清漆外，通过添加染料或颜料也可制备着色的涂覆剂。正如专业人员已知的，光敏引发剂必须与着色涂覆剂相匹配，例如通过按比例地使用一种具有长波(＞350纳米)吸收带的光敏引发剂。
根据选择的涂覆方法，通过添加溶剂适当地调节涂覆剂的粘度。合适的溶剂是对封闭的异氰酸酯基团和C＝C双键呈惰性的溶剂，如酯、酮、醚、醚酯、烷烃、或芳香溶剂如二甲苯或甲苯。
在按照本发明涂覆底材时，通过一般的工艺例如喷涂、辊涂，刮涂、浇注、涂抹、离心旋涂或浸渍，优选通过喷涂和辊涂将涂覆剂施加在各种底材上。这种底材例如是玻璃、金属如铝板或钢板，必要时对铝板或钢板预处理，金属也可以是所谓的“线圈”，对温度不敏感的木材或塑料，无机材料如水泥、粘土、矿物、陶瓷或由所述的材料制成的已经进行了涂覆的底材，例如汽车或汽车部件。还可涂覆由多种已知材料制成的底材。
按下列步骤对涂覆的涂层系统进行固化：
步骤1：排出任选添加的溶剂。该步骤在室温或高温，优选至80℃进行，也可以采用加热气体的气流(例如空气)进行。可按已知的方法例如红外辐射器或近红外辐射器或按其他方式加热的炉进行升温。
步骤2：进行紫外线固化，适宜的方式是用市场销售的汞高压辐射器或汞中压辐射器辐射。该辐射器也可用其他元素掺杂，优选每厘米灯长的的功率为80～240W。辐射波长为160～400纳米紫外线的Eximer辐射器也是合适的。令人惊奇地发现：虽然该时刻的涂层还含有未交联的成分B)，但已经有了对尘粒是干燥的并且耐许多溶剂的表面。
步骤3：含NCO的成分和与含NCO成分发生反应的成分进行交联。对此，提高涂层温度首先由封闭的异氰酸酯又形成反应性基团，优选NCO基团。反应在高于80℃并且低于450℃的温度下进行。在该温度下涂层的保持时间至少为10秒，优选至少60秒至60分钟，更优选至少2-10分钟。可采用已知方法例如红外辐射器或近红外辐射器或按其他方式加热的炉升高温度。在后固化结束后，在对涂覆体再进行处理前先进行冷却。
令人惊奇地是：在进行后固化时，在NCO基团去封闭形成的和在该温度下挥发的封闭剂对膜或表面无干扰。正如下面的实施例描述的，形成无干扰，外观讲究的涂层。
实施例：
配制下列配方(按重量％)，涂覆并检测。
| 实施例序号 | 1 | 2 | 3 | 4 |
| RoskydalUA VP LS 2266 | 53.13 | 53.94 | ||
| Ebecryl600 | 51.39 | 52.96 | ||
| Irgacure184 | 2.18 | 2.18 | 2.18 | 2.18 |
| DesmodurVP LS 2352 | 30.29 | |||
| DesmodurBL 3370 | 26.96 | |||
| DesmodurVP LS 2307 | 35.70 | |||
| DesmodurBL 3475 | 26.47 | |||
| 乙酸正丁酯 | 14.40 | 16.91 | 10.72 | 18.39 |
| 总量 | 100.0 | 100.0 | 100.0 | 100.0 |
| 固含量大约工作时间，DIN4-杯 | 75.0％70秒 | 75.0％70秒 | 75.0％70秒 | 75.0％70秒 |
说明：
RoskydalUA VP LS 2266(Bayer AG，Leverkusen，德国)-环氧丙烯酸酯，粘度约为8000mPas，分子量约为700g/摩尔，双键密度为5val/kg。
Ebecryl600(UCB GmbH，Kerpen，德国)-基于双酚A树脂的环氧丙烯酸酯，60℃下的粘度约为3000mPas。
Irgacure184(Ciba Spezialitaetenchemie，Lampertheim，德国)-光敏引发剂。
DesmodurVP LS 2352(Bayer AG，Leverkusen，德国)-基于HDI和IPDI的用胺封闭的多异氰酸酯[封闭NCO含量为7.8％，约65％于溶剂石脑油100/1-甲氧基丙基乙酸酯-2/异丁醇(6.4∶14.3∶14.3)中]。
DesmodurBL 3370(Bayer AG，Leverkusen，德国)-基于HDI的用胺和醇封闭的多异氰酸酯[封闭的NCO含量为8.9％，约70％于1-甲氧基丙基乙酸酯中]。
DesmodurVP LS 2307(Bayer AG，Leverkusen，德国)-基于HDI、IPDI和二(异氰酸根合环己基)甲烷的用丙二酸二烷基酯封闭的脂族多异氰酸酯[封闭的NCO含量为6.4％，约60％于异丁醇/1-甲氧基丙基乙酸酯-2 2∶1中]。
DesmodurBL 3475(Bayer AG，Leverkusen，德国)-基于HDI和IPDI的用醇封闭的多异氰酸酯[封闭的NCO含量8.2％，约75％于溶剂石脑油100/乙酸丁酯1∶1中]。
在每2个铝板上刮涂涂覆漆料，在室温下排气5分钟除去大部分溶剂。接着用紫外线进行固化，检测每块涂漆板的稳定性。其他的板在125℃的空气循环炉中干燥87秒。重新检测稳定性。
| 实施例 | 1 | 2 | 3 | 4 |
| 紫外线固化：1Hg高压辐射器120W/cm，带速：5m/分钟 | ||||
| 层厚μm | 6～7 | 6～7 | 6～7 | 5～6 |
| 紫外线干燥后的表面 | 手触干燥 | 手触干燥 | 手触干燥 | 手触干燥 |
| 甲基乙基酮-稳定性* | 0 | 0 | 0 | 0 |
| 异丙醇-稳定性*10％H2O/紫外线固化后15分钟 | 0 | 0 | 0 | 0 |
| 切成网格时的粘附强度* | ||||
| 紫外线干燥后 | 1 | 2 | 3 | 4 |
| 紫外线干燥后+125℃下87秒 | 0 | 0～1 | 0 | 0 |
*0代表很好，5代表差。
Claims (4)
1、一种制备涂层的方法，该方法通过涂布由至少下列组分组成的涂覆剂：
A)至少一种含至少两个(甲基)丙烯酸酯基团的化合物，他们不含异氰酸酯基和封闭的异氰酸酯基，
B)至少一种封闭的多异氰酸酯和
C)至少一种光敏引发剂，接着进行紫外线固化并通过提高涂层的温度进行后固化，其特征在于：组分A)含有至少一种与异氰酸酯基团反应的基团，组分B)不含烯属不饱和基团。
2、根据权利要求1的方法，其特征在于：组分A)具有至多4个烯属不饱和基团。
3、根据权利要求1和2的方法，其特征在于：使用具有至多4个烯属不饱和基团的环氧丙烯酸酯作为组分A)。
4、根据权利要求1～3的方法，其特征在于：用二异丙基胺封闭组分B)的多异氰酸酯。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10054933A DE10054933A1 (de) | 2000-11-06 | 2000-11-06 | Verfahren zur Beschichtung von Substraten |
| DE10054933.0 | 2000-11-06 |
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| Publication Number | Publication Date |
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| CN1535289A true CN1535289A (zh) | 2004-10-06 |
| CN1252116C CN1252116C (zh) | 2006-04-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN01818394.8A Expired - Fee Related CN1252116C (zh) | 2000-11-06 | 2001-10-24 | 制备涂层的方法 |
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| Country | Link |
|---|---|
| US (1) | US6790485B2 (zh) |
| EP (1) | EP1348000B1 (zh) |
| JP (1) | JP4309130B2 (zh) |
| CN (1) | CN1252116C (zh) |
| AT (1) | ATE461951T1 (zh) |
| AU (1) | AU2002223642A1 (zh) |
| CA (1) | CA2427712C (zh) |
| DE (2) | DE10054933A1 (zh) |
| HK (1) | HK1070083A1 (zh) |
| MX (1) | MXPA03003944A (zh) |
| WO (1) | WO2002036657A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1770011B (zh) * | 2004-10-15 | 2010-08-18 | 拜尔材料科学有限责任公司 | 可辐射固化组合物 |
| CN104203992A (zh) * | 2012-03-30 | 2014-12-10 | 太阳控股株式会社 | 聚（甲基）丙烯酸酯的制造方法、由此得到的聚（甲基）丙烯酸酯、单体组合物、其固化物、以及包含其的印刷电路板 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19939760A1 (de) * | 1999-08-21 | 2001-03-08 | Schenectady Int Inc | Verfahren und Vorrichtung zur Isolierung elektrotechnischer Bauteile |
| DE10226933A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Glasfaserverstärkte Kunststoffe |
| DE10226932A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Strahlenhärtende Beschichtungsmittel |
| DE10309669A1 (de) * | 2003-03-06 | 2004-09-16 | Volkswagen Ag | Verfahren zur Trocknung wenigstens einer Lackschicht auf einem Substrat |
| US20050053797A1 (en) * | 2003-06-27 | 2005-03-10 | Rumph Scott W. | Systems and methods for manufacturing, treating, and selling raw building materials |
| DE10344448A1 (de) | 2003-09-25 | 2005-04-28 | Henkel Kgaa | Bindemittel mit Barriere-Eigenschaft |
| US9556355B2 (en) * | 2005-11-29 | 2017-01-31 | BASF Coating GmbH | Paint compositions, method of paint finishing and painted objects |
| DE102006016642A1 (de) * | 2006-04-08 | 2007-10-18 | Bayer Materialscience Ag | UV-härtende Schutzschicht für thermoplastische Substrate |
| US20090176907A1 (en) | 2008-01-08 | 2009-07-09 | Ramesh Subramanian | Direct-to-metal radiation curable compositions |
| US20100183820A1 (en) * | 2009-01-16 | 2010-07-22 | Ford Global Technologies, Llc | Methods for curing uv-curable coatings |
| CN102906206B (zh) | 2010-05-21 | 2016-06-22 | 湛新Ip有限公司 | 低光泽度的可辐射固化的组合物 |
| US10000588B2 (en) * | 2011-07-28 | 2018-06-19 | Eastman Chemical Company | Coating for the inner surface of plastic bottles for protection against degradation from volatile organic compounds |
| EP2821240B1 (en) | 2013-07-02 | 2016-06-01 | Hewlett-Packard Industrial Printing Ltd. | Printing methods |
| CN104945976A (zh) * | 2015-06-18 | 2015-09-30 | 成都纳硕科技有限公司 | 一种地坪用高强度uv固化涂料 |
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| US3256226A (en) * | 1965-03-01 | 1966-06-14 | Robertson Co H H | Hydroxy polyether polyesters having terminal ethylenically unsaturated groups |
| US4366109A (en) * | 1980-05-01 | 1982-12-28 | Freeman Chemical Corporation | Method for making coated molded articles |
| JPS5863760A (ja) | 1981-10-09 | 1983-04-15 | Nippon Paint Co Ltd | 光硬化性被覆組成物 |
| US5229252A (en) * | 1989-06-09 | 1993-07-20 | Morton International, Inc. | Photoimageable compositions |
| EP0501433B1 (en) * | 1991-02-28 | 1997-05-07 | E.I. Du Pont De Nemours And Company | Photosensitive compositions using solvent dispersible interpenetrating polymer networks |
| US6620857B2 (en) * | 1996-07-02 | 2003-09-16 | Ciba Specialty Chemicals Corporation | Process for curing a polymerizable composition |
| DE19646640A1 (de) * | 1996-11-12 | 1998-05-14 | Huels Chemische Werke Ag | Organosol-Polyesterlacke sowie ein Verfahren zu ihrer Herstellung |
| DE19739970A1 (de) * | 1997-09-11 | 1999-03-18 | Basf Ag | Strahlungshärtbare Zubereitungen auf der Basis aliphatischer, Urethangruppen enthaltender Prepolymere mit ethylenisch ungesättigten Doppelbindungen |
| DE19800528A1 (de) | 1998-01-09 | 1999-07-15 | Bayer Ag | Beschichtungssystem aus UV-härtenden Isocyanatgruppen aufweisenden Urethan(meth)acrylatisocyanaten |
-
2000
- 2000-11-06 DE DE10054933A patent/DE10054933A1/de not_active Withdrawn
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2001
- 2001-10-24 CA CA2427712A patent/CA2427712C/en not_active Expired - Fee Related
- 2001-10-24 EP EP01992731A patent/EP1348000B1/de not_active Expired - Lifetime
- 2001-10-24 WO PCT/EP2001/012259 patent/WO2002036657A1/de active Application Filing
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- 2001-10-24 MX MXPA03003944A patent/MXPA03003944A/es active IP Right Grant
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1770011B (zh) * | 2004-10-15 | 2010-08-18 | 拜尔材料科学有限责任公司 | 可辐射固化组合物 |
| CN104203992A (zh) * | 2012-03-30 | 2014-12-10 | 太阳控股株式会社 | 聚（甲基）丙烯酸酯的制造方法、由此得到的聚（甲基）丙烯酸酯、单体组合物、其固化物、以及包含其的印刷电路板 |
| CN104203992B (zh) * | 2012-03-30 | 2016-08-24 | 太阳控股株式会社 | 聚(甲基)丙烯酸酯及制造方法、单体组合物、固化物和印刷电路板 |
| TWI588163B (zh) * | 2012-03-30 | 2017-06-21 | Taiyo Holdings Co Ltd | Poly (meth) acrylate manufacturing method, monomer composition, hardened | cured material, and printed wiring board containing the hardened | cured material |
Also Published As
| Publication number | Publication date |
|---|---|
| US20020081391A1 (en) | 2002-06-27 |
| HK1070083A1 (en) | 2005-06-10 |
| MXPA03003944A (es) | 2004-02-12 |
| CA2427712C (en) | 2010-12-21 |
| EP1348000B1 (de) | 2010-03-24 |
| JP4309130B2 (ja) | 2009-08-05 |
| DE50115409D1 (de) | 2010-05-06 |
| ATE461951T1 (de) | 2010-04-15 |
| US6790485B2 (en) | 2004-09-14 |
| JP2004513197A (ja) | 2004-04-30 |
| WO2002036657A1 (de) | 2002-05-10 |
| EP1348000A1 (de) | 2003-10-01 |
| CA2427712A1 (en) | 2003-05-02 |
| DE10054933A1 (de) | 2002-05-08 |
| AU2002223642A1 (en) | 2002-05-15 |
| CN1252116C (zh) | 2006-04-19 |
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