CN109265582A - 低温液态胺基酮型光引发剂化合物及其混合物 - Google Patents
低温液态胺基酮型光引发剂化合物及其混合物 Download PDFInfo
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- CN109265582A CN109265582A CN201710604216.2A CN201710604216A CN109265582A CN 109265582 A CN109265582 A CN 109265582A CN 201710604216 A CN201710604216 A CN 201710604216A CN 109265582 A CN109265582 A CN 109265582A
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/10—Epoxy resins modified by unsaturated compounds
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
Abstract
本发明涉及光固化(UV‑Curing)新材料化学品领域,首次披露了近室温温度下为液态的胺基酮型光引发剂,含有该胺基酮的光引发剂混合物,其在含烯键不饱和型可辐射聚合体系作为光引发剂的用途,以及含有这种光引发剂或其混合物组分的含烯键不饱和型可辐射聚合体系。
Description
【技术领域】
本发明涉及光固化(UV-Curing)新材料化学品领域,首次披露了低温下为液态的胺基酮型光引发剂,含有该胺基酮的光引发剂混合物,其在含烯键不饱和型可辐射聚合体系作为光引发剂的用途,以及含有这种光引发剂或其混合物组分的含烯键不饱和型可辐射聚合体系。
【背景技术】
在光固化新材料技术领域,光引发剂(Photo-initiator)是吸收UV辐射光源能量而产生活性自由基或阳离子酸等聚合引发物种的关键材料。胺基酮型(Aminoketone)光引发剂是极为重要的一大类高活性光引发剂,代表性商业化牌号产品例如前汽巴(Ciba)公司推出的Irgacure 907,Irgacure 369,和Irgacure 379,以及深圳有为化学技术公司产业化的牌号为APi-307(化学结构1-(biphenyl-4-yl)-2-methyl-2-morpholinopropan-1-one,CAS号码94576-68-8)的新型胺基酮型光引发剂。
在该技术领域,在兼具高超引发活性和其它功效-特别是耐黄变和低残留不良气味-的情况下,为从业专业人员所渴望的,鉴定和发现在近室温温区附近(15-45℃)为液态的胺基酮光引发剂化合物尤其具备突出的实用应用价值。因为已知的胺基酮型光引发剂化合物均是固体状态,光固化涂料或油墨厂家在使用时不得不借助各种化学或物理的办法(例如研磨,搅拌,超声等)取得相关光引发剂在配方产品中的合适的溶解性和/或分散性,这常常是操作不方便和较高不利成本的过程。例如,Irgacure 379即是汽巴公司专门为改善Irgacure 369的难溶解性而推出的结构衍生物产品。
近室温温区为液态的光引发剂在实际应用时稍加微热即融化为液态,非常便于计量和添加,也没有配方制备中常见的分散或溶解等困扰性过程,是尤为从业技术人员所喜爱的。文献中有相当数量的液态光引发剂混合物的报道【例如汽巴推出的牌号产品Irgacure 500(固体羟基酮型和固体二苯甲酮型光引发剂的液态混合物)和Irgacure 2022(液体羟基酮型和固体膦酰型光引发剂的液态混合物),以及专利文献披露US4960746和US5510539】,其目的即是为用户提供操作友好型的光引发剂产品。
值得强调的是,迄今为止,业界尚未有任何关于近室温温区附近(15-45℃)液态小分子胺基酮型光引发剂的文献报道。鉴于已知的化学理论尚无法理性预测一个化合物的物理存在形式和状态,因此鉴定和发现在近室温温区附近温度区域下呈现液态和/或高溶解性能的胺基酮型光引发剂化合物必须通过大量的试验摸索和试错实现。
【发明内容】
本项申请现已首次意外地发现,下述A-C所示的三个胺基酮结构是近室温温区(15-45℃)为液态的光引发剂化合物。
我们同时披露一类新颖的光引发剂混合物。如果该光引发剂混合物以100%质量份计,其特征是含有a百分质量份的光引发剂A,B,C三者之中任意一种或二种或以上,b百分质量份的其他文献已知光引发剂物质,以及c百分质量份的其他物质;其他物质是指其他文献已知含烯键(C=C)不饱和化合物(单体或树脂),活性胺助引发剂,或各种功能性添加剂。约束条件是:
(1)a+b+c三者之和是100%质量份;
(2)a和b取值均不为零,c取值可以为零或非零。
所述文献已知光引发剂是下述任意一种光引发剂化合物或任意两种或两种以上光引发剂化合物组成的复配混合物:羟基酮型(Hydroxyketones),胺基酮型(Aminoketones),膦酰型(Acylphosphine Oxides),肟酯型(Oxime Esters),二苯甲酮型(Benzophenones),苯甲酰甲酸酯型(Phenylglyoxylates),硫杂蒽酮型(Thioxanthones),鎓盐型阳离子光引发剂(Sulfoniums或Iodoniums或Photo-Acid Generators,即所谓PAGs),或染料作为实质性光敏化剂(Dye Sensitizers)的光引发剂物质。光引发剂的例子是Darocur 1173,Irgacure 184,APi-307(深圳有为化学公司产品,CAS号码94576-68-8),APi-180(深圳有为化学公司产品,CAS号码1308332-52-6),Irgacure 2959,Irgacure MBF,Irgacure 127,Irgacure 651,Esacure KIP-150,Esacure KIP-160,Esacure KIP-1001,Esacure 01,Irgacure 907,Irgacure 500,Irgacure 2200,Irgacure 2022,Irgacure4500,Irgacure 369,Irgacure 379,Irgacure 819,Irgacure TPO,Irgacure TPO-L,BP,PBZ,甲基或乙基米蚩酮,Esacure TZT,Irgacure 754,Irgacure ITX,Irgacure DETX,Irgacure CPTX,Irgacure OXE-01,Irgacure OXE-02,Irgacure OXE-03,Irgacure 250,ADEKA NCI-831,ADEKA N-1414,Irgacure 290,Irgacure 270,以及香豆素型染料光敏化剂等,上述体系也可以复配相应的助引发剂(Co-initiator),例如活性胺和/或氢硅烷类活性氢给体型助引发剂。
所述含烯键不饱和化合物(单体)是任何含烯键可聚合单体,包括但不限于(甲基)丙烯酸酯,丙烯醛,烯烃,共轭双烯烃,苯乙烯,马来酸酐,富马酸酐,乙酸乙烯酯,乙烯基吡咯烷酮,乙烯基咪唑,(甲基)丙烯酸,(甲基)丙烯酸衍生物例如(甲基)丙烯酰胺,乙烯基卤化物,亚乙烯基卤化物等。
所述含烯键不饱和化合物(树脂)是任何含烯键预聚物和低聚物,包括但不限于(甲基)丙烯酰官能基的(甲基)丙烯酸共聚物,聚氨酯甲酸酯(甲基)丙烯酸酯,聚酯(甲基)丙烯酸酯,不饱和聚酯,聚醚(甲基)丙烯酸酯,硅氧烷(甲基)丙烯酸酯,环氧树脂(甲基)丙烯酸酯等,以及上述物质的水溶性或水分散性的类似物。
所述功能性添加剂是合适的各类添加剂,为本领域技术人员所知晓的是如下各类添加剂,包括但不限于阻聚剂,活性胺助引发剂,流平剂,消泡剂,抗流挂剂,增稠剂,增粘剂,分散剂,抗静电剂,增溶剂,稀释剂,水或有机溶剂,抗菌剂,阻燃剂,无机或有机填充剂(例如纳米氧化铝,二氧化硅,碳酸钙,硫酸钡等)和/或着色剂(例如颜料或染料等),增强涂料油墨耐候性的紫外线吸收剂或/和光稳定剂,及上述组分的合适的水性分散体或水溶解性产品。
进一步的,我们披露一类新型的UV辐射固化材料配方体系,其特征是:
(3)含有至少一种A-C定义的光引发剂或其混合物;
(4)含有至少一种含烯键不饱和化合物(单体和/或树脂)。
所述的含烯键不饱和化合物(单体和/或树脂)定义与上相同。
本发明披露的上述新型UV辐射固化材料配方体系,包括光固化涂料或油墨材料,配合各种不同的施工方式(例如喷涂,滚涂,淋涂,擦涂,浸涂等)和/或施工工序(例如腻子,底涂,上色,中涂,面涂等),在木器家具,塑胶产品,印刷包装,喷墨打印,电子消费品,机动车辆内外饰,管道型材,工业地坪,建筑幕墙,3D打印增材制作,以及船舶或集装箱体等下游市场均具有极为广阔的应用价值。特别有价值的示例性而非限定性应用例如,该等涂料或油墨用于制备着色和未着色的油漆和清漆、粉末涂料、印刷油墨、印版、胶粘剂、压敏胶粘剂、牙科组合物、凝胶涂料、电子器件用光致抗蚀剂、电锻抗蚀剂、蚀刻抗蚀剂、液态和干膜二者、焊接抗蚀剂、制造用于各种显示器应用的滤色器的抗蚀剂,制备等离子显示面板的制造方法中的结构、电致发光显示器和LCD的抗蚀剂,用于LCD、全息数据储存,用于包封电子组件的组合物,用于制备磁记录材料、微机械部件、波导、光学开关、锻覆掩膜、蚀刻掩膜、彩色打样体系、玻璃纤维电缆涂料、丝网印刷模版,用于借助立体光刻产生三维物体,作为图像记录材料,用于全息记录、微电子电路、脱色材料,用于图像记录材料的脱色材料,用于使用微胶囊的图像记录材料,作为光致抗蚀剂材料用于UV和可见激光直接成像体系,作为光致抗蚀剂材料用于形成印刷电路板的依序构建层中的介电层;特别地,使用上文所述的可光聚合组合物来制备着色和未着色的油漆和清漆、粉末涂料、印刷油墨(例如丝网印刷油墨、用于胶版、柔版或喷墨印刷的油墨)、印版、胶粘剂、密封件、灌封组分、牙科组合物、泡沫、模制复合物、复合材料组合物、玻璃纤维电缆涂料、丝网印刷模版,用于借助立体光刻产生三维物体,和作为图像记录材料、光致抗蚀剂组合物、脱色材料、用于图像记录材料的脱色材料,用于使用微胶囊的图像记录材料。
在实施例中我们将进一步说明。
【具体实施方式】
下面结合具体实施例进一步说明本发明要旨:
实施例一:1-([1,1′-biphenyl]-4-yl)-2-(diethylamino)-2-methylpropan-1-one
在氩气保护下,将30克联苯氯代异丁酮【1-([1,1′-biphenyl]-4-yl)-2-chloro-2-methylpropan-1-one,商业采购自荆门美邦化学有限公司】和17.5克二乙胺,3.8克无水三氯化铝混合于120毫升甲苯中,体系升温至75摄氏度搅拌反应4小时。薄层色谱TLC检测原料消失反应结束(展开剂为乙酸乙酯/正己烷=1/20)。停止反应后过滤,滤饼用50毫升甲苯打浆洗涤,收集所有滤液后减压脱除回收甲苯,粗产品直接减压蒸馏得到淡黄色清亮液体产品,收率92%。
该液体久置固化后测得熔点为40.5-41.5℃。
1H-NMR(CDCl3):δ=8.64-8.62(m,2H),7.68-7.62(m,4H),7.47-7.33(m,3H),2.61(q,4H),1.39(s,6H),1.11(t,6H);13C-NMR(CDCl3):δ=203.4(C=O signal),144.6,140.2,134.7,131.2,128.8,127.9,127.1,126.2,69.6,44.4,21.9,15.9ppm;
实施例二:1-([1,1′-biphenyl]-4-yl)-2-(bis(2-hydroxyethyl)amino)-2-methyl pro-pan-1-one
参考实施例一操作,在氩气保护下,将29.5克联苯氯代异丁酮和26.4克二乙醇胺,4.2克无水三氯化铝混合于120毫升甲苯中,体系升温至85摄氏度搅拌反应过夜后冷却到室温抽滤,滤饼用50毫升甲苯打浆洗涤,收集所有滤液后减压脱除回收甲苯,粗产品在硅胶柱色谱上用乙酸乙酯/己烷梯度洗脱得到黄色粘稠液体产品,收率72%。
HRMS(M+H)for C20H26O3N:328.1913(calculated),328.1925(experimental);(M+Na)for C20H25NaO3N:350.1732(calculated),350.1738(experimental)。
实施例三:1-([1,1′-biphenyl]-4-yl)-2-(dimethylamino)-2-methylpropan-1-one
参考实施例一操作,在一个Parr压力反应器中,将24.6克联苯氯代异丁酮,3.1克无水三氯化铝,100毫升甲苯,和气瓶导入的26毫升二甲胺混合后并密封体系,该体系升温至75摄氏度搅拌反应6小时。停止反应释放压力后过滤,滤饼用20毫升甲苯打浆洗涤,收集所有滤液后减压脱除回收甲苯,粗产品直接减压蒸馏得到淡黄色液体产品,收率83%。
实施例四:应用试验
含烯键(丙烯酸酯)UV辐射固化材料配方体系样品按下列配方制作(以重量百分比计):双酚A环氧丙烯酸酯(Ebecryl 605):32%;氨基丙烯酸酯(Ebecryl 7100):10%;丙烯酰吗啉:54%;光引发剂:4%。
光固化性能评估:将上述实施例样品涂覆于卡纸板上形成约20微米的涂层,以UV高压汞灯为辐照光源,变速传送带试验。以指甲反复压刻刮擦不产生印迹为光聚合固化完成的判据。结果如下:
当光引发剂是胺基酮A时,光固化完全最大线速度为40米/分钟;
当光引发剂是胺基酮B时,光固化完全最大线速度为40米/分钟;
当光引发剂是胺基酮C时,光固化完全最大线速度为40米/分钟;
当光引发剂是含胺基酮A的混合物(其中a=70%和b=30%且b为Irgacure ITX)时,光固化完全最大线速度为60米/分钟;
当光引发剂是含胺基酮A的混合物(其中a=50%和b=50%且b为深圳有为化学公司APi-307)时,光固化完全最大线速度为45米/分钟;
当光引发剂是含胺基酮A的混合物(其中a=50%和b=50%且b为Darocur TPO)时,光固化完全最大线速度为50米/分钟;
当光引发剂是含胺基酮A的混合物(其中a=90%和b=10%且b为Irgacure OXE-02)时,光固化完全最大线速度为75米/分钟;
当光引发剂是含胺基酮A的混合物(其中a=60%和b=40%且b为Irgacure 1173)时,光固化完全最大线速度为30米/分钟。
需要强调的是,上述实施例仅仅为示例性而非限定性说明,基于本项申请披露,任何从业技术人员所通常可能采用的反应条件或参数等调整或变动均不会偏离本发明的要旨,本专利的保护范围应以相关的权利书记载条目为准。
Claims (5)
1.下述A-C所示的三个近室温温区(15-45℃)下为液态的胺基酮型结构化合物:
2.下述A-C所示的三个近室温温区(15-45℃)下为液态的胺基酮型结构化合物作为UV光固化光引发剂(Photo-initiator)或材料添加剂(Additive)或有机合成叔胺原料或合成子(Synthon)的用途:
3.一类光引发剂混合物,以该光引发剂混合物100%质量份计,其特征是含有a百分质量份的光引发剂A,B,C三者之中任意一种或二种或以上,b百分质量份的其他文献已知光引发剂物质,以及c百分质量份的其他物质;其他物质是指文献已知含烯键(C=C)不饱和化合物(单体或树脂),活性胺助引发剂,或各种功能性添加剂。约束条件是:
(1)a+b+c三者之和是100%质量份;
(2)a和b取值均不为零,c取值可以为零或非零。
所述文献已知光引发剂是下述任意一种光引发剂化合物或任意两种或两种以上光引发剂化合物组成的复配混合物:羟基酮型(Hydroxyketones),胺基酮型(Aminoketones),膦酰型(Acylphosphine Oxides),肟酯型(Oxime Esters),二苯甲酮型(Benzophenones),苯甲酰甲酸酯型(Phenylglyoxylates),硫杂蒽酮型(Thioxanthones),鎓盐型阳离子光引发剂(Sulfoniums或Iodoniums或Photo-Acid Generators,即所谓PAGs),或染料作为实质性光敏化剂(Dye Sensitizers)的光引发剂物质。光引发剂的例子是Darocur 1173,Irgacure184,APi-307(深圳有为化学公司产品,CAS号码94576-68-8),APi-180(深圳有为化学公司产品,CAS号码1308332-52-6),Irgacure 2959,Irgacure MBF,Irgacure 127,Irgacure651,Esacure KIP-150,Esacure KIP-160,Esacure KIP-1001,Esacure 01,Irgacure 907,Irgacure 500,Irgacure 2200,Irgacure 2022,Irgacure 4500,Irgacure 369,Irgacure379,Irgacure 819,Irgacure TPO,Irgacure TPO-L,BP,PBZ,甲基或乙基米蚩酮,EsacureTZT,Irgacure 754,Irgacure ITX,Irgacure DETX,Irgacure CPTX,Irgacure OXE-01,Irgacure OXE-02,Irgacure OXE-03,Irgacure 250,ADEKA NCI-831,ADEKA N-1414,Irgacure 290,Irgacure 270,以及香豆素型染料光敏化剂等,上述体系也可以复配相应的助引发剂(Co-initiator),例如活性胺和/或氢硅烷类活性氢给体型助引发剂。
所述含烯键不饱和化合物(单体)是任何含烯键可聚合单体,包括但不限于(甲基)丙烯酸酯,丙烯醛,烯烃,共轭双烯烃,苯乙烯,马来酸酐,富马酸酐,乙酸乙烯酯,乙烯基吡咯烷酮,乙烯基咪唑,(甲基)丙烯酸,(甲基)丙烯酸衍生物例如(甲基)丙烯酰胺,乙烯基卤化物,亚乙烯基卤化物等。
所述含烯键不饱和化合物(树脂)是任何含烯键预聚物和低聚物,包括但不限于(甲基)丙烯酰官能基的(甲基)丙烯酸共聚物,聚氨酯甲酸酯(甲基)丙烯酸酯,聚酯(甲基)丙烯酸酯,不饱和聚酯,聚醚(甲基)丙烯酸酯,硅氧烷(甲基)丙烯酸酯,环氧树脂(甲基)丙烯酸酯等,以及上述物质的水溶性或水分散性的类似物。
所述功能性添加剂是合适的各类添加剂,包括但不限于阻聚剂,活性胺助引发剂,流平剂,消泡剂,抗流挂剂,增稠剂,增粘剂,分散剂,抗静电剂,增溶剂,稀释剂,水或有机溶剂,抗菌剂,阻燃剂,无机或有机填充剂(例如纳米氧化铝,二氧化硅,碳酸钙,硫酸钡等)和/或着色剂(例如颜料或染料等),增强涂料油墨耐候性的紫外线吸收剂或/和光稳定剂,及上述组分的合适的水性分散体或水溶解性产品。
4.根据权利要求(2-3)描述的化合物及其混合物作为含烯键不饱和型可辐射聚合体系的光引发剂的用途。
5.一类新型的UV辐射固化材料配方体系,其特征是:
(1)含有至少一种A-C定义的光引发剂或其混合物;
(2)含有至少一种含烯键不饱和化合物(单体和/或树脂)。
所述的含烯键不饱和化合物(单体和/或树脂)的定义与权利要求(3)中定义相同。
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