CN1268664C - 树脂组合物,耐焊组合物,以及由此得到的固化物 - Google Patents
树脂组合物,耐焊组合物,以及由此得到的固化物 Download PDFInfo
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- CN1268664C CN1268664C CNB02815438XA CN02815438A CN1268664C CN 1268664 C CN1268664 C CN 1268664C CN B02815438X A CNB02815438X A CN B02815438XA CN 02815438 A CN02815438 A CN 02815438A CN 1268664 C CN1268664 C CN 1268664C
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Classifications
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C08G59/625—Hydroxyacids
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- H—ELECTRICITY
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- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
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- H—ELECTRICITY
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Abstract
光敏性和显影性极佳的树脂组合物,其生成的固化物具有极佳的柔软性,耐焊接热,耐热退化和耐无电镀金,尤其适合用在形成耐焊接层和夹层电介质。树脂组合物以含有低聚物(A)为特征,它通过反应下列成分(a)-(d)得到;每个分子具有至少两个环氧基团的环氧树脂,每个分子具有两个羟基和一个羧基的化合物,羧酸化的橡胶状聚合物,以及具有不饱和基团的一元酸。
Description
技术领域
本发明涉及树脂组合物及其固化物,它们可应用于各种涂层材料,表面处理材料,用于波导管、层压板、粘合剂、粘着剂、印刷油墨、密封剂、耐色剂、(用在LCDs和CCDs中)以及耐液体油墨中的材料,特别有用的是在印刷电路板组合物中。更具体地说,本发明涉及的树脂组合物具有极佳的显影性质,适当地将其作为耐焊剂用在柔软性印刷板、耐电镀及使用夹层电绝缘材料的多层印刷电路板中,显影后可得到形成涂层薄膜形状的固化物,其在粘结力、柔软性(弯曲性),耐焊接热,耐化学性,耐无电镀金方面都很优秀。
背景技术
为了保护通过网板印刷方法在基物上形成的接线(电路)图形等使其不受外部环境侵害,以及也是为了在印刷电路板上表面组装电部件时而进行的焊接过程中,通常在印刷电路板上施加保护层,称为覆盖涂层或焊锡罩,以防止焊锡粘合到不需要的部件。
通常,有关为此而使用的耐焊油墨,主要使用多官能的环氧树脂为基础的油墨;然而,这种油墨的问题是:虽然它提供优良的耐热性,形成固化薄膜的柔软性不好。因此,这种类型的耐焊接油墨限制在不要求柔软性的刚性板中,将这种油墨应用在近年广泛使用的柔软性印刷电路板(FPC)中,是困难的。
在这些情况下,最近提出了有柔软性的各种耐焊油墨。例如,日本专利申请公开号2-269166,揭示了聚仲班酸制造的热固型耐焊树脂,环氧树脂和极性溶剂,JP-A 6-41485揭示了使用聚仲班酸和苯氧基树脂作为主要组分的热干型的耐焊油墨。然而,这些耐焊剂是通过使用网板印刷方法,作为耐焊图形而形成的,结果:在网板的线宽度等方面存在限制;因此它们不能提供符合当前高密度要求的精细图像形成方法。为此,在最近几年,提出照相显影型,如JP-A 2-172749,JP-A2-173750和JP-A 173751揭示的;然而,它们没有达到充分的柔软性。
本发明的目标是提供树脂组合物及其固化物,树脂组合物,通过使用特殊的低聚物(A)形成,即使使用的聚合引发剂的量小于通常使用的量时,具有优秀的可固化性(光敏性),即使其酸值(毫克KOH/克)小于常规的酸值,具有极佳的显影性,并提供固化的薄膜,在后固化过程中通过热固化树脂组合物得到,形成的固化薄膜具有优良的柔软性,具有极佳的耐焊接热,耐热变形,耐无电镀金,耐酸和抗水性,树脂组合物也适合应用于有机溶剂或碱性显影性油墨,尤其,适用于柔性印刷电路板的耐焊油墨。
发明的揭示内容
为了解决上面提到的问题,本发明的发明人发现:应用含特殊低聚物(A)的树脂组合物,使解决上面提到的问题成为可能,并设计了本发明。
换句话说,本发明涉及的树脂组合物包含:
(1)使下列组分(a)-(d)相互反应得到的低聚物(A):
(a)具有至少两个环氧基团/分子的环氧树脂;
(b)具有两个羟基和一个羧基/分子的化合物;
(c)羧酸酯化的橡胶状聚合物;
(d)具有不饱和基团的一价酸。或
(2)使下列化合物(a)-(e)相互反应得到的低聚物(A):
(a)具有至少两个环氧基团/分子的环氧树脂;
(b)具有两个羟基和一个羧基/分子的化合物;
(c)羧酸酯化的橡胶状聚合物;
(d)具有不饱和基团的一元酸;
(e)多元酸酐;
(3)上面提到的(1)或(2)中所述的树脂组合物,其中低聚物(A)的平均分子量在1000-100000的范围。
(4)上面提到的(1)-(3)之一中所述树脂组合物,其中低聚物(A)具有的酸值在1-300毫克KOH/克的范围。
(5)上面提到的(1)-(4)之一中所述树脂组合物,其中,具有至少两个环氧基团/分子的环氧树脂(1)由下列分子式表示:
(在分子式(1)中,X是-CH2-或-C(CH3)2-,m是1或以上的整数,M是氢原子或下列分子式(G)表示的基团:
在此,在m是1情况下,M由分子式(G)表示,在m大于1的情况下,至少一个M由分子式(G)表示,其他的是氢原子。
(6)上面(5)中描述的树脂组合物,其中,在分子式(1)中,由分子式(G)表示的M的比在70-90摩尔的范围;
(7)上面提到的(1)-(6)之一中所述树脂组合物,其中,每个分子具有两个羟基和一个羧基的化合物(b)是具有2-6个碳原子的羧酸的二羟甲基化的化合物。
(8)上面提到的(1)-(7)之一中所述树脂组合物,其中具有不饱和基团的一元酸(d)是一种或两种或两种以上选自(甲基)丙烯酸和含马来酰亚胺基团的一元酸的化合物,
(9)上面提到的(2)中描述的树脂组合物,其中多元酸酐(e)是邻苯二甲酸酐衍生物,
(10)上面提到的(1)-(9)之一中所述树脂组合物,含有光-聚合引发剂(C),
(11)上面提到的(1)-(11)之一中所述树脂组合物,含有热固化组分(D),
(12)上面提到的(11)中所述树脂组合物,其中热固化组分(D)是环氧树脂,
(13)上面提到的(12)中所述树脂组合物,含有1,4-二氢吡啶衍生物,作为环氧树脂的固化加速剂,
(14)上面提到的(1)-(13)之一中所述树脂组合物,含有稀释剂(B),
(15)含上面(14)中描述的树脂组合物的组合物,用于印刷电路板的耐焊层或中间隔离层,
(16)上面提到的(1)-(15)之一中所述树脂组合物的固化制品,
(17)具有上面提到的(16)中所述固化制品的产品,
(18)上面提到的(17)中描述的产品,它是印刷电路板。
执行本发明的最佳模式
下面的描述将详细讨论本发明。这里,在下面的描述中,“部分”和“%”分别表示“重量份”和“重量%”,除非另行定义。
本发明的树脂组合物含有低聚物(A),使用低聚物的分子量优选设定在1000-100000重量-平均分子量的范围,其酸值优选设定在1-300毫克KOH/克的范围内。
本发明中使用的低聚物(A)是下列组分相互反应得到的反应产物:具有至少两个环氧基团/分子的环氧树脂,具有两个羟基和一个羧基/分子的化合物(b),羧酸酯化的橡胶状聚合物(c),含不饱和基团的一元酸,作为任选组分的多元酸酐(e)。
关于使用的含有至少两个环氧基团/分子的环氧树脂(a),其具体例子包括酚醛清漆型环氧树脂(如:由各种酚,如苯酚,甲酚,卤代的苯酚和烷基苯酚与甲醛在酸性催化剂存在下反应得到的酚醛清漆树脂与表氯醇和/或甲基表氯醇反应所得到的那些产物)。关于市售产品,它们的例子包括EOCN-103,EOCN-140S,EOCN-1020,EOCN-1027,EPPN-201和BREN-S,由Nippon Kayaku Co.,Ltd.制造,DEN-431和DEN-439,Dow Chemical Company制造;N-730,N-770,N-865,N-665,N-673和VH-4150,Dainippon Ink and Chemicals,Incorporated制造等)双酚型环氧树脂(例如,使各种双酚,如双酚A,双酚F,双酚S和四溴双酚A,与表氯醇和/或甲基表氯醇反应得到的),上面分子式(1)所表示的环氧树脂,它们是通过使双酚A和双酚F的甘油醚,即上面提到的双酚和表氯醇和/或甲基表氯醇的缩合物,相互反应得到的。关于市售产品,它们的例子包括Epicoat 1004和Epicoat 1002,Yuka Shell K.K制造;DER-330和DER-337,Dow Chemical Company制造,三苯酚甲烷型环氧树脂(例如,使三苯酚甲烷,三甲酚甲烷等,与表氯醇和/或甲基表氯醇反应得到的)。关于市售产品,它们的例子包括EPPN-501,EPPN-502等,三(2,3-环氧丙基)异氰尿酸酯,联苯基二缩水甘油醚和其它材料,如含脂环族氨基的环氧树脂,如Celloxide 2021,Daicel Chemical Industries,Ltd.制造;EpomicVG-3101,Mitsui Petrochemical Industries,Ltd制造;TETRAD-X及TETRAD-C,Mitsubishi Gas Chemical Company,Inc.制造;及EPB-13,EPB-27等,NipponSoda Co.,Ltd.制造,共聚型环氧树脂(例如,甲基丙烯酸二缩水甘油酯和苯乙烯的共聚物,甲基丙烯酸二缩水甘油酯,苯乙烯和甲基丙烯酸甲酯的共聚物,即,CP-50M和CP-50S,Nippon Oil & Fats Co.,Ltd.制造,或甲基丙烯酸缩水甘油酯和环己基马来酰亚胺的共聚物),或其它具有特殊结构的环氧树脂及类似物。它们中尤其优选的例子是上面提到的分子式(1)表示的环氧树脂等。尤其,在分子式(1)中,优选使用M是缩水甘油基的比设定在70-90摩尔%的那些树脂。
接着,关于每个分子有两个羟基和一个羧基的化合物(b),它们的例子包括羧酸的二羟甲基化的化合物,具体例子包括有2-6个碳原子的羧酸的二羟甲基化的化合物,优选2-4个碳的羧酸,比如二羟甲基丙酸,二羟甲基乙酸,二羟甲基丁酸,二羟甲基戊酸和二羟甲基己酸。
此外,关于羧酸酯化的橡胶状聚合物(c),虽然它的结构没有特殊限制,它的例子包括羧酸基团加到下列各共聚物分子的两个终端,或加到直链聚合物分子的两个终端的橡胶状聚合物,共聚物的例子是:共轭二烯为基础的乙烯基单体和烯型的不饱和一元酸之间的共聚物,比如丁二烯-丙烯酸共聚物;共轭二烯为基础的乙烯基单体,烯型的不饱和一元酸和另一个乙烯基单体的共聚物,比如丁二烯-丙烯腈-丙烯酸共聚物;悬挂羧酸的共轭二烯为基础的乙烯基共聚物,比如马来聚丁二烯,由下式1或2典型地表示。
结构式1
(在这分子式中,n和1分别表示重复的平均单位数,并且是整数1以上。)
结构式2
(在这分子式中,a,b,c分别表示重复的平均单位数,并且是整数1以上。)
关于上面提到的有羧基加到直链聚合物分子的两个终端的橡胶状聚合物,它们的例子包括有羧基加到聚丁二烯二酸酸分子的两个终端的二烯为基础的乙烯基聚合物,例如下面结构分子式3表示的;羧基加到两个分子终端的聚合物,它是共轭二烯为基础的乙烯基单体和烯的不饱和一元酸之间的共聚物,比如有羧基加到丁二烯-丙烯腈共聚物的两个分子终端的聚合物,由下列结构式4表示(例如,HYCAR CTBN 1300×13(B.F.Good rich chemical Co.,Ltd.制造)分子量3500,27%键合的丙烯腈,1.9羧基/分子);共轭二烯为基础的乙烯基聚合物和酸酐之间的半酯,比如聚丁二烯甘醇和马来酸酐的共聚物,由下列结构式5表示。
结构式3
(在这分子式中,e表示重复的平均单位数,并且是整数1以上。)
结构式4
(在这分子式中,f和g分别表示重复的平均单位数,并且是整数1以上。)
结构式5
(在这分子式中,h表示重复的平均单位数,并且是整数1以上。)
这里,关于上面提到的羧酸化橡胶状聚合物中使用的共轭二烯为基础的乙烯基聚合物,代替上面简化的衍生自丁二烯的聚合物,可使用衍生自异戊二烯,氯丁二烯等的聚合物。而且,它们中的每一个可与共轭的二烯为基础的乙烯基单体共聚。关于烯型的饱和一元酸,它们的例子包括(甲基)丙烯酸,丁烯酸,肉桂酸,丙烯酸二聚物,马来酸一甲酯,马来酸一丙酯,马来酸一丁酯,马来酸一(2-乙基己)酯和山梨酸,它们中,优选使用(甲基)丙烯酸。关于其它乙烯基单体,可使用丙烯酸,甲基丙烯酸,丙烯腈,苯乙烯,乙烯基甲苯等。
另外,关于橡胶状聚合物中羧基的数目,虽然没有特别的限制,羧基的数目设定在1-5的范围,优选平均1.5-3/分子。
关于有一个不饱和基团的一元酸(d)的特殊例子,包括不饱和一元羧酸,比如(甲基)丙烯酸,丙烯酸二聚物,β-苯乙烯基丙烯酸,β-糠基丙烯酸,丁烯酸,α-氰基肉桂酸和肉桂酸。它们的例子还包括:饱和或不饱和二元酸酐和含一个羟基/分子的(甲基)丙烯酸酯之间的反应产物,饱和或不饱和二元酸和含一个不饱和基团的一缩水甘油基化合物之间的反应产物,以及饱和及不饱和二元酸与含一个不饱和基的一缩水甘油基化合物之间的反应产物半酯,在等摩尔基础上,使前者和后者相互反应,可得到它们。这里,关于饱和或不饱和二元酸酐,其例包括琥珀酸酐,马来酸酐,邻苯二甲酸酐,四氢邻苯二甲酸酐,六氢邻苯二甲酸酐,甲基六氢邻苯二甲酸酐,甲基四氢邻苯二甲酸酐,衣糠酸酐和甲基桥亚甲基四氢邻苯二甲酸酐。另外,关于(甲基)丙烯酸,它们的例子包括有一个羟基/分子的甲基丙烯酸酯,比如羟乙基(甲基)丙烯酸酯,羟丙基(甲基)丙烯酸酯,羟丁基(甲基)丙烯酸酯,聚(甲基)丙烯酸乙二醇单酯,甘油二(甲基)丙烯酸酯,三羟甲基丙烷二(甲基)丙烯酸酯,季戊四醇三(甲基)丙烯酸酯,二季戊四醇五(甲基)丙烯酸酯和苯基缩水甘油醚的(甲基)丙烯酸酯。另外,关于饱和或不饱和的二元酸,例子包括:丁二酸,马来酸,己二酸,苯二酸,间苯二酸,四氢苯二酸,六氢苯二酸,衣康酸和富马酸。关于含不饱和基团的一缩水甘油化合物,例子包括下列(甲基)丙烯酸缩水甘油酯:
另外,除上面所述以外的含不饱和基团的一元酸(d)的例子,包括含马来酰亚胺基团的一元酸。关于含马来酰亚胺基团的一元酸,如下面分子式表示的,第一个例子是化合物(d-1),可通过使用已知的技术,从马来酸酐和伯氨基羧酸合成[参见D.H.Rich等人写的“Journal of Medical Chemistry”第18卷,1004-1010页(1975年)]。第二个例子是马来酰亚胺化合物([1])和具有一个酸酐基团/分子的化合物([2])之间的半酯化合物(d-2)。
关于上面所述的伯氨基羧酸,例子包括:天冬酰胺,丙氨酸,β-丙氨酸,精氨酸,异白氨酸,甘氨酸,谷氨酰胺,色氨酸,苏氨酸,缬氨酸,苯基丙氨酸,高苯基丙氨酸,α-甲基苯基丙氨酸,赖氨酸,白氨酸,环白氨酸,3-氨基丙酸,α-氨基丁酸,4-氨基丁酸,氨基戊酸,6-氨基己酸,7-氨基庚酸,2-氨基辛酸,3-氨基辛酸,6-氨基辛酸,8-氨基辛酸,9-氨基壬酸,2-氨基癸酸,9-氨基癸酸,15-氨基十五烷酸,2-氨基十六烷酸和16-氨基十六烷酸,但并不限制于这些。
关于含羟基基团的马来酰亚胺化合物([1]),例如,使用从马来酰亚胺和甲醛合成的化合物,如下列分子式所表示:
反应式
另外,建议使用通过已知技术(例如参见美国专利号2526517,JP-A号2-268155等),从马来酸酐和伯氨基醇合成的化合物,如下列分子式所表示;这些化合物含有马来酰亚胺基团和一个羟基/分子。
反应式
关于上面所述的伯氨基醇,例子包括:2-氨基乙醇,1-氨基-2-丙醇,3-氨基1-丙醇,2-氨基-2-甲基-1-丙醇,2-氨基-3-苯基-1-丙醇,4-氨基-1-丁醇,2-氨基-1-丁醇,2-氨基-3-甲基-1-丁醇,2-氨基-4-甲硫基-1-丁醇,2-氨基-1-戊醇,(1-氨基环戊烷)甲醇,6-氨基-1-己醇,7-氨基-1-庚醇,和2-(2-氨基乙氧基)乙醇;但并不限制于这些。
关于上面所述每个分子具有一个酸酐基团的化合物([2]),例子包括:马来酸酐,丁二酸酐,邻苯二酸酐,六氢邻苯二酸酐和四氢邻苯二酸酐及甲基-六氢邻苯二酸酐。
上面所述的半酯化合物(d-2)可通过使上面所述含羟基马来酰亚胺化合物([1])中1化学当量的羟基,与具有一个酸酐基团/分子的化合物([2])中约1化学当量的酸酐基团相互反应得到。反应温度优选设定在60-100℃的范围,反应时间优选设定在1-10小时的范围。反应中,根据要求,可使用有机溶剂。
优选的含不饱和基团的一元酸(d),包括丙烯酸和马来酰亚胺己酸。
另外,关于用作任选组分的多元酸酐(e),例子包括邻苯二酸酐衍生物等,比如马来酸酐,丁二酸酐,衣康酸酐,十二烷基丁二酸酐,四氢邻苯二酸酐,六氢邻苯二酸酐,3-甲基四氢邻苯二酸酐,4-甲基四氢邻苯二酸酐和邻苯二酸酐。
关于低聚物(A),第一个具体例子是低聚物(A-[1]),它是通过使(a)组分,(b)组分,(c)组分和(d)组分相互反应得到的。第二个具体例子是低聚物(A-[2]),它是由(a)组分、(b)组分、(c)组分与(d)组分相互反应后再与(e)组分反应而得到的。
关于各组分的比,(a)组分中的一当量环氧基团,优选与0.3-1.1当量的羧酸基团反应,更优选0.9-1.05当量,以组分(b)+(c)+(d)的总量计。假定在(b)+(c)+(d)组分中羧基的总量是1当量,各组分使用的量优选这样设定,以使(b)组分具有0.05-0.5当量,优选0.1-0.3当量,(c)组分具有0.005-0.3当量,优选0.01-0.2当量,(d)组分具有0.2-0.945当量,优选0.5-0.89当量。
关于(e)组分,优选使它的0-1当量与(a),(b),(c)和(d)组分的反应产物中的一当量的羟基反应。
关于低聚物形成反应,优选使用下列材料:非溶剂或溶剂,例如,酮,如丙酮,乙基甲基酮和环己酮;芳族烃,如苯,甲苯,二甲苯和四甲基苯;乙二醇醚,如乙二醇二甲基醚,乙二醇二乙基醚,二丙二醇二甲基醚,二丙二醇二乙基醚和三乙二醇二甲基醚;酯,比如乙酸乙酯,乙酸丁酯,甲基溶纤剂乙酸酯,乙基溶纤剂乙酸酯,丁基溶纤剂乙酸酯,乙酸卡必醇酯,乙酸丙二醇单乙基醚酯,戊二酸二烷酯,丁二酸二烷酯和己二酸二烷酯;环酯,如γ-丁内酯;石油溶剂,比如石油醚,石脑油和溶剂石脑油。
在形成低聚物的反应中,为了加速反应,优选使用催化剂,所用的催化剂量设定在相对于反应产物0.1-10%。催化剂的特殊例子包括:三乙基胺,苄基二甲基胺,三乙基氯化铵,苄基三甲基溴化铵,苄基三甲基碘化铵,三苯膦,三苯,辛酸铬和辛酸锆。
而且,在反应中,为了防止聚合,可使用阻聚剂。阻聚剂的特殊例子包括对-甲氧剂苯酚,氢醌,甲基氢醌和苯基噻嗪。使用阻聚剂的量相对反应产物设定于0.05-3%。
反应温度优选设定于70-120℃,反应时间优选设定于5-40小时。
本发明树脂组合物可包含稀释剂(B)。稀释剂(B)的特殊例子包括上面提到的溶剂,有机溶剂(B-1),例如,醇,如丁醇,辛醇,乙二醇,甘油,二甘醇单甲基(或单乙基)醚三甘醇单甲基(或单乙基)醚和四甘醇单甲基(或单乙基)醚,反应性稀释剂(B-2),如(甲基)丙烯酸卡必酯,(甲基)丙烯酸苯氧基乙酯,丙烯酰吗啉,三羟甲基丙烷三(甲基)丙烯酸酯,季戊四醇三(甲基)丙烯酸酯,季戊四醇四(甲基)丙烯酸酯和二季戊四醇五(甲基)丙烯酸酯和季戊四醇六(甲基)丙烯酸酯。
包含在本发明树脂组合物中(A)和(B)组分的量,优选各占组合物中(A)和(B)总量的10-90%,更优选20-80%,关于使用(A)和(B)的比率,(A)的比率优选设定在10-90%,(B)的比率优选设定在10-90%,(B)/(A)的质量比优选设定在5-15%。
本发明的树脂组合物可包含光聚合阻聚剂(C)。关于光聚合阻聚剂(C),例子包括苯偶姻类,比如苯偶姻(二苯乙醇酮),苯偶姻甲基醚,苯偶姻乙基醚,苯偶姻丙基醚和苯偶姻异丁基醚;苯乙酮类,如苯乙酮,2,2-二甲氧基-2-苯基苯乙酮,2,2-二乙氧基-2-苯基苯乙酮,1,1-二氯苯乙酮,2-羟基-2-甲基-1-苯基丙烷-1-酮,二乙氧基苯乙酮,1-羟基环己基苯基酮和2-甲基-1-[4-(甲硫基)苯基]-2-吗啉代-丙烷-1酮;蒽醌类,比如2-乙基蒽醌,2-叔丁基蒽醌,2-氯蒽醌和2-戊基蒽醌;噻吨酮类,如2,4-二乙基噻吨酮,2-异丙基噻吨酮和2-氯噻吨酮;酮缩醇类,如苯乙酮二甲基酮缩醇和苄基甲基酮缩醇;二苯酮类,如二苯酮和4,4-双甲基氨基二苯酮;以及2,4,6-三甲基苄基二苯基膦氧化物。
它们可以单独使用,或它们的两种或多种作为混合物使用,它们可与促进剂结合使用,如叔胺,比如三乙醇胺和甲基二乙醇胺,苯甲酸衍生物,如N,N-二甲基氨基苯甲酸乙酯和N,N-二甲基氨基苯甲酸异戊酯。
光聚合引发剂(C)的含量设定在0.5-20份,优选2-15份,更优选2-5份,相对于(A)和(B)组分的100份总重量。
除了上面提到的组分外,本发明优选含有热固化组分(D)作为固化用的组分,通过含这组分,可形成印刷电路板用的材料,它具有极佳的耐焊接热和电性质。关于本发明使用的热固化组分(D),虽然不特别限制,只要在它的分子中具有与低聚物(A)一起经受热固化过程的官能团,例子包括:环氧树脂,蜜胺化合物,脲化合物,噁唑啉化合物和酚化合物。关于环氧树脂,特殊的例子包括缩水甘油醚,如双酚A型环氧树脂,双酚F型环氧树脂,苯酚-酚醛清漆型环氧树脂,甲酚-酚醛清漆型环氧树脂,三苯酚甲烷-型环氧树脂,溴化的环氧树脂,联二甲苯酚型环氧树脂和联苯酚型环氧树脂;脂环的环氧树脂,如3,4-环氧-6-甲基环己基甲基-3,4-环氧-6-甲基环己烷羧酸酯,3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯,1-环氧乙基-3,4-环氧环己烷;缩水甘油酯,如邻苯二甲酸二缩水甘油酯,四氢邻苯二甲酸二缩水甘油酯和缩水甘油基二聚物酸酯;以及杂环环氧化合物。关于蜜胺化合物,例子包括蜜胺以及蜜胺与甲醛水缩聚产物的蜜胺树脂。关于脲化合物,例子包括脲以及脲与甲醛水缩聚产物的脲树脂。关于噁唑啉化合物,例子包括2-噁唑啉,2-甲基-2-噁唑啉,2-苯基-2-噁唑啉,2,5-二甲基-2-噁唑啉,5-甲基-2-苯基-2-噁唑啉和2,4-二苯基噁唑啉。
关于酚化合物,例子包括苯酚,甲酚,二甲酚,邻苯二酚,间苯二酚,氢醌,焦棓酚和酚醛树脂A。
在这些热固化组分(D)中,优选使用环氧树脂,因为与组分(A)中的羧基的反应性特别好,并且还具有对铜的良好粘合。而且,最好使用熔点50℃以上的环氧树脂,因为这使形成光聚合涂层薄膜成为可能,在干燥过程后,它没有粘着性。
关于上述热固化组分(D)使用量的范围,设定于:热固化组分(D)的官能团,在上述(A)组分中形成0.2-3.0当量/羧基。尤其,比率设定于组分形成1.0-1.5的比率,由此在形成印刷电路板时,提供优良的耐焊接热和电性质。
而且,在环氧树脂用作上述热固化组分(D)的情况下,优选使用环氧树脂的固化加速剂,从而加速与上述组分(A)中的羧酸基团的反应。关于环氧树脂固化加速剂,例子包括:咪唑化合物,如2-甲基咪唑,1-氰基乙基-2-乙基咪唑和1-氰基乙基-2-十一烷基咪唑;***衍生物,如蜜胺,胍胺,乙酰胍胺,苯并胍胺,2,4-二氨基***和2,4-二氨基-6-甲苯基***;叔胺,如三乙醇胺,吡啶,间-二甲基氨基苯酚;以及聚酚。另外,可使用在受紫外线辐射时会变成固化加速剂的物质,优选的例子包括1,4-二氢吡啶衍生物,比如1-乙基-3,5-二甲氧基羰基-4-(2-硝基苯基)-1,4-二氢吡啶,1,2,6-三甲基-3,5-二甲氧基羰基-4-(2-硝基苯基)-1,4-二氢吡啶,2,6-二甲基-3,5-二乙酰基-4-(2-硝基苯基)-1,4-二氢吡啶和1-羧基乙基-3,5-二甲氧基羰基-4-(2-硝基苯基)-1,4-二氢吡啶。这些固化加速剂可单独使用或结合使用。
另外,在本发明中,除了上述的低聚物(A),稀释剂(B),光聚合引发剂(C)和热固化组分(D)外,如果需要,可加入各种添加剂,以便改良组合物的各种性质;例子包括:填料,如滑石,硫酸钡,碳酸钙,碳酸镁,钛酸钡,氢氧化铝,氧化铝,硅石和粘土;触变性质施加试剂,如硅胶;着色剂,如酞花青蓝,酞花青绿和二氧化钛;均化剂和防沫剂,如硅酮和氟基材料;阻聚剂,如氢醌和氢醌单乙基醚。
这里,上述组分(D)可预先混合在树脂组合物中;但是,组分更优选在涂敷到印刷线路板上前混合。在这种情况下,主试剂溶液通过将部分或全部组分(B)和环氧固化加速剂掺合到作为主组分的组分(A)中制备,固化试剂溶液通过将部分或全部组分(B)掺合到作为主组分的组分(D)制备,这两个溶液优选在使用树脂组合物时混合。
本发明的树脂组合物可以下列方式使用:例如,聚合物薄膜(例如,聚对苯二甲酸乙二醇酯,聚丙烯,聚乙烯等)用作支承物,树脂组合物作为叠层施涂到它的上面,通过使用作稀释剂(B)的有机溶剂(B-1)蒸发,可形成光敏的薄膜。
本发明的树脂组合物(液体状态或薄膜状态),供作电子部件的夹层绝缘材料是有用的,以及供作在印刷电路板中作为耐焊接物的油墨是有用的,除这些应用,它还用作密封剂,涂层材料,涂层剂,粘合剂等。
本发明的固化物是通过能量射线照射,如紫外线照射本发明上述树脂组合物固化而成。通过能量射线如紫外线,辐射的固化过程可通过使用常规的方法进行。例如,在应用紫外线时,可使用紫外线发生器,如低压汞灯,高压汞灯,超高压汞灯,氙灯和紫外线发射激光器(激元激光器等)。利用本发明树脂组合物的固化物,作为夹层绝缘材料,应用在电/电子部件(如印刷底物)的永久保护层和组成技术中。固化物层的薄膜厚度优选设定在0.5-160微米,更优选1-60微米。
以下列方式可得到本发明的印刷电路板:换句话说,在使用液态树脂组合物的情况下,通过使用网板印刷方法,喷涂方法,辊筒涂层方法,静电涂层方法,幕涂方法,将本发明的组合物以5-160微米的厚度施涂到印刷电路用的底物上,涂层的薄膜在60-110℃的正常温度范围干燥,优选60-100℃,这样可形成无粘合的涂层薄膜。此后,将具有形成暴露图形于其上的光掩膜,如负性感光膜,直接与涂层薄膜接触(或放置在涂层薄膜上而不与接触),用紫外线照射,其强度在10-2000mJ/平方厘米的正常范围,未暴露的部分,按下列描述的方法,如喷洗,振摇浸渍,刷和擦,用显影剂显影。此后,如果需要,进一步用紫外线照射,然后在正常温度范围100-200℃热处理,优选140-180℃;于是,可提供有永久保护薄膜的印刷电路板,它具有优良柔软性,满足各种性质要求,如耐热性,耐溶剂性,耐酸性,粘着力和电性能。
关于显影过程使用的有机溶剂的例子包括:卤化物,如三氯乙烷;芳族烃,如甲苯和二甲苯;酯,如乙酸乙酯和乙酸丁酯;醚,如1,4-二噁烷和四氢呋喃;酮,如甲乙酮和甲基异丁基酮;内酯,如γ-丁内酯;乙二醇衍生物,如丁基溶纤剂乙酸酯,乙酸卡必酯,二甘醇二甲基醚和丙二醇一乙基醚乙酸酯;脂环族烃,如环己酮和环己醇;溶剂,如石油溶剂,像石油醚和石脑油;水,关于碱性水溶液,可使用氢氧化钾,氢氧化钠,碳酸钠,碳酸钾,磷酸钠,硅酸钠,氨和胺等的碱性水溶液。而且,关于用于光固化的辐射光源,可适当使用低压汞灯,中压汞灯,高压汞灯,超高压汞灯,氙灯或金属卤化物灯等,作为暴光使用的活性光。
实施例
以下通过工作实施例来解释本发明。然而,本发明不限于这些实施例。
(低聚物(A)的合成实施例)
合成实施例1
将上述双酚F型环氧树脂(380克),其中,在分子式(1)中,X是-CH2-,M是氢原子,平均聚合度m是6.2(环氧当量:950克/当量,软化点:85℃),表氯醇(925克),溶解在462.5克二甲亚砜中,在70℃,搅拌下于100分钟内将60.9克(1.5摩尔)98.5%氢氧化钠加入其中。加入后,在70℃反应3小时。反应完成后,加入250克水,用水洗涤。经油-水分离过程后,减压下从油相蒸馏和收集大部分二甲亚砜和过量未反应的表氯醇,然后蒸出二甲亚砜,含副产物盐的反应产物溶解在750克甲基异丁基酮中,再加入10克30%氢氧化钠,在70℃反应1小时。反应完成后,用200克水洗涤两次,经油-水分离过程后,从油相蒸馏和收集甲基异丁基酮,这样,得到具有环氧当量310克/当量的环氧树脂,软化点69℃。在根据环氧当量计算时,发现:在形成的环氧树脂(a-1)中,上述起始物质(双酚F型环氧树脂)中6.2个醇基羟基中的5个被环氧化。装入形成的环氧树脂(a-1)(310克),二羟甲基丙酸(20.1克),分子量3500,27%的结合丙烯腈和羧基比1.91/分子的HYCAR CTBN1300×13(52.5克)[B.F.Goodrich Chemical Co.,Ltd制造],丙烯酸(43.4克),马来酰亚胺己酸(44.2克)(环氧基团数∶总羧基的比=1∶0.98),三苯膦(2.0克),甲基氢醌(0.3克)和乙酸卡必酯(238.4克),在98℃,反应约35小时,得到低聚物(A-[1]-1)。反应产物的固体组分是65%,固体组分的重量平均分子量约为6500(按照GPC方法),固体组分的酸值是1.5毫克KOH/克。
合成实施例2
合成实施例1得到的低聚物(A-[1]-1)(681.1克),四氢邻苯二酸酐(53.2克),丁二酸酐(35.0克)(羟基的数目∶酸酐基团的数目=1∶0.70)和乙酸卡必酯(52.2克),在90℃相互反应约10小时,得到反应产物(低聚物(A-[2]-1)具有固体组分65%,它的固体组分的酸值为72毫克KOH/克,固体组分的重量平均分子量约为9000(按照GPC方法)。
合成实施例3(用作比较的低聚物的合成实施例)
装入合成实施例1得到的环氧树脂(a-1)(310克),丙烯酸(71.3克),三苯膦(1.75克),甲基氢醌(0.3克)和乙酸卡必酯(206.4克),在98℃相互反应约35小时,加入四氢邻苯二酸酐(43.1克),丁二酸酐(28.4克)和乙酸卡必酯(38.5克),在90℃相互反应约10小时,得到反应产物具有固体组分65%,它的固体组分的酸值为72毫克KOH/克,固体组分的重量平均分子量约为7000(按照GPC方法)。
实施例1-3,比较实施例1-3
根据表1将掺合组分混合并溶解和捏合,进行本发明的耐焊组合物的制备。接着,通过使用网板印刷工序,将制得的各耐焊组合物施涂到印刷电路底物上(通过层叠亚胺膜与铜箔形成),在80℃干燥20分钟。此后,将负性薄膜放置在这底物上,用暴光机器根据预定图形以紫外线用累积暴光剂量600mJ/厘米2照射,然后用γ-丁内酯(实施例1)和1.0重量%碳酸钠水溶液(实施例2,3以及比较实施例1-3)显影,在150℃经热固化加工60分钟,制备样品底物。相对于光敏性能,评估各形成的耐焊组合物。换句话说,相对于形成的样品底物,对于特性,如显影性,耐焊接热,柔软性,抗热变形和耐无电镀金,进行评估。结果显示在表2上。这里,评估方法和评估标准显示如下:
表1
实施例 | |||
1 | 2 | 3 | |
(A)组分 | |||
合成实施例1中得到的低聚物(A-[1]) | 154 | ||
合成实施例1中得到的低聚物(A-[1]) | 154 | 154 | |
(B)组分 | |||
KAYARAD DPHA*1 | 16 | 16 | 16 |
乙酸卡必酯 | 10 | ||
(C)组分 | |||
Irgacure-907*2 | 3 | 4 | 4 |
Kayacure-DETX-S*3 | 0.36 | 0.48 | 0.48 |
(D)组分 | |||
YX-4000*1 | 30 | ||
DEN-438*5 | 30 | 30 |
其他 | |||
细粉末硅土(填料) | 10 | 10 | 10 |
1-乙基-3,5-二甲氧基羰基-4(2-硝基苯基)-1,4-二氢吡啶(环氧树脂固化加速剂) | 3 | 3 | |
蜜胺(环氧树脂固化加速剂) | 1.2 | ||
KS-66(防沫剂)*6 | 1 | 1 | 1 |
(A)组分 | |||
合成实施例3中得到的低聚物 | 154 | 154 | 154 |
(B)组分 | |||
KAYARAD DPHA*1 | 16 | 16 | 16 |
乙酸卡必酯 | 10 | ||
(C)组分 | |||
Irgacure-907*2 | 10 | 10 | 3 |
Kayacure-DETX-S*3 | 1.2 | 1.2 | 0.36 |
(D)组分 | |||
YX-4000*4 | 30 | 30 | |
DEN-438*5 | 30 | ||
其他 | |||
细粉末硅土(填料) | 10 | 10 | 10 |
1-乙基-3,5-二甲氧基羰基-4(2-硝基苯基)-1,4-二氢吡啶(环氧树脂固化加速剂) | 3 | 3 | |
蜜胺(环氧树脂固化加速剂) | 1.2 | ||
KS-66(防沫剂)*6 | 1 | 1 | 1 |
注:
*1;KAYARAD DPHA:Nippon Kayaku Co.,Ltd.制造,二季戊四醇五丙烯酸酯和二季戊四醇六丙烯酸酯的混合物。
*2;Irgacure 907:Ciba specialty Chemicals Inc.制造,聚合引发剂,2-甲基-1-[4-(甲硫基)苯基]-2-吗啉代丙烷-1-酮
*3;Kayacure-DETX-S:Nippon Kayaku Co.,Ltd.制造,光聚合引发剂,2,4-二乙硫基噻吨酮
*4;YX-4000:Yuka Shell Epoxy Co.,Ltd.制造,双酚型环氧树脂。
*5;DEX-438:Dow Chemical Company制造,酚醛清漆型环氧树脂。
*6;KS-66:Shin-Etsu Chemical Co.,Ltd.制造,硅酮基防沫剂。
评估方法和评估标准
(1)光敏性
有21级的级片(Stopher Co.,Ltd.制造),与干燥工序后的涂层薄膜接触,用累积光量600mJ/平方厘米紫外线照射。接着,在喷洗压力2.0公斤/平方厘米下,通过使用γ-丁内酯(实施例1)和1%碳酸钠水溶液(实施例2,3以及比较实施例1-3)60秒,对它进行显影;于是,确认涂层的未被显影的级数。评估根据下列标准。
○6级以上
△4-5级
×不大于3级
(2)显影性
涂层薄膜在80℃干燥90分钟,通过在30℃使用γ-丁内酯和1%碳酸钠水溶液(实施例2,3以及比较实施例1-3)经历喷涂显影工序;于是,评估其显影性。
○目视观察有无残留物
△目视观察有轻微残留物
×目视观察许多残留物
(3)耐焊接热
样品底物用树脂基焊剂涂层,浸在260℃熔化的焊料中10秒钟;然后,根据在用玻璃纸胶带分离时固化膜的状态,评估形成的底物。
○未发现反常
×发生分离
(4)柔软性
根据完全弯曲180度时的状态,评估试验底物。
○无裂纹
△出现轻微裂纹
×折叠部分中出现的裂纹,导致固化膜分离
(5)耐热退化
在125℃下保持5天后,根据在180度完全弯曲时的状态,评估试验底物
○无裂纹
△发生轻微裂纹
×折叠部分中出现的裂纹,导致固化膜分离
(6)耐无电镀金
在试验底物按照下面所述镀金后,根据用玻璃胶带(注册商标)分离时固化膜的状态,评估形成的底物。
○未发现反常
△出现轻微分离
×未发生分离
无电镀金的方法
样品底物浸入酸性脱脂溶液(20体积%MetexL-5B的水溶液(NipponMacDiarmid Co.,Ltd.制造)中3分钟,进行脱脂,然后浸入流动的水中3分钟,进行洗涤。接着,样品底物浸在14.3重量%室温的过硫酸铵水溶液中3分钟,进行软蚀刻,然后浸在流动的水中3分钟,进行洗涤。接着,样品底物浸在催化剂溶液(Meltex Co.,Ltd.制造,金属电镀活化剂350的10体积%水溶液)中7分钟,使催化剂施加到它的上面,然后浸在流动的水中3分钟,进行洗涤。施加了催化剂的样品底物然后浸在85℃的镀镍溶液的20体积%水溶液(PH4.6)中20分钟,这样在它的上面进行无电镀镍过程。在浸入室温的10体积%硫酸盐水溶液1分钟后,样品底物浸在流动的水中30秒-1分钟,进行洗涤。接着,样品底物浸在95℃镀金溶液(Meltex Co.,Ltd.制造,15体积%AurolectrolessUP和3体积%***金的溶液,PH 6)中20分钟,在其上面进行无电镀金,然后浸在流动的水中3分钟进行洗涤,再浸入60℃热水中3分钟,进行热水洗涤。在进行充分洗涤后,将水完全抖掉,并进行干燥,得到无电镀金样品底物。
表2
项目 | 实施例 | 比较实施例 | ||||
1 | 2 | 3 | 1 | 2 | 3 | |
光敏性 | ○ | ○ | ○ | ○ | ○ | × |
显影性 | ○ | ○ | △ | △ | × | △ |
耐焊接热 | ○ | ○ | ○ | ○ | ○ | ○ |
柔软性 | ○ | ○ | ○ | × | × | × |
耐热退化 | ○ | ○ | ○ | × | × | × |
耐无电镀金 | ○ | ○ | ○ | ○ | ○ | × |
如表2的内容清楚显示的,即使聚合引发剂的使用量很小,本发明的组合物具有充分的光敏性,极佳的显影性,提供的固化膜具有极佳的耐焊接热,柔软性,耐热退化和耐无电镀金。
工业的可应用性
本发明使提供树脂组合物成为可能,该树脂组合物即使在使用很少聚合引发剂时,具有充分的固化性,并且具有极佳的显影性,提供的固化膜具有极佳的柔软性,耐焊接热,耐热退化和耐无电镀金,使得用弱碱溶液进行显影的过程成为可能,适合于耐焊接和夹层绝缘层材料的应用中。本树脂组合物特别适合用在印刷电路板尤其是柔软的印刷电路板的耐焊接层和夹层绝缘层中。
Claims (14)
1.一种树脂组合物包括:
使下列组分(a)-(d)共同反应得到的低聚物(A):
(a)由下列分子式(1)表示的环氧树脂:
在分子式(1)中,X是-CH2-或-C(CH3)2-,m是1或以上的整数,M是氢原子或下列分子式(G)表示的基团:
这里,在m是1情况下,M由分子式(G)表示,在m大于1的情况下,至少一个M由分子式(G)表示,而其他的是氢原子;
(b)具有2-6个碳原子的羧酸的二羟甲基化的化合物;
(c)羧酸化的橡胶状聚合物;
(d)选自(甲基)丙烯酸和含马来酰亚胺基的一元酸的一种或两种以上具有不饱和基团的一元酸,
关于各组分的反应比,(a)组分中的一当量环氧基团与组分(b)+(c)+(d)中0.3-1.1当量的羧基总量相当;对于(b)+(c)+(d)组分中羧基的总量是1当量来说,(b)组分具有0.05-0.5当量,(c)组分具有0.005-0.3当量,(d)组分具有0.2-0.945当量。
2.一种树脂组合物包括:
使下列化合物(a)-(e)共同反应得到的低聚物(A):
(a)由下列分子式(1)表示的环氧树脂:
在分子式(1)中,X是-CH2-或-C(CH3)2-,m是1或以上的整数,M是氢原子或下列分子式(G)表示的基团:
这里,在m是1情况下,M由分子式(G)表示,在m大于1的情况下,至少一个M由分子式(G)表示,而其他的是氢原子;;
(b)具有2-6个碳原子的羧酸的二羟甲基化的化合物;
(c)羧酸化的橡胶状聚合物;
(d)选自(甲基)丙烯酸和含马来酰亚胺基的一元酸的一种或两种以上具有不饱和基团的一元酸,
(e)多元酸酐,
关于各组分的反应比,(a)组分中的一当量环氧基团与组分(b)+(c)+(d)中0.3-1.1当量的羧基总量相当;对于(b)+(c)+(d)组分中羧基的总量是1当量来说,(b)组分具有0.05-0.5当量,(c)组分具有0.005-0.3当量,(d)组分具有0.2-0.945当量;并且对于组分(a)到(d)的反应产物中羟基数量为1当量来说,组分(e)为1当量或更少。
3.如权利要求1或2所述的树脂组合物,其特征在于:低聚物(A)具有的重量平均分子量在1000-100000的范围内。
4.如权利要求1或2所述的树脂组合物,其特征在于:低聚物(A)具有的酸值在1-300毫克KOH/克。
5.如权利要求1或2所述的树脂组合物,其特征在于:在分子式(1)中,M由分子式(G)表示的比率在70-90摩尔%的范围内。
6.如权利要求2所述的树脂组合物,其特征在于:多元酸酐(e)是邻苯二甲酸酐衍生物。
7.如权利要求1或2所述的树脂组合物,还包括热固化组分(D),所述组分(D)的用量为这样的比例,即所述组分(D)的官能团形成0.2-3.0当量/所述(A)组分中的羧基。
8.如权利要求7所述的树脂组合物,其特征在于:热固化组分(D)是环氧树脂。
9.如权利要求8所述的树脂组合物,还包括1,4-二氢吡啶衍生物作为环氧树脂的固化加速剂。
10.如权利要求1或2所述的树脂组合物,还包括稀释剂(B),所述组分(A)和(B)的数量占组合物中(A)+(B)总量的10%-90%,并且对于所用(A)和(B)的之比来说,(A)的比例为10-90%,(B)的比例为10-90%。
11.如权利要求10所述的树脂组合物,它还包括光聚合引发剂(C),所述引发剂(C)的含量为0.5-20份,以组分(A)和组分(B)总量为100质量份计。
12.一种组合物,它包含权利要求10的树脂组合物,应用于用在印刷电路板中的耐焊接层或夹层绝缘层。
13.一种固化物,它包含权利要求1或2所述的组合物。
14.如权利要求13所述的固化物,它用于印刷电路板。
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CN100358953C (zh) * | 2005-05-23 | 2008-01-02 | 容大油墨(惠州)有限公司 | 一种液态感光防焊油墨及其电路板 |
DE102005053553A1 (de) * | 2005-11-08 | 2007-05-16 | Heraeus Gmbh W C | Lotpasten mit harzfreien Flussmittel |
JP4979963B2 (ja) * | 2006-03-10 | 2012-07-18 | 株式会社Adeka | 光学材料用硬化性組成物及び光導波路 |
JP2008243957A (ja) * | 2007-03-26 | 2008-10-09 | Nitto Denko Corp | 配線回路基板の製法 |
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US9869392B2 (en) | 2011-10-20 | 2018-01-16 | Lam Research Corporation | Edge seal for lower electrode assembly |
US9635962B2 (en) | 2012-04-12 | 2017-05-02 | Cabeau, Inc. | Travel pillow with lateral and rear support bar and a flat and thin back |
EP3074213B1 (en) * | 2013-11-26 | 2018-09-26 | Novartis AG | A metal oxide dispersion and uses thereof |
US10090211B2 (en) | 2013-12-26 | 2018-10-02 | Lam Research Corporation | Edge seal for lower electrode assembly |
JP6275620B2 (ja) * | 2014-10-17 | 2018-02-07 | 日本化薬株式会社 | 感光性樹脂組成物及びその硬化物 |
US20160145452A1 (en) * | 2014-11-24 | 2016-05-26 | 3D Systems, Incorporated | Inks comprising liquid rubber for 3d printing |
CN110527350B (zh) * | 2019-08-26 | 2022-04-15 | 鹤山市炎墨科技有限公司 | 一种高耐热高交联度光固化阻焊油墨及其制备方法 |
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JP2877659B2 (ja) * | 1993-05-10 | 1999-03-31 | 日本化薬株式会社 | レジストインキ組成物及びその硬化物 |
JPH0841146A (ja) * | 1994-07-27 | 1996-02-13 | Nippon Kayaku Co Ltd | 樹脂組成物、レジストインキ組成物及びその硬化物 |
JPH08134331A (ja) * | 1994-11-08 | 1996-05-28 | Dainippon Ink & Chem Inc | 光硬化性樹脂組成物および可撓性ソルダーレジストインキ |
JPH0912654A (ja) * | 1995-06-26 | 1997-01-14 | Nippon Kayaku Co Ltd | エネルギー線硬化性樹脂組成物及びその硬化物 |
JPH10316729A (ja) * | 1997-05-20 | 1998-12-02 | Nippon Kayaku Co Ltd | 樹脂組成物、ソルダーレジスト樹脂組成物及びこれらの硬化物 |
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JP3759672B2 (ja) * | 1997-12-05 | 2006-03-29 | 日本化薬株式会社 | 樹脂組成物及びその硬化物 |
JPH11181040A (ja) * | 1997-12-22 | 1999-07-06 | Nippon Kayaku Co Ltd | 樹脂組成物、その硬化物及びプリント配線板 |
JPH11189631A (ja) * | 1997-12-26 | 1999-07-13 | Nippon Kayaku Co Ltd | 樹脂組成物、その硬化物及びプリント配線板 |
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CN102411261A (zh) * | 2010-09-17 | 2012-04-11 | 日东电工株式会社 | 感光性树脂组合物及使用其的带金属支撑体的电路基板 |
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CN1538978A (zh) | 2004-10-20 |
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US20050004288A1 (en) | 2005-01-06 |
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