CN1072938A - 挥发性烯属不饱和单体低排放的乙烯基酯和聚酯树脂组合物 - Google Patents
挥发性烯属不饱和单体低排放的乙烯基酯和聚酯树脂组合物 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
通过添加一种干性油诸如玉米油和一种环氧化
干性油诸如环氧化大豆油来改进乙烯基酯或聚酯树
脂。这些树脂含有聚合性的,挥发性烯属不饱和单体
和一种排放抑制量的地蜡。这一改进是在二次胶粘
性方面。
Description
本发明涉及苯乙烯低排放的乙烯基酯和聚酯配方,该配方含有作为苯乙烯排放抑制剂的地蜡和作为二次胶粘性促进剂的干性油和环氧化干性油。
大多数乙烯基酯树脂和不饱和聚酯树脂含有聚合性的,挥发性烯属不饱和单体,诸如苯乙烯作为活性稀释剂。由于苯乙烯或其它聚合性的挥发性烯属不饱和单体是一种挥发性组分,该组分在热固性乙烯基酯和不饱和聚酯树脂贮存和/或固化期间往往易于释放到环境中,因而越来越需要降低在贮存和/或固化期间释放到环境中的苯乙烯或其它聚合性的,挥发性单体量。减少苯乙烯或其它聚合性的,挥发性单体释放到环境中的一种方法是把地蜡加到配方中。这样做时确实降低了释放到环境中的苯乙烯的量,可是该组合物二次胶粘性受到了损害。因此,把一种能够消除或减少二次胶粘性损失的组分添加到配方中将会是十分合乎需要和有利的。
现已发现,可借助向配方中添加玉米油和环氧化豆油来防止含有聚合性的,挥发性烯属不饱和单体诸如苯乙烯的乙烯基酯和不饱和聚酯配方损失二次胶粘性,该配方含有地蜡作为聚合性的,挥发性烯属不饱和单体的排放抑制剂。
本发明涉及对含有聚合性的,挥发性烯属不饱和单体和聚合性的烯属不饱和单体排放抑制量的地蜡的乙烯基酯和不饱和聚酯树脂的改进;该改进包括在该组合物中使用一种二次胶粘性促进量的至少一种干性油和至少一种环氧化干性油。
本发明的另一形态涉及一种聚合性的,挥发性烯属不饱和乙烯单体抑制剂/二次胶粘促进添加剂组合物,该组合物包含(1)至少一种挥发性烯属不饱和单体,(2)地蜡,(3)至少一种干性油,(4)至少一种环氧化干性油。
本发明的另一形态涉及一种固化性组合物,该组合物包含(A)至少一种乙烯基酯树脂或至少一种不饱和聚酯树脂,或者它们的混合物;(B)至少一种聚合性的,挥发性烯属不饱和单体;(C)一种聚合性烯属不饱和单体排放抑制量的地蜡;(D)二次胶粘性促进量的至少一种干性油;(E)二次胶粘性促进量的至少一种环氧化干性油;(F)固化量的一种合适的固化剂。
本发明的再一形态涉及一种用上述固化性组合物浸透或浸渍的基材。
本发明的再一形态涉及上述浸透或浸渍基材制造的产品或制品,该产品或制品是由一层或多层该浸透或浸渍的基材加工成预定的形状然后固化得到。
本发明可相应地由上述各组分,或主要由上述各组分组成。
于此处例证性地公开的本发明,在缺少任何一种此处没有具体公开或列举的组分的情况下也可以正常地实施。
本发明的挥发性烯属不饱和乙烯单体抑制剂/二次胶粘性促进添加剂组合物通常包含(1)20%-40%,较好是20%-35%,更好是25%-35%(重量)的至少一种挥发性烯属不饱和单体,(2)10%-25%,较好是10%-20%,更好是13%-17%(重量)的地蜡,(3)10%-30%,较好是18%-28%,更好是20%-26%(重量)的至少一种干性油,(4)20%-40%,较好是20%-35%,更好是25%-35%(重量)的至少一种环氧化干性油。
在这里能用的合适的乙烯基酯树脂包括任何一种由每分子平均含多于一个邻近环氧基的环氧树脂与不饱和羧酸反应制备的树脂。通常反应物的用量是,酸基对环氧基之比是0.95∶1-1.05∶1,最好是1∶1。
合适的环氧树脂包括,含有每分子平均多于一个缩水甘油基的环氧树脂,诸如脂族,环脂族或芳族化合物的缩水甘油基衍生物,上述三族化合物每分子平均含多于一个羟基,羧基或氨基,或者任何一种它们的混合物。特别适用的上述环氧树脂包括,例如下列各物的缩水甘油醚:间苯二酚,邻苯二酚,氢醌,双酚A,双酚F,双酚K,芴,苯酚醛树脂或甲酚醛树脂,它们的卤代衍生物,特别是溴代衍生物,或者任何一种它们的混合物。
能用于制备该乙烯基酯树脂的合适的不饱和羧酸包括,例如丙烯酸,甲基丙烯酸,冰甲基丙烯酸,或者任何一种它们的混合物。
环氧树脂与该不饱和酸之间反应的操作温度通常是90℃-130℃,较好是100℃-120℃,更好是105℃-115℃。反应时间要足以完成该反应。当酸值达到1时通常认为反应完全。反应时间通常是3-6小时。
如果需要,可以使用一种促进环氧树脂和不饱和酸之间反应的催化剂。适用的上述催化剂包括三(二甲氨基甲基)苯酚,溴化四乙铵,或者任何一种它们的混合物。特别适用的上述催化剂包括,例如三(二甲氨基甲基)苯酚,或者任何一种它们的混合物。催化剂的用量通常是0.05-0.08,较好是0.055-0.075,更好是0.065重量份催化剂(每100重量份羧酸与环氧树脂所得的混合物)。
适用于此的不饱和聚酯树脂包括,例如由两种化合物反应制备的一类不饱和聚酯,前种化合物每分子平均含有多于1个,最好是2个脂族,环脂族或芳族羟基,后种化合物每分子平均含有多于1个脂族,环脂族或芳族羧基,但这两种化合物中至少须有一种含有聚合性不饱和基团。通常反应物的用量是提供一个酸基对羟基的比值。
每分子平均含有多于1个羟基,特别适用于制备不饱和聚酯树脂的化合物包括,例如含脂族,环脂族或芳族羟基的那些化合物。特别适用的上述化合物包括,例如丙二醇,乙二醇,双酚A,或者任何一种它们的混合物。
每分子平均含有多于1个羧酸基,特别适用于制备不饱和聚酯树脂的化合物包括,例如富马酸,马来酐,琥珀酐,氯菌酸酐,邻苯二甲酸或其酐,间苯二甲酸或其酐,对苯二甲酸或其酐,或者任何一种它们的混合物。
含羟基的化合物与酸之间反应的操作温度通常是150℃-190℃,较好是170℃-190℃,更好是175℃-185℃。反应时间要足以完成该反应。当酸值达到50或略低时通常认为反应完全。反应时间是6-16小时。
如果需要,可以使用一种促进含羟基的化合物和酸间反应的催化剂。适用的上述催化剂包括丁基锡酸,对甲苯磺酸,或者任何一种它们的混合物。通常催化剂的用量是每100重量份羧酸与含羟基的化合物所得的混合物为0.05-1.0份,较好是0.05-0.1份,更好是0.075重量份催化剂。
适用于此的聚合性的,挥发性烯属不饱和单体包括,例如苯乙烯,α-甲基苯乙烯,氯代苯乙烯,乙烯基苯,乙烯基甲苯,对甲基苯乙烯,二乙烯基苯,或者任何一种它们的混合物。丙烯酸和甲基丙烯酸的C1-C8烷基酯也是适用的。苯乙烯是优选的聚合性的,挥发性烯属不饱和乙烯基单体。
聚合性的,挥发性烯属不饱和单体的通常用量是20-60,较好是35-55,更好是40-50%(重量)(根据树脂和聚合性的,挥发性烯属不饱和单体的总重量计算)。
此处使用的地蜡是一种精制的复杂组成烃类的混合物,精制方法是先用浓硫酸处理再经骨炭过滤。其熔点为61℃-78℃。其它的地蜡名称是:地蜡170-D,地蜡170M.B.,白地蜡,黄地蜡,黄地蜡S特种,S&P地蜡黄等。地蜡生产商Strahl & Pitsch公司规定,地蜡是一种来源于矿物或石油的烃蜡。
地蜡的用量是会使配方中含有的苯乙烯或其它挥发性的,聚合性烯属不饱和单体在贮存和固化期间的排放受到抑制的任何量。特别适合的地蜡用量是,例如0.15%-0.4%,较好是0.15%-0.3%,更好是0.18%-0.25%(重量),以上用量根据苯乙烯(聚合性的烯属不饱和单体),可能存在的其它活性稀释剂(聚合性的烯属不饱和单体)和树脂的总重量计算。
此处使用的“干性油”术语意思是含亚油酸和/或亚麻酸甘油酯的天然存在的油类。适用的油的碘值是100-210,较好是115-150,更好是115-140。特别适用的上述干性油包括,例如,玉米油,亚麻子油,红花油,大豆油,向日葵油,棉子油,菜子油,紫苏子油,大麻子油,或者任何一种它们的混合物。优选的是玉米油和大豆油。
干性油的用量是与环氧化干性油结合在一起会使配方的二次胶粘性得到提高的任何量。特别适合的干性油用量是,例如0.1%-0.7%,较好是0.2%-0.5%,更好是0.25%-0.4%(重量),以上用量根据苯乙烯(聚合性烯属不饱和单体),可能存在的其它活性稀释剂(聚合性然属不饱和单体)和树脂的总重量计算。
术语“环氧化干性油”包括环氧化了的含亚油酸和/或亚麻酸甘油酯的天然存在的油类。适用的上述环氧化干性油包括,例如环氧化大豆油,环氧化玉米油,环氧化棉子油,环氧化红花油,环氧化向日葵油,环氧化棉子油,环氧化菜子油,环氧化紫苏子油,环氧化大麻子油,或者任何一种它们的混合物。优选的是环氧化大豆油和环氧化玉米油。
可通过表卤醇与预定的干性油反应,然后用一种合适的碱性作用化合物,诸如碱金属卤化物,碱金属的碳酸盐使生成的卤代醇中间体脱去卤化氢的方法来制备环氧化干性油。氢氧化钠是优选的。若干环氧化干性油是市场上可以买到的,诸如环氧化大豆油有Atochem North America公司供应的VIKOFLEX7170,环氧化棉子油有Atochem North America公司供应的VIKOFLEX7190。
环氧化干性油的用量是与干性油结合在一起会使配方的二次胶粘性得到提高,并同样地延缓苯乙烯的挥发作用的任何量。特别适合的环氧化干性油用量是,例如0.2-0.7,较好是0.3-0.6,更好是0.35-0.55%(重量),以上用量根据苯乙烯(聚合性烯属不饱和单体),可能存在的其它活性稀释剂(聚合性烯属不饱和单体)和树脂的总量计算。
可用任何一种适用于固化乙烯基酯树脂和不饱和聚酯树脂的方法来固化本发明的组合物。可用偶氮化合物,过氧化物,或者任何一种它们的混合物来正常地使本发明的组合物固化。特别适用的固化剂包括,例如甲乙酮过氧化物,氢过氧化枯烯,过氧化苯甲酰,或者任何一种它们的混合物。
固化催化剂的用量通常是1-2.5,较好是1-1.5,更好是1-1.25%(重量),根据树脂的重量计算。
如果需要,还可使用固化促进剂。适用的上述固化促进剂包括,例如,环烷酸钴,辛酸钴,N,N-二甲基苯胺,N,N-二甲基乙酰胺,或者任何一种它们的混合物。
固化促进剂的用量通常是0.05-0.6,较好是0.1-0.4,更好是0.1-0.3%(重量),根据树脂的重量计算。
可用本发明的固化性组合物浸透或浸渍的适用的基材包括加工成织物,毡料或复丝形状的天然或合成纤维。适用的上述材料可以是尼龙,人造丝,棉,玻璃,石墨,碳,芳族聚酰胺纤维,聚酯,或者任何一种它们的混合物。
可向本发明的组合物中添加另外的添加剂诸如颜料,染料,填料,或者任何一种它们的混合物。
本发明的固化性组合物可用于制造层压制件,涂料,聚合物混凝土。
下列组分用于各实施例和对照实验中。
乙烯基酯树脂(VER)A是一种由环氧当量为380-420的双酚A的二缩水甘油醚和甲基丙烯酸反应制成的乙烯基酯树脂,反应体系其酸对环氧基的当量比为1∶1。该树脂含苯乙烯45%(重量)。
聚酯树脂(PER)A是一种刚性,低活性低粘度,触变性的邻苯二甲酸层压树脂,市场上由Reichhold公司供应的POLYLITETM商标聚酯树脂33-087。为了室温固化,借助添加甲基乙基酮过氧化物将该树脂“预促进”。该树脂含苯乙烯43-47%(重量)。
对该乙烯基酯和/或不饱和聚酯组合物进行下列试验。
烯属不饱和单体的排放量
试验以一种完全被催化的固化性加工整体为基础,因为在固化条件下大多数挥发性的烯属不饱和单体已失去。
记下该试验进行的温度和相对湿度状况。把100±0.5g被催化的树脂倒进一个已称过皮重的1加仑(3.78l)涂料罐中,其盖板有一张开的纸夹,当树脂配方胶凝,并胶凝时间达到1小时以后,用重量减轻法来测定烯属不饱和单体的排放量。胶凝时间的测定方法是,从树脂中间歇地提升起纸夹,直到该树脂撕裂或粘附到纸夹上为止,记录烯属不饱和单体的重量减轻(g/m2),并用重量减轻的克数乘以因子60.56。来求出烯属不饱和单体的损耗量。60.56这个系数是美国California South Coast Air Quality Board(加里福尼亚南海岸空气质量管理局)提供的。
二次胶粘性
二次胶粘性促进试验是用ASTM D790-86、对固化后的层压件进行70%抗弯强度测定的周期性挠曲试验。用ASTMD3479-76(82)来制定二次胶粘性试验。
按下列顺序借助浸透6″×12″玻璃纤维层来制备一次层压件,CSM/WR/CSM/WR/CSM。各层用树脂充分浸湿,但短纤维粗纱毡最后层的表面树脂不要过多。短纤维粗纱毡最后层几乎完全由在前的毡层上添加树脂来浸湿。(如果初始叠层中的短纤维粗纱毡层的树脂过多就不会获得合格的二次胶粘性。单位表面积上地蜡的量会变得太多,使二次胶粘性促进剂也不能致胜。树脂过多的表面在结构上往往不象靠近表面含合适量玻璃纤维层的那个表面一样坚固)。然后将五重层压板在约25℃的温度下固化20-24小时。
然后按下列顺序,CSM/WR/CSM,借助在一次层压件顶部浸透6″×12″玻璃纤维层制备二次层压件。
CSM=1.5昂司短纤维粗纱毡
WR=24昂司纺织粗纱
然后在约25℃温度下使二次层压件至少固化20-24小时。然后对所得的固化好的层压件进行上述ASTM试验。
实施例1
试验若干配方的苯乙烯排放量和二次胶粘性。这些组合物和试验结果见表1。
表Ⅱ
配方 | ||||
A | B | C | D | |
树脂-苯乙烯预共混物,gms树脂,型号克数苯乙烯,克数%a膏状添加剂,克数%b地蜡,克数%c玉米油,克数%cESOd,克数%c苯乙烯,克数%e温度,0F℃树脂温度,%苯乙烯损耗克/米2 | 100VER A5545451.31.30.20.20.30.30.40.40.40.774-7623.3-24.462-7096 | 100VER A5545451.31.30.20.20.30.30.40.40.40.77523.96686 | 100VER A53-5743-4743-471.31.30.20.20.30.30.40.40.40.7-0.8772560-6340 | 100VER A53-4743-4743-471.31.30.20.20.30.3040.40.40.7-0.876-7724.4-2560-6456 |
a %(重量),根据树脂的重量计算。
b %(重量),根据树脂加苯乙烯的重量计算,不包括膏状添加剂所含的苯乙烯。
c %(重量),根据树脂加苯乙烯的重量计算,包括经由膏状添加剂加进去的苯乙烯。
d 环氧化大豆油
e %(重量),根据树脂的重量计算。
实施例2
通过使下列各组分共混来制备一种添加到乙烯基酯和不饱和聚酯树脂中的膏状浓缩物:
苯乙烯 30.8%
地蜡 15.3%
玉米油 23.1%
环氧化大豆油 30.8%
100.0%
共混操作是在一个用风动搅拌器的7加仑(26.5l)玻璃容器中于75℃下进行。当混合物透明时,蜡全部溶解,使该混合物冷却到65℃-70℃。将1加仑(3.8l)量的该混合物排入1加仑(3.8l)的罐中,封闭并摇动直到该罐处于室温为止。
这种管状浓缩物用作一种加到乙烯基酯树脂A和聚酯树脂A中的添加剂,然后做苯乙烯损耗试验。这些配方及结果见表Ⅱ。
Claims (8)
1、组合物,该组合物含至少一种乙烯基酯树脂或至少一种不饱和聚酯树脂或这类树脂的混合物,至少一种聚合性的,挥发性烯属不饱和单体和一种抑制聚合性的,挥发性烯属不饱和单体排放量的地蜡;其特征在于在该组合物中使用一种二次胶粘性促进量的干性油和一种二次胶粘性促进量的环氧化干性油。
2、权利要求1的组合物,其中该地蜡的用量为0.15-0.4%(重量),其用量根据树脂和聚合性的,挥发性烯属不饱和单体的总重量计算,该干性油的用量为0.1-0.7%(重量),其用量根据树脂和聚合性的,挥发性烯属不饱和单体的总重量计算,该环氧化干性油的用量为0.2-0.7%(重量),其用量根据树脂和聚合性的,挥发性烯属不饱和单体的总重量计算。
3、一种挥发性的烯属不饱和乙烯单体抑制剂/二次胶粘性促进添加剂组合物,该组合物包含(1)至少一种聚合性的,挥发性烯属不饱和单体(2)地蜡,(3)干性油,(4)环氧化干性油。
4、权利要求3的一种组合物,其中该聚合性的,挥发性烯属不饱和单体的用量为20%-40%(重量),其用量根据聚合性的,挥发性烯属不饱和单体,地蜡,干性油,和环氧化干性油的总重量计算;该地蜡的用量为10-25%(重量),其用量根据聚合性的,挥发性烯属不饱和单体,地蜡,干性油,和环氧化干性油的总重量计算;该干性油的用量为10-30%(重量),其用量根据聚合性的,挥发性烯属不饱和单体,地蜡,干性油,和环氧化干性油的总重量计算;该环氧化干性油的用量为20-40%(重量),其用量根据聚合性的,挥发性烯属不饱和单体,地蜡,干性油,和环氧化干性油的总重量计算。
5、一种固化性组合物,该组合物包含(A)至少一种乙烯基酯树脂或至少一种不饱和聚酯树脂或它们的混合物;(B)至少一种聚合性的,挥发性烯属不饱和单体;(C)一种抑制聚合性的,挥发性烯属不饱和单体排放量的地蜡;其特征在于另外使用(D)一种二次胶粘促进量的干性油;(E)一种二次胶粘促进量的环氧化干性油;(F)一种固化量的合适固化剂。
6、权利要求5的一种固化性组合物,其中该聚合性的,挥发性烯属不饱和单体的用量为20-60%(重量),其用量根据树脂和聚合性的,挥发性烯属不饱和单体的总重量计算;该地蜡的用量为0.15-0.40%(重量),其用量根据树脂和聚合性的,挥发性烯属不饱和单体的总重量计算;该干性油的用量为0.1-0.70%(重量),其用量根据树脂和聚合性的,挥发性烯属不饱和单体的总重量计算;该环氧化干性油的用量为0.2-0.7%(重量),其用量根据树脂和聚合性的,挥发性烯属不饱和单体的总重量计算。
7、用权利要求5或6任一项固化性组合物浸透或浸渍的一种基材。
8、将一层或多层权利要求7的浸透或浸渍过的基材按所希望的构型成型并固化制成的产品或制品。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/797,640 US5206077A (en) | 1991-11-25 | 1991-11-25 | Low vaporizable ethylenically unsaturated monomer emission vinyl ester and polyester resin compositions |
US797,640 | 1991-11-25 |
Publications (1)
Publication Number | Publication Date |
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CN1072938A true CN1072938A (zh) | 1993-06-09 |
Family
ID=25171406
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN92113296A Pending CN1072938A (zh) | 1991-11-25 | 1992-11-24 | 挥发性烯属不饱和单体低排放的乙烯基酯和聚酯树脂组合物 |
Country Status (15)
Country | Link |
---|---|
US (5) | US5206077A (zh) |
EP (1) | EP0614476B1 (zh) |
JP (1) | JP3159988B2 (zh) |
CN (1) | CN1072938A (zh) |
AT (1) | ATE137787T1 (zh) |
AU (1) | AU2877992A (zh) |
BR (1) | BR9206960A (zh) |
CA (1) | CA2122466A1 (zh) |
DE (1) | DE69210625T2 (zh) |
FI (1) | FI942399A (zh) |
MY (1) | MY130021A (zh) |
NO (1) | NO941921L (zh) |
TW (1) | TW221824B (zh) |
WO (1) | WO1993011193A1 (zh) |
ZA (1) | ZA929089B (zh) |
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CN110892019A (zh) * | 2017-06-27 | 2020-03-17 | 日立汽车系统株式会社 | 不饱和聚酯树脂组合物及使用其的电气设备 |
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-
1991
- 1991-11-25 US US07/797,640 patent/US5206077A/en not_active Expired - Fee Related
-
1992
- 1992-10-21 EP EP19920922270 patent/EP0614476B1/en not_active Expired - Lifetime
- 1992-10-21 CA CA 2122466 patent/CA2122466A1/en not_active Abandoned
- 1992-10-21 JP JP51010293A patent/JP3159988B2/ja not_active Expired - Fee Related
- 1992-10-21 BR BR9206960A patent/BR9206960A/pt not_active IP Right Cessation
- 1992-10-21 AU AU28779/92A patent/AU2877992A/en not_active Abandoned
- 1992-10-21 DE DE1992610625 patent/DE69210625T2/de not_active Expired - Fee Related
- 1992-10-21 AT AT92922270T patent/ATE137787T1/de active
- 1992-10-21 WO PCT/US1992/009076 patent/WO1993011193A1/en active IP Right Grant
- 1992-11-23 MY MYPI92002134A patent/MY130021A/en unknown
- 1992-11-24 TW TW81109406A patent/TW221824B/zh active
- 1992-11-24 CN CN92113296A patent/CN1072938A/zh active Pending
- 1992-11-24 ZA ZA929098A patent/ZA929089B/xx unknown
- 1992-12-24 US US07/996,545 patent/US5286554A/en not_active Expired - Fee Related
-
1993
- 1993-09-14 US US08/121,399 patent/US5340856A/en not_active Expired - Fee Related
-
1994
- 1994-05-19 US US08/245,773 patent/US5380775A/en not_active Expired - Fee Related
- 1994-05-19 US US08/245,772 patent/US5412010A/en not_active Expired - Fee Related
- 1994-05-24 FI FI942399A patent/FI942399A/fi unknown
- 1994-05-24 NO NO941921A patent/NO941921L/no unknown
Cited By (5)
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CN101591511B (zh) * | 2008-03-12 | 2015-08-12 | 通用电气公司 | 用于结合复合材料的粘合制剂 |
CN102731729A (zh) * | 2012-07-10 | 2012-10-17 | 常州华日新材有限公司 | 二次粘结不饱和聚酯树脂的制备方法 |
CN102731729B (zh) * | 2012-07-10 | 2014-11-26 | 常州华日新材有限公司 | 二次粘结不饱和聚酯树脂的制备方法 |
CN110892019A (zh) * | 2017-06-27 | 2020-03-17 | 日立汽车系统株式会社 | 不饱和聚酯树脂组合物及使用其的电气设备 |
CN110892019B (zh) * | 2017-06-27 | 2021-10-26 | 日立安斯泰莫株式会社 | 不饱和聚酯树脂组合物及使用其的电气设备 |
Also Published As
Publication number | Publication date |
---|---|
ATE137787T1 (de) | 1996-05-15 |
ZA929089B (en) | 1994-05-24 |
JP3159988B2 (ja) | 2001-04-23 |
NO941921L (no) | 1994-07-15 |
JPH07501570A (ja) | 1995-02-16 |
EP0614476A1 (en) | 1994-09-14 |
FI942399A0 (fi) | 1994-05-24 |
US5286554A (en) | 1994-02-15 |
WO1993011193A1 (en) | 1993-06-10 |
FI942399A (fi) | 1994-05-24 |
CA2122466A1 (en) | 1993-06-10 |
US5206077A (en) | 1993-04-27 |
NO941921D0 (no) | 1994-05-24 |
US5380775A (en) | 1995-01-10 |
TW221824B (zh) | 1994-03-21 |
MY130021A (en) | 2007-05-31 |
US5340856A (en) | 1994-08-23 |
AU2877992A (en) | 1993-06-28 |
EP0614476B1 (en) | 1996-05-08 |
US5412010A (en) | 1995-05-02 |
DE69210625T2 (de) | 1996-09-19 |
DE69210625D1 (de) | 1996-06-13 |
BR9206960A (pt) | 1995-11-28 |
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