CN1131127C - 酰基氧化膦光固化砂布 - Google Patents
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B24D3/02—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent
- B24D3/20—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent and being essentially organic
- B24D3/28—Resins or natural or synthetic macromolecular compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
- B24D11/00—Constructional features of flexible abrasive materials; Special features in the manufacture of such materials
- B24D11/001—Manufacture of flexible abrasive materials
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- Manufacturing & Machinery (AREA)
- Polishing Bodies And Polishing Tools (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Finish Polishing, Edge Sharpening, And Grinding By Specific Grinding Devices (AREA)
- Dental Preparations (AREA)
- Laminated Bodies (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Mechanical Treatment Of Semiconductor (AREA)
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Abstract
采用可辐射固化树脂粘合剂制成的磨具例如砂布,如果它们含有二(2,4,6-三甲基苯甲酰基)苯基氧化膦光引发剂,就能够形成更大的粘合剂固化深度。
Description
背景
本发明涉及砂布,尤其涉及其中磨粒用可紫外光固化粘合剂固定就位的砂布。
在砂布的制造过程中,磨粒通常通过接合涂层粘结到背衬材料上,而且在磨粒上放上胶涂层,将它们固定在原位。有时,在上胶涂层上施加超上胶涂层(supersibe coat),以赋予部分特殊性能例如防堵塞性、抗静电特性,或者在使用期间磨粒接触工件的点放置助磨剂。
虽然有时也使用其他的热固性树脂,但是在这种结构中最经常用于接合涂层和上胶涂层的粘合剂过去是而且目前仍然是酚醛树脂。但是这种粘合剂固化慢,需要昂贵的干燥和固化设备来实现。部分因为这个原因,已经有人提出了更快固化的粘合剂包括采用紫外光辐射固化的粘合剂,而且在一定程度上被采用了。
要明白,本文使用的“紫外光固化或可紫外光固化”一词包括能够通过暴露于光谱的可见光或紫外光区的光化光和电子束辐射而固化的树脂。
通过使用多种暴露于紫外光时产生自由基的光引发剂中的一种,可加速这种粘合剂的固化。这些自由基产生剂的种类包括有机过氧化物、偶氮化合物、醌、二苯甲酮、亚硝基化合物、丙烯酰卤、水螅(hydrozones)、巯基化合物、吡喃鎓化合物、三丙烯酰咪唑、二咪唑、氯代烷基三嗪、苯偶姻醚、苯偶酰缩酮、噻吨酮和乙酰苯,包括这些化合物的衍生物。其中最经常使用的是苯偶酰缩酮,例如2,2-二甲氧基-2-苯基乙酰苯(以Irgacure 651商品名购自Ciba Specialty Chemicals),和乙酰苯衍生物例如2,2-二乙氧基乙酰苯(“DEAP”,购自First Chemical Corporation)、2-羟基-2-甲基-1-苯基-1-丙酮(“HMPP”,以商品名Darocur1173购自Ciba Specialty Chemicals)、2-苄基-2-N,N-二甲基氨基-1-(4-吗啉代苯基)-1-丁酮(以Irgacure 369商品名购自Ciba Specialty Chemicals)和2-甲基-1-(4-(甲硫基)苯基)-2-吗啉代-1-丙酮(以Irgacure 907商品名购自Ciba Specialty Chemicals)。
借助于这种光引发剂,所述树脂的固化基本在数分钟内而不是数小时内完成,因此就提供了节约大量成本的机会。但是,它们仍然有缺点,在固体材料存在下,在激活光被遮蔽的区域,经常固化不完全。这种现象会由于加入颜料或填料的结果而发生,但是不存在固体材料下,仅仅因为树脂层特别厚,也会发生该现象。
当树脂施加到磨粒上使圈套部分树脂在固化期间暴露于紫外光时,该遮蔽效应或许可以接受。但是某些新产品通过加入粘合剂而偏离了接合/磨粒/上胶结构,而且磨粒呈混合物形式,混合物中固化的粘合剂既将混合物粘合到背衬基材上又起磨粒分散于其中的基质的作用。该混合物可以以均匀层形式沉积到基材上或以包含许多复合材料重复图案的图案形式沉积,每种复合材料都含有分散于粘合剂中的磨粒,形成所谓的有结构或设计的磨料。会认识到,在这种制品中,遮蔽效应非常大,而且会限制可以使用的磨粒粒度和可以沉积到基材上的磨料层/粘合层的厚度。
不完全固化尤其在树脂接触基材的结构部分中不好,因为它导致对基材的粘合性差,而且粘合性差又会导致研磨性能差。然而,这正是该影响最明显之时,因为此时固化深度和遮蔽效应最明显。
目前已经发现了一种新光引发剂,在不借助于热固化引发剂情形下,在固化可紫外光固化树脂至比迄今认为可能达到的深度更深方面意外地有效。这会导致这样的可能性,即较大的复合材料能够构成部分设计的磨料制品。这也可能免除热引发剂而使树脂完全固化。
发明的描述
本发明包括制造包含由可紫外光固化树脂粘合剂粘结的磨粒的研磨器具的方法,其中树脂粘合剂存在于包含二(2,4,6-三甲基苯甲酰基)苯基氧化膦作为光引发剂的配制物中。
本发明尤其很适用于制造砂布,但它也适用于制造其他研磨器具例如薄磨轮和较薄的段。也包括其中轮状固体基材的周边带有较薄磨料涂层的磨轮。然而,本发明最易于适用制造砂布,其中磨粒在可辐射固化粘合剂中的浆料用来形成基材上的研磨表面。砂布优选带有凸纹图案表面,或其上有图案的表面(设计的研磨器具),如USP5,014,468、USP5,152,917、USP5,833,724和USP5,840,088所述。
可辐射固化粘合剂能够是通过辐射引发机理发生固化的粘合剂中的任意一种。这些树脂通常包括具有可聚合丙烯酸酯或甲基丙烯酸酯侧基的单体的聚合物和共聚物。它们包括丙烯酸化的氨基甲酸酯、环氧化合物、异氰酸酯和异氰脲酸酯,尽管它们经常与没有(甲基)丙烯酸酯基团的单体例如N-乙烯基吡咯烷酮共聚。也已知丙烯酸化的聚酯和氨基塑料是有用的。也发现某些烯键式不饱和化合物可以由光引发技术聚合。最经常使用的粘合剂以丙烯酸化的环氧和/或丙烯酸化的氨基甲酸酯为基础,而且选择配方来平衡刚性(主要反映聚合物链之间的交联密度)和反映聚合物链长的模量。通过为粘合剂配方选择合适比率的单和/或二-和/或三官能组分,就能够获得合适的刚性。模量的控制能够例如通过选择低聚物组分和/或通过向配方中加入热塑性树脂来实现。要明白所有这些变化都包括于本发明中,只要配制物的辐射固化可通过使用二(2,4,6-三甲基苯甲酰基)苯基氧化膦光引发剂而加快。
通常,粘合剂配制物的树脂组分的聚合被二(2,4,6-三甲基苯甲酰基)苯基氧化膦对之很敏感的紫外光辐射引发。但是树脂也能够在其他辐射例如可见光、电子辐射或其他光化辐射作用下聚合。要明白所有这些树脂都包括于“可辐射固化”一词中。
为用来制造本发明研磨器具的粘合剂配制物的基本组分的引发剂是酰基氧化膦,要明白该词包括具有下式的化合物:其中X、Y和Z中的至少一个选自具有式R-CO-的基团,其中R是氢或取代或未取代的烷基、芳基、烷芳基、芳烷基或杂环基团,不含这种酰基的X、Y和Z中的任何一个是氢或取代或未取代的烷氧基或苯氧基或取代或未取代的烷基、芳基、烷芳基、芳烷基或杂环基团。BTBPPO(二(2,4,6-三甲基苯甲酰基)苯基氧化膦)以Irgacure 819商品名购自Ciba Specialty Chemicals。氧化膦是购自BASF的2,4,6-三甲基苯甲酰基二苯基氧化膦(为Lucirin TPO)和2,4,6-三甲基苯甲酰基乙氧基苯基氧化膦(为Lucirin LR8893)。
因此,如果需要,二(2,4,6-三甲基苯甲酰基)苯基氧化膦引发剂能够单独使用或也可与光引发剂甚至热引发剂组合使用。
当使用磨料/粘合剂配制物时,也可加入其他组分,包括而不局限于:填料例如氧化硅、滑石粉、三水合铝等,其他功能性添加剂例如助磨剂、增粘剂、抗静电剂或防堵塞的添加剂和颜料。
优选实施方式的描述
下面参照某些说明本发明及其所提供的优点的优选实施方式描述本发明。但是它们不对本发明范围有任何必要的限制。
实施例1
该实施例说明各种光引发剂的固化深度。丙烯酸酯基粘合剂的标准浆料含有预定量的粒度为P320的氧化铝磨粒。浆料中磨粒的比率是17.39%(体积),浆料中四氟硼酸钾微粒的比率是27.29%(体积)。
将浆料配成差别仅在于浆料中9R75Quinn Violet颜料的含量不同的几种样品。评价4种Irgacure光引发剂:819(二(2,4,6-三甲基苯甲酰基)苯基氧化膦)、651(一种苄基缩酮)、369(一种α-氨基-乙酰苯)和907(一种α-氨基-乙酰苯)。在多种颜料和光引发剂浓度下测量了每次固化的深度。在每种情形下,都将混合物涂布到J-重量聚酯机织物基材上,并以50英尺/分钟(15.2米/分钟)的速度通过由600瓦V灯泡和300瓦H灯泡组成的紫外光源(Fusion UVSystems,Inc.马里兰州)下方。固化深度由下述方法测量。将混合物倒入箔容器(直径为1.5英寸(3.81厘米)、深度为0.375英寸(0.95厘米)至0.25英寸(0.635厘米)深)。使其通过UV单元。取出任何多余的未固化树脂,接着,测量固化部分的厚度作为固化深度。
结果如图1(a、b和c)中的三维图所示。在每种情形下,关系图都显示了两种光引发剂的固化深度的比率。因此,大于1的光引发剂深度比率说明其固化深度比与之对照的光引发剂的大。
从对比含有二(2,4,6-三甲基苯甲酰基)苯基氧化膦光引发剂(819)的配制物与含有常规的苄基缩酮引发剂(651)的配制物的图1(a)可见,酰基氧化膦光引发剂形成一致的较大的固化深度。图1(b)说明含有α-氨基-乙酰苯光引发剂(369)的配制物比量几乎与819相同的651好。图1(c)说明不是所有的α-氨基-乙酰苯性能都同样地好,因为907比651差很多。
为了得到光引发剂性能的更完整的认识,测量了固化涂层与聚酯背衬之间的粘合强度。该测试是简单的通过/破坏测试,其中通过将制品向上弯曲成90°直角,来测试固化材料的粘合性,数值1表示制品不分离,0表示会发生任何分离。图2(a、b、c、d)分别记录了4种光引发剂819、369、907和651中的每一种的三维图中的结果。它说明对于酰基氧化膦光引发剂(图2a),仅在最高的颜料负荷和最低光引发剂含量点才破坏。651制品的颜料含量高于0.2%(图2d),就会破坏,与369(图2b)在0.8%或更大的颜料浓度破坏相似,后者除了当光引发剂浓度为4%时,发生破坏前,可容许颜料浓度高达1.6%。光引发剂907(图2c)在所有条件下都破坏,除了颜料含量低于0.1%,而且光引发剂浓度至少为4%时。这些图清楚地证明了图1中的评价,并加入了关于对基材粘合性的认识,该认识令人信服地证明了819二(2,4,6-三甲基苯甲酰基)苯基氧化膦光引发剂可给出比最好的α-氨基乙酰苯(369)好得多的令人满意的粘合性数值范围。
实施例2
在本实施例中,使用三种配制物制成具有设计表面的砂布。在每种情形下,使用同样的丙烯酸酯粘合剂,以及粒度为P320的17.39%(体积)氧化铝磨料和27.79%(体积)四氟硼酸钾。
使用的背衬是X重量棉机织物,采用USP5,833,724所述的压花技术形成设计的磨料表面。加上的图案是三螺旋线,每英寸25条线。
采用下述方法评价设计的三种磨料性能,它们的区别仅在于加入到粘合剂/磨料配制物中的光引发剂不同。
采用修改的121Fss Ring Test方法,对上述实施例样品进行研磨测试。在每种情形下,使用6.4厘米×152.4厘米的带,而且带以1524smpm的速度运动。该带在16psi(110KN/m2)压力下与304不锈钢圈工件(17.8厘米外径O.D.,15.2厘米外径I.D.和3.1厘米宽)接触。带后的接触轮是7英寸(17.8厘米)60肖氏硬度的平面橡胶轮。工件以3smpm速度运动。
将20个圈预粗糙化至起始Ra为80微英寸。然后研磨每隔1分钟,测量切削量。用每个带对20个圈共研磨20分钟,记录切削物料的总量。
在每种情形下,测量1分钟之后的起始切削量和20分钟之后的总切削量。结果如下表所示。配制物用所用的Irgacure光引发剂标明。根据本发明制备的砂布以粗体表示。表中最后一行评价了购买的常规的非设计磨料的砂布制品。
砂布 | 起始切削量(gm) | 累积切削量(gm) |
Irgacure 819 | 11.9 | 163.6 |
Irgacure 369 | 11.4 | 150.6 |
Irgacure 651 | 10.4 | 130.3 |
R245 | 10.3 | 68.6 |
从该表中会知道,本发明的砂布在该决定性的“真实应用”测试中,很轻松地就比采用如实施例1中评价的性能较好的配制物制成的相似制品好。
实施例3
在本实施例中,评价了含有同样丙烯酸酯基粘合剂和17.62%(体积)碳化硅磨粒(粒度150)和27.62%(体积)四氟硼酸钾的配制物的固化深度和粘合性。图3比较了这些配制物的固化深度。这些配制物的不同仅在于使用的光引发剂的性质不同。将每种配制物都沉积到X重量棉机织物背衬。每种配制物都在两种条件下进行评价:没有表面处理和有表面处理,表面处理中碳化硅磨粒(与配制物中的相似)和助磨剂的混合物与四氟硼酸钾的重量比为2∶1。
对这些制品进行实施例1所述的粘合性测试。在表中,“1”表示通过,“0”表示破坏。
光引发剂 | 紫外光源* | 没有涂层 | 有涂层表面 |
2%819 | 400瓦(V灯泡) | 1 | 1 |
2%819 | 600瓦(V灯泡) | 1 | 1 |
4%819 | 400瓦(V灯泡) | 1 | 1 |
4%819 | 600瓦(V灯泡) | 1 | 1 |
2%819/1173* | 400瓦(V灯泡) | 1 | 0 |
2%819/1173* | 600瓦(V灯泡) | 1 | 0 |
4%819/1173* | 400瓦(V灯泡) | 1 | 1 |
4%819/1173* | 600瓦(V灯泡) | 1 | 1 |
2%369 | 400瓦(V灯泡) | 1 | 0 |
2%369 | 600瓦(V灯泡) | 1 | 1 |
4%369 | 400瓦(V灯泡) | 1 | 0 |
4%369 | 600瓦(V灯泡) | 1 | 0 |
2%369/1173* | 400瓦(V灯泡) | 1 | 0 |
2%369/1173* | 600瓦(V灯泡) | 1 | 0 |
4%369/1173* | 400瓦(V灯泡) | 1 | 0 |
4%369/1173* | 600瓦(V灯泡) | 1 | 0 |
2%651 | 600瓦(D灯泡) | 1 | 0 |
4%651 | 600瓦(D灯泡) | 1 | 0 |
1173*指Darocure1173(2-羟基-2-甲基-1-苯基-1-丙酮,或HMPP),它是以该商品名购自Ciba Special Chemicals的光引发剂。
紫外光源*:在每种情形下,除了所指出的辐射源以外,包括从300瓦H灯泡发出的辐射。
示出混合物时,存在的组分的比率如下:819/1173(1∶3)和369/1173(1∶3)。
实施例4
在本实施例中,采用这样的评价技术,其中在20psi(138KN/m2)下研磨5/8”×23/8”×93/4”(15.9mm×60.3mm×247.7mm)钛工件,来评价各种设计磨料对6AL-4V钛的切削功率。40D肖氏硬度的平面橡胶接触轮用作接触轮。带速度是3000sfpm(914.4smpm),工件以7sfpm(2.1smpm)往复运动。
配制物以下述两种图案中的一种沉积到X重量棉机织物背衬上:三螺旋线(TH),每英寸25条线;锥体图案(P),每英寸25条锥体线。通过将图案压花至沉积在基材上的浆料表面,可形成图案。在每种情形下,使用购自FusionUV Systems Inc.(马里兰州)的300瓦V灯泡和300瓦H灯泡,实施UV固化。
在每种情形下,15分钟后测量总切削量。结果如下表所示。
图案 | 使用的光引发剂 | 总切削量(gm) |
25P | 4%819 | 21.7 |
25P | 1%819+3%1173 | 19.6 |
25P | 1%819+3%651 | 18.3 |
25P | 1%819+3%184 | 19 |
25TH | 4%819 | 29.1 |
25TH | 2%819 | 23.0 |
25TH | 1%819+3%1173 | 22.6 |
25TH | 1%819+3%651 | 21.5 |
XCF0457* | 12.9 |
*XCF047是购买的采用碳化硅磨粒制成的非设计的磨料。
实施例5
在本实施例中,比较了由三种不同光引发剂得到的固化深度。将每种引发剂加入到实施例1中使用的粘合剂中,但是没有其他添加剂或成分与引发剂一同存在。加入量是1%(重量),将粘合剂/引发剂混合物施涂到基材上,当基材在光源下以13.4米/分钟的速度移动时,对涂覆的基材实施由300瓦D灯泡发出的辐射。在第二种评价中,辐射源是600瓦D灯泡,在光源下通过的速度也是13.4米/分钟。
评价的引发剂是Irgacure 1700(25%DMBAPO与75%HMPP)和Irgacure4265(50%TPO与50%HMPP),它们与单独的Irgacure 1173(HMPP)比较。结果如下表所示:
UV光源 | 固化深度 | ||
1700 | 1173 | 4265 | |
300瓦D灯泡 | 2.75毫米 | 1.35毫米 | 1.85毫米 |
600瓦D灯泡 | 3.95毫米 | 1.8毫米 | 2.12毫米 |
因此,显然,酰基膦引发剂与其他引发剂的混合物形成的固化深度比总量相同的任一种混合组分大。
从上述实施例中提供的数据,可簋明白酰基氧化膦光引发剂可以单独使用或与其他光引发剂组合使用,以保证增大的固化深度和对基材更好的粘合,而且结果可提供良好的总切削量,可完全满足或超过商业上的期望值。
Claims (8)
1.一种制造研磨器具的方法,该方法包括:提供磨粒和包含可辐射固化树脂和二(2,4,6-三甲基苯甲酰基)苯基氧化膦光引发剂的可固化粘合剂配制物,并通过暴露于激活辐射使粘合剂配制物固化,使得树脂至少部分固化,而且磨粒以彼此之间的固定空间关系进行固定。
2.如权利要求1所述的方法,其中所述的二(2,4,6-三甲基苯甲酰基)苯基氧化膦光引发剂在混合物中与酮光引发剂一同存在。
3.如权利要求1所述的方法,其中所述的配制物的可辐射固化树脂成分含有前体配制物,它一旦固化就会提供至少一种选自带丙烯酸酯或甲基丙烯酸酯侧基的单体的聚合物和共聚物中的聚合物。
4.如权利要求1所述的方法,其中在粘合剂配制物的树脂成分固化之前,将所述的粘合剂配制物施涂到背衬材料片上。
5.如权利要求4所述的方法,其中在粘合剂配制物沉积到背衬材料之前,将所述的磨粒分散于粘合剂配制物中。
6.如权利要求5所述的方法,其中在粘合剂配制物的树脂成分的固化完成之前,将所述的磨料/粘合剂混合物沉积到背衬材料上并成型,形成凸纹结构的重复图案。
7.如权利要求1所述的方法,其中在粘合剂配制物的树脂成分固化之前,将所述的磨粒分散于粘合剂配制物中,并使粘合剂/磨料混合物成形成研磨器具的形状。
8.如权利要求7所述的方法,其中所述的器具是磨轮。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101829961A (zh) * | 2010-05-26 | 2010-09-15 | 苏州远东砂轮有限公司 | 一种高精密聚酯砂布布基处理工艺 |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030017797A1 (en) * | 2001-03-28 | 2003-01-23 | Kendall Philip E. | Dual cured abrasive articles |
BRPI0416947A (pt) * | 2003-11-26 | 2007-02-13 | 3M Innovative Properties Co | método para abradar uma superfìcie de uma peça de trabalho |
CA2647881C (en) * | 2006-04-04 | 2012-02-14 | Saint-Gobain Abrasives, Inc. | Infrared cured abrasive articles and method of manufacture |
US20070243798A1 (en) * | 2006-04-18 | 2007-10-18 | 3M Innovative Properties Company | Embossed structured abrasive article and method of making and using the same |
US7410413B2 (en) * | 2006-04-27 | 2008-08-12 | 3M Innovative Properties Company | Structured abrasive article and method of making and using the same |
CN101925441B (zh) * | 2007-12-31 | 2013-08-14 | 3M创新有限公司 | 经等离子处理的磨料制品及其制造方法 |
US9740922B2 (en) | 2008-04-24 | 2017-08-22 | Oblong Industries, Inc. | Adaptive tracking system for spatial input devices |
US8628597B2 (en) * | 2009-06-25 | 2014-01-14 | 3M Innovative Properties Company | Method of sorting abrasive particles, abrasive particle distributions, and abrasive articles including the same |
US8425278B2 (en) * | 2009-08-26 | 2013-04-23 | 3M Innovative Properties Company | Structured abrasive article and method of using the same |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5152917A (en) * | 1991-02-06 | 1992-10-06 | Minnesota Mining And Manufacturing Company | Structured abrasive article |
US5833724A (en) * | 1997-01-07 | 1998-11-10 | Norton Company | Structured abrasives with adhered functional powders |
US5840088A (en) * | 1997-01-08 | 1998-11-24 | Norton Company | Rotogravure process for production of patterned abrasive surfaces |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI82866C (fi) * | 1985-06-24 | 1991-04-25 | Siemens Ag | Foerfarande foer framstaellning av strukturerade vaermebestaendiga skikt och deras anvaendning. |
EP0259727A3 (de) * | 1986-09-11 | 1989-02-08 | Siemens Aktiengesellschaft | Verfahren zur Herstellung wärmebeständiger strukturierter Schichten auf Epoxidharzbasis |
EP0259723B1 (de) * | 1986-09-11 | 1993-04-07 | Siemens Aktiengesellschaft | Verfahren zur Herstellung wärmebeständiger strukturierter Schichten |
US5014468A (en) * | 1989-05-05 | 1991-05-14 | Norton Company | Patterned coated abrasive for fine surface finishing |
ZA941879B (en) * | 1993-03-18 | 1994-09-19 | Ciba Geigy | Curing compositions containing bisacylphosphine oxide photoinitiators |
CA2134156A1 (en) * | 1993-11-22 | 1995-05-23 | Thomas P. Klun | Coatable compositions, abrasive articles made therefrom, and methods of making and using same |
US5543262A (en) * | 1995-02-24 | 1996-08-06 | International Paper Company | Benzanthrone polymerization gate in photopolymerizable compositions |
US5700302A (en) * | 1996-03-15 | 1997-12-23 | Minnesota Mining And Manufacturing Company | Radiation curable abrasive article with tie coat and method |
US5692950A (en) * | 1996-08-08 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Abrasive construction for semiconductor wafer modification |
SG53043A1 (en) * | 1996-08-28 | 1998-09-28 | Ciba Geigy Ag | Molecular complex compounds as photoinitiators |
JPH10249735A (ja) * | 1997-03-17 | 1998-09-22 | Kougi Kk | 砥石並びにその製造方法及び製造装置 |
-
1998
- 1998-12-16 US US09/212,664 patent/US6048375A/en not_active Expired - Lifetime
-
1999
- 1999-12-08 KR KR10-2001-7007521A patent/KR100402505B1/ko not_active IP Right Cessation
- 1999-12-08 EP EP99968094A patent/EP1150802B1/en not_active Expired - Lifetime
- 1999-12-08 WO PCT/US1999/029101 patent/WO2000035633A1/en active IP Right Grant
- 1999-12-08 PL PL99349913A patent/PL190320B1/pl not_active IP Right Cessation
- 1999-12-08 ID IDW00200101292A patent/ID28978A/id unknown
- 1999-12-08 CA CA002354586A patent/CA2354586C/en not_active Expired - Fee Related
- 1999-12-08 BR BR9916191-5A patent/BR9916191A/pt not_active IP Right Cessation
- 1999-12-08 DE DE69909329T patent/DE69909329T2/de not_active Expired - Lifetime
- 1999-12-08 AU AU24780/00A patent/AU741650B2/en not_active Ceased
- 1999-12-08 NZ NZ511774A patent/NZ511774A/en not_active IP Right Cessation
- 1999-12-08 CZ CZ20012166A patent/CZ296498B6/cs not_active IP Right Cessation
- 1999-12-08 JP JP2000587930A patent/JP3802347B2/ja not_active Expired - Fee Related
- 1999-12-08 CN CN99814346A patent/CN1131127C/zh not_active Expired - Fee Related
- 1999-12-08 HU HU0104570A patent/HU223653B1/hu not_active IP Right Cessation
- 1999-12-08 AT AT99968094T patent/ATE244106T1/de active
- 1999-12-08 RU RU2001116724/02A patent/RU2205739C2/ru not_active IP Right Cessation
- 1999-12-15 CO CO99078517A patent/CO5070707A1/es unknown
- 1999-12-15 AR ARP990106441A patent/AR020553A1/es active IP Right Grant
- 1999-12-17 TW TW088122102A patent/TWI242482B/zh not_active IP Right Cessation
-
2001
- 2001-05-17 ZA ZA200104038A patent/ZA200104038B/en unknown
- 2001-06-15 NO NO20012967A patent/NO317822B1/no not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5152917A (en) * | 1991-02-06 | 1992-10-06 | Minnesota Mining And Manufacturing Company | Structured abrasive article |
US5152917B1 (en) * | 1991-02-06 | 1998-01-13 | Minnesota Mining & Mfg | Structured abrasive article |
US5833724A (en) * | 1997-01-07 | 1998-11-10 | Norton Company | Structured abrasives with adhered functional powders |
US5840088A (en) * | 1997-01-08 | 1998-11-24 | Norton Company | Rotogravure process for production of patterned abrasive surfaces |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101829961A (zh) * | 2010-05-26 | 2010-09-15 | 苏州远东砂轮有限公司 | 一种高精密聚酯砂布布基处理工艺 |
CN101829961B (zh) * | 2010-05-26 | 2011-08-31 | 苏州远东砂轮有限公司 | 一种高精密聚酯砂布布基处理工艺 |
Also Published As
Publication number | Publication date |
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HUP0104570A2 (en) | 2002-11-28 |
TWI242482B (en) | 2005-11-01 |
EP1150802B1 (en) | 2003-07-02 |
NO20012967D0 (no) | 2001-06-15 |
AU2478000A (en) | 2000-07-03 |
CN1330583A (zh) | 2002-01-09 |
CA2354586C (en) | 2004-09-28 |
CZ20012166A3 (cs) | 2002-04-17 |
ID28978A (id) | 2001-07-19 |
ATE244106T1 (de) | 2003-07-15 |
PL349913A1 (en) | 2002-10-07 |
NO317822B1 (no) | 2004-12-13 |
NO20012967L (no) | 2001-06-15 |
CA2354586A1 (en) | 2000-06-22 |
AU741650B2 (en) | 2001-12-06 |
KR100402505B1 (ko) | 2003-10-22 |
EP1150802A1 (en) | 2001-11-07 |
CZ296498B6 (cs) | 2006-03-15 |
PL190320B1 (pl) | 2005-11-30 |
KR20010080763A (ko) | 2001-08-22 |
WO2000035633A1 (en) | 2000-06-22 |
RU2205739C2 (ru) | 2003-06-10 |
DE69909329D1 (de) | 2003-08-07 |
DE69909329T2 (de) | 2004-05-27 |
JP3802347B2 (ja) | 2006-07-26 |
JP2002532266A (ja) | 2002-10-02 |
US6048375A (en) | 2000-04-11 |
AR020553A1 (es) | 2002-05-15 |
CO5070707A1 (es) | 2001-08-28 |
HU223653B1 (hu) | 2004-11-29 |
BR9916191A (pt) | 2001-09-04 |
ZA200104038B (en) | 2002-08-19 |
NZ511774A (en) | 2003-05-30 |
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