CN1419620A - 含包括大单体的粘结剂的纸涂布滑爽剂 - Google Patents
含包括大单体的粘结剂的纸涂布滑爽剂 Download PDFInfo
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- CN1419620A CN1419620A CN01806993A CN01806993A CN1419620A CN 1419620 A CN1419620 A CN 1419620A CN 01806993 A CN01806993 A CN 01806993A CN 01806993 A CN01806993 A CN 01806993A CN 1419620 A CN1419620 A CN 1419620A
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Abstract
本发明涉及一种含作为粘结剂的共聚物的纸涂布滑爽剂，所述共聚物通过自由基聚合烯属不饱和化合物获得。本发明的特征是至少一种烯属不饱和化合物为含有至少一个可共聚烯属不饱和基团、数均分子量500至50000g/mol和至少一个羧基的聚合物(以下简称为烯属不饱和聚合物)。
Description
本发明涉及含作为粘结剂的共聚物的纸涂布滑爽剂，所述共聚物通过自由基聚合烯属不饱和化合物获得，其中至少一种烯属不饱和化合物为具有至少一个可共聚烯属不饱和基团、数均分子量500至50000g/mol和至少一个羧基的聚合物(以下简称为烯属不饱和聚合物)。
纸涂布滑爽剂基本上含有颜料和粘结剂。粘结剂用于将颜料固定于纸上并确保获得的涂层中的粘结性。
在印刷过程中如胶版印刷机中，由于印刷油墨的高粘性，强拉伸力作用于涂布纸(纸涂层)上。纸涂层对该力提供的阻力称为抗粘连性。抗干粘连与抗湿粘连之间存在差别。湿抗粘连在含水胶印中是特别重要的，因为在第二个印刷装置中，印刷油墨与水润湿的纸接触，因此纸涂层在这些条件下必须具有足够的粘结力。
为提高抗粘连性，聚合物通常含有酸基。这些聚合物描述于，例如WO 97/00776中。
具有含多个酸基的烯属不饱和聚合物作为组分的乳液聚合物形成WO95/04767的主题。
对于迄今已知的纸涂布滑爽剂，粘结剂的粘结力和由此抗粘连性仍然不足。
本发明的一个目的是提供具有改进的抗粘连性的纸涂布滑爽剂。
我们已发现，本发明通过在开始时定义的纸涂布滑爽剂得以实现。
该新纸涂布滑爽剂含有开始时定义的共聚物作为粘结剂。
该共聚物可通过自由基聚合，优选通过乳液聚合可共聚的烯属不饱和化合物获得。
至少一种烯属不饱和化合物是具有至少一个可聚合的烯属不饱和基团、数均分子量500至50000g/mol和至少一个羧基的聚合物(以下简称为烯属不饱和聚合物)。烯属不饱和基团和羧基的含量基于聚合物链的含量。烯属不饱和聚合物链宜含有一个或两个烯属不饱和基团，特别优选一个烯属不饱和基团。该或一个(若存在多个)烯属不饱和基团特别优选在相应的聚合物链中作为端基存在。该烯属不饱和基团特别为丙烯酰基或甲基丙烯酰基，优选甲基丙烯酰基。
该烯属不饱和聚合物优选含有多于2个、特别优选多于4个、更特别优选多于8个羧基。
该烯属不饱和聚合物优选由能够自由基聚合的化合物合成，并且可相应通过自由基聚合这些化合物获得。
优选该烯属不饱和聚合物含至少50重量％、优选80重量％(甲基)丙烯酸C1-C10烷基酯、(甲基)丙烯酸或其混合物。
更特别优选该烯属不饱和聚合物含至少50重量％、特别是至少80重量％丙烯酸或甲基丙烯酸。优选甲基丙烯酸。
烯属不饱和聚合物的重均分子量Mn优选为800至20,000，特别优选1,000至10,000g/mol。
Mn通过凝胶渗透色谱(聚乙酸标准物和水作为洗脱剂)测定。
烯属不饱和聚合物优选通过在过渡金属配合物如钴螯和配合物作为分子量调节剂存在下自由基聚合制备。该方法被称为催化链转移聚合(CCT)并描述于例如WO 95/04767和该公开文件中引用的文献中。
该共聚物优选含至少0.1、特别优选至少0.3、更特别优选至少1、特别是至少2重量％的烯属不饱和聚合物。通常含量不超过30、特别是20、特别优选15重量％。
该共聚物整体上优选组成如下：
a)30至99.9重量％选自(甲基)丙烯酸C1-C10烷基酯、至多20个碳原子的羧酸的乙烯基酯、至多20个碳原子的乙烯基芳烃、烯属不饱和腈、乙烯基卤、1至10个碳原子的醇的乙烯基醚或烯丙基醚、具有2至8个碳原子和1或2个双键的脂族烃或这些单体的混合物的主单体
b)0.1至30重量％该烯属不饱和聚合物，和
c)0至40重量％其它烯属不饱和化合物。
该共聚物整体上优选组成如下：
a)50至99.5重量％主单体
b)0.5至20重量％烯属不饱和聚合物，和
c)0至30重量％其它单体。
该共聚物特别优选组成如下：
a)60至99重量％主单体
b)1至20重量％烯属不饱和聚合物，和
c)0至20重量％其它单体。
主单体的例子是具有C1-C10烷基的(甲基)丙烯酸烷基酯，如甲基丙烯酸甲酯、丙烯酸甲酯、丙烯酸正丁酯、丙烯酸乙酯和丙烯酸2-乙基己酯
(甲基)丙烯酸烷基酯的混合物也是特别合适的。
1至20个碳原子的羧酸的乙烯基酯为例如月桂酸乙烯酯、硬脂酸乙烯酯、丙酸乙烯酯、戊酸乙烯酯和乙酸乙烯酯。
合适的乙烯基芳族化合物是乙烯基甲苯、α-和对甲基苯乙烯、α-丁基苯乙烯、4-正丁基苯乙烯、4-正癸基苯乙烯，优选苯乙烯。腈的例子是丙烯腈和甲基丙烯腈。
乙烯基卤化物是被氯、氟或溴取代的烯属不饱和化合物，优选氯乙烯或偏二氯乙烯。
乙烯基醚的例子是乙烯基甲基醚或乙烯基异丁基醚。1至4个碳原子的醇的乙烯基醚是优选的。
具有2至8个碳原子和1或2个烯属双键的烃的例子为丁二烯、异戊二烯和氯丁二烯、乙烯和丙烯
优选的主单体是丙烯酸和甲基丙烯酸C1-C10烷基酯，特别是丙烯酸和甲基丙烯酸C1-C8烷基酯，在每一情况下丙烯酸酯是特别优选的。
特别优选丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯、丙烯酸正己酯、丙烯酸辛酯和丙烯酸2-乙基己酯及这些单体的混合物。
共聚物优选为基于丙烯酸酯的共聚物，即该共聚物包括至少60重量％的(甲基)丙烯酸C1-C20烷基酯或其与乙烯基芳烃的混合物。
基于丁二烯的共聚物也是优选的，即该聚合物包括至少60重量％丁二烯或其与乙烯基芳烃的混合物。
除了主单体和烯属不饱和聚合物外，该聚合物还可含有其它烯属不饱和化合物，例如包括羧基、磺酸基或膦酸基的单体。优选羧基。例子是丙烯酸、甲基丙烯酸、衣康酸、马来酸或富马酸。
还可提及含羟基的单体，特别是(甲基)丙烯酸C1-C10羟烷基酯或(甲基)丙烯酰胺。
此外，合适的其它烯属不饱和化合物是苯氧基乙基二醇单(甲基)丙烯酸酯、丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯和氨基(甲基)丙烯酸酯，如(甲基)丙烯酸2-氨基乙酯。
聚合物的玻璃转化温度优选为低于50℃，特别是-40至+50℃，特别优选-20至+30℃，更特别优选-10至+25℃，尤其是-5至+20℃。
聚合物的玻璃转化温度可通过常规方法，如差热分析或差示扫描量热法测定(例如，参见ASTM 3418/82，中点温度)。
该共聚物优选通过乳液聚合制备，并因此为乳液聚合物。
然而，该制备还可通过例如溶液聚合然后分散于水中进行。
在乳液聚合中，将离子和/或非离子乳化剂和/或保护胶体或稳定剂用作表面活性剂。
合适保护胶体的详细描述出现在Houben-Weyl Methoden derOrganischen，Vol XIV/1，Makromolekulare Stoffe，Georg-Thieme-Verlag，Stuttgart，1961，p411至420中。合适的乳化剂是阴离子、阳离子和非离子乳化剂。与保护胶体相反，唯一优选使用其分子量通常低于2000g/mol的乳化剂作助表面活性剂。当使用表面活性物质的混合物时，当然各组分必须相互相容。若没有把握，可借助很少几个初步试验检查。使用的表面活性物质宜是阴离子和非离子表面活性剂。
常规的辅助乳化剂是，例如，乙氧基化脂肪醇(乙氧基化程度：3至50，烷基C8至C36)，乙氧基化单-、二-和三烷基苯酚(乙氧基化程度：3至50，烷基C4至C9)，磺基丁二酸二烷基酯的碱金属盐以及烷基硫酸的碱金属和铵盐(烷基C8至C12)，乙氧基化链烷醇的碱金属和铵盐(乙氧基化程度：4至30，烷基C12至C18)，乙氧基化烷基苯酚的碱金属和铵盐(乙氧基化程度：3至50，烷基C4至C9)，链烷磺酸的碱金属和铵盐(烷基C12至C18)和烷基芳基磺酸的碱金属和铵盐(烷基C9至C18)。
进一步优选的乳化剂是通式II的化合物
其中R5和R6各自为氢或C4-C14烷基且不同时为氢，C和Y为碱金属离子和/或铵离子。R5和R6优选各自为6至18个碳原子、特别是6、12或16个碳原子的线性或支化烷基、碳原子或氢原子。R5和R6不同时为氢。X和Y优选为钠、钾或铵离子，特别优选钠。特别有利的化合物是其中X和Y各自为钠、R5为12个碳原子的支化烷基和R6为氢或R5的那些。通常使用含50至90重量％单烷基化产品的工业混合物，例如Dowfax2A1(Dow Chemical Company商标)。
合适的乳化剂也描述于Houben-Weyl Methoden der Organischen，Vol14/1，Makromolekulare Stoffe，Georg-Thieme-Verlag，Stuttgart，1961，p192至208中。
乳化剂的商品名为例如Dowfax2 A1、EmulanNP 50、DextrolOC 50、Emulgator 825、Emulgator 825 S、EmulanOG、TexaponNSO、Nekanil904 S、LumitenI-RA、Lumiten E 3065、Disponil FES 77、Lutensol At 18、Steinapol VSL、Emulphor NPS 25。
表面活性剂的用量通常为0.1至10重量％，按待聚合的单体计。
用于乳液聚合的水溶性引发剂是，例如，过二硫酸的铵和碱金属盐如过二硫酸钠、过氧化氢或有机过氧化物如氢过氧化叔丁基。
氧化还原引发剂体系是特别合适的。
氧化还原引发剂体系由至少一种无机还原剂和至少一种无机或有机氧化剂构成。
氧化组分为，例如，上述用于乳液聚合的引发剂中的一种。
还原组分为，例如，亚硫酸的碱金属盐如亚硫酸钠，碱金属亚硫酸氢盐，焦亚硫酸的碱金属盐如焦亚硫酸钠，脂族醛和酮的酸式亚硫酸加成化合物，如丙酮酸式亚硫酸，或还原剂如羟甲烷亚磺酸和其盐，或抗坏血酸。氧化还原剂体系可在其金属组分可以多个价态存在的可溶金属化合物存在下使用。
常规的氧化还原引发剂体系是，例如，抗坏血酸/硫酸亚铁(II)、过二硫酸钠、氢过氧化叔丁基/焦亚硫酸钠、氢过氧化叔丁基/羟甲烷亚磺酸钠。各组分，例如还原组分，也可为混合物，例如羟甲烷亚磺酸的钠盐与焦亚硫酸钠的混合物。
所述化合物通常以水溶性形式使用，其中浓度低限通过分散体中可接受的水量来确定，而浓度高限通过相应化合物在水中的溶解度确定。通常该浓度为0.1至30重量％、优选0.5至20重量％、特别优选1.0至10重量％，按溶液计。
引发剂的量通常为0.1至10，优选0.5至5重量％，基于要聚合的单体。在乳液聚合中可以使用多种不同的单体。
在聚合中，可以使用例如约0至0.8重量份(按100重量份要聚合的单体重量计)调节剂，借助该调节剂使分子量降低。例如，具有巯基的化合物如叔丁基硫醇、巯基甘醇酸乙酯、巯基乙醇、巯丙基三甲氧基硅烷或叔十二烷基硫醇是合适的。
乳液聚合一般在30至130℃、优选50至95℃下进行。聚合介质可仅为水，或为水和与其混溶的液体如甲醇的混合物。优选仅使用水。乳液聚合可以间歇工艺和进料工艺(包括分部或梯度工艺)进行。优选进料工艺，其中开始加入一些聚合原料、加热至聚合温度并部分聚合，然后在保持聚合下将剩余的聚合原料以连续、逐步或浓度梯度叠加方式，通常通过空间上分离的多路原料(其中一路或多路含纯或乳化形式的单体)加入聚合段中。在聚合中，例如为更好地调节颗粒尺寸在开始时还可加入聚合物。
在自由基水乳液聚合中引发剂加入聚合容器中的方式是本领域普通技术人员已知的。可以在开始时全部加入聚合容器中或以其在自由基水乳液聚合中消耗的速率连续或逐步加入。这具体取决于引发剂体系的化学性能和聚合温度。优选在开始时加入一部分，然后将剩余的以消耗速率加入聚合段。
为除去残余单体，通常还在实际乳液聚合结束后，即单体转化至少95％后加入引发剂。
在进料工艺中，可将各组分自反应器上、反应器侧或自反应器下面加入反应器中。
在乳液聚合中，通常获得具有固含量15至75重量％、优选40至75重量％的聚合物的含水分散体。
对于反应器的高空时收率，优选具有极高固含量的分散体。为能够实现固含量＞60重量％，应建立双模态或多模态颗粒尺寸，因为否则粘度会变得太高并且不再能够操作分散体。产生新的一代颗粒，例如可通过加入种子(EP 81083)、通过加入过量乳化剂或通过微乳液进行。与低粘度和高固含量组合相关的另一优点是在高固含量下涂布性能的改进，产生新的颗粒可在任何所需时刻进行。取决于低粘度所需的颗粒尺寸分布。
共聚物优选以水分散体形式使用。
本发明纸涂布滑爽剂含优选1至50重量％，特别是5至20重量％的共聚物作为粘结剂，按纸涂布滑爽剂中的颜料含量计(即基于无溶剂的固体共聚物本身的数据)。
除了粘结剂外，颜料通常为纸涂布滑爽剂的主要组分，通常使用的颜料为例如硫酸钡、碳酸钙、磺基铝酸钙、高岭土、滑石、二氧化钛、氧化锌、白垩石、涂布粘土或有机颜料，如颗粒形式的塑料。
除了粘结剂和颜料外，纸涂布滑爽剂可含有另一些添加剂。
纸涂布滑爽剂可含有，例如分散剂。合适的分散剂是例如聚磷酸或聚丙烯酸的聚阴离子(聚盐)，其存在量通常为0.1至3重量％(按颜料量计)。
此外，纸涂布滑爽剂可含有助粘结剂。天然助粘结剂的例子是淀粉、酪蛋白、明胶、藻酸盐和大豆蛋白，改性天然产品的例子是羟乙基纤维素、甲基纤维素、羧甲基纤维素和阳离子改性淀粉。然而，还可使用基于乙酸乙烯酯或丙烯酸乙烯酯的常规合成助粘结剂。
这些助粘结剂可以例如0.1至10重量％(按颜料量计)的量存在。
为制备纸涂布滑爽剂，将组分按已知方式混合，其中聚合物通常以水分散体、悬浮液或溶液形式使用。
纸涂布滑爽剂的含水量通常被调至25至75重量％，按纸涂布滑爽剂总量计(包括水)。
纸涂布滑爽剂可通过常规方法施于要涂布的纸上(参见，Ullmann’sEncyclopadie der Technischen Chemie，第4版，Vol.17，p 603以下)。
涂布本发明纸涂布滑爽剂的纸具有高的抗干和湿粘连(纸涂布滑爽剂的粘结)。因此，它们特别适合其中印刷油墨在涂布纸上施加高拉伸力的胶印。
涂布本发明纸涂布滑爽剂的纸显示良好的可印刷性。该纸特别适合胶印工艺。
实施例
I.制备简称为PMA的聚甲基丙烯酸
(烯属不饱和聚合物)
初始投料混合物：17.5mg CoBF
0.75g VA 044
450.00g去离子水
进料1：190.00g甲基丙烯酸
9.00g CoBF
工序：将去离子水加热至沸腾，并通入N2气体。同时将N2气体通入进料1中。将N2强制通入装置中并将后者排空，将此工序进行5次。将初始投料混合物吸入该装置中，不允许空气同时吸入其中。将该混合物加热至55℃，然后开始加入进料1。操作原料容器类似于投料混合物。在1.5小时内慢慢滴加原料1，进一步聚合1.5小时，然后进行冷却。分析数据
SC*：固含量，**标准物：聚丙烯酸
| 最终样品 | |
| SC：* | 25.5％ |
| 转化率 | 89％ |
| pH： | 2.2 |
| GPC：** | |
| Mn | 3,400 |
| Mw： | 7,200 |
洗脱液：H2OII：制备聚合物分散体
将初始投料混合物加热至85℃并聚合15分钟。然后，用2小时计量加入单体乳液并用2.5小时计量加入引发剂(6.29g过二硫酸钠在H2O中的1％浓度溶液)。然后将聚合进行1小时，接着冷却。
实施例1(对比例)
初始投料混合物：18g原料胶乳(聚苯乙烯种子，30nm)
457g水
5重量％如下单体乳液
单体乳液：330g丙烯酸正丁酯
270g苯乙烯
24g丙烯酸
6.7g Dowfax 2 Al(在H2O中，45％浓度)
564g水
实施例2
制备类似于实施例1，不同的是仅使用12g丙烯酸和另外的12gPMA。
实施例3
制备类似于实施例1，不同的是仅使用6g丙烯酸和另外的18g PMA。
实施例4
制备类似于实施例1，不同的是不使用丙烯酸而代之以24g PMA。
共聚物的组成(重量％)在下表1中给出：
| 实施例 | 1 | 2 | 3 | 4 |
| nBA | 52.9 | 52.9 | 52.9 | 52.9 |
| St | 43.3 | 43.3 | 43.3 | 43.3 |
| AA | 3.8 | 1.9 | 0.9 | - |
| PMA | - | 1.9 | 1.9 | 3.8 |
III.制备纸涂布滑爽剂
通过将如下组分一起搅拌制备纸涂布滑爽剂。
10重量份共聚物
70重量份Hydrocarb(碳酸钙)
30重量份Amazon(高岭土)
0.4重量份聚盐(分散剂)
0.05重量份NaOH
0.5重量份CMC 7L2T(羧甲基纤维素)
固含量为65重量％(含水)。
测试性能特征
使用的纸为基重70g/m2的非木浆涂布纸。在实验室涂布仪上将纸涂布滑爽剂以10g/m2的量涂于一侧上。干燥用IR灯进行。在测试特性之前，将纸通过实验室压延机(一对辊，辊隙压力：2000N/cm)四次。
抗干粘连性
自要测试的纸纵向切割尺寸33×3cm的条，并将这些条在27℃和相对湿度50％下在调节室中贮存15小时。
然后将这些条在印刷装置(IGT印刷性能测试仪AC2/AIC2)中用标准油墨(印刷油墨3808，购自Lorilleux-Lefrance)印刷。
将测试条在连续增加速度(最大速度200cm/sec)下通过印刷装置。将自纸涂布滑爽剂出现10次撕裂(粘连)的速度(单位cm/sec)作为抗干粘连的测量值。
抗温粘连性
按如上所述制备测试条
测试条在印刷工艺前被水润湿，并相应设定使用的印刷机(IGT印刷性能测试仪AC2/AIC2)。
印刷在恒定速度0.6cm/s下进行。
可观察到自纸涂布滑爽剂或纸的撕裂，为未印刷区域。为测定抗湿粘连，用油墨密度计测定油墨的密度(与固体色调对比，％)。该油墨密度越高，抗湿粘连性越好。
胶印试验
纸：
自要测试的纸纵向切割尺寸240×46mm的条。
为进行试验：
将合适量的印刷油墨送入上墨辊中，并使后者运行1分钟。然后插入印刷板并上油墨30秒。
印刷速度为1m/s。将纸条送回带有印刷纸条的印刷样品支撑物上的起始位置。经过规定时间后，在不改变印刷板下再次开始印刷工艺。将此工艺重复数次。
每通过一次后，目测评估纸条印刷一侧的粘连。记录直至第一出现粘连的通过次数。对明显的粘连，最后一次通过仅记作一半(例如在第三次通过后的强粘连记作2.5)。
结果：
直至出现第一次粘连的印刷工艺次数
| 来自如下的粘结剂 | 抗干粘连cm/s | 抗湿粘连 | 胶印试验 |
| 实施例1 | 50 | 42.1 | 2.5 |
| 实施例2 | 51 | 41.7 | 3 |
| 实施例3 | 85 | 45.6 | 5 |
| 实施例4 | 86 | 47.2 | 5 |
Claims (11)
1.一种含作为粘结剂的共聚物的纸涂布滑爽剂，所述共聚物通过自由基聚合烯属不饱和化合物获得，其中至少一种烯属不饱和化合物为含有至少一个可共聚烯属不饱和基团、数均分子量500至50000g/mol和至少一个羧基的聚合物(以下简称为烯属不饱和聚合物)。
2.如权利要求1的纸涂布滑爽剂，其中烯属不饱和聚合物含一个或两个可共聚烯属不饱和基团。
3.如权利要求1或2的纸涂布滑爽剂，其中烯属不饱和聚合物的烯属不饱和基团为丙烯酰基或甲基丙烯酰基。
4.如权利要求1或3的纸涂布滑爽剂，其中烯属不饱和聚合物含2种以上的羧酸。
5.如权利要求1或4的纸涂布滑爽剂，其中烯属不饱和聚合物由能够自由基聚合的化合物合成。
6.如权利要求1或5的纸涂布滑爽剂，其中烯属不饱和聚合物可通过在过渡金属配合物作为分子量调节剂存在下自由基聚合获得。
7.如权利要求1或6的纸涂布滑爽剂，其中共聚物通过如下物质合成：
a)30至99.9重量％选自(甲基)丙烯酸C1-C10烷基酯、至多20个碳原子的羧酸的乙烯基酯、至多20个碳原子的乙烯基芳烃、烯属不饱和腈、乙烯基卤、1至10个碳原子的醇的乙烯基醚或烯丙基醚、具有2至8个碳原子和1或2个双键的脂族烃或这些单体的混合物的主单体
b)0.1至30重量％烯属不饱和聚合物，和
c)0至40重量％其它烯属不饱和化合物。
8.如权利要求1至7任何一项的共聚物在纸涂布滑爽剂中作为粘合剂的用途。
9.一种用如权利要求1至7任何一项的纸涂布滑爽剂涂布的纸。
10.如权利要求9的纸在胶印工艺中的用途。
11.可通过如权利要求10的用途获得的印刷纸。
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Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3105779A1 (de) * | 1981-02-17 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | Waessrige dispersionen, ihre herstellung und verwendung |
| FR2523984A1 (fr) * | 1982-03-24 | 1983-09-30 | Rhone Poulenc Spec Chim | Emulsions aqueuses d'interpolymere, procede pour les preparer et utilisations notamment comme liants pour le couchage du papier |
| EP0320594B2 (en) | 1987-12-14 | 1998-04-15 | Nippon Shokubai Co., Ltd. | Aqeous crosslinkable resin dispersions, method of their production and use thereof |
| GB9316221D0 (en) | 1993-08-05 | 1993-09-22 | Zeneca Ltd | Production of polymer emulsions |
| DE4442729A1 (de) * | 1994-12-01 | 1996-06-05 | Basf Ag | Alkenylnitril enthaltende Bindemittel für Papierstreichmassen |
| FR2729150A1 (fr) * | 1995-01-06 | 1996-07-12 | Rhone Poulenc Chimie | Poudres redispersables dans l'eau de polymeres filmogenes a structure "coeur/ecorce" |
| DE19522399A1 (de) * | 1995-06-21 | 1997-01-02 | Basf Ag | Verwendung von Papierstreichmassen mit hohem Butadiengehalt im Offsetdruck |
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2000
- 2000-03-28 DE DE10015262A patent/DE10015262A1/de not_active Withdrawn
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2001
- 2001-03-27 WO PCT/EP2001/003469 patent/WO2001073199A1/de active IP Right Grant
- 2001-03-27 AT AT01936144T patent/ATE254691T1/de not_active IP Right Cessation
- 2001-03-27 CN CNB018069932A patent/CN1234937C/zh not_active Expired - Fee Related
- 2001-03-27 DE DE50101000T patent/DE50101000D1/de not_active Expired - Fee Related
- 2001-03-27 AU AU2001262138A patent/AU2001262138A1/en not_active Abandoned
- 2001-03-27 EP EP01936144A patent/EP1268931B1/de not_active Expired - Lifetime
- 2001-03-27 US US10/240,267 patent/US6852423B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101057036B (zh) * | 2004-11-12 | 2012-03-28 | 巴斯福股份公司 | 基于颜料-聚合物混杂物的涂纸浆液 |
| CN107428432A (zh) * | 2015-03-31 | 2017-12-01 | 比勒鲁迪克斯那斯公司 | 具有可拉伸覆层的基底 |
| CN107428432B (zh) * | 2015-03-31 | 2019-06-04 | 比勒鲁迪克斯那斯公司 | 具有可拉伸覆层的基底 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1268931A1 (de) | 2003-01-02 |
| AU2001262138A1 (en) | 2001-10-08 |
| US6852423B2 (en) | 2005-02-08 |
| DE50101000D1 (de) | 2003-12-24 |
| WO2001073199A1 (de) | 2001-10-04 |
| DE10015262A1 (de) | 2001-10-04 |
| ATE254691T1 (de) | 2003-12-15 |
| CN1234937C (zh) | 2006-01-04 |
| EP1268931B1 (de) | 2003-11-19 |
| US20030068478A1 (en) | 2003-04-10 |
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