CN107709398B - 聚氨酯基粘合剂体系 - Google Patents
聚氨酯基粘合剂体系 Download PDFInfo
- Publication number
- CN107709398B CN107709398B CN201680024170.0A CN201680024170A CN107709398B CN 107709398 B CN107709398 B CN 107709398B CN 201680024170 A CN201680024170 A CN 201680024170A CN 107709398 B CN107709398 B CN 107709398B
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- CN
- China
- Prior art keywords
- adhesive system
- diamine
- adhesive
- isocyanate
- curing component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000005012 migration Effects 0.000 claims description 13
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
本发明涉及粘合剂体系，其包含作为树脂组分的异氰酸酯基封端的聚氨酯预聚物和作为固化剂的多元醇混合物，所述多元醇混合物包含至少一种烷氧基化二胺。本发明还涉及所述粘合剂体系作为粘合剂/密封剂材料的用途，特别是作为用于食品包装的层压粘合剂的用途。
Description
本发明涉及一种粘合剂体系，其包含作为树脂组分的异氰酸酯基封端的聚氨酯预聚物和作为固化剂的多元醇混合物，所述多元醇混合物含有至少一种烷氧基化二胺。本发明还涉及所述粘合剂体系作为粘合剂/密封剂，特别是作为食品包装的层压粘合剂的用途。
双组分粘合剂体系，特别是基于多元醇和异氰酸酯基封端(NCO封端的)化合物的粘合剂体系长期以来一直是现有技术的一部分。它们的用途例如在金属加工工业、汽车工业、电气工业、包装工业和建筑行业中用作粘合剂、密封剂、填料或浇铸化合物。基于双组分聚氨酯粘合剂的粘合剂体系，特别是包装工业中使用的粘合剂体系的一个缺点是在粘合剂体系中所包含的游离单体多异氰酸酯的毒性。用技术用语来讲，这些游离的单体多异氰酸酯能够在涂层或粘合剂中“迁移”，或者甚至能够在一定程度上进入被涂覆或粘合的材料中。与水汽接触时，迁移物的异氰酸酯基团连续反应形成氨基，在此过程中，由芳香族多异氰酸酯形成所谓的芳香族伯胺(PAA)。这些迁移物迁移通过包装材料可能造成包装产品的污染。由于PAA的毒性特别令人担忧，从而使其在包装行业，特别是在食品包装领域尤其不受欢迎，立法机关对食品包装的渗出物进行了限制，必须注意这些规定。因此，关键的是用于生产复合膜的粘合剂在食品被包装的时候必须已经充分固化，从而不超过限制。因此，在包装生产出来之后(其中复合膜尤其重要)，在包装食品之前复合膜必须储存至反应已进行得足够充分，使得不再能检测出PAA的迁移或结果低于规定的上限。
因此，根据能够迁移的游离单体多异氰酸酯的量，在包装材料符合食品安全标准之前需要等待较长的时间才能使用。出于经济性和物流的考虑，希望在包装材料可以进一步使用之前将所需的储存时间减至最短。
由于单体多异氰酸酯的迁移而可能产生的另一个不良影响被称为防密封效果，这是在生产塑料复合膜制成的袋子或购物袋时产生的。塑料复合膜通常含有基于脂肪酸酰胺的润滑剂。迁移的单体多异氰酸酯与脂肪酸酰胺和水分的反应在膜表面生成具有可能高于塑料膜密封温度的熔点的脲化合物。这导致在要密封在一起的膜部件之间形成不同的防密封层，这阻碍了形成均匀密封接缝。
存在多种为人熟知的用于防止单体芳香族多异氰酸酯迁移的方法。其中包括减少在合成异氰酸酯基封端的聚氨酯预聚物中使用的芳香族多异氰酸酯的量；异氰酸酯单体的微量蒸馏；使用具有多级固化机理的预聚物混合物；以及在NCO封端的预聚物中使用特殊的聚醚主链，如专利WO2010/091806中所述。
已知方法的缺点包括体系的反应性降低(芳香族多异氰酸酯的量的减少)，从而可能需要使用催化剂，这同样可能带来有毒性的风险；必须使用某些昂贵的工艺和设施(微量蒸馏)；或者难以规划对预聚物合成工艺(使用特殊聚醚主链)的必要改进。此外，专利WO2010/091806中描述的预聚物具有自动催化的缺点，因此需要至少四周的储存时间来成胶。
此外，许多已知的体系具有的缺点是常用的金属催化剂，例如基于锡的催化剂或使用例如1,4-二氮杂双环[2.2.2]辛烷(DABCO)的胺催化剂具有短的适用期，这是使用层压机施涂的一个缺点，特别是用量较大时。此外，在这种体系中，相对大量的催化剂不会使迁移时间显著降低。
因此，本发明所解决的问题是提供一种粘合剂体系，其克服这些缺点，并且尽管使用常规的具有高浓度异氰酸酯单体的异氰酸酯基封端聚氨酯(PU)预聚物，但是显示出快速的化学固化，因此迁移物含量迅速降低，使得包装材料在生产之后即能够尽快使用，从而使得等待时间最小化。此外，粘合剂体系的适用期应足够长以允许通过常用的层压机进行加工。
本发明人出人意料地发现，通过使用特殊的多元醇混合物来固化异氰酸酯基封端的聚氨酯预聚物，可以解决这个问题，所述多元醇混合物含有至少一种烷氧基化二胺。
因此，本发明的第一方面涉及一种粘合剂体系，其包含(i)含有至少一种异氰酸酯基封端的聚氨酯预聚物的树脂组分；和(ii)含有至少一种烷氧基化二胺的固化剂。
本发明的另一方面涉及使用本发明所述的粘合剂体系制造粘合剂/密封剂的方法。将所述树脂组分与固化组分按照异氰酸酯基团与NCO反应性基团1:1-4:1，优选1:1-3:1，更优选1.2:1-2.5:1，特别优选1.2:1-1.8:1的(摩尔)比例混合，其中，NCO反应性基团优选为羟基。
本发明的另一方面涉及制备复合膜的方法，其中使用本发明所述的粘合剂体系将至少两个相同或不同的塑料膜在全部或部分表面上粘合在一起，还涉及以这种方式制备的复合膜。
本发明的另一方面涉及此处所述的粘合剂体系在粘合剂配制品中的用途，特别是用作双组分粘合剂，优选用作无溶剂或含溶剂的层压粘合剂用于在基材之间生产低迁移的粘合剂粘合，其中所述基材特别选自纸、纸板、木材、塑料、金属或者石材。
最后，本发明还涉及含有0.5-20重量％，特别是1-10重量％的至少一种烷氧基化二胺和(基于多元醇混合物)80-99.5重量％，优选90-99重量％的至少一种多元醇的组合物在基于聚氨酯预聚物并且是芳香族端异氰酸酯基封端的粘合剂配制品中作为固化组分的用途，所述组合物用于在基材之间生成低迁移的粘合剂粘接，其中所述基材优选为膜形式的基材，特别优选是塑料膜。
除非另有说明，本发明中提及的分子量都是指数均分子量(Mn)。除非另有说明，本发明中提及的所有分子量都是利用凝胶渗透色谱(GPC)，以THF作为洗脱剂，根据DIN55672，特别是DIN 55672-1测得的数值。
除非另有说明，羟值(OH值)是根据DIN 53240测定的。
化合物的OH官能度应理解为其平均OH官能度。它表示每分子羟基的平均数量。化合物的平均OH官能度可以根据数均分子量和羟值来计算。
除非另有说明，异氰酸酯含量都是(NCO含量，％NCO)是根据DIN EN ISO 11909测定的。
化合物的NCO官能度应理解为其平均NCO官能度。它表示每分子NCO基团的平均数量。化合物的平均NCO官能度可以根据数均分子量和NCO值计算。
可以使用OH值和NCO含量计算NCO与OH基团的摩尔比(NCO指数)。
本发明所说的“至少一个”是指一个或更多，例如1、2、3、4、5、6、7、8、9或更多。涉及到成分，该数值代表所述成分的种类而不是分子的绝对数量。例如，“至少一种多元醇”是指至少一种多元醇，因此可使用一种多元醇或多种不同多元醇的混合物。提到重量时，所指的数值是针对组合物/混合物中所含的所述种类的所有化合物，这意味着组合物/混合物除了所述量的对应化合物外不包含任何其它该种类的化合物。
除非另有明确说明，与本发明所述组合物相关的所有百分比都是指重量百分比(重量％)，所有情形下都是基于所讨论的混合物。
本发明中针对数值使用的词语“约”是指所述数值的±10％，优选±5％。
出人意料地发现，本发明所述的粘合剂体系非常适合作为粘合剂/密封剂，其中它们显示出很长的适用期，而且还显示出完全的化学固化，从而导致迁移物含量迅速降低。粘合剂体系优选“低迁移”的。在下文中，表述“低迁移”应被理解为在1-14天，优选2-6天后，芳香族伯胺(PAA)的含量测得值小于0.2μg PAA/100mL填料(“填料”定义为由使用所述的粘合剂体系胶合的膜组成的包装的含量)。为此按照方法L00.00-6中规定的§64LFGB[德国食品和饲料代码]测定芳香族伯胺含量。为了根据§64LFGB测试PAA的迁移量，将由薄膜复合材料制成的袋子装满模拟食物(含有3重量％乙酸的水溶液)，在70℃下储存2小时。然后在衍生化之后用光度计测定PAA含量。这必须达到每100mL模拟食物少于0.2μg PAA的含量。这对应于2ppb，这也恰好是所述方法的检测限。
树脂组分的NCO封端的PU预聚物通过使多元醇或多元醇混合物与化学计量过量的多异氰酸酯反应而得到。用于制备预聚物的多元醇可以是通常用于聚氨酯合成的任何多元醇，例如单体多元醇、聚酯多元醇、聚醚多元醇、聚酯醚多元醇、聚碳酸酯多元醇，或上述两种或更多种的混合物。
聚醚多元醇可以由很多种含有一个或多个伯醇或仲醇基团的醇制得。作为制备不含叔氨基的聚醚的引发剂，可以使用例如下列化合物或其混合物：水、乙二醇、1,2-丙二醇、甘油、丁二醇、丁三醇、三羟甲基乙烷、季戊四醇、己二醇、己三醇、3-羟基苯酚、三羟甲基丙烷、辛二醇、新戊二醇、1,4-羟甲基环己烷、双(4-羟基苯基)二甲基甲烷和山梨醇。优选使用乙二醇、1,2-丙二醇、甘油和三羟甲基丙烷，特别优选乙二醇和1,2-丙二醇，在特别优选的示例性实施方案中，使用1,2-丙二醇。
适合作为环醚用于生产上述聚醚的是环氧烷烃，例如环氧乙烷、环氧丙烷、环氧丁烷、表氯醇、氧化苯乙烯或四氢呋喃，或这些环氧烷烃的混合物。其中优选使用环氧丙烷、环氧乙烷、或四氢呋喃或其混合物。特别优选使用环氧丙烷或环氧乙烷或其混合物。最优选使用环氧丙烷。
聚酯多元醇可以例如通过使低分子量醇，特别是乙二醇、二甘醇、新戊二醇、1,6-己二醇、1,4-丁二醇、1,2-丙二醇、甘油、或三羟甲基丙烷与己内酯反应而得到。其它适合作为多官能醇用于生产聚酯多元醇的有1,4-羟甲基环己烷、2-甲基-1,3-丙二醇、1,2,4-丁三醇、三甘醇、四甘醇、聚乙二醇、一缩二丙二醇、聚丙二醇、一缩二丁二醇和聚丁二醇。
其它合适的聚酯多元醇可以通过缩聚反应来制备。二官能和/或三官能的醇因此可以与不足量的二羧酸或三羧酸、二羧酸或三羧酸的混合物或其反应性衍生物缩合。合适的二羧酸为例如己二酸或琥珀酸以及含有高达16个C原子的高阶同系物，以及不饱和二羧酸，如马来酸或富马酸，以及芳香族二羧酸，特别是异构化苯二甲酸，如邻苯二甲酸、间苯二甲酸或对苯二甲酸。合适的三羧酸的例子包括柠檬酸或偏苯三酸。上述酸可以单独使用或两种或更多种混合使用。特别合适的醇为1,6-己二醇、1,4-丁二醇、乙二醇、二甘醇、新戊二醇、3-羟基-2,2-二甲基丙基3-羟基-2,2-二甲基丙酸酯、或三羟甲基丙烷，或其两种或更多种的混合物。特别合适的酸是邻苯二甲酸、间苯二甲酸、对苯二甲酸、己二酸或十二烷二酸或其混合物。具有高分子量的聚酯多元醇的例子包括多官能的，优选双官能的醇(任选与少量的三官能醇一起)与多官能度，优选双官能的羧酸的反应产物。如果可能的话，也可以使用相应的多元羧酸酐或相应的和含有优选1-3个C原子的醇的多元羧酸酯代替游离的多元羧酸。多元羧酸可以是脂肪族的、脂环族的、芳香族的或杂环的。它们可以任选被取代，例如被烷基、烯基或醚基取代。合适的多元羧酸的例子包括琥珀酸、己二酸、辛二酸、壬二酸、癸二酸、十二烷二酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、邻苯二甲酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、内次甲基四氢邻苯二甲酸酐、戊二酸酐、马来酸、马来酸酐、富马酸、二聚体脂肪酸或三聚体脂肪酸，或其两种或多种的混合物。
也可以使用由内酯得到的聚酯，例如基于ε-己内酯的聚酯，也称为“聚己内酯”，或者由羟基羧酸例如ω-羟基己酸得到的聚酯。
然而，也可以使用油脂化学来源的聚酯多元醇。可以例如将至少部分含有烯键式不饱和脂肪酸的脂肪混合物与一种或多种具有1至12个C原子的醇的环氧化甘油三酯完全开环，然后甘油三酯衍生物发生部分酯交换以得到烷基残基中具有1至12个C原子的烷基酯多元醇，从而制备这样的聚酯多元醇。
聚碳酸酯多元醇例如可以通过使二醇，如1,2-丙二醇、1,4-丁二醇或1,6-己二醇、二甘醇、三甘醇或四甘醇或这些二醇的混合物与碳酸二芳基酯，例如碳酸二苯酯或碳酰氯反应而得到。
用于合成预聚物的多元醇的分子量优选为320g/mol-20000g/mol，特别是330g/mol-4500g/mol。平均官能度可以为2-4.5。
在本发明的各种实施方案中，多元醇用于制备NCO封端的聚酯多元醇预聚物，特别是可通过将己二酸和/或间苯二甲酸与二甘醇和/或1,2-丙二醇缩合得到的那些。除了聚酯多元醇之外，也可以选择使用聚醚多元醇，特别是聚丙二醇用于制备NCO封端的预聚物。这些PU预聚物可通过使多异氰酸酯与聚醚和聚酯的混合物反应而获得。在特别优选的实施方案中，NCO封端的预聚物具有聚醚/聚酯聚合物主链。
合适的多异氰酸酯是具有两个或更多个，优选二个至最多约四个的异氰酸酯基团的脂肪族、芳香族和/或脂环族异氰酸酯。在本发明范围内特别优选的是单体多异氰酸酯，特别是单体二异氰酸酯。合适的单体多异氰酸酯的例子包括：1,5-萘二异氰酸酯、2,2-，2,4'-和4,4'-二苯基甲烷二异氰酸酯(MDI)、氢化MDI(H12MDI)、亚二甲苯基二异氰酸酯(XDI)、四甲基亚二甲苯基二异氰酸酯(TMXDI)、二-和四-烷基二苯基甲烷二异氰酸酯、4,4'-二苄基氰酸酯、1,3-亚苯基二异氰酸酯、1,4-亚苯基二异氰酸酯、2,4-和/或2,6-甲苯二异氰酸酯(TDI)、1-甲基-2,4-二异氰酸酯基环己烷、2,2,4-三甲基己烷-1,6-二异氰酸酯、2,4,4-三甲基己烷-1,6-二异氰酸酯、2,3,3-三甲基己烷-1,6-二异氰酸酯、1-异氰酸甲酯基-3-异氰酸酯基-1,5,5-三甲基环己烷(IPDI)、亚磷酸二异氰酸酯、四甲氧基丁烷-1,4-二异氰酸酯、亚乙基-1,2-二异氰酸酯、丁烷-1,4-二异氰酸酯、戊烷-1,5-二异氰酸酯、己烷-1,6-二异氰酸酯(HDI)、十一烷-1,11-二异氰酸酯、十二烷-1,12-二异氰酸酯、二环己基甲烷二异氰酸酯、环己烷-1,4-二异氰酸酯、邻苯二甲酸双异氰酸酯基乙酯、二聚体脂肪酸二异氰酸酯、1,3-环己烷二异氰酸酯、1,4-环己烷二异氰酸酯、1,3-或1,4-四甲基二甲苯二异氰酸酯和赖氨酸酯二异氰酸酯。
至少三官能异氰酸酯的合适例子是通过二异氰酸酯的三聚或低聚获得的多异氰酸酯，例如二异氰酸酯三聚体，或通过二异氰酸酯与含有羟基或氨基的多官能化合物的反应得到的多异氰酸酯。用于制备至少三官能的氰酸酯的含羟基的多官能化合物的合适例子包括甘油、三羟甲基乙烷、季戊四醇、以及糖醇如山梨糖醇、甘露糖醇、异麦芽糖醇、麦芽糖醇和木糖醇。
适于生产三聚体的异氰酸酯的实例是上述二异氰酸酯，特别优选HDI、MDI、TDI或IPDI的三聚产物。
此外，二异氰酸酯和低分子量三醇的加合物，更特别的是芳香族二异氰酸酯和三醇例如三甲醇丙烷或甘油的加合物，也适合作为三异氰酸酯。聚合异氰酸酯也是适用的，例如在蒸馏二异氰酸酯的液相中作为残留物得到的那些。
优选使用的多异氰酸酯是芳香族多异氰酸酯，其中特别优选芳香族二异氰酸酯。因此，本发明的一个优选实施方案，作为多异氰酸酯使用的是选自1,5-亚萘基二异氰酸酯、2,2-，2,4-和/或4,4-二苯基甲烷二异氰酸酯(MDI)、2,4-和/或2,6-甲苯二异氰酸酯(TDI)、四甲基亚二甲苯基二异氰酸酯(TMXDI)、异氰酸酯MDI或TDI三聚产物的单体多异氰酸酯以及它们的混合物。特别优选的是二苯基甲烷二异氰酸酯的异构体，即4,4'-MDI、2,4'-MDI和2,2'-MDI，或它们的混合物。特别优选4,4'-MDI，因为当使用该异构体时，迁移物含量降低特别快。
因此，优选至少一种NCO封端的PU预聚物为由一种或多种聚酯多元醇和芳香族二异氰酸酯制成的芳香族异氰酸酯基封端的PU预聚物。
在本发明的一个特别优选的实施方案中，至少一种NCO封端的PU预聚物是能够由一种或多种聚酯多元醇和MDI得到的MDI封端的聚氨酯预聚物。
根据本发明优选具有聚酯/聚醚聚合物主链的NCO封端的预聚物，特别是由聚酯多元醇、聚丙二醇和MDI制成的，其中聚酯多元醇可通过将己二酸和间苯二甲酸与过量的二甘醇和1,2-丙二醇缩合而得到。
在本发明的一个优选实施方案中，异氰酸酯基封端的聚氨酯预聚位于不具有包含胺引发的聚醚的聚醚聚合物主链。
用于合成预聚物的多异氰酸酯的化学计量过量(以NCO基与OH基的摩尔比计)，优选为1:1-5:1，更优选为2:1-4:1，特别优选2.5:1-3.5:1。
相应预聚物的NCO含量通常为3-20重量％，优选5-17重量％，并且它们的平均NCO官能度为2-3。
由于使用过量的异氰酸酯，NCO封端的PU预聚物通常含有一定量的异氰酸酯单体，特别是芳香族多异氰酸酯单体如MDI。其含量基于树脂组分的总重量通常为0.1-40重量％，例如为20-30重量％。为了使对健康有害的迁移物的量最小化，目标是含量小于1重量％，但是这种树脂组分显示出相对较高的粘度。然而，由于烷氧基化二胺减少了迁移物含量，因此使用含有至少一种烷氧基化二胺的固化组分使得可以使用常规的固化组分，这意味着基于固化组分总重量NCO含量为20-30重量％的那些。
通常，预聚物的分子量(Mn)的范围为500g/mol-100000g/mol，优选600g/mol-25000g/mol，特别优选700g/mol-6000g/mol。
NCO封端的预聚物本身的制备是本领域技术人员已知的，例如通过在反应温度下将液体多元醇与过量的多异氰酸酯混合，并搅拌所得混合物直到NCO值达到恒定来实现。所选择的反应温度范围优选为40℃-180℃，更优选为50℃-140℃。
除了树脂组分之外，根据本发明的粘合剂体系还含有固化组分。所述固化成分含有0.5-20重量％，更优选1-10重量％的至少一种烷氧基化二胺。除了烷氧基化二胺以外，固化成分优选还含有80-99.5重量％，特别是90-99重量％的不同于所述烷氧基化二胺的多元醇。该至少一种多元醇可以是选自前文公开的与制备预聚物相关的那些多元醇中的一种或多种。这些另外的多元醇优选为二-和/或三官能聚醚多元醇，例如如上所述的那些。
合适的烷氧基化二胺的例子包括，但不限于，使用二胺作为起始物可通过聚合环氧乙烷和/或环氧丙烷得到的聚醚多元醇，特别是乙氧基化和/或丙氧基化的亚烷基二胺。合适的二胺的例子包括，但不限于，乙二胺、N,N-二甲基乙二胺、N,N'-二甲基乙二胺、丙二胺、四亚甲基二胺、六亚甲基二胺、2,4-甲苯二胺、2,6-甲苯二胺、二苯基甲烷-2,2'-二胺、二苯基甲烷-2,4'-二胺、二苯基甲烷-4,4'-二胺、异佛尔酮二胺、二环己基甲烷-4,4'-二胺和亚二甲苯基二胺。优选的二胺是乙二胺、N,N-二甲基乙二胺和N,N'-二甲基乙二胺，特别优选乙二胺。
在本发明的多种实施方案中使用的是式1的烷氧基化二胺化合物：
H-[O-CHR-CH2]m-NR'-(CH2)n-NR'-[CH2-CHR-O]m-H(1)其中，
每个R独立地选自H、CH3和CH2-CH3，优选H和CH3，特别优选CH3；
每个R'独立地选自H和-[CH2-CHR-O]m-H，优选-[CH2-CHR-O]m-H；
每个m独立地为1-10，优选1-4，更优选1-2的整数；
n为1-10，优选为1-6，特别优选为2-4的整数，最优选为2。
在优选的实施方案中，烷氧基化二胺是每个乙二胺单元都具有2-8个环氧丙烷/环氧乙烷单元的丙氧基化或乙氧基化/丙氧基化乙二胺。
这种二胺市场上有售，例如商品名为
RA 500、RA 640和RA 800(DowChemicals)。
上述2种或更多种烷氧基化二胺的混合物也适用。
此外，本发明所述的粘合剂体系的各种实施方案可包含至少一种催化剂，优选胺催化剂或基于Sn、Zn、Bi、Zr、V或Ti的金属催化剂。合适的催化剂是现有技术中已知的。然而，粘合剂体系的优选实施方案不含有这样的催化剂。
本发明所述的粘合剂体系特别适合用作粘合剂/密封剂。
因此，本发明的目的是使用本发明所述的粘合剂体系制造粘合剂/密封剂的方法，其中将树脂组分与固化组分按照异氰酸酯基团与NCO反应性基团1:1-4:1，优选为1:1-3:1，更优选为1.2:1-2.5:1，特别优选为1.2:1-1.8:1的比例混合，此处NCO反应性基团优选为羟基。
在两个组分混合60分钟后，由此获得的粘合剂/密封剂的各种实施方案在40℃下的粘度为2000-30000mPas，优选为4000-12000mPas(根据DIN EN ISO 2555，BrookfieldRVT DV 11+，转子号27，剪切速率:20min-1)。
在本发明所述方法的一个种实施方案中，树脂组分和固化组分之间的反应在溶剂存在条件下进行。原则上，本领域技术人员已知的所有溶剂都可以使用，特别是酯、酮、卤代烃、烷烃、烯烃和芳香烃。这些溶剂的例子包括二氯甲烷、三氯乙烯、甲苯、二甲苯、乙酸丁酯、乙酸戊酯、乙酸异丁酯、甲基异丁基酮、乙酸甲氧基丁酯、环己烷、环己酮、二氯苯、二乙基酮、二异丁基酮、二氧六环、乙酸乙酯、乙二醇单丁醚乙酸酯、乙二醇单乙基乙酸酯、乙酸2-乙基己酯、乙二醇二乙酸酯、庚烷、己烷、乙酸异丁酯、异辛烷、乙酸异丙酯、甲基乙基酮、四氢呋喃或四氯乙烯，或两种或更多种所述溶剂的混合物。然而，在优选实施方案中，不使用溶剂。
本发明描述的粘合剂体系适合用作胶合和密封各种基材的双组分粘合剂。这些基材包括例如木材、金属、玻璃、植物纤维、石材、纸、玻璃纸、塑料如聚苯乙烯、聚乙烯、聚丙烯、聚对苯二甲酸乙二醇酯、聚氯乙烯、氯乙烯和偏二氯乙烯的共聚物、醋酸乙烯酯烯烃的共聚物、聚酰胺。基材优选为膜形式的基材，包括但不限于塑料膜和金属膜。用作基材的塑料膜包括由聚丙烯(PP)、聚乙烯(PE)、取向聚丙烯(OPP)、取向聚酰胺(OPA)、尼龙、聚对苯二甲酸乙二醇酯(PET)和聚酯制成的膜。金属膜可以由例如铝、铅或铜组成。
在本发明的特别优选的实施方案中，本发明所述的粘合剂体系用作无溶剂或含溶剂的层压粘合剂，特别是作为食品包装的层压粘合剂。
本发明所述的粘合剂体系可以通过使用所有常规涂覆方法施涂到待粘合的基底上，例如通过喷雾、刮刀涂覆、在使用无溶剂粘合剂体系的情况下三-四-辊涂覆系统、在使用基于溶剂的粘合剂体系的情况下双辊涂覆系统。
本发明的另一个目的是一种生产复合膜的方法，其中至少两个相同或不同的塑料膜使用本发明所述的粘合剂体系在所有或部分表面上粘合在一起。粘合剂体系可以作为双组分粘合剂，使用常规用于这些目的的机器，例如传统的层压机，涂覆到待粘合的膜上。本发明的另一个目的是根据本发明所述的方法制备的使用本发明所述的粘合剂体系的复合膜。所述复合膜特别适用于包装食品、奢侈品以及医药产品。
本发明所述的粘合剂体系可以包含通常的添加剂，例如增塑剂、硅烷、抗氧化剂、UV稳定剂和抗老化剂。优选使用的增塑剂包括邻苯二甲酸酯，例如邻苯二甲酸二辛酯、邻苯二甲酸二-十三烷基酯和邻苯二甲酸丁基苄酯，磷酸酯类如磷酸三甲苯酯，己二酸酯例如己二酸二辛酯，或苯甲酸酯例如丙二醇二苯甲酸酯。
特别使用氨基硅烷、环氧基硅烷或巯基硅烷，尤其是γ-缩水甘油氧基丙基三甲氧基硅烷或γ-氨基丙基三甲氧基硅烷，以提高与玻璃、金属等的粘合性。
为了用作密封化合物，可以向本发明所述的粘合剂体系中加入无机填料，例如炭黑、碳酸钙和二氧化钛等。优选使用高度分散的硅酸，特别是热解硅酸或沉淀硅酸作为具有触变作用的无机填料，并且其触变性能即使在长时间储存之后也保留在本发明所述的粘合剂体系中。
本发明描述的粘合剂体系可用在粘合剂配制品中，所述粘合剂配制品用于在基材之间产生低迁移的粘合剂粘接。基材可以选自上述那些，特别包括塑料膜和金属膜，例如用于食品包装的那些。
上面与粘合剂体系相关的描述的是含有0.5-20重量％，特别是1-10重量％的至少一种烷氧基化二胺，并且含有(基于多元醇混合物)80-99.5重量％，优选90-99重量％的至少一种多元醇的固化组分，并且该固化组合物可以在基于聚氨酯预聚物且是芳香族异氰酸酯基封端的粘合剂配制品中用作固化组分，以便在基材之间生成低迁移粘合剂粘结。基材如上文定义。
此处公开的所有和粘合剂体系相关的实施方案也可以用于这里所述的应用和方法，反之亦然。
下面将基于几个示例性实施方案描述本发明。除非另有说明，含量以重量％表示。
实施例
测试系列1：
实施例1a(不基于本发明)
树脂成分：Loctite Liofol LA 7731(MDI封端的聚醚/聚酯PU预聚物，可从Henkel购得)
固化组分：Loctite Liofol LA 6038(由一缩二丙二醇(DPG)和主要具有仲羟基端基的三官能聚醚多元醇制得的多元醇混合物；可从Henkel购得)。
实施例1b(基于本发明)：如实施例1a，不同之处是将固化组分中的5重量％DPG换成Voranol R800(OH值为780-820mg KOH/g；乙二胺的氧丙烯加合物，可从Dow ChemicalCompany购得)。
实施例1c(基于本发明)：如实施例1a，不同之处是将固化组分中的5重量％DPG换成Voranol R640(OH值为615-665mg KOH/g；乙二胺的氧丙烯加合物，可从Dow ChemicalCompany购得)。
实施例1d(基于本发明)：如实施例1a，不同之处是将固化组分中的5重量％DPG换成Voranol RA500(OH值约500mg KOH/g；乙二胺的氧丙烯加合物，可从Dow ChemicalCompany购得)。
实施例1e(不基于本发明)：如实施例1a，不同之处是将固化组分中的0.05重量％聚醚多元醇换成二月桂酸二辛基锡(DOTL)。
实施例1f(不基于本发明)：如实施例1a，不同之处是将固化组分中的0.1重量％聚醚多元醇换成1,4-二氮杂双环[2.2.2]辛烷(DABCO)。
实施例1g(不基于本发明)：如实施例1a，不同之处是将固化组分中的1重量％聚醚多元醇换成三乙醇胺。
测试系列2：
实施例2a(不基于本发明)：和实施例1a一致。
实施例2b(基于本发明)：和实施例1d一致。
实施例2c(不基于本发明)：和实施例1b一致。
实施例2d(不基于本发明)：如实施例1a，不同之处是将固化组分中的5重量％DPG换成Desmophen V 155(三乙醇胺的氧丙烯加合物，可从Bayer Material Science购得)。
实施例2e(不基于本发明)：如实施例1a，不同之处是将固化组分中的5重量％DPG换成TIPA(三异丙醇胺)。
实施例2f(不基于本发明)：如实施例1a，不同之处是使用由叔胺引发的聚醚多元醇(Voranol Voractiv VM 779，可从Dow Chemical Company购得)、聚丙二醇(PPG2000)和2,4'-/4,4'-MDI(Desmodur 2460，可从Bayer Material Science购得)制备的预聚物替代树脂组分。
使用1.8g/m2粘合剂层压的OPA/PE结构，以通过BfR方法检测填料模拟物(3％乙酸)中的PAA含量。结果如表1所示，显示为PAA的量为pg每100mL填料模拟物。目标值为<2μgPAA/100mL填料模拟物。测试过程中的变化，例如膜的质量和/或涂覆的粘合剂的重量可能对所测得的PAA值有影响。因此，绝对PAA值应仅在同一测试系列中进行比较，此处仅在测试系列1和测试系列2内进行比较。
此外，层间粘合力(VH)根据DIN ISO 53357标准确定。使用切条机，切割15mm宽的复合材料样条以测定层间粘合力。然后用手或在热封颚边缘上分离复合材料。在复合材料已经固化的情况下，将复合材料样条的一端插入乙酸乙酯中可能会有帮助。使用通用拉伸试验机进行测量，拉伸力的范围0-20N(例如来自Instron或Zwick)。将先前分离的复合材料样条夹住，拉伸试验机以100mm/min的抽取速率(draw-off rate)启动；抽取角度为90°(手动保持)，抽取长度为5-10cm(取决于波动范围)。结果表示为层间粘合力，单位N/15mm，并且指示值是三次测量的平均值。在膜的撕裂的情况下，显示最大值。
密封接缝强度(SNH)根据DIN ISO 55529标准测定。为此，OPA/PE结构首先在150℃下自身密封(PE在PE上)1秒，同时在1cm x 15cm的表面上施加650N的力。然后使用通用拉伸试验机测定密封接缝强度，力的范围为0-20N(例如来自Instron或Zwick)。然后使用切条机切割15mm宽的复合材料样条，将复合材料样条夹紧，拉伸试验机以100mm/min的抽取速率启动；抽取角度为90°(手动保持)，抽取长度为5-10cm(取决于波动范围)。结果表示为密封接缝强度，单位是N/15mm，所示值是三次测量的平均值。
在混合后60分钟和40℃下测定粘度(mPa·s)。
还测定了树脂的NCO含量(重量％)和固化剂的OH值(mg KOH/g)。
混合物比例以质量份数表示(g/g)。
表1显示了测量值的概况。
表1：
*材料撕裂或断裂
**粘合剂界面处的分离(粘合剂分离)
***12分钟后25000mPas。20分钟后停止测量。和100000mPas。
结果表明，在基于本发明的粘合剂体系中，PAA值比在固化剂中不含烷氧基化二胺的相应参照体系中下降更快(实施例1b，1c和1d vs.实施例1a。实施例2b和2c vs.实施例2a)。
与参照相比(实施例1g vs.实施例1a)，在固化剂中使用三乙醇胺没有引起PAA值的降低。
与参照相比(实施例2e vs.实施例2a)，在固化剂中使用三异丙醇胺导致PAA值下降更快，但是效果远没有使用烷氧基化二胺时明显(实施例2e vs.实施例2b和2c)。
此外还显示使用锡基催化剂导致PAA值降低更快一些，但也导致粘度增加，这对应于更短的适用期(参见实施例1e vs.实施例1a)。此外，在食品包装中使用锡化合物会有健康方面的顾虑。
如锡基催化剂的情况一样，使用胺催化剂同样造成更高的粘度和更短的适用期。此外，没有观察到PAA值降低的加速(参见实施例1f vs.实施例1a)。
和根据本发明的制剂类似，使用可通过烷氧基化单胺制得的聚醚多元醇的粘合剂体系表现出PAA值快速下降以及低粘度，但是粘合强度值较低(实施例2d vs.实施例2b和2c)。
在树脂包含由叔胺引发的聚醚多元醇制备的异氰酸酯基封端的预聚物的粘合剂体系中，看到类似的结果。在该情况下也测得了与根据本发明的制剂相当的PAA值快速降低和低粘度，但是粘合强度值较差(实施例2f vs.实施例2b和2c)。此外，由于异氰酸酯基封端的聚氨酯预聚物的聚合物主链中的叔氨基催化了异氰酸酯基团，所以具有这种预聚物的树脂显示出降低的储存稳定性。因此在预聚物中检测到对稳定性具有负面影响的自动催化活性。这是基于以下观察结果：在封闭容器中储存不超过四周后，这些预聚物变成了固体。
Claims (27)
1.双组份粘合剂体系，其包含：
(i)含有至少一种异氰酸酯基封端的聚氨酯预聚物的树脂组分；和
(ii)含有至少一种烷氧基化二胺的固化组分，所述固化组分基于该固化组分，包含0.5-20重量％的至少一种烷氧基化二胺和80-99.5重量％的至少一种二-和/或三官能聚醚多元醇。
2.根据权利要求1所述的粘合剂体系，其特征在于，所述至少一种烷氧基化二胺是使用二胺作为起始剂可通过聚合环氧乙烷和/或环氧丙烷而得到的聚醚多元醇。
3.根据权利要求2所述的粘合剂体系，其特征在于，所述至少一种烷氧基化二胺是乙氧基化和/或丙氧基化的亚烷基二胺。
4.根据权利要求2所述的粘合剂体系，其特征在于，所述二胺选自乙二胺、N,N-二甲基乙二胺、N,N'-二甲基乙二胺、丙二胺、四亚甲基二胺、六亚甲基二胺、2,4-甲苯二胺、2,6-甲苯二胺、二苯基甲烷-2,2'-二胺、二苯基甲烷-2,4'-二胺、二苯基甲烷-4,4'-二胺、异佛尔酮二胺、二环己基甲烷-4,4'-二胺和苯二甲胺。
5.根据权利要求2所述的粘合剂体系，其特征在于，所述二胺是乙二胺。
6.根据权利要求1-5中任一项所述的粘合剂体系，其特征在于，所述至少一种烷氧基化二胺是式1的化合物：
H-[O-CHR-CH2]m-NR'-(CH2)n-NR'-[CH2-CHR-O]m-H(1)
其中，
每个R独立地选自H、CH3和CH2-CH3；
每个R'独立地选自H和-[CH2-CHR-O]m-H；
每个m独立地为1-10的整数；
n为1-10的整数。
7.根据权利要求6所述的粘合剂体系，其特征在于，每个R为CH3。
8.根据权利要求6所述的粘合剂体系，其特征在于，每个m独立地为1-2的整数。
9.根据权利要求6所述的粘合剂体系，其特征在于，n为2。
10.根据权利要求6所述的粘合剂体系，其特征在于，所述至少一种烷氧基化二胺是丙氧基化的乙二胺或乙氧基化/丙氧基化的乙二胺，其对于每个乙二胺单元具有2-8个环氧丙烷/环氧乙烷单元。
11.根据权利要求1-5中任一项所述的粘合剂体系，其特征在于，基于所述固化组分，所述固化组分含有1-10重量％的所述至少一种烷氧基化二胺。
12.根据权利要求1-5中任一项所述的粘合剂体系，其特征在于，所述异氰酸酯基封端的聚氨酯预聚物含有异氰酸酯基团，以及任选存在的芳香族多异氰酸酯单体。
13.根据权利要求12所述的粘合剂体系，其特征在于，所述异氰酸酯基团是亚甲基二苯基二异氰酸酯(MDI)基团。
14.根据权利要求1-5中任一项所述的粘合剂体系，其特征在于，所述异氰酸酯基封端的聚氨酯预聚物具有聚酯/聚醚聚合物主链。
15.根据权利要求1-5中任一项所述的粘合剂体系，其特征在于，所述异氰酸酯基封端的聚氨酯预聚物不具有包含胺引发的聚醚的聚醚聚合物主链。
16.使用根据权利要求1-15中任一项所述的粘合剂体系制造粘合剂/密封剂的方法，其特征在于，将所述树脂组分与固化组分按照异氰酸酯基团与NCO反应性基团1:1-4:1的比例混合。
17.根据权利要求16所述的方法，其特征在于，将所述树脂组分与固化组分按照异氰酸酯基团与NCO反应性基团1.2:1-2.5:1的比例混合。
18.根据权利要求16所述的方法，其特征在于，将所述树脂组分与固化组分按照异氰酸酯基团与NCO反应性基团1.2:1-1.8:1的比例混合。
19.复合膜的制造方法，其特征在于，使用根据权利要求1-15中任一项所述的粘合剂体系将至少两个相同或不同的塑料膜在全部或部分表面上粘合在一起。
20.根据权利要求19所述的方法制造的复合膜。
21.根据权利要求1-15中任一项所述的粘合剂体系在粘合剂配制品中的用途，所述粘合剂配制品是用于在基材之间产生低迁移的粘合剂粘接。
22.根据权利要求21所述的用途，其特征在于，所述基材是膜形式的基材。
23.根据权利要求21所述的用途，其特征在于，所述基材是塑料膜。
24.组合物在基于聚氨酯预聚物并且是芳香族异氰酸酯基封端的粘合剂配制品中作为固化组分的用途，其中基于多元醇混合物，所述组合物含有0.5-20重量％的至少一种烷氧基化二胺和80-99.5重量％的至少一种二-和/或三官能聚醚多元醇，所述组合物用于在基材之间产生低迁移的粘合剂粘接。
25.根据权利要求24所述的用途，其特征在于，所述组合物含有1-10重量％的至少一种烷氧基化二胺和90-99重量％的至少一种二-和/或三官能聚醚多元醇。
26.根据权利要求24所述的用途，其特征在于，所述基材是膜形式的基材。
27.根据权利要求24所述的用途，其特征在于，所述基材是塑料膜。
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| PL (1) | PL3288995T3 (zh) |
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| WO (1) | WO2016173926A1 (zh) |
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| TWI756219B (zh) * | 2016-05-10 | 2022-03-01 | 美商陶氏全球科技有限責任公司 | 包括胺引發之多元醇之雙組分無溶劑黏著劑組合物 |
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| CN108138022A (zh) * | 2016-09-29 | 2018-06-08 | Dic株式会社 | 粘接剂、使用其的层叠膜、以及粘接剂用多元醇组合物 |
| JP2020505493A (ja) * | 2017-01-27 | 2020-02-20 | ダウ グローバル テクノロジーズ エルエルシー | 二成分無溶剤接着剤組成物 |
| DE102017121003A1 (de) | 2017-09-12 | 2019-03-14 | Schaeffler Technologies AG & Co. KG | Drosseleinrichtung mit stoffschlüssig an einem Gehäuse angebrachter Blendenkomponente; Leitungssystem, Betätigungssystem und Kupplung |
| RU2020120892A (ru) * | 2017-12-27 | 2021-12-24 | Дау Глоубл Текнолоджиз Ллк | Двухкомпонентные клеевые композиции, не содержащие растворитель, для склеивания с полимерными барьерными подложками |
| EP3827037A1 (en) * | 2018-07-26 | 2021-06-02 | Sun Chemical Corporation | Flexible food packaging laminates |
| AR117147A1 (es) * | 2018-11-28 | 2021-07-14 | Dow Global Technologies Llc | Proceso para formar un laminado con adhesivo sin solvente |
| WO2020199175A1 (en) * | 2019-04-04 | 2020-10-08 | Dow Global Technologies Llc | Solventless adhesive composition and method for preparing thereof |
| CN113710764B (zh) * | 2019-04-24 | 2023-11-28 | 汉高股份有限及两合公司 | 双组分无溶剂聚氨酯层合粘合剂组合物 |
| US20220177753A1 (en) * | 2019-05-15 | 2022-06-09 | Dow Global Technologies Llc | Two-component adhesive compositions, articles prepared with same and preparation methods thereof |
| BR112023023861A2 (pt) * | 2021-06-01 | 2024-01-30 | Dow Global Technologies Llc | Composição adesiva de dois componentes, processo para produzir um laminado, e, laminado |
| CN114479744A (zh) * | 2021-12-31 | 2022-05-13 | 广州市昌鹏实业有限公司 | 一种双组分油性光学压敏胶的研制 |
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- 2016-04-21 KR KR1020177030895A patent/KR20170140232A/ko not_active IP Right Cessation
- 2016-04-21 EP EP16720757.0A patent/EP3288995B1/de active Active
- 2016-04-21 KR KR1020237036131A patent/KR20230152784A/ko active Search and Examination
- 2016-04-21 PL PL16720757.0T patent/PL3288995T3/pl unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| DE102015207792A1 (de) | 2016-11-03 |
| EP3288995B1 (de) | 2024-03-20 |
| KR20230152784A (ko) | 2023-11-03 |
| RU2017134962A3 (zh) | 2019-10-15 |
| WO2016173926A1 (de) | 2016-11-03 |
| PL3288995T3 (pl) | 2024-07-15 |
| US11365278B2 (en) | 2022-06-21 |
| BR112017023077A2 (pt) | 2018-07-10 |
| JP2018521150A (ja) | 2018-08-02 |
| JP6949722B2 (ja) | 2021-10-13 |
| US20180044462A1 (en) | 2018-02-15 |
| RU2017134962A (ru) | 2019-04-05 |
| EP3288995A1 (de) | 2018-03-07 |
| CN107709398A (zh) | 2018-02-16 |
| KR20170140232A (ko) | 2017-12-20 |
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