CN102639625B - 金属配合物作为氧气吸收剂/清除剂成分在包装应用中的用途 - Google Patents
金属配合物作为氧气吸收剂/清除剂成分在包装应用中的用途 Download PDFInfo
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- CN102639625B CN102639625B CN201080054866.0A CN201080054866A CN102639625B CN 102639625 B CN102639625 B CN 102639625B CN 201080054866 A CN201080054866 A CN 201080054866A CN 102639625 B CN102639625 B CN 102639625B
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- Prior art keywords
- oxygen
- butyl
- bis
- phenyl
- hydroxyl
- 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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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 23
- 239000002184 metal Substances 0.000 title claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 title claims description 68
- 239000001301 oxygen Substances 0.000 title claims description 63
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 55
- 238000004806 packaging method and process Methods 0.000 title abstract description 6
- 239000002516 radical scavenger Substances 0.000 title description 6
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- 239000000654 additive Substances 0.000 claims abstract description 20
- 230000000996 additive effect Effects 0.000 claims abstract description 16
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- 238000007254 oxidation reaction Methods 0.000 claims abstract description 13
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 6
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 5
- 150000003624 transition metals Chemical class 0.000 claims abstract description 5
- -1 cyclic olefin Chemical class 0.000 claims description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- 229940123973 Oxygen scavenger Drugs 0.000 claims description 13
- 150000003097 polyterpenes Chemical class 0.000 claims description 12
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 229910052748 manganese Inorganic materials 0.000 claims description 9
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- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 6
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000758 substrate Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000523 sample Substances 0.000 description 37
- 150000002148 esters Chemical class 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000010408 film Substances 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- 229960003742 phenol Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 9
- JXSRRBVHLUJJFC-UHFFFAOYSA-N 7-amino-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound N1=CC(C#N)=C(N)N2N=C(SC)N=C21 JXSRRBVHLUJJFC-UHFFFAOYSA-N 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- 239000011572 manganese Substances 0.000 description 9
- SZINCDDYCOIOJQ-UHFFFAOYSA-L manganese(2+);octadecanoate Chemical compound [Mn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SZINCDDYCOIOJQ-UHFFFAOYSA-L 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
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- 238000002156 mixing Methods 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 7
- 229910052742 iron Inorganic materials 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
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- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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Abstract
本发明涉及一种氧气清除组合物，包含(I)聚合物树脂，(II)基于螯合芳族或非芳族胺和过渡金属配合物的金属有机氧化添加剂，(III)可氧化的牺牲基材，以及任选地(IV)额外组分，还涉及含有所述氧气清除组合物的制品以及所述氧气清除组合物在食品包装中的用途。
Description
尤其在食品和药物工业中人们日益要求更好地保护其内容物的包装材料，但现在也在其它工业如农业化学品、电子和护理中也有此要求。由于塑料在这些应用中变得越来越常见，对于它们如何良好地允许气体和蒸气交换存在许多关切，这种交换可能损害产品的质量和安全性。
氧气的存在通过直接化学反应或者作为腐败细菌的促成剂而成为在当前经济中在地球上由一个地方运输到另一个地方或者长期储存的食品腐败的主要来源之一。因此，包装工业长久以来试图置换包装体内部的氧气，其中用惰性气体将其置换(气调包装，MAP)，并使用具有低透氧性的被动阻隔材料阻断氧气由该类包装体的外部进入内部。即使上面的技术各自在工业上占有一席之地，但普遍认为引入氧气清除剂作为包装制品的一部分是限制氧气的最理想方式之一。
尤其对本身为氧气的良好被动阻隔剂且尤其选择作为饮料包装材料的PET(聚对苯二甲酸乙二醇酯)觉察到该问题。已经设计出许多技术以清除能够通过该PET被动阻隔层的低浓度氧气，并且因此允许包装体内容物具有实际无氧期。该类技术通常基于添加到主聚合物中或者作为单独共挤出层/在单独共挤出层中的化合物的催化氧化，而不利用任何活化机理。它们依赖于包装材料由制造商到最终工业用户的有效转移以通过与大气氧反应而解决活性组分耗尽的问题，但结果不一致。
已经设计出相反依赖于某一活化机理的其它方案，该活化机理在清除化学品与氧气开始与包装塑料制造不同的时间点发生反应时启动。在Sealed Air所销售的体系中，例如该活化通过对包装生产线的UV辐射实现，该生产线必须加以改性以使用该体系。还存在活性和安全性关切。相反，现在由Albis(以前为Ciba Specialty Chemicals)销售的铁基化学添加剂依赖于包装物品中存在的水本身作为氧气清除过程的触发剂。然而，该水需求是很大的且足够活性所需添加剂量使甚至薄的塑料片材显著变暗。该效果是不希望的，因为消费者更喜欢能够清楚地看见他们所购买的包装体内部所含食品。
在包装体内实现或保持低氧环境的另一方法是使用含有氧气吸收材料的小包。有时也称为盒或小袋的小包与产品一起置于包装体内部。Sakamoto等在日本专利申请公开号121634/81(1981)中公开了氧气吸收小包。
尽管用于小包中的氧气吸收剂或清除剂材料如还原性铁粉、氯化钠电解质体系和吸水剂如硅胶可以与该包装体中的氧气(顶空氧气)发生化学反应，但它们不能防止外部氧气渗入包装体中。因此，对于这类包装而言通常引入额外的保护如包封或被动阻隔膜(乙烯/乙烯醇共聚物EVOH，聚偏二氯乙烯PVDC等)，这不可避免地增加了产品成本。此外，对于许多易于制备的食品，氧气清除剂小包的另一困难在于消费者可能错误地打开它们并与该食品一起用完其内容物。此外，将小包放入容器中的额外制造步骤可能增加产品趁本并减缓生产。此外，氧气吸收小包不能用于液体产品。
因此，当前可得体系中没有一种具有对于新鲜或配制食品的包装满足苛刻市场要求的所有特性。
本发明解决了一些限制该有用技术的利用的问题。
因此，本发明的目的是提供改进的氧气清除组合物和包装材料。另一目的是提供具有改进效率的低成本氧气清除组合物。另一目的是提供甚至可以在相对低水平下有效用于宽范围的主动阻隔包装薄膜和片材(包括层压的和共挤出的多层薄膜和片材)中的氧气清除组合物。另一目的是提供可以通过减缓外部氧气进入容器中、通过吸收存在于容器内的氧气或通过这二者而提高氧气敏感性产品的贮存期限的主动阻隔包装容器。其它目的对本领域熟练技术人员将是明显的。
已经观察到使用本发明的氧气清除组合物提高了包装食品对氧气破坏的耐受性。
因此，本发明涉及一种用于食品包装应用的氧气清除剂组合物，其包含如下组分：
(I)聚合物树脂，优选热塑性聚合物
烯烃单体如乙烯和丙烯以及还有高级1-烯烃如1-丁烯、1-戊烯、1-己烯或1-辛烯的均聚物和共聚物。优选聚乙烯LDPE和LLDPE、HDPE以及聚丙烯；
烯烃单体与二烯烃单体如丁二烯、异戊二烯和环烯烃如降冰片烯的均聚物和共聚物；
一种或多种1-烯烃和/或二烯烃与一氧化碳和/或其它乙烯基单体的共聚物，所述乙烯基单体包括但不限于丙烯酸及其对应丙烯酸酯、甲基丙烯酸及其对应酯、乙酸乙烯酯、乙烯醇、乙烯基酮、苯乙烯、马来酸酐和氯乙烯；
聚乙烯醇；
(II)基于螯合芳族或非芳族胺和过渡金属配合物的金属有机氧化添加剂如下述实例所定义。这些有机金属氧化添加剂配合物通常基于Co、Ce、Mn、Cu、Ni、Vd、Fe、Ti。优选这些氮配体氧化添加剂为具有C12-C36碳数的脂肪酸的金属盐。最优选棕榈酸(C16)、硬脂酸(C18)、油酸(C18)、亚油酸(C18)和亚麻酸(C18)的金属羧酸盐。优选过渡金属盐为锰、铜、铁或钴，最优选锰或铜，其基于聚合物树脂可以以0.001-10重量%，优选0.01-5重量%，最优选0.1-5重量%的总浓度存在。还可能的是丙酸(C3)、乙酸(C2)、甲酸(C1)或苯甲酸的金属盐。还可能的是金属配合物中的抗衡离子为卤素，优选但不限于氯、溴和碘。氧化添加剂基于聚合物树脂可以以0.001-10重量%，优选0.01-5重量%，最优选0.1-5重量%的总浓度存在；
(III)可氧化的牺牲基材，如聚丁二烯、聚酯、角鲨烷、角鲨烯、聚苯乙烯、聚苎烯、聚α-蒎烯、聚β-蒎烯、聚降冰片烯、聚乳酸、线性和支化烷基链醇(R：C6-C30)的混合物。优选这些可氧化基材基于聚合物树脂以0.001-10重量%，优选0.01-5重量%，最优选0.1-5重量%的总浓度存在；以及任选地
(IV)额外组分。
本发明的金属有机氧化催化剂涉及下式的金属配合物：
[LnMemXp]zYq
其中
Me为锰、铜、钴、镍、铁、铈、钒或钛，
X为配位或桥接基团，
n和m各自独立地为1-8的整数，
p为0-32的整数，
z为该金属配合物的电荷，
Y为抗衡离子，
q=z(电荷Y)，以及
L为式
的配体，
其中
R1、R2、R3、R4、R5、R6、R7、R8和R9各自独立地为氢，未取代或取代的C1-C18烷基或芳基，氰基、卤素，硝基，-COOR10或-SO3R10，其中R10在每种情况下为氢、阳离子或未取代或取代的C1-C18烷基或芳基，-SR11、-SO2R11或-OR11，其中R11在每种情况下为氢或未取代或取代的C1-C18烷基或芳基，-N(R11)-NR’11R”11，其中R11、R’11和R”11如对R11所定义，-NR12R13或-N+R12R13R14，其中R12、R13和R14各自独立地为氢或未取代或取代的C1-C18烷基或芳基，或者R12和R13与它们所键合的氮原子一起形成未取代或取代的可以任选含有其它杂原子的5、6或7员环；
并且其中G为苯基或萘基，其未被取代或被C1-C6烷基、C1-C6烷氧基、卤素、氰基、硝基、羧基、磺基、羟基、氨基、未取代或在烷基结构部分中被羟基取代的N-单-或N,N-二-C1-C6烷基氨基、N-苯基氨基、N-萘基氨基、苯基、苯氧基或萘氧基取代。优选的取代基是吡啶基、咪唑或哌啶基。
特别优选下表所给化合物：
对于上面所引用实例的氧化添加剂特别优选的原料是市售化合物，例如
硬脂酸锰
硬脂酸铜
氯化锰
2,2'-联吡啶
1，10-菲咯啉
4'-对甲苯基-2,2':6',2″-三联吡啶
4,4'-二壬基-2,2'-联吡啶
聚α-蒎烯
聚β-蒎烯
聚苎烯
任选的额外组分包括：
-填料和增强剂，如碳酸钙、硅石、玻璃纤维、玻璃球、滑石、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、碳黑、石墨、木粉、其它天然产品的粉、合成纤维、用作填料的硬脂酸盐如硬脂酸钙或硬脂酸锌；
-颜料如碳黑、呈其金红石或锐钛矿形式的二氧化钛以及其它彩色颜料；
-光稳定剂、抗氧化剂和/或其它光稳定剂，例如：
1.烷基化单酚，例如2,6-二叔丁基-4-甲基苯酚，2-叔丁基-4,6-二甲基苯酚，2,6-二叔丁基-4-乙基苯酚，2,6-二叔丁基-4-正丁基苯酚，2,6-二叔丁基-4-异丁基苯酚，2,6-二环戊基-4-甲基苯酚，2-(α-甲基环己基)-4,6-二甲基苯酚，2,6-二-十八烷基-4-甲基苯酚，2,4,6-三环己基苯酚，2,6-二叔丁基-4-甲氧基甲基苯酚，侧链为线性或支化的壬基酚类，例如2,6-二壬基-4-甲基苯酚，2,4-二甲基-6-(1'-甲基十一烷-1'-基)苯酚，2,4-二甲基-6-(1'-甲基十七烷-1'-基)苯酚，2,4-二甲基-6-(1'-甲基十三烷-1'-基)苯酚及其混合物。
2.烷硫基甲基酚类，例如2,4-二辛硫基甲基-6-叔丁基苯酚，2,4-二辛硫基甲基-6-甲基苯酚，2,4-二辛硫基甲基-6-乙基苯酚，2,6-二-十二烷硫基甲基-4-壬基苯酚。
3.氢醌类和烷基化氢醌类，例如2,6-二叔丁基-4-甲氧基苯酚，2,5-二叔丁基氢醌，2,5-二叔戊基氢醌，2,6-二苯基-4-十八烷氧基苯酚，2,6-二叔丁基氢醌，2,5-二叔丁基-4-羟基茴香醚，3,5-二叔丁基-4-羟基茴香醚，硬脂酸3,5-二叔丁基-4-羟基苯基酯，己二酸二(3,5-二叔丁基-4-羟基苯基)酯。
4.生育酚类，例如α-生育酚，β-生育酚，γ-生育酚，δ-生育酚及其混合物(维生素E)。
5.羟基化硫代二苯醚，例如2,2'-硫代二(6-叔丁基-4-甲基苯酚)，2,2'-硫代二(4-辛基苯酚)，4,4'-硫代二(6-叔丁基-3-甲基苯酚)，4,4'-硫代二(6-叔丁基-2-甲基苯酚)，4,4'-硫代二(3,6-二仲戊基苯酚)，4,4'-二(2,6-二甲基-4-羟基苯基)二硫化物。
6.亚烷基双酚类，例如2,2'-亚甲基二(6-叔丁基-4-甲基苯酚)，2,2'-亚甲基二(6-叔丁基-4-乙基苯酚)，2,2'-亚甲基二[4-甲基-6-(α-甲基环己基)苯酚]，2,2'-亚甲基二(4-甲基-6-环己基苯酚)，2,2'-亚甲基二(6-壬基-4-甲基苯酚)，2,2'-亚甲基二(4,6-二叔丁基苯酚)，2,2'-亚乙基二(4,6-二叔丁基苯酚)，2,2'-亚乙基二(6-叔丁基-4-异丁基苯酚)，2,2'-亚甲基二[6-(α-甲基苄基)-4-壬基苯酚]，2,2'-亚甲基二[6-(α,α-二甲基苄基)-4-壬基苯酚]，4,4'-亚甲基二(2,6-二叔丁基苯酚)，4,4'-亚甲基二(6-叔丁基-2-甲基苯酚)，1,1-二(5-叔丁基-4-羟基-2-甲基苯基)丁烷，2,6-二(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚，1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷，1,1-二(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷硫基丁烷，乙二醇二[3,3-二(3'-叔丁基-4'-羟基苯基)丁酸酯]，二(3-叔丁基-4-羟基-5-甲基苯基)二聚环戊二烯，对苯二甲酸二[2-(3'-叔丁基-2'-羟基-5'-甲基苄基)-6-叔丁基-4-甲基苯基]酯，1,1-二(3,5-二甲基-2-羟基苯基)丁烷，2,2-二(3,5-二叔丁基-4-羟基苯基)丙烷，2,2-二(5-叔丁基-4-羟基2-甲基苯基)-4-正十二烷硫基丁烷，1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
7.O-、N-和S-苄基化合物，例如3,5,3',5'-四叔丁基-4,4'-二羟基二苄基醚，4-羟基-3,5-二甲基苄基巯基乙酸十八烷基酯，4-羟基-3,5-二叔丁基苄基巯基乙酸十三烷基酯，三(3,5-二叔丁基-4-羟基苄基)胺、二硫代对苯二甲酸二(4-叔丁基-3-羟基-2,6-二甲基苄基)酯，二(3,5-二叔丁基-4-羟基苄基)硫化物，3,5-二叔丁基-4-羟基苄基巯基乙酸异辛基酯。
8.羟苄基化丙二酸酯类，例如2,2-二(3,5-二叔丁基-2-羟基苄基)丙二酸二-十八烷基酯，2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸二-十八烷基酯，2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸二-十二烷硫基乙基酯，2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸二[4-(1,1,3,3-四甲基丁基)苯基]酯。
9.芳族羟苄基化合物，例如1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯，1,4-二(3,5-二叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯，2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯酚。
10.三嗪化合物，例如2,4-二(辛硫基)-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪，2-辛硫基-4,6-二(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪，2-辛硫基-4,6-二(3,5-二叔丁基-4-羟基苯氧基)-1,3,5-三嗪，2,4,6-三(3,5-二叔丁基-4-羟基苯氧基)-1,2,3-三嗪，异氰脲酸1,3,5-三(3,5-二叔丁基-4-羟基苄基)酯，异氰脲酸1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)酯，2,4,6-三(3,5-二叔丁基-4-羟基苯基乙基)-1,3,5-三嗪，1,3,5-三(3,5-二叔丁基-4-羟基苯基丙酰基)-六氢-1,3,5-三嗪，异氰脲酸1,3,5-三(3,5-二环己基-4-羟基苄基)酯。
11.苄基膦酸酯，例如2,5-二叔丁基-4-羟基苄基膦酸二甲酯，3,5-二叔丁基-4-羟基苄基膦酸二乙酯，3,5-二叔丁基-4-羟基苄基膦酸二-十八烷基酯，5-叔丁基-4-羟基-3-甲基苄基膦酸二-十八烷基酯，3,5-二叔丁基-4-羟基苄基膦酸单乙酯的钙盐。
12.酰氨基酚类，例如4-羟基月桂酰替苯胺，4-羟基硬脂酰替苯胺，N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
13.β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元醇或多元醇的酯，例如与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟乙基)酯、N,N'-二(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯。
14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇的酯，例如与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟乙基)酯、N,N'-二(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷、3,9-二[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}-1,1-二甲基乙基]-2,4,8,10-四氧杂螺[5.5]十一烷的酯。
15.β-(3,5-二环己基-4-羟基苯基)丙酸与一元醇或多元醇的酯，例如与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟乙基)酯、N,N'-二(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯。
16.3,5-二叔丁基-4-羟基苯基乙酸与一元醇或多元醇的酯，例如与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟乙基)酯、N,N'-二(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯。
17.β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺，例如N,N'-二(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二胺，N,N'-二(3,5-二叔丁基-4-羟基苯基丙酰基)三亚甲基二胺，N,N'-二(3,5-二叔丁基-4-羟基苯基丙酰基)肼，N,N'-双[2-(3-[3,5-二叔丁基-4-羟基苯基]丙酰氧基)乙基]草酰胺(N
XL-1，由Uniroyal提供)。
18.抗坏血酸(维生素C)
19.胺类抗氧化剂，例如N,N'-二异丙基对苯二胺，N,N'-二仲丁基对苯二胺，N,N'-二(1,4-二甲基戊基)对苯二胺，N,N'-二(1-乙基-3-甲基戊基)对苯二胺，N,N'-二(1-甲基庚基)对苯二胺，N,N'-二环己基对苯二胺，N,N'-二苯基对苯二胺，N,N'-二(2-萘基)对苯二胺，N-异丙基-N'-苯基对苯二胺，N-(1,3-二甲基丁基)-N'-苯基对苯二胺，N-(1-甲基庚基)-N'-苯基对苯二胺，N-环己基-N'-苯基对苯二胺，4-(对甲苯氨磺酰基)二苯基胺，N,N'-二甲基-N,N'-二仲丁基对苯二胺，二苯基胺，N-烯丙基二苯基胺，4-异丙氧基二苯基胺，N-苯基-1-萘基胺，N-(4-叔辛基苯基)-1-萘基胺，N-苯基-2-萘基胺，辛基化二苯基胺，例如4,4'-二叔辛基二苯基胺，4-正丁基氨基苯酚，4-丁酰氨基苯酚，4-壬酰氨基苯酚，4-十二烷酰氨基苯酚，4-十八烷酰氨基苯酚，二(4-甲氧基苯基)胺，2,6-二叔丁基-4-二甲氨基甲基苯酚，2,4'-二氨基二苯基甲烷，4,4'-二氨基二苯基甲烷，N,N,N',N'-四甲基-4,4'-二氨基二苯基甲烷，1,2-二[(2-甲基苯基)氨基]乙烷，1,2-二(苯基氨基)丙烷，邻甲苯基双胍，二[4-(1',3'-二甲基丁基)苯基]胺，叔辛基化N-苯基-1-萘基胺，单-和二烷基化叔丁基/叔辛基二苯基胺的混合物，单-和二烷基化壬基二苯基胺的混合物，单-和二烷基化十二烷基二苯基胺的混合物，单-和二烷基化异丙基/异己基二苯基胺的混合物，单-和二烷基化叔丁基二苯基胺的混合物，2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪，吩噻嗪，单-和二烷基化叔丁基/叔辛基吩噻嗪的混合物，单-和二烷基化叔辛基吩噻嗪的混合物，N-烯丙基吩噻嗪、N,N,N',N'-四苯基-1,4-二氨基丁-2-烯。
20.2-(2'-羟基苯基)苯并三唑类，例如2-(2'-羟基-5'-甲基苯基)苯并三唑，2-(3',5'-二叔丁基-2'-羟基苯基)苯并三唑，2-(5'-叔丁基-2'-羟基苯基)苯并三唑，2-(2'-羟基-5'-(1,1,3,3-四甲基丁基)苯基)苯并三唑，2-(3',5'-二叔丁基-2'-羟基苯基)-5-氯苯并三唑，2-(3'-叔丁基-2'-羟基-5'-甲基苯基)-5-氯苯并三唑，2-(3'-仲丁基-5'-叔丁基-2'-羟基苯基)苯并三唑，2-(2'-羟基-4'-辛氧基苯基)苯并三唑，2-(3',5'-二叔戊基-2'-羟基苯基)苯并三唑，2-(3',5'-二(α,α-二甲基苄基)-2'-羟基苯基)苯并三唑，2-(3'-叔丁基-2'-羟基-5'-(2-辛氧羰基乙基)苯基)-5-氯苯并三唑，2-(3'-叔丁基-5'-[2-(2-乙基己氧基)羰基乙基]-2'-羟基苯基)-5-氯苯并三唑，2-(3'-叔丁基-2'-羟基-5'-(2-甲氧羰基乙基)苯基)-5-氯苯并三唑，2-(3'-叔丁基-2'-羟基-5'-(2-甲氧羰基乙基)苯基)苯并三唑，2-(3'-叔丁基-2'-羟基-5'-(2-辛氧羰基乙基)苯基)苯并三唑，2-(3'-叔丁基-5'-[2-(2-乙基己氧基)羰基乙基]-2'-羟基苯基)苯并三唑，2-(3'-十二烷基-2'-羟基-5'-甲基苯基)苯并三唑，2-(3'-叔丁基-2'-羟基-5'-(2-异辛氧羰基乙基)苯基苯并三唑，2,2'-亚甲基二[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚]；2-[3'-叔丁基-5'-(2-甲氧羰基乙基)-2'-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物；
其中R=3'-叔丁基-4'-羟基-5'-2H-苯并三唑-2-基苯基，2-[2'-羟基-3'-(α,α-二甲基苄基)-5'-(1,1,3,3-四甲基丁基)苯基]苯并三唑；2-[2'-羟基-3'-(1,1,3,3-四甲基丁基)-5'-(α,α-二甲基苄基)苯基]苯并三唑。
21.2-羟基二苯甲酮类，例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2',4'-三羟基和2'-羟基-4,4'-二甲氧基衍生物。
22.取代和未取代苯甲酸的酯，例如水杨酸4-叔丁基苯酯，水杨酸苯酯，水杨酸辛基苯酯，二苯甲酰间苯二酚，二(4-叔丁基苯甲酰)间苯二酚，苯甲酰间苯二酚，3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯酯，3,5-二叔丁基-4-羟基苯甲酸十六烷基酯，3,5-二叔丁基-4-羟基苯甲酸十八烷基酯，3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯酯。
23.丙烯酸酯类，例如α-氰基-β,β-二苯基丙烯酸乙酯，α-氰基-β,β-二苯基丙烯酸异辛酯，α-甲酯基肉桂酸甲酯，α-氰基-β-甲基对甲氧基肉桂酸甲酯，α-氰基-β-甲基对甲氧基肉桂酸丁酯，α-甲酯基对甲氧基肉桂酸甲酯，N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚，四(α-氰基-β,β-二苯基丙烯酸)新戊基酯。
24.位阻胺类，例如碳酸二(1-十一烷氧基-2,2,6,6-四甲基-4-哌啶基)酯，癸二酸二(2,2,6,6-四甲基-4-哌啶基)酯，琥珀酸二(2,2,6,6-四甲基-4-哌啶基)酯，癸二酸二(1,2,2,6,6-五甲基-4-哌啶基)酯，癸二酸二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)酯，正丁基-3,5-二叔丁基-4-羟基苄基丙二酸二(1,2,2,6,6-五甲基-4-哌啶基)酯，1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物，N,N'-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的线性或环状缩合物，次氮基三乙酸三(2,2,6,6-四甲基-4-哌啶基)酯，1,2,3,4-丁烷四甲酸四(2,2,6,6-四甲基-4-哌啶基)酯，1,1'-(1,2-亚乙基)-二(3,3,5,5-四甲基哌嗪酮)，4-苯甲酰基-2,2,6,6-四甲基哌啶，4-硬脂氧基-2,2,6,6-四甲基哌啶，2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸二(1,2,2,6,6-五甲基哌啶基)酯，3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮，癸二酸二(1-辛氧基-2,2,6,6-四甲基哌啶基)酯，琥珀酸二(1-辛氧基-2,2,6,6-四甲基哌啶基)酯，N,N'-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉基-2,6-二氯-1,3,5-三嗪的线性或环状缩合物，2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物，2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物，8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮，3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷酮-2,5-二酮，3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷酮-2,5-二酮，4-十六烷氧基-和4-硬脂氧基-2,2,6,6-四甲基哌啶的混合物，N,N'-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合物，1,2-二(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪以及4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[136504-96-6])，1,6-己二胺和2,4,6-三氯-1,3,5-三嗪以及N,N-二丁基胺和4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[192268-64-7])，N-(2,2,6,6-四甲基-4-哌啶基)正十二烷基琥珀酰亚胺，N-(1，2,2,6,6-五甲基-4-哌啶基)正十二烷基琥珀酰亚胺，2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷，7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷和表氯醇的反应产物，1,1-二(1,2,2,6,6-五甲基-4-哌啶基氧羰基)-2-(4-甲氧基苯基)乙烯，N,N'-二甲酰基-N,N'-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺，4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯，聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷，马来酸酐-α-烯烃共聚物与2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物，2,4-二[N-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)-N-丁基氨基]-6-(2-羟基乙基)氨基-1,3,5-三嗪，1-(2-羟基-2-甲基丙氧基)-4-十八烷酰氧基-2,2,6,6-四甲基哌啶，5-(2-乙基己酰基)氧基甲基-3,3,5-三甲基-2-吗啉酮，Sanduvor(Clariant；CAS登记号106917-31-1]，5-(2-乙基己酰基)氧基甲基-3,3,5-三甲基-2-吗啉酮，2,4-二[(1-环己氧基-2,2,6,6-哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)乙二胺)的反应产物，1,3,5-三(N-环己基-N-(2,2,6,6-四甲基哌嗪-3-酮-4-基)氨基)-s-三嗪，1,3,5-三(N-环己基-N-(1，2,2,6,6-五甲基哌嗪-3-酮-4-基)氨基)-s-三嗪。
25.草酰胺类，例如4,4'-二辛氧基草酰替苯胺，2,2'-二乙氧基草酰替苯胺，2,2'-二辛氧基-5,5'-二叔丁基草酰替苯胺，2,2'-二(十二烷氧基)-5,5'-二叔丁基草酰替苯胺，2-乙氧基-2'-乙基草酰替苯胺，N,N'-双(3-二甲基氨基丙基)草酰胺，2-乙氧基-5-叔丁基-2'-乙基草酰替苯胺及其与2-乙氧基-2'-乙基-5,4'-二叔丁基草酰替苯胺的混合物，邻-和对-甲氧基二取代草酰替苯胺的混合物以及邻-和对-乙氧基二取代草酰替苯胺的混合物。
26.2-(2-羟基苯基)-1,3,5-三嗪类，例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪，2-(2-羟基-4-辛氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪，2-(2,4-二羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪，2,4-二(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪，2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪，2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪，2-(2-羟基-4-十三烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪，2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-二(2,4-二甲基)-1,3,5-三嗪，2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-二(2,4-二甲基)-1,3,5-三嗪，2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪，2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪，2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪，2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪，2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪，2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪，2-{2-羟基-4-[3-(2-乙基己基-1-氧基)-2-羟基丙氧基]苯基}-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪，2,4-二(4-[2-乙基己氧基]-2-羟基苯基)-6-(4-甲氧基苯基)-1,3,5-三嗪。
-加工添加剂如防滑/抗结块添加剂、增塑剂、荧光增白剂、抗静电剂和发泡剂；
抗氧化剂可以以在加工和成型步骤中稳定所述聚合物的量存在，但其目的不是为了防止降解的大量不合乎需要。
本发明可以用于所有希望具有氧气清除剂活性的包装领域中。
最终产品可以是用于食品包装应用的任何类型塑料产品，其需要提高的氧气清除剂活性。
例如，该聚合物组分可以用于制造单层或多层塑料薄膜、片材、层压材料、袋子、瓶子、聚苯乙烯泡沫杯、器皿、泡罩包装、盒子、包装垫料。所述制品可以通过本领域普通技术人员可得的任何方法制造，这些方法包括但不限于挤出、挤坯吹塑、薄膜流延、簿膜吹塑、压延、注塑、吹塑、压塑成型、热成型、纺丝、吹胀挤出和旋转流延。具体而言，在气调(CO2，N2)食品包装领域中这是令人感兴趣的。氧气吸收速率可以通过改变添加剂浓度而简单调节，即若希望氧气清除剂性能越高，则加入的添加剂量越高。
金属有机氧化添加剂、可氧化的牺牲基材以及任选地其它额外组分可以同时或依次与聚合物树脂混合，或者也可以直接在实际加工步骤之前混合。
因此，本发明进一步涉及一种由含有如上所定义的聚合物树脂、如上所定义的基于螯合芳族或非芳族胺和过渡金属配合物的金属有机氧化添加剂、如上所定义的可氧化的牺牲基材以及任选地如上所定义的额外组分的组合物制成或包含该组合物的制品。
所引用实例的合成最好如下列实施例所述进行。
掺入各种添加剂最好在热配混步骤中进行，将氧化添加剂和任选的添加剂彻底混合，然后在升高的温度下挤出物理共混物。通常将具有合适螺杆构造的挤出机用于该步骤。添加剂也可以以由不同方式生产的预调制母料形式加入。为了生产所需制品，可以使用任何合适的机器，这取决于制品的最终形式，例如在薄膜情况下使用吹胀挤出机，在片材情况下使用流延挤出机或使用注塑机。
下列实施例更详细说明本发明。除非另有指明，所有百分数和份数按重量计且所有反应在氮气下进行。
Riblene
低密度聚乙烯得自Polimeri Europa；
为由Les Dérivés Résiniques&Terpéniques得到的聚萜烯产品；硬脂酸锰Mn(C18H35O2)x购自Shepherd Chemical；硬脂酸铜Cu(C18H35O2)x购自H.L.Blachford Ltd.且Shelfplus O2 得自ALBIS Chemicals。
实施例1：合成1,10-菲咯啉/硬脂酸铜金属配合物
在70°C下将20.0g硬脂酸铜悬浮于300ml MeOH中。向该溶液中加入7.6g 1,10-菲咯啉并将该反应在回流下加热2小时。将该溶液在室温下冷却并将产物由冷MeOH沉淀、过滤并真空干燥而得到12.2g配合物(1)(收率：47.6%)。
熔点：180-193°C。
元素分析：实测值：C：70.71%；H：9.62%；N：3.47%。理论值：C：71.11%；H：9.70%；N：3.46%。ICP铜：7.75%。
实施例2：合成1,10-菲咯啉/硬脂酸锰金属配合物
在70°C下将20.0g硬脂酸锰溶于1.5L丁醇中。向该溶液中加入5.8g1,10-菲咯啉并将该反应在回流下加热2小时。当在室温下冷却该溶液时产物沉淀，将其过滤、用冷MeOH洗涤并真空干燥而得到15.6g配合物(2)(收率：60.5%)。
熔点：120-123°C。
元素分析：实测值：C：70.35%；H：9.93%；N：3.49%。理论值：C：71.88%；H：9.80%；N：3.49%。ICP锰：6.65%。
实施例3：联吡啶/硬脂酸锰金属配合物
在70°C下将20.0g硬脂酸锰溶于150ml DMA中。向该溶液中加入5.0g2,2’-联吡啶并将该反应搅拌4小时。产物用水沉淀、过滤并真空干燥而得到14.4g配合物(3)(收率：57.6%)。
熔点：185-189°C。
元素分析：实测值：C：69.10%；H：10.29%；N：3.52%。理论值：C：71.01%；H：10.10%；N：3.60%。ICP锰：7.17%。
实施例4：联吡啶/硬脂酸铜金属配合物
在回流下将20.0g硬脂酸铜溶于1000ml MeOH中。向该溶液中加入5.8g 2,2’-联吡啶并将该反应搅拌6小时。将由冷溶液沉淀的产物过滤并真空干燥而得到20.1g配合物(4)(收率：80.1%)。
熔点：152-154°C
元素分析：实测值：C：69.45%；H：9.99%；N：3.60%。理论值：C：70.23%；H：9.99%；N：3.56%。ICP铜：8.02%。
实施例5：联吡啶/氯化锰金属配合物
在60°C下将12.1g MnCl2溶于100ml EtOH中。向该溶液中加入15.0g2,2’-联吡啶并将该反应搅拌3小时。滤出沉淀、用EtOH洗涤并真空干燥而得到25.9g配合物5(收率：95.9%)。
熔点：>300°C。
元素分析：实测值：C：43.02%；H：2.91%；Cl：25.19%；N：10.02%。
理论值：C：42.59%；H：2.86%；Cl：25.14%；N：9.93%。ICP锰：19.56%。
实施例6：4,4'-二壬基-2,2'-联吡啶/氯化锰金属配合物
在60°C下将3.1g MnCl2溶于25ml EtOH中。向该溶液中加入10.0g4,4'-二壬基-2,2'-联吡啶并将该反应搅拌2小时。除去溶剂并由乙醚沉淀产物，得到11.2g配合物(6)(收率：85.7%)。
熔点：270-274°C
元素分析：实测值：C：62.66%；H：8.21%；Cl：13.12%；N：5.16%。
理论值：C：62.92%；H：8.30%；Cl：13.27%；N：5.24%。ICP锰：11.12%。
实施例7：4'-对甲苯基-2,2':6',2″-三联吡啶/硬脂酸锰金属配合物
在70°C下将3.0g硬脂酸锰悬浮于30ml丁醇中。向该溶液中加入3.1g4'-对甲苯基-2,2':6',2″-三联吡啶并将该反应在回流下搅拌2小时。除去溶剂并将产物由丙酮沉淀、过滤和真空干燥而得到1.6g配合物(7)(收率：35.8%)。
熔点：161-167°C
元素分析：实测值：C：72.38%；H：8.81%；N：4.49%。理论值：C：73.70%；H：9.28%；N：4.45%。ICP锰：5.91%
实施例8：4'-对甲苯基-2,2':6',2″-三联吡啶/硬脂酸铜金属配合物
在70°C下将7.7g硬脂酸铜悬浮于100ml MeOH中。向该溶液中加入4.0g 4'-对甲苯基-2,2':6',2″-三联吡啶并将该反应在回流下搅拌2小时。产物用水沉淀、过滤、用丙酮洗涤并真空干燥而得到11.2g配合物(8)(收率：95.6%)。
熔点：143-148°C
元素分析：实测值：C：71.63%；H：9.24%；N：4.14%。理论值：C：73.03%；H：9.19%；N：4.41%。ICP铜：6.28%。
对比样品1：
将Shelfplus O2
以1:1的比例与低密度聚乙烯
混合，从而使最终铁浓度为5.0重量%。使用OMC试验双螺杆挤出机(EBV 19/25型，具有19mm螺杆直径和1:25的比例)制备配混物，并使用30×25L/D型Collin流延扁平口模挤出机(30mm螺杆直径，1:25直径/长度比)制备50微米厚的薄膜。
对比样品2：
将2.0%聚萜烯树脂
S125和0.35%硬脂酸锰与低密度聚乙烯
混合。如对比样品1中所述制备配混物和薄膜。
对比样品3：
将2.0%聚萜烯树脂
S125和0.35%硬脂酸铜与低密度聚乙烯
混合。如对比样品1中所述制备配混物和薄膜。
对比样品4：
将2.0%聚萜烯树脂
S125与低密度聚乙烯
混合。如对比样品1所述制备配混物和薄膜。
发明样品5：
将2.0%聚萜烯树脂
S125和0.35%实施例1的配混料与低密度聚乙烯
混合。如对比样品1所述制备配混物和薄膜。
发明样品6：
将2.0%聚萜烯树脂
S125和0.35%实施例2的配混料与低密度聚乙烯
混合。如对比样品1所述制备配混物和薄膜。
发明样品7：
将2.0%聚萜烯树脂
S125和0.35%实施例3的配混料与低密度聚乙烯
混合。如对比样品1所述制备配混物和薄膜。
发明样品8：
将2.0%聚萜烯树脂S125和0.35%实施例4的配混料与低密度聚乙烯Riblene混合。如对比样品1所述制备配混物和薄膜。
发明样品9：
将2.0%聚萜烯树脂
S125和0.35%实施例5的配混料与低密度聚乙烯
混合。如对比样品1所述制备配混物和薄膜。
发明样品10：
将2.0%聚萜烯树脂
S125和0.35%实施例6的配混料与低密度聚乙烯
混合。如对比样品1所述制备配混物和薄膜。
发明样品11:
将2.0%聚萜烯树脂
S125和0.35%实施例7的配混料与低密度聚乙烯
混合。如对比样品1所述制备配混物和薄膜。
然后对各样品将几等份的薄膜在500ml密封烧瓶中暴露于空气(20.7%O2)中，该烧瓶配备有允许使用注射器在几个时间间隔下取出部分内部气氛以进行分析的隔膜。氧气浓度测量使用Mocon Pac Check 450液面上分析仪在28天内进行。实施例1-7、对比样品1-4和发明样品5、7、8、9、10中的实际金属浓度(铁、铜、锰)通过ICP-OES(电感耦合等离子体-发射光谱仪，Perkin Elmer Optima系列4200DV)测量。结果以ml O2/g活性清除剂给于表1中。
28天后对六种不同LDPE薄膜测量的平均氧气清除剂活性(ml O2/g清除剂)。在对比样品1的情况下：活性清除剂的g=薄膜中铁的g；在所有其它情况下：活性清除剂的g=Dercolyte的g+金属配合物的g。
表1：
| 28天后吸收的ml O2/g清除剂 | |
| 对比样品1 | 44 |
| 对比样品2 | 73 |
| 对比样品3 | 无可检测的O2吸收 |
| 对比样品4 | 无可检测的O2吸收 |
| 发明样品5 | 75 |
| 发明样品7 | 137 |
| 发明样品8 | 92 |
| 发明样品9 | 113 |
| 发明样品10 | 110 |
表1清楚地表明发明样品7-10的氧气清除剂反应性大于对比样品1-4的氧气清除剂活性。
测试样品所吸收的氧气量由密封玻璃容器的顶空中氧气浓度的变化测定。测试容器具有的顶空体积为约500ml且含有大气氧以使约100ml氧气可以用于反应。在所有实施例中，氧气清除剂组分百分数为基于该薄膜组合物总重量的重量百分数。
氧气吸收方法的详细描述：
测定薄膜厚度并称量4.0g薄膜。将挤出薄膜折叠并置于洁净的500ml密封玻璃容器中。加入含有15ml去离子水的小瓶以在所述玻璃容器内部产生100%相对湿度(仅针对对比试样1)。
使用Mocon氧气分析仪测试并记录0天时环境空气中的氧气含量(即等于密封玻璃容器中的初始氧气含量)。
将具有测试薄膜和小水瓶的玻璃容器在22°C(通常为室温)下储存28天。
使用Mocon氧气分析仪测试并记录28天时密封玻璃容器中的氧气含量。
基于测得的残留于密封玻璃容器中的氧气浓度，使用如下公式计算每克清除剂所吸收的氧气体积：
吸收的氧气(ml/g)={(%O2)i-(%O2)f}*0.01*Vj/(WF*WS/WB)
其中：
(%O2)i 密封玻璃容器中的初始氧气浓度(%)
(%O2)f 测试当天密封玻璃容器中的氧气浓度(%)
0.01：转化系数
Vj：密封玻璃容器的自由空气体积(ml)(密封玻璃容器的总体积减去小瓶和薄膜占据的空间，通常为440ml)
WF：置于玻璃容器中的薄膜重量(通常为4.0g)
WS：用于制备共混物的氧气清除剂重量(g)
WB：共混物的总重量(g)
Claims (12)
1.一种用于食品包装应用的氧气清除剂组合物，其包含如下组分：
(I)聚合物树脂，
(II)基于螯合芳族胺和过渡金属配合物的金属有机氧化添加剂，
(III)可氧化的牺牲基材，以及任选地
(IV)额外组分。
2.根据权利要求1的氧气清除组合物，其中所述聚合物树脂为选自烯烃单体的均聚物和共聚物，烯烃单体与二烯烃单体、环状烯烃的均聚物和共聚物，一种或多种1-烯烃和/或二烯烃与一氧化碳和/或其它乙烯基单体的共聚物以及聚乙烯醇的热塑性聚合物。
3.根据权利要求1的氧气清除组合物，其中所述基于螯合芳族胺和过渡金属配合物的金属有机氧化添加剂包含Co、Ce、Mn、Cu、Ni、Vd、Fe和/或Ti。
4.根据权利要求1的氧气清除组合物，其中所述可氧化的牺牲基材选自聚丁二烯、聚酯、角鲨烷、角鲨烯、聚苯乙烯、聚苎烯，聚α-蒎烯、聚β-蒎烯、聚降冰片烯、聚乳酸以及线性和支化烷基链C6-C30醇的混合物。
5.根据权利要求1的氧气清除组合物，其中所述氧气清除组合物进一步包含一种或多种选自填料、增强剂、颜料、光稳定剂、抗氧化剂、防滑和抗结块添加剂、增塑剂、荧光增白剂、抗静电剂和发泡剂的额外组分。
6.根据权利要求1的氧气清除组合物，条件是组分(I)和(III)不同。
7.根据权利要求1的氧气清除组合物，其中组分(III)为聚萜烯树脂。
8.一种包含如权利要求1-7中任一项所定义的组合物的制品。
9.根据权利要求8的制品，其为薄膜、片材或层压材料。
10.根据权利要求9的制品，其为共挤出多层薄膜。
11.根据权利要求9的制品，其为食品包装材料。
12.如权利要求1所定义的氧气清除剂组合物在食品包装中的用途。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09177741 | 2009-12-02 | ||
| EP09177741.7 | 2009-12-02 | ||
| PCT/EP2010/068374 WO2011067198A1 (en) | 2009-12-02 | 2010-11-29 | Use of metal complexes as oxygen absorber/scavenger elements for packaging applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102639625A CN102639625A (zh) | 2012-08-15 |
| CN102639625B true CN102639625B (zh) | 2014-03-19 |
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| CN201080054866.0A Expired - Fee Related CN102639625B (zh) | 2009-12-02 | 2010-11-29 | 金属配合物作为氧气吸收剂/清除剂成分在包装应用中的用途 |
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| Country | Link |
|---|---|
| US (1) | US20120263974A1 (zh) |
| EP (1) | EP2507306B1 (zh) |
| JP (2) | JP2013512978A (zh) |
| KR (1) | KR20120114287A (zh) |
| CN (1) | CN102639625B (zh) |
| BR (1) | BR112012013206A2 (zh) |
| CA (1) | CA2782133A1 (zh) |
| MX (1) | MX340886B (zh) |
| WO (1) | WO2011067198A1 (zh) |
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| CN106633277A (zh) * | 2009-12-02 | 2017-05-10 | 巴斯夫欧洲公司 | 光敏分子和金属配合物作为氧清除剂成分的用途 |
| CN104603195B (zh) * | 2012-09-07 | 2016-09-21 | 三菱瓦斯化学株式会社 | 吸氧性树脂组合物和使用其的吸氧性多层体 |
| US10232593B2 (en) * | 2013-03-13 | 2019-03-19 | The Sherwin-Williams Company | Oxygen-scavenging composition and articles thereof |
| JP2016147932A (ja) * | 2015-02-10 | 2016-08-18 | 学校法人早稲田大学 | 酸素除去用樹脂組成物及び食品保存用フィルム |
| EP3281788A1 (en) * | 2016-08-12 | 2018-02-14 | Clariant International Ltd | Oxygen barrier plastic material |
| EP3500115B1 (en) | 2016-08-17 | 2020-09-30 | Philip Morris Products S.a.s. | Aerosol-generating article having improved wrapper |
| JP7127257B2 (ja) * | 2017-09-08 | 2022-08-30 | 東洋製罐株式会社 | 酸素吸収性樹脂組成物及びその製造方法、並びに容器 |
| WO2019168135A1 (ja) * | 2018-02-28 | 2019-09-06 | 高砂香料工業株式会社 | 第四周期遷移金属錯体を触媒とするｎ，ｎ－ジアルキルアミド化合物からエステル化合物に変換する方法 |
| CN115869923B (zh) * | 2022-12-28 | 2024-03-22 | 威格科技(苏州)股份有限公司 | 一种吸氧材料及其制备方法及其制备的可同时吸附氧气和有机溶剂的吸附材料 |
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- 2010-11-29 MX MX2012006230A patent/MX340886B/es active IP Right Grant
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- 2010-11-29 US US13/511,231 patent/US20120263974A1/en not_active Abandoned
- 2010-11-29 WO PCT/EP2010/068374 patent/WO2011067198A1/en active Application Filing
- 2010-11-29 JP JP2012541433A patent/JP2013512978A/ja active Pending
- 2010-11-29 CA CA2782133A patent/CA2782133A1/en not_active Abandoned
- 2010-11-29 CN CN201080054866.0A patent/CN102639625B/zh not_active Expired - Fee Related
- 2010-11-29 BR BR112012013206A patent/BR112012013206A2/pt not_active Application Discontinuation
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| CN101258194A (zh) * | 2005-09-07 | 2008-09-03 | 西巴特殊化学品控股有限公司 | 降解性聚合物制品 |
Also Published As
| Publication number | Publication date |
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| JP2016033223A (ja) | 2016-03-10 |
| BR112012013206A2 (pt) | 2016-03-01 |
| MX2012006230A (es) | 2012-07-03 |
| JP2013512978A (ja) | 2013-04-18 |
| MX340886B (es) | 2016-07-29 |
| EP2507306A1 (en) | 2012-10-10 |
| US20120263974A1 (en) | 2012-10-18 |
| CN102639625A (zh) | 2012-08-15 |
| EP2507306B1 (en) | 2017-01-18 |
| KR20120114287A (ko) | 2012-10-16 |
| WO2011067198A1 (en) | 2011-06-09 |
| CA2782133A1 (en) | 2011-06-09 |
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