CN102575088A - 具有短诱导期的除氧树脂 - Google Patents
具有短诱导期的除氧树脂 Download PDFInfo
- Publication number
- CN102575088A CN102575088A CN2010800174535A CN201080017453A CN102575088A CN 102575088 A CN102575088 A CN 102575088A CN 2010800174535 A CN2010800174535 A CN 2010800174535A CN 201080017453 A CN201080017453 A CN 201080017453A CN 102575088 A CN102575088 A CN 102575088A
- Authority
- CN
- China
- Prior art keywords
- zinc
- compsn
- glycol
- radical
- ether
- 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.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims description 11
- 239000011347 resin Substances 0.000 title claims description 11
- 239000001301 oxygen Substances 0.000 title description 29
- 229910052760 oxygen Inorganic materials 0.000 title description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title description 27
- 230000006698 induction Effects 0.000 title description 2
- 230000002000 scavenging effect Effects 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 101
- -1 poly(tetramethylene ether) Polymers 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 229920000728 polyester Polymers 0.000 claims abstract description 42
- 229920001634 Copolyester Polymers 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 30
- 229920000570 polyether Polymers 0.000 claims abstract description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 102
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 49
- 239000011701 zinc Substances 0.000 claims description 40
- 229910052725 zinc Inorganic materials 0.000 claims description 37
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 28
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 25
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 16
- 239000004246 zinc acetate Substances 0.000 claims description 16
- 150000002500 ions Chemical class 0.000 claims description 15
- 239000010936 titanium Substances 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 229910052723 transition metal Inorganic materials 0.000 claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 11
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- 229910052719 titanium Inorganic materials 0.000 claims description 10
- 229910017052 cobalt Inorganic materials 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical group [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 241000790917 Dioxys <bee> Species 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 6
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 6
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052793 cadmium Inorganic materials 0.000 claims description 6
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 6
- 239000011651 chromium Substances 0.000 claims description 6
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052735 hafnium Inorganic materials 0.000 claims description 6
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- 229940049918 linoleate Drugs 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 6
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 229910052762 osmium Inorganic materials 0.000 claims description 6
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229940097411 palm acid Drugs 0.000 claims description 6
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- 229910052715 tantalum Inorganic materials 0.000 claims description 6
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 claims description 6
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052721 tungsten Inorganic materials 0.000 claims description 6
- 239000010937 tungsten Substances 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 6
- 235000016804 zinc Nutrition 0.000 claims description 6
- 239000011667 zinc carbonate Substances 0.000 claims description 6
- 235000004416 zinc carbonate Nutrition 0.000 claims description 6
- 229910000010 zinc carbonate Inorganic materials 0.000 claims description 6
- 239000011746 zinc citrate Substances 0.000 claims description 6
- 235000006076 zinc citrate Nutrition 0.000 claims description 6
- 229940068475 zinc citrate Drugs 0.000 claims description 6
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 6
- 229940007718 zinc hydroxide Drugs 0.000 claims description 6
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 6
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 claims description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001118 alkylidene group Chemical group 0.000 claims description 4
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Abstract
本发明涉及包含聚酯、共聚酯醚和氧化催化剂的组合物,其中该共聚酯醚包含锌化合物和至少一个选自聚(四亚甲基醚)和聚(四亚甲基-共-亚烷基醚)的聚醚链段。本发明进一步涉及由该组合物制成的制品和制造该组合物和制品的方法。
Description
对相关申请的交叉引用
本申请要求2009年1月20日提交的美国临时申请No. 61/154162的优先权。
发明领域
本发明涉及提供具有短除氧诱导期(oxygen scavenging induction period)的活性氧气阻隔(active
oxygen gas barrier)的共聚酯-醚组合物和有机聚合物组合物。
发明背景
塑料材料,如聚酯,由于它们与玻璃相比较轻的重量、降低的破损和可能较低的成本,已在代替玻璃和金属包装材料。在聚酯用于这些应用的用途中的一个问题是其较高的透气性。这限制了碳酸软饮料和氧敏感材料,如啤酒和果汁的贮存寿命。部分响应包装中的材料具有更长贮存寿命的食品工业目标,已开发用于与塑料,如聚酯混合的有机除氧材料。
使用目前所用的除氧材料的一种方法涉及使用“活性包装”,其中该包装以一定方式改性以控制产品对于氧气的暴露。一种技术涉及将除氧剂加入包装结构本身中。在这种包装结构中,除氧材料构成该包装的至少一部分。这些材料从封闭的包装体积中除去产品周围或可能渗入包装中的氧,由此在食品的情况下抑制变质和延长新鲜度。这种包装结构中所用的除氧材料包括通常加入聚合物或可氧化有机聚合物中的低分子量低聚物,其中该聚合物的骨架或侧链与氧反应。包装结构中所用的常见可氧化聚合物是聚酰胺,如MXD-6尼龙。这种除氧材料常与合适的催化剂,例如过渡金属催化剂,如钴的有机或无机盐一起使用。
美国专利No. 6,455,620公开了聚醚,如聚(环氧烷)二醇-例如聚环氧丁烷二醇作为与热塑性聚合物和过渡金属催化剂共混的除氧部分。通常用钛醇盐(titanium alkoxide)催化剂催化共聚酯-醚。一旦形成该包装,除氧树脂开始除氧所需的时间被称作“除氧诱导期”。美国专利No. 6,455,620中教导的组合物在与聚酯共混时在清除拉伸吹塑容器中的氧之前具有长的除氧诱导期。
发明概述
希望除氧树脂具有短“除氧诱导期”以在用食品或饮料装填包装制品后立即除氧。合意的是使该食品或饮料本身不与包装顶空中的氧或渗透包装壁的氧反应。希望除氧诱导期短以使包装的内容物不会暴露在氧中任何相当长的时间内。在将除氧树脂添加到构成该包装的主要部分的热塑性材料中时,还希望最终包装制品保持高透明度或低“浊度”。
因此,需要可以在与聚酯的相容共混物中用在单层包装制品中的共聚酯-醚,以使由该共混物制成的制品具有短除氧诱导期。
根据本发明,现在已经发现,某些共聚酯-醚可以在与聚酯的相容共混物中用在单层包装制品中,以使由该共混物制成的制品具有短除氧诱导期。本发明涉及包含聚酯、共聚酯醚和氧化催化剂的组合物,其中该共聚酯醚包含锌化合物和至少一个选自聚(四亚甲基醚)和聚(四亚甲基-共-亚烷基醚)的聚醚链段。本发明进一步涉及由该组合物制成的制品和制造该组合物和制品的方法。
发明详述
本发明以包含聚酯、共聚酯醚和氧化催化剂的组合物为特征,其中该共聚酯醚包含锌化合物和至少一个选自聚(四亚甲基醚)和聚(四亚甲基-共-亚烷基醚)的聚醚链段。该共聚酯醚可进一步包含选自聚(环氧乙烷)二醇、聚(环氧丙烷)二醇、聚(环氧丁烷)二醇、聚(环氧戊烷)二醇、聚(环氧己烷)二醇、聚(环氧庚烷)二醇、聚(环氧辛烷)二醇和衍生自环醚单体的聚(环氧烷)二醇的聚(环氧烷)二醇的聚醚链段。
聚(四亚甲基-共-亚烷基醚)的亚烷基可以是C2至C4,例如亚乙基、亚丙基或亚丁基,合适地其中该亚烷基是亚乙基或聚(四亚甲基-共-亚乙基醚)。该聚醚链段的分子量可以为大约200克/摩尔至大约5000克/摩尔,例如大约1000克/摩尔至大约3000克/摩尔。该聚醚链段中环氧烷的摩尔%可以为大约10摩尔%至大约90摩尔%,例如大约25摩尔%至大约75摩尔%或大约40摩尔%至大约60摩尔%。为了用于制备共聚酯醚,该聚醚链段的端基是羟基,例如聚(环氧丁烷)二醇或聚(四亚甲基-共-环氧烷)二醇,其例如可以是聚(四亚甲基-共-环氧乙烷)二醇或聚(四亚甲基-共-环氧丙烷)二醇。
选择最终组合物中的共聚酯醚总量以提供由该组合物形成的制品的所需除氧性能。共聚酯醚的量可以为总组合物的至少大约0.5重量%,或总组合物的大约0.5重量%至大约10重量%,例如总组合物的大约1.0重量%至大约5.0重量%,或大约1.5重量%至大约3.0重量%。该共聚酯醚可以与聚酯物理共混,或者,该聚(环氧烷)二醇可以与聚酯共聚。
该共聚酯醚可含有该共聚酯醚的大约15重量%至95重量%,例如该共聚酯醚的大约25重量%至大约75重量%或大约30重量%至大约70重量%的聚醚链段,使用乙二醇、丁二醇或丙二醇作为另一二醇。可以在聚合过程中添加抗氧化剂以控制酯-醚链段的降解。
可以通过与二羧酸的二烷基酯的酯交换来制造共聚酯醚。在酯交换过程中,二羧酸的二烷基酯在锌化合物作为催化剂存在下与一种或多种二醇发生酯交换。可以使用锌的化合物,如氧化物、氢氧化物、醇盐、脂族酸盐、草酸盐、柠檬酸盐、碳酸盐、卤化物或络合物,例如乙酸锌。该共聚酯-醚中元素锌的合适的量可以为共聚酯-醚重量的大约35至大约100 ppm,例如大约40-80 ppm。聚(环氧烷)二醇在这些酯化过程中替代这些二醇的一部分。聚(环氧烷)二醇可以与起始原材料一起添加或在酯化后添加。在任一情况下,可以在以升高的温度和1大气压或更大的压力运行的一个或多个反应器的序列中连续制造单体和低聚物混合物。或者,可以在一个或多个分批反应器中制造单体和低聚物混合物。在分批法中,可以使包含单体对苯二甲酸双羟乙酯(BHET)的单体剩余物留在酯交换反应器中以帮助下一批次的酯化。适于这些反应的条件是大约180℃至250℃的温度和大约1巴至4巴的压力。
接着,共聚酯醚单体和低聚物的混合物发生熔融相缩聚以产生低分子量前体聚合物。在以升高的温度运行的一个或多个反应器的序列中制造该前体。为促进过量二醇、水和其它反应产物的去除,缩聚反应器在真空下运行。缩聚反应用的催化剂包括锑、锗、锡、钛和铝的化合物,钛化合物是优选的。元素Ti的合适的量可以为大约20至大约60 ppm,例如大约25至35 ppm。缩聚用的反应条件可以包括(i)小于大约290℃或比共聚酯醚的熔点高大约10℃的温度;和(ii)小于大约0.01巴的压力,随聚合进行而降低。可以在以升高的温度和小于1大气压的压力运行的一个或多个反应器的序列中连续制造这种共聚酯醚。或者,可以在一个或多个分批反应器中制造这种共聚酯醚。熔融相聚合后的特性粘度可以为大约0.5
dl/g至大约1.5 dl/g。
在经模头挤出该熔融共聚酯醚后,将线束在冷水浴中骤冷并切成丸粒。这些丸粒可直接送入挤出机以形成制品,或在常规条件下固态化(solid stated)直至达到所需分子量。
要用在本发明中的聚酯可以由二酸或二酯组分和二醇组分的反应制成,该二酸或二酯组分包含至少65摩尔%,例如从至少65摩尔%到至少95摩尔%或至少95摩尔%的对苯二甲酸或对苯二甲酸C1-C4二烷基酯;该二醇组分包含至少65%摩尔%,例如从至少65摩尔%到至少95摩尔%或至少95摩尔%的乙二醇。二酸组分可以是对苯二甲酸,二醇组分可以是乙二醇,由此形成聚对苯二甲酸乙二醇酯(PET)。所有二酸组分的摩尔百分比合计100摩尔%,所有二醇组分的摩尔百分比合计100摩尔%。
当聚酯组分用一种或多种非二乙醇的二醇组分改性时,所述聚酯的合适的二醇组分可选自1,4-环己烷二甲醇、1,2-丙二醇、1,4-丁二醇、2,2-二甲基-1,3-丙二醇、2-甲基-1,3-丙二醇(2MPDO)、1,6-己二醇、1,2-环己二醇、1,4-环己二醇、1,2-环己烷二甲醇、1,3-环己烷二甲醇、2,2,4,4-四甲基-1,3-环丁二醇或在链中含有一个或多个氧原子的二醇,例如二乙二醇、三乙二醇、二丙二醇、三丙二醇或其混合物。该二醇可含有2至18个碳原子,例如2至8个碳原子。脂环族二醇可以以它们的顺式或反式构型或作为这两种形式的混合物使用。改性二醇组分可以是1,4-环己烷二甲醇或二乙二醇或这些的混合物。
如果聚酯组分用一种或多种非对苯二甲酸的酸组分改性,该线性聚酯的合适的酸组分(脂族、脂环族或芳族二羧酸)可选自间苯二甲酸、5-磺基间苯二甲酸、1,4-环己二羧酸、1,3-环己二羧酸、丁二酸、戊二酸、己二酸、癸二酸、1,12-十二烷二酸、2,6-萘二甲酸、联苯甲酸或这些的混合物等。在聚合物制备中,可以使用其官能酸衍生物,如二羧酸的二甲基、二乙基或二丙基酯。实际上,可以使用这些酸的酐或酰基卤。这些二羧酸改性剂与对苯二甲酸相比通常延迟结晶速率。本发明中可用的聚酯是PET和间苯二甲酸或5-磺基间苯二甲酸或这些的混合物的共聚物。总间苯二甲酸和5-磺基间苯二甲酸通常可以以该共聚物的大约1摩尔%至大约10摩尔%,或大约1.5摩尔%至6摩尔%存在。
除由对苯二甲酸(或对苯二甲酸二甲酯)和乙二醇制成的聚酯或如上所述的改性聚酯外,本发明还可包括使用100%芳族二酸,如2,6-萘二甲酸或联苯甲酸或它们的二酯,和通过使至少85摩尔%来自这些二酸/二酯的二羧酸酯与任何上述共聚单体反应制成的改性聚酯。
本发明的聚酯可以是选自聚对苯二甲酸乙二醇酯、聚萘二甲酸乙二醇酯、聚间苯二甲酸乙二醇酯、聚对苯二甲酸乙二醇酯的共聚物、聚萘二甲酸乙二醇酯的共聚物、聚间苯二甲酸乙二醇酯的共聚物或其混合物的至少一员;例如该聚酯可以是聚对苯二甲酸乙二醇酯的共聚物,如聚(对苯二甲酸乙二醇酯-共-间苯二甲酸乙二醇酯)或聚(对苯二甲酸乙二醇酯-共-5-磺基间苯二甲酸乙二醇酯)。
合适的氧化催化剂包括活化或促进该共聚酯醚的氧化的过渡金属催化剂。该过渡金属可以是具有选自周期表第一、第二或第三过渡系列的金属的过渡金属盐的形式。合适的过渡金属包括钴、铜、铑、钌、钯、钨、锇、镉、银、钽、铪、钒、钛、铬、镍、锌、锰或其混合物。该金属的合适的抗衡离子包括,但不限于,羧酸根,如新癸酸根、辛酸根、硬脂酸根、乙酸根、萘酸根、乳酸根、马来酸根、乙酰丙酮酸根、亚油酸根、油酸根、棕榈酸根或2-乙基己酸根,氧离子(oxides)、硼离子(borides)、碳酸根、氯离子(chlorides)、二氧根(dioxides)、氢氧根、硝酸根、磷酸根、硫酸根、硅酸根或其混合物。例如,硬脂酸钴和乙酸钴是本发明中可用的氧化催化剂。可以使用有效催化氧清除的任何量的催化剂,例如总组合物的至少大约10
ppm或总组合物的大约25 ppm至大约500
ppm,例如总组合物的大约50 ppm至大约250
ppm或大约50 ppm至大约100
ppm。该氧化催化剂可以在聚合过程中添加或作为聚酯基母料配混,该母料可以在通过将聚酯与共聚酯醚共混形成的制品的制备过程中添加。
该锌化合物可以选自氧化锌、氢氧化锌、锌醇盐、锌的脂族酸盐、乙酸锌、草酸锌、柠檬酸锌、碳酸锌、卤化锌和锌的络合物;例如该锌化合物可以是乙酸锌。该锌化合物可以以总组合物的大约40 ppm至大约100 ppm,例如总组合物的大约50 ppm至大约80 ppm的量存在。
本发明的组合物可进一步包含添加剂。该添加剂可以选自热稳定剂、防粘连剂、抗氧化剂、抗静电剂、紫外线吸收剂、调色剂(例如颜料和染料)、填料、支化剂或其它典型试剂。例如,该添加剂可以是选自热稳定剂、防粘连剂、抗氧化剂、抗静电剂、紫外线吸收剂、颜料、染料、填料、支化剂及其混合物的至少一员。该添加剂可以通常在缩聚反应过程中或在接近缩聚反应结束时添加到该组合物中。可使用常规系统来引入添加剂以实现所需结果。
本发明的另一实施方案是包含上述组合物的制品。合适的制品包括,但不限于,膜、片、管材、管道、纤维、容器预成型坯、吹塑制品如刚性容器、热成形制品、挠性袋等,和它们的组合。该制品可包含一层或多层上述组合物。典型的刚性或半刚性制品可以由塑料、纸或纸板箱或瓶子形成,如果汁、牛奶、软饮料、啤酒和汤容器、热成形托盘或杯。此外,此类制品的壁通常包含多层材料。可以在一层、一些层或所有这些层中使用本发明。
本发明的另一实施方案是制造除氧树脂的方法,包括:a) 在锌化合物存在下用亚烷基二醇和聚(环氧烷)二醇酯化或酯交换聚酯前体以形成共聚酯醚,其中该共聚酯醚包含至少一个选自聚(四亚甲基醚)和聚(四亚甲基-共-亚烷基醚)的聚醚链段,b) 将该共聚酯醚与聚酯和氧化催化剂共混,c) 熔化该共混物以形成均匀共混物,和d) 将该熔融共混物冷却和切割成固体丸粒。该聚酯前体可以选自纯对苯二甲酸和对苯二甲酸二甲酯。该亚烷基二醇可选自乙二醇、丙二醇和丁二醇;例如乙二醇。锌化合物可选自氧化锌、氢氧化锌、锌醇盐、锌的脂族酸盐、乙酸锌、草酸锌、柠檬酸锌、碳酸锌、卤化锌和锌的络合物;例如乙酸锌。该氧化催化剂可以是过渡金属盐,其包含i) 含有选自钴、铜、铑、钌、钯、钨、锇、镉、银、钽、铪、钒、钛、铬、镍、锌、锰及其混合物的至少一员的金属,和ii) 含有选自羧酸根、氧离子、硼离子、碳酸根、氯离子、二氧根、氢氧根、硝酸根、磷酸根、硫酸根、硅酸根及其混合物的至少一员的抗衡离子。该羧酸根可以选自新癸酸根、辛酸根、硬脂酸根、乙酸根、萘酸根、乳酸根、马来酸根、乙酰丙酮酸根、亚油酸根、油酸根、棕榈酸根或2-乙基己酸根。例如该氧化催化剂可以是选自硬脂酸钴和乙酸钴的至少一员。
本发明的另一实施方案是降低聚酯制品的透气性的方法,包括:a) 在锌化合物存在下用亚烷基二醇和聚(环氧烷)二醇酯化或酯交换聚酯前体以形成共聚酯醚,其中该共聚酯醚包含至少一个选自聚(四亚甲基醚)和聚(四亚甲基-共-亚烷基醚)的聚醚链段,b) 将该共聚酯醚与聚酯和氧化催化剂共混以形成混合物,c) 熔化该混合物,和d) 形成包含该混合物的制品。该聚酯前体可选自纯对苯二甲酸和对苯二甲酸二甲酯。亚烷基二醇可选自乙二醇、丙二醇和丁二醇;例如乙二醇。锌化合物可选自氧化锌、氢氧化锌、锌醇盐、锌的脂族酸盐、乙酸锌、草酸锌、柠檬酸锌、碳酸锌、卤化锌和锌的络合物;例如乙酸锌。该氧化催化剂可以是过渡金属盐,其包含i) 含有选自钴、铜、铑、钌、钯、钨、锇、镉、银、钽、铪、钒、钛、铬、镍、锌、锰及其混合物的至少一员的金属,和ii) 含有选自羧酸根、氧离子、硼离子、碳酸根、氯离子、二氧根、氢氧根、硝酸根、磷酸根、硫酸根、硅酸根及其混合物的至少一员的抗衡离子。羧酸根可以选自新癸酸根、辛酸根、硬脂酸根、乙酸根、萘酸根、乳酸根、马来酸根、乙酰丙酮酸根、亚油酸根、油酸根、棕榈酸根或2-乙基己酸根。例如该氧化催化剂可以是选自硬脂酸钴和乙酸钴的至少一员。
试验程序
1. 特性粘度
根据ASTM D 4603使用间甲酚作为溶剂测量共聚酯-醚的特性粘度。
2. 瓶子的氧渗透
用Mocon Ox-Tran型号2/60 (MOCON Minneapolis, MN)测量在环境相对湿度、1大气压和23℃下的瓶样品的氧通量。使用98%氮气与2%氢气的混合物作为载气,并使用环境空气(20.9%氧气)作为试验气体。在测试前,试样在装置内的氮气中适应最少24小时以除去痕量的大气氧。继续调适直至获得稳定基线,在此在45分钟周期内氧通量的改变小于1%。在通量达到稳态(在此在45分钟试验周期过程中氧通量的改变小于1%)时试验结束。测量氧渗透结果并记录为立方厘米/包装/天。为了测量阻隔改进系数或“BIF”;与受试瓶同时在相同条件下测量不含除氧剂的对照瓶。通过将对照瓶的氧渗透除以受试瓶的氧渗透,计算BIF。为了有利于测定氧清除开始前的诱导期,使用10.0X的BIF值。这意味着受试瓶具有不大于对照瓶的10%的透氧率。
3. 瓶壁浊度
用Hunter Lab ColorQuest II仪器测量瓶壁的浊度。D65光源与CIE 1964 10°标准观察器一起使用。浊度是指CIE Y漫透射率相对于CIE Y全透射的百分比。除非另行指明,在厚度为0.25毫米的拉伸吹塑瓶的侧壁上测量%浊度。
4. 元素含量
用Atom Scan 16 ICP发射摄谱仪测量磨碎的聚合物样品的元素含量。通过在乙醇胺中加热来溶解该样品,并在冷却时添加蒸馏水以结晶出对苯二甲酸。将该溶液离心,分析上清液。来自被分析的样品的原子发射与具有已知元素离子浓度的溶液的比较用于测定留在聚合物样品中的元素的实验值。使用这种方法测定该组合物中的钴和锌浓度。
实施例
实施例1(对比)
将DMT、摩尔过量的二醇和作为酯交换催化剂的钛酸四正丁酯(Tyzor®, DuPont, USA)(50 ppm Ti)装入配有冷凝器、回流柱和搅拌器的反应器中。将在酯交换过程中连续搅拌的材料在大气压下加热至160-230℃的温度,直至酯交换反应完成,如除去的甲醇量所显示。将该混合物转移到高压釜中,加入数均分子量为1400克/摩尔的聚(环氧丁烷)二醇,相当于最终聚合物重量的50重量%,以及作为缩聚催化剂的Vertec® AC420(Johnson Mathey, USA)(30
ppm Ti)。将高压釜压力降至<0.3 mm Hg,随后将温度升至250℃。在聚合过程中连续搅拌的混合物保持在此温度下,直至达到通过搅拌器安培数测得的所需熔体粘度。该反应器用氮气轻微加压并将产物挤出到冷水中。在聚合物线料(strand)冷却后,其用Scheer-bay造粒机造粒。该共聚酯-醚的特性粘度为大约1.2
dl/g。将树脂(2重量%)干燥,与干燥的基础聚酯2300K树脂(Invista
Polyester & Resins, USA;这种树脂基于对苯二甲酸和含有0.2重量%钠盐形式的5-磺基间苯二甲酸的乙二醇的标准锑催化的直接酯化,且后添加硬脂酸钴(75
ppm钴))共混并注射成形成为预成型坯。将预成型坯拉伸吹塑成500毫升的24克瓶。测量这些瓶的氧渗透和浊度。BIF结果列在表1中,%浊度在表2中。
实施例2(对比)
通过配混标准聚酯树脂(Invista类型2201)和二水合乙酸锌(1.5重量%)以得到4545 ppm的锌元素含量,制备PET/乙酸锌母料。
将来自实施例1的共聚酯-醚与这种乙酸锌母料共混以得到75 ppm的锌含量。将这种干燥的共混物(2重量%)与2300K聚酯树脂共混并挤出成为预成型坯。将预成型坯拉伸吹塑成500毫升的24克瓶。测量这些瓶的氧渗透和浊度。BIF结果列在表1中,%浊度在表2中。
实施例3
使用实施例1的方法制备共聚酯-醚,差别在于使用乙酸锌(70 ppm Zn)代替Tyzor
Ti催化剂作为酯交换催化剂。测量这些瓶的氧渗透和浊度。BIF结果列在表1中,%浊度在表2中。
实施例4(对比)
将PTMEG换成56重量%的分子量为2000克/摩尔的聚(四亚甲基-共-环氧乙烷)二醇(含有50摩尔%环氧乙烷链段),重复实施例1。此外,在酯交换反应后添加500 ppm抗氧化剂(Ethanox®
330, Albemarle Corp., USA)。测量这些瓶的氧渗透,BIF结果列在表1中。
实施例5
将PTMEG换成56重量%的分子量为2000克/摩尔的聚(四亚甲基-共-环氧乙烷)二醇(含有50摩尔%环氧乙烷链段),重复实施例3。此外,在酯交换反应后添加500 ppm抗氧化剂(Ethanox®
330)。测量这些瓶的氧渗透,BIF结果列在表1中。
实施例6
重复实施例5,不添加抗氧化剂。测量这些瓶的氧渗透,BIF结果列在表1中。
实施例7
用40 ppm Zn作为酯交换催化剂和55
ppm Ti作为缩聚催化剂,重复实施例3。此外,在酯交换反应后添加100
ppm抗氧化剂(Ethanox® 330)。测量这些瓶的氧渗透,BIF结果列在表1中。
实施例8
用45 ppm Zn作为酯交换催化剂和30
ppm Ti作为缩聚催化剂,重复实施例7。测量这些瓶的氧渗透,BIF结果列在表1中。
表1
BIF值
使用锌化合物作为酯交换催化剂的本发明的实施例(3,5-8)具有比使用钛酯交换催化剂的对比例(1、2和4)短得多的除氧诱导期。此外,如表2中所示,瓶壁浊度可接受。
表2
实施例 | 瓶侧壁浊度, % |
对照物 | 1.04 |
1 (Comp.) | 1.56 |
2 (Comp.) | 2.77 |
3 | 1.49 |
尽管已联系其具体实施方案描述了本发明,但明显地,许多备选方案、修改和变动是本领域技术人员根据上文的描述显而易见的。因此,旨在涵盖落在所附权利要求的精神和宽范围内的所有这样的备选方案、修改和变动。
Claims (42)
1.包含聚酯、共聚酯醚和氧化催化剂的组合物,其中该共聚酯醚包含锌化合物和至少一个选自聚(四亚甲基醚)和聚(四亚甲基-共-亚烷基醚)的聚醚链段。
2.权利要求1的组合物,其中所述共聚酯醚进一步包含聚(环氧烷)二醇的聚醚链段,该聚(环氧烷)二醇选自聚(环氧乙烷)二醇、聚(环氧丙烷)二醇、聚(环氧丁烷)二醇、聚(环氧戊烷)二醇、聚(环氧己烷)二醇、聚(环氧庚烷)二醇、聚(环氧辛烷)二醇和衍生自环醚单体的聚(环氧烷)二醇。
3.权利要求1的组合物,其中所述聚(四亚甲基-共-亚烷基醚)的所述亚烷基选自亚乙基、亚丙基或亚丁基。
4.权利要求3的组合物,其中所述亚烷基是亚乙基。
5.权利要求1的组合物,其中所述聚醚链段的分子量为大约200克/摩尔至大约5000克/摩尔。
6.权利要求1的组合物,其中所述共聚酯醚以总组合物的至少大约0.5重量%的量存在。
7.权利要求1的组合物,其中所述共聚酯醚以总组合物的大约0.5重量%至大约10重量%的量存在。
8.权利要求1的组合物,其中所述聚醚链段以所述共聚酯醚的大约15重量%至大约95重量%的量存在。
9.权利要求1的组合物,其中所述聚酯是选自聚对苯二甲酸乙二醇酯、聚萘二甲酸乙二醇酯、聚间苯二甲酸乙二醇酯、聚对苯二甲酸乙二醇酯的共聚物、聚萘二甲酸乙二醇酯的共聚物、聚间苯二甲酸乙二醇酯的共聚物及其混合物的至少一员。
10.权利要求9的组合物,其中所述聚酯是聚对苯二甲酸乙二醇酯的共聚物。
11.权利要求1的组合物,其中该氧化催化剂包含过渡金属盐,该过渡金属盐包含i) 金属,该金属含有选自钴、铜、铑、钌、钯、钨、锇、镉、银、钽、铪、钒、钛、铬、镍、锌、锰及其混合物的至少一员,和ii) 抗衡离子,该抗衡离子含有选自羧酸根、氧离子、硼离子、碳酸根、氯离子、二氧根、氢氧根、硝酸根、磷酸根、硫酸根、硅酸根及其混合物的至少一员。
12.权利要求11的组合物,其中所述羧酸根选自新癸酸根、辛酸根、硬脂酸根、乙酸根、萘酸根、乳酸根、马来酸根、乙酰丙酮酸根、亚油酸根、油酸根、棕榈酸根或2-乙基己酸根。
13.权利要求1的组合物,其中所述氧化催化剂是选自硬脂酸钴和乙酸钴的至少一员。
14.权利要求1的组合物,其中所述氧化催化剂以总组合物的至少大约10 ppm的量存在。
15.权利要求1的组合物,其中所述氧化催化剂以总组合物的大约25 ppm和大约500 ppm的量存在。
16.权利要求1的组合物,其中所述锌化合物选自氧化锌、氢氧化锌、锌醇盐、锌的脂族酸盐、乙酸锌、草酸锌、柠檬酸锌、碳酸锌、卤化锌和锌的络合物。
17.权利要求1的组合物,其中所述锌化合物是乙酸锌。
18.权利要求1的组合物,其中所述锌化合物以总组合物的大约35 ppm至大约100 ppm的量存在。
19.权利要求1的组合物,其中所述锌化合物以总组合物的大约40 ppm至大约80 ppm的量存在。
20.权利要求1的组合物,进一步包含添加剂。
21.权利要求20的组合物,其中该添加剂包含选自热稳定剂、防粘连剂、抗氧化剂、抗静电剂、紫外线吸收剂、颜料、染料、填料、支化剂及其混合物的至少一员。
22.包含权利要求1的组合物的制品。
23.权利要求22的制品,其中该制品选自膜、片、管材、管道、纤维、容器预成型坯、吹塑制品、热成形制品和挠性袋。
24.权利要求22的制品,其中该制品包含一层或多层该组合物。
25.制造除氧树脂的方法,包括:
a) 在锌化合物存在下用亚烷基二醇和聚(环氧烷)二醇酯化或酯交换聚酯前体以形成共聚酯醚,其中该共聚酯醚包含至少一个选自聚(四亚甲基醚)和聚(四亚甲基-共-亚烷基醚)的聚醚链段,
b) 将该共聚酯醚与聚酯和氧化催化剂共混,
c) 熔化该共混物以形成均匀共混物,和
d) 将该熔融共混物冷却和切割成固体丸粒。
26.权利要求25的方法,其中该聚酯前体选自纯对苯二甲酸和对苯二甲酸二甲酯。
27.权利要求25的方法,其中该亚烷基二醇选自乙二醇、丙二醇和丁二醇。
28.权利要求25的方法,其中该亚烷基二醇是乙二醇。
29.权利要求25的方法,其中所述锌化合物选自氧化锌、氢氧化锌、锌醇盐、锌的脂族酸盐、乙酸锌、草酸锌、柠檬酸锌、碳酸锌、卤化锌和锌的络合物。
30.权利要求25的方法,其中所述锌化合物是乙酸锌。
31.权利要求25的方法,其中所述氧化催化剂包含过渡金属盐,该过渡金属盐包含i) 金属,该金属含有选自钴、铜、铑、钌、钯、钨、锇、镉、银、钽、铪、钒、钛、铬、镍、锌、锰及其混合物的至少一员,和ii) 抗衡离子,该抗衡离子含有选自羧酸根、氧离子、硼离子、碳酸根、氯离子、二氧根、氢氧根、硝酸根、磷酸根、硫酸根、硅酸根及其混合物的至少一员。
32.权利要求31的方法,其中所述羧酸根选自新癸酸根、辛酸根、硬脂酸根、乙酸根、萘酸根、乳酸根、马来酸根、乙酰丙酮酸根、亚油酸根、油酸根、棕榈酸根或2-乙基己酸根。
33.权利要求25的方法,其中所述氧化催化剂是选自硬脂酸钴和乙酸钴的至少一员。
34.降低聚酯制品的透气性的方法,包括:
a) 在锌化合物存在下用亚烷基二醇和聚(环氧烷)二醇酯化或酯交换聚酯前体以形成共聚酯醚,其中该共聚酯醚包含至少一个选自聚(四亚甲基醚)和聚(四亚甲基-共-亚烷基醚)的聚醚链段,
b) 将该共聚酯醚与聚酯和氧化催化剂共混以形成混合物,
c) 熔化该混合物,和
d) 形成包含该混合物的制品。
35.权利要求34的方法,其中该聚酯前体选自纯对苯二甲酸和对苯二甲酸二甲酯。
36.权利要求34的方法,其中该亚烷基二醇选自乙二醇、丙二醇和丁二醇。
37.权利要求34的方法,其中该亚烷基二醇是乙二醇。
38.权利要求34的方法,其中所述锌化合物选自氧化锌、氢氧化锌、锌醇盐、锌的脂族酸盐、乙酸锌、草酸锌、柠檬酸锌、碳酸锌、卤化锌和锌的络合物。
39.权利要求34的方法,其中所述锌化合物是乙酸锌。
40.权利要求34的方法,其中所述氧化催化剂包含过渡金属盐,该过渡金属盐包含i) 金属,该金属含有选自钴、铜、铑、钌、钯、钨、锇、镉、银、钽、铪、钒、钛、铬、镍、锌、锰及其混合物的至少一员,和ii)抗衡离子,该抗衡离子含有选自羧酸根、氧离子、硼离子、碳酸根、氯离子、二氧根、氢氧根、硝酸根、磷酸根、硫酸根、硅酸根及其混合物的至少一员。
41.权利要求40的方法,其中所述羧酸根选自新癸酸根、辛酸根、硬脂酸根、乙酸根、萘酸根、乳酸根、马来酸根、乙酰丙酮酸根、亚油酸根、油酸根、棕榈酸根或2-乙基己酸根。
42.权利要求34的方法,其中所述氧化催化剂是选自硬脂酸钴和乙酸钴的至少一员。
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RU2011138421A (ru) | 2013-03-27 |
UA105916C2 (uk) | 2014-07-10 |
KR101742831B1 (ko) | 2017-06-15 |
CN102575088B (zh) | 2015-02-04 |
WO2010096459A2 (en) | 2010-08-26 |
WO2010096459A3 (en) | 2010-12-02 |
EP2398857A2 (en) | 2011-12-28 |
KR20110124775A (ko) | 2011-11-17 |
US20120114887A1 (en) | 2012-05-10 |
EP2398857A4 (en) | 2015-01-21 |
US8647728B2 (en) | 2014-02-11 |
JP5779507B2 (ja) | 2015-09-16 |
EP2398857B1 (en) | 2016-07-27 |
RU2534083C2 (ru) | 2014-11-27 |
JP2012518709A (ja) | 2012-08-16 |
CL2011002018A1 (es) | 2012-04-13 |
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