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公开(公告)号：US4892677A
公开(公告)日：1990-01-09
申请号：US683443
申请日：1984-12-19
CPC分类号： G07C1/00 , G01N31/229 , Y10S252/962 , Y10S428/913
摘要： A new process is described which is useful for producing novel articles of manufacture useful for monitoring the time-temperature history of perishable items. The process initially involves forming a solution comprised of a diacetylenic monomer and a solvent. The solution is frozen, and the frozen solution having crystalline diacetylenic monomer therein is irradiated to partially polymerize the diacetylenic monomer. Partial polymerization of the crystalline diacetylenic monomer admixed with frozen solvent results in the production of a novel article of manufacture having color. The novel article of manufacture is comprised of frozen solvent, diacetylenic monomer, and colored polydiacetylene. Due to the intensity of the color of the polydiacetylene, the entire article of manufacture appears to be colored.The colored article of manufacture may be attached to various perishables to monitor the shelf life of the perishables. upon exposure to temperatures above a critical temperature, the frozen solvent melts and extracts unreached monomer from the colored polymer, thereby causing a sharp color transition which indicates that the perishable should possibly be discarded.
摘要翻译： 描述了一种新方法，其可用于生产可用于监测易腐物品的时间 - 温度历史的新型制品。 该方法最初涉及形成由二乙炔单体和溶剂组成的溶液。 将溶液冷冻，照射其中具有结晶二炔单体的冷冻溶液以部分聚合二乙炔单体。 与冷冻溶剂混合的结晶二乙炔单体的部分聚合导致生产具有颜色的新型制品。 新型制品由冷冻溶剂，二乙炔单体和着色聚二乙炔组成。 由于聚二乙炔颜色的强度，整个制品似乎是有色的。 有色制品可以附着在各种易腐食品上，以监测易腐品的保质期。 在暴露于高于临界温度的温度下，冷冻的溶剂熔融并从着色聚合物中提取未接触的单体，从而引起明显的颜色转变，这表明易腐物质可能被丢弃。
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公开(公告)号：US4735745A
公开(公告)日：1988-04-05
申请号：US373955
申请日：1982-05-03
CPC分类号： G07C1/00 , G01N31/229 , Y10S252/962 , Y10S428/913
摘要： A new process is described which is useful for producing novel articles of manufacture useful for monitoring the time-temperature history of perishable items. The process initially involves forming a solution comprised of a diacetylenic monomer and a solvent. The solution is frozen, and the frozen solution having crystalline diacetylenic monomer therein is irradiated to partially polymerize the diacetylenic monomer. Partial polymerization of the crystalline diacetylenic monomer admixed with frozen solvent results in the production of a novel article of manufacture having color. The novel article of manufacture is comprised of frozen solvent, diacetylenic monomer, and colored polydiacetylene. Due to the intensity of the color of the polydiacetylene, the entire article of manufacture appears to be colored.The colored article of manufacture may be attached to various perishables to monitor the shelf life of the perishables. Upon exposure to temperatures above a critical temperature, the frozen solvent melts and extracts unreacted monomer from the colored polymer, thereby causing a sharp color transition which indicates that the perishable should possibly be discarded.
摘要翻译： 描述了一种新方法，其可用于生产可用于监测易腐物品的时间 - 温度历史的新型制品。 该方法最初涉及形成由二乙炔单体和溶剂组成的溶液。 将溶液冷冻，照射其中具有结晶二炔单体的冷冻溶液以部分聚合二乙炔单体。 与冷冻溶剂混合的结晶二乙炔单体的部分聚合导致生产具有颜色的新型制品。 新型制品由冷冻溶剂，二乙炔单体和着色聚二乙炔组成。 由于聚二乙炔颜色的强度，整个制品似乎是有色的。 有色制品可以附着在各种易腐食品上，以监测易腐品的保质期。 当暴露于高于临界温度的温度时，冷冻溶剂从着色聚合物中熔融并提取未反应的单体，从而引起明显的颜色转变，这表明易腐烂物可能被丢弃。
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3.发明授权Metal complexed acetylenic compounds useful as environmental indicating materials 失效金属络合的炔属化合物可用作环境指示材料
公开(公告)号：US4788151A
公开(公告)日：1988-11-29
申请号：US912711
申请日：1986-09-29
IPC分类号： C07C275/20 , C07C275/28 , C07F1/00 , C07F3/00 , C07F19/00 , G01N31/22 , G01K11/16 , C07C127/15
CPC分类号： C07C275/28 , C07C275/20 , C07F1/005 , C07F19/005 , C07F3/003 , G01N31/22 , G01N31/222
摘要： Acetylenic complexes are disclosed that are useful as environmental indicating materials whereby exposure thereof to environmental stimuli induces a color change. These complexes contain at least one effective complexing metal and at least one acetylenic compound of the general formula:[R--(C"C).sub.a --(CH.sub.2).sub.b --(C"C).sub.c ].sub.2.dHXWherein a is 1 or 2, b is about 0-5; c is 0 or 1; with the proviso that when a is 1, b and c are 0, when a is 2, b is about 0-5 and c is 0 or 1; and R is --(CH.sub.2).sub.n -NHC(O)NHR'; wherein n is an integer of about 1 to 10; and R' is selected from the group consisting of: (a) hydrogen; (b) cycloalkyl; (c) alkenyl; (d) cycloalkenyl; (e) alkyl; (f) phenyl; (g) alkoxy; (h) alkoxy alkyl; and (i) alkoxycarbonylalkyl.
摘要翻译： 公开了作为环境指示材料有用的乙炔配合物，由此其暴露于环境刺激物引起颜色变化。 这些络合物含有至少一种有效的络合金属和至少一种具有以下通式的炔属化合物：[R-（C“C）a-（CH 2）b - （C”C）c] 2.dHX其中a为1或 2，b约为0-5; c为0或1; 条件是当a为1时，b和c为0，当a为2时，b为约0-5，c为0或1; 并且R是 - （CH 2）n -NHC（O）NHR'; 其中n为约1至10的整数; 和R'选自：（a）氢; （b）环烷基; （c）烯基; （d）环烯基; （e）烷基; （f）苯基; （g）烷氧基; （h）烷氧基烷基; 和（i）烷氧基羰基烷基。
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4.发明授权Acid complexed acetylenic compounds useful as environmental indicating materials 失效酸性络合的炔属化合物可用作环境指示材料
公开(公告)号：US4789637A
公开(公告)日：1988-12-06
申请号：US912713
申请日：1986-09-29
IPC分类号： G01N31/22 , G01N33/02 , C07C127/15 , G01K11/14
摘要： A family of acetylenic complexes especially useful as environmental indicators is provided. The complexes include at least one complexing acid and one acetylenic compound of the formula:[R--(C.tbd.C).sub.a --(CH.sub.2).sub.b --(C.tbd.C).sub.c ].sub.2.dHXwherein, a is 1 or 2; b is about 0-5; c is 0 or 1; d is above 0 to about 2, with the proviso that when a is 1, b and c are 0, and when a is 2, b is about 0-5 and c is 0 or 1; and R is --(CH.sub.2)n--NHC(O)NHR'; wherein n is an integer of about 1 to 10; and R' is selected from a group consisting of hydrogen, cycloalkyl, alkenyl, cycloalkenyl, aklyl, phenyl, alkoxyl, alkoxylcarbonylalkyl, and X is a complexing acid.
摘要翻译： 提供了特别用作环境指标的炔属复合物系列。 络合物包括至少一种络合酸和一个下式的炔属化合物：[R-（C 3 B）C - （CH 2）b - （C 3 F 3）C] 2 dHX其中a为1或2; b约为0-5; c为0或1; d大于0至约2，条件是当a为1时，b和c为0，当a为2时，b为约0-5，c为0或1; 并且R是 - （CH 2）n -NHC（O）NHR'; 其中n为约1至10的整数; 并且R'选自氢，环烷基，烯基，环烯基，烷基，苯基，烷氧基，烷氧基羰基烷基，X是络合酸。
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5.发明授权Co-crystallizable diacetylenic monomer compositions, crystal phases and mixtures, and related methods 有权可共结构的二炔单体组合物，结晶相和混合物及相关方法公开(公告)号：US08354486B2
公开(公告)日：2013-01-15
申请号：US12730835
申请日：2010-03-24
申请人： Elizabeth Castillo Martinez , Ray H. Baughman , Lee J. Hall , Mikhail Kozlov , Dawn E. Smith , Thaddeus Prusik , Carl M. Lentz
发明人： Elizabeth Castillo Martinez , Ray H. Baughman , Lee J. Hall , Mikhail Kozlov , Dawn E. Smith , Thaddeus Prusik , Carl M. Lentz
IPC分类号： C08F238/00 , G01D21/00 , C07C275/20 , C08F2/36
CPC分类号： C07C275/20 , C08F238/02 , G01N31/229
摘要： Solid polymerizable diacetylenic monomer compositions, including compositions co-crystallized from a diversity of solvent systems under diverse cooling conditions, can exhibit diffraction patterns associated with the color development reactivities of the compositions. High reactivity compositions are disclosed and high reactivity and low reactivity phases can be identified. A low angle powder X-ray diffraction peak can indicate the presence of one or more crystal phases in a composition. A fingerprint region can exhibit fingerprint patterns of diffraction peaks associated with different reactivities. Information about polymerization of the diacetylenic monomers is disclosed using 13C nuclear magnetic resonance (“NMR”) characterization. Diacetylenic monomer compositions useful in ambient condition indicators, for example time-temperature indicators are disclosed.
摘要翻译： 固体可聚合二炔单体组合物，包括在不同冷却条件下从各种溶剂体系共结晶的组合物可以显示与组合物的显色反应性相关的衍射图。 公开了高反应性组合物，并且可以鉴定出高反应性和低反应性相。 低角度粉末X射线衍射峰可以指示组合物中存在一个或多个结晶相。 指纹区域可以显示与不同反应性相关的衍射峰的指纹图谱。 使用13C核磁共振（NMR）表征公开了关于二乙炔单体的聚合的信息。 公开了用于环境条件指示剂的二乙炔单体组合物，例如时间 - 温度指示剂。
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公开(公告)号：US20120045837A1
公开(公告)日：2012-02-23
申请号：US13248254
申请日：2011-09-29
申请人： Thaddeus Prusik , Dawn Smith , Ray H. Baughman
发明人： Thaddeus Prusik , Dawn Smith , Ray H. Baughman
IPC分类号： G01N21/75
CPC分类号： C09D11/50
摘要： Indicator inks, indicators formed by printing or otherwise utilizing the inks and host products utilizing the indicators are disclosed. Reactivity-enhancing adjuvants stimulate enhanced thermal reactivity of diacetylenic or other indicator agents capable of responding to ambient thermal conditions with a visual change signaling an end point. The diacetylenic or other agents may be sensitive or relatively insensitive to ambient temperatures. Use of a reactivity-enhancing adjuvant provides a useful means for adapting the reactivities of indicator agents to the response characteristics of prospective host products, for example perishables such as vaccines or fresh fish and maturables such as fruit, cheese and wine. Some exemplary adjuvants include low-temperature polymerization initiators, for example methyl ethyl ketone peroxide and polymerization accelerators, for example cobalt compounds. Such initiators and accelerators can also be used in combination.
摘要翻译： 公开了指示剂油墨，通过使用指示剂印刷或以其它方式利用油墨和主体产品形成的指示剂。 反应性增强佐剂刺激能够响应于环境热条件的二乙炔或其他指示剂的增强的热反应性，其中以指示终点的视觉改变。 二乙炔或其它试剂可能对环境温度敏感或相对不敏感。 使用反应性增强佐剂提供了一种有用的方法，用于使指示剂的反应性适应预期宿主产物的反应特性，例如易腐食品，例如疫苗或鲜鱼以及可食用如水果，奶酪和葡萄酒。 一些示例性的助剂包括低温聚合引发剂，例如甲基乙基酮过氧化物和聚合促进剂，例如钴化合物。 这样的引发剂和促进剂也可以组合使用。
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7.发明授权Freeze indicators, flexible freeze indicators, combination indicators and manufacturing methods 有权冻结指标，灵活冻结指标，组合指标和制造方法公开(公告)号：US07891310B2
公开(公告)日：2011-02-22
申请号：US12500799
申请日：2009-07-10
CPC分类号： G01K3/005 , G01K3/04 , G01K11/06 , Y10S252/962
摘要： Freeze indicators providing a visual indication of exposure of the freeze indicator to a freezing or near-freezing temperature and their manufacture are disclosed. The freeze indicators employ colloidal dispersions as active elements and include flexible freeze indicators, freeze indicators protected against drying out and freeze indicators employing core shell composites, for example gold coated pigments as active indicator elements. Also disclosed are: a combination freeze indicator and threshold temperature indicator; a combination threshold indicator and cumulative temperature indicator; and three-way combination indicators that can provide indications of cumulative past temperature exposure, exposure to freezing temperatures and exposure to a temperature above a threshold.
摘要翻译： 公开了冻结指示器，其提供了将冷冻指示剂暴露于冷冻或接近冻结温度的视觉指示及其制造。 冻结指示剂使用胶体分散体作为活性元素，并且包括灵活的冷冻指示剂，防止干燥的冷冻指示剂和使用核心壳复合材料的冷冻指示剂，例如镀金颜料作为活性指示剂元素。 还公开了：组合冻结指示器和阈值温度指示器; 组合阈值指标和累积温度指标; 和三路组合指示器，可以提供累积过去的温度暴露，暴露于冷冻温度和暴露于高于阈值的温度的指示。
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公开(公告)号：US07571695B2
公开(公告)日：2009-08-11
申请号：US11750054
申请日：2007-05-17
IPC分类号： G01K11/12
CPC分类号： G01K3/005 , G01K3/04 , G01K11/06 , Y10S252/962
摘要： Freeze indicators providing a visual indication of exposure of the freeze indicator to a freezing or near-freezing temperature and their manufacture are disclosed. The freeze indicators employ colloidal dispersions as active elements and include flexible freeze indicators, freeze indicators protected against drying out and freeze indicators employing core shell composites, for example gold coated pigments as active indicator elements. Also disclosed are: a combination freeze indicator and threshold temperature indicator; a combination threshold indicator and cumulative temperature indicator; and three-way combination indicators that can provide indications of cumulative past temperature exposure, exposure to freezing temperatures and exposure to a temperature above a threshold.
摘要翻译： 公开了冻结指示器，其提供了将冷冻指示剂暴露于冷冻或接近冻结温度的视觉指示及其制造。 冻结指示剂使用胶体分散体作为活性元素，并且包括灵活的冷冻指示剂，防止干燥的冷冻指示剂和使用核心壳复合材料的冷冻指示剂，例如镀金颜料作为活性指示剂元素。 还公开了：组合冻结指示器和阈值温度指示器; 组合阈值指标和累积温度指标; 和三路组合指示器，可以提供累积过去的温度暴露，暴露于冷冻温度和暴露于高于阈值的温度的指示。
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9.发明授权公开(公告)号：US08529682B2
公开(公告)日：2013-09-10
申请号：US13248254
申请日：2011-09-29
申请人： Thaddeus Prusik , Dawn E. Smith , Ray H. Baughman
发明人： Thaddeus Prusik , Dawn E. Smith , Ray H. Baughman
CPC分类号： C09D11/50
摘要： Indicator inks, indicators formed by printing or otherwise utilizing the inks and host products utilizing the indicators are disclosed. Reactivity-enhancing adjuvants stimulate enhanced thermal reactivity of diacetylenic or other indicator agents capable of responding to ambient thermal conditions with a visual change signaling an end point. The diacetylenic or other agents may be sensitive or relatively insensitive to ambient temperatures. Use of a reactivity-enhancing adjuvant provides a useful means for adapting the reactivities of indicator agents to the response characteristics of prospective host products, for example perishables such as vaccines or fresh fish and maturables such as fruit, cheese and wine. Some exemplary adjuvants include low-temperature polymerization initiators, for example methyl ethyl ketone peroxide and polymerization accelerators, for example cobalt compounds. Such initiators and accelerators can also be used in combination.
摘要翻译： 公开了指示剂油墨，通过使用指示剂印刷或以其它方式利用油墨和主体产品形成的指示剂。 反应性增强佐剂刺激能够响应于环境热条件的二乙炔或其他指示剂的增强的热反应性，其中以指示终点的视觉改变。 二乙炔或其它试剂可能对环境温度敏感或相对不敏感。 使用反应性增强佐剂提供了一种有用的方法，用于使指示剂的反应性适应于预期宿主产物的反应特性，例如易腐食物例如疫苗或鲜鱼以及可食用如水果，奶酪和葡萄酒。 一些示例性的助剂包括低温聚合引发剂，例如甲基乙基酮过氧化物和聚合促进剂，例如钴化合物。 这样的引发剂和促进剂也可以组合使用。
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10.发明授权Crystallized diacetylenic indicator compounds and methods of preparing the compounds 有权结晶二乙炔指示剂化合物及其制备方法公开(公告)号：US08642807B2
公开(公告)日：2014-02-04
申请号：US13529605
申请日：2012-06-21
申请人： Ray H. Baughman , Lee J. Hall , Mikhail Kozlov , Dawn E. Smith , Thaddeus Prusik
发明人： Ray H. Baughman , Lee J. Hall , Mikhail Kozlov , Dawn E. Smith , Thaddeus Prusik
IPC分类号： C07C275/20 , G01K11/12 , G01D21/00
CPC分类号： G01K11/12 , C07C273/02 , C07C275/20 , C09B69/10 , G01K3/04 , G01N21/78 , G01N31/22 , G01N31/229
摘要： Crystallized diacetylenic compounds having certain crystallographic and other characteristics; diacetylenic compounds and mixtures crystallized from diacetylenic solutions; methods of preparing and identifying solvent systems for dissolving diacetylenic compounds; diacetylenic solutions; methods of recrystallizing diacetylenic compounds; crystals of 2,4-hexadiyn-1,6-bis(alkylurea) compounds; and ambient condition indicators and time-temperature condition indicators comprising crystallized diacetylenic compounds.
摘要翻译： 具有某些晶体学特性的结晶二炔化合物; 二乙炔化合物和从二乙炔溶液中结晶的混合物; 制备和鉴定溶解二乙炔化合物的溶剂体系的方法; 二乙酰溶液; 二乙炔化合物重结晶方法; 2,4-己二炔-1,6-双（烷基脲）化合物的晶体; 环境条件指标和包含结晶二乙炔化合物的时间 - 温度条件指标。
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