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    Thermooxidative stabilization of polyolefins with an oxo-piperazinyl-triazine and a phosphorous acid ester
    2.
    发明授权
    Thermooxidative stabilization of polyolefins with an oxo-piperazinyl-triazine and a phosphorous acid ester 失效
    聚烯烃与氧代 - 哌嗪基 - 三嗪和亚磷酸酯的热氧化稳定化

    公开(公告)号：US5278209A

    公开(公告)日：1994-01-11

    申请号：US888950

    申请日：1992-05-26

    申请人： George Kletecka ,  John T. Lai

    发明人： George Kletecka ,  John T. Lai

    IPC分类号： C08K5/49 ,  C08K5/3492 ,  C08K5/524 ,  C08K5/527 ,  C08L23/02 ,  C08K5/52

    CPC分类号： C08K5/524 ,  C08K5/34926 ,  C08K5/527

    摘要： Only two symmetrical stabilizers in a polyolefin or copolymer thereof, provide thermooxidative ("TO") or antioxidative ("AO") stability. One is an arylphosphite or arylfluorophosphite; the other is a monomolecular tri-substituted triazine in which each of three chlorine atoms on a trihalo-s-triazine is substituted with a piperazinone in which the N atom in the 4-position is alkylated. Only a trace amount of phosphite, at least 0.01 phr but less than 0.1 phr, is used so that the ratio of the piperazinone-substituted stabilizer to ester is greater than 1; additional phosphite has no noticeable effect. The trace amount of phosphite has a surprising booster effect, giving the stabilized composition excellent TO stability. Articles thermoformed from the stabilized polyolefin or copolymer thereof may be used under the hood or the dash of a vehicle, and, in containers for packaging goods, all of which articles are subject to TO degradation even if they are not subject to ultraviolet light degradation.

    摘要翻译： 在聚烯烃或其共聚物中只有两种对称稳定剂提供热氧化（“TO”）或抗氧化（“AO”）稳定性。 一种是芳基亚磷酸酯或芳基氟亚磷酸酯; 另一种是单分子三取代三嗪，其中三卤代三嗪的三个氯原子中的每一个被其中4-位的N原子烷基化的哌嗪酮取代。 仅使用痕量的亚磷酸酯，至少0.01phr，但小于0.1phr，使得哌嗪酮取代的稳定剂与酯的比例大于1; 另外亚磷酸盐没有明显的效果。 痕量的亚磷酸酯具有惊人的助剂效果，使得稳定的组合物具有优异的TO稳定性。 从稳定化的聚烯烃或其共聚物中热成型的制品可以在发动机罩或车辆的冲击下使用，并且在用于包装货物的容器中，即使它们不经历紫外线光降解，所有这些制品都会被劣化。

    Process for making alkylated polyalkylenepolyamines by selective alkylation
    3.
    发明授权
    Process for making alkylated polyalkylenepolyamines by selective alkylation 失效
    通过选择性烷基化制备烷基化聚亚烷基多胺的方法

    公开(公告)号：US5270471A

    公开(公告)日：1993-12-14

    申请号：US966933

    申请日：1992-10-27

    申请人： John T. Lai ,  Pyong-Nae Son

    发明人： John T. Lai ,  Pyong-Nae Son

    IPC分类号： C07D241/08 ,  C07D403/12 ,  C07D403/14 ,  C08G73/06 ,  C08K5/3492 ,  C07C209/26 ,  C07D211/58

    CPC分类号： C07D403/12 ,  C07D241/08 ,  C07D403/14 ,  C08G73/0644 ,  C08K5/34926

    摘要： A branched chain polyalkylene polyamine ("PAPA") having plural amine groups, including a secondary amine group intermediate terminal primary amine groups one of which is hindered, and having at least two carbon atoms between each group, is selectively reductively alkylated with a ketone. The reaction provides a convenient method for selectively reductively alkylating a PAPA having a hindered primary amine group, the method comprising contacting the PAPA with hydrogen and the ketone in the presence of a catalytically effective amount of a Group VIII metal on a catalyst support, at a pressure in the range from about 500-1000 psi and a temperature in the range from about 50.degree. C. to about 200.degree. C. for a period of time sufficient to preferentially alkylate the unhindered amine primary terminal amine group. The alkylation proceeds essentially without alkylating either the sterically hindered terminal primary amine group or the intermediate unhindered secondary amine group.

    摘要翻译： 具有多个胺基的支链聚亚烷基多胺（“PAPA”）被选择性地用酮还原烷基化，包括其中一个受阻的仲胺基中间体末端伯胺基和每个基团之间具有至少两个碳原子。 反应提供了选择性还原烷基化具有受阻伯胺基团的PAPA的方便方法，该方法包括在催化剂载体上在催化有效量的第Ⅷ族金属存在下，使PAPA与氢和酮接触， 压力范围为约500-1000psi，温度范围为约50℃至约200℃，持续足以优先烷基化未取代的胺伯氨基末端胺基团的时间。 烷基化基本上不进行空间位阻末端伯胺基团或中间体未阻聚的仲胺基团的烷基化。

    Process for methylating a hindered nitrogen atom in a polysubstituted diazacycloalkan-2-one
    4.
    发明授权
    Process for methylating a hindered nitrogen atom in a polysubstituted diazacycloalkan-2-one 失效
    甲基化多取代二氮杂环烷-2-酮中的受阻氮原子的方法

    公开(公告)号：US5013836A

    公开(公告)日：1991-05-07

    申请号：US439408

    申请日：1989-11-21

    申请人： John T. Lai

    发明人： John T. Lai

    IPC分类号： C07D241/08 ,  C07D241/38 ,  C07D243/08 ,  C07D243/14 ,  C07D245/04

    CPC分类号： C07D241/38 ,  C07D241/08 ,  C07D243/08 ,  C07D243/14 ,  C07D245/04

    摘要： The difficulty of methylating a hindered piperidinyl, piperazinyl, or diazepinyl group with an Eschweiler-Clarke ("E-C") procedure without using a large molar excess (more than double) of formaldehyde is surprisingly found to be non-existent in the case of a diazacycloalkan-2-one group with a hindered N.sup.4 - or N.sup.5 -atom of its NH group which is to be methylated. The N.sup.4 - or N.sup.5 -atom of a polysubstituted diazacycloalkan-2-one group ("DCA") is substantially stoichiometrically converted even when a conventional E-C procedure is starved of HCHO, that is, with a much smaller molar excess of formaldehyde than deemed necessary. The effective molar ratio of NH groups: HCHO in the starved E-C process is in the range from 1:1 to 1:1.5, in the presence of enough formic acid to function both as reactant and solvent not only for a DCA-containing complex amine ("starting amine") to be methylated, but also for the methylated amine (product). Such a starting amine may have one or more DCA substituents which, in turn, may be connected to any other structure. Because this process is starved of at least HCHO, and usually both HCHO and HCOOH, it is referred to herein as the "starved E-C process". Upon completion of the reaction any excess HCOOH is neutralized with aqueous alkali, and the product separates from the reaction mass. Though the starting amine is often substantially soluble in water, it usually becomes substantially insoluble after it is methylated. Less than 5% of product is lost in the aqueous wash.

    摘要翻译： 令人惊讶地发现，使用Eschweiler-Clarke（“EC”）方法使受阻哌啶基，哌嗪基或二氮杂基团甲基化难以使用大量摩尔过量（超过两倍）的甲醛，在以下情况下是不存在的： 二氮杂环烷-2-酮基，其被甲基化的NH基的受阻的N4-或N5-原子。 多取代二氮杂环烷基-2-酮基（“DCA”）的N4-或N5-原子即使在常规EC方法中饥饿HCHO时也是基本上化学计量转换的，即甲醛摩尔过量比认为必要的少得多 。 在饥饿的EC过程中，NH基团：HCHO的有效摩尔比在1:1至1:1.5的范围内，在足够的甲酸存在下，作为反应物和溶剂不仅用于含DCA的络合胺 （“起始胺”）进行甲基化，也可用于甲基化胺（产物）。 这种起始胺可以具有一个或多个DCA取代基，其又可以连接到任何其它结构。 因为这个过程至少有HCHO，而且通常都是HCHO和HCOOH，所以这里被称为“饥饿的E-C过程”。 反应完成后，任何过量的HCOOH用碱水溶液中和，产物与反应物质分离。 尽管起始胺通常基本上可溶于水，但是甲基化后通常变得基本上不溶。 在水洗中少于5％的产品丢失。

    Alkylated polyalkylenepolyamines, substituted oxo-piperazinyl-triazines and UV light stabilized compositions
    5.
    发明授权
    Alkylated polyalkylenepolyamines, substituted oxo-piperazinyl-triazines and UV light stabilized compositions 失效
    烷基化聚亚烷基多胺，取代的氧代 - 哌嗪基 - 三嗪和UV光稳定的组合物

    公开(公告)号：US4722806A

    公开(公告)日：1988-02-02

    申请号：US721270

    申请日：1985-04-09

    申请人： John T. Lai ,  Pyong N. Son

    发明人： John T. Lai ,  Pyong N. Son

    IPC分类号： C07D241/08 ,  C07D403/12 ,  C07D403/14 ,  C08G73/06 ,  C08K5/3492 ,  C09K15/22

    CPC分类号： C07D403/12 ,  C07D241/08 ,  C07D403/14 ,  C08G73/0644 ,  C08K5/34926

    摘要： A branched chain polyalkylenepolyamine ("PAPA") amine having plural amine groups including a secondary amine group intermediate terminal primary amine groups and having at least two carbon atoms between each amine group, is reductively alkylated with a ketone to provide a PAPA alkylated only at an unhindered primary amine group. A preselected degree of steric hindrance at amine groups near each end of the chain enables cyclization by the `ketoform synthesis` by reaction with a ketone in such a manner as to form a polysubstituted piperazinone ("PSP") ring which includes N atoms of proximate primary and secondary amine groups of the alkylated PAPA. The PSP so formed may then be reacted with a reactive triazine ring so that a PSP substituent is linked to the triazine ring through a single N atom and at least two C atoms, to form a 2-oxo-piperazinyl-triazine ("PIP-T"). Oligomers of the PIP-T may be prepared. The PIP-T compounds are excellent stabilizers against ultraviolet (uv) light degradation in light-sensitive synthetic resinous materials. In combination with particular hindered phenols PIP-T compounds are found to provide better antioxidant properties than that obtained as the theoretical additive effect of the PIP-T and the hindered phenol, separately.

    摘要翻译： 具有多个胺基的支链聚亚烷基多胺（“PAPA”）胺包括仲胺基中间体末端伯胺基并且在各个胺基之间具有至少两个碳原子的胺被酮还原烷基化以提供仅在 不受阻碍的伯胺基团。 在链的每个端部附近的胺基上的空间位阻的预选程度使得能够通过与酮的反应通过“酮基形成合成”进行环化，从而形成多取代的哌嗪酮（“PSP”）环，其包括N个邻近的 烷基化PAPA的伯胺和仲胺基。 然后可以使如此形成的PSP与反应性三嗪环反应，使得PSP取代基通过单个N原子和至少两个C原子与三嗪环连接，形成2-氧代 - 哌嗪基 - 三嗪（“PIP- T“）。 可以制备PIP-T的低聚物。 PIP-T化合物是光敏合成树脂材料中抗紫外线（UV）光降解的优良稳定剂。 与特定的受阻酚组合发现PIP-T化合物分别提供比作为PIP-T和受阻酚的理论添加剂效果获得的更好的抗氧化性能。

    Synthesis of polyamines and mixture formed thereby, of diprimary polyalkylene polyamines with disubstituted N-adjacent terminal carbon atom(s)
    6.
    发明授权
    Synthesis of polyamines and mixture formed thereby, of diprimary polyalkylene polyamines with disubstituted N-adjacent terminal carbon atom(s) 失效
    由多取代的N相邻末端碳原子形成的多胺和由此形成的混合物的二元多聚亚烷基多胺的合成

    公开(公告)号：US4698446A

    公开(公告)日：1987-10-06

    申请号：US880845

    申请日：1986-07-01

    申请人： John T. Lai ,  Pyong N. Son

    发明人： John T. Lai ,  Pyong N. Son

    IPC分类号： C07C85/11

    CPC分类号： C07C209/34

    摘要： A nitroamine is formed from an aliphatic amine reactant + a nitroalkane + an aldehyde with better conversion, and faster, if the aldehyde is added last, and gradually, so as not to form an alkanolamine intermediate with the aldehyde as in the prior art reactions. In particular, a diamine such as ethylene diamine (EDA) has the unique ability, even among diprimary amines, to react with nitroalkane, to form a salt intermediate to which is added an essentially solvent-free aldehyde such as paraformaldehyde to produce a reaction product consisting essentially of a mixture of (i) a mononitrodialkylenediamine with a disubstituted N-adjacent terminal C atom and (ii) a dinitrotrialkylenediamine with each N-adjacent terminal C atom being disubstituted; and the mixture is obtained in an yield of at least 90 mol %.

    摘要翻译： 硝酰胺由脂肪族胺反应物+硝基烷烃+醛转化而成，如果最后加入醛，则逐渐加入，以便不像现有技术的反应那样与醛形成链烷醇胺中间体。 特别地，二胺如乙二胺（EDA）具有独特的能力，甚至在二胺中与硝基烷烃反应形成盐中间体，向其中加入基本上无溶剂的醛如多聚甲醛以产生反应产物 基本上由（i）单硝基二亚烷基二胺与二取代的N-邻近末端C原子的混合物组成，和（ii）二硝基三亚烷基二胺，其中每个N-邻近末端C原子被二取代; 以至少90摩尔％的收率得到混合物。

    Polysubstituted .alpha.-aminoacetamides
    9.
    发明授权
    Polysubstituted .alpha.-aminoacetamides 失效
    多取代的α-氨基乙酰胺

    公开(公告)号：US4500662A

    公开(公告)日：1985-02-19

    申请号：US427347

    申请日：1982-09-29

    申请人： John T. Lai

    发明人： John T. Lai

    IPC分类号： C07D211/58 ,  C07D295/15 ,  C08K5/20 ,  C07C103/50 ,  C07C103/727 ,  C07D211/00

    CPC分类号： C07D295/15 ,  C07D211/58

    摘要： Polysubstituted .alpha.-aminoacetamides of the formula ##STR1## wherein R.sup.1 is tert-alkyl; R.sup.4 is alkyl, phenyl, substituted phenyl, cycloalkyl, piperidinyl, tetraalkylpiperidinyl or an alkylene (.alpha.-aminoacetamide). These compounds are prepared by first reacting an .alpha.-haloacetamide with a base to form an .alpha.-lactam intermediate which in turn is reacted with a primary amine. The compounds are useful as stabilizers of polymeric materials against ultraviolet light degradation.

    摘要翻译： 式IMAMA的多取代α-氨基乙酰胺，其中R1是叔烷基; R4是烷基，苯基，取代的苯基，环烷基，哌啶基，四烷基哌啶基或亚烷基（α-氨基乙酰胺）。 这些化合物通过首先使α-卤代乙酰胺与碱反应形成α-内酰胺中间体而制备，所述α-内酰胺中间体又与伯胺反应。 这些化合物可用作抗紫外线降解的聚合材料的稳定剂。