三(壬苯基)亚磷酸酯 | 16784-72-8

• 物质功能分类: 催化剂及助剂 - 聚合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 三(壬苯基)亚磷酸酯
• 中文别名: 防老剂TNP；三(壬苯基)亚磷酸盐；亚磷酸三(2-壬基苯基)酯；苯酚,2-壬基-,1,1',1''-亚磷酸；三(壬基苯基)亚磷酸酯；抗氧化剂-1178；亚磷酸三壬基苯酯；三(壬基酚)亚磷酸酯；三(壬基苯酚)亚磷酸酯
• 英文名称: tri-(nonylphenyl) phosphite
• 英文别名: tris (nonylphenyl) phosphite；tris(nonylphenyl1)phosphite；Tris(nonylphenyl) phosphite；tris(2-nonylphenyl) phosphite
• CAS: 16784-72-8；26523-78-4
• 化学式: C₄₅H₆₉O₃P
• 分子量: 689.015
• InChiKey: WGKLOLBTFWFKOD-UHFFFAOYSA-N

物化性质

• 沸点：
  >360 °C(lit.)
• 密度：
  0.99 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 溶解度：
  苯（微量）、氯仿（微量）、甲醇（微量）
• 物理描述：
  COLOURLESS VISCOUS LIQUID.
• 颜色/状态：
  Clear liquid
• 熔点：
  6 °C (pour point), OECD Guideline 102 (Melting point / Melting Range)
• 蒸汽压力：
  0.058 Pa at 25 °C (0.000435 mm Hg), extrapolated from measured data at higher temperatures
• 稳定性/保质期：

  Chemical stability: Stable under recommended storage conditions.

• 自燃温度：
  440 °C
• 粘度：
  6000 mPa.s (dynamic) at 25 °C (OECD Test Guideline 114 (Viscosity of Liquids))

计算性质

• 辛醇/水分配系数(LogP)：
  19.3
• 重原子数：
  49
• 可旋转键数：
  30
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

代谢

食品接触塑料和橡胶可能含有多种化学物质，如单体、寡聚物、添加剂、聚合物和添加剂的降解产物以及杂质。其中，双酚A、壬基酚、邻苯二甲酸苄基丁酯、苯乙烯寡聚物和羟基化苯并苯酮据报道具有雌激素活性。在本研究中，测试了与食品接触塑料和橡胶相关的其他化学物质及其由S9混合物诱导的代谢物对酵母双杂合分析的雌激素活性。在150种化学物质中，有10种化学物质如双(4-羟基苯基)甲烷、4-环己基酚、4-苯基酚、4,4'-异丙基二酚烷基磷酸盐、两种类型的苯乙烯化酚(包括单型)、三(壬基苯基)磷酸盐、2,2'-二羟基-4-甲氧基苯并苯酮、2-羟基-4-甲氧基苯并苯酮和2,4-二苯基-4-甲基-1-戊烯，它们的代谢物以及另外6种化学物质如2-(苯甲基)酚、苯乙烯化酚(二型和三型)、1-(N-苯基氨基)萘、4-叔丁基苯基水杨酸酯、壬基酚乙氧基化物和2-甲基-6-叔丁基苯酚的代谢物显示出雌激素活性。它们都含有酚基团在其化学结构中，或者通过水解或代谢容易形成。然而，与食品接触塑料和橡胶相关的绝大多数化学物质及其代谢物并未显示出任何雌激素活性。

Food contact plastics and rubbers possibly contain many kinds of chemicals such as monomers, oligomers, additives, degradation products of polymers and additives, and impurities. Among them, bisphenol A, nonylphenol, benzylbutyl phthalate, styrene oligomers and hydroxylated benzophenones have been reported to possess estrogenic activities. In this study, other chemicals related to food contact plastics and rubbers, and their metabolites induced by the S9-mixture were tested for their estrogenic activities using the yeast two-hybrid assay. Among the 150 chemicals, 10 chemicals such as bis(4-hydroxyphenyl) methane, 4-cyclohexylphenol, 4-phenylphenol, 4,4'-isopropylidenediphenol alkylphosphite, two type of styrenated phenol (including mono type), tris(nonylphenyl) phosphite, 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone and 2,4-diphenyl-4-methyl-1-pentene, their metabolites and the metabolites of 6 other chemicals, such as 2-(phenylmethyl) phenol, styrenated phenol (di and tri type), 1-(N-phenylamino)naphthalene, 4-tert-butylphenylsalicylate, nonylphenol ethoxylates and 2-methyl-6-tert-butylphenol, displayed estrogenic activities. All of them contained a phenol group in their chemical structures or formed one easily by hydrolysis or metabolism. However, most of the chemicals related to food contact plastics and rubbers, and their metabolites did not show any estrogenicity.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

三(壬基苯基)亚磷酸酯是一种无色液体，具有微不足道到低的水溶性以及适中的蒸气压。三(壬基苯基)亚磷酸酯的工业用途包括：塑料制品制造、塑料包装材料生产、未覆膜薄膜和片材制造（作为稳定剂）、树脂和合成橡胶制造以及轮胎制造。人类暴露和毒性：一项日本研究发现，大多数PVC包装膜和手套中检出了三(壬基苯基)亚磷酸酯的衍生物。PVC包装膜在市场上广泛使用，因此许多种类的食品受到了污染。其中，鱼片或肉馅含有高水平的该物质。2000年，制造商自愿改变了其成分，日本的所有包装膜不再含有壬基酚。在日本，对双酚A、壬基酚和邻苯二甲酸二(2-乙基己基)酯的暴露量已显著减少，人们也更加关注食品接触物品的安全性。关于这种化合物的人类数据没有其他可用的信息。动物研究：美国环保署赞助的危险性筛查得出了以下LD50值：大鼠皮肤>2000 mg/kg，兔皮肤>2000 mg/kg，大鼠口服19500 mg/kg，大鼠腹腔注射>1000 mg/kg。关于这种化合物的动物数据没有其他可用的信息。

IDENTIFICATION AND USE: Tris(nonylphenyl)phosphite is a clear liquid with negligible to low water solubility and moderate vapor pressure. The industrial uses of Tris(nonylphenyl)phosphite include: plastics product manufacturing, plastic packaging materials production, unlaminated film and sheet manufacturing (as a stabilizer); resin and synthetic rubber manufacturing, and tire manufacturing. HUMAN EXPOSURE AND TOXICITY: A single Japanese study detected a derivative of tris (nonylphenyl) phosphite in most PVC wrapping films and gloves. PVC wrapping film was extensively used in markets, thus many kinds of foods were contaminated. Among them, fillet or minced fish and meat contained it at high levels. In 2000, manufacturers voluntarily changed their composition and all wrapping films in Japan no longer contain nonylphenol. In Japan, the exposure to bisphenol A, nonylphenol and DEHP have been significantly reduced and people also have more concerns with the safety of food contact articles. No other human data was available for this compound. ANIMAL STUDIES: USEPA sponsored hazard screenings yielded the following LD50's: rat dermal of > 2000 mg/kg, rabbit dermal of > 2000 mg/kg, rat oral of 19500 mg/kg, rat intraperitoneal of > 1000 mg/kg. No other animal data was available.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者向前倾或将其置于左侧（如果可能的话，头部向下），以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W TKO /SRP: "保持开放"，最低流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格氏液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/毒物A和B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/其他毒性信息/ 在20世纪90年代后半期，报告了许多内分泌干扰物出现在食品接触物品和婴儿玩具中。本文描述了双酚A、壬基酚、邻苯二甲酸盐、苯乙烯二聚体和三聚体及其转变。双酚A发现在聚碳酸酯餐具、奶瓶和罐头食品的环氧树脂涂层中，因此也出现在罐装食品和饮料中。由于消费者拒绝使用，聚碳酸酯现在在日本仅少量用于餐具或奶瓶。罐头制造商改变了他们的涂层材料为低双酚A树脂或PET薄膜，并自愿将其迁移限制在5或10纳克/毫升以下。壬基酚发现在大多数PVC包装薄膜和手套中。它是由一种氧化剂，三(壬基苯基)亚磷酸盐产生的。PVC包装薄膜在市场上广泛使用，因此许多种类的食品受到了污染。其中，鱼片或碎鱼和肉含有高水平的壬基酚。在2000年，制造商自愿改变了它们的成分，日本的所有包装薄膜都不再含有壬基酚。邻苯二甲酸二(2-乙基己基)酯(DEHP)发现在PVC手套中，这污染了便当和医院膳食。政府在2000年禁止这些手套用于所有食品接触用途，此外，含有DEHP的其他PVC食品接触物品在2002年被禁止用于接触脂肪食品。DEHP也发现在2002年被禁止的PVC玩具中。苯乙烯二聚体和三聚体发现在PS产品中，这些产品在烹饪后会迁移到杯装面条中。它们没有发生变化。在日本，双酚A、壬基酚和DEHP的暴露量已显著减少，人们对食品接触物品的安全性也更为关注。

/OTHER TOXICITY INFORMATION/ A number of endocrine disruptors have been reported in food contact articles and baby toys mainly during the second half of the 1990s. Bisphenol A, nonylphenol, phthalates, styrene dimers and trimers, and their transision are described in this article. Bisphenol A was found in polycarbonate tableware, nursing bottles and the epoxy resin coating of cans, therefore, it was also found in the canned foods and drinks. Polycarbonate is now only slightly used for tableware or nursing bottles in Japan because consumers refused them. The can manufacturers changed their coating material to the low bisphenol A resin or PET films and voluntarily regulate its migration limit to under 5 or 10 ng/ml. Nonylphenol was found in most PVC wrapping films and gloves. It was generated from an oxidant, tris (nonylphenyl) phosphite. PVC wrapping film was extensively used in markets, thus many kinds of foods were contaminated. Among them, fillet or minced fish and meat contained it at high levels. In 2000, manufacturers voluntarily changed their composition and all wrapping films in Japan no longer contain nonylphenol. Di(2-ethylhexyl) phthalate (DEHP) was found in PVC gloves, which contaminated packed lunches and hospital meals at high levels. The government prohibited these gloves for all food contact use in 2000, moreover, other PVC food contact articles containing DEHP were prohibited for contact use with fatty foods in 2002. DEHP was also found in PVC toys which was prohibited in 2002. Styrene dimers and trimers were found in PS products, which migrated into cupped noodles after cooking. No changes have been made in them. In Japan, the exposure to bisphenol A, nonylphenol and DEHP have been significantly reduced and people also have more concerns with the safety of food contact articles.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1

制备方法与用途

用途：聚合物热稳定剂。

反应信息

• 作为反应物：
  描述：

  、 、 三(壬苯基)亚磷酸酯 、 抗氧剂168 、 亚磷酸二[2,4-二叔丁基-6-甲基苯基]乙基酯 、 生成 亚磷酸三苯酯
  参考文献：
  名称：

  Phenol free stabilization of polyethylene film

  摘要：

  本发明提供了一种用于在熔融加工操作期间稳定热塑性聚烯烃的工艺。本发明的稳定剂配方是“无酚”配方，必须含有至少一种芳基单膦酸酯和至少一种双膦酸酯。本发明的工艺特别适用于聚乙烯薄膜的制造。

  公开号：

  US07361703B2
• 作为试剂：
  描述：

  苯乙烯 、 萜品油烯 、 乙基苯 、 、 、 丙烯酸 、 过氧化乙酸叔丁酯 、 Neodecanoate 在 tert-butyl 、 1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯 、 三(壬苯基)亚磷酸酯 、 丁酮 、 resultant polymer 作用下， 以 丁酮 为溶剂， 反应 26.5h， 以in a vacuum oven, to yield 660 grams of rubber-modified styrene-acrylic acid graft copolymer的产率得到5-苯基戊烷-2,4-双酸
  参考文献：
  名称：

  Thermoplastic polyblend compositions

  摘要：

  由热塑性氯乙烯共聚物和热塑性共聚物组成的聚合物混合物具有有用的性能，尤其是在负载下有用的热变形温度。共聚物最好是橡胶改性的接枝共聚物，其中包括至少一种乙烯基芳香单体，丙烯酸或甲基丙烯酸或两者，以及可选的至少一种可共聚的单体。

  公开号：

  US04456733A1

文献信息

• Diol-functionalized antioxidant and process for preparation thereof
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：US20040192969A1

  公开（公告）日：2004-09-30

  Diol-functionalized antioxidants and the process for the preparation thereof are disclosed and have the general formula (I): 1 wherein: R 1 is tert-butyl and R 2 is C 1 to C 8 linear or branched alkyl. The invention also pertains to a process for their preparation. Which comprises: Reacting a halo functionalized antioxidant having the general formula (II): 2 wherein: R 1 is tert-butyl and X is bromide (Br) with a diol having general formula (IV): 3 wherein R 2 is C 1 to C 8 linear or branched alkyl.

  二醇功能化抗氧化剂及其制备方法被披露，并具有通式 (I)： 1 其中： R 1 是叔丁基，R 2 是C 1 至C 8 的直链或支链烷基。 本发明还涉及它们的制备过程。 其包括： 将具有通式 (II) 的卤素功能化抗氧化剂： 2 其中： R 1 是叔丁基，X 是溴化物 (Br) 与具有通式 (IV) 的二醇反应： 3 其中 R 2 是C 1 至C 8 的直链或支链烷基。
• XANTHENE-BASED COMPOUND AND PHOTOSENSITIVE RESIN COMPOSITION COMPRISING SAME
  申请人：LG CHEM, LTD.

  公开号：US20200262807A1

  公开（公告）日：2020-08-20

  The present specification provides a compound represented by Chemical Formula 1, a colorant composition, a resin composition, a photosensitive material, a color filter and a display device comprising the same.

  当前规格书提供了一种由化学公式1表示的化合物，一种着色剂组合物，一种树脂组合物，一种光敏材料，以及包含该化合物的彩色滤光器和显示设备。
• OXIME ESTER PHOTOINITIATORS
  申请人：BASF SE

  公开号：US20180208583A1

  公开（公告）日：2018-07-26

  Compounds of the formulae (I) or (II) wherein X is A is O, S, NR 5 or CR 16 R 17 ; R 1 is for example hydrogen or C 1 -C 20 alkyl R 2 is for example hydrogen, C 1 -C 20 alkyl or C 6 -C 20 aryl R 5 for example is C 1 -C 20 alkyl; R 7 , R 8 , R 9 , R 10 and R 11 for example independently of each other are hydrogen. C 1 -C 20 alkyl, halogen, CN or NO 2 ; Ar 1 is for example unsubstituted or substituted C 6 -C 20 aryl, C 3 -C 20 heteroaryl, C 6 -C 20 aroyl, C 3 -C 20 heteroarylcarbonyl or or Ar 1 is Ar 2 is for example phenylene, all of which are unsubstituted or substituted M is for example unsubstituted or substituted C 1 -C 20 alkylene Y is a direct bond, O, S, NR 5 or CO; Z 1 is for example O or S; Z 2 is a direct bond, O, S or NR 5 ; and Q is CO or a direct bond.

  公式(I)或(II)的化合物 其中 X是 A是O, S, NR 5 或CR 16 R 17 ; R 1 例如是氢或C 1 -C 20 烷基 R 2 例如是氢, C 1 -C 20 烷基或C 6 -C 20 芳基 R 5 例如是C 1 -C 20 烷基; R 7 , R 8 , R 9 , R 10 和R 11 例如彼此独立是氢. C 1 -C 20 烷基, 卤素, CN或NO 2 ; Ar 1 例如是不取代或取代的C 6 -C 20 芳基, C 3 -C 20 杂芳基, C 6 -C 20 芳酰基, C 3 -C 20 杂芳基甲酰基或 或Ar 1 是 Ar 2 例如是苯基, 所有这些都不取代或取代 M例如是不取代或取代的C 1 -C 20 亚烷基 Y是直接键, O, S, NR 5 或CO; Z 1 例如是O或S; Z 2 是直接键, O, S或NR 5 ; 和 Q是CO或直接键。
• [EN] STERICALLY HINDERED AMINE STABILIZERS<br/>[FR] STABILISANTS D'AMINES À ENCOMBREMENT STÉRIQUE
  申请人：BASF SE

  公开号：WO2010142572A1

  公开（公告）日：2010-12-16

  The instant invention pertains to hindered amine compounds having at least two nitrogen atoms with different basicity. One part is substituted on the N-atom by alkoxy moieties and the other part is substituted on the N-atom by a hydroxy-alkyl moiety. These materials are particularly effective in stabilizing polymers, especially thermoplastic polyolefins, against the deleterious effects of oxidative, thermal and actinic radiation. The compounds are also particularly effective in stabilizing acid catalyzed and ambient cured coatings systems.

  这项瞬时发明涉及具有至少两个氮原子且碱度不同的受阻胺化合物。其中一部分在N原子上被烷氧基团取代，另一部分在N原子上被一个羟基-烷基基团取代。这些材料在稳定聚合物方面特别有效，尤其是热塑性聚烯烃，可以抵御氧化、热和光辐射的有害影响。这些化合物在稳定酸催化和环境固化的涂层系统方面也特别有效。
• Mixtures composed or monocarboxy-functionalized dialkylphosphinic acids, their use and a process for their preparation
  申请人：Maas Wiebke

  公开号：US20070213436A1

  公开（公告）日：2007-09-13

  The invention relates to mixtures composed of monocarboxy-functionalized dialkylphosphinic acids and of further components, which comprise A) from 98 to 100% by weight of monocarboxy-functionalized dialkylphosphinic acids of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are identical or different and, independently of one another, are H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and/or phenyl, X and Y are identical or different and, independently of one another, are H, Li, Na, K, or NH 4 , and B) from 0 to 2% by weight of halogens, where the entirety of the components always amounts to 100% by weight.

  该发明涉及由单羧基功能化二烷基膦酸和进一步组分组成的混合物，其中包括 A) 公式（I）中的单羧基功能化二烷基膦酸，其占98至100重量％ 其中R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，R 6 和R 7 相同或不同，并且彼此独立地为H，甲基，乙基，正丙基，异丙基，正丁基，异丁基，叔丁基和/或苯基， X和Y相同或不同，并且彼此独立地为H，Li，Na，K或NH 4 ， 和 B) 卤素，其占0至2重量％， 其中所有组分的总和始终为100重量％。