An essentially single stage reaction has been discovered in which a disubstituted ethanolamine, that is, a 2,2'-substituted-2-aminoethanol, may be reacted with a haloform and a carbonyl containing compound selected from the group consisting of monoketones and benzaldehyde, in the presence of an alkali metal hydroxide, and optionally in the presence of a phase transfer catalyst, to produce an alkali metal hydroxyethylaminoacetate ("HEAA") which has N-adjacent C atoms on which there are a total of at least three substituents (hence "polysubstituted"), and one or both pairs of substituents on each N-adjacent C atom may be cyclized. The HEAA may be cyclized by the action of a mineral acid to produce a 2-morpholone hydrochloride which is characterized by having a total of at least three substituents on the N-adjacent C atoms of the ring. The 2-morpholone so produced may be reduced to a polysubstituted aminodiol. The aminodiol so produced may be cyclized with an alkane sulfonic acid to yield a polysubstituted morpholine which could not otherwise have been made. The aminodiol may also be alkylated to produce diethers with polysubstituted N-adjacent C atoms. If the aminodiol is tosylated, a polysubstituted crown ether is produced with plural polyalkylene groups. The foregoing HEAA and related compounds are used as u-v light stabilizers in novel compositions in which a small but effective amount of one or more of the HEAA and related compounds is incorporated, in an amount sufficient to produce desirable stabilization against degradation by u-v light in a wide variety of organic materials.
发现了一种基本上的单步反应,其中二取代的
乙醇胺,即2,2'-取代的-2-
氨基
乙醇,可以与卤仿和选自单酮和
苯甲醛的含羰基化合物在碱
金属氢氧化物存在下反应,并可选择性地在相转移催化剂存在下反应,以产生具有N-相邻C原子上的至少三个取代基(因此称为“多取代”)的碱
金属羟乙基
氨基
乙酸酯(“
HEAA”),并且每个N-相邻C原子上的一个或两个取代基对可以环化。
HEAA可以通过
无机酸的作用环化,产生具有环的N-相邻C原子上的至少三个取代基的2-吗啉酮盐酸盐。产生的2-吗啉酮可以被还原为多取代的
氨基二醇。产生的
氨基二醇可以通过与烷基
磺酸反应环化,产生不能通过其他方式制备的多取代吗啉。
氨基二醇也可以被烷基化,产生具有多取代N-相邻C原子的
二醚。如果
氨基二醇被对
甲苯磺酰化,会产生具有多个聚亚烷基基团的多取代
冠醚。上述
HEAA及其相关化合物被用作新型组合物中的紫外线稳定剂,其中包含一种或多种
HEAA及其相关化合物的小而有效的量,足以在各种有机材料中产生对抗紫外线降解的理想稳定性。