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.
一项基本上是单阶段反应的发现,其中可以将二取代
乙醇胺(即2,2'-取代-2-
氨基
乙醇)与卤代
甲烷和含有羰基的化合物(选自单酮和
苯甲醛组)在碱
金属氢氧化物的存在下反应,并在需要时在相转移催化剂的存在下,产生一种具有N-相邻C原子的碱
金属羟乙基
氨基
乙酸(“
HEAA”),在每个N-相邻C原子的一对或两对取代基可以环化。
HEAA可以通过矿酸的作用而环化,产生一种2-吗啉酮盐酸盐,其特点是在环上的N-相邻C原子上至少有三个取代基。所产生的2-吗啉酮可以还原为多取代
氨基醇。所产生的
氨基醇可以与烷基
磺酸环化,产生一种无法以其他方式制备的多取代吗啉。
氨基醇也可以烷基化,以产生具有多取代N-相邻C原子的双醚。如果
氨基醇被
甲烷磺酸酯化,将产生一种具有复数聚
乙烯基团的多取代
冠醚。上述
HEAA和相关化合物被用作新颖组合物中的紫外
光稳定剂,在其中,一个或多个
HEAA和相关化合物的少量但有效量被纳入,以产生对各种有机材料的紫外光降解的理想稳定化。