FIELD: chemistry.
SUBSTANCE: invention relates to a mixture of polyetheramines based 1,3-dialcohols containing at least 90 % by weight, based on the total weight of the etheramine mixture, an amine of formula (I) and (II), and to a method for its preparation. Said etheramine mixture can be used as an additive to detergents and cleaning agents used, for example, for washing fabrics at low temperatures. In formula (I) and (II)
Formula (I),
Formula (II), R1–R12 is independently selected from H, C1-C5-alkyl, phenyl-C1-C5-alkyl, where at least one of R1–R6 and at least one of R7–R12 is different from H, where A1–A9 are independently selected from linear or branched alkylene containing from 3 to 10 carbon atoms, where Z1–Z4 are independently selected from OH, NH2, where at least one of Z1-Z2 and at least one of Z3-Z4 represents NH2, where R' and R'' are independently selected from alkylene containing from 2 to 6 carbon atoms, and where x≥1 and y≥1; and x1+y1 is in the range of 2 to 5 where x1≥1 and y1≥1, and wherein in said polyetheramine of formula (I) or formula (II), x+y is in the range of 3 to 8. Preferred is a mixture of etheramines containing at least 95 % by weight, based on the total weight of the etheramine mixture, amine of formula (I) and (II) with a degree of amination in the range from 60 % to 100 %. This method for obtaining the etheramine mixture containing at least 90 wt.%, based on the total mass of primary amines, based on the total mass of amine, includes stage a) the interaction of 1,3-diol of formula (III) with C3-C10 alkylene oxides, where the molar ratio of 1,3-diol to C3-C10 alkylene oxides range from 1:3 to 1:6, while in 1,3-diol of formula (III) (III), R1–R6 independently represent H, C1-C5-alkyl, phenyl-C1-C5-alkyl, and at least one group selected from R1–R6 is different from H, and step b) aminating alkoxylated 1,3-diols with ammonia. Preferably C3-C10 alkylene oxides are selected from the group consisting of propylene oxide, butylene oxide or a mixture thereof, or from the group consisting of 2-butyl-2-ethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2-methyl-2-phenyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-ethyl-1,3-hexanediol. Amination is carried out in the presence of a copper, nickel or cobalt containing catalyst. In this case, the catalytically active substance of the catalyst before its reduction with hydrogen includes oxygen compounds of aluminum, copper, nickel and cobalt, and in the range from 0.2 to 5.0 wt.% of oxygen compounds of tin when calculated as SnO.
EFFECT: resulting mixture of etheramines when added to known detergents significantly increases the effectiveness of the detergent when washing with a cycle at 30 °C, for example, cotton products with stains from grease, oil and traces of makeup, compared with the traditional detergents that do not contain branched polyethylene glycols with an amine ring.
14 cl, 16 tbl, 11 ex
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Authors
Dates
2019-01-28—Published
2014-03-27—Filed