Bis-(alkylphenyl)-alkanecarboxylic acid hydrazides, their preparation and use
AssigneeHoechst Aktiengesellschaft
InventorsNorbert Mayer, Gerhard Pfahler, Hartmut Wiezer
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Abstract
Bis-(alkylphenol)-alkanecarboxylic acid hydrazides are obtained by reaction of bisphenol-alkanecarboxylic acid chlorides, azides, anhydrides or esters with hydrazine hydrate, at a temperature of from 5 to 200.degree. C. These hydrazides are excellent stabilizers for plastic materials, especially polyolefins.
Claims6
Compounds of the formula ##STR15## in which n is 1, 2 or 3;
- A and B represent together with the carbon atom separating them a cycloalkyl ring having from 5 to 12 carbon atoms;
- D is a chemical bond or a C.sub.1 to C.sub.3 -alkylene radical and
- R.sup.1 is H or a C.sub.1 to C.sub.4 -alkyl radical, while
- R.sup.2 is either (a) a hydrogen atom or (b) corresponding to the meaning of n, a mono-, bi- or tri-valent phosphorus containing radical having the structure:
- ##STR16## in which m is an integer of from 0 to 30, p is an integer of from 10 to 20, and x is H or OH, and in the case (b) A may also be H or C.sub.1 to C.sub.8 -alkyl and B may also be C.sub.1 to C.sub.8 -alkylene.
A process for the preparation of the phosphorus-containing compounds as claimed in claim 1, which comprises reacting esters of geminal bis-(tert.-butyl-4'-hydroxyphenyl)-alkylcarboxylic acids of the formula ##STR17## in which R.sup.1, A, B and D are as defined in claim 8, Y is an alkyl or alkylene radical having from 1 to 4 carbon atoms, and z is 1 or 2 corresponding to the valency of Y, with hydrazine hydrate, and subsequently reacting n moles of the hydrazides obtained with 1 mol of a tri-lower alkylphosphite or triphenyl phosphite and altogether 3--n moles of one or several members selected from the group consisting of aliphatic monoalcohols or beta-hydroxy alcohols having from 2 to 30 carbon atoms and monoamines having from 10 to 20 carbon atoms in the presence of catalytic amounts of tertiary amines or strong bases.
Dependencies are inferred from the claim text.