DE1048411B - Process for the production of condensation products - Google Patents

Description

Di-, tri-, tetra-, penta- or hexaoxethylaniline. Furthermore »5 when using formaldehyde also in aqueous form Oxalkyliemngsprodukte of the ToIu phase may also be mentioned, with all of the water being distilled off idins, xylidins, 2,6-diethyianilins, cyclohexyltoluidins.

Chloraniline and the 4 * Aminodiphynyläthcrs and both of compounds with aliphatically bound

its chlorination products. Other hydroxyl groups for oxyalkylation as well as compounds with aromatic amines are, for example, phenylenediamine; some ring systems are known to be associated with 4.4'-Diaminodiphenymethane, Triaminotriphenylmcthan, Formaldehyde are able to react. Connections with α-naphthylamine. ß-Naphthylamine and 1,8-diamino aliphatically bound hydroxyl groups form naphthalene. in the presence of acidic catalysts, polyacetals. So

The most suitable aldehydes are of the form, which is obtained, for example, in the reaction of hexanaldehyde called, for example, in aqueous solution, 35 diol with formaldehyde in the presence of acidic Katalyinsbesondcre But the high molecular weight polyhexamethylene formal is also used as a paraforma glue. will. Other suitable aldehydes are, for. B. chloral and also aromatic compounds such as Benzaldehyde. for example dimethylaniline with formaldehyde in the presence

Carrying out the reaction is just like that before reacting by hydrochloric acid. With a molar ratio of oommcn that the more detailed aroma 4 © 2: 1 are formed, defined compounds of the table compounds type with aliphatic hydroxyl groups of 4,4'-: dimethylamino] -diphenylmethane are formed.
brings together with the aldehyde and after adding the intended use as starting material

an acid catalyst heated, water dende aromatic compounds, the at least is split off and distilled off. The condensation contained two aliphatically bonded hydroxyl groups is expedient in an inert gas stream, about 45 offer the prerequisites for both possible reactions - carbonic acid or nitrogen. chains. It now became the surprising observation

Suitable acidic catalysts generally made in that upon the action of aldehydes Amounts of 0.1 to 5% are used, with the abovementioned compounds in the presence of In some cases, smaller or larger amounts of advantageous acidic catalysts are practically exclusively a core, are for example p-toluenesulfonic acid. Hydrochloric acid, linkage via methylene groups under extensive Phosphoric acid, sulfuric acid. Zinc chloride, oxalic acid Preservation of the aliphatically bound hydroxyl groups or formic acid. he follows.

The reaction can also be carried out in a solvent, depending on the proportions used.

dnrhrhren. where it is advantageous to stand in organic solution in this case low or high molecular weight condensate

Claims (3)

station products. Thus, when 2 moles of the aromatic compound are exposed to 1 mole of aldehyde, predominantly low-molecular products are formed, whereas when 1 mole of the aromatic compound is exposed to 1 mole or more of aldehyde, high-molecular-weight products are formed. Since water is released during the condensation, the desired degree of condensation can also be determined on the basis of the amount of water split off. Even the higher molecular, highly viscous condensation products have a hydroxyl content which, taking into account the amount of aldehyde used and the amount of water split off, almost corresponds to that of the starting components. The lower and higher molecular weight hydroxyl group-containing condensation products obtainable by the process are valuable starting components for the production of plastics. are mixed with 72 g of paraformaldehyde and, after adding 10 g of p-toluenesulfonic acid, heated to 80 to 90 ° C. for 2 hours with stirring and passing in carbonic acid. The water split off during this time is distilled off. A vacuum is then gradually applied and the temperature is increased to 120 to 130 ° C. in the course of 1 to 2 hours. After a total of 25 ecm of water has been split off, the condensation is interrupted. The resulting condensation product is a highly viscous yellow-red oil with an OH number of 269. Example 2 1076 g of tetraoxyethylaniline (4 mol), obtained from 372 g of aniline and 0.4 g of sodium and 704 g of ethylene oxide at 130 to ISO0C, are mixed with 140 g Paraformaldehyde mixed and, after adding 15 ecm of concentrated hydrochloric acid, condensed in the manner indicated in Example 1. The condensation is interrupted after the passage of 54 ecm of water. The condensation product that remains is a yellow, highly viscous oil with an OH number of 360. Example 3 results after 5 »/» hours of condensation at 90 ° C / 12 mm with elimination of 28 ecm of water, a viscous oil with an OH number of 347 and an acid number of 11.2. From 1076 g of tetraoxethylaniline and 145 g of paraformaldehyde in the presence of 40 g of phenylglycine, after 4 hours of condensation at 90 to 1003C 12 mm with elimination of 65 ecm of water, a yellow-red viscous oil with an OH number of 336 and an acid number of 5.6 is obtained. . IO EXAMPLE 5 If 538 g of tetraoxäthylanUin and 75 g of paraformaldehyde are reacted in the presence of 30 g of methylphenylglycine under the conditions given in Example 4, a viscous yellow-red oil with OH is formed after 4 hours of condensation at 90 ° C / 12 mm with elimination of 30 ecm of water -Number of 330 and an acid number of 1.2. If the methylphenylglycine is replaced by the same ao amount of anilinediacetic acid, 33 ecm of water are split off in 3 hours at 90 ° C / 12 mm. The condensation product obtained is a viscous oil with an OH number of 325 and an acid number of 22.4. »5 examples. If 538 g of tetraoxyethylaniline and 70 g of paraformaldehyde are reacted under the conditions given in Example 4 in the presence of 12 g of 5-aminobenzene-1,3-dicarboxylic acid, after a condensation period of 5 hours at 90 ° C./12 mm, 28 ecm of water is formed yellow-red viscous oil with an .OH number of 347 and an acid number of 8.4. If the 5-aminobenzoM, 3-dicarboxylic acid 3 $ is replaced by the same amount of m-aminobenzoic acid, 21 ecm of water are split off in 5 hours. The condensation product obtained is a viscous oil with an OH number of 364 and an acid number of 11.2. If the 12 g of 5-aminobenzoI-1,3-dicarboxylic acid are replaced by 5 g of m-sulfanuic acid, 20 ecm of water are split off in about 5 hours. The condensation product obtained is a viscous oil with an OH number of 364 and an acid number of 2.8. 742 g of hexaoxethyl-o-toluidine (2 mol) are condensed in the manner indicated above with 70 g of paraformaldehyde after adding 8 cm of concentrated hydrochloric acid. A dark-colored, highly viscous paste with an OH number of 316 is obtained. Example 4 53 bg of tetraoxethylaniline and 85 g of paraformaldehyde are gradually heated to 90.degree. C. in the presence of 75 g of N-phenylglycine while passing carbonic acid over it. After about an hour, the paraformachydrate went into $ s solution. When the vacuum is gradually applied, the water of condensation formed distills off with a simultaneous increase in the viscosity of the increasingly clearer melt. The elimination of water is complete after 2 hours at about 90 to 100 "C / 12 mm. A viscous yellow-red oil has formed which has an OH-ZaM of 294 and an acid number of 25. Water can be split off 43 under the specified conditions 538 g of tetraoxethylanUin and 75 g of paraformaldehyde reacted in the presence of 25 g of phenylglycine, according to patent α s si nc cn E: 1. Process citrus production of condensation products, characterized in that aromatic compounds are used at least once grouping 1 / CH ₁ -CH-OXHI II R / J. contained in the molecule, where R is hydrogen or a methyl group and η is an integer from I to 10 means, reacts with aldehydes in the presence of acidic catalysts. 2. The method according to claim I, characterized by the use of formaldehyde or paraformaldehyde as an aldehyde. 3. The method according to claim 1 and 2, characterized by the use of di-, tri-, tetra-, Penta- or Hexaoxäthylanilin from aromatic compound.