DE1196373B - Process for the production of molded bodies, coatings or bonds - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. Cl .:

C08g

German class: 39 c-13

Number: 1196373

File number: S 74786IV d / 39 c

Filing date: July 12, 1961

Opening day: July 8, 1965

From Industrial and Engineering Chemistry, 48 (1956), P. 94 to 97 it is known that hydroxyl groups are the polyaddition of a system of epoxy compounds and accelerate amines. However, nowhere in this article does it appear that lactic acid is also can serve as an excellent accelerator.

Many compounds are already known for the formation of polyadducts from epoxies to form hard molded parts. One of these well-known groups are the lower polyvalent amines. However, these have a number of disadvantages, e.g. B. They are toxic and cause skin damage, while those obtained with this amine Products are too brittle for some purposes, especially at room temperature. Continue receiving one when using such amines for paints coatings, which often the so-called blooming effect demonstrate.

Another group of compounds, e.g. B. anhydrides of polybasic carboxylic acids, such as phthalic anhydrides, show the disadvantage that they form ester groups in the product when used. These ester groups can affect the chemical resistance of the polyadducts, especially the Resistance to alkali, harmful effects.

There are also amides already containing amino groups as a reaction component for epoxy compounds known. These compounds are obtained by dimerization or trimerization of an unsaturated one Fatty acid from drying oil, ζ. Β. Linseed oil fatty acid, and reacting the resulting polymers Acid with an aliphatic polyvalent amine such as ethylenediamine or diethylenetriamine. In some With regard to the polyadducts obtained with these compounds give better results, e.g. B. regarding the flexibility, however, the use of this connection has so far not been quite satisfactory. In In some cases, the slow polyadduct formation rate was a disadvantage. In addition the compatibility with the epoxy compounds was often insufficient at normal temperature.

There has also been a process for producing polyadducts by reacting an epoxy compound described with on average more than one epoxy group in the molecule, the epoxy compound with an amino compound containing primary and / or secondary amino groups in which the compound had a molecular weight of more than 300 and at least three hydrogen atoms, bonded to the nitrogen atom of the amino group, in the presence of a compound with a phenolic hydroxyl group has been implemented.

Although this method avoids some disadvantages.
Coatings or bonds

Applicant:

Shell Internationale Research Maatschappij

N.V., The Hague

Representative:

Dr.-Ing. F. Wuesthoff, Dipl.-Ing. G. Pulse and
Dipl.-Chem. Dr. rer. nat. E. Frhr. v. Bad luck man,
Patent Attorneys, Munich 9, Schweigerstr. 2

Named as inventor:

Brian John Carr, Staines, Middlesex;

Ralph Edward Stoltan, Tolworth, Surrey

(Great Britain)

Claimed priority:

Great Britain July 14, 1960 (24 552)

the earlier method, however, is too fast for some applications slowly, and often prevents the insolubility of the compound obtained with the phenolic group in more efficient polyadduct formation of the reaction mixture; in addition, the speed of implementation is difficult too brisk. The above disadvantages can be avoided by the method according to the invention.

The invention relates to a process for the production of moldings, coatings or bonds based on polyadducts by reacting epoxy compounds with more than one Epoxy group in the molecule with at least one amino compound, the primary or secondary amino groups contained, in the presence of accelerators, which is characterized in that it is used as an accelerator Lactic acid used.

Any epoxy compound that can be used as an epoxy compound in the process according to the invention is more as an epoxy group, are used, namely those with a molecular weight below 1200, especially below 600, preferred. The epoxy compound should preferably be liquid. Particularly Those epoxides which are derived from bisphenol or glycerol and have a molecular weight in the Range from 300 to 500 and min-

509 599/447

have at least 1.6 epoxy groups in the molecule. Examples of suitable liquid epoxides are the diglycidyl ethers of diphenylol propane and diglycidyl phthalate. Diphenylolpropane is particularly preferred derived epoxies.

As amino compounds containing primary or secondary amino groups, in the invention Method m-phenylenediamine, diaminodiphenylmethane and diethylenetriamine can be used. Further examples are the amine derivatives of long-chain fatty acids, adducts of amines and epoxidized ones oils or alkenes, especially condensation products of lower aliphatic polyamines, dimerized or trimerized fatty acids from drying oils, such as condensation products of dimerized ones Fatty acid of linseed oil with ethylenediamine.

The weight ratio of the amounts of epoxy compound to amino compound can be further within Limits vary, e.g. 90:10 to 10:90, especially 30:70 to 70:30 for polymeric amides. A particularly suitable ratio is 65:35.

The use of lactic acid as an accelerator reduces the pot life and accelerates the formation of polyadducts and allows an effective adjustment of the conversion speed. During the implementation of the process according to the invention, known additives such as fillers, pigments, Plasticizers, as well as other polymers, may be present. The plasticizer is preferably one of the Group of esters, especially dioctyl phthalate, used, generally in an amount of less than 100 parts by weight to 100 parts by weight of epoxy resin.

The products obtained according to the invention are moldings, coatings or adhesives. In the Carrying out the process for the production of surface coatings, the reaction can be carried out at room temperature take place, whereby the solvents usually used in painting technology are superfluous are. The products obtained by the process according to the invention are also not only suitable for Manufacture of cable sleeves, but also for the manufacture of layering material and glue.

The invention is illustrated by the following example:

example

100 parts by weight of diglycidyl ether of diphenylolpropane were mixed with 50 parts of a 50% solution of diamino-diphenylmethane in 8-butyrolactone and 10 parts of lactic acid. The mixture had a gel time of 90 minutes at 25 ⁰ C; The final deformation must take place within this gel time.

5 Without the addition of lactic acid, no polyaddition took place within 24 hours at this temperature.

The enormous technical progress that has been made with the

Replacement of phenol by lactic acid is clearly evident from the following experiment. So

ίο the time to gel decreases with 2 percent by weight lactic acid from> 360 to 114 and with 10 percent by weight still from 120 to 24 minutes.
The following comparison should serve to demonstrate the superior accelerating effect of lactic acid compared to phenol.

A basic mixture of 100 parts of diglycidyl ether of diphenylolpopane with a molecular weight was obtained of 380 and at least 1.9 epoxy groups

so in the molecule and 50 parts by weight of p, p'-diaminodiphenylmethane manufactured. 2.5 and 10 parts by weight of lactic acid were added to the basic mixture 100 parts by weight made up and the gel time measured. The following values were obtained:

TeMe
Lactic acid Gel time at 25 ° C
Minutes Parts
phenol Gel time at 25 ⁰ C
Minutes 2/100
5/100
10/100 114
44
24 2/100
5/100
10/100 360
300
120

Claims (1)

Claim: Process for the production of moldings, coatings or bonds based on Polyadducts by reacting epoxy compounds with more than one epoxy group in the Molecule with at least one amino compound that contains primary or secondary amino groups, in the presence of an accelerator, characterized in that as Lactic acid accelerator used. Considered publications: Indust. and Engng. Chem., 48, 1956, pp. 94 to 97; P a q u i n, epoxy compounds and epoxy resins, Berlin, 1958, pp. 483, 484. 509 599/447 6.65 ® Bundesdruckerei Berlin