# US 4,399,268 A · Process for preparing moulded bodies and coatings

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- Number: US 4,399,268 A
- Document ID: US4399268A
- Status: Granted
- Kind: A
- Application number: 06/276,687
- Filed: 1981-06-23
- Granted: 1983-08-16
- Earliest claimed: 1980-06-24
- Assignees: Hoechst Aktiengesellschaft
- Inventors: Wilhelm Becker; Herbert Hubner; Manfred Marten
- Web page: https://patentgrep.com/patent/US4399268A

## CPC

- C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C03C 17/38: at least one coating being a coating of an organic material
- C08G 59/50: Amines
- C08G 59/62: Alcohols or phenols
- C08G 59/64: Amino alcohols
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C03C: CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A process for the preparation of molded bodies and coatings which comprises reacting at least one epoxy compound containing more than one 1,2-epoxy group per molecule alone or in combination with at least one monoepoxide, with at least one substituted amine of formula ##STR1## which contains no free phenols and in which R.sup.1 is hydrogen or methyl, R.sup.2 is a radical of at least one of formulae ##STR2## and R.sup.3 is hydrogen, a hydroxy group, a carboxylic group or methyl, said amine (I) having been obtained by reaction of a substance selected from the group consisting of at least one xylylenediamine, and hydrogenation product thereof in the form of bis-(aminomethyl)-cyclohexanes according to one of the following processes with (a) a hydroxybenzaldehyde or a hydroxyacetophenone in a first step to form a Schiff's base and followed by a hydrogenation of said base in a second step to form a compound of formula (I), (b) a dimethylaminomethylphenol being free from phenols or with the corresponding cresol derivative or with at least one Mannich base, containing no free phenols, but derived from at least one phenol, formaldehyde and such primary monoamines, the aliphatic .alpha.-carbon atom of which is bound to at least two aliphatic carbon atoms of hydrocarbon groups, and/or substitution products thereof the substituent of which is inert towards the reaction, the dimethylamine or the primary monoamine component of the Mannich base being to a large extent or completely split off, to yield a compound of formula (I), and (c) with at least one phenol-hexamethylenetetramine condensation product of at least one of formulae ##STR3## said products containing no free phenols, to form a compound of formula (I) under splitting off ammonia.

## Claims

### Claim 1

A process for the preparation of molded bodies and coatings which comprises reacting at least one epoxy compound containing more than one 1,2-epoxy group per molecule alone or in combination with at least one mono-epoxide, with at least one substituted amine of formula
being free from other phenols and in which R.sup.1 is hydrogen or methyl, R.sup.2 is a radical of at least one of formulae ##STR11## and R.sup.3 is hydrogen, a hydroxy group, a carboxylic group or methyl, which amine has a content of phenolic OH-- groups of at least 6.3% by weight and is reacted in an amount being at least equivalent to the epoxy groups in the epoxy resin and at most in an excess of up to 50 mol%, said amine (I) having been obtained by reaction of (A) a substance selected from the group consisting of least one xylylenediamine, and hydrogenation product thereof in the form of bis-(aminomethyl)-cyclohexanes according to one of the following processes with (Ba) a hydroxybenzaldehyde or a hydroxyacetophenone in a first step to form a Schiff's base and followed by a hydrogenation of said base in a second step to form a compound of formula (I), (Bb) a dimethylaminomethylphenol or with the corresponding cresol derivative or with at least one Mannich base, each of them being free from other phenols but derived from at least one phenol, formaldehyde and such primary monoamines, the aliphatic .alpha.-carbon atom of which is bound to at least two aliphatic carbon atoms of hydrocarbon groups, and/or substitution products thereof, the substituent of which is inert towards the reaction, splitting off and therefore substituting completely or to a large extent the dimethylamine group or the primary monoamine component of the Mannich base by the component (A) to yield a compound of formula (I), and (Bc) at least one phenol-hexamethylenetetramine condensation product of at least one of the formula ##STR12## said products being free from other phenols, splitting off and therefore substituting ammonia by component (A) to form a compound of formula (I).

### Claim 2 (depends on 1)

A process as claimed in claim 1, wherein the substitution reaction of component (A) in the steps (Bb) and (Bc) is effected at a temperature of from 100.degree. to 200.degree. C.

### Claim 3 (depends on 2)

A process as claimed in claim 2, wherein the temperature is in the range of from 120.degree. to 160.degree. C.

### Claim 4 (depends on 1)

A process as claimed in claim 1, wherein the substituted amine (I) is used as a hardener per se or in solution and has a content of phenolic OH-groups of at least 6.7% by weight.

### Claim 5 (depends on 1)

A process as claimed in claim 1, wherein the reaction of the epoxy compounds with the amines of formula (I) is performed at a temperature of at least -5.degree. C.

### Claim 6

A process for the preparation of molded bodies and coatings which comprises reacting at least one epoxy compound containing more than one 1,2-epoxy group per molecule alone or in combination with at least one mono-epoxide, with at least one substituted amine of formula ##STR13## being free from other phenols and in which R.sup.1 is hydrogen or methyl, R.sup.2 is a radical of at least one of formulae ##STR14## and R.sup.3 is hydrogen, a hydroxy group, a carboxylic group or methyl, said amine (I) having been obtained by reaction of (A) a substance selected from the group consisting of at least one xylylenediamine, and hydrogenation product thereof in the form of bis-(aminomethyl)-cyclohexanes according to one of the following processes with (Ba) a hydroxybenzaldehyde or a hydroxyacetophenone in a first step to form a Schiff's base and followed by hydrogenation of said base in a second step at 50 to 100 bar H.sub.2 to form the compound of formula (I), (Bb) a dimethylaminomethylphenol or with the corresponding cresol derivative or with at least one Mannich base, each of them being free from other phenols but derived from at least one phenol, formaldehyde and such primary monoamines, the aliphatic .alpha.-carbon atom of which is bound to at least two aliphatic carbon atoms of hydrocarbon groups, and/or substitution products thereof, the substituent of which is inert towards the reaction, splitting off and therefore substituting completely or to a large extent the dimethylamine group or the primary monoamine component of the Mannich base by the component (A) at a temperature of from 100.degree. to 200.degree. C. to yield a compound of formula (I), and (Bc) at least one phenolhexamethylenetetramine condensation product of a molar ratio of 3:1 to 6:1 of at least one of the formulae ##STR15## said products being free from other phenols, splitting off and therefore substituting ammonia by component (A) at a temperature of from 100.degree. to 200.degree. C. to form a compound of formula (I) wherein the amines of formula (I) are reacted in an amount being at least equivalent to the epoxy groups in the epoxy resin and at most in an excess of up to 50 mol-%, wherein said amine (I) is used as a hardener per se or in solution and has a content of phenolic OH-groups of at least 6.7% by weight and the reaction of the epoxy compounds with the amines of formula (I) is performed at a temperature of at least -5.degree. C.