US2200603A - Method for the improving of goods - Google Patents

Description

Patented May 14,1940

UNITED STATES PATENT OFFICE METHOD FOR THE IMPROVING OF GOODS of Switzerland No Drawing. Application July 6, 1938, Serial No. 217,720. In Germany July 6, 1937 10 Claims.

It has been found that or the protection of goods from attacks of vermin those quaternary ammonium compounds are particularly suitable which contain on the nitrogen atom no less than two aryl-methyl groups, at least one of which is to bear one or several hydroxyl groups which maybe eventually alkoxylated or esterified.

' The compounds suggested for the treatment of goods for improving purposes are of the general formula An AT-CH3ITC [is-A110" In this formula Ar and Ari mean aromatic residues such as phenyl, diphenyl, naphthyl, tetra hydronaphthyl, octahydro-anthracyl and the like. R1 and R2 mean any organic-residues e. g. aliphatic residues such as methyl-, ethyl-, hydroxyethyl-, dimethyl-amino-ethyl-, propyl-,

isopropyl-, benzyl-groups and the like; R1 and R2 pounds in which the aromatic residues are substituted by higher alkylor cyclo-alkyl-groups are most suitable. 7

Such compounds are e. g. dimethyl-benzyl- (2'- hydroxy-E-chloro-benzyl) -ammonium chloride, 5,5-dihydroxye2,2'-dichloro-dibenzy1-piperidinium chloride, 5-chloro-2-hydroxybenzyl-a-menaphthyl-diethyl-ammonium chloride, 4,6324,- tetrachloro 1 hydroxydibenzyl-diethyl-ammonium chloride,- 5 -bromo- 2 -methyl-4chloro1- hydroxy-dibenzyl-piperidinium chloride. They are obtained by converting amines containing at least one arylmethyl group into-quaternary ammonium compounds in a way usual in itself,v

whereat the materials are to be selected in such a. manner, that there exists in the quaternary ammonium compound at least 2 arylmethyl groups, at least one of which is substituted by one phenolic hydrozwl group or by its functional derivatives such as esteror other groups. But I may likewise proceed by starting with the amines which already possess two arylmethyl groups of the characterized sort and then converting these into the quaternary compounds e. g. by converting them with alkylating or aralkylating agents. Finally it is also practicable to react primary and secondary amines containing no arylmethyl groups with compounds which while forming the quaternary ammonium compounds give oil the arylmethyl groups of the characterizod type.

The compounds suggested for the refining of goods can be applied either alone or mixed with one another and eventually with an addition of other preserving agents. I may proceed e. g. in such a manner that I soak or moisten or sprinkle the goods to be preserved with solutions of said compounds in organic liquids. With products inclining to crystallizing I am in a position to prevent the efiiorescing of the ammonium compounds in choosing an appropriate solvent or mixture of solvents or also additional materials such as higher alcohols, cyclic acetones or acetals and the like.

Moreover these compounds may be used in emulsions or dispersions or where they are easily soluble in water-An aqueous solutions to be applied in the treatment of the goods in a way similar to a dyeing process.

It may sometimes be advisable to co-employ some special wettingand emulsifying-agents to secure a uniform penetration of the goods.

I may bring the goods into intimate contact with the new preserving agents also by powdering them. In the powdering process I may make use of dredging boxes, rolling casks and the like. When it is not advisable to use my novel preservation per se in the form of a powder, I can make firm powdery preparations out of same and powdered adsorption materials such as infusorial earth, talcum, wood-flour, bleaching earth, starch, etc.

My new preserving agents may be applied in the presence of other compounds such as acids,

' salts, mordants, dyestufis and the like, whereby their efil'ciency or their sticking-power will be enhanced or other properties improved.

The treatment can be performed at room temperature as well as at higher temperatures.

Due to the simplicity of the present method the treatment is possible not only in the manufacture and working-up of goods but also in the household and incleansing-establishments such as chemical laundries, further in washing with benzine or with other organic solvents and particularly with non-inflammable ones.

I I may also apply, besides the aforesaid hydrohalic acids, other acids such as hydrofluosilicic acid, perchloric acid, hydrocyanic acid, acyle phosphoric acid, sulfuric acidor also organic acids e. g. carbonic acids, sulfonic acids, etc, to form salts with my quaternary bases.

The claimed products may serve for the refining of wool, textile materials, natural or artificial fibres, iurriery, hair, feathers, leather, paper or, respectively, products or masses containing such materials. Their preserving power is so high that small amounts are sufficient to produce very remarkable effects.

Example I Furs to be preserved against vermin and particularly against moths are powdered with a mi):- ture consisting of 93 weight parts of talcum and 7 weight parts of 5-bromo-2-rnethylr-chloro-lhydroxy-dibenzyl-piperidinium chloride.

Example 2 W001, becomes unassailable by vermin when treated with three times the amount of a 0.2%- aqueous-alcoholic solution of 4,6,3',e'-mtrachlorol-hydroxy-dibenzyl-diethyl-ammonium-chloride.

Example 3 Textiles are thoroughly moistened, as indicated in Example 2, with a 0.5%-aqueous solution of dimethy1-benzyl-(2-hydroxy-5-chlorobenzyD-ammonium-chloride and subsequently treated in a diluted aqueous solution of potassium chlorate, whereby the difficultly soluble perchlorate of the quaternary base is precipitated upon the goods to be preserved against vermin.

I claim:

1. Process for the protection of goods from vermin characterized by treating the goods with quaternary ammonium compounds of the general formula An ..r-cn,-1 -cHT-Anon in which Ar and Ari mean an aromatic residue, An means an anion and R1 and R: stand for any organic residue.

2. Process for the protection of goods from vermin characterized by treating the goods with quaternary ammonium compounds of the general formula Air: A l. C Hr-f-C H;Ar;-O H

R; R: in which Ar and Ari mean an aromatic residue, An means an anion and R1 and R2 stand for organic residue, which jointly form a ring with the N-atom.

3. Process for the protection of goods from vermin characterized by treating the goods with soluble quaternary ammonium compounds of the general formula in which Ar and Ari. meanan aromatic residue,

An means an anion and R1 and R2 stand for any organic residue and reacifing the soluble quaternary ammonium compounds on the goods with salts producing dimcultly soluble salts with the quaternary ammonium compounds by double decomposition.

4. A vermin-proofing agent for goods comprising a quaternary ammonium compound or" the general formula in which Ar and Ari mean any substituted aromatic residue, An means an anion oi the group consisting of Cl, Fl, Br and I and R1 and R2 stand for organic residue jointly forming a ring with the N-atom.

6. A vermin-proofing agent for goods comprising a quaternary ammonium compound of the general formula.

in Hg in which Ar and Ari mean a substituted aromatic residue of the group consisting of hydroxyl-, halogen-, nitro-, amino-, alkyland cycloallzyl substituted aromatic residues, An means an anion and B1 and R2 stand for any substituted aliphatic residue, the hydrogen atoms of the CH; groups being substituted by allryl residues.

'7. A vermin-proofing agent for goods containing 5-bromo-2-methy1--chloro-i-hydroXy-dibenzyl-piperidiniumchloride.

8. A vermin-proofing agent for goods containing 4, G, 3, F-tetrachloro-lhydroxy-ciibenzyl-diethyl-ammonium chloride.

9. A vermin-proofing agent for goods containing dimethyl-benzyl-(Z-hydroxy-fi-chiorcbenzyll ammoniumchloride.

l0. Vermin-prooied goods of the nature of furs, feathers, textiles and other fibrous materials and the like, having their vermin-proof characteristics imparted by incorporating in said goods a compound of the formula.

in which Ar and Ari mean aromatic groups, An means a halogen and R1 and R2 stand for an organic radical.

WINFRID HENTRICH.