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Publication numberUS3051616 A
Publication typeGrant
Publication dateAug 28, 1962
Filing dateMar 21, 1957
Priority dateMar 23, 1956
Publication numberUS 3051616 A, US 3051616A, US-A-3051616, US3051616 A, US3051616A
InventorsDrapal Othmar
Original AssigneeBayer Ag
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Mothproofing agents
US 3051616 A
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Description  (OCR text may contain errors)

3,651,616 MOTHPROOFIN G AGENTS Othmar Drapal, Leverkusen, Germany, assignor to Farbenfabriken Bayer Aktiengesellschaft, Leverkusen, Germany, a corporation of Germany No Drawing. Filed Mar. 21, 1957, Ser. No. 647,471 Claims priority, application Great Britain Mar. 23, 1956 8 C. (Cl. 167-37) The present invention relates to and has as its objects mothproofing compositions and a process for making textiles resistant to the attack of moths and more generally keratin textile pests.

Most of the known mothproofing agents, for example those based on tr-iphenylmethane derivatives or derivatives of aryl nreas, dissolve only at boiling temperature and require comparatively large quantities of water. The dissolving process takes, therefore, much time and energy, thus being cumbersome for the intended use of the products.

It has now beenfound that compounds of the general formula wherein X is a hydrogen atom, a low molecular weight alkyl radical, an aryl-O--, aryl-S- or aryl-NH group, and R and R' stand for a hydrogen atom or an alkyl radical, are excellently suited to improve substantially or expedite the solubility of the aforesaid active substances. Examples of such solubility-improving compounds are phenylurethanes, tolylurethane, xylylurethane, and the corresponding thiourethanes, phenylurea, phenyl-methylurea, tolylurea, xylylurea, and the corresponding thioureas, benzamide, toluamide, N-methylbenzamide, N,N-dimethylbenzamide, acetamide, N-methylacetamide, formamide or dimethylformamide. Those compounds, however, are given by way of illustration only without limiting this invention in any way.

Particularly effective of this class are the simple aromatic carboxylic acid amides.

As stated above the most suitable mothproofing agents which may be combined with the afore mentioned compounds are those ones derived from triphenylmethane or from arylureas as they are known e.g. under the trademarks Eulan or Mitin. Compounds of that type are known e.g. from US. Patents No. 1,707,181, No. 2,376,930, and No. 2,719,852.

The solubility-improving compounds are applied for example by adding the agent in question in quantities of 10 to 50 percent to the initial active substance or mixtures of active substances, and dissolving them in a little water. This clear concentrated solution can then be diluted with water in any proportion.

Mothproofing of textiles proceeds by known methods e.g. by floating wool or woollen textiles in a 1 to 10% aqueous solution while heating near to the boiling point. The time which is required for giving full protection depends widely upon the known mothproofing agent which has been used together with the inventive solubilisation compounds. Normally heating for about one hour should be suflicient for efiective mothproofing.

The following examples are given to illustrate the invention.

Example 1 :1 part of the methylene ether of 2,2.-dihydroxy- 3,5,3,5',4"-pentachloro-triphenylmethane-2 sulphonic acid is thoroughly mixed with 1 part of monophenylurea.

This mixture dissolves clear after pouring over it only 3,5l,616 Patented Aug. 28, 1962 4 to 5 times its amount of boiling water, and can be tect them permanently from damage caused by keratin pests.

Example 2 1 part of the urea derivative from 4,4'-dichloro-2- amino-diphenyl ether and 3,4-dichloroaniline of the following formula s 0 Na NH-O own-@m is intimately mixed with 1 part of benzamide.

' This mixture also dissolves after pouring on it 5 times its amount of boiling Water to give a clear solution which can be mixed with water in any proportion.

The solutions are unaffected by the addition of salt or acid and remain stable upon boiling. They are suitable for the protection of textiles against keratin pests.

Example 3 1 part of 2,2-dihydroxy 3,5,3',5',4" pentachlorotriphenylmethane-Z-sulphonic acid is intimately mixed with 1 part of benzamide. The solution of this mixture exhibits the same properties as described in the preceding examples and is used for protection against keratin pests.

Example 4 1 part of 2,2-dihydroxy-3,5,3',5-tetrachlorotriphenylmethane- 2"-sulphonic acid is mixed intimately with 1 part of thiourea. This mixture is dissolved in 5 parts of boiling water. The mixture is boiled for further 2 to 5 minutes and then may be diluted with water in any proportion. Woolen yarn which is brought into a 5% hot aqueous solution of the above mixture for 1 hour gets permanently protected against keratin pests such as moths.

Example 5 1 part of 2,2-diethoxy-3,5,3,5',4"-pentachlorot1iphenylmethane-2"-sulphonic acid is intimately mixed with 1 part of dimethylformamide. A solution of this mixture exhibits the same properties as those described in the foregoing examples. If this mixture is diluted to a concentration of 5% and used in an amount of 3% active substance referred to the amount of textiles to be protected then the latter ones get full protection after boiling them for 1 hour with said solution in a neutral or weak acidic medium.

Example 6 1 part of 2,2'-diallylhydroxy-3,5,3',5,4"-pentachlor0- triphenylmethane-2"-sulphonic acid is intimately mixed with 1 part of acetic acid amide. The solution of this mixture shows the same effectiveness as that one of the foregoing example and may also successfully be used against moths and other keratin pests.

I claim:

1. A dry composition comprising a compound selected from the group consisting of triphenylmethanes and diphenyl ethers, said triphenylmethanes and said diphenyl ethers being mothproofing agents, and a member selected from the group consisting of benzamide and phenylurea.

2. An aqueous composition comprising water, a compound selected from the group consisting of triphenylmethanes and diphenyl ethers, said triphenylmethanes and said diphenyl ethers being mothproofing agents, and a member selected from the group consisting of benzamine and phenylurea.

3. A dry composition comprising a triphenylrnethane mothproofing agent and phenylurea.

4. A dry composition comprising a diphenyl ether mothproofing agent and benza-mide.

5. A dry composition comprising a triphenylmethane mothproofing agent and benzamide.

' 6. An aqueous composition comprising Water, a triphenylmethane mothproofing agent and phenylurea.

7. An aqueous composition comprising water, a diphenyl ether mothproofing agent and benzamide.

, 8. An aqueous composition comprising water, a triphenylmethane mothproofing agent and benzarnide.

References Cited in the file of this patent UNITED STATES PATENTS 1,707,181 Weiler et al. Mar. 26, 1929 2,032,890 Schoeller et al Mar. 3, 1936 2,166,120 Bousquet July 18, 1939 2,299,834 Martin et a1 Oct. 27, 1942 2,376,930 Martin et a1. May 29, 1945 4 2,671,748 Crooks Mar. 9, 1954 2,719,852 Retter Oct. 4, 1955 FOREIGN PATENTS 290,364 Great Britain May 14, 1928 277,033 Great Britain May 17, 1928 325,847 Great Britain Feb. 28, 1930 462,972 Great Britain Mar. 15, 1937 614,018 Great Britain Dec. 8, 1948 491,677 Canada Mar. 31, 1953 OTHER REFERENCES Frear: A Catalogue of Insecticides and Fungicides, vol. 1,page 27, col. 1, No. 185-951-1021, col. 2, No. 185-1011 and 185-1021 (1947).

Schefian et al.: The Handbook of Solvents, pages 310, 407-408, 1953.

Chisholm: US. Dept. Agr. Bureau of But. and Plant Quar. Bull. E-742, pages 1-12, page 6 relied on, February 1948.

Haynes: Chem. Trade Names and Commercial Synonyms, 2nd. ed., page 272, October 1955.

Patent Citations
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US1707181 *Mar 13, 1928Mar 26, 1929Ig Farbenindustrie AgCondensation product from p-halogenated phenolic compounds and aldehydes
US2032890 *Nov 16, 1931Mar 3, 1936Schering Kahlbaum AgComposition of matter
US2166120 *Aug 12, 1937Jul 18, 1939Du PontInsecticidal composition
US2299834 *Dec 20, 1940Oct 27, 1942Firm Of J R Geigy A GHalogen containing acylaminosulphonic acids and their manufacture
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US2671748 *May 18, 1950Mar 9, 1954Parke Davis & CoComposition of matter
US2719852 *May 24, 1952Oct 4, 1955Bayer AgTriphenylmethane derivatives
CA491677A *Mar 31, 1953Ciba LtdStable, supersaturated aqueous solutions of saccharide derivatives of the suprarenal cortical hormone series and process of making same
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4879275 *May 27, 1988Nov 7, 1989Nelson Research & Development Co.Penetration enhancers for transdermal delivery of systemic agent
US4902676 *Sep 29, 1986Feb 20, 1990Nelson Research & Development Co.Compositions comprising N,N-dialkylalkanamides
US4920101 *Sep 30, 1987Apr 24, 1990Nelson Research & Development Co.For enhancing penetration of physiologically active agents through skin or other membranes
US5034386 *Aug 17, 1988Jul 23, 1991Whitby Research, Inc.Fungicides
US5204339 *Aug 6, 1990Apr 20, 1993Whitby Research, Inc.Penetration enhancers for transdermal delivery of systemic agents
U.S. Classification514/721, 514/772, 514/788
International ClassificationA01N37/18
Cooperative ClassificationA01N37/18
European ClassificationA01N37/18