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Publication numberUS1915922 A
Publication typeGrant
Publication dateJun 27, 1933
Filing dateMar 2, 1931
Priority dateMar 2, 1931
Publication numberUS 1915922 A, US 1915922A, US-A-1915922, US1915922 A, US1915922A
InventorsLudwig J Christmann, Jr David W Jayne
Original AssigneeAmerican Cyanamid Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Mothproofing
US 1915922 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

of the di-aryl substituted nyl, tolyl, xylyl, etc.

Patented June 21, 1933 PATENT OFFICE LUD'WIG J. OHBISTKANN, OF JERSEY CITY,

NEW; JERSEY, ASSIGNORS T0 AMERICAN ann'navm w. J'AYNE, m, or Emma,

CYAHAIID COIPANY, OF NEW YORK,

IOTHPBOOFING- Io Drawing.

loids areusually applied as a salt of a fatty.

acid dissolved in naphtha. The textile or garment to, be protected is saturated with this solution, the naphtha allowed to evaporate and the residue remaining serves as a repellent tc the insects. Many other sub-- stances have been proposed for this purpose. However, many of these compounds are rare chemicals and quite expensive. Cheapness and availability, as well as efiectiveness,are desired.

We have discovered a class of compounds which may be manufactured easily and cheaply and which are very efiective as moth repellents. This class of compounds consists guanidines of the formula-- 4 v RNH-O-NHR' I H i where R and R are aryl groups such as phe- Illustrative ofthe guanidines which we may use are di-xylyl guanidines. These may be made by the action of cyanogen chloride on the mixed xylidines. This reaction results in the formation of the guanidine hydrochloride from which the free guanidines may be separated. cost, the guanidines from the mixed 'xylidines are preferred, but if desired, the guanidine from a pure xylidine, for example, m-xylidine, may be used.

As an example of our parts of xylyl guanidine m'ercial mixed xylidines, acid, mix these together and stir into 250 arts of petroleum naphtha. This solution 1s then used for the im regnation of wool clothin a proportion 0 about 1 pound of invention we take 6 made from com- 4.7- parts of oleic resulting cloth is thus protecte From the standpoint of Application filed larch 2, 1931. Serial No. 518,679.

solution to 20 poimds to 49 pounds of wool. The naphtha is allowed to eva orate. The against the rava es of the insects.

It is obvious that the proportions used may be varied. Other solvents ma be used instead of petroleum naphtha. e ade of the petroleum naphtha may be varie to give any desired rate of evaporation. The guani dines may be used in the form of the salts of fatty'acids other than oleic, dissolved in other solvents or may be dissolved as the free base in. solvents. Other guanidines may be used instead of xyl l guanidines, for example, diphenyl guani ine, di-para-tolyl guanidine, di-benzyl guanidine, di-p-dimethyl anilino guanidine, a methyl a 7 diphenyl guanidine, di or napthyl guanidine and asymmetrical diphenyl guanidine, or mixtures thereof. These compounds are easily obtained, are non-volatile, stable to atmospheric conditions and are without toxic action to human beings when so used.

It will be obvious that our invention is susceptible of many other changes and variations in addition to those set forth, the scope of the invention only being limited by the appended claims.

We claim 1. The process of moth-proofing material which comprises treating it with a OOmPOBI- tion containing a fattyl acid salt of a substance having the fo owing general formulanNn-c-Nnw where R and R are aryl oups.

2. The process of mot -proofing material which comprises treating it with a composition containing a fatty acid salt of a di-aryl substituted guanidine.

3. The process of moth-p which comprises treating 1t guanidine.

4. The process which comprises tion containing a with a di-xylyl of moth-proofing material treating it with a com di-xylyl guanidine as t of oleic acid.

5. A moth-proofing composition comprisdi-ortho-tolyl guanidine,

roofing material masses in? e Meryl substitutecl guenidioe salt of 10. As a moth-proofing compmitioo e die ott acid dissolved in on orgenic solvent. xylylsubstituted guemidme.

6. mothroofin composition comprisll. As a moth-proofing composition a diinge, di-xyly gueni ine dissolved in on oriylfil substituted guemidme admixed with o & game solvent v or fatty acid. 7. A mothroofing composition compris n witness whereof, we have hereunto subing o di-xyly gummdine salt of oleic acid scribed our memes this 25th day of February olissolved in an organic solvent. 1931. I 8. Afibrous materiel cerrying e di-oryl LUDW'IG J. @HRJISTMANN. M substituted guenidine salt of e, fatty acid. DAVID W, JAYNE, Jo. 75

9. fibrous materiel carrying e, di-xylyl guemolinea 15 v to l to so l 5 45 i no st m 5&5 312@ $359 tee

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3349099 *Apr 8, 1965Oct 24, 1967Ciba Geigy CorpAminoaryl-guanylhydrazones
US3492407 *Nov 7, 1966Jan 27, 1970Bayer AgPest repelling compositions and methods of use
US4659739 *Feb 25, 1985Apr 21, 1987Dainippon Ink And Chemicals, Inc.Agricultural and horticultural guanidine-type fungicide and process for production thereof
US4709094 *Jul 10, 1986Nov 24, 1987State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonSigma brain receptor ligands and their use
US5262568 *Mar 4, 1991Nov 16, 1993State Of OregonTri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
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US5385946 *Feb 23, 1993Jan 31, 1995State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonAdministering hypotensive agents
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Classifications
U.S. Classification514/555, 554/104, 564/238, 8/196, 428/907, 424/403
Cooperative ClassificationY10S428/907, C07D401/12