US1955207A - Mothproofing agent - Google Patents

Mothproofing agent Download PDF

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US1955207A
US1955207A US618341A US61834132A US1955207A US 1955207 A US1955207 A US 1955207A US 618341 A US618341 A US 618341A US 61834132 A US61834132 A US 61834132A US 1955207 A US1955207 A US 1955207A
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soluble
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US618341A
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Stotter Hermann
Hermann Theodor
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IG Farbenindustrie AG
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IG Farbenindustrie AG
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds

Definitions

  • The-present invention relates to a process 01' protecting materials against attack by textile pests and tothe'compositions employed therein.
  • mothiprooflng agents generally consist of arylsulio'nic acid amides of the general 10 formula: I
  • R1 and R2 stand. for hydrogen or a radical selected from the group consisting of alkyl radicals, aryl and aralkyl, and wherein all nuclei may further contain a substituent selected from the group consisting of hydroxyhalogen-, alkyl-, aryl-, alkylacidy1amino-, arylacidylamino-,. sulionic acidand carboxylic acid groups.
  • These compounds are highly active moth proofing agents, and, furthermore, excellently protectl wool, feathers, hair and the like also against the attack by other important textile pests, such as anthrenus Iasciatus, attagenus japonicus or attagenus piceus ol. Thereby they difier from other moth proofing agents, such as chlorinated naphthalenes, cinchona alkaloids and esters of phosphoric 'acid which are effective against moths, but ineffective against these textile pests.
  • R1, Ra, Ra means similar or dissimilar radicals selected from the group consisting of amide, such as the
  • arylsultonic acid allryl, aryl and aralkyl radicals which may contain substituents selectedfrom the group consisting of halogen (Cl, Br.) and alkoxy (QCHa, OCaHs), are very easily soluble in benzine, carbon tetrachloride, trichlorethylene and other organic solvents. Therefore, such mixtures can be used in the customary dry cleaning solvents for protecting the articles mentioned above against attack by moths or other textile pests.
  • These new mixtures generally represent colorless or faintly colored oils.
  • the quantity of the active components to be applied for protecting materials against textilepests may vary within wide limits.
  • For the mixture we generally use about two parts by weight of phosphoric acid ester, such as'the diethylbutylglycolphosphate, and one part by weight of an arylsulfonic acid 3,4-dichlorobenzenesulfomethylamide.
  • the new compositions may be applied in any of the known manners.
  • the intestinn be dissolved in benzine and sprayed on the materials to be protected or the same can be soaked with the solution or otherwise moistened therewith.
  • Example 1 -Wool, feathers or hair are. treat ed in a benzine solution of the mixture containing 2 parts of 3,4-dichlorobenzene-sulfomethylamide of the formula H O1G0:.N/
  • Example 4 The goods are treated with a trichloroethylene solution of 1 part of 3,4-dichlorobenzenesulfo 2 methylbenzeneamide (melting point 110 C.) in 0.5 part of triethylphosphate and 1 part of diethylbutylglycolphosphate.
  • Example 5 The goods are treated with a carbon tetrachloride solution of 1 part of 3.4-dichlorobenzenesulfamide (melting point 136 C.) and 2 parts of triethylphosphate.
  • Example 6 The protecting solution consists of trichlorethylene containing a mixture of 1 part of dichlorobenzenesulfodimethylamide (melting point 128 C.) and 1.5 parts of triethylphosphate.
  • Example 7 The protecting solution consists of benzine containing a mixture of 1 part of 3.4 dichlorobenzenesulfodiethylamide (melting point 58 C.) and 1.5 parts of tri-isoamylphosphate.
  • Example 8 The protecting solution consists of benzine containing a mixture of 1 part of 3,4 dichlorobenzenesulfodibutylamide (melting point 56 C.) and 1.5 parts of dibutylamylphosphate.
  • Example 9 The protecting solution consists of carbon tetrachloride containing a mixture of 1 part of 3,4 dichlorobenzenesulfobutylamide (melting point 77 C.) and 1.5 parts of tricresylphosphate.
  • Example 10 The protecting solution consists of trichlorethylene containing a mixture of 1 part of 3,4-dichlorobenzenesul1'ostearic amide of the formula:
  • Example 11 The protecting solution consists of perchlorethylene of the formula:
  • R stands for an aromatic nucleus
  • R1 and R2 stand for hydrogen or a radical selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of hydroxy, halogen, acidyl and alkylor arylacidylamino groups-but are free from free -sul fonic and carboxylic acid groups, and a phosphoric acid ester of the general formula:
  • R1, R2 and R mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.
  • a textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:
  • R1, R2 and R mean similar or dissimilar radicals selected from the group consisting of alkyl, arallgyl and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.
  • a textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:
  • R1 and R2 stand for hydrogen or a substituent selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of hydroxy, halogen, alkyl, aryl, acidyl and alkylor aryl-acidylamino groups, but are free from free sulfonic and carboxylic acid groups, and a phosphoric acid ester of the general formula:
  • R1, R2 and R3 mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl, and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic sol-' vents and generally representing colorless or faintly colored oils.
  • a textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:
  • R1 stands for hydrogen or a substituent selected from the group consisting of alkyl, aralkyl and aryl radicals, and a phosphoric acid ester of the general formula:
  • R1, R2 and R mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl and aryl radicals which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.
  • a textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the'general formula:
  • R1 stands for CH3, C2115 or C4119, and a phosphoric acid ester of the general formula:
  • R1, R2 and Rs mean similar or dissimilar radicals selected from the group consisting of CH3, CzHs, CsH'z, CiHs, C4H9.OCH2.CH2, Col-I5, CH3.C6H4 and CLCSH4, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.
  • a textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide 90 of the general formula:
  • a textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:.'
  • a textile pest-proofing composition com prising a mixture of an arylsulfonic acid amide of the general formula:
  • composition being soluble in organic solvents and representing a colorless or faintly colored oil.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Patented Apr. 17, 1934 PATENT car es uo'rnraoor'ma AGENT v Hermann Stiitter and Theodor Hermann, Leverkusen-I. G. Werk,
Germany Fubenindustrie Aktlengesellschal' on-the-Main,
, asaignors to I. G.
t, Frankfortntnmving. Application June 20, 1932, Serial No. 618,341. "In Germany September 1c, 1931 7 The-present invention relates to a process 01' protecting materials against attack by textile pests and tothe'compositions employed therein.
p In the'copend'ing U." 5. application Ser. No.
371,950, filed 14, 1929, agents are described for rendering, wool, fur, hair, feathers and the like proof against attack by moths.
These mothiprooflng agents generally consist of arylsulio'nic acid amides of the general 10 formula: I
16 wherein It stands for an aromatic nucleus, R1 and R2 stand. for hydrogen or a radical selected from the group consisting of alkyl radicals, aryl and aralkyl, and wherein all nuclei may further contain a substituent selected from the group consisting of hydroxyhalogen-, alkyl-, aryl-, alkylacidy1amino-, arylacidylamino-,. sulionic acidand carboxylic acid groups.
These compounds are highly active moth proofing agents, and, furthermore, excellently protectl wool, feathers, hair and the like also against the attack by other important textile pests, such as anthrenus Iasciatus, attagenus japonicus or attagenus piceus ol. Thereby they difier from other moth proofing agents, such as chlorinated naphthalenes, cinchona alkaloids and esters of phosphoric 'acid which are effective against moths, but ineffective against these textile pests.
amides, however, was limited hitherto, as they are not sufliciently soluble in benzine, carbon tetrachloride or trichlorethylene which are being principally-used in dry cleaning, and therefore m could not be used for such finished articles, for instance, clothes, iurs, upholstered furniture, museum specimens liable to attack by moths oi! felt in pianos, as are not suitable for a treatment with a water solution. I
We have now found that arylsulfonic acid amides of the above formula which are tree from tree sulionicor carboxylic :acid groups, when mixed withlphosphoric acid esters of the general formula:
, wherein R1, Ra, Ra means similar or dissimilar radicals selected from the group consisting of amide, such as the The application of these arylsultonic acid allryl, aryl and aralkyl radicals which may contain substituents selectedfrom the group consisting of halogen (Cl, Br.) and alkoxy (QCHa, OCaHs), are very easily soluble in benzine, carbon tetrachloride, trichlorethylene and other organic solvents. Therefore, such mixtures can be used in the customary dry cleaning solvents for protecting the articles mentioned above against attack by moths or other textile pests.
' These new mixtures generally represent colorless or faintly colored oils. The quantity of the active components to be applied for protecting materials against textilepests may vary within wide limits. For the mixture we generally use about two parts by weight of phosphoric acid ester, such as'the diethylbutylglycolphosphate, and one part by weight of an arylsulfonic acid 3,4-dichlorobenzenesulfomethylamide. The new compositions may be applied in any of the known manners. Thus, for example, the oilean be dissolved in benzine and sprayed on the materials to be protected or the same can be soaked with the solution or otherwise moistened therewith.
The following examples will illustrate our inso yention, but without limiting it thereto. The
parts are by weight.
Example 1.-Wool, feathers or hair are. treat ed in a benzine solution of the mixture containing 2 parts of 3,4-dichlorobenzene-sulfomethylamide of the formula H O1G0:.N/
OlEh and 3 parts of diethylbutylglycolphosphate oi the formula:
CIHIO CIHIOP=O treated in a benzine solution containing a mixture of 1 part of 3,4-dichlorobenzenesulfophenylamide of the formula:
, cPQosNH-O (melting point 82' C.)
in 1 part of triethylphosphate and 0.5 part of diethylbutylglycolphosphate.
Example 4.The goods are treated with a trichloroethylene solution of 1 part of 3,4-dichlorobenzenesulfo 2 methylbenzeneamide (melting point 110 C.) in 0.5 part of triethylphosphate and 1 part of diethylbutylglycolphosphate.
Example 5.The goods are treated with a carbon tetrachloride solution of 1 part of 3.4-dichlorobenzenesulfamide (melting point 136 C.) and 2 parts of triethylphosphate.
Example 6.The protecting solution consists of trichlorethylene containing a mixture of 1 part of dichlorobenzenesulfodimethylamide (melting point 128 C.) and 1.5 parts of triethylphosphate.
Example 7.-The protecting solution consists of benzine containing a mixture of 1 part of 3.4 dichlorobenzenesulfodiethylamide (melting point 58 C.) and 1.5 parts of tri-isoamylphosphate.
Example 8.The protecting solution consists of benzine containing a mixture of 1 part of 3,4 dichlorobenzenesulfodibutylamide (melting point 56 C.) and 1.5 parts of dibutylamylphosphate.
Example 9.-The protecting solution consists of carbon tetrachloride containing a mixture of 1 part of 3,4 dichlorobenzenesulfobutylamide (melting point 77 C.) and 1.5 parts of tricresylphosphate.
Example 10.-The protecting solution consists of trichlorethylene containing a mixture of 1 part of 3,4-dichlorobenzenesul1'ostearic amide of the formula:
CQOLNBLOOOMBI in 1.5 parts of diethylbutylglycolphosphate.
Example 11 .--The protecting solution consists of perchlorethylene of the formula:
(boiling point 121 C.)
containing a mixture of 1 part of 3,4-dichlorobenzenesulfoleic amide of the formula:
* Ol-QGO NHDOOuHa and 1 part of diethylglycolphosphate and 1 part of tributylphosphate. Goods treated with the wherein R stands for an aromatic nucleus, and R1 and R2 stand for hydrogen or a radical selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of hydroxy, halogen, acidyl and alkylor arylacidylamino groups-but are free from free -sul fonic and carboxylic acid groups, and a phosphoric acid ester of the general formula:
wherein R1, R2 and R: mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.
' 2. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:
RBOLN wherein R1, R2 and R: mean similar or dissimilar radicals selected from the group consisting of alkyl, arallgyl and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.
3. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:
wherein one X stands for a halogen atom, and the other X stands for hydrogen or a halogen atom; R1 and R2 stand for hydrogen or a substituent selected from the group consisting of alkyl, aralkyl and aryl radicals, which may further contain a substituent selected from the group consisting of hydroxy, halogen, alkyl, aryl, acidyl and alkylor aryl-acidylamino groups, but are free from free sulfonic and carboxylic acid groups, and a phosphoric acid ester of the general formula:
wherein R1, R2 and R3 mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl, and aryl radicals, which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic sol-' vents and generally representing colorless or faintly colored oils.
4. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:
wherein one X stands for a halogen atom, and the other X stands for hydrogen or a halogen atom; R1 stands for hydrogen or a substituent selected from the group consisting of alkyl, aralkyl and aryl radicals, and a phosphoric acid ester of the general formula:
wherein R1, R2 and R: mean similar or dissimilar radicals selected from the group consisting of alkyl, aralkyl and aryl radicals which may further contain a substituent selected from the group consisting of halogen and alkoxy groups, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.
5. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the'general formula:
wherein R1 stands for CH3, C2115 or C4119, and a phosphoric acid ester of the general formula:
wherein R1, R2 and Rs mean similar or dissimilar radicals selected from the group consisting of CH3, CzHs, CsH'z, CiHs, C4H9.OCH2.CH2, Col-I5, CH3.C6H4 and CLCSH4, said compositions being soluble in organic solvents and generally representing colorless or faintly colored oils.
. 6. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide 90 of the general formula:
H (Cra OHz and a phosphoric ester of the formula:
(hHIO C2HuO-P=O oim-o-mc-cmo said composition being soluble in organic solvents and representing a colorless or faintly colored oil.
'7. A textile pest-proofing composition comprising a mixture of an arylsulfonic acid amide of the general formula:.'
and a phosphoric acid ester of the formula:
CIHIO CaHlO said composition being soluble in organic solvents and representing a colorless or faintly'colored oil. I
8. A textile pest-proofing composition com prising a mixture of an arylsulfonic acid amide of the general formula:
p H CI SOLN/ and a phosphoric acid ester of the formula: 13o
CIHOO C4H|O-P==O said composition being soluble in organic solvents and representing a colorless or faintly colored oil.
HERMANN STOTTER.
THEODOR HERMANN.
US618341A 1931-09-16 1932-06-20 Mothproofing agent Expired - Lifetime US1955207A (en)

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2435274A (en) * 1943-06-24 1948-02-03 Rohm & Haas Control of insects
US2462835A (en) * 1943-09-03 1949-03-01 Du Pont Fly spray
US2552325A (en) * 1947-02-24 1951-05-08 Monsanto Chemicals Diethyl octyl phosphates
US2809131A (en) * 1954-06-23 1957-10-08 Mayo K Walden Process for protecting wool from yellowing by applying dibutyl butane-phosphonate
US2913476A (en) * 1954-11-05 1959-11-17 Olin Mathieson Sulfonamido dialkyl phosphates and process of making same
US2928863A (en) * 1955-09-03 1960-03-15 Bayer Ag Thiophosphoric acid esters and their production
US3132169A (en) * 1960-09-26 1964-05-05 Monsanto Chemicals Halogenated phosphorus esters, and process for preparing them
US3246976A (en) * 1961-06-30 1966-04-19 Stauffer Chemical Co Method for controlling crab grass and water grass
US3269898A (en) * 1961-08-25 1966-08-30 Bayer Ag Agents for protecting materials against textile pests
US4900867A (en) * 1986-07-10 1990-02-13 Kali-Chemie Aktiengesellschaft Process for producing fluorosulfonamides
WO1998005315A1 (en) * 1996-07-19 1998-02-12 Tularik, Inc. Pentafluorobenzenesulfonamides and analogs
US5880151A (en) * 1996-02-22 1999-03-09 Tularik Inc. Pentafluorobenzenesulfonamides and analogs
US6153585A (en) * 1998-07-20 2000-11-28 Tularik Inc. Arylsulfonanilide derivatives
US6211167B1 (en) 1998-06-25 2001-04-03 Tularik Inc. Arylsulfonanilide phosphates
US6214880B1 (en) 1998-09-23 2001-04-10 Tularik Inc. Arylsulfonanilide ureas
US6284923B1 (en) 1997-08-22 2001-09-04 Tularik Inc Substituted benzene compounds as antiproliferative and cholesterol lowering action
US6355628B1 (en) 1999-07-29 2002-03-12 Tularik Inc. Combination therapy using pentafluorobenzenesulfonamides
US6822001B2 (en) 2000-11-03 2004-11-23 Tularik Inc. Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents
US20050250854A1 (en) * 2000-11-03 2005-11-10 Amgen Inc. Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2435274A (en) * 1943-06-24 1948-02-03 Rohm & Haas Control of insects
US2462835A (en) * 1943-09-03 1949-03-01 Du Pont Fly spray
US2552325A (en) * 1947-02-24 1951-05-08 Monsanto Chemicals Diethyl octyl phosphates
US2809131A (en) * 1954-06-23 1957-10-08 Mayo K Walden Process for protecting wool from yellowing by applying dibutyl butane-phosphonate
US2913476A (en) * 1954-11-05 1959-11-17 Olin Mathieson Sulfonamido dialkyl phosphates and process of making same
US2928863A (en) * 1955-09-03 1960-03-15 Bayer Ag Thiophosphoric acid esters and their production
US3132169A (en) * 1960-09-26 1964-05-05 Monsanto Chemicals Halogenated phosphorus esters, and process for preparing them
US3246976A (en) * 1961-06-30 1966-04-19 Stauffer Chemical Co Method for controlling crab grass and water grass
US3269898A (en) * 1961-08-25 1966-08-30 Bayer Ag Agents for protecting materials against textile pests
US4900867A (en) * 1986-07-10 1990-02-13 Kali-Chemie Aktiengesellschaft Process for producing fluorosulfonamides
US7138418B2 (en) 1996-02-22 2006-11-21 Amgen, Inc. Pentafluorobenzenesulfonamides and analogs
US5880151A (en) * 1996-02-22 1999-03-09 Tularik Inc. Pentafluorobenzenesulfonamides and analogs
US6316484B1 (en) 1996-02-22 2001-11-13 Tularik Inc. Pentafluorobenzenesulfonamides and analogs
US6121304A (en) * 1996-02-22 2000-09-19 Tularik Inc Pentafluorobenzenesulfonamides and analogs
US20030162817A1 (en) * 1996-07-19 2003-08-28 Tularik Inc. Pentafluorobenzenesulfonamides and analogs
US6482860B1 (en) 1996-07-19 2002-11-19 Tularik Inc. Pentafluorobenzenesulfonamides and analogs
US6962929B2 (en) 1996-07-19 2005-11-08 Tularik Inc. Pentafluorobenzenesulfonamides and analogs
WO1998005315A1 (en) * 1996-07-19 1998-02-12 Tularik, Inc. Pentafluorobenzenesulfonamides and analogs
AU710173B2 (en) * 1996-07-19 1999-09-16 Tularik Inc. Pentafluorobenzenesulfonamides and analogs
US6284923B1 (en) 1997-08-22 2001-09-04 Tularik Inc Substituted benzene compounds as antiproliferative and cholesterol lowering action
US6388131B2 (en) 1997-08-22 2002-05-14 Tularik, Inc. Benzene compounds as antiproliferative and cholesterol lowering agents
US6417176B2 (en) 1998-06-25 2002-07-09 Tularik, Inc. Arylsulfonanilide phosphates
US6211167B1 (en) 1998-06-25 2001-04-03 Tularik Inc. Arylsulfonanilide phosphates
US6630513B1 (en) 1998-07-20 2003-10-07 Tularix Inc. Arylsulfonanilide derivates
US6153585A (en) * 1998-07-20 2000-11-28 Tularik Inc. Arylsulfonanilide derivatives
US7060718B2 (en) 1998-09-23 2006-06-13 Amgen Inc. Arylsulfonanilide ureas
US6583165B2 (en) 1998-09-23 2003-06-24 Tularik Inc. Arylsulfonanilide ureas
US20030207864A1 (en) * 1998-09-23 2003-11-06 Tulark Inc. Arylsulfonanilide ureas
US6214880B1 (en) 1998-09-23 2001-04-10 Tularik Inc. Arylsulfonanilide ureas
US6355628B1 (en) 1999-07-29 2002-03-12 Tularik Inc. Combination therapy using pentafluorobenzenesulfonamides
US20050250854A1 (en) * 2000-11-03 2005-11-10 Amgen Inc. Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents
US6822001B2 (en) 2000-11-03 2004-11-23 Tularik Inc. Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents

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