GB1038521A - Process and compounds for treating materials against fungal and bacterial infections and protected materials obtained thereby - Google Patents

Process and compounds for treating materials against fungal and bacterial infections and protected materials obtained thereby

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Publication number
GB1038521A
GB1038521A GB848/63A GB84863A GB1038521A GB 1038521 A GB1038521 A GB 1038521A GB 848/63 A GB848/63 A GB 848/63A GB 84863 A GB84863 A GB 84863A GB 1038521 A GB1038521 A GB 1038521A
Authority
GB
United Kingdom
Prior art keywords
aralkyl
alkyl
hydrogen
group
cycloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB848/63A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Metalsalts Corp
Original Assignee
Metalsalts Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Metalsalts Corp filed Critical Metalsalts Corp
Publication of GB1038521A publication Critical patent/GB1038521A/en
Expired legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel

Abstract

Soluble oils are protected against attack by microbes by incorporating therein a compound having one of the formulae <FORM:1038521/C4-C5/1> <FORM:1038521/C4-C5/2> <FORM:1038521/C4-C5/3> or a salt particularly a chlorinated phenol or o-phenyl phenol salt or a quaternary ammonium compound thereof, wherein R1-R14 are each hydrogen or an alkyl or alkenyl group having 1 to 18 carbon atoms, an aralkyl or substituted aralkyl group or cycloalkyl group having up to 9C, except that at least one of R11-R14 is not hydrogen, while R2 can also be hydroxyalkyl having 1-8C, X1-X4 are each hydrogen or an alkyl or alkenyl group having 1-18C, hydroxyalkyl, cycloalkyl having 1-9C, aryl or an aralkyl or substituted aralkyl group, while at least one of the pairs X1 and X2 and X3 and X4 may be part of a saturated heterocyclic ring containing the N atom and which may contain a further hetero atom selected from O, s, and N; and n is 1 to 6. Specified aralkyl groups are phesalkyl and naphthalkyl groups. The bases may be quaternized with alkylhalides, dialkyl sulphates, aralkyl halides or alkyl p-toluene sulphonates. Where X1 and X2 or X3 and X4 form part of ring with the N atom it may be a morpholine, piperidine, piperazine, or pyrrolidine ring. Materials treated are soluble oils consisting of petroleum fractions or lard, sperm or rape seed oil, which, petroleum fractions or fatty oils may be chlorinated, sulphurized or sulphonated and emulsifying agents, e.g. amine and sodium soaps of alcohols and polyethoxylated phenols which soluble oils may also contain alcohols, glycols or glycolethers as coupling agents.ALSO:Aqueous media are protected against attack by microbes by incorporating therein a compound having one of the formulae:- <FORM:1038521/C1/1> , <FORM:1038521/C1/2> and <FORM:1038521/C1/3> or a salt, particularly a chlorinated phenol or o-phenyl phenol salt or a quaternary ammonium compound thereof, wherein R1-R14 are each hydrogen or an alkyl or alkenyl group having 1 to 18 carbon atoms, an aralkyl or substituted aralkyl group or cycloalkyl group having up to 9C, except that at least one of R11-R14 is not hydrogen, while R2 can also be hydroxyalkyl having 1-8C, X1-X4 are each hydrogen or an alkyl or alkenyl group having 1-18C, hydroxyalkyl, cycloalkyl having 1-9C, aryl or an aralkyl or substituted aralkyl group, while at least one of the pairs X1 and X2 and X3 and X4 may be part of a saturated heterocyclic ring containing the N atom and which may contain a further hetero atom selected from O, S, and N; and n is 1 to 6. Specified aralkyl groups are phenalkyl and naphthalkyl groups. The bases may be quaternized with alkylhalides, dialkyl sulphates, aralkyl halides or alkyl p-toluene sulphonates. Where X1 and X2 or X3 and X4 form part of a ring with the N atom it may be a morpholine, piperidine, piperazine, or pyrrolidine ring. Materials treated are paper mill waters and oil flood waters.ALSO:Compounds of the formula <FORM:1038521/C2/1> and <FORM:1038521/C2/2> wherein R1 to R14 are each H, alkyl or alkenyl of 1-18 C, or aralkyl or substituted aralkyl or cycloalkyl of up to 9 C, except that at least one of R11-R14 is not hydrogen, while R2 can also be hydroxyalkyl of 1-8 C, X1-X4 are each H, alkyl or alkenyl of 1-18 C, hydroxy alkyl, cycloalkyl of up to 9 C, aryl or aralkyl or substituted aralkyl, while at least one of the pairs X1 and X2, and X3 and X4, may be part of a saturated heterocyclic ring containing the indicated N atom and may contain together with carbon a further hetero atom selected from O, S or N; and n is 1-6, are prepared from secondary amines and ketones and/or aldehydes according to the representative equations <FORM:1038521/C2/3> Specific compounds obtained include 2,2-bis (dimethylamino methyl) - 3 - hydroxypropionaldehyde, 2,2 - bis - (Di - n - propylaminomethyl) - cyclohexanone, 2,5 - bis (dimethylaminomethyl) - cyclopentanone dihydrochloride, N - piperidino - 2 - benzyl - 2 - dialkylaminomethyl - butanone - 3 (alkyl = methyl, ethyl or propyl), 2-(dibenzylaminomethyl)-6-(dimethylaminomethyl) - cyclohexanone and its hydrochloride. The 2,4,5-trichlorophenol, o-phenyl phenol, and 2,4,6-trichloro phenol salts of the above amines are prepared by reacting the free base or its hydrochloride with the phenol. The free bases may be quaternated by reaction with alkylating or aralkylating agents.ALSO:Materials other than plants and other living organisms are protected against attack by microbes by incorporating therein a compound having one of the formulae <FORM:1038521/A5-A6/1> or a salt particularly a chlorinated phenol or o-phenyl phenol salt or a quaternary ammonium compound thereof, wherein R1-R14 are each hydrogen or an alkyl or alkenyl group having 1 to 18 carbon atoms, an aralkyl or substituted aralkyl group or cycloalkyl group having 1 to 9C, except that at least one of R11-R14 is not hydrogen, while R2 can also be hydroxyalkyl having 1-8C, X1-X4 are each hydrogen or an alkyl or alkenyl group having 1-18C, hydroxyalkyl, cycloalkyl having 1-9C, aryl or an aralkyl or substituted aralkyl group, while at least one of the pairs X1 and X2 and X3 and X4, may be part of a saturated heterocyclic ring containing the N atom and which may contain a further hetero atom selected from O, S, and N; and n is 1 to 6. Specified aralkyl groups are phenalkyl and naphthalkyl groups. The bases may be quaternized with alkyl halides dialkyl sulphates, aralkyl halides or alkyl p-toluene sulphonates. Where X1 and X2 or X3 and X4 form part of a ring with the N atom it may be a morpholine, piperidine, piperazine, or pyrrolidine ring. Materials treated are adhesives, paints, waxes, polishes, wood, paper mill waters, oil flood waters, wood and soluble oils consisting of petroleum fractions or lard, sperm or rape seed oil, which petroleum fractions or fatty oils may be chlorinated, sulphurized or sulphonated and emulsifying agents e.g. amine and sodium soaps of alcohols and polyethoxylated phenols which soluble oils may also contain alcohols, glycols or glycol ethers as coupling agents.
GB848/63A 1962-01-08 1963-01-08 Process and compounds for treating materials against fungal and bacterial infections and protected materials obtained thereby Expired GB1038521A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US16502862A 1962-01-08 1962-01-08

Publications (1)

Publication Number Publication Date
GB1038521A true GB1038521A (en) 1966-08-10

Family

ID=22597103

Family Applications (1)

Application Number Title Priority Date Filing Date
GB848/63A Expired GB1038521A (en) 1962-01-08 1963-01-08 Process and compounds for treating materials against fungal and bacterial infections and protected materials obtained thereby

Country Status (8)

Country Link
JP (1) JPS4830381B1 (en)
BE (1) BE626862A (en)
BR (1) BR6345948D0 (en)
CH (1) CH475706A (en)
DE (1) DE1492387A1 (en)
GB (1) GB1038521A (en)
NL (2) NL143134B (en)
SE (1) SE308424B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008081602A (en) * 2006-09-27 2008-04-10 Yushiro Chem Ind Co Ltd Water-soluble metal working agent, coolant and its preparation method, microorganism deterioration prevention method for water-soluble metal working agent and metal working

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008081602A (en) * 2006-09-27 2008-04-10 Yushiro Chem Ind Co Ltd Water-soluble metal working agent, coolant and its preparation method, microorganism deterioration prevention method for water-soluble metal working agent and metal working
CN101522875B (en) * 2006-09-27 2012-07-04 尤希路化学工业株式会社 Water-soluble metal-processing agent, coolant, method for preparation of the coolant, method for prevention of microbial deterioration of water-soluble metal-processing agent, and metal processing
US8476208B2 (en) 2006-09-27 2013-07-02 Yushiro Chemical Industry Co., Ltd. Water-soluble metal-processing agent, coolant, method for preparation of the coolant, method for prevention of microbial deterioration of water-soluble metal-processing agent, and metal processing

Also Published As

Publication number Publication date
NL143134B (en) 1974-09-16
BE626862A (en)
JPS4830381B1 (en) 1973-09-19
SE308424B (en) 1969-02-10
CH475706A (en) 1969-07-31
BR6345948D0 (en) 1973-05-15
NL287541A (en)
DE1492387A1 (en) 1969-08-07

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