DE1168158B - Termite repellants - Google Patents
Termite repellantsInfo
- Publication number
- DE1168158B DE1168158B DEF28641A DEF0028641A DE1168158B DE 1168158 B DE1168158 B DE 1168158B DE F28641 A DEF28641 A DE F28641A DE F0028641 A DEF0028641 A DE F0028641A DE 1168158 B DE1168158 B DE 1168158B
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethyl
- termite
- phenylsulfonyl
- chloro
- trichloroaniline
- 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.)
- Pending
Links
- 241000256602 Isoptera Species 0.000 title claims description 18
- 239000000463 material Substances 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- -1 building boards Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000011083 cement mortar Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/16—Sulfur-containing compounds
- C04B24/20—Sulfonated aromatic compounds
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/38—Aromatic compounds
- B27K3/40—Aromatic compounds halogenated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/38—Aromatic compounds
- B27K3/42—Aromatic compounds nitrated, or nitrated and halogenated
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Termitenschutzmittel Gegenstand der vorliegenden Erfindung ist die Verwendung von Benzolsulfonsäurearylamiden, die in den Arylresten mindestens eine Trifluormethylgruppe und mindestens ein Chloratom oder eine Nitrogruppe enthalten, wobei die Gesamtzahl dieser Substituenten in einem Arylrest 4 und in beiden zusammen 6 nicht übersteigen soll, zum Schutz von Materialien gegen Termitenfraß.Termite repellants The present invention is the Use of Benzolsulfonsäurearylamiden, which in the aryl radicals at least one Contain trifluoromethyl group and at least one chlorine atom or one nitro group, the total number of these substituents in an aryl radical being 4 and in both together 6 should not exceed, for the protection of materials against termite damage.
Die erfindungsgemäß zu verwendenden Benzolsulfonsäurearylamide vermögen beispielsweise Holz, Bauplatten, Papier, Textilien, synthetische Fasern, Kunststoffe, Kautschuk, Leder, Lacke, Bitumen, Zementmassen, Kabel, Polyvinylchloride, Polyäthylen und andere gegen Termiten anfällige Materialien schon bei Anwendung von 1 bis 20/0, teilweise sogar in niedrigerer Konzentration, dauerhaft gegen Termitenfraß zu schützen. Eine 0,5 mm starke Filterscheibe von 9 cm Durchmesser wird mit 2 ccm einer 0,05%igen Acetonlösung von 2,4,5-Trichlor-phenylsulfonyl-2'-chlor-5'-trifluormethylanilin (F. _ 100°C) so behandelt, daß das Papier gleichmäßig getränkt ist. Nach 4tägiger Ausdunstung werden 20 Termitenarbeiter. in einem Metallring auf die behandelte Papierfläche gesetzt. Während einer 3tägigen Versuchsdauer bleibt das Papier unbeschädigt. Nach 5monatiger Lagerung im Tropenklima unter ständigem Luftwechsel besitzt die Filterscheibe noch die gleiche Wirkung gegenüber Termiten. Mit Wasser von 50°C angeschlemmtem Defibratorstoff (feinzerfasertes Holz) setzt man alkalisch eingestelltes Phenolformaldehydharz und Paraffin, mit Emulgator dispergiert, zu. Anschließend wird 1% 3,4-Dichlor-phenylsulfonyl-2'-chlor-5'-trifluormethylanilin (F. = 106 bis 107°C), in etwas Natronlauge gelöst, eingerührt und der Brei mit Aluminiumsulfat bei pH = 4 gefällt und zuletzt entwässert. So ausgerüstete Hartfaserplatten erweisen sich als termitenresistent und besitzen selbst nach Lagerung im Tropenklima eine gute Dauerwirkung. 70 Teile Polyvinylchlorid werden gemischt mit 30 Teilen handelsüblichem Weichmacher (z. B. Dioctylphthalat), in dem l0/0 2-Trifluormethyl-4-chlor-, phenylsulfonyl-2'-trifluormethyl-4'-chloranilin (F. = 124 bis 125°C) gelöst worden ist. Zur Stabilisierung setzt man 0,3 bis 1% handelsüblichen Stabilisator (Diphenylthioharnstofl) zu. Auf dem Mischwalzwerk wird gemischt (175°C), ausgeliert und eine Folie von 1 mm Stärke gepreßt. Die so behandelten Folien oder Kabel aus Polyvinylchlorid sind gegen Termitenfraß resistent. 1 Gewichtsteil 2-Nitro-phenylsulfonyl-2'-trifluormethyl-4.'-chloranilin (F. = 143'C) wird in 100 Gewichtsteile Polyäthylen bei 130°C 6 bis 8 Minuten eingewalzt, so daß der Wirkstoff in dem Polyäthylen homogen gelöst ist. Derart ausgerüstete Polyäthylenfolien besitzen noch nach 2jähriger Prüfzeit eine vollkommene Resistenz gegen Termitenfraß. Kiefernsplintholz wird mit einer 0,5%igen Acetonlösung von 4-Chlor-phenylsulfonyl-2'-chlor-5'-trifluormethylanilin (F. = 114 bis 115°C) im Vakuumverfahren vollimprägniert. Die tatsächliche Aufnahme beträgt dabei 0,3% Wirkstoff/Holzgewicht. Prüfungen in regelmäßigen Abständen über einen Zeitraum von 2 Jahren haben ergeben, daß das Holz nicht von Termiten angegriffen wurde. In Mischungen aus Naturkautschuk, Butadien-Styrol - Mischpolymerisaten, Butadien - Acrylnitril-Mischpolymerisaten, Polychlorbutadien und Butylkautschuk werden 2 bis 3% 4-Nitro-phenylsulfonyl-2'-trifluormethyl-4'-chloranilin (F. = 150°C) auf der Walze oder im Kneter eingearbeitet. Sowohl in unvulkanisierter als auch vulkanisierter Form erweisen sich die erhaltenen Produkte als termitenresistent.The benzenesulfonic acid arylamides to be used according to the invention are capable of, for example, wood, building boards, paper, textiles, synthetic fibers, plastics, rubber, leather, varnishes, bitumen, cement compounds, cables, polyvinyl chlorides, polyethylene and other materials susceptible to termites even when using 1 to 20/0 to provide permanent protection against termite damage, sometimes even in lower concentrations. A 0.5 mm thick filter disk with a diameter of 9 cm is filled with 2 ccm of a 0.05% strength acetone solution of 2,4,5-trichlorophenylsulfonyl-2'-chloro-5'-trifluoromethylaniline (m.p. 100 ° C) treated so that the paper is soaked evenly. After 4 days of evaporation, 20 become termite workers. placed in a metal ring on the treated paper surface. The paper remains undamaged during a 3-day test period. After 5 months of storage in a tropical climate with constant air change, the filter disc still has the same effect on termites. Defibrator material (finely fiberized wood) suspended in water at 50 ° C. is added to alkaline phenol-formaldehyde resin and paraffin, dispersed with an emulsifier. Then 1% 3,4-dichloro-phenylsulfonyl-2'-chloro-5'-trifluoromethylaniline (melting point = 106 to 107 ° C.) is dissolved in a little sodium hydroxide solution, stirred in and the paste is precipitated with aluminum sulfate at pH = 4 and finally drains. Hardboard panels finished in this way prove to be termite-resistant and have a good long-term effect even after storage in a tropical climate. 70 parts of polyvinyl chloride are mixed with 30 parts of commercially available plasticizers (e.g. dioctyl phthalate) in which 10/0 is 2-trifluoromethyl-4-chloro-, phenylsulfonyl-2'-trifluoromethyl-4'-chloroaniline (m.p. 124 to 125 ° C) has been dissolved. For stabilization, 0.3 to 1% of a commercially available stabilizer (diphenylthiourea) is added. Mixing is carried out on the mixing mill (175 ° C.), gelled and a 1 mm thick film is pressed. The polyvinyl chloride foils or cables treated in this way are resistant to termite damage. 1 part by weight of 2-nitro-phenylsulfonyl-2'-trifluoromethyl-4'-chloroaniline (F. = 143'C) is rolled into 100 parts by weight of polyethylene at 130 ° C. for 6 to 8 minutes, so that the active ingredient is homogeneously dissolved in the polyethylene is. Polyethylene foils equipped in this way are completely resistant to termite damage even after a test period of 2 years. Pine sapwood is fully impregnated with a 0.5% acetone solution of 4-chloro-phenylsulfonyl-2'-chloro-5'-trifluoromethylaniline (mp = 114 to 115 ° C) in a vacuum process. The actual absorption is 0.3% active ingredient / weight of wood. Tests at regular intervals over a period of 2 years have shown that the wood was not attacked by termites. In mixtures of natural rubber, butadiene-styrene copolymers, butadiene-acrylonitrile copolymers, polychlorobutadiene and butyl rubber, 2 to 3% 4-nitro-phenylsulfonyl-2'-trifluoromethyl-4'-chloroaniline (temperature = 150 ° C) are added to the Incorporated into a roller or in a kneader. The products obtained prove to be termite-resistant in both unvulcanized and vulcanized form.
Auf gleiche Weise läßt sich auch das 3-Nitrophenylsulfonyl-2'-trifluormethyl-4'-chioranilin zum Termitenschutz anwenden. Beispiel 7 Bei der Zubereitung von Zementmörtel wird dem Anmachwasser 20% 2-Chlor-5-trifluormethyl-phenylsulfonyl-2',4',5'-trichloranilin beigegeben. So hergestellte Platten sind für Termiten immun im Gegensatz zu nicht präpariertem Material, in das die Schädlinge eindringen können.3-Nitrophenylsulfonyl-2'-trifluoromethyl-4'-chloroaniline can also be prepared in the same way use for termite protection. Example 7 When preparing cement mortar, 20% 2-chloro-5-trifluoromethyl-phenylsulfonyl-2 ', 4', 5'-trichloroaniline is added to the mixing water added. Plates made in this way are immune to termites in contrast to unprepared material into which the pests can penetrate.
Beispiel 8 Wolle wird im wäßrigen Bade bei Kochtemperatur mit 0,5% 3-Trifluormethyl-phenylsulfonyl-2',4',5'-trichloranilin ausgerüstet. Nach Seifenwäsche und 2jähriger Lagerung im Tropenklima ist die Wolle noch termitenresistent.Example 8 Wool is in an aqueous bath at boiling temperature with 0.5% 3-trifluoromethyl-phenylsulfonyl-2 ', 4', 5'-trichloroaniline equipped. After washing with soap and storing it for 2 years in a tropical climate, the wool is still termite-resistant.
Beispiel 9 Lacke, denen 3% 3,5-Di-trifluormethyl-phenylsulfonyl-2',4',5'-trichloranilin zugesetzt wird, sind gegen Beschädigungen durch Termiten geschützt.Example 9 Paints containing 3% 3,5-di-trifluoromethyl-phenylsulfonyl-2 ', 4', 5'-trichloroaniline added are protected against damage by termites.
Als Schutzmittel gegen Termitenfraß lassen sich außerdem folgende Verbindungen verwenden 3,5-Bis-trifluormethyl-phenylsulfonyl-2'-trifluormethyl-4'-chloranilin, F. = 112 bis 113°C. 4-Chlor-3-trifluormethyl-phenylsulfonyl-2',4',5'-trichloranilin, F. = 147 bis 148°C. 3-Trifluormethyl-5-nitro-phenylsulfonyl-2',3',5'-trichloranilin, F. = 143°C. 2-Chlor-5-trifluormethyl-phenylsulfonyi-N-methyl-2',4',5'-trichloranilin, F. = 101'C. 2-Trifluormethyl-4-chlor-phenylsulfonyl-tetrachlor-2'-naphthylamin [erhältlich durch Chlorierungvon 2-Trifluormethyl-4-chlorphenylsulfonyl-2'-naphthylamin in Chloroform in Gegenwart von Eisen(III)-chlorid und anschließendes Umkristallisieren (aus Benzin), F. = 196 bis 197°C].The following can also be used as a means of protection against termite damage Compounds use 3,5-bis-trifluoromethyl-phenylsulfonyl-2'-trifluoromethyl-4'-chloroaniline, M.p. = 112 to 113 ° C. 4-chloro-3-trifluoromethyl-phenylsulfonyl-2 ', 4', 5'-trichloroaniline, F. = 147 to 148 ° C. 3-trifluoromethyl-5-nitro-phenylsulfonyl-2 ', 3', 5'-trichloroaniline, M.p. = 143 ° C. 2-chloro-5-trifluoromethyl-phenylsulfonyi-N-methyl-2 ', 4', 5'-trichloroaniline, F. = 101'C. 2-Trifluoromethyl-4-chlorophenylsulfonyl-tetrachloro-2'-naphthylamine [available by chlorination of 2-trifluoromethyl-4-chlorophenylsulfonyl-2'-naphthylamine in chloroform in the presence of iron (III) chloride and subsequent recrystallization (from gasoline), M.p. = 196 to 197 ° C].
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28641A DE1168158B (en) | 1959-06-08 | 1959-06-08 | Termite repellants |
| CH613160A CH387375A (en) | 1959-06-08 | 1960-05-30 | Process for the protection of non-textile materials from termite damage |
| GB1982660A GB952337A (en) | 1959-06-08 | 1960-06-03 | Process for the protection of materials against termite-attack using arylamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28641A DE1168158B (en) | 1959-06-08 | 1959-06-08 | Termite repellants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1168158B true DE1168158B (en) | 1964-04-16 |
Family
ID=7092964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28641A Pending DE1168158B (en) | 1959-06-08 | 1959-06-08 | Termite repellants |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH387375A (en) |
| DE (1) | DE1168158B (en) |
| GB (1) | GB952337A (en) |
-
1959
- 1959-06-08 DE DEF28641A patent/DE1168158B/en active Pending
-
1960
- 1960-05-30 CH CH613160A patent/CH387375A/en unknown
- 1960-06-03 GB GB1982660A patent/GB952337A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH387375A (en) | 1965-01-31 |
| GB952337A (en) | 1964-03-18 |
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