Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
  • C07C39/24—Halogenated derivatives
  • C07C39/44—Metal derivatives of an hydroxy group bound to a carbon atom of a six-membered aromatic ring
• • 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
  • A01N33/12—Quaternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
  • C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
  • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
  • D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic

Definitions

• This invention relates to water-soluble organic copper compounds and to a process for their production.
• Copper pentachlorophenate which is known to have a strong fungicidal action, is used in the treatment of textiles and is preferably produced on the fabric to be protected by a two-bath impregnation process. It can also be introduced in aqueous dispersion together with synthetic resins.
• Another object is to provide a process for making water-soluble organic copper compounds having a strong fungicidal action.
• copper salts of pentachlorophenol are reacted with excess organic quaternary nitrogen compounds, such as cetyl benzyl dimethyl ammonium chloride.
• the copper pentachlorophenate can also be formed in situ from an alkali metal pentachlorophenate and the equivalent amount of a copper salt during the reaction with the said organic quaternary nitrogen compounds.
• organic quaternary nitrogen compounds which are suitable according to the invention are compounds which can be represented by the formula:
• R and R represent lower aliphatic radicals having 1 to 4 carbon atoms
• R is a long-chain parafiin having 8 to 24 carbon atoms, preferably a lauryl, stearyl, or cetyl radical
• R stands for a benzyl radical which may be substituted in the aromatic nucleus by lower aliphatic radicals, halogen atoms or nitro groups
• X means an anion, e.g. chlorine, bromine, or a sulfuric acid radical.
• the aforesaid organic quaternary nitrogen compounds are used in an excess of 0.2-l mols, preferably 1-5 mols, referred to copper pentachlorophenate.
• the reaction is carried out in the melt at a temperature be tween 20 and 100 0., preferably 30-60 C.; a small amount of water or alcohol may be present in the reaction.
• the products of the invention give a colloidal solution in water and are even substantively absorbed on cellulose. Consequently, the strong fungicidal action is maintained during soaking.
• the treated textile fibres are extremely resistant to the influence of weather. The effects produced in hitherto known manner by means of the two-bath process are therefore clearly inferior to those obtained with the copper compounds which can be 2 ,886,580 Patented May 12, 1959 produced by the process of the present invention.
• Yet another advantage of the product obtained is that the treated materials do not assume the brown colouring of the copper pentachlorophenate, but remain unaffected with their natural colour.
• Example 1 1 part of dry copper pentachlorophenate is heated with 3 parts of cetyl benzyl dimethyl ammonium chloride to a temperature of 45 C. while stirring, heating being continued until a homogeneous water-soluble paste is formed. This paste, after being diluted with water, can be used without any further treatment for the treatment of cellulose fibres.
• Example 2 Example 3 If the procedure indicated in Example 2 is followed, but with a final additon of 1 gm. of colloidal silica in order to improve the resistance of the product to ageing and increase in temperature, there is obtained a paste which is stable for a particularly long time and which has all the proper-ties possessed by the compounds prepared as described in Examples 1 and 2.
• Example 4 27.0 g. of stearyl benzyl dimethyl ammonium chloride are melted with the addition of 4.6 g. of copper sulfate and with stirring. The temperature is kept at 50 C. and 10.4 g. of sodium pentachlorophenate are added with stirring together with 10.0 cc. of water. Stirring is continued until the paste has become homogeneous and completely water-soluble.
• Example 5 To 10.5 g. of copper acetate there is added a solution of 21.6 g. of cetyl benzyl dimethyl ammonium chloride in 23.9 cc. of water. The mixture is heated up to 45 C. and 10.4 g. of finely powdered sodium pentachlorophenate are added with stirring. The temperature is maintained and the paste stirred until it has become homogeneous and dissolves in water without a residue.
• a process for the production of water-soluble organic copper compounds which comprises mixing copper pentachlorophenate with an excess of a quaternary alkylated benzyl ammonium compound of the general formula:
• R and R representing a lower aliphatic radical having 1 to 4 carbon atoms, R being a long-chain paratfin having 8 to 24 carbon atoms, R, being a member selected from the group consisting of a benzyl radical and a chlo rinated benzyl radical and X is an anion, until a homogeneous, water-soluble paste is obtained.
• a water soluble lauryl benzyl dimethyl ammonium action is carried out in the melt at a temperature between chloride copper pentachlorophenate compound obtained 30-60 C. in the presence of a small quantity of water. by the process claimed in claim 1.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Environmental Sciences (AREA)
• Biochemistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Health & Medical Sciences (AREA)
• Plant Pathology (AREA)
• Dentistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Microbiology (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Inorganic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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Citations (3)

• 0
  • BE BE540745D patent/BE540745A/xx unknown
• 1955
  • 1955-08-04 US US526556A patent/US2886580A/en not_active Expired - Lifetime
  • 1955-08-30 FR FR1130405D patent/FR1130405A/fr not_active Expired
  • 1955-09-02 GB GB25307/55A patent/GB777544A/en not_active Expired

Patent Citations (3)

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