AU625875B2 - Solubilizing process for the manufacture of a copper oxinate preparation - Google Patents
Solubilizing process for the manufacture of a copper oxinate preparation Download PDFInfo
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- AU625875B2 AU625875B2 AU38990/89A AU3899089A AU625875B2 AU 625875 B2 AU625875 B2 AU 625875B2 AU 38990/89 A AU38990/89 A AU 38990/89A AU 3899089 A AU3899089 A AU 3899089A AU 625875 B2 AU625875 B2 AU 625875B2
- Authority
- AU
- Australia
- Prior art keywords
- copper
- oxinate
- copper oxinate
- solubilizer
- process according
- 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.)
- Ceased
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- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- 230000003381 solubilizing effect Effects 0.000 title description 3
- 239000002904 solvent Substances 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 2-ethyl-hexyl Chemical group 0.000 claims description 5
- 150000005690 diesters Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 4
- 238000005063 solubilization Methods 0.000 description 4
- 230000007928 solubilization Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical group C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F13/00—Bandages or dressings; Absorbent pads
- A61F13/15—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators
- A61F13/53—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium
- A61F2013/530131—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium being made in fibre but being not pulp
- A61F2013/530226—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium being made in fibre but being not pulp with polymeric fibres
- A61F2013/53024—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium being made in fibre but being not pulp with polymeric fibres being bicomponent fibres
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F13/00—Bandages or dressings; Absorbent pads
- A61F13/15—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators
- A61F13/53—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium
- A61F2013/530481—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium having superabsorbent materials, i.e. highly absorbent polymer gel materials
- A61F2013/5307—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators characterised by the absorbing medium having superabsorbent materials, i.e. highly absorbent polymer gel materials characterized by the quantity or ratio of superabsorbent material
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemically Coating (AREA)
Description
I
H
7
-Y
Our Ref: 282938 AUSTRAL, 25837 FORM COMPLETE SPECIFICATION
(ORIGINAL)
Application Number: Lodged: 0*O #0 0 00 0 0 0 00 0 0 00 0 Complete Specification Lodged: Accepted: Published: Priority: Related Art: Applicant(s): *0 0 0 ft~) 00 I-.HoffMr-a-ReIrA-G.- 124 184 GroAn:%ae -r-t -asse- Gi CI 002-Bas-1-- S BER13ItAND ARTHUR S. CAVE CO.
Patent Trade Mark Attornex Level 10, 10 Barrack Street SYDNEY NSW 2000
~CA
Address for Service: Complete specification for the invention entitled Solubilizing Process for the Manufacture of a Copper Oxinate Preparation".
90 0 0 The following statement is a full description of this invention, including the best method of performing it known to me:- 1- 5020 -la- The present invention is concerned with a solubilization process, namely a process for the manufacture of a copper oxinate preparation which is soluble in organic solvents and, respectively, of a copper oxinate solution in an organic solvent.
o.C Copper oxinate (oxine copper), i.e. the complex of Cu (II) with 8-hydroxyquinoline. and its fungicidal 15 properties have been known for a long time and have been described in numerous publications Pesticide Manual.
o 0.
8th Ed., page 622). It is also known that copper oxinate is soluble in water under strongly acidic conditions (pH For certain uses it is, however, advantageous or necessary to provide solutions of copper oxinate in an organic solvent. Such solutions have hitherto been o° prepared by solubilizing copper oxinate with nonylphenol or 2-ethylhexanoic acid Ni salt Patents 2,651,379, 2,561,380 and 2,608,556). However, nickel salts as well as 25 nonylphenol belong to the toxicologically-hazardous substances which, for this' ceason, must no longer be used in certain countries.
It has now surprisingly been found that copper oxinate can be dissolved in organic solvents using certain phosphoric acid esters as solubilizers.
The phosphoric acid esters which are usable as solubilizers are liquid substances which correspond to the 3 formula As/23.5.89 2 0
II
RO-P-OR' (I)
S
S S I 4i 1 ft i t iI I I r i i i:i r i Ii t t 1 i I wherein R and R' represent hydrogen or an alkyl group with up to 13 carbon atoms, whereby at least one of the symbols R and R' is an alkyl group.
The compounds of formula I above are accordingly known 15 monoesters and diesters of phosphoric acid.
The process in accordance with the invention for the manufacture of a copper oxinate preparation which is soluble in organic solvents and, respectively, of a copper oxinate solution in an organic solvent accordingly comprises using as a solubilizer a compound of general formula I above in which R and R' have the above significance.
25 The alkyl groups R and R' can be straight-chain or branched, whereby straight-chain alkyl groups can contain 1-8 carbon atoms and branched alkyl groups can contain up to 13 carbon atoms, i.e. 3-13 carbon atoms. Examples of such alkyl groups are methyl, ethyl, propyl, isopropyl.
30 butyl, isobutyl, amyl, hexyl, 2-ethyl-hexyl, octyl, isooctyl and isotridecyl.
Mixtures of monoesters and diesters of formula I above can also be used as the solubilizer.
Especially preferred solubilizers are monoesters and diesters of formula I in which R and/or R' signifies 2-ethyl-hexyl and mixtures of such monoesters and diesters.
00., *666 9 00 01 9 *0 3 The weight ratio between copper oxinate and solubilizer can vary within a wide range.
Copper oxinate and solubilizer are conveniently used in a weight ratio of about 1:0.5 to about 1:50, conveniently about 1:1 to about 1:50, and preferably in a weight ratio of about 1:4 to 1:15. A weight ratio range of 1 0 about 1:6 to about 1:10 is especially preferred.
A preparation which is suitable for the manufacture of a copper oxinate solution in an organic solvent is obtained by mixing the copper oxinate with the 15 solubilizer. Such a solution can be manufactured either by diluting the mixture, which is obtained by mixing the copper oxinate with the solubilizer. with the solvent or by mixing the copper oxinate, the solubilizer and the solvent with one another, optionally while heating. The 20 dissolution process is accelerated by heating (depending on the solvent, for example, to temperatures between about 0 C and 120 0
C).
Solutions of copper oxinate with very different copper 25 oxinate contents, up to about 15% copper oxinate, can be manufactured in this manner. Preferred solutions are those having a content between about 1 and 10 wt.%.
As solvents there come into consideration industrial 30 solvents which are usual for similar products, for example aliphatic and aromatic hydrocarbons, ketones, esters, lactones and the like. Examples of such solvents are SOLVESSO® 100 which consists of alkylbenzenes, SOLVESSO® 200 which consists of alkylnaphthalenes, Sangajol which consists of aliphatic and aromatic hydrocarbons, benzyl alcohol, methyl isobutyl ketone, y-butyrolactone and propylene glycol monomethyl ether acetate (DOWANOL® PMA).
Ji 6 0i I I 60.0 4 The solutions manufactured in accordance with the present invention can be used directly as finished solutions or, after dilution with solvents, prefetibly mineral oils, according to conventional application methods such as e.g. dipping, spraying, brushing etc. By adding emulsifiers to the solutions obtained in accordance with the invention there are obtained emulsifiable concentrates which can be applied after dilution with water.
Example 1 o 15 A green-blue solution of copper oxinate is obtained by o* stirring 10 parts of copper oxinate. 60 parts of an about equimolar mixture of mono-2-ethyl-hexyl-phosphate and di-2-ethyl-hexyl-phosphate and 30 parts of ethylene glycol phenyl ether at 80 0
C.
Example 2 o a* a* 0 A deep blue-green solution of copper oxinate is obtained by stirring a mixture of 8 parts of copper oxinate, 60 parts of an about equimolar mixture of the phosphates referred to in Example 1 and 32 parts of benzyl S alcohol at 120 0 C for 2 hours.
000I Example 3 2 parts of copper oxinate, 45 parts of monobutyl phosphoric acid ester, 33 parts of SOLVESSO® 100 (alkylbenzene mixture) and 20 parts of nonylphenol polyethoxylate are stirred at room temperature for about 1 hour until all of the copper oxinate has dissolved.
There thus results a greenish, clear solution which, because of the emulsifier content (nonylphenol polyethoxylate), can be diluted with water.
"I
p 5 The composition of various copper oxinate preparations in accordance with the present invention is given in Tables A-C hereinafter in which the abbreviations used have the following significances: MDM: Mixture of mono- and dimethyl esters of phosphoric acid MDB: Mixture of mono- and dibutyl esters of phosphoric acid 0o MDAH: Mixture of mono- and di-2-ethyl-hexyl esters of a phosphoric acid MDIT: Mixture of mono- and diisotridecyl esters of 15 phosphoric acid MOB: monobutyl ester of phosphoric acid o o0 0o oo e I These products are manufactured by the firm HOECHST amongst others.
Table A shows the use of different solubilizers when using a copper oxinate/solvent (cyclohexanone) ratio of °o 1:10.
0 66 Table A *o Composition in wt.% e 0 o Copper oxinate 5 5 5 5 Solubilizer MDM MDB "MOB SMDAH "MDIT Cyclohexanone 50 50 50 50 The solubilization is effected by heating to 120 0 C for 1 hour. There are obtained deep green solutions which are suitable for the manufacture of copper oxinate solutions in organic solvents.
F'
-6 Table B shows the use of different .olvents.
Table B Composition in wt..% 0888 8888 8848 8 8 8*88 8 8 8 88 8 88 88 8 88 *8 9*8@ 8 8 8 8* 8 88 8 8 8 8 88 1 Copper oxinate Solubilizer
MDM
MDAH
I4DIT Propylene glycol monomethyl ether 15 Benzyl alcohol Ethylene glycol phenyl ether EXSOLO D-100
(EXXON)
SOLVESSOO 200
(EXXON)
5 8 3.O 5 60 60 Here, the solubilization is also achieved by heating to 50 to 120 0 C for 1 to 2 hours.
Table C shows examples of different concentrations and weight ratios copper oxinate: solubilizer. the last column relating to a preparation which is emulsifiable in water.
-7 Table C Comn~poition in wt.% Copper oxinate Solubilizer
MOB
MDAH
0000 0 0 0000 000 0 0 00 0 0000 0 0 0 00 0 0 00 00 0 0 0 Benzyl alcohol SOLVESSOO 100 (EXXON) Nonyiphenol polyethoxylate (emulsifier) Copper oxinate: 1~5 solubilizer ratio Solubilization conditions: 1: 1 7h/120 0
C
1:2 lh/120 0
C
1: 4 lh/120 0
C
1:22 1 h,'RT 0 0 0 00 0 0 0 0 00 00 0 000 .0 0 9000 00 0 0 0 @0
Claims (9)
1. A process for the manufacture of a copper oxinate preparation which is soluble in organic solvents and, respectively, of a copper oxinate solution in an organic solvent, which process comprises using as a solubilizer a compound of the general formula 0000 0 4 4 RO-P-OR' rdii OH wherein R and R' represent hydrogen or an alkyl group with up to 13 atoms, whereby at least one of the symbols R and R' is an alkyl group.
2. A process according to claim 1, wherein a compound of formula I in which R and/or R' signifies a straight-chain alkyl group with 1-8 carbon atoms is used.
3. A process accotding to claim 1. wherein a compound of formula I in which R and/or R' signifies a branched-chain alkyl group with 3-13 carbon atoms is used. a4 0 0 0 25 4 t. 4: 00 5 4 0 4 44
4. A process according to claim 1 or claim 3, wherein a compound of formula I in which R and/or R' signifies 2-ethyl-hexyl is used.
A process according to any one of claims 1-4, wherein a mixture of monoesters and diesters of formula I is used as the solubilizer.
6. A process according to any one of claims wherein copper oxinate and 6 ,lubilizer are used in a weight ratio of 1:0.5 to 1:50, conveniently of 1:1 to 1:50. 9
7. A process according to any one of claims 1-6. wherein copper oxinate and solubilizer are used in a weight ratio of about 1:4 to 1:15.
8. A process according to any one of claims 1-7, wherein copper oxinate and solubilizer are used in a weight ratio of about 1:6 to about 1:10.
9. A process according to claim 1 for the manufacture of a copper oxinate solution in an organic o solvent, which process comprises diluting the mixture, which is obtained by mixing the copper oxinate with the 15 solubilizer, with the solvent or mixing the copper G q a oxinate, the solubilizer and the solvent with one another. optionally while heating. A process for the manufacture of a copper oxinate preparation, substantially as herein described with reference to any one of the foregoing Examples thereof. F DATED this 26th day of July, 1989 25 (lk- k Q 0-F-F--NN--A H-E- -A6- By Its Patent Attorneys ARTHUR S. CAVE CO. 711
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH288188 | 1988-07-28 | ||
| CH2881/88 | 1988-07-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3899089A AU3899089A (en) | 1990-02-01 |
| AU625875B2 true AU625875B2 (en) | 1992-07-16 |
Family
ID=4243684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU38990/89A Ceased AU625875B2 (en) | 1988-07-28 | 1989-07-26 | Solubilizing process for the manufacture of a copper oxinate preparation |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0355383A1 (en) |
| JP (1) | JPH0274524A (en) |
| AU (1) | AU625875B2 (en) |
| FI (1) | FI893597A (en) |
| NO (1) | NO893070L (en) |
| NZ (1) | NZ230025A (en) |
| PT (1) | PT91297B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010052260A (en) | 1998-04-17 | 2001-06-25 | 메이나드, 니겔 폴 | A biocidal composition containing phosphite ions |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2755280A (en) * | 1952-02-29 | 1956-07-17 | Geigy Chem Corp | Solubilization of metallic-8-quinolinolates |
| US3033865A (en) * | 1959-04-09 | 1962-05-08 | Augustus S Wittnebel | Solubilizing copper-8-quinolinolate |
| AU7175887A (en) * | 1986-04-18 | 1987-10-22 | Egis Gyogyszergyar | An organic zinc complex and its use as an antimycotic |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2608556A (en) * | 1950-07-10 | 1952-08-26 | Scient Oil Compounding Company | Preparation of a soluble metal quinolinolate |
-
1989
- 1989-07-15 EP EP89113003A patent/EP0355383A1/en not_active Ceased
- 1989-07-21 NZ NZ230025A patent/NZ230025A/en unknown
- 1989-07-26 AU AU38990/89A patent/AU625875B2/en not_active Ceased
- 1989-07-27 PT PT91297A patent/PT91297B/en not_active IP Right Cessation
- 1989-07-27 NO NO89893070A patent/NO893070L/en unknown
- 1989-07-27 FI FI893597A patent/FI893597A/en not_active IP Right Cessation
- 1989-07-27 JP JP1195380A patent/JPH0274524A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2755280A (en) * | 1952-02-29 | 1956-07-17 | Geigy Chem Corp | Solubilization of metallic-8-quinolinolates |
| US3033865A (en) * | 1959-04-09 | 1962-05-08 | Augustus S Wittnebel | Solubilizing copper-8-quinolinolate |
| AU7175887A (en) * | 1986-04-18 | 1987-10-22 | Egis Gyogyszergyar | An organic zinc complex and its use as an antimycotic |
Also Published As
| Publication number | Publication date |
|---|---|
| PT91297B (en) | 1995-03-01 |
| FI893597A0 (en) | 1989-07-27 |
| NZ230025A (en) | 1991-12-23 |
| PT91297A (en) | 1990-02-08 |
| NO893070L (en) | 1990-01-29 |
| AU3899089A (en) | 1990-02-01 |
| NO893070D0 (en) | 1989-07-27 |
| EP0355383A1 (en) | 1990-02-28 |
| JPH0274524A (en) | 1990-03-14 |
| FI893597A (en) | 1990-01-29 |
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