NO143528B - ANALOGY PROCEDURE FOR THE PREPARATION OF NEW HALOGENIC CYCLOPROPYL SUBSTITUTED PHENOXYLICAN ACIDS AND ALKYL ESTERS OR SALTS THEREOF - Google Patents
ANALOGY PROCEDURE FOR THE PREPARATION OF NEW HALOGENIC CYCLOPROPYL SUBSTITUTED PHENOXYLICAN ACIDS AND ALKYL ESTERS OR SALTS THEREOF Download PDFInfo
- Publication number
- NO143528B NO143528B NO3388/73A NO338873A NO143528B NO 143528 B NO143528 B NO 143528B NO 3388/73 A NO3388/73 A NO 3388/73A NO 338873 A NO338873 A NO 338873A NO 143528 B NO143528 B NO 143528B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- bath
- acids
- phenoxylican
- halogenic
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 10
- 150000002148 esters Chemical class 0.000 title claims description 3
- 150000007513 acids Chemical class 0.000 title description 3
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical group [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 title 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 8
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 235000021317 phosphate Nutrition 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- 238000010348 incorporation Methods 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- MVWDJLOUEUAWIE-UHFFFAOYSA-N O=C=O.O=C=O Chemical compound O=C=O.O=C=O MVWDJLOUEUAWIE-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000013527 degreasing agent Substances 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Bad til frembringelse av oksalatovertrekk med høy sjikttykkelse på metaller. Bath for producing oxalate coatings with a high layer thickness on metals.
Det er kjent at man kan øke sjiktvekten It is known that the layer weight can be increased
av fosfatovertrekk ved fremstillingen ved of phosphate coating in the production by
hjelp av oppløsninger av sjiktdannende using solutions of layer-forming
fosfater som har en pH-verdi fra 1,9 til 3,5 phosphates that have a pH value from 1.9 to 3.5
ved tilsetning av chelat- eller kompleiks-dannende organiske midler til de sure fos-fatoppløsnin.ger. Som slike virksomme stoffer kan spesielt nevnes a-aminosyrer og by adding chelating or complex-forming organic agents to the acidic phosphate solutions. As such active substances, α-amino acids and
polykarboksy-a-aminosyrer, eksempelvis polycarboxy-α-amino acids, for example
etylendiamintetraeddiksyre. ethylenediaminetetraacetic acid.
Ved påføring av oksalatovertrekk på When applying oxalate coating on
metalloverflater bevirker nærvær av slike metal surfaces cause the presence of such
chelat- eller kompleksdannende midler i chelating or complexing agents i
de vanlige oksalateringsoppløsninger der-imot ingen forandring av vekten resp. tyk-kelsen av disse oksialatsjikt. the usual oxalate solutions, on the other hand, no change in weight resp. the thickness of these oxyal layers.
Det er nu blitt funnet et bad til frem-stilling av oksalatovertrekk med høy sjikttykkelse på metaller, hvilket bad har en A bath has now been found for the production of oxalate coatings with a high layer thickness on metals, which bath has a
spesiell sammensetning. Badet ifølge oppfinnelsen inneholder på i og for seg kjent special composition. The bath according to the invention contains in and of itself known
måte oksalsyre, en eller flere oksyderende way oxalic acid, one or more oxidizing
akseleratorer, et innarbeidningsisalt eksempelvis jernsalt eller trioksalatokrom (III)-kalium, eventuelt aktivatorer, fosfater og/ accelerators, an incorporation salt, for example iron salt or trioxalatochrome (III)-potassium, possibly activators, phosphates and/
eller acetater, såvel som hertil ifølge oppfinnelsen polyvinylfosfonsyre og/eller et or acetates, as well as, according to the invention, polyvinylphosphonic acid and/or et
vannoppløselig blandingspolymeriisat av en water-soluble mixed polymer of a
alkenfosfonsyre med en umettet organisik alkenephosphonic acid with an unsaturated organic
forbindelse med en eller flere dobbeltbin-dinger. connection with one or more double bonds.
Dertil kommer det fortrinnsvis i be-traktning blandingspolymerisater av vinylfosfonsyre med akrylsyre, metakrylsyre eller deres estere, amider, nitriler, såvel som vinylestere, maleinsyreanhydrid eller kro-tonsyre. In addition, mixed polymers of vinylphosphonic acid with acrylic acid, methacrylic acid or their esters, amides, nitriles, as well as vinyl esters, maleic anhydride or crotonic acid are preferably taken into consideration.
Ved hjelp av oppløsningene ifølge oppfinnelsen lykkes det å fremstille sjikt hvis With the help of the solutions according to the invention, it is possible to produce layers if
tykkelse er betraktelig større enn de med de kjente oppløsninger frembragte sjikt. thickness is considerably greater than the layers produced with the known solutions.
Spesielt gunstige har polymerisatkon-sentrasjoner fra ca. 0,3 g/l til ca. 17 g/1, fortrinnsvis 0,7 g/l til 12 g/l, i oksalate-ringsoppløsningene vist seg. Polymer concentrations from approx. 0.3 g/l to approx. 17 g/l, preferably 0.7 g/l to 12 g/l, in the oxalate solutions proved.
De overtrekk som er påført ved hjelp av badet ifølge oppfinnelsen kan anvendes på mange måter. Mens eksempelvis på jern- eller ståltråd oksalatovertrekk som er påført ved hjelp av de vanlige oksalater-ingsoppløsninger ikke formår å beskytte metallet under formgivningen, fremfor alt ved flere gangers trekning gjennom dyser, viser oksalatsj iktene som er frembragt på trådene ved hjelp av badet ifølge oppfinnelsen, seg godt egnet selv for de høye krav, slik de stilles ved de høye tverrsnittsfor-minskelser som oppnås med få trekninger. The covers that are applied using the bath according to the invention can be used in many ways. While, for example, on iron or steel wire, oxalate coatings that are applied using the usual oxalating solutions do not manage to protect the metal during shaping, above all by drawing several times through nozzles, the oxalate layers produced on the wires using the bath according to the invention show , is well suited even for the high demands, as they are made by the high cross-sectional reductions that are achieved with few draws.
Setter man til oksalateringsoppløsnin-gen istedenfor homo- og/eller blamiings-polymerisatene av alkenfosfonsyrer en eller flere monomere alkenfosfonsyrer, spesielt vinylfosfonsyre og/eller deres sure de-rivater, så lar det seg ikke fstslå noen for-andringer av sjikttykkelsen i forhold til de overtrekk som er frembragt i de fosfon-syrefrie oppløsninger. If one adds to the oxalate solution instead of the homo- and/or blaming polymers of alkenephosphonic acids one or more monomeric alkenephosphonic acids, especially vinylphosphonic acid and/or their acidic derivatives, no changes in the layer thickness can be established in relation to the coatings produced in the phosphonic acid-free solutions.
Oksalatsjiktene fremstilt ved hjelp av badet ifølge oppfinnelsen lar seg frembringe på avfettede metalldeler, spesielt på jern-, stål- og aluminium-overflater på vanlig måte ved inndypning, strømning eller ved påsprøytning av oppløsningene. De spyles deretter med vann og tørkes. The oxalate layers produced using the bath according to the invention can be produced on degreased metal parts, especially on iron, steel and aluminum surfaces in the usual way by immersion, flow or by spraying the solutions. They are then rinsed with water and dried.
Badet ifølge oppfinnelsen skal i det følgende beskrives nærmere ved hjelp av noen eksempler. The bath according to the invention will be described in more detail in the following with the help of some examples.
Eksempel 1: Stålblikk av kvalltetsklasse St VIII be-handles på kjent måte med et handelsvan-lig alkalisk avfetningsmiddel i 10 minutter ved 95° C og spyles deretter med koldt vann. De dyppes deretter i 10 minutter i en oppløsning av følgende sammensetning: 15 g/l oksalsyredihydrat, 8 g/l natriumklorat, 5 g/l jern-(II) -suliatheptahydrat. Example 1: Steel sheet of hardness class St VIII is treated in a known manner with a commercially available alkaline degreaser for 10 minutes at 95° C and then rinsed with cold water. They are then dipped for 10 minutes in a solution of the following composition: 15 g/l oxalic acid dihydrate, 8 g/l sodium chlorate, 5 g/l iron (II) suliate heptahydrate.
Oppløsningen inneholder dessuten så mye alkalifosfat at det innstiller seg en pH-verdi på 1,9. Badtemperaturen utgjør ca. 18° C. The solution also contains so much alkali phosphate that a pH value of 1.9 is set. The bath temperature is approx. 18° C.
Til forskjellige deler av denne stam-oppløsning settes 0,8 resp. 1 resp. 3 resp. 15 g/l polyvinylfosfonsyre. Til ytterligere deler av den angitte oppløsning settes 1 resp. 4 g/l av et blandingspolymerisat (A) av vinylfosfonsyre med akrylsyre (mol.forhold: 80 : 20), såvel som 0,8 g/l resp. 1,9 g/l av et blandingspolymerisat (B) av vinylfosfonsyre med vinylacetat (mol.forhold 8o : 20). To different parts of this stock solution is added 0.8 resp. 1 or 3 or 15 g/l polyvinylphosphonic acid. To further parts of the specified solution, add 1 resp. 4 g/l of a mixed polymer (A) of vinylphosphonic acid with acrylic acid (molar ratio: 80 : 20), as well as 0.8 g/l resp. 1.9 g/l of a mixed polymer (B) of vinylphosphonic acid with vinyl acetate (molar ratio 80 : 20).
Til sammenligning tjener deler av stamoppløsnlngen som dessuten inneholder forskjellige mengder etylen-diamin-tetra-eddiksyre, tetranatriumetylendiamintetra-acetat, glycin eller monomer vinylfosfonsyre. For comparison, parts of the stock solution which also contain different amounts of ethylenediaminetetraacetic acid, tetrasodium ethylenediaminetetraacetate, glycine or monomeric vinylphosphonic acid serve.
Blikk som er oksalatert med disse opp-løsninger spyles med vann og tørkes med varmluft. Tin that has been oxalated with these solutions is rinsed with water and dried with hot air.
Deretter bestemmes oksalatovertrekke-nes sjikttykkelse. Resultatene som oppnås herved er sammenstilt i følgende tabell: The layer thickness of the oxalate coatings is then determined. The results obtained in this way are compiled in the following table:
Som det fremgår av tabellen bevirker tilsetninger av monomere vinylfosfonsyrer eller av stoffer som ved fosfatering fører til en økning av sjiktvekten ved oksalaterin-gen ingen forandring av sjikttykkelsen. As can be seen from the table, additions of monomeric vinylphosphonic acids or of substances which during phosphating lead to an increase in the layer weight of the oxalaterin cause no change in the layer thickness.
Eksempel 2: På den i eksempel 1 angitte måte av-fettes stålblikk av kvalitetsklasse ST VIII, spyles og utstyres ved værelsetemperatur med et fastklebende oksalatsjikt. Den hertil anvendte oksalateringsoppløsning har følgende sammensetning: 4 g/l oksalsyredihydrat, 2 g/l natriumklorat, 1 g/l K:( [Cr(C20,),] Example 2: In the manner specified in example 1, steel tin of quality class ST VIII is degreased, rinsed and equipped at room temperature with an adhesive oxalate layer. The oxalating solution used for this purpose has the following composition: 4 g/l oxalic acid dihydrate, 2 g/l sodium chlorate, 1 g/l K:( [Cr(C20,),]
De oksaliaterte blikk spyles med vann og tørkes med varmluft. Etter en inndyp-pinigstid på 8 minutter utgjør sjikttykkelsen 1,4 ).i. Setter man til den beskrevne oksalateringsoppløsning 1 g/l polyvinylfosfonsyre så får man ved samme behand-lingstid sjikt med en tykkelse på 2,8 \ x. The oxalated tins are rinsed with water and dried with hot air. After a soaking time of 8 minutes, the layer thickness amounts to 1.4).i. If 1 g/l of polyvinylphosphonic acid is added to the described oxalation solution, a layer with a thickness of 2.8 x is obtained at the same treatment time.
Claims (3)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28457772A | 1972-08-29 | 1972-08-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
NO143528B true NO143528B (en) | 1980-11-24 |
NO143528C NO143528C (en) | 1981-03-04 |
Family
ID=23090716
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO3388/73A NO143528C (en) | 1972-08-29 | 1973-08-28 | ANALOGY PROCEDURE FOR THE PREPARATION OF NEW HALOGENIC CYCLOPROPYL SUBSTITUTED PHENOXYLICAN ACIDS AND ALKYL ESTERS OR SALTS THEREOF |
Country Status (20)
Country | Link |
---|---|
JP (3) | JPS585175B2 (en) |
AR (1) | AR206596A1 (en) |
AT (1) | AT331207B (en) |
AU (1) | AU472631B2 (en) |
BE (1) | BE803924A (en) |
CA (1) | CA1023762A (en) |
CH (2) | CH605584A5 (en) |
DE (1) | DE2343606C2 (en) |
DK (1) | DK141366B (en) |
ES (1) | ES418283A1 (en) |
FI (1) | FI58629C (en) |
FR (1) | FR2197586B1 (en) |
GB (1) | GB1385828A (en) |
HK (1) | HK6980A (en) |
IL (1) | IL43026A (en) |
NL (1) | NL180004C (en) |
NO (1) | NO143528C (en) |
PH (1) | PH10530A (en) |
SE (1) | SE417828B (en) |
ZA (1) | ZA735748B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2471364A1 (en) * | 1979-12-11 | 1981-06-19 | Rhone Poulenc Agrochimie | NOVEL ANILINE DERIVATIVES AND COMPOSITIONS REGULATING PLANT GROWTH CONTAINING THEM |
US4691042A (en) * | 1983-06-24 | 1987-09-01 | The Dow Chemical Company | Preparation of monaoalkylated dihydroxybenzenes and novel compounds prepared thereby |
GB8330407D0 (en) * | 1983-11-15 | 1983-12-21 | Sterwin Ag | Halocyclopropyl-substituted phenoxyalkanoic acids and esters |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1121722A (en) * | 1966-03-31 | 1968-07-31 | Ici Ltd | New carboxylic acid derivatives |
BE754245A (en) * | 1969-08-01 | 1970-12-31 | Sumitomo Chemical Co | PHENOXY CARBOXYLIC ACID DERIVATIVES |
-
1973
- 1973-01-01 AR AR249792A patent/AR206596A1/en active
- 1973-08-13 GB GB3831173A patent/GB1385828A/en not_active Expired
- 1973-08-20 IL IL43026A patent/IL43026A/en unknown
- 1973-08-22 AU AU59488/73A patent/AU472631B2/en not_active Expired
- 1973-08-22 ZA ZA735748A patent/ZA735748B/en unknown
- 1973-08-22 FR FR7330434A patent/FR2197586B1/fr not_active Expired
- 1973-08-23 BE BE1005309A patent/BE803924A/en not_active IP Right Cessation
- 1973-08-24 PH PH14951A patent/PH10530A/en unknown
- 1973-08-27 CH CH959876A patent/CH605584A5/en not_active IP Right Cessation
- 1973-08-27 CH CH7312272A patent/CH608780A5/xx not_active IP Right Cessation
- 1973-08-27 AT AT744773A patent/AT331207B/en not_active IP Right Cessation
- 1973-08-28 NO NO3388/73A patent/NO143528C/en unknown
- 1973-08-28 ES ES418283A patent/ES418283A1/en not_active Expired
- 1973-08-28 DK DK471773AA patent/DK141366B/en not_active IP Right Cessation
- 1973-08-28 FI FI2675/73A patent/FI58629C/en active
- 1973-08-28 SE SE7311687A patent/SE417828B/en unknown
- 1973-08-28 CA CA179,829A patent/CA1023762A/en not_active Expired
- 1973-08-29 DE DE2343606A patent/DE2343606C2/en not_active Expired
- 1973-08-29 NL NLAANVRAGE7311903,A patent/NL180004C/en not_active IP Right Cessation
- 1973-08-29 JP JP48096261A patent/JPS585175B2/en not_active Expired
-
1980
- 1980-02-28 HK HK69/80A patent/HK6980A/en unknown
-
1982
- 1982-06-02 JP JP57094645A patent/JPS60335B2/en not_active Expired
- 1982-06-02 JP JP57094644A patent/JPS60334B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
NL180004C (en) | 1986-12-16 |
HK6980A (en) | 1980-03-07 |
CH608780A5 (en) | 1979-01-31 |
FI58629C (en) | 1981-03-10 |
FR2197586A1 (en) | 1974-03-29 |
JPS585175B2 (en) | 1983-01-29 |
DE2343606A1 (en) | 1974-03-07 |
PH10530A (en) | 1977-05-30 |
CH605584A5 (en) | 1978-09-29 |
AT331207B (en) | 1976-08-10 |
DK141366C (en) | 1980-09-01 |
AU472631B2 (en) | 1976-05-27 |
FR2197586B1 (en) | 1977-09-09 |
GB1385828A (en) | 1975-03-05 |
BE803924A (en) | 1974-02-25 |
NL180004B (en) | 1986-07-16 |
AR206596A1 (en) | 1976-08-06 |
CA1023762A (en) | 1978-01-03 |
NO143528C (en) | 1981-03-04 |
SE417828B (en) | 1981-04-13 |
ATA744773A (en) | 1975-11-15 |
ES418283A1 (en) | 1976-06-01 |
AU5948873A (en) | 1975-02-27 |
ZA735748B (en) | 1974-08-28 |
JPS60334B2 (en) | 1985-01-07 |
DK141366B (en) | 1980-03-03 |
IL43026A0 (en) | 1973-11-28 |
JPS5883649A (en) | 1983-05-19 |
FI58629B (en) | 1980-11-28 |
JPS60335B2 (en) | 1985-01-07 |
IL43026A (en) | 1977-01-31 |
JPS5874636A (en) | 1983-05-06 |
DE2343606C2 (en) | 1983-08-04 |
JPS4956958A (en) | 1974-06-03 |
NL7311903A (en) | 1974-03-04 |
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