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 PDF

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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
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Prior art keywords
acid
bath
acids
phenoxylican
halogenic
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NO3388/73A
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Norwegian (no)
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NO143528C (en
Inventor
Donald Kenney Phillips
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Sterling Drug Inc
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Publication of NO143528B publication Critical patent/NO143528B/en
Publication of NO143528C publication Critical patent/NO143528C/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/76Unsaturated compounds containing keto groups
    • C07C59/90Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/58Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/72Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings

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  • 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)

1. Bad til frembringelse av oksaHat-overtrekk med høy sjikttykkelse på metaller, hvilket bad inneholder oksalsyre, en eller flere oksyderende akseleratorer, et innarbeidningssalt og eventuelt aktivatorer, fosfater og/eller acetater, <ka rakte-risiert ved at badet dessuten inneholder polyvinylfosfonsyre og/eller et vann-oppløselig blandingspolymerisat av en alkenfosfonsyre med en umettet organisk forbindelse med en eller flere dobbeltbindin-ger.1. Bath for producing oxaHat coatings with a high layer thickness on metals, which bath contains oxalic acid, one or more oxidizing accelerators, an incorporation salt and possibly activators, phosphates and/or acetates, characterized in that the bath also contains polyvinylphosphonic acid and /or a water-soluble mixed polymer of an alkenephosphonic acid with an unsaturated organic compound with one or more double bonds. 2. Bad ifølge påstand 1, karakterisert ved at det sammen med polyvinylfosfonsyre eller alene inneholder et vann-oppløselig blandingspolymerisat av vinylfosfonsyre med akrylsyre, metakrylsyre eller deres estere, amider, nitriler eller vinylestere, maleinsyreanhydrid eller kroton-syre.2. Bath according to claim 1, characterized in that, together with polyvinylphosphonic acid or alone, it contains a water-soluble mixed polymer of vinylphosphonic acid with acrylic acid, methacrylic acid or their esters, amides, nitriles or vinyl esters, maleic anhydride or crotonic acid. 3. Bad ifølge påstandene 1 og 2, karakterisert ved at det inneholder 0,3 til 17 g/l, fortrinnsvis 0,7 til 12 g/l poly-merisat.3. Bath according to claims 1 and 2, characterized in that it contains 0.3 to 17 g/l, preferably 0.7 to 12 g/l polymer.
NO3388/73A 1972-08-29 1973-08-28 ANALOGY PROCEDURE FOR THE PREPARATION OF NEW HALOGENIC CYCLOPROPYL SUBSTITUTED PHENOXYLICAN ACIDS AND ALKYL ESTERS OR SALTS THEREOF NO143528C (en)

Applications Claiming Priority (1)

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US28457772A 1972-08-29 1972-08-29

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NO143528B true NO143528B (en) 1980-11-24
NO143528C NO143528C (en) 1981-03-04

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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)

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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

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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

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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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