NO161917B - ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE DERIVATIVES OF TIENO AND FURO (2,3-C) PYROLES. - Google Patents
ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE DERIVATIVES OF TIENO AND FURO (2,3-C) PYROLES. Download PDFInfo
- Publication number
- NO161917B NO161917B NO854051A NO854051A NO161917B NO 161917 B NO161917 B NO 161917B NO 854051 A NO854051 A NO 854051A NO 854051 A NO854051 A NO 854051A NO 161917 B NO161917 B NO 161917B
- Authority
- NO
- Norway
- Prior art keywords
- radical
- polyamide
- furo
- carbon atoms
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 230000001225 therapeutic effect Effects 0.000 title 1
- 239000004952 Polyamide Substances 0.000 claims description 30
- 229920002647 polyamide Polymers 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 19
- 239000000975 dye Substances 0.000 claims description 7
- 150000003951 lactams Chemical class 0.000 claims description 7
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 230000001965 increasing effect Effects 0.000 claims description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 5
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- WUACDRFRFTWMHE-UHFFFAOYSA-N 3,4-diaminocyclobut-3-ene-1,2-dione Chemical compound NC1=C(N)C(=O)C1=O WUACDRFRFTWMHE-UHFFFAOYSA-N 0.000 abstract 1
- BCWUZUYZBGMZFZ-UHFFFAOYSA-N 5h-furo[2,3-c]pyrrole Chemical class N1C=C2OC=CC2=C1 BCWUZUYZBGMZFZ-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000012634 fragment Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 238000009987 spinning Methods 0.000 description 10
- 239000000654 additive Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000003018 phosphorus compounds Chemical class 0.000 description 7
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- -1 heterocyclic amines Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 3
- 239000000980 acid dye Substances 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 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
- 150000001408 amides Chemical class 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
remstilling av tieno-og furo-[2,3-c]-pyrroler representert ved formelen. hvor Xog Xbetegner et oksygen-eller svovelatom; R. betegner et rettlinjet eller forgrenet alkylradikal som Inneholder fra 1 til 8 karbonatomer, et alkynylradikal, et alkoksyalkylradikal som inneholder fra 3 til 8 karbonatomer eller et aromatisk radikal; Rj betegner et hydrogenatom eller et rettlinjet eller forgrenet alkylradikal; m = 2 eller 3, når m = 2 betegner Xog Xet svovelatom, U representerer et 3,4-diamino-cyklobuten-l,2-dion- eller aminosulfonylformamidinradikal; U kan også representere en nitrogenstruktur. hvor V betegner et nitrogenatom eller et CH-fragment; W representerer NOeller CN; Rbetegner et hydrogenatom, et rettlinjet eller forgrenet alkylradikal på fra 1 til 8' karbonatomer, et alkynylradikal; Rbetegner en alkylgruppe som inneholder fra 1 til 3 karbonatomer.preparation of thieno and furo [2,3-c] pyrroles represented by the formula. wherein X and X represent an oxygen or sulfur atom; R. represents a straight or branched chain alkyl radical containing from 1 to 8 carbon atoms, an alkynyl radical, an alkoxyalkyl radical containing from 3 to 8 carbon atoms or an aromatic radical; R 1 represents a hydrogen atom or a straight or branched alkyl radical; m = 2 or 3, when m = 2 represents X and Xet sulfur atom, U represents a 3,4-diamino-cyclobutene-1,2-dione or aminosulfonylformamidine radical; U can also represent a nitrogen structure. wherein V represents a nitrogen atom or a CH fragment; W represents NO or CN; R represents a hydrogen atom, a straight or branched alkyl radical of from 1 to 8 'carbon atoms, an alkynyl radical; R represents an alkyl group containing from 1 to 3 carbon atoms.
Description
Fremgangsmåte til å øke farveopptagsevnen for sure farvestoffer for polyamider fra laktamer. Process for increasing the dye uptake capacity for acid dyes for polyamides from lactams.
Det er kjent at man kan forbedre It is known that one can improve
farveopptagsevnen for sure farvestoffer the dye absorption capacity for acid dyes
for polyamider når man sørger for at poly-amidene har et øket antall aminoendegrupper. Dette lar seg oppnå ved tilsetning for polyamides when it is ensured that the polyamides have an increased number of amino end groups. This can be achieved by addition
av frie1 amider til de polyamiddannende of free 1 amides to the polyamide-forming ones
utgangsstoffer før polykondensasjonen. Til starting materials before the polycondensation. To
de for dette formål anvendte aminer hører the amines used for this purpose belong
alifatiske mono- eller diaminer og hetero-cykliske aminer. Mens tilsetningen av slike aliphatic mono- or diamines and heterocyclic amines. While the addition of such
aminer til dikarbonsyrer og diaminer som amines to dicarboxylic acids and diamines which
polyamiddannende utgangsstoffer bare har polyamide-forming starting materials only have
ført til resultat i et lite overskudd, må led to a small profit, must
mengdene ved laktamer som1 monomere the amounts of lactams as1 monomers
være betraktelig større. Polyamider som be considerably larger. Polyamides such as
frembringes ved denne fremgangsmåte og produced by this method and
har et øket antall av aminoendegrupper, er has an increased number of amino end groups, is
imidlertid vanskelig å spinne. Når man vil however, difficult to spin. When you want
oppnå en merkbar forbedring av farvbar-heten og tilsette en følgelig større amin-mengde, tenderer polyamidmassen ved achieve a noticeable improvement in dyeability and add a correspondingly larger amount of amine, the polyamide mass tends to
spinning til drypping, dvs. en spinning er spinning to dripping, i.e. a spinning is
praktisk talt ikke lenger mulig. Etter en practically no longer possible. After one
kjent fremgangsmåte skal nu denne man-gel oppheves ved at man til polyamidet known method, this shortcoming must now be eliminated by adding the polyamide
før spinningen setter fosforforbindelser. before spinning sets phosphorus compounds.
Som egnede beskrives hypofosfitter av al-kali- og jordalkalimetaller såvel som av Hypophosphites of alkali-alkaline and alkaline-earth metals as well as of
sink, kadmium, mangan, aluminium og zinc, cadmium, manganese, aluminum and
tinn og salter av fosfinsyrer. tin and salts of phosphinic acids.
Ifølge en annen kjent fremgangsmåte According to another known method
skal farveaffiniteten ved polyamider økes the color affinity of polyamides must be increased
ved tilsetning av alkyl- eller arylfosfin-syrer, resp. deres aminsalter. Det vises at by adding alkyl or arylphosphinic acids, resp. their amine salts. It is shown that
tilsetningen av disse forbindelser, spesielt av aminsaltene av fosfinsyrer, har tilfølge en merkbar forbedring av farveopptagsevnen, mens metallsaltene av fosfinsyrer ikke frembringer noen effekt. Den kjente fremgangsmåte er imidlertid begrenset til polyamider av dikarbonsyrer og diaminer. Når man forsøker å overføre forskriften for arbeidsmåten til polyamider av laktamer, så fastslår man at den oppnåelige forbedring av farveaffiniteten bare er liten. the addition of these compounds, especially of the amine salts of phosphinic acids, results in a noticeable improvement in the color absorption capacity, while the metal salts of phosphinic acids produce no effect. However, the known method is limited to polyamides of dicarboxylic acids and diamines. When one tries to transfer the prescription for the working method to polyamides of lactams, it is determined that the achievable improvement in color affinity is only small.
Det er nu funnet at man vesentlig kan forbedre farveopptagsevnen ved polyamider av laktamer for sure farvestoffer ved tilsetningen av organiske fosforforbindelser It has now been found that the dye absorption capacity of polyamides of lactams for acid dyes can be significantly improved by the addition of organic phosphorus compounds
når man anvender 0,05—3 vektpst. av en when using 0.05-3% by weight. of one
fosfor- eller fosfonsyreester sammen med 0,02—0,5 vektpst. av en amin med den eenerelle formel phosphorous or phosphonic acid ester together with 0.02-0.5 wt. of an amine of the general formula
hvori n betyr 2—5 og m betyr 0—3. where n means 2-5 and m means 0-3.
De beste resultater oppnår man med aminer av den ovennevnte formel', hvor n er 2 og mi er 1—3, spesielt med dietylentriamin såvel som trietylentetramin eller tet-raetylenpentamin. The best results are obtained with amines of the above formula', where n is 2 and mi is 1-3, especially with diethylenetriamine as well as triethylenetetramine or tetraethylenepentamine.
Fosforforbindelser og aminer kan settes til laktamer før eller ved et egnet tids-punkt under polykondensasjonen. Det er dessuten mulig til det ferdige polyamid som foreligger i kutt- eller pulverform, å tilfolande tilsetningene før spinningen, f. eks. ved «panering» av kuttene. Phosphorous compounds and amines can be added to lactams before or at a suitable point in time during the polycondensation. It is also possible to add additives to the finished polyamide, which is available in cut or powder form, before spinning, e.g. by "breading" the cuts.
Som fosforforbindelser som kan anvendes ifølge oppfinnelsen kommer det på tale fosfor- eller fosfonsyreestere av de generelle formler Phosphorus compounds that can be used according to the invention include phosphorous or phosphonic acid esters of the general formulas
hvori X betyr en aryl- eller alkylrest og Y betyr en aryl- eller alkylrest eller hydro-gen. wherein X means an aryl or alkyl residue and Y means an aryl or alkyl residue or hydrogen.
Når man for å øke farveaffiniteten ved polyamider av laktamer bare tilsetter en fosfor- eller fosfonsyreester, så inntrer det allerede en, skjønt forholdsvis liten, effekt, mens dette ikke er tilfelle ved de kjente fosfinsyrer, resp. fosfinsyrederivater. Det lykkes imidlertid heller ikke med fosforforbindelsene som skal anvendes ifølge oppfinnelsen å forsterke denne effekt ved tilsetning av tilsvarende større mengder uten samtidig å nedsette polyamidets viskositet. Når man derimot anvender en fosfor- eller fosfonsyreester sammen med en mindre mengde av di- eller polyaminet, så øker farveopptagsevnen sterkt. Skjønt aminene, likeledes som fosforforbindelsene, virker viskositetsnedsettende, kan man ved egnet kombinasjon av fosforforbindelser og aminer såvel som ved valg av tilsetnings-menigder oppnå en optimal forbedring av farveaffiniteten ved minst mulig nedsettel-se av viskositeten. Her byr spesielt aminer av nevnte generelle formel, hvori m er 1—3, store fordeler fordi de allerede i meget små mengder viser en sterk innvirkning på polyamidenes farvemessige forholdi, og disse mengder har bare en liten innvirkning på viskositeten. When, in order to increase the color affinity of polyamides of lactams, only a phosphoric or phosphonic acid ester is added, there is already an, albeit relatively small, effect, while this is not the case with the known phosphinic acids, resp. phosphinic acid derivatives. However, the phosphorus compounds to be used according to the invention also do not succeed in enhancing this effect by adding correspondingly larger quantities without at the same time reducing the viscosity of the polyamide. When, on the other hand, a phosphoric or phosphonic acid ester is used together with a smaller amount of the di- or polyamine, the color absorption capacity increases greatly. Although the amines, as well as the phosphorus compounds, have a viscosity-reducing effect, with a suitable combination of phosphorus compounds and amines as well as with the choice of additive quantities, an optimal improvement of the color affinity can be achieved with the least possible reduction in viscosity. Here, in particular, amines of the aforementioned general formula, in which m is 1-3, offer great advantages because even in very small quantities they show a strong effect on the color ratio of the polyamides, and these quantities only have a small effect on the viscosity.
En ytterligere forholdsregel som fører til oppnåelse av spesielt gunstige resultater er tilsetning av fosforforbindelse og amin til det ferdige polyamid. Ved denne gjennomføringsform av fremgangsmåten influeres polyamidets viskositet knapt. Det er da overraskende at farveopptagsevnens forbedring er betraktelig. Dette var spesielt ved kjennskap til kjente fremgangs-måter ikke å forutse, for disse går ut fra at for å øke antallet av aminoendegrupper og dermed farveaffiniteten må tilsetnings-stoffene, og spesielt aminene, ubetinget settes til de polyamiddannende utgangsstoffer. A further precaution which leads to the achievement of particularly favorable results is the addition of a phosphorus compound and amine to the finished polyamide. In this form of implementation of the method, the viscosity of the polyamide is hardly influenced. It is therefore surprising that the improvement in color absorption is considerable. This was not to be foreseen, especially with knowledge of known methods, because these assume that in order to increase the number of amino end groups and thus the color affinity, the additives, and especially the amines, must be added unconditionally to the polyamide-forming starting materials.
Fremgangsmåten skal forklares nær-mere ved hjelp av eksempler. A) Man polykondenserer kaprolaktam på kjent måte og tilsetter til den flytende monomer 1 vektdel etanfosfonsyreester og 0,3 vektdeler dietylentriamin. Det dannede polyamid har en oppløsningsviskositet på 2,05 og er godt spinnbart. (Oppløsnings-viskositeten bestemmes ved måling av gjennomstrømningshastigheten av en 1 pst.-ig oppløsning av polyamidet i maur-syre.) For å fastslå den oppnådde farveforbedring farves tråder av det de ovennevnte tilsetninger inneholdende polyamid sammen med polyamidtråder som ikke inneholder tilsetninger, i samme bad med «Antralanblå B». Det av de to trådprøver opptatte farvestoff utvaskes deretter full-stendig med en pyridin-vannblanding. Man måler de to farvestoffløsningers ekstink-sjon hvis forhold utgjør 1:3,8 (polyamid uten tilsetning : polyamid + fosforforbindelse og amin). The procedure shall be explained in more detail by means of examples. A) Caprolactam is polycondensed in a known manner and 1 part by weight of ethanephosphonic acid ester and 0.3 parts by weight of diethylenetriamine are added to the liquid monomer. The polyamide formed has a solution viscosity of 2.05 and is easily spinnable. (The solution viscosity is determined by measuring the flow rate of a 1% solution of the polyamide in formic acid.) To determine the color improvement achieved, threads of the above-mentioned additives containing polyamide are dyed together with polyamide threads that do not contain additives, in the same bathroom with "Antralan blue B". The dye taken up by the two thread samples is then completely washed out with a pyridine-water mixture. One measures the extinction of the two dye solutions whose ratio is 1:3.8 (polyamide without addition: polyamide + phosphorus compound and amine).
Som beskrevet i eksempel A gjennom-føres ytterligere forsøk under forandring av de i følgende tabell angitte betingelser. As described in example A, further tests are carried out while changing the conditions indicated in the following table.
<*>) = Sammenligningsforsøk. ;B) Spinneferdig tørket polyamidkutt av kaprolaktam med en oppløsningsviskosi-tet på 2,55 blandes i en Taumel-tørker etter hverandre med 0,3 vektprosent hek-sametylendiamin og 1 vektpst. tributyl-fosfat. Deretter omgranuleres disse kutt i en ekstruder. Etter omgranuleringen må-les oppløsriingsviskositeten på 2,53. Kuttene spinnes deretter og de dannede tråder farves som beskrevet i eksempel A. Ved måling av ekstinksjonsforholdet av de av trådprøvene opptatte farvestoffmengder ;fastslås den oppnådde farveforbedring i forhold til ikke modifisert polyamid. Ékstinksjonsforholdet utgjør 1:2,63 (polyamid uten tilsetning : polyamid og fosforforbindelser og amin). ;Som beskrevet i eksempel B gjennom-føres ytterligere forskjell under forandring av de i tabellen angitte forbindelser, resp. tilseitoinigsmengder. ;En ytterligere fordel ved fremgangsmåten ifølge oppfinnelsen må ses deri .at tilsetning av fosforforbindelsene under ;<*>) = Sammenligningsforsøk. <*>) = Comparison test. ;B) Ready-to-spin dried polyamide cut from caprolactam with a solution viscosity of 2.55 is mixed in a Taumel dryer one after the other with 0.3% by weight of hexamethylenediamine and 1% by weight. tributyl phosphate. These cuts are then re-granulated in an extruder. After re-granulation, the dissolution viscosity of 2.53 must be read. The cuts are then spun and the threads formed are dyed as described in example A. By measuring the extinction ratio of the amounts of dye taken up by the thread samples, the achieved color improvement in relation to unmodified polyamide is determined. The extinction ratio amounts to 1:2.63 (polyamide without addition: polyamide and phosphorus compounds and amine). As described in example B, a further difference is carried out by changing the compounds indicated in the table, resp. tilseitoinig quantities. A further advantage of the method according to the invention must be seen in that addition of the phosphorus compounds under (<*>) = Comparison test.
spinningeni utløser en betraktelig etter-kondensasjon således at det også da, når the spinning triggers considerable after-condensation so that it also then, when
oppløsningsviskositeten av tilsetningshol-dige kutt i forhold til normal polyamid er the solution viscosity of additive-containing cuts compared to normal polyamide is
noe lavere, inntrer i spinneprosessen en somewhat lower, enters the spinning process one
økning av viskositeten således at også i increase in viscosity so that also i
disse tilfeller er det sikret en tilstrekkelig in these cases, a sufficient
høy viskositet av de ferdige tråder («Ge-■wølleviskositet»). Aminets tilsetning hind-rer som viskositetstabilisator at økningen high viscosity of the finished threads ("Ge-■wølle viscosity"). The addition of the amine as a viscosity stabilizer prevents the increase
av «Gewølleviskositet» under spinneprosessen antar en for stor grad. Også denne of "Gewølle viscosity" during the spinning process assumes an excessive degree. Also this one
effekt lar seg, som følgende eksempler effect is possible, as the following examples
viser tydelig belegge. shows clear coating.
C) Dette eksempels forsøk ble gjennom- C) This example's experiment was through-
ført for å vise at fosforsyreesterholdig polyamid av kaprolaktam under spinningen også underligger en betraktelig etterkon-densasjon når kuttene inneholder amin. led to show that phosphoric acid ester-containing polyamide of caprolactam during spinning is also subject to considerable post-condensation when the cuts contain amine.
Polyamidkutt som inneholder de av tabell C angitte tilsetninger spinnes med en eksitruderspinnemaskin ved en tempe-ratur på 275°C. Av de anvendelsesferdige kutt og «Gewølleprøvene» ble det på den i eksempel A beskrevne måte bestemt opp-løsningsviskositeten. Ved den høye økning av oppløsningsviskositeten under spinningen økes fosfonsyreesterens og aminets oppløsningsviskositets nedsettende effekt under polymerisasjonen. Polyamide cuts containing the additives specified in Table C are spun with an extruder spinning machine at a temperature of 275°C. From the ready-to-use cuts and the "Gewølle samples", the solution viscosity was determined in the manner described in example A. The high increase in solution viscosity during spinning increases the reducing effect of the solution viscosity of the phosphonic acid ester and the amine during polymerization.
Claims (2)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8415658A FR2571723B1 (en) | 1984-10-12 | 1984-10-12 | THIENO AND FURO- (2,3-C) PYRROLES DERIVATIVES, METHODS OF PREPARATION AND MEDICAMENTS CONTAINING THEM |
Publications (3)
Publication Number | Publication Date |
---|---|
NO854051L NO854051L (en) | 1986-04-14 |
NO161917B true NO161917B (en) | 1989-07-03 |
NO161917C NO161917C (en) | 1989-10-11 |
Family
ID=9308598
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO854051A NO161917C (en) | 1984-10-12 | 1985-10-11 | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE DERIVATIVES OF TIENO AND FURO (2,3-C) PYROLES. |
Country Status (19)
Country | Link |
---|---|
EP (1) | EP0180500A1 (en) |
JP (1) | JPS6197286A (en) |
AU (1) | AU593776B2 (en) |
CA (1) | CA1250847A (en) |
CS (1) | CS265211B2 (en) |
DD (1) | DD237662A5 (en) |
DK (1) | DK465685A (en) |
ES (1) | ES8605524A1 (en) |
FR (1) | FR2571723B1 (en) |
HU (1) | HU193827B (en) |
IL (1) | IL76619A (en) |
IN (1) | IN169684B (en) |
MA (1) | MA20543A1 (en) |
NO (1) | NO161917C (en) |
OA (1) | OA08119A (en) |
PT (1) | PT81282B (en) |
SU (1) | SU1329621A3 (en) |
YU (1) | YU162485A (en) |
ZA (1) | ZA857809B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60255756A (en) * | 1984-06-01 | 1985-12-17 | Ikeda Mohandou:Kk | Aminoalkylphenoxy derivative |
FR2733750B1 (en) * | 1995-05-03 | 1997-06-13 | Synthelabo | DERIVATIVES OF GAMMA-OXO-ALPHA- (PHENYLMETHYL) -5,6- DIHYDRO-4H-THIENO (3,4-C) PYRROLE-5-BUTANOIQUE, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
JP4596915B2 (en) | 2002-09-06 | 2010-12-15 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Thienopyrrolyl and furanopyrrolyl compounds and their use as histamine H4 receptor ligands |
CN101186612B (en) * | 2006-11-15 | 2012-10-03 | 天津和美生物技术有限公司 | Pyrroline derivative capable of inhibiting cell to release tumor necrotic factor and its preparation and application |
EP4196793A1 (en) | 2020-08-11 | 2023-06-21 | Université de Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
GB1601459A (en) * | 1977-05-17 | 1981-10-28 | Allen & Hanburys Ltd | Aminoalkyl thiophene derivatives |
US4390701A (en) * | 1981-05-18 | 1983-06-28 | Bristol-Myers Company | 1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione |
US4520025A (en) * | 1982-07-21 | 1985-05-28 | William H. Rorer, Inc. | Bicyclic nitrogen heterocyclic ethers and thioethers, and their pharmaceutical uses |
-
1984
- 1984-10-12 FR FR8415658A patent/FR2571723B1/en not_active Expired
-
1985
- 1985-10-04 EP EP85401941A patent/EP0180500A1/en not_active Withdrawn
- 1985-10-04 CS CS857144A patent/CS265211B2/en unknown
- 1985-10-08 MA MA20767A patent/MA20543A1/en unknown
- 1985-10-09 ZA ZA857809A patent/ZA857809B/en unknown
- 1985-10-09 IL IL76619A patent/IL76619A/en unknown
- 1985-10-10 PT PT81282A patent/PT81282B/en not_active IP Right Cessation
- 1985-10-10 DD DD85281615A patent/DD237662A5/en not_active IP Right Cessation
- 1985-10-11 YU YU01624/85A patent/YU162485A/en unknown
- 1985-10-11 JP JP60225005A patent/JPS6197286A/en active Pending
- 1985-10-11 AU AU48528/85A patent/AU593776B2/en not_active Ceased
- 1985-10-11 NO NO854051A patent/NO161917C/en unknown
- 1985-10-11 SU SU853963352A patent/SU1329621A3/en active
- 1985-10-11 CA CA000492893A patent/CA1250847A/en not_active Expired
- 1985-10-11 HU HU853957A patent/HU193827B/en not_active IP Right Cessation
- 1985-10-11 OA OA58701A patent/OA08119A/en unknown
- 1985-10-11 DK DK465685A patent/DK465685A/en not_active Application Discontinuation
- 1985-10-11 ES ES547789A patent/ES8605524A1/en not_active Expired
- 1985-10-22 IN IN881/DEL/85A patent/IN169684B/en unknown
Also Published As
Publication number | Publication date |
---|---|
JPS6197286A (en) | 1986-05-15 |
HU193827B (en) | 1987-12-28 |
ES547789A0 (en) | 1986-03-16 |
CA1250847A (en) | 1989-03-07 |
YU162485A (en) | 1987-12-31 |
ES8605524A1 (en) | 1986-03-16 |
NO161917C (en) | 1989-10-11 |
IL76619A (en) | 1990-07-12 |
NO854051L (en) | 1986-04-14 |
DD237662A5 (en) | 1986-07-23 |
ZA857809B (en) | 1986-05-28 |
EP0180500A1 (en) | 1986-05-07 |
IL76619A0 (en) | 1986-02-28 |
IN169684B (en) | 1991-12-07 |
CS714485A2 (en) | 1988-08-16 |
DK465685D0 (en) | 1985-10-11 |
AU4852885A (en) | 1986-04-17 |
PT81282B (en) | 1988-02-17 |
SU1329621A3 (en) | 1987-08-07 |
FR2571723B1 (en) | 1988-08-26 |
PT81282A (en) | 1985-11-01 |
HUT40133A (en) | 1986-11-28 |
DK465685A (en) | 1986-04-13 |
CS265211B2 (en) | 1989-10-13 |
FR2571723A1 (en) | 1986-04-18 |
MA20543A1 (en) | 1986-07-01 |
OA08119A (en) | 1987-03-31 |
AU593776B2 (en) | 1990-02-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5917004A (en) | Weather-resistant polyamides and method of their production | |
US3514498A (en) | Antistatic synthetic resin composition containing a polyether - polyamide block copolymer wherein an ionic functional group is made to coexist | |
US7074851B2 (en) | Method for making stabilised polyamide compositions | |
KR20010041746A (en) | Light and thermally stable polyamide | |
BG64908B1 (en) | Inherently light- and heat-stabilized polyamides with improved wet fastness | |
NO161917B (en) | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE DERIVATIVES OF TIENO AND FURO (2,3-C) PYROLES. | |
EA001451B1 (en) | Fibres of strongly branched polyamide | |
US3773739A (en) | Basic polyamides and process for their preparation | |
US3437641A (en) | Process for improving the acid dye receptivity of polylactams and polylactam products so produced | |
US3448087A (en) | Modified polycarbonamides | |
JPH0977865A (en) | Polyamide resin of random copolymer and its production | |
US3463847A (en) | Method of producing improved polyamidic fibrous material having three dimensional crimpability | |
US3304290A (en) | Synthetic linear polycarbonamides having an improved receptivity for acid dyes | |
GB1478221A (en) | Method of preparing polyamide fibres | |
US3530099A (en) | Synthetic linear polycarbonamides having an improved receptivity for acid dyes | |
KR860000347B1 (en) | Method of producing for polyamide of improved dyeability | |
US3767609A (en) | Process for the salt free manufacture of articles from linear aromatic polyamides in a lactam solvent | |
JP2002054025A (en) | Polyamide resin composition for fiber and polyamide fiber | |
US6074749A (en) | Acid dyeable fibre | |
NO131391B (en) | ||
DE2402930A1 (en) | Polyamide compsns. for fibre mfr. - contg. substd. amide additives to prevent gel formation in the melt | |
US3235533A (en) | Synthetic linear polycarbonamides containing sulfonic acids and having an improved receptivity for acid dyes | |
DE1905102A1 (en) | Modified polyamides with increased affinity for acidic dyes | |
US3471590A (en) | Synthetic fiber-forming polyamides containing piperazine polyamides | |
CN117285818A (en) | Polyamide composition and application thereof to high-strength transparent polyamide monofilament |