DE735010C - Process for the production of nitrogen-containing condensation products - Google Patents
Process for the production of nitrogen-containing condensation productsInfo
- Publication number
- DE735010C DE735010C DEZ25306D DEZ0025306D DE735010C DE 735010 C DE735010 C DE 735010C DE Z25306 D DEZ25306 D DE Z25306D DE Z0025306 D DEZ0025306 D DE Z0025306D DE 735010 C DE735010 C DE 735010C
- Authority
- DE
- Germany
- Prior art keywords
- production
- condensation products
- nitrogen
- products
- acids
- 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.)
- Expired
Links
- 239000007859 condensation product Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 4
- -1 aliphatic halocarboxylic acids Chemical class 0.000 claims description 4
- 230000017854 proteolysis Effects 0.000 claims description 3
- 239000007857 degradation product Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 7
- 235000018102 proteins Nutrition 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 239000002253 acid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
- 235000021240 caseins Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical class OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000003977 halocarboxylic acids Chemical class 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Peptides Or Proteins (AREA)
Description
Verfähren zur Herstellung; -von stickstoffhaltigen Kondensationsprodukten Gegenstand der vorliegenden Erfindung ist ein Verfahren. zur Herstellung von stickstoffhaltigen Kondensationsprodukten, welches darin besteht, daß man höhennolekularc Eiweißabbaupr odukte, die in an sich bekannter Weise auf alkalischem, saurem oder enzymatischem Wege aus °Proteinen, wie Leim, Casein, Gelatine, Haut- und Lederabfällen, erhältlich sind, mit niedrigmolekularen- alipliatischen Halogencarbonsäuren, zweckmäßig Snit co-Halogencarbonsäuren, in alkalischem Medium umsetzt.Method of manufacture; -of nitrogen-containing condensation products The present invention relates to a method. for the production of nitrogenous Condensation products, which consists in the fact that one hight molecular protein degradation pr oducts which, in a manner known per se, are alkaline, acidic or enzymatic Ways from ° proteins such as glue, casein, gelatin, skin and leather waste are available are, with low molecular weight aliphatic halocarboxylic acids, appropriate Snit co-halocarboxylic acids, implemented in an alkaline medium.
Man hat bereits hochmolekulare Fettsäurechloride bzw. Halo! enfettsäurechloTide mit Eiweißstoffen oder deren Abkömmlingen umgesetzt und stark oberflächenaktive, seifenartige ,Produkte erhalten.You already have high molecular weight fatty acid chlorides or halo! enfatty acid chlorides reacted with proteins or their derivatives and highly surface-active, soapy, products obtained.
Außerdem hat man- Halogenkohlenwasserstoffe mit Eiweißkörpern kondensiert. Man liat ferner vorgeschlagen, Ester -und Amide von a-Halogenfettsäuren mit Eiweißabbauprödukten zu kondensieren u:iid ist zu Reinigungsmitteln gelangt, die auch in saurem Medium beständig sind und dort ihre oberflächenaktiven Eigenschaften behalten. Main hat Halogencarbonsäuren und Halagencarbansäurechloride mit nativem Eiweiß zwecks Herstellung von Antigenen für die Serumtherapie umgesetzt, und durch Behandeln von Proteinen mit Halogencarbonsäuren hat man die Quellung und Koagulation von Eiweißkörpern untersucht.In addition, halogenated hydrocarbons have been condensed with protein bodies. It has also been proposed to use esters and amides of α-halogen fatty acids with protein degradation products to condense u: iid has reached cleaning agents that are also in an acidic medium are stable and retain their surface-active properties there. Main has Halocarboxylic acids and Halagencarbansäurechloride with native protein for the purpose of production converted by antigens for serum therapy, and by treating proteins The swelling and coagulation of protein bodies has been investigated using halocarboxylic acids.
Ferner hat man zur Herstellung von Iminodicarbonsäuren aus konfgurativen Zwecken bereits-optisch aktive-Aminocarbonsäuren mit Chloressigsäure umgesetzt und die entstandenen Iminodicarbonsäuren auf ihre optische Aktivität untersucht.Furthermore, one has to prepare iminodicarboxylic acids from confgurative Purposes already-optically active-aminocarboxylic acids reacted with chloroacetic acid and the resulting iminodicarboxylic acids examined for their optical activity.
Aus allen' diesen Verfahren ist nicht ersichtlich, daß man neue wertvolle Verbindungen erhalten kann, wenn man weitere- Carboxylbrruppen in die Eiweißspaltprodukte einfühT t, indem > man sie mit niedrigmolekularen aliphatischen Halogencarbonsäuren, zweckmäßig mit ou-Halogencaxbonsäuren,osin älkalischem Medium umsetzt. Die auf diese Weise erhaltenen Produkte sind weder aberüächenaktiv noch können sie als Antigene verwendet werden. Vielmehr war überraschend, daß durch die Vermehrung der Carboxylr uppen, die an sich als kalk-seifenbildende Gruppen bekannt sind, Stoffe erhalten werden, die die Bildung schwer löslicher Metallsalze von Seifen oder seifenartigen Verbindungen, wie z. B. von 'Türläschrotölen, Fettalkoholsulfonaten u. ,d.-"1., verhindern bzw. bereits gebildete schwer lösliche Metallsalze auflösen können. Beispiel i io Teile Caselnabbauprodukte, die durch Behandlung von Casein mit konzentrierter Salzsäure bei Kochtemperatur erhalten worden sind, werden in alkelischer Lösung mit io Teilen f-Chlorpropionsäure bei gewöhnlicher Temperatur verrührt, wobei darauf geachtet wird, daß die Alkalität bis zum Schluß der Umsetzung erhalten bleibt. Die Lösung kann als solche verwendet werden. Man kann sie aber auch einem der üblichen Trocknungsverfahren unterwerfen; man erhält auf diese Weise Trockenerzeugnisse, die mehr oder weniger große Mengen an unwirksamen Begleitstoffen enthalten. Um Trockenerzeugnisse zu gewinnen, die hiervon frei sind, kann man so vorgehen, daß man die Lösungen, in denen die Kondensation vorgenommen ist, zunächst ansäuert, die dadurch ausgeschiedenen sauren Kondensationsprodukte abtrennt, neutralisiert und dann die so erhaltenen Lösungen einem Trocknunngsverfahren unterwirft. -Beispiel z io Teile durch Hydrolyse von Lederabfällen erhaltenes trockenes Antinosäuregemisch werden mit 2o Teilen Chloressigsäure in alkalischer Lösung bei gewöhnlicher Temperatur verrührt, wobei darauf geachtet wird, daß die Alkalität bis zum Schluß der Umsetzung erhalten bleibt. Die Lösung kann als solche verwendet oder einem bekannten. Trocknungsverfahren unterworfen und d<1nn als Trockenprodukt verwendet werden.It is not evident from all of these procedures that new valuable ones can be obtained Compounds can be obtained if one further carboxyl groups in the protein breakdown products by> combining them with low molecular weight aliphatic halocarboxylic acids, expediently reacted with ou-halocaxboxylic acids, osin alkaline medium. The on this way obtained products are neither surface active nor can they are used as antigens. Rather, it was surprising that through the increase the carboxyl groups, which are known per se as lime-soap-forming groups, substances can be obtained that the formation of poorly soluble metal salts of soaps or soap-like Connections such as B. of 'Türläschrotölen, Fettalkoholsulfonaten u., D .- "1., prevent or dissolve already formed poorly soluble metal salts. example i io parts of casein breakdown products obtained by treating casein with concentrated Hydrochloric acid obtained at boiling temperature are in alkaline solution stirred with 10 parts of f-chloropropionic acid at ordinary temperature, with on it care is taken that the alkalinity is retained until the end of the reaction. the Solution can be used as such. But you can also use one of the usual ones Subject to drying procedures; dry products are obtained in this way, which contain more or less large amounts of ineffective accompanying substances. To dry products to win who are free of this, one can proceed in such a way that one finds the solutions, in which the condensation is carried out, first acidifies the thereby excreted acidic condensation products are separated off, neutralized and then the resulting Subjecting solutions to a drying process. -Example z io parts by hydrolysis Dry antinoic acid mixture obtained from leather waste is mixed with 20 parts of chloroacetic acid stirred in alkaline solution at ordinary temperature, being careful is that the alkalinity is retained until the end of the reaction. The solution can be used as such or a known one. Subjected to drying processes and d <1nn can be used as the dry product.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEZ25306D DE735010C (en) | 1939-05-28 | 1939-05-28 | Process for the production of nitrogen-containing condensation products |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEZ25306D DE735010C (en) | 1939-05-28 | 1939-05-28 | Process for the production of nitrogen-containing condensation products |
Publications (1)
Publication Number | Publication Date |
---|---|
DE735010C true DE735010C (en) | 1943-05-04 |
Family
ID=7626346
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEZ25306D Expired DE735010C (en) | 1939-05-28 | 1939-05-28 | Process for the production of nitrogen-containing condensation products |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE735010C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE961540C (en) * | 1952-10-25 | 1957-04-11 | Chem Fab Gruenau Ag | Process for the production of surface-effective protein condensation products |
-
1939
- 1939-05-28 DE DEZ25306D patent/DE735010C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE961540C (en) * | 1952-10-25 | 1957-04-11 | Chem Fab Gruenau Ag | Process for the production of surface-effective protein condensation products |
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