DE925496C - Process for making super polymeric compounds - Google Patents

Process for making super polymeric compounds

Info

Publication number
DE925496C
DE925496C DED4183D DED0004183D DE925496C DE 925496 C DE925496 C DE 925496C DE D4183 D DED4183 D DE D4183D DE D0004183 D DED0004183 D DE D0004183D DE 925496 C DE925496 C DE 925496C
Authority
DE
Germany
Prior art keywords
cyclohexane
acid
polymeric compounds
super
making super
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
Application number
DED4183D
Other languages
German (de)
Inventor
Winfried Dr Hentrich
Alfred Dr Kirstahler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DEHYDAG GmbH
Dehydag Deutsche Hydrierwerke GmbH
Original Assignee
DEHYDAG GmbH
Dehydag Deutsche Hydrierwerke GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by DEHYDAG GmbH, Dehydag Deutsche Hydrierwerke GmbH filed Critical DEHYDAG GmbH
Priority to DED4183D priority Critical patent/DE925496C/en
Application granted granted Critical
Publication of DE925496C publication Critical patent/DE925496C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyamides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung superpolymerer Verbindungen Da.s Patent 92424o betrifft ein Verfahren zur Herstellung superpolymerer Verbindungen aus Di- aminen und polyamid-, polyurethan-, polyharnstoff- od. dgl. .bildenden bifuniktionellen Verbindungen, wobei als Di;amine:das i, 2-Di-(ß-aminioäthyl)-cycl,o- hexan oder dessen. Substitutionsprodukte verwendet werden. In Weiterbildung dieses Verfahrens wurde nungefunden,daß man an Stelle d:ieserDdaminie auch andere o@ Diuminedes Cyol:ohexans verwenden li:ann, welche .aus Naphtha.l.in oder Naphth:a1,inabkömmlin- gen durch teilweise R:ingsp.altung @in Verbindung mit einer vorhergehenden oder nachfolgenden Ringh:yd-rierung, übmführung :der erhaltenen o-Di- carb:onsäunen:,des Cyclohexans in Dinjitrile und an- schließende Reduktion (der Dinitrile zu Diaminen er- halten werden. Derartige o-D,iamino-Verbin,dungen des. Cyclohexans sind z. B. 2-(ß-Amin oäthyl)-cyclo- hexylamin- i, 2- (y-Aminopropyl) -cyclohexylamin- i, 2-(a-Am@inobutyl)-cyclohexyl!amin-r, i-(ß-Amino- äthyl) -2-(yJam@i)nopropyl) -cyclohexan. Maangelangt auch unter Anwendung @dde-ser Gruppe von Aminlen zu farblosen bzw. hellfarbigen super- polymeren; Kondensationsprodukten, die sich aus der Schmelze auf elastische, hochresistente, geformte Gebilde und. Massen verarbeiten. lassen, wie z. B. auf Fäden, Fasern, Borsten, Bänder, Schläuche, Filme, Folien usw., zu Spritz- und Prefima@ssen" Verbunds.chiichten, Kitten. u.,dgl. Bifunktionelle Verbindungen-, die für d @ie Herstel- lung von Superpolyamid en, -urethanen, -harnstoffen u.,dgl. aus Diaminen der vorgenannten Art >in Be- tracht kommen, sind beispielsweise Diearbonsäuren und. ihre flu;nktionellen Derivate, wie Glutarsäu.re, Adipimsäu:re, Sehac.insäure, Diglykolsäure, A:diipin- säurediiamild, Sebacinsäurediiphen#ylester, Cyclo- hexandäessigsäure, Cyclohexanessigsäure- i -pro- pionsäure-2, ferner Diäsocyanate, wie z. B. Hexa- methylen-uodlHieptamethylendiiisocyanat,Dii,soelio- cyanate, Di:usethane, wie z. B. Hexamethylen@dii@ure- than der Formel H2 N C 0-0-(C H2) s O- C O N H2, Harnstoffverbindungen, wie z. 3. Harn- stoff selib,st, ferner Heptamethylen@diharnstoff ,der Formell: H2 N C O N H-(C H2) 7 N H C O N H2, @so- wie Dikohlensäureester, wie z.. B, der Dnbu:tyl.-dakoh- lensäwreester @des,Hexamethyleniglykolis" C4 H9 O O C -0-(C H2) d--O-C O O C4 H9, und der Diphenyl- dikohlen.säureester dies Penitamethylengliykolis, (C6 H. -0-C 0-0-(C H2) 5 0-C O O C6 H5. Die Kondeinslation der bifunktionellen: Venbindun, gen mit dien. erfindungsgemäßen o-Diaminen des Cyclohexans erfolgt in en. sich bekannter Weise, wobei man gegebenenfalls Lösungs- oder Verdün- nungsmittel und auch Kontaktstoffe mitverwenden kann;. Ferner 'kann man, die erfindungisgemäßen Amine anteilig auch durch andere bekannte Diamine ersetzen oder kann. auch beider Kondensation Gly- kole oder co-Aminocarbonsäuren mitverwenden. Beispiel, 29 Gewichtsteile gepuftverte Adfipinsäure und q.o Gewichtsteile i-(ß-Aminoäthyl)-2-(y-amino- propyl),cyclohexan, welches durch, Hydrierung des Dinitrils der Cyclohexanessigsäure-i-propion- säure-2 gewonnen wurdie, werden im geschlossenen Gefäß nach Verdrängen, der Luft mittels Stickstoff zunächst i Stunde auf i8o° und sodann 3 Stunden auf 22o° erhitzt, anschließend. wird bei gewöhn- lichem Druck unter Darüberlieite.n von Kohlensäure 3 Stunden auf 250 bis. 26o° erhitzt. Das erhaltene hellfarbige Polymer.isationsprodukt .ist .aus der Schmelsze verformbar. Process for making super polymeric compounds Da.s patent 92424o relates to a method for Production of super polymeric compounds from di- amines and polyamide, polyurethane, polyurea or the like. forming bifunctional compounds, where as di; amines: the i, 2-di- (ß-aminioethyl) -cycl, o- hexane or its. Substitution products used will. In continuing this process has been It has not been found that in place of d one also has this daminie other o @ Diuminedes Cyol: ohexans use li: ann, which .from Naphtha.l.in or Naphth: a1, inabkömmlin- gen by partial R: ingsp.altung @in connection with a preceding or following Ringh: yd-ration, transfer: the obtained o-di- carb: onsäunen:, of cyclohexane in dinjitrile and other final reduction (of the dinitriles to diamines will hold. Such OD, iamino connections Des. Cyclohexane are z. B. 2- (ß-amine ethyl) -cyclo- hexylamine- i, 2- (y-aminopropyl) -cyclohexylamine- i, 2- (a-Am @ inobutyl) -cyclohexyl! amine-r, i- (ß-amino- ethyl) -2- (yJam @ i) nopropyl) -cyclohexane. The need also applies to the @ dde-ser group from amines to colorless or light-colored super- polymers; Condensation products resulting from the melt on elastic, highly resistant, molded Structure and. Process masses. let, such as B. on threads, fibers, bristles, tapes, tubes, Films, foils, etc., on injection and Prefima @ ssen " Verbunds.chichten, kitten. and the like Bifunctional compounds - which are used for the manufacture development of super polyamides, urethanes and ureas and the like from diamines of the aforementioned type> in Tracht come, for example, are dearboxylic acids and. their flu; functional derivatives, such as glutaric acid, Adipic acid: re, sehacic acid, diglycolic acid, A: diipin- acid diiamild, sebacic acid di-phenyl ester, cyclo- hexane acetic acid, cyclohexane acetic acid- i -pro- pionic acid-2, also diesocyanates, such as. B. Hexa- methylene-uodlhieptamethylene diisocyanate, dii, soelio- cyanate, di: usethane, such as B. Hexamethylene @ dii @ ure- than the formula H2 NC 0-0- (C H2) s O- CON H2, urea compounds, such as. 3. Urinary stoff selib, st, furthermore heptamethylene @ diurea, der Formal: H2 NCON H- (C H2) 7 NHCON H2, @ so- such as dicarbonic acid esters, such as, for example, the Dnbu: tyl.-dakoh- lensäwreester @ des, Hexamethyleniglycol "C4 H9 OOC -0- (C H2) d - OC OO C4 H9, and the diphenyl- dicarbonic acid esters of penitamethylene glycole, (C6 H. -0-C 0-0- (C H2) 5 0-COO C6 H5. The condeinslation of the bifunctional: Venbindun, gen with dien. o-diamines of the invention Cyclohexane takes place in en. known way, where one, if appropriate, solution or diluent Use agents and contact materials as well can;. Furthermore 'one can, the according to the invention Amines also partly due to other known diamines replace or can. also with condensation Gly- use kole or co-aminocarboxylic acids. Example, 29 parts by weight of puffed adfipic acid and qo parts by weight of i- (ß-aminoethyl) -2- (y-amino- propyl), cyclohexane, which by, hydrogenation of the dinitrile of cyclohexaneacetic acid-i-propion- Acid-2 was obtained in the closed Vessel after displacing the air by means of nitrogen first 1 hour to 180 ° and then 3 hours heated to 22o °, then. is used with under pressure under excess of carbonic acid 3 hours on 250 bis. Heated to 26o °. The received light-colored polymerisation product .is .from the Deformable melt.

Claims (1)

PATENTANSPRUCH: Weiterbildung des Verfäh.rens gemäß Patent 92q.240 zur Herstellung superpolymerer Ver- bindungen aus Diaminen und polyamid-, poly- urethan-, polyharnstoff-u. dgl. bildenden bifunk- fiionellenl Verbindum:gen, dadurch gekennzeichnet, daß man an Stelle dies i, 2-Di-(@3 amin@ät'hyl.)- cyclohexans oder dessen Sabstitutionsprodukten andere, aus Naphthalin oder Naphthalin- abkömmIiingen durch teilweise Ringspaltung in Verbindiung mutvorhergehender oder nachfolgen.- der Hydritrung, Überführung der gebildeten o-Dicarbonsäuren dies. Cyclohexans in Dinitrile und Reduktion erhaltene o-Diam.ino-Verb@imidu.n:- geavdes Cyclohexans verwendet.
PATENT CLAIM: Further development of the ability according to the patent 92q.240 for the production of super polymeric bonds made of diamines and polyamide, poly urethane, polyurea u. like educational bifunk fiionellenl connections: genes, characterized by that instead of this i, 2-Di - (@ 3 amin @ ethyl.) - cyclohexane or its substitution products others, made of naphthalene or naphthalene derivatives through partial ring cleavage in Connection of previous or subsequent ones. the hydration, transfer of the formed o-dicarboxylic this. Cyclohexane to Dinitrile and reduction received o-Diam.ino-Verb@imidu.n: - used cyclohexane.
DED4183D 1943-03-27 1943-03-27 Process for making super polymeric compounds Expired DE925496C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DED4183D DE925496C (en) 1943-03-27 1943-03-27 Process for making super polymeric compounds

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Application Number Priority Date Filing Date Title
DED4183D DE925496C (en) 1943-03-27 1943-03-27 Process for making super polymeric compounds

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DE925496C true DE925496C (en) 1955-03-24

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223682A (en) * 1958-04-01 1965-12-14 Grace W R & Co Preparation of linear polyurea polymers from urea and an alicyclic diamine
US3352831A (en) * 1961-12-06 1967-11-14 Scholven Chemie Ag Polyamides from 3-amino-methyl-3, 5, 5-trialkyl-1-cyclohexylamine
WO2009139061A1 (en) 2008-05-15 2009-11-19 旭化成ケミカルズ株式会社 Process for producing isocyanate using diaryl carbonate
US8053595B2 (en) 2006-11-17 2011-11-08 Asahi Kasei Chemicals Corporation Process for producing isocyanates
US8362293B2 (en) 2007-01-11 2013-01-29 Asahi Kasei Chemicals Corporation Process for producing isocyanates
US9233918B2 (en) 2008-05-15 2016-01-12 Asahi Kasei Chemicals Corporation Isocyanate production process
WO2018212206A1 (en) 2017-05-15 2018-11-22 旭化成株式会社 Isocyanate production method

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223682A (en) * 1958-04-01 1965-12-14 Grace W R & Co Preparation of linear polyurea polymers from urea and an alicyclic diamine
US3352831A (en) * 1961-12-06 1967-11-14 Scholven Chemie Ag Polyamides from 3-amino-methyl-3, 5, 5-trialkyl-1-cyclohexylamine
US8053595B2 (en) 2006-11-17 2011-11-08 Asahi Kasei Chemicals Corporation Process for producing isocyanates
US8362293B2 (en) 2007-01-11 2013-01-29 Asahi Kasei Chemicals Corporation Process for producing isocyanates
WO2009139061A1 (en) 2008-05-15 2009-11-19 旭化成ケミカルズ株式会社 Process for producing isocyanate using diaryl carbonate
US8895774B2 (en) 2008-05-15 2014-11-25 Asahi Kasei Chemicals Corporation Process for producing isocyanates using diaryl carbonate
US9233918B2 (en) 2008-05-15 2016-01-12 Asahi Kasei Chemicals Corporation Isocyanate production process
WO2018212206A1 (en) 2017-05-15 2018-11-22 旭化成株式会社 Isocyanate production method
US11306055B2 (en) 2017-05-15 2022-04-19 Asahi Kasei Kabushiki Kaisha Isocyanate production method

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