DE1745459C3 - Process for the production of amide groups, urethane groups and optionally foams containing urea groups - Google Patents
Process for the production of amide groups, urethane groups and optionally foams containing urea groupsInfo
- Publication number
- DE1745459C3 DE1745459C3 DE1967SC041075 DESC041075A DE1745459C3 DE 1745459 C3 DE1745459 C3 DE 1745459C3 DE 1967SC041075 DE1967SC041075 DE 1967SC041075 DE SC041075 A DESC041075 A DE SC041075A DE 1745459 C3 DE1745459 C3 DE 1745459C3
- Authority
- DE
- Germany
- Prior art keywords
- products
- fatty acid
- fatty acids
- groups
- condensation
- 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
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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/3825—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
thermisch oder mit Katalysatoren, z. B. katalytisch wirkenden Tonen oder Radikalbildnern, durchgeführt werden. Der Begriff polymere Fettsäuren umfaßt ■sowohl die homopolymeren Fettsäuren als auch die copolymeren Fettsäuren, bei denen zwei oder gegebenenfalls mehrere Fettsäuremoleküle direkt oder über Co-Componenten verknüpft sind.thermally or with catalysts, e.g. B. catalytically active clays or radical formers carried out will. The term polymeric fatty acids encompasses both the homopolymeric fatty acids and the copolymeric fatty acids in which two or, if appropriate, several fatty acid molecules directly or via Co-components are linked.
Für die Herstellung der erfindungsgemäß verwendeten Fettsäuredialkanolamide werden Fettsäuregemische verwendet, die neben dimeren Fettsäuren, weiche bei der Polymerisation in überwiegendem Anteil gebildet werden, auch trimere und polymere Fettsäuren neben einem Anteil an monomeren Fettsäuren enthalten. Es ist ebenfalls möglich, die polymeren Fettsäuren durch Hydrierung mehr oder weniger weitgehend abzusättigen.For the production of the fatty acid dialkanolamides used according to the invention, fatty acid mixtures are used used, in addition to dimeric fatty acids, soft in the polymerization in a predominant proportion also contain trimeric and polymeric fatty acids in addition to a proportion of monomeric fatty acids. It is also possible to more or less largely hydrogenate the polymeric fatty acids to satiate.
Anstelle der Fettsäuregemische aus den monomeren und polymeren Fettsäuren können auch deren Ester mit einwertigen, 1 bis 4 Kohlenstoffatome enthaltenden Alkoholen verwendet werden.Instead of the fatty acid mixtures from the monomeric and polymeric fatty acids, their esters can also be used monohydric alcohols containing 1 to 4 carbon atoms can be used.
ErfindungsgemäÖ werden für die Herstellung der Fettsäuredialkanolamide Fettsäuregemische, weiche bei der Polymerisation ein- und mehrfach ungesättigter natürlicher Fettsäuren anfallen, folgender Zusammensetzung verwendet:According to the invention are used for the production of Fatty acid dialkanolamides Fatty acid mixtures, soft in the polymerization of monounsaturated and polyunsaturated natural fatty acids, the following composition is used:
monomere Fettsäuren bis 50%monomeric fatty acids up to 50%
dimere Fettsäuren 10 bis 90%
und trimere und polymeredimeric fatty acids 10 to 90%
and trimers and polymers
Fettsäuren bis 60%.Fatty acids up to 60%.
Als Dialkanolamide kommen solche mit einem Alkylenrest von 2 bis 4 kohlenstoffatomen in Betracht, z. B. vorzugsweise Diethanolamin, oder Pz-n-propanolamin. Setzt man dagegen Diisopropinolamin ein, so ist zur Steigerung der Reaktionsfähigkeit d α erfindungsgemäß verwendeten Fettsäuredialkanolamids Beschleunigerzusatz erforderlich.Suitable dialkanolamides are those with an alkylene radical of 2 to 4 carbon atoms, e.g. B. preferably diethanolamine, or Pz-n-propanolamine. If, on the other hand, diisopropynolamine is used, then the fatty acid dialkanolamide used according to the invention must be added to increase the reactivity d α.
Die zur Hersteilung der Polyurethanschaumstoffe geeigneten Polyisocyanate können zwei oder mehr Isocyanatgrupperi tragen und gehören vorzugsweise der aromatischen sowie araliphatischen Reihe an. Beispiele hierfür sind:The polyisocyanates suitable for making the polyurethane foams can be two or more Isocyanate groups carry and preferably belong to the aromatic and araliphatic series. Examples for this are:
ρ,ρ'-Diphenylmethandiisocyanat,
Polymethylenpolyphenylisocyanat,
3r3'-Dimethyl-diphenylmethan-4,4'-diisocyanat,
2,4-ToluyIendiisocyanat,2,6-Toluolylendiisocyanat, m-Phenylendiisocyanat.p-Phenylendiisocyanat,
1,5- NaphthylendiisocyanaLρ, ρ'-diphenylmethane diisocyanate,
Polymethylene polyphenyl isocyanate,
3 r 3'-dimethyl-diphenylmethane-4,4'-diisocyanate,
2,4-toluene diisocyanate, 2,6-toluene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate,
1,5-naphthylene diisocyanate L
Es können auch Gemische verschiedener Polyisocyanate verwendet werden.Mixtures of different polyisocyanates can also be used.
Die Herstellung der Polyurethanschaumstoffe erfolgt in der üblichen Weise durch Umsetzung der Hydroxyl- und Isocyanatkomponenten in vorwiegend stöchiometrischen Mengen.The polyurethane foams are produced in the usual way by reacting the hydroxyl and isocyanate components in predominantly stoichiometric amounts.
Wegen ihrer guten Verträglichkeit mit den handelsüblichen Polyolen und Polyisocyanaten ist es möglich, die Eigenschaften der Polyurethanschaumstoffe durch entsprechende Abmischungen zu variieren. Als besonders vorteilhafte Mischungskomponenten kommen Polyole, wie z. B. N,N,N',N'-Tetrakis-(2-hydroxypropyl)-äthylendiamin, für Hartschäume brauchbare Polyäther, sowie die in der DE-OS 17 45443 beschriebenen bimerfettsäure-bls-monoalkanolamide in BetrachtBecause of their good compatibility with the commercially available polyols and polyisocyanates, it is possible to vary the properties of the polyurethane foams through appropriate blends. As special advantageous mixture components come polyols, such as. B. N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine, Polyethers usable for rigid foams, as well as those described in DE-OS 17 45443 bimer fatty acid-bls-monoalkanolamides into consideration
Als Zusatzmittel sind meistens die üblichen Emulgatoren und Schaumstabilisatoren erforderlich.The usual emulsifiers and foam stabilizers are usually required as additives.
Bei Bedarf können Weitere Zusatzstoffe, wie Füll· Und Farbstoffe, z. B. Kreide, Glasstapelfaser und Ruß, sowie Antioxidantien, Fungicide und feuerhemmende Mittel beigefügt werden. Ah Treibmittel benutzt man das durch Wasserzusatz gebildete Kohlendioxid, Fluorchloralkane oder Gemische von beiden.If necessary, other additives, such as fillers and dyes, e.g. B. chalk, glass staple fiber and carbon black, as well Antioxidants, fungicides and fire retardants are added. Ah propellant you use that Carbon dioxide formed by the addition of water, fluorochloroalkanes or mixtures of both.
Falls für den Verschäumungsprozeß eine höhere Aktivierung gewünscht wird, können die üblichen
Katalysatoren, wie tertiäre Amine, zugesetzt werden, wobei kleine Mengen meistens befriedigende Ergebnisse
liefern.
Die Herstellung der Schäume wird Vorzugs^ -eiseIf a higher activation is desired for the foaming process, the usual catalysts, such as tertiary amines, can be added, small amounts usually giving satisfactory results.
The production of the foams is preferred
ίο nach dem sogenannten one-shot-Verfahren derart durchgeführt, daß die Fettsäuredialkanolamide, mit den üblichen Treibmitteln und Zusatzstoffen vermischt, mit der Polyisocyanatkomponente in Formen zur Ausschäumung gebracht werden. Auch die Vorschäummethodeίο according to the so-called one-shot process like that carried out that the fatty acid dialkanolamides, mixed with the usual propellants and additives, with the polyisocyanate component in molds for foaming to be brought. Also the preview method
Ii (frothing) kann hier angewandt werden.Ii (frothing) can be used here.
Beispiele 1 — IlExamples 1 - Il
Die in der Tabelle angegebenen Fettsäuredialkanolamide werden mit den dort angegebenen Hilfs- und Zusatzstoffen intensiv miteinander vermischt; nach Zugabe des Polyisocyanats setzt die Reaktion ein, und das Gemisch wird rasch in eine offene FormThe fatty acid dialkanolamides given in the table are combined with the auxiliary and Additives intensively mixed with one another; after the addition of the polyisocyanate, the reaction begins, and the mixture quickly turns into an open form
ausgegossen.poured out.
Die verwendeten, bei der Polymerisation ein- und mehrfach ungesättigter Tallölfettsäuren erhaltenen technischen Tallöl-Fettsäuregemische haben nach gaschromatographischer Analyse folgende Zusammensetzung: The used, obtained in the polymerization of monounsaturated and polyunsaturated tall oil fatty acids technical tall oil fatty acid mixtures have according to gas chromatographic Analysis of the following composition:
Gemisch IMixture I.
monomere Fettsäure 7 Gew.-%,monomeric fatty acid 7% by weight,
dimere Fettsäure 79 Gew.-%,dimer fatty acid 79% by weight,
trimere bzw. höherpolymere
Fettsäure 14 Gew.-%.trimeric or higher polymers
Fatty acid 14% by weight.
Gemisch IIMixture II
monomere Fettsäure 46 Gew.-%,monomeric fatty acid 46% by weight,
dimere Fettsäure 45 Gew.-%,dimer fatty acid 45% by weight,
trimere bzw. höherpolymere
Fettsäure 9%.trimeric or higher polymers
Fatty acid 9%.
Gemisch IIIMixture III
monomere Fettsäure 34%,monomeric fatty acid 34%,
dimere Fettsäure 20%,dimer fatty acid 20%,
trimere 4- höherpolymere
Fettsäure 46%.trimeric 4-higher polymers
Fatty acid 46%.
In der Tabelle bedeutet:In the table means:
ai—am Fettsäuredialkanolamide aus Diäthanolamin und polymerisiertem Tallölfettsäuregemisch im Molverhältnis 2,4:1ai — am fatty acid dialkanolamides from diethanolamine and polymerized tall oil fatty acid mixture in a molar ratio of 2.4: 1
OH-Zahl
Aminzahl
SäurezahlOH number
Amine number
Acid number
b) Elis-(-hydroxyäthyl)-dimerfettsäureamidb) Elis - (- hydroxyethyl) dimer fatty acid amide
OH-Zahl: 154
C) N,N,N',N'-Tetrakis-(2-hydroxypropyl)-äthylendiamin OH number: 154
C) N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine
d) handelsüblicher Polyäther auf der Basis von
propoxyiiertem Trimethylolpropan mit der OH-Zahl
550
e) Trichlormonofluormethand) Commercial polyether based on propoxyiated trimethylolpropane with an OH number of 550
e) trichloromonofluoromethane
f) N.N'-Dimethylpiperazinf) N.N'-dimethylpiperazine
g) Katriümricinus61sülfonat(50% Wassergehalt)
i) rohes Diphenylmethan4,4'-dnsocyanat.g) Katriümricinus61sülfonat (50% water content)
i) crude diphenylmethane 4,4'-dnsocyanate.
Beispiel Erfindungsgemäß verwendetes Fe(I-säuredialkanolamid (Gew.-Teile)Example Fe (I-acid dialkanolamide used according to the invention (Parts by weight)
ai an a:u a i a n a : u
Hilfs- und Zusatzstoffe (Gew.-Teilo)Auxiliaries and additives (part by weight)
kg/m1 kg / m 1
100100
1010
100100
7373
2525th
6060
0,50.5
0,50.5
* Beispiel 2, durchgeführt mit ausgewachsenem Fctlsäuredialkanolamid ι metrischer Umsetzung keinen brauchbaren Polyurethanschaum.* Example 2, carried out with fully grown Fctlsäuredialkanolamid ι metric conversion no usable polyurethane foam.
CO2 und CCf2FCO 2 and CCf 2 F
CCl3FCCl 3 F
LO,LO,
ι (OH-ZaIiI: 232, Aminzahl: 29) ergab bei stöchio-ι (OH number: 232, amine number: 29) resulted in stoichio-
Claims (1)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1967SC041075 DE1745459C3 (en) | 1967-07-29 | 1967-07-29 | Process for the production of amide groups, urethane groups and optionally foams containing urea groups |
CH45268A CH501026A (en) | 1967-01-31 | 1968-01-12 | Foamed plastics from reaction of polyisocyanates and |
NL6801300A NL148912B (en) | 1967-01-31 | 1968-01-29 | PROCESS FOR PREPARING REACTION PRODUCTS OF POLYISOCYANATES AND CONDENSATION PRODUCTS CONTAINING FREE HYDROXYL GROUPS. |
FR1554140D FR1554140A (en) | 1967-01-31 | 1968-01-30 | |
AT639168A AT290141B (en) | 1967-01-31 | 1968-07-03 | Process for the production of foams containing amide groups, urethane groups and optionally urea groups |
SE999268A SE346116B (en) | 1967-07-29 | 1968-07-22 | |
FR160383A FR95267E (en) | 1967-01-31 | 1968-07-24 | Process for the production of foamed materials. |
NL6810716A NL6810716A (en) | 1967-01-31 | 1968-07-29 | |
BE718747D BE718747A (en) | 1967-07-29 | 1968-07-29 | |
CH1133568A CH523931A (en) | 1967-01-31 | 1968-07-29 | Process for the production of foams |
GB3604568A GB1241038A (en) | 1967-07-29 | 1968-07-29 | Polyurethanes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1967SC041075 DE1745459C3 (en) | 1967-07-29 | 1967-07-29 | Process for the production of amide groups, urethane groups and optionally foams containing urea groups |
Publications (3)
Publication Number | Publication Date |
---|---|
DE1745459A1 DE1745459A1 (en) | 1971-09-09 |
DE1745459B2 DE1745459B2 (en) | 1978-10-12 |
DE1745459C3 true DE1745459C3 (en) | 1979-06-07 |
Family
ID=7436028
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1967SC041075 Expired DE1745459C3 (en) | 1967-01-31 | 1967-07-29 | Process for the production of amide groups, urethane groups and optionally foams containing urea groups |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE718747A (en) |
DE (1) | DE1745459C3 (en) |
GB (1) | GB1241038A (en) |
SE (1) | SE346116B (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE30772E (en) | 1978-03-28 | 1981-10-13 | Ppg Industries, Inc. | Amide-modified urethane acrylate radiation curable compounds and coating compositions and methods of making same |
CA1140695A (en) * | 1979-06-11 | 1983-02-01 | Charles E. Koehler | Miscible fluorocarbon-polyol blends |
DK1761580T3 (en) * | 2004-06-10 | 2008-08-25 | Randall C Jenkines | Polyurethane carpet backing made using fatty acid amide polyols |
DE102011007468A1 (en) | 2011-04-15 | 2012-10-18 | Evonik Goldschmidt Gmbh | Composition containing specific carbamate-type compounds suitable for the preparation of polyurethane foams |
DE102011007479A1 (en) | 2011-04-15 | 2012-10-18 | Evonik Goldschmidt Gmbh | Composition containing specific amides and organomodified siloxanes, suitable for the production of polyurethane foams |
DE102013217395A1 (en) | 2013-09-02 | 2015-03-05 | Evonik Industries Ag | Use of mixtures of organofunctionally modified polysiloxanes with amides in the production of flexible polyurethane foams |
DE102013226575B4 (en) | 2013-12-19 | 2021-06-24 | Evonik Operations Gmbh | Composition suitable for the production of polyurethane foams, containing at least one unsaturated fluorocarbon or unsaturated fluorocarbon as blowing agent, polyurethane foams, processes for their production and their use |
EP2886591A1 (en) | 2013-12-19 | 2015-06-24 | Evonik Industries AG | Composition, suitable for the production of polyurethane foams, containing at least one nucleating agent |
-
1967
- 1967-07-29 DE DE1967SC041075 patent/DE1745459C3/en not_active Expired
-
1968
- 1968-07-22 SE SE999268A patent/SE346116B/xx unknown
- 1968-07-29 BE BE718747D patent/BE718747A/xx unknown
- 1968-07-29 GB GB3604568A patent/GB1241038A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BE718747A (en) | 1969-01-29 |
SE346116B (en) | 1972-06-26 |
DE1745459B2 (en) | 1978-10-12 |
DE1745459A1 (en) | 1971-09-09 |
GB1241038A (en) | 1971-07-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C3 | Grant after two publication steps (3rd publication) | ||
EHJ | Ceased/non-payment of the annual fee |