DE2116882A1 - Neue Enamin-Verbindungen und deren Herstellung - Google Patents
Neue Enamin-Verbindungen und deren HerstellungInfo
- Publication number
- DE2116882A1 DE2116882A1 DE19712116882 DE2116882A DE2116882A1 DE 2116882 A1 DE2116882 A1 DE 2116882A1 DE 19712116882 DE19712116882 DE 19712116882 DE 2116882 A DE2116882 A DE 2116882A DE 2116882 A1 DE2116882 A1 DE 2116882A1
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- DE
- Germany
- Prior art keywords
- group
- optionally
- divalent
- enamine
- new
- 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.)
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- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/09—Diamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3293—Hydroxyamines containing heterocyclic groups
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3296—Hydroxyamines being in latent form
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Description
SCHERIFG AG Patentabteilung Axen/Bu |
If | F | A | R2 —F— |
-2- |
nen Formel | f ? C C |
||||
■ 5 | 0 Έ? | ||||
-T -C |
und wobei
Kohlenwasserstoff-Rest R , der eine, gegebenenfalls alkylgruppen-substituierte, Tri- oder Tetramethylen-Gruppe mit insgesamt bis zu 8 C-Atomen darstellt,
wdrin R die zuvor definierte Bedeutung hat,
Axen/Bu -9-
H= 7*9 Gew.-^ ·
(bereclinet für Di.-enn,m'.n )
Analyse: | C = 81,9 | Gew.- |
H = 11,9 | Gew.- | |
N = 6,2 | Gew. - | |
C = 81,8 | Gew.- | |
H = 12,0 | Gew.- | |
N = 6,1 | Gew.- | |
Beispiel | ■ 7 |
Pq : Polypropylenglykol
P10 : Polyester aus Adipinsaure/Trimetliyl-hexandiol
Beisp Hr. |
Polyisoc yanat aus |
Poly-enamine aus Isobutyr- aldehyd und |
Klebfrei nach (min) |
- ■ | Lagerzeit der Mischung., ohne Viskosi. tats- zunahme |
Wochen |
1,8 | C3 ■ | A | 20 . | Gießling mit H2O 12 Stunden |
>16 | Wochen |
1,9 | C4 | A7 | 90 | 100 | >12 | Wochen |
1,10 | °5 | .A7 | 50 . ' . | >12 | Wochen | |
1,11 | G4 - | 30 | 80 | >12 | Stunden | |
1 | °2- | A7 | 90 | 40 i | Wochen | |
1,12 | °4- | A7 | 120 | >16 | Wochen | |
4 | G4H | A8 | 40 | >7 | ||
(C4 + Pg) | 120 : | Wochen | ||||
3 | C4 | - A9 | >8 | Wochen | ||
3 | C5 | 60· | >8 | Wochen | ||
3. | C6 | Ag- | 90 ■ : | >8 | Wochen | |
3 | G4 H | 120 | >8 | Wochen | ||
3 | C3 * | A9 | 4Q .; | >8 | Wochen | |
3 | G3 | A9 | 120 | >5 | Wochen | |
2 | G4 | A10 | >8 | Wochen | ||
2 | A10 · | >8 | Wochen | |||
2 | G6 | A10 | >8 | Wochen | ||
2 | C4H | Aio | >8 | Wochen | ||
2 | A10 | >8 | Wochen | |||
2 | A10 | >5 | ||||
ι. ρ /τγΊ Γ JTn \ * / |
||||||
h Wasser | ||||||
hP9 | ||||||
HP9 ■ ■ | ||||||
hP8 | ||||||
η P8 (ν) | ||||||
l· P8 | ||||||
r P8 ^ | ||||||
Beisp. ITr. |
polyisocyanat aus |
Poly-enamine aus Isobutyraiaehyd und |
Lagerzeit der Mischung ohne Visk. Zunahme |
1 | C4 + P9 | A | >4 Wochen |
5 | C4 + P9 | A11 | >4 Wochen |
7 | C4 + P9 | A12 | >7 V/ochen |
7 | C4 | >7 Wochen | |
7 | C4 + P8 | A12 | >7 Wochen |
7 | A12 | >7 Wochen | |
7 | °6 | A12 | >7 Wochen |
4 | C5 + P8 (ν) | A8 | >12 Wochen |
+ (C4 + P9) | |||
4 | C6 | A8 | >12 Wochen |
13,4 | °4 + P8 | ' *A8 9 | >5 Wochen |
+(C4 + P9) |
Polyisocyanat aus |
Polyimin aus Isobutyralde- hyd und |
Klebfrei nach (min.) |
max.Lagerzeit (geliert nach) |
C2 +. P2 | ' A4 | 20 | 13 Tage |
C2 + V/asser | A4 · | 30 | 7 Tage |
C2 + P3 | A4 | 15 | 16 Stunden |
C3 + P4 | A4 | 15 | 18 Stunden |
C3 + P5 | 30 | 4 Stunden | |
°2 + r6 | A4 | 35 | 32 Tage |
A4 | 30 | 2 Tage | |
Cp + Wasser | A5 | 60 | 2 Tage |
c3 + P5 | A6 | 30 | 11 Stunden |
C2+P6 | A6 | 35 | 12 Wochen |
(Erwärmung)
Claims (9)
- Patentansprüchewobei A ein zweiwertiger organischer Rest ist, nämlichäa) ein zweiwertiger linearer oder verzweigter Kohlenwasserstoff-Rest mit 4 "bis 36 C-Atomen oderab) eine zweiwertige Polyäther-Kette der allgemeinen-Formel II,4B-0 4^ -B- (II),wobei B -CH2 - CH2 - , -CH - CH2 - ,-(CHg)4-,CH5ein zweiwertiger cycloaliphatischer oder aromatischer Kohlenwasserstoff-Rest, der gebenenfalls einen oder mehrere Alkyl-Substituenten tragen kann, mit insgesamt bis zu 12 C-Atomen und η eine ganze Zahl von 1 bis ca. 1000 sein kann, oderac) ein zweiwertiger, gegebenenfalls alkylgruppen-substituierter, Cyclopentyl- oder Cyciohexyl-Rest mit insgesamt bis zu 12 C-Atomen oderad) ein zweiwertiger, gegebenenfalls alkylgruppen-substituierter aromatischer Rest mit insgesamt bis zu12 C-Atomen-23-209850/127.7SCHERING AGPatentabteilungAxen/Busein kann, und wobei am Eest A ein-oder mehrere H-Atome durch Hydroxid-Gruppen substituiert sein können und wobei R1 und R2ba) einwertige lineare bzw. unsubstituierte oder verzweigte bzw. substituierte aliphatisch^, cycloaliphatische oder aromatische Reste mit 1 bis C-Atomen oderT)b) (zweiwertige) Äthylengruppen, die zu A je einen heterocyclischen Ring schließen, darstellen oderbc) zUfc-^mmen eine zweiwertige Äthylen-Gruppe bilden, die·gegebenenfalls durch eine Hydroxid-Gruppe und die. gegebenenfalls durch eine oder mehrere Alkyl-Gruppen substituiert) sein kann, und wobei A eine, gegebenenfalls alkylgruppen-substituierte, Äthylen-Gruppe ist,bd) Cyan-äthylrGruppen sind,
und wobeica) R Wasserstoff und R und R einzeln oder gleichzeitig ein Wasserstoff-Atom, eine Methyl- oder eine Äthyl-Gruppe sein könnenodercb) R Wasserstoff und R und R zusammen ein zweiwer-7
tiger Kohlenwasserstoff-Rest R , der eine, gegebenen-. falls alkylgruppen-substituierte, Tri~ oder Tetramethylen-Gruppe mit insgesamt bis zu 8 C-Atomen darstellt, sein können.-24-209850/1277SCHjäRIHG AGPatentabteilungAxen/Bu - 2. Neues Di-enamin der Formel III,H3G\ s~\ r~^ /ÖEiC=CH-IJ VCH2-CH2-CH2-/ N-CH=C (IH).H-7C CH·?
- 3. Neues Di-enamin der Formel. IY,~C i-Bu OH, CH, i-Bu GHx3\i ι 3 ι 3 1 / 5C=CH-N— CH0-C-CH9-CH-CH0-CH9-N CH=Ci.r\ — \J \J XX r^ \J xXmm\J XX Q "m\JXXf^H,Cf CH, "CHj j . l3
- 4. Neues Di-enamin der Formel V,H5C i-Bu CH3 CH5 i-Bu JOH5C=CH-N CH2-CH-CH2-C CH2-CH2-N CH=CT (Y).H3C CH3 X
- 5. Neues Di-enamin der Formel VI,
i-Bu
H3CCH,
N
CH2CH OH,
C
CH3pOH3 OH3 i-Bu CH3 (VI).209 8-5 0/1277SCHi]RIJTG AGPatentabteilungAxen/Bu - 6. Neue Verbindung der Formel VIII,(VIII).
- 7. Neue Verbindung der Formel IX, wH5C
-
8. Neues Enamm der Formel VII, "\ CH3 _> -CH=C ^ CH3. (VII). - 9. Verfahren zur Herstellung der Di-enamine gemäß Anspruchl-7, dadurch gekennzeichnet, daß sekundärelDiamine der allgemeinen Formel X,R1 R2
H-N-A-N-H (X),12worin die Gruppen A, R und R die in Anspruch 1 definierte Bedeutung haben, mita) aliphatischen Aldehyden der allgemeinen Formel XI2098 5 0/1277AGP at ent ab t ο ilung
Axen/Bueingegangen amSIIf _ GH - C = O-4- 5worin R und R einzeln oder gleichzeitig ein Wasserstoff-Atom, eine Methyl- oder eine Äthylgruppe sein können, oder mit -■b) cycloaliphatischen Ketonen der allgemeinen Formel XII, 7H - C C = 0■7 .■worin R' die in Anspruch 1 definierte Bedeutung hat,gegebenenfalls durch Säuren katalysiert, gegebenenfalls unter Wärmezufuhr oder Kühlung, mit oder ohne Lösungsmittel umgesetzt werden, wobei das entstehende Reaktionswasser und die überschüssigen Carbonyl-Verbindungen entfernt werden.0^ aVi+hvhauflüJN^min-.Gruppen enthaltende Präpolymere, dadu^tfh gekenn-man IvIono-enamine, die freie HjKjroxyl-- oder Amino-Gruppen'fee^halten, insbespnderedefs Moiio-enamin gemäß Anspruch 8,' mSst^solchen Mengefl an Polyisocyanaten umsetzt, die dem aktive^Nsiasajeiistoff äquivalent sind./licHeue linamin-Gruppen^eirfchaltende PrS^iplymere, hergestellt durcji Anspruch,^**? gemäße Umsetzung νοηχΐβηο-enaminen,m Mono-enamin gemäß Ansprucli&wdie freiei!iir3rrtTT^<TaST3r^Tj7^^-27-209850/1277SCHEEIIfG- AG
Patentabteilung
Α-θώ/Bu .<fOi Neue» mindestens eine Enamin-G-ruppe und mindestens eine Ketimin- und/oder Aldimin-Gruppe"enthaltende Verbindungen. .Φ$· Neue,.. eine· Enamin-· und eine Aldimin-G-ruppe enthaltende Verbindung der Eorael XIII-^C=CH-IT If-CH2-CH2-H=GH-CH . (XIII).H, er V~y ^GH7Verfahren sur Herstellung von mindestens eine Enamin-G-ruppe und mindestens eine Ketimin- unä/oder Aldimin.-G-ruppe enthaltenden Verbindungen genäß Anspruch IJ. und insbesondere Anspruch 12« dadurch gelcomasGichnet,. daß Verbindungenj die mindestens eine sekundäre Amino-Gruppe und mindestens eine primäre Amino-G-ruppe enthalten, mita) alipliatisclien Aldehyden der allgernainen ."Formel XI,. entsprechend Anspruch 9· a)> oderb) cycloalipha.tis.chen Ketonen der allgemeinen lOrrncl XU» entsprechend Anspruch 9. 1>),gegebenenfalls durch Säuren ktitalysicrt, gegebenenfalls uxiter" Tfiärmeaüfuhr oder EüJrilung, mit oder ohne Lc'i;=oixgy™ mittel umgesetzt werden, wobei dafür Sor^e getragen wird,, daß das entstehende I?calrtionsvf3.3oer uud die üb erschüfe igen Garbonyl-Verbindungen entfernt 'werden.\/ ge gemäß eingegangen am ^S2098 50/1277BAD ORIGff^L
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2125247A DE2125247C3 (de) | 1971-04-06 | 1971-04-06 | Verfahren zum Applizieren von Lacken, Vergußmassen, Spachtelmassen, Überzugs- und Beschichtungsmassen |
DE2116882A DE2116882C3 (de) | 1971-04-06 | 1971-04-06 | Enaminverbindungen und deren Herstellung |
DE19712167133 DE2167133C3 (de) | 1971-04-06 | 1971-04-06 | Di-Enamin-Verbindungen |
SU1745901A SU561517A3 (ru) | 1971-04-06 | 1972-02-09 | Композици дл получени лаков, формованных изделий, заливочных компаундов, шпаклевочных масс, прокладочных масс и покрытий |
IT2237972A IT953561B (it) | 1971-04-06 | 1972-03-25 | Composti enamminici loro preparazione ed impiego |
US240762A US3865791A (en) | 1971-04-06 | 1972-04-03 | Certain enamine compounds and methods for making and using the same |
FR7211899A FR2136178A5 (de) | 1971-04-06 | 1972-04-05 | |
AT291372A AT329016B (de) | 1971-04-06 | 1972-04-05 | Verfahren zur herstellung neuer di-enamine |
SE7204389A SE405256B (sv) | 1971-04-06 | 1972-04-05 | Sett att framstella tetningsmassor genom omsettning av blandningar av isocyanatkomponenter, bi- eller polyfunktionella enaminer och vatten |
AT200274*1A AT324513B (de) | 1971-04-06 | 1972-04-05 | Lagerstabile mischung |
JP3480672A JPS5716126B1 (de) | 1971-04-06 | 1972-04-06 | |
NLAANVRAGE7204634,A NL171816C (nl) | 1971-04-06 | 1972-04-06 | Werkwijze massa's, plamuurmassa's, dek- en bekledingsmassa's alsmede gevormde voortbrengselen. |
GB1589972A GB1394732A (en) | 1971-04-06 | 1972-04-06 | Enamine compounds their manufacture and use |
BE781756A BE781756A (fr) | 1971-04-06 | 1972-04-06 | Enamines, leur preparation et leur utilisation |
AT724174A AT338276B (de) | 1971-04-06 | 1974-09-09 | Verfahren zur herstellung von neuen, mindestens eine enamin- und mindestens eine ketimin- und/oder aldimingruppe enthaltenden verbindungen |
US05/520,356 US3941753A (en) | 1971-04-06 | 1974-11-01 | Prepolymers of polyisocyanates with hydroxy-enamines or hydroxy-ketimines |
AT296978A AT377275B (de) | 1971-04-06 | 1978-04-25 | Lagerstabile mischung |
NLAANVRAGE8203663,A NL177219C (nl) | 1971-04-06 | 1982-09-21 | Werkwijze voor het bereiden van prepolymeren en van stabiele mengsels; gevormde voortbrengselen. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2116882A DE2116882C3 (de) | 1971-04-06 | 1971-04-06 | Enaminverbindungen und deren Herstellung |
DE2125247A DE2125247C3 (de) | 1971-04-06 | 1971-04-06 | Verfahren zum Applizieren von Lacken, Vergußmassen, Spachtelmassen, Überzugs- und Beschichtungsmassen |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2116882A1 true DE2116882A1 (de) | 1972-12-07 |
DE2116882B2 DE2116882B2 (de) | 1976-11-25 |
DE2116882C3 DE2116882C3 (de) | 1985-05-15 |
Family
ID=25760937
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2125247A Expired DE2125247C3 (de) | 1971-04-06 | 1971-04-06 | Verfahren zum Applizieren von Lacken, Vergußmassen, Spachtelmassen, Überzugs- und Beschichtungsmassen |
DE2116882A Expired DE2116882C3 (de) | 1971-04-06 | 1971-04-06 | Enaminverbindungen und deren Herstellung |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2125247A Expired DE2125247C3 (de) | 1971-04-06 | 1971-04-06 | Verfahren zum Applizieren von Lacken, Vergußmassen, Spachtelmassen, Überzugs- und Beschichtungsmassen |
Country Status (8)
Country | Link |
---|---|
US (1) | US3865791A (de) |
AT (2) | AT324513B (de) |
BE (1) | BE781756A (de) |
DE (2) | DE2125247C3 (de) |
FR (1) | FR2136178A5 (de) |
GB (1) | GB1394732A (de) |
NL (1) | NL171816C (de) |
SE (1) | SE405256B (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2356213A1 (de) * | 1973-11-10 | 1975-05-15 | Schering Ag | Neue ketimingruppen enthaltende prepolymere |
EP0284912A2 (de) * | 1987-03-28 | 1988-10-05 | BASF Aktiengesellschaft | Polyamid- und Polyharnstoffgruppen gebunden enthaltende Elastomere sowie Verfahren zur Herstellung von elastischen, kompakten oder zelligen Formkörpern hieraus |
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DE2718393C2 (de) * | 1977-04-26 | 1985-05-09 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur Herstellung von für Prepolymere geeigneten hydroxylgruppenhaltigen Monoenaminen |
DE2651479C2 (de) * | 1976-11-11 | 1986-03-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Elastisches Klebemittel |
US4087413A (en) * | 1977-03-07 | 1978-05-02 | The Dow Chemical Company | Crosslinked, linear, acylated polyalkylenepolyamines and process therefor |
DE3112118A1 (de) * | 1981-03-27 | 1982-10-07 | Bayer Ag, 5090 Leverkusen | Polymerisathaltige polyetherpolyamine, verfahren zur herstellung dieser polyamine und deren verwendung als aufbaukomponente zur herstellung von polyurethanen |
US4525590A (en) * | 1981-07-29 | 1985-06-25 | Bayer Aktiengesellschaft | Simplified process for the production of polyamines by the alkaline hydrolysis of compounds containing NCO-groups |
CA1221383A (en) * | 1981-08-07 | 1987-05-05 | Werner Rasshofer | Polyamines, a process for the production of polyamines and their use in the production of polyurethanes |
US4469857A (en) * | 1981-11-06 | 1984-09-04 | Minnesota Mining And Manufacturing Company | Two component system for the production of a synthetic resin compound capable of curing in the absence of moisture containing a polyisocyanate, a polyenamine, and a carrier compound having water aggregated thereto |
DE3144874A1 (de) * | 1981-11-12 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyaminen aus n-monoaryl-n', n'-dialkylharnstoff-verbindungen und ihre verwendung zum aufbau von polyurethanen |
US4723032A (en) * | 1981-11-12 | 1988-02-02 | Bayer Aktiengesellschaft | Modified polyamines and a process for their production |
DE3223400A1 (de) * | 1982-06-23 | 1983-12-29 | Bayer Ag, 5090 Leverkusen | Polyamine, verfahren zur herstellung von polyaminen und deren verwendung zur herstellung von polyurethanen |
DE3223398A1 (de) * | 1982-06-23 | 1983-12-29 | Bayer Ag, 5090 Leverkusen | Polyamine, verfahren zur herstellung von polyaminen und deren verwendung zur herstellung von polyurethanen |
DE3223397A1 (de) * | 1982-06-23 | 1983-12-29 | Bayer Ag, 5090 Leverkusen | Einstufenverfahren zur herstellung von polyaminen aus nco-prepolymeren, polyamine und deren verwendung zur herstellung von polyurethanen |
DE3227219A1 (de) * | 1982-07-21 | 1984-02-02 | Bayer Ag, 5090 Leverkusen | Einstufenverfahren zur herstellung von polyaminen aus nco-praepolymeren, polyamine und deren verwendung zur herstellung von polyurethanen |
DE3244913A1 (de) * | 1982-12-04 | 1984-06-07 | Bayer Ag, 5090 Leverkusen | Aminogruppen enthaltende reaktionskomponenten, verfahren zu ihrer herstellung und ihre verwendung |
DE3446921A1 (de) * | 1984-12-21 | 1986-07-03 | Bayer Ag, 5090 Leverkusen | Neue alkoxylierte aminopolyether, verfahren zu ihrer herstellung und sie enthaltende kohle-wasser-aufschlaemmungen |
DE3530476A1 (de) * | 1985-08-27 | 1987-03-05 | Bayer Ag | Polyamine, verfahren zu ihrer herstellung aus nco-prepolymeren und ihre verwendung bei der herstellung von polyurethanen |
DE3534947A1 (de) * | 1985-10-01 | 1987-04-09 | Bayer Ag | Verfahren zur herstellung von polyaminen, polyamine und deren verwendung zur herstellung von polyurethanen |
AT385047B (de) * | 1986-05-27 | 1988-02-10 | Vianova Kunstharz Ag | Verfahren zur herstellung von kationischen wasserverduennbaren bindemitteln und deren verwendung |
US5053478A (en) * | 1987-03-04 | 1991-10-01 | Moore James A | Production and processing of thermally stable polyenaminonitriles |
US4966954A (en) * | 1987-03-04 | 1990-10-30 | Rensselaer Polytechnic Institute | Production and processing of thermally stable polyenaminonitriles and polyaminoquinolines therefrom |
GB8821181D0 (en) * | 1988-09-09 | 1988-10-12 | Ici America Inc | Improved reaction injection moulding compositions |
US4935460A (en) * | 1987-03-11 | 1990-06-19 | Ici Americas Inc. | Reaction injection molding compositions |
US5093383A (en) * | 1987-03-11 | 1992-03-03 | Ici Americas Inc. | Polyurethane/urea foams from isocyanate prepolymers and isocyanate reactive imino/enamino functional reactants |
US5072026A (en) * | 1987-03-11 | 1991-12-10 | Ici Americas Inc. | Polyureas by reaction injection moulding of enamino-functional aliphatic polyether resin-containing systems and an enamine-terminated polyether |
DE3713858A1 (de) * | 1987-04-25 | 1988-11-17 | Bayer Ag | Aromatische polyamine, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethankunststoffen |
GB8821186D0 (en) * | 1988-09-09 | 1988-10-12 | Ici America Inc | Compositions of matter |
GB8821183D0 (en) * | 1988-09-09 | 1988-10-12 | Ici America Inc | Composition of matter |
GB8924127D0 (en) * | 1989-10-26 | 1989-12-13 | Ici Plc | Compositions of matter |
US5108575A (en) * | 1990-02-23 | 1992-04-28 | E. I. Du Pont De Nemours And Company | Polyamine enamine containing cationic resin |
US4980398A (en) * | 1990-02-23 | 1990-12-25 | E. I. Du Pont De Nemours And Company | Polyamine enamine containing cationic resin |
GB9117068D0 (en) * | 1991-08-08 | 1991-09-25 | Ici Plc | Cold curable polyisocyanate adhesive and sealant systems |
US5584958A (en) * | 1992-08-04 | 1996-12-17 | Imperial Chemical Industries Plc | Polyisocyanate adhesive and sealant systems |
US6103849A (en) * | 1994-06-27 | 2000-08-15 | Bayer Corporation | Storage stable, heat curable polyurethane compositions |
US7078475B2 (en) * | 2001-06-15 | 2006-07-18 | Huntsman Petrochemical Corporation | Synergistic amine chain-extenders in polyurea spray elastomers |
EP1854817A1 (de) * | 2006-05-09 | 2007-11-14 | Sika Technology AG | Zweikomponentige Polyurethanzusammensetzung mit hoher Frühfestigkeit |
JP2010530436A (ja) * | 2007-06-19 | 2010-09-09 | ハンツマン ペトロケミカル エルエルシー | ポリウレタンフォーム用の反応性アミン触媒 |
US20110040016A1 (en) * | 2008-04-21 | 2011-02-17 | Yakulis Jr George | Curable compositions that form a high modulus polyurea |
US20100152407A1 (en) * | 2008-12-17 | 2010-06-17 | Loctite (R&D) Limited | Novel compounds |
US20100311890A1 (en) * | 2009-06-05 | 2010-12-09 | Ppg Industries Ohio, Inc. | Curable compositions that form a low modulus polyurea |
US20110076485A1 (en) * | 2009-09-29 | 2011-03-31 | Ppg Industries Ohio, Inc. | Substrates coated with clear polyurea film-forming compositions |
US20120142943A1 (en) | 2010-12-03 | 2012-06-07 | Dow Agrosciences Llc | Processes for the preparation of enamines |
UA112066C2 (uk) * | 2010-12-03 | 2016-07-25 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Способи отримання енамінів |
UA109469C2 (xx) * | 2010-12-03 | 2015-08-25 | Способи отримання енамінів | |
KR102272782B1 (ko) | 2013-04-19 | 2021-07-08 | 코베스트로 엘엘씨 | 몰드 내 전자 인쇄 회로 기판 캡슐화 및 조립체 |
EP3372624A1 (de) | 2017-03-06 | 2018-09-12 | Henkel AG & Co. KGaA | Einkomponentige zusammensetzung auf basis von verbindungen mit mindestens zwei einheiten aus cyclischem exo-vinylen-carbonat |
ES2952010T3 (es) * | 2019-02-18 | 2023-10-26 | Basf Se | Proceso para la eliminación de gases ácidos de una corriente de fluido con un absorbente líquido que comprende un anillo de piperazina |
CN111072903B (zh) * | 2019-12-30 | 2021-04-09 | 中国科学院山西煤炭化学研究所 | 一种阳离子型水性聚氨酯乳液的制备方法 |
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US3074940A (en) * | 1958-09-10 | 1963-01-22 | Monsanto Chemicals | Process for the manufacture of enamines |
DE1226585B (de) * | 1964-09-04 | 1966-10-13 | Bayer Ag | Verfahren zur Herstellung von 1, 3-Dioxanen |
GB1200718A (en) * | 1968-01-02 | 1970-07-29 | Bayer Ag | Process for the production of crosslinked synthetic resins and sheets produced therefrom |
DE2402037B1 (de) * | 1974-01-17 | 1975-05-28 | Teroson Gmbh, 6900 Heidelberg | Polyvinylchloridplastisole |
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CH372041A (de) * | 1958-09-10 | 1963-09-30 | Monsanto Chemicals | Verfahren zur Herstellung von Isobutenylaminen |
DE1158496B (de) * | 1961-01-20 | 1963-12-05 | Bayer Ag | Verfahren zur Herstellung von N, N', N'-trisubstituierten p-Phenylendiaminen |
US3314922A (en) * | 1961-08-21 | 1967-04-18 | Du Pont | Polymers and process of making same |
GB1064841A (en) * | 1963-02-04 | 1967-04-12 | Ici Ltd | Manufacture of polymers containing biuret and urea groups |
US3267078A (en) | 1963-12-16 | 1966-08-16 | Wyandotte Chemicals Corp | Polyether urethane coating composition cured with a di-imine |
DE1595748A1 (de) * | 1965-06-01 | 1970-05-14 | Gen Mills Inc | Durch Feuchtigkeitseinwirkung haertende Polyisocyanat- und Polyaminmasse |
FR1493879A (fr) * | 1965-09-17 | 1967-09-01 | Gen Mills Inc | Dérivés de certains polyamines et isocyanates organiques et leur utilisation dans des préparations de polymères |
US3535353A (en) * | 1966-10-24 | 1970-10-20 | Gen Mills Inc | Derivatives of certain polyamine compounds and carboxylic acids |
US3493543A (en) * | 1967-03-20 | 1970-02-03 | Gen Mills Inc | Polyurea compositions and the coating of substrates with such compositions |
DE1719121C3 (de) * | 1967-11-04 | 1980-07-10 | Bayer Ag, 5090 Leverkusen | Verfahren zum Abdichten und Ausfüllen von Fugen |
-
1971
- 1971-04-06 DE DE2125247A patent/DE2125247C3/de not_active Expired
- 1971-04-06 DE DE2116882A patent/DE2116882C3/de not_active Expired
-
1972
- 1972-04-03 US US240762A patent/US3865791A/en not_active Expired - Lifetime
- 1972-04-05 AT AT200274*1A patent/AT324513B/de not_active IP Right Cessation
- 1972-04-05 FR FR7211899A patent/FR2136178A5/fr not_active Expired
- 1972-04-05 AT AT291372A patent/AT329016B/de not_active IP Right Cessation
- 1972-04-05 SE SE7204389A patent/SE405256B/xx unknown
- 1972-04-06 GB GB1589972A patent/GB1394732A/en not_active Expired
- 1972-04-06 NL NLAANVRAGE7204634,A patent/NL171816C/xx not_active IP Right Cessation
- 1972-04-06 BE BE781756A patent/BE781756A/xx not_active IP Right Cessation
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US3074940A (en) * | 1958-09-10 | 1963-01-22 | Monsanto Chemicals | Process for the manufacture of enamines |
DE1226585B (de) * | 1964-09-04 | 1966-10-13 | Bayer Ag | Verfahren zur Herstellung von 1, 3-Dioxanen |
GB1200718A (en) * | 1968-01-02 | 1970-07-29 | Bayer Ag | Process for the production of crosslinked synthetic resins and sheets produced therefrom |
DE2402037B1 (de) * | 1974-01-17 | 1975-05-28 | Teroson Gmbh, 6900 Heidelberg | Polyvinylchloridplastisole |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2356213A1 (de) * | 1973-11-10 | 1975-05-15 | Schering Ag | Neue ketimingruppen enthaltende prepolymere |
EP0284912A2 (de) * | 1987-03-28 | 1988-10-05 | BASF Aktiengesellschaft | Polyamid- und Polyharnstoffgruppen gebunden enthaltende Elastomere sowie Verfahren zur Herstellung von elastischen, kompakten oder zelligen Formkörpern hieraus |
EP0284912A3 (en) * | 1987-03-28 | 1989-10-25 | Basf Aktiengesellschaft | Elastomers containing polyamide and polyurea groups and procedure for the preparation of elastic, compact or cellular mouldings thereof |
Also Published As
Publication number | Publication date |
---|---|
ATA291372A (de) | 1975-07-15 |
SE405256B (sv) | 1978-11-27 |
GB1394732A (en) | 1975-05-21 |
NL171816B (nl) | 1982-12-16 |
DE2116882C3 (de) | 1985-05-15 |
AT324513B (de) | 1975-09-10 |
BE781756A (fr) | 1972-10-06 |
DE2116882B2 (de) | 1976-11-25 |
NL7204634A (de) | 1972-10-10 |
DE2125247C3 (de) | 1981-07-23 |
NL171816C (nl) | 1983-05-16 |
US3865791A (en) | 1975-02-11 |
DE2125247A1 (de) | 1972-10-19 |
AT329016B (de) | 1976-04-26 |
DE2125247B2 (de) | 1977-08-11 |
FR2136178A5 (de) | 1972-12-22 |
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