DE1595063A1 - Process for the production of three-dimensional polymers from isocyanuric acid and diisocyanuric acid ester - Google Patents
Process for the production of three-dimensional polymers from isocyanuric acid and diisocyanuric acid esterInfo
- Publication number
- DE1595063A1 DE1595063A1 DE19651595063 DE1595063A DE1595063A1 DE 1595063 A1 DE1595063 A1 DE 1595063A1 DE 19651595063 DE19651595063 DE 19651595063 DE 1595063 A DE1595063 A DE 1595063A DE 1595063 A1 DE1595063 A1 DE 1595063A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- production
- diisocyanuric
- dimensional polymers
- acid ester
- 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.)
- Pending
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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- 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
-
- 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
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3851—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
- C08G18/3853—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring containing cyanurate and/or isocyanurate 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/776—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur phosphorus
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)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
Vorfahren zur Herstellung dreiaiaensionaier Polymerisate aus Isocyanursäure und Diisoeyansäure estern,,Ancestors for the production of three-dimensional polymers from isocyanuric acid and diisoeyanoic acid esters,
«gi i^m«Gi i ^ m
Am. Stickstoff substituierte.Derivate der isccyanursäures deren Molekül zviQl odor drai R-MH-CO Gruppen enthält, welche am Stickstoff iles Cyanursäurei'i.n/Jies gebunden sind, vyobei das einwertige Radikal Il aus aliphatischen» alicyclischen oder cyclischen Heater üGöteht, xrnä welche βc-jelienenfalls einen oder mehrere Halogen», StiolLgtoff-j Schviefel-Substituanten etc» tragen können, sind bore-ita ."bcachrliDben .worden« Diese üerivate v;erden durch Reaktioa eines oder melirorer Isocyansäureester der allgemeinen E'oxvjiel lt-ji-00 wit risr IsoeyauaratiiLro in cinea wasserfreien und chemisch inei'tsn LiSauni^nittel horgesteilto At the. Nitrogen-substituted.Derivate of isccyanuric acid s whose molecule contains zviQl or drai R-MH-CO groups, which are bound to the nitrogen iles Cyanuric acidi.n / Jies, vyobei the monovalent radical II from aliphatic, alicyclic or cyclic heaters β c-jelienenfalls can carry one or more halogen, "StiolLgtoff-j-Schviefel Substituanten etc,""bcachrliDben are bore-ita .worden" This üerivate v;. Reaktioa ground by one or melirorer isocyanic ester of the general E'oxvjiel lt ji -00 wit risr IsoeyauaratiiLro in cinea anhydrous and chemically inei'tsn LiSauni ^ nittel horgesteilt o
909837/1509909837/1509
H. 107H. 107
Erfindungsgemäss wurde nunmehr gefunden, dasa man bela Ergati der Isooyanaäureester der Foreel R-BbGO duroh normale Düsocyansäureester R(NOO)2 oder duroh Diisooyaneäure-Heteroester, trlt R-PO(FCO)2 oder E- P(SCO^ oder ganz allgemein jegliche« anderen Diisocyansäure-IIeteroester, in welchem ciae Radikal R einen einwertigen oder zweiwertigen, aliphatischen, alieyelisohen oder cyclischen Rest darstellt, welcher gegebenenfalls Halogen-» Stiele» stoff-, Schwefel-Sufcstituenten eto. tragen kann, unter bestimmten Verfahrensοedingungen eine großse Reihe dreidimensionaler Polymerisate erhält. Wenn derartige Verbindungen beispielsweise ausgehend von normalen Düsocyansäureestern erhalten werden, könnenAccording to the invention, it has now been found that one bela Ergati the isooyanaic acid ester of Foreel R-BbGO by normal diisocyanic acid ester R (NOO) 2 or by diisooyanic acid heteroester, R-PO (FCO) 2 or E-P (SCO ^ or in general any « Another diisocyanic acid IIeteroester, in which the radical R represents a monovalent or divalent, aliphatic, aliphatic or cyclic radical, which can optionally carry halogen, stem, sulfur, etc., receives a large number of three-dimensional polymers under certain process conditions If such compounds are obtained, for example, starting from normal diisocyanic acid esters, sie duroh die nachstehende Formel dargestellt werdentthey are represented by the following formula
0 0 00 0 0
ν η ην η η
A Λ A Λ /\/ \
...J ΪΤ - CO-IJH-R-IJE-CO - Ιί JT- CO-NH-R-B&-GO - Ή JS ... J ΪΤ - CO-IJH-R-IJE-CO - Ιί JT- CO-NH-RB & -GO - Ή JS
υ 6*0 OeCυ 6 * 0 OeC
CsO 0»υ 6CsO 0 »υ 6
V VV V
CO-HH-R-BH-CO-ITn CO-HH-R-BH-CO-IT n
) at C OeO) at C OeO
0 « C ObO • tie0 «C ObO • tie
Im allgemeinen erhält man diese Polymeren, indem man in der Hitze die Cyanursäure und den Diieooyansäureaster in Gegenwart eines Polymerisationskatalysatoren gegebenenfalls in einem Lösungsmittel der Cyanursäure reagieren lässt«In general, these polymers are obtained by placing them in the heat the cyanuric acid and the Diieooyansäureaster in the presence of one Polymerization catalysts can react if necessary in a solvent of cyanuric acid «
- 2 - - "' — ■ ♦- 2 - - "'- ■ ♦
909837/1509 bad original909837/1509 bad original
Ε· 107Ε 107
Die erhaltenen Produkte sind bei Temperaturen über 300 °0 stabil und im gröseten Teil der bekennten Lösungsmittel» ein* Bchlieselich jener der Cyanursäures unlöslich« The products are stable at temperatures above 300 ° 0 and gröseten part of professed solvent "a * Bchlieselich that of cyanuric s insoluble"
Die Annendungsmöglichkeiton dieser Produkte erstrecken sich ilhsr einen weiten Bereich? insbesondere euf dem Gebiete der Tier- und fflanzcn^Schä^lingsbekempfungamittel, der pharmazeutischen lind Vetcr.1r&3>-Proauktef der plaatiechen l»<ase<;n, der Textil« produlcte uew« The application possibilities of these products extend over a wide range? especially euf the field of animal and fflanzcn ^ ^ Schä lingsbekempfungamittel, pharmaceutical lind Vetcr.1r &3> -Proaukte f the plaatiechen l »<ase <n, the textile" produlcte uew "
Die naohstethendei'' Beispiele; erlirvtern die Er3 induiis ohne sie sot beschränken aThe naohstethendei '' examples; learn the Er3 induiis without them so restrict a
B β i a ρ :>. β 1B β i a ρ:>. β 1
Man läset lei 120 0C 2 Hol Cyanviraüure und 3 Mol Toluyltm-2,4-diieocyanat in Gegenwart vo2i 40 smr Trillthylrjain ala Katalysator reaßjerenc. Die Cyanursäure lQst eioh z.vtf und beim Abküh?.en erstarrt dag Reakticnsproduki. Das erhaltene Derivat ist ein dreddimenßionaXes Polymerißpt der FormelOne läset lei 120 0 C 2 Hol Cyanviraüure and 3 mol Toluyltm-2,4-diieocyanat in the presence VO2I 40 smr Trillthylrjain ala catalyst reaßjerenc. The cyanuric acid lQst eioh z.vtf and .en solidifies dag Reakticnsproduki during cool down?. The derivative obtained is a three-dimensional polymer of the formula
0
η 0
η
/c °/ c °
ο.,.Κ* N5 - CO-IlH- < ~y £ ο.,. Κ * N 5 - CO-IlH- < ~ y £
0*0 ^HH-OO - I B· · · ·0 * 0 ^ HH-OO - I B · · · ·
0 H0 H
ET 0 β & JCJ ε: 0ET 0 β & JCJ ε: 0
909837/1509 bad909837/1509 bathroom
„ 3 ..,"3 ..,
E. 107E. 107
dessen Struktur durch Ultrarotspektrua bewiesen 1st Analyse:the structure of which is proven by ultrared spectra Analysis:
Berechnet: 50,77$ 0 3»1# H 21,5* Ii Gefunden: 50,8* C 3,2# H 21, JjS H.Calculated: $ 50.77 0 3 »1 # H 21.5 * Ii Found: 50.8 * C 3.2 # H 21, JjS H.
Das In praktisch quantitativer Ausbeute erhaltene dreidimensionale Polymerisat zeigt sich bis zu Temperaturen Über 300 0O als stabil· Es ist in allen bekannten lösungsmitteln unlöslich, einsehliesslich jenen für die Cyanursäure wie Dlmethylformaaid, Dietthylßulfoxyd usw· The three-dimensional polymer, obtained in practically quantitative yield, is stable up to temperatures of over 300 0 O. It is insoluble in all known solvents, including those for cyanuric acid such as methyl formamide, diethyl sulfoxide, etc.
Beispiel 2Example 2
Uta löst bti 60 0O «in Hol Cyanursäure In 2000 oa? wasserfrei·* DiMethylfoma*id und fUgt dieser Lesung 10 oe5 Triethylamin «u, dann nach und nach 1,5 Hol Diieooyanat der Chlornethylphosphon-•fture der Poreel ClCH2-PO(ICO)2* Man erhitet anachllteaend auf 1SO - 170 0Q »thrend einer Stunde unter Rüokfluse und entfernt inter Terainderte« Druok das DieethylforBamid. tlan erhfilt β· 400 β tine· festen Produktes, weichte Ik weeentliohtn aus tineo Ar«itl»tfielooalfn ftOfm&rUmt i«r ArtUta dissolves bti 60 0 O «in Hol cyanuric acid In 2000 oa? anhydrous · * DiMethylfoma * id and add to this reading 10 oe 5 triethylamine «u, then gradually 1.5 hol diiooyanate of the chloromethylphosphonate of the poreel ClCH 2 -PO (ICO) 2 * The temperature is increased to 1SO - 170 0 For an hour under ruffle and remove inter terainderte Druok the methyl form amide. tlan receives β · 400 β tine · solid product, softened Ik weeentliohtn from tineo Ar «itl» tfielooalfn ftOfm & rUmt i «r Art
908837/1509908837/1509
I O 3 O UO -J IO 3 O UO -J
Η· 107Η 107
O * OO * O
>8 o A > 8 o A
....* Χϊ - OO - HE - P - BH ~ 00 - J 1 ,0 β 0 OB4 0-4 C .... * Χ ϊ - OO - HE - P - BH ~ 00 - J 1 , 0 β 0 OB 4 0-4 C
besteht« Analysesconsists" Analyzes
Bereefcnats 22^55^ C 1,5?ί:Η 21,0Ji ϊ 11,65Γ Ρ 13,55^ Cl Gefimden* 21r9?t C 1 f 7?6 H 21,35* N t1»y^ Ϊ 13t4?iBereefcnats 22 ^ 55 ^ C 1.5? Ί: Η 21,0Ji ϊ 11.65 Γ Ρ 13.55 ^ Cl Gefimden * 21 r 9? T C 1 f 7? 6 H 21.35 * N t1 »y ^ Ϊ 13 t 4? I
Beispiel 3Example 3
■ LIan löst 20 g Trimathylbenzylammoniumhydroxycl Ια 1,5 Mol■ LIan dissolves 20 g of trimethylbenzylammonium hydroxyl Ια 1.5 mol
as der phenylphosphonigen Säure alt der Formel CO)7 und fügt nach und nach ein Mol Cyanursäure hinstto Wl-ihre- <1 da3 Gemi^oh auf 120 0C gebracht wird, löst sieh die Q$e>r\T&:im?3 auf und unmittalbar danach tritt die Polyaerieation su e.-ner hirton und unlöslichen nasse eia«As the phenylphosphonous acid old of the formula CO) 7 and gradually adds a mole of cyanuric acid to Wl-your- <1 da3 Gemi ^ oh is brought to 120 0 C, see the Q $ e> r \ T &: im? 3 on and immediately afterwards the polyaerieation su e.-ner hirton and insoluble wet egg "
erhal^iiiQ Produkt besteht im wesentlichen aus eine« dreidimensionalen Polymerisat der ArIget ^ iiiQ product consists essentially of a « three-dimensional polymer from ArI
9098377ΐ55Ϊ99098377ΐ 5 5Ϊ9
1595116315951163
R. 107R. 107
- CO - HH - P - HS - CO -- CO - HH - P - HS - CO -
> · «·»N Jf> · «·» N Jf
O »J JO »J J
IT- CO- MH. P- HS- CO - /Λτ V/° °6H5 0*0 iIT- CO- MH. P- HS- CO - / Λτ V / ° ° 6 H 5 0 * 0 i
• I• I
Die Struktur wird durch die !Ergebnisse der Eleaentaranalya· bestätigt»The structure is determined by the results of the Eleaentaranalya confirmed"
Berechnet: 43»2# 0 2,6£ H 2O9I^V 1I9 ffefundens 42,8$ C 2t6^C H 20,73* H 11 »2# PCalculated: 43 »2 # 0 2.6 £ H 2O 9 I ^ V 1I 9 ff found 42.8 $ C 2 t 6 ^ CH 20.73 * H 11» 2 # P
909837/1509909837/1509
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR4981A FR1459745A (en) | 1964-06-02 | 1964-06-02 | Three-dimensional polymers, obtained from cyanuric acid and diisocyanic esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1595063A1 true DE1595063A1 (en) | 1969-09-11 |
Family
ID=9691910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651595063 Pending DE1595063A1 (en) | 1964-06-02 | 1965-05-28 | Process for the production of three-dimensional polymers from isocyanuric acid and diisocyanuric acid ester |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1595063A1 (en) |
| FR (1) | FR1459745A (en) |
| GB (1) | GB1079675A (en) |
-
1964
- 1964-06-02 FR FR4981A patent/FR1459745A/en not_active Expired
-
1965
- 1965-05-28 DE DE19651595063 patent/DE1595063A1/en active Pending
- 1965-06-02 GB GB2355465A patent/GB1079675A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1079675A (en) | 1967-08-16 |
| FR1459745A (en) | 1966-11-25 |
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