SE455100B - Rigid, hardened solid polyurethane product based on an ammonia or aminitiated polyethylene poly, an organic polyisocyanate and a liquid modifier compound and preparation process - Google Patents
Rigid, hardened solid polyurethane product based on an ammonia or aminitiated polyethylene poly, an organic polyisocyanate and a liquid modifier compound and preparation processInfo
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- SE455100B SE455100B SE7906906A SE7906906A SE455100B SE 455100 B SE455100 B SE 455100B SE 7906906 A SE7906906 A SE 7906906A SE 7906906 A SE7906906 A SE 7906906A SE 455100 B SE455100 B SE 455100B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
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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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
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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)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
455 100 formen har produkterna tillräcklig hàllfasthet för att han- teras och har normalt tillräcklig hàllfasthet för att användas för sitt slutliga ändamål; de fysikaliska egenskaperna kan emellertid, om så önskas, vanligtvis förbättras genom efter- härdning vid förhöjda temperaturer. 455 100 mold, the products have sufficient strength to be handled and normally have sufficient strength to be used for their final purpose; however, the physical properties can, if desired, usually be improved by post-curing at elevated temperatures.
De snabbhärdande, fasta, styva polyuretanprodukterna enligt föreliggande uppfinning erhålles genom: blandning och om- sättning av (A) ammoniak eller en amininitíerad polyeterpolyol med en ekvivalentvikt av från 50 till mindre än 250, företrä- desvis fràn 50 till 200, med (B) ett organiskt polyisocyanat som innehåller en aromatisk ring i närvaro av (C) en flytande modifieringsmedelsförening som har en kokpunkt över l50°C som väljes bland organiska fosfater, organiska fosfiter och orga- niska fosfonater och blandningar därav; vari komponenterna (A) och (B) finnes närvarande i sådana mängder att ett NCO:OH- -förhållande av från 0,8 till 1,5 tillhandahàlles, företrädes- vis fràn 0,9 till 1,2 och lämpligast från 0,95 till l,05, och komponent (C) användes i en mängd av från 5% till 60%, före- trädesvis 15-40 viktprocent, räknat pà den sammanlagda vikten av (A), (B) och (C).The fast-curing, solid, rigid polyurethane products of the present invention are obtained by: mixing and reacting (A) ammonia or an aminitated polyether polyol having an equivalent weight of from 50 to less than 250, preferably from 50 to 200, with (B) an organic polyisocyanate containing an aromatic ring in the presence of (C) a liquid modifier compound having a boiling point above 150 ° C selected from organic phosphates, organic phosphites and organic phosphonates and mixtures thereof; wherein components (A) and (B) are present in such amounts that an NCO: OH ratio of from 0.8 to 1.5 is provided, preferably from 0.9 to 1.2 and most preferably from 0.95. to 1.05, and component (C) is used in an amount of from 5% to 60%, preferably 15-40% by weight, based on the total weight of (A), (B) and (C).
Lämpliga amininitierade polyeterpolyoler som användes som komponent (A) i föreliggande uppfinning innefattar exempelvis de som framställes genom omsättning av en alkylenoxid med ammoniak eller en amin med 3-8 aktiva väteatomer.Suitable amine-initiated polyether polyols used as component (A) in the present invention include, for example, those prepared by reacting an alkylene oxide with ammonia or an amine having 3-8 active hydrogen atoms.
Lämpliga aminer innefattar exempelvis ammoniak, etylendiamin, 1,3-diaminopropan, 1,4-diaminobutan, 1,5-díaminopropan, 1,6- -diaminohexan, dietylentriamin, trietylendiamin, tetraetylen- pentamin, pentaetylenhexamin och blandningar därav.Suitable amines include, for example, ammonia, ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diamaminopropane, 1,6-diaminohexane, diethylenetriamine, triethylenediamine, tetraethylenepentamine, pentaethylenehexamine and mixtures thereof.
Lämpliga alkylenoxider innefattar exempelvis etylenoxid, 1,2-propylenoxid, 1,2-butylenoxid, 2,3-butylenoíid, 455 100 styrenoxid, epiklorhydrín, epibromhydrin, epíjodhydrin och blandningar därav.Suitable alkylene oxides include, for example, ethylene oxide, 1,2-propylene oxide, 1,2-butylene oxide, 2,3-butylenoid, 455,100 styrene oxide, epichlorohydrin, epibromohydrin, epiodhydrin and mixtures thereof.
Lämpliga organiska polyisocyanater som användes som komponent (B) i föreliggande uppfinning innefattar exempelvis varje organisk polyi ocyanat med två eller flera NCO-grupper per molekyl och icke nâgra andra substituenter med förmåga till omsättning med hydroxigrupperna i de amininitierade polyoxi- alkylenföreningar som användes som komponent (C). Isocyanat- grupperna behöver icke vara insubstituerade i den aromatiska ringen. Lämpliga sådana polyisocyanater innefattar exempel- vis 2,4-toluendiisocyanat, 2,6-toluendiisocyanat, p,p'-dife- nylmetandiisocyanat, p-fenylendiisocyanat, hydrerat metylen- difenyldiisocyanat, naftalendiisocyanat, dianisidindiisocya- nat, polymetylenpolyfenyl-isocyanat och blandningar av två eller flera polyisocyanater.Suitable organic polyisocyanates used as component (B) in the present invention include, for example, any organic polyiocyanate having two or more NCO groups per molecule and not any other substituents capable of reacting with the hydroxy groups of the amine-initiated polyoxyalkylene compounds used as component (B). C). The isocyanate groups need not be unsubstituted in the aromatic ring. Suitable such polyisocyanates include, for example, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, p, p'-diphenylmethane diisocyanate, p-phenylene diisocyanate, hydrogenated methylene diphenyl diisocyanate, naphthalene diisocyanate, dianisidine diethylyl isocyanate and ions. or more polyisocyanates.
Andra organiska isocyanater som lämpligen användes och som skall innefattas i uttrycket organisk polyisocyanat innefat- tar isocyanatterminerade förpolymer framställda av de tidiga- re nämnda polyolerna och de ovan nämnda isocyanaterna.Other organic isocyanates which are suitably used and which are to be included in the term organic polyisocyanate include isocyanate-terminated prepolymer prepared from the aforementioned polyols and the above-mentioned isocyanates.
Lämpliga organofosforföreningar som användes som den flytande modifieringsföreningen, komponent C, innefattar exempelvis organofosfater, organofosfiter och organofosfonater som har kokpunkter över l50°C.Suitable organophosphorus compounds used as the liquid modifying compound, component C, include, for example, organophosphates, organophosphites and organophosphonates having boiling points above 150 ° C.
Organofosfater, -fosfiter och -fosfonater som användes som den flytande modifieringsföreningen innefattar de flytande föreningar som motsvarar formlerna Y y Y R -NIÅ-o-R ; (R ) - -o-f- :-: - _ _ _ _ .-.._ 3 o O l l 3 n v ( )n, 113 o i? o al c...(a2)3-r_-o-1'='-(a.),_ ' O ' A. ..Organophosphates, phosphites and phosphonates used as the liquid modifying compound include the liquid compounds corresponding to the formulas Y y Y R -NIÅ-o-R; (R) - -o-f-: -: - _ _ _ _.-.._ 3 o O l l 3 n v () n, 113 o i? o al c ... (a2) 3-r_-o-1 '=' - (a.), _ 'O' A. ..
I az R 2 455 100 vari Rl, R2 och R3 oberoende väljes bland alkyl, alkoxiaryl, aryloxiaryl, alkaryl, aralkylgrupper och halogensubstituerade derivat därav. Y är syre eller svavel, X är en halogen, dvs. klor, fluor, brom eller jod, n har ett värde av l eller 2.In az R 2 455 100 wherein R 1, R 2 and R 3 are independently selected from alkyl, alkoxyaryl, aryloxyaryl, alkaryl, aralkyl groups and halogen-substituted derivatives thereof. Y is oxygen or sulfur, X is a halogen, ie. chlorine, fluorine, bromine or iodine, n has a value of 1 or 2.
Lämpliga sådana föreningar innefattar exempelvis tri-n-butyl- fosfat, trietylfosfat, trikresylfosfat, tris-(/Ö-kloretyl)- fosfat, tris-(2,3-dibrompropyl)-fosfat, butyldiklorfosfat, 2-kloretyldiklorfosfat, etyldiklorfosfat, dietylfluorfosfat, bis(2-kloretyl)-fluorfosfat, dibutylklorfosfat, isoamyldi- klortionofosfat, etyldibromtiofosfat, 2-klorfenyldiklorfos- fat, 2-2-metoxifenyldiklorfosfat, 2-fenoxifenyldiklorfosfat, 2-kloretyldiklorfosfit,tris-(2-kloretyl)-fosfit, tributyl- fosfit, trikresylfosfit, trietylfosfit, dietylisoamylfosfo- nat,dietyletylfos&nmt, dimetylmetylfosfonat, dietylmetylfosfo- nat, diisobutylisobutylfosfonat och bis(2-brompropyl)-2- brompropanfosfonat.Suitable such compounds include, for example, tri-n-butyl phosphate, triethyl phosphate, tricresyl phosphate, tris - (β-chloroethyl) phosphate, tris- (2,3-dibromopropyl) phosphate, butyl dichlorophosphate, 2-chloroethyldichlorophosphate, ethyldichlorophate, ethyldichlorophate, ethyldichloro bis (2-chloroethyl) -fluorophosphate, dibutylchlorophosphate, isoamyl dichlorothiophosphate, ethyl dibromothiophosphate, 2-chlorophenyldichlorophosphate, 2-2-methoxyphenyl dichlorophosphate, 2-phenoxyphenyldichlorophosphate, 2-chlorophytophytylphlor, , tricresyl phosphite, triethyl phosphite, diethylisoamylphosphonate, diethylethylphosphonate, dimethylmethylphosphonate, diethylmethylphosphonate, diisobutylisobutylphosphonate and bis (2-bromopropyl) -2-bromopropane phosphonate.
Uttrycket "flytande modifieringsmedel som kokar över l50°C“ innefattar eutektiska blandningar av de tidigare beskrivna grupperna av föreningar som utgör fasta substanser vid atmos- färstryck men de eutektiska blandningarna utgör en vätska vid rumstemperatur och atmosfärstryck som har kokpunkter över l50°C. I definitionen innefattas även de fasta föreningar av de tidigare beskrivna grupperna som är lösta i en flytande förening av någon av de tidigare beskrivna grupperna av fö- reningar som har kokpunkter över l50°C vari den resulterande lösningen utgör en vätska vid standardbetingelser beträffande temperatur och tryck och som har kokpunkter vid atmosfärs- tryck över 15o°c .The term "liquid modifier boiling above 150 ° C" includes eutectic mixtures of the previously described groups of compounds which constitute solids at atmospheric pressure but the eutectic mixtures constitute a liquid at room temperature and atmospheric pressure having boiling points above 150 ° C. also includes the solid compounds of the previously described groups which are dissolved in a liquid compound of any of the previously described groups of compounds having boiling points above 150 ° C wherein the resulting solution constitutes a liquid under standard conditions of temperature and pressure and which has boiling points at atmospheric pressure above 15o ° c.
Andra föreningar innefattande inerta fyllmedel, exempelvis sand, mikroballonger, glasfibrer, asbest, aluminiumgranulat och kiselkarbidpulver, färgande medel, såsom pigment och färgämnen innefattande exempelvis kromoxid, ferrioxid och blandningar därav kan användas i kompositionerna enligt före- liggande uppfinning. 455 100 Lämpliga material av vilka lämpliga formar för gjutning av kompositionerna enligt föreliggande uppfinning kan framstäl- las innefattar polymer, exempelvis polyeten, polypropen, de- ras sampolymerer och liknande, polyuretaner, polysiloxanelas- ter, polyetylentereftalat, härdade polyepoxider och bland- ningar därav.Other compounds including inert fillers, for example sand, microballoons, glass fibers, asbestos, aluminum granules and silicon carbide powder, coloring agents such as pigments and dyes including, for example, chromium oxide, ferric oxide and mixtures thereof may be used in the compositions of the present invention. Suitable materials from which suitable molds for molding the compositions of the present invention can be prepared include polymers, for example, polyethylene, polypropylene, their copolymers and the like, polyurethanes, polysiloxane elastomers, polyethylene terephthalate, cured polyepoxides, and mixtures thereof.
Det är föredraget att använda relativt tunnväggiga formar eller formar som har låg värmekapacitet eller värmelednings- förmåga. Tunga formar framställda av material med relativt hög värmeledningsförmåga, såsom aluminium, koppar, järn eller stål kan ge upphov till härdningsproblem, dvs. reaktanterna kanske inte med lätthet kan uttagas ur formen såvida formen icke 1 förväg uppnettee till so-9o°c, 1 synnerhet vid gjut- ning av relativt tunna sektioner. Material med hög värmeled- ningsförmåga, såsom koppar eller aluminium, kan emellertid användas som tunnväggiga formar utan föruppvärmning om värme- kapaciteten för formen är relativt låg jämfört med den värme- mängd som frigöres vid gjutningen.It is preferred to use relatively thin-walled molds or molds that have low heat capacity or thermal conductivity. Heavy molds made of materials with relatively high thermal conductivity, such as aluminum, copper, iron or steel can give rise to hardening problems, ie. the reactants may not be easily removed from the mold unless the mold is pre-raised to 70 DEG C., especially when casting relatively thin sections. However, materials with high thermal conductivity, such as copper or aluminum, can be used as thin-walled molds without preheating if the heat capacity of the mold is relatively low compared to the amount of heat released during casting.
Kompositionerna enligt föreliggande uppfinning är lämpliga som, men icke begränsade till sådana användningar som, ett gjutmaterial för framställning av lagerytor, ringformiga mel- lanläggssprickor, speldelar, dekorativa föremål, möbler eller möbelkomponenter, kugghjul eller andra maskindelar, gängade skyddande pluggar och kåpor.The compositions of the present invention are suitable as, but not limited to, such uses as a casting material for making bearing surfaces, annular spacers, game pieces, decorative objects, furniture or furniture components, gears or other machine parts, threaded protective plugs and covers.
I vissa fall är en blandning av komponenterna (A) och (B) så okombinerbara att reaktionen sker mycket långsamt (dvs. stel- ning kräver mer än 10 minuter). När detta inträffar kan en modifieringsförening som har en hög dielektrisk konstant bestämd vid 20°C och en frekvens av l x 104 cykler per sekund större än 4 och företrädesvis större än 8, exempelvis etyl- acetoacetat, propylenkarbonat, acetofenon och dimetylftalat användas för att göra blandningen kombinerbar. Dessa före- ningar bidrar till att göra komponenterna (A) och (B) mera kombinerbara genom att de kan blandas och snabbt kommer att 455 100 reagera och ge en snabbhärdande fast substans som är uttag- bar ur formen inom kortare tid än 5 minuter.In some cases a mixture of components (A) and (B) is so uncombined that the reaction takes place very slowly (ie solidification requires more than 10 minutes). When this occurs, a modifying compound having a high dielectric constant determined at 20 ° C and a frequency of 1x104 cycles per second greater than 4 and preferably greater than 8, for example ethyl acetoacetate, propylene carbonate, acetophenone and dimethyl phthalate may be used to make the mixture. combinable. These compounds help to make components (A) and (B) more compatible in that they can be mixed and will rapidly react and give a fast-curing solid which can be removed from the mold in less than 5 minutes.
Modifierings-blandbarhetsföreningarna användes i en mängd inom intervallet 2,5-60% av den sammanlagda vikten av kompo- nenterna (A), (B) och(C) och sådana mängder är innefattade såsom en del av den totala mängden av komponent (C) som fin- nes närvarande i kompositionen.The modifiable miscibility compounds are used in an amount in the range of 2.5-60% of the total weight of the components (A), (B) and (C) and such amounts are included as part of the total amount of component (C). ) which is present in the composition.
I var och en av exemplen och jämförelseförsöken blandades alla komponenterna med undantag av polyisocyanatet omsorgs- fullt samman och därefter blandades polyisocyanatet hastigt in i blandningen och hälldes omedelbart i en polyetenform eller en skålav polyetylentereftalat.In each of the examples and comparative experiments, all the components except the polyisocyanate were thoroughly mixed together and then the polyisocyanate was rapidly mixed into the mixture and immediately poured into a polyethylene mold or a bowl of polyethylene terephthalate.
Kompositionerna, härdingstider och formuttagningstider och egenskaper för produkterna redovisas i följande tabell. 1 lvnztunl.. ,..!||1|, .l|..| ...l .|. . 455 100 .äwficuäfin fi wwwmnæfln uwääñvomflšom acw vëflåømw .Eu nflfi mmfiÉ âëå mw Cm. wuußum 7 umnøumcnn wuosm HÅ om om ov h. om 4 mm m m .xm ow mm muwæum uwflwuwsun wuosw .fl Å om om mm H mm m om 4 N Jfi mæ Gm wunwum »wfimfn mäoå åå om mN om m om m mm m H .å Mußumm zoo mwflwmbm mm.o .i ll || øwmnfi om 4 om m m xmmuwm uoxoflumw m>0um oømwflflß :oo mwmåwm :Bmäw .wwflmä S5 i ä å âmfi om m å 4 4 šmää Hmmcflcvmnmcšm m=U\m GwEuOu H: mcflcfiwuw Emuw å Emnw å Emuw å .MG xßmuww uwflw »wfimän møëmßv: »Q .xmw bmflwöäfi. nwmmxmämm Hmm .xww H En. U .Éwcoàobm m unwcomoöm 4 ucwcêöm uøflw mmflš fi u? . Håäå 455 100 De amíninitierade polyoler som användes som komponent (A) í föregående exempel och jämförelseförsök var följande; Tyg A utgjorde en aminoetyletanolamin omsatt med propylenoxid i ett molförhàllande av ungefär 1:3 med en hydroxiekvivalentvikt av ungefär 72.The compositions, curing times and mold removal times and properties of the products are reported in the following table. 1 lvnztunl .., ..! || 1 |, .l | .. | ... l. |. . 455 100 .äw fi cuä fi n fi wwwmnæ fl n uwääñvom fl šom acw vë fl åømw .Eu n flfi mm fi É âëå mw Cm. wuußum 7 umnøumcnn wuosm HÅ om om ov h. om 4 mm mm .xm ow mm muwæum uw fl wuwsun wuosw .fl Å om om mm H mm m om 4 N J fi mæ Gm wunwum »w fi mfn mäoå åå om mN om m om m mm m H .å Mußumm zoo mw fl wmbm mm.o .i ll || øwmn fi om 4 om mm xmmuwm uoxo fl umw m> 0um oømw flfl ß: oo mwmåwm: Bmäw .ww fl mä S5 i ä å âm fi om m å 4 4 šmää Hmmc fl cvmnmcšm m = U \ m GwEuOu Emw u »hw m: w. w fi men møëmßv: »Q .xmw bm fl wöä fi. nwmmxmämm Hmm .xww H En. U .Éwcoàobm m unwcomoöm 4 ucwcêöm uø fl w mm fl š fi u? . The amine-initiated polyols used as component (A) in the previous example and comparative experiments were as follows; Fabric A was an aminoethylethanolamine reacted with propylene oxide in a molar ratio of about 1: 3 with a hydroxy equivalent weight of about 72.
Tyg B utgjorde reaktionsprodukten av dietylentríamin med propylenoxid í ett molförhållande av ungefär 1:5 och med en OH-ekvívalentvíkt av ungefär 76.Fabric B was the reaction product of diethylenetriamine with propylene oxide in a molar ratio of about 1: 5 and with an OH equivalent weight of about 76.
De polyisocyanater som användes som komponent (B) i föregående exempel och jämförelseförsök var följande: Tyg A utgjorde en 80/20-blandning av 2,4-/2,6-isomererna av toluendiisocyanat med en NCO-ekvívalentvikt av ungefär 87.The polyisocyanates used as component (B) in the previous example and comparative experiments were as follows: Fabric A was an 80/20 mixture of the 2,4- / 2,6-isomers of toluene diisocyanate with an NCO equivalent weight of about 87.
De modífíeringsföreningar som användes som komponent (C) i föregående exempel och jämförelseförsök var följande; Tyg H Tríkresylfosfat Tyg I Tri-n-butylfosfit Tyg J Bis(2-brompropyl)-2-brompropanfosfonat Vi “AIThe modifying compounds used as component (C) in the previous example and comparative experiments were as follows; Fabric H Tricresyl phosphate Fabric I Tri-n-butyl phosphite Fabric J Bis (2-bromopropyl) -2-bromopropane phosphonate Vi
Claims (4)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US22178472A | 1972-01-28 | 1972-01-28 |
Publications (2)
Publication Number | Publication Date |
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SE7906906L SE7906906L (en) | 1979-08-17 |
SE455100B true SE455100B (en) | 1988-06-20 |
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Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
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SE7301154A SE447576B (en) | 1972-01-28 | 1973-01-26 | Rigid, hardened solid polyurethane product as well as manufacturing process thereof |
SE7906907A SE424001B (en) | 1972-01-28 | 1979-08-17 | Rigid, Rapid, Solid Polyurethane Product, Which Modifier Contains Chlorinated Aliphatic Compounds, and Procedures for Preparation of Polyurethane Product |
SE7906906A SE455100B (en) | 1972-01-28 | 1979-08-17 | Rigid, hardened solid polyurethane product based on an ammonia or aminitiated polyethylene poly, an organic polyisocyanate and a liquid modifier compound and preparation process |
SE7906908A SE455101B (en) | 1972-01-28 | 1979-08-17 | Rigid, hardened, solid polyurethane product based on an ammonia or amininitiated polyether polyol, an organic polyisocyanate, and a liquid modifier compound and preparation process |
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SE7301154A SE447576B (en) | 1972-01-28 | 1973-01-26 | Rigid, hardened solid polyurethane product as well as manufacturing process thereof |
SE7906907A SE424001B (en) | 1972-01-28 | 1979-08-17 | Rigid, Rapid, Solid Polyurethane Product, Which Modifier Contains Chlorinated Aliphatic Compounds, and Procedures for Preparation of Polyurethane Product |
Family Applications After (1)
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SE7906908A SE455101B (en) | 1972-01-28 | 1979-08-17 | Rigid, hardened, solid polyurethane product based on an ammonia or amininitiated polyether polyol, an organic polyisocyanate, and a liquid modifier compound and preparation process |
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JP (1) | JPS5615416B2 (en) |
AR (1) | AR195697A1 (en) |
AU (1) | AU476706B2 (en) |
BE (1) | BE794607A (en) |
CA (1) | CA997892A (en) |
DE (1) | DE2303669A1 (en) |
ES (1) | ES411019A1 (en) |
FR (1) | FR2169371B1 (en) |
GB (1) | GB1413761A (en) |
IT (1) | IT977067B (en) |
NL (1) | NL7301001A (en) |
SE (4) | SE447576B (en) |
ZA (1) | ZA73324B (en) |
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US4476292A (en) * | 1984-01-30 | 1984-10-09 | Ciba-Geigy Corporation | Castable polyurethane systems |
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US3102875A (en) * | 1953-08-07 | 1963-09-03 | Monsanto Chemicals | Polyurethane reaction product and method for making same |
US3143517A (en) * | 1953-08-07 | 1964-08-04 | Monsanto Co | Substantially non-porous polyurethane plastic and method for producing same |
FR1413775A (en) * | 1963-11-14 | 1965-10-08 | Ici Ltd | Polyurethanes manufacturing process |
US3378511A (en) * | 1965-01-15 | 1968-04-16 | Dow Chemical Co | Polymeric urethane compositions |
US3440224A (en) * | 1966-03-15 | 1969-04-22 | Ashland Oil Inc | Polyurethane compositions and methods for preparing such |
US3449320A (en) * | 1966-04-21 | 1969-06-10 | Union Carbide Corp | Hexachlorobutadiene polyol compounds |
US3489723A (en) * | 1966-12-06 | 1970-01-13 | Nopco Chem Co | Two-component castable polyurethane elastomer composition and use |
GB1279415A (en) * | 1969-01-09 | 1972-06-28 | Ici Ltd | New polymerisation process |
DE1923934A1 (en) * | 1969-05-10 | 1970-11-19 | Dynamit Nobel Ag | Process for the production of polyurethanes |
JPS5017519B2 (en) * | 1972-01-11 | 1975-06-21 |
-
0
- BE BE794607D patent/BE794607A/en not_active IP Right Cessation
-
1973
- 1973-01-11 CA CA161,076A patent/CA997892A/en not_active Expired
- 1973-01-16 ZA ZA730324A patent/ZA73324B/en unknown
- 1973-01-19 AU AU51251/73A patent/AU476706B2/en not_active Expired
- 1973-01-22 GB GB311673A patent/GB1413761A/en not_active Expired
- 1973-01-24 AR AR246268A patent/AR195697A1/en active
- 1973-01-24 NL NL7301001A patent/NL7301001A/xx not_active Application Discontinuation
- 1973-01-25 DE DE2303669A patent/DE2303669A1/en not_active Ceased
- 1973-01-26 FR FR7302926A patent/FR2169371B1/fr not_active Expired
- 1973-01-26 IT IT47910/73A patent/IT977067B/en active
- 1973-01-26 ES ES411019A patent/ES411019A1/en not_active Expired
- 1973-01-26 JP JP1038973A patent/JPS5615416B2/ja not_active Expired
- 1973-01-26 SE SE7301154A patent/SE447576B/en unknown
-
1979
- 1979-08-17 SE SE7906907A patent/SE424001B/en not_active IP Right Cessation
- 1979-08-17 SE SE7906906A patent/SE455100B/en not_active IP Right Cessation
- 1979-08-17 SE SE7906908A patent/SE455101B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JPS4884196A (en) | 1973-11-08 |
SE7906908L (en) | 1979-08-17 |
ZA73324B (en) | 1973-10-31 |
SE7906906L (en) | 1979-08-17 |
ES411019A1 (en) | 1976-04-01 |
SE447576B (en) | 1986-11-24 |
SE455101B (en) | 1988-06-20 |
JPS5615416B2 (en) | 1981-04-10 |
GB1413761A (en) | 1975-11-12 |
FR2169371B1 (en) | 1976-11-05 |
NL7301001A (en) | 1973-07-31 |
AU476706B2 (en) | 1976-09-30 |
IT977067B (en) | 1974-09-10 |
BE794607A (en) | 1973-07-26 |
CA997892A (en) | 1976-09-28 |
DE2303669A1 (en) | 1973-08-02 |
AU5125173A (en) | 1974-07-25 |
AR195697A1 (en) | 1973-10-31 |
FR2169371A1 (en) | 1973-09-07 |
SE7906907L (en) | 1979-08-17 |
SE424001B (en) | 1982-06-21 |
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