NO752002L - - Google Patents
Info
- Publication number
- NO752002L NO752002L NO752002A NO752002A NO752002L NO 752002 L NO752002 L NO 752002L NO 752002 A NO752002 A NO 752002A NO 752002 A NO752002 A NO 752002A NO 752002 L NO752002 L NO 752002L
- Authority
- NO
- Norway
- Prior art keywords
- polyol
- composition according
- aliphatic
- compound
- polyhydroxy
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 49
- 229920005862 polyol Polymers 0.000 claims description 39
- 150000003077 polyols Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229920000570 polyether Polymers 0.000 claims description 19
- 229920001228 polyisocyanate Polymers 0.000 claims description 19
- 239000005056 polyisocyanate Substances 0.000 claims description 19
- 239000004576 sand Substances 0.000 claims description 17
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- -1 aliphatic diamine Chemical class 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000011236 particulate material Substances 0.000 claims description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- KXUSQYGLNZFMTE-UHFFFAOYSA-N hex-2-yne-1,1-diol Chemical compound CCCC#CC(O)O KXUSQYGLNZFMTE-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000011230 binding agent Substances 0.000 description 12
- 239000004721 Polyphenylene oxide Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000000465 moulding Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- RGHNJXZEOKUKBD-NRXMZTRTSA-N (2r,3r,4r,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-NRXMZTRTSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000010450 olivine Substances 0.000 description 1
- 229910052609 olivine Inorganic materials 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22C—FOUNDRY MOULDING
- B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
- B22C1/16—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents
- B22C1/20—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents
- B22C1/22—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins
- B22C1/2233—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- B22C1/2273—Polyurethanes; Polyisocyanates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22C—FOUNDRY MOULDING
- B22C3/00—Selection of compositions for coating the surfaces of moulds, cores, or patterns
-
- 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
- C08G18/3203—Polyhydroxy compounds
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
- C08G18/679—Acetylenic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Description
Foreliggende oppfinnelse angår en fremgangsmåte for belegning av et materiale hvorved man på materialet appliserer en polyisocyanatforbindelse og en polyhydroxyforbindeise samt eventuelt et opplosningsmiddel, hvorefter det belagte materiale, om nodvendig, formes, og belegget herdes ved hjelp av en katalysator, samt en komposisjon for utforelse av fremgangsmåten. Oppfinnelsen er spesielt godt anvendbar på partikkelformige materi-aler slik som sand, som ifolge den såkaldte cold-box metoden formes til stopekjerner og -former, men kan naturligvis også anvendes på ikke-partikkelformig materiale for overflatebelegning av dette. Komposisjonen ifolge oppfinnelsen anvendes herved en-ten som ren fi'lmdannende komposisjon eller som bindemiddelkom-posisjon. The present invention relates to a method for coating a material by which a polyisocyanate compound and a polyhydroxy compound are applied to the material, as well as possibly a solvent, after which the coated material is, if necessary, shaped and the coating is hardened with the aid of a catalyst, as well as a composition for carrying out the procedure. The invention is particularly well applicable to particulate materials such as sand, which according to the so-called cold-box method is formed into stope cores and forms, but can of course also be applied to non-particulate material for surface coating thereof. The composition according to the invention is used here either as a pure film-forming composition or as a binder composition.
Ved fremstilling av stopekjerner og -former har man stadig mer gått over til å anvende den såkaldte cold-box metode. Denne metode som er beskrevet blant annet i svensk utlegnings-skrift 314.477 og 343.310 har den stote fordel sammenlignet med tidligere metoder at den ikke krever noen oppvarmnin g av formmassen i og for herdning. Metoden går i korthet ut på at man til-bereder en blanding av partikkelformig materiale, fortrinnsvis sand, og et bindemiddel, hvorefter blandingen gis onsket form og sluttelig herdes ved hjelp av en katalysator. In the production of stop cores and molds, the so-called cold-box method has increasingly been used. This method, which is described among other things in Swedish design documents 314,477 and 343,310, has the major advantage compared to previous methods that it does not require any heating of the molding compound during and for hardening. Briefly, the method involves preparing a mixture of particulate material, preferably sand, and a binder, after which the mixture is given the desired shape and finally hardened with the help of a catalyst.
De ifolge disse utlegningsskrifter tidligere anvendte bindemidler har tidligere vært basert på oppløsninger av poly-isocyanatf orbindelser og fenol-formaldehydharpikser, syntetiske eller naturlig torkende oljer. The binders previously used according to these explanatory documents have previously been based on solutions of polyisocyanate compounds and phenol-formaldehyde resins, synthetic or naturally drying oils.
Stopekjerner tilvirket med disse kjente bindemidler har imidlertid flere ulemper. De stopekjerner og -former som er tilvirket med disse kjente bindemidler kan ikke tilpasses til de be- tingelser som råder under hver spesiell metallstopning. Dette har tilfolge at et flertall feilaktigheter fremkommer, hvilke forer til dyre efterbehandlingsoperasjoner eller kassering av stopegodset. Således kan nevnes at stopekjerner tilvirket ifolge de tidligere beskrevne metoder er folsomme for varmesjokk, og altså lett gir sprekk^annelse ved metallstopningen. En karakte-ristisk feilaktighet ved anvendelse av fenolharpikser er dannel-se av såkaldte "skorper". Likeså er kjernesmuldringen ved stopning av lettmetall ikke akseptabel. For de fenol-formaldehyd-baserte bindemidler gjelder dessuten at monomer fenol henholdsvis formaldehyd erholdes sotn pyrolyseprodukter, hvilket medforer betydelige problemer med hensyn til det indre og ytre miljo. Stop cores made with these known binders, however, have several disadvantages. The plug cores and forms which are made with these known binders cannot be adapted to the conditions that prevail under each particular metal plug. This results in a large number of errors occurring, which lead to expensive post-processing operations or disposal of the stop goods. Thus, it can be mentioned that stop cores manufactured according to the previously described methods are sensitive to heat shock, and therefore easily crack when the metal is stopped. A characteristic error when using phenolic resins is the formation of so-called "crusts". Similarly, core crumbling when filling with light metal is not acceptable. For the phenol-formaldehyde-based binders, it also applies that monomeric phenol and formaldehyde respectively are obtained as pyrolysis products, which entails significant problems with regard to the internal and external environment.
Mange av ulempene med de tidligere anvendte fremgangs-måter er blitt eliminert ved den fremgangsmåte som er beskrevet i svensk patentsoknad 12377/72. Metoden ifolge denne soknad kjennetegnes ved at man som polyhydroxyforbindelser anvender visse spesielle alifatiske og aromatiske polyethre. En ulempe med disse polyethre er imidlertid at de gir forholdsvis lang-somt reaksjonsforlop, hvorfor de må anvendes i kombinasjon med en benzenforbindelse med minst to OH-grupper. Ved at andelen av benzenforbindelse er relativt hoy, gjenstår imidlertid mange av de problemer som er forbundet med de fenolbaserte bindemidler, ikke minst miljøproblemene. Many of the disadvantages of the previously used methods have been eliminated by the method described in Swedish patent application 12377/72. The method according to this application is characterized by the fact that certain special aliphatic and aromatic polyethers are used as polyhydroxy compounds. A disadvantage of these polyethers, however, is that they give a relatively slow course of reaction, which is why they must be used in combination with a benzene compound with at least two OH groups. As the proportion of benzene compounds is relatively high, however, many of the problems associated with the phenol-based binders remain, not least the environmental problems.
Disse problemer elimineres ifolge foreliggende oppfinnelse ved anvendelse av en polyhydroxyforbindelse som kan være These problems are eliminated according to the present invention by using a polyhydroxy compound which can be
helt fenolfri. Det er således ganske overraskende funnet at man ved å anvende som polyhydroxyforbindelse 5 - 100 vekt%, beregnet på den totale andel polyhydroxyforbindelse, én eller flere polyoler med 2-6, fortrinnsvis 2-3, endegrupper med formelen: completely phenol-free. It has thus been rather surprisingly found that by using as polyhydroxy compound 5 - 100% by weight, calculated on the total proportion of polyhydroxy compound, one or more polyols with 2-6, preferably 2-3, end groups with the formula:
kan oppnå en reaktivitet fullt sammenlignbar med reaktiviteten hos de tidligere anvendte fenolbaserte bindemidler, hvilken egenskap var den storste fordel med de sistnevnte bindemidler, can achieve a reactivity fully comparable to the reactivity of the previously used phenol-based binders, which property was the greatest advantage of the latter binders,
samtidig som ulempene hos de fenolbaserte bindemidler elimineres. Helt fenolfrie komposisj oner kan således erholdes ifolge oppfinnelsen, hvilket er en stor fordel ikke minst fra mi 1jovernssyns-punkt. at the same time as the disadvantages of the phenol-based binders are eliminated. Completely phenol-free compositions can thus be obtained according to the invention, which is a great advantage not least from the point of view of environmental protection.
Oppfinnelsen baserer seg således i prinsipp på anvendelse av folgende dioler som grunnbyggestener: The invention is thus based in principle on the use of the following diols as basic building blocks:
Ifolge en foretrukken utforelsesform for oppfinnelsen anvendes butendiol som polydl mens denne diol foreligger i flytende form ved romtemperatur, hvorved fremgangsmåten kan utfores helt opplosningsmiddelfritt. Dette er en meget stor fordel da man derved unngår mi 1joproblemer såvel som eksplosjonsfarer. Samme fordel kan også oppnåes med en blanding av butendiolen med butyndiolen og/eller noen av hexyndiolene.hvis butendiolen foreligger i en slik mengde at polyolkomponenten fremdeles er flyt ende. According to a preferred embodiment of the invention, butenediol is used as polydl while this diol is in liquid form at room temperature, whereby the method can be carried out completely solvent-free. This is a very big advantage as it avoids mi1jo problems as well as explosion hazards. The same advantage can also be achieved with a mixture of the butenediol with the butynediol and/or some of the hexynediols, if the butenediol is present in such an amount that the polyol component is still liquid.
Selvom de ovenfor angitte dioler kan anvendes som så-danne ved fremgangsmåten ifolge oppfinnelsen, kan det i mange tilfelle være onskelig med storre molekyler, hvilket innebærer at den for oppfinnelsen karakteristiske polyol kan uttrykkes som folger: Although the above-mentioned diols can be used as such in the method according to the invention, in many cases larger molecules may be desirable, which means that the polyol characteristic of the invention can be expressed as follows:
hvor R og R^har de ovenfor angitte betydninger, m = 2 - 6, fortrinnsvis 2 - 3, og X er en hvilken som helst innen dette fagområde tidligere kjent alifatisk, cycloalifatisk, aralifatisk, aromatisk eller heterocyclisk gruppe, fortrinnsvis en alifatisk gruppe. Gruppens X utseende er således ikke av avgjorende be-tydning for hensikten ifolge oppfinnelsen, men nevnte gruppe velges helt ifolge tidligere kjent teknikk efter de spesielle where R and R^ have the meanings given above, m = 2 - 6, preferably 2 - 3, and X is any previously known aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic group in this field, preferably an aliphatic group. The appearance of the group X is thus not of decisive importance for the purpose according to the invention, but said group is chosen entirely in accordance with prior art according to the special
egenskaper man onsker å oppnå i hvert enkelt tilfelle. Det ene-ste krav som stilles til polyolforbindeisen for at Snsket resul-tat ifolge oppfinnelsen skal oppnåes, er at dens molekylvekt ik-ke skal overstige lOOOO. Fortrinnsvis bor molekylvekten ikke characteristics one wishes to achieve in each individual case. The only requirement that is placed on the polyol binder in order for the desired result according to the invention to be achieved is that its molecular weight should not exceed lOOOO. Preferably, the molecular weight does not vary
overstige 8000, og helst ikke 6000. Gruppen X velges dessuten naturligvis slik at aromatisk struktur av fenolisk type i storst mulig grad unngåes, da de store fordeler med oppfinnelsen herved til en viss grad ville gå tapt. exceed 8000, and preferably not 6000. The group X is also naturally chosen so that aromatic structure of the phenolic type is avoided to the greatest extent possible, as the great advantages of the invention would thereby be lost to a certain extent.
Som eksempel på foretrukne typer av forbindelser fra hvilke X kan avledes, kan imidlertid angis alifatiske dicarbon-syrer, fortrinnsvis med 2-6 carbonatomer i alkylenkjeden, f.eks. adipinsyre, aromatiske isocyanater, f.eks. toluendiisocyanat, eller addisjonsprodukter med -NCO-endegrupper samt polyethre, i hvilket tilfelle polyhydroxyforbindelsen utgjores av en ester, et addukt med isocyanat henholdsvis et addukt med polyether. As examples of preferred types of compounds from which X can be derived, aliphatic dicarboxylic acids, preferably with 2-6 carbon atoms in the alkylene chain, can be mentioned, e.g. adipic acid, aromatic isocyanates, e.g. toluene diisocyanate, or addition products with -NCO end groups and polyether, in which case the polyhydroxy compound is made up of an ester, an adduct with isocyanate or an adduct with polyether.
Spesielt foretrukne addukter med polyethre, forst og fremst ved anvendelse av fremgangsmåten og komposisjonen for fremstilling av stSpeformer eller -kjerner ifolge den såkaldte cold-box metode, fordi særdeles gode utslagningsegenskaper derved erholdes, er addukter med alifatiske polyethre, som er polyaddukter av ethylenoxyd, propylenoxyd henholdsvis tetrahydrofuran til et alifatisk diamin eller til en alifatisk polyolforbindelse med 2-6 hydroxygrupper pr. molekyl, eller aromatiske polyethre med hvilken som helst av folgende generelle formler: hvor A betegner en enkel binding,"CH^eller Particularly preferred adducts with polyethers, first and foremost when using the method and composition for the production of basic forms or cores according to the so-called cold-box method, because particularly good knock-out properties are thereby obtained, are adducts with aliphatic polyethers, which are polyadducts of ethylene oxide, propylene oxide respectively tetrahydrofuran to an aliphatic diamine or to an aliphatic polyol compound with 2-6 hydroxy groups per molecule, or aromatic polyethers of any of the following general formulas: where A denotes a single bond,"CH^or
og y = 1 og R = H eller CH„ eller and y = 1 and R = H or CH„ or
y = 3 og R3= Hy = 3 and R3= H
samt n =1 - 5.and n =1 - 5.
Ifolge en foretrukken utforelsesform for oppfinnelsen velges en polyol med en pkg-verdi innen området 8 - 12. According to a preferred embodiment of the invention, a polyol with a pkg value within the range 8 - 12 is selected.
Ved fremgangsmåten ifolge oppfinnelsen anvendes den ovenfor omtalte polyolkomponent således i en mengde på 5 - 100 vekt%, beregnet på total polyhydroxykomponent. Det foretrukne område er avhengig av om de ovenfor omtalte lavmolekylære dioler (grunnbyggestenene) eller polyadduktene derav anvendes. Ved anvendelse av de lavmolekylære dioler er det foretrukne område 5-50 vekt%, spesielt 10 - 35 vekt%, mens det tilsvarende område for polyadduktene er 50 - 95 vekt%, særlig 65 - 90 vekt%. In the method according to the invention, the above-mentioned polyol component is thus used in an amount of 5-100% by weight, calculated on the total polyhydroxy component. The preferred range depends on whether the above-mentioned low molecular weight diols (the basic building blocks) or the polyadducts thereof are used. When using the low molecular weight diols, the preferred range is 5-50% by weight, especially 10-35% by weight, while the corresponding range for the polyadducts is 50-95% by weight, especially 65-90% by weight.
Den gjenstående andel av polyhydroxykomponenten velges blant de innen faget konvensjonelle polyhydroxyforbindeiser, fortrinnsvis blant polyetherpolyoler. Spesielt gode resultater ved formning av stopekjerner eller -former erholdes hvis den nevnte polyetherpolyol er en alifatisk eller aromatisk polyether valgt blant dem som ovenfor er omtalt i forbindelse med poly-etheradduktene. Eksempler på andre anvendbare polyhydroxyforbindelser er: The remaining proportion of the polyhydroxy component is selected from the polyhydroxy compounds conventional in the field, preferably from polyether polyols. Particularly good results when forming stopper cores or forms are obtained if the aforementioned polyether polyol is an aliphatic or aromatic polyether selected from among those mentioned above in connection with the polyether adducts. Examples of other useful polyhydroxy compounds are:
Hexoler på Hexoler on
sorbitol-sorbitol
basis: Atlas-sorbitolether G - 2410 frabase: Atlas sorbitol ether G - 2410 from
Atlas Chemiola Industries, Inc. Atlas Chemiola Industries, Inc.
basert på sorbitol og propylenoxyd. based on sorbitol and propylene oxide.
Ved utfdrelse av fremgangsmåten ifolge oppfinnelsen kan enhetlige forbindelser eller blandinger av slike komme til anvendelse som polyisocyanater. Polyisocyanatene skal ha minst When carrying out the method according to the invention, uniform compounds or mixtures thereof can be used as polyisocyanates. The polyisocyanates must have at least
to -NCO-grupper, men polyisocyanater med opp til seks =NC0-grupper kan komme til anvendelse. Polyisocyanatene kan ha alifatisk, cycloalifatisk, aralifatisk, aromatisk eller heterocyclisk mole-kylstruktur. Som eksempler på anvendbare polyisocyanater kan folgende nevnes: 2,4-toluendiisocyanat henh. 2,6-toluendiisocyanat two -NCO groups, but polyisocyanates with up to six =NC0 groups can be used. The polyisocyanates can have an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic molecular structure. The following can be mentioned as examples of usable polyisocyanates: 2,4-toluene diisocyanate acc. 2,6-toluene diisocyanate
eller deres isomere blandinger, or their isomeric mixtures,
difenylmethan-4,4-diisocyanat, diphenylmethane-4,4-diisocyanate,
difeny1-dimethyImethan-4,4-diisocya nat, trifenyl-4,4,4-triisocyanat, diphenyl-1-dimethylImethane-4,4-diisocyanate, triphenyl-4,4,4-triisocyanate,
fenylen-diisocyanat-1,4,2,2-6,6-tetramethy1-difenyl-methan-4, 4-diisocyanat, phenylene-diisocyanate-1,4,2,2-6,6-tetramethyl-1-diphenyl-methane-4, 4-diisocyanate,
difeny1-4,4-diisocyana t,dipheny1-4,4-diisocyana t,
difenyletner-4,4-diisocyanatdiphenylethene-4,4-diisocyanate
eller deres halogensubstituerte derivat, 2, 6-diisopropylen-1,3-diisocyanat, or their halogen-substituted derivative, 2,6-diisopropylene-1,3-diisocyanate,
m-xylen-diisocyanat,m-xylene diisocyanate,
p-xylen-diisocyanat,p-xylene diisocyanate,
tetramethy1-p-xylen-diisocyana t, tetramethy1-p-xylene-diisocyana t,
dimer-toluen-2,4-diisocyanat,dimer-toluene-2,4-diisocyanate,
hexan-1,6-diisocyanat,hexane-1,6-diisocyanate,
cyclohexan-1,4-diisocyanat, cyclohexane-1,4-diisocyanate,
1,2,3,4,5, 6-hexahydrodifenyImethan-4,4-diisocyanat, naf thalin-1,5-diisocyanat. 1,2,3,4,5, 6-hexahydrodiphenylmethane-4,4-diisocyanate, naphthalene-1,5-diisocyanate.
I stedet for disse ovennevnte polyisocyanater kan også et flertall addisjonsprodukter ined -NCO-endegrupper komme til anvendelse. Disse addisjonsprodukter tilvirkes på en slik måte at man omsetter en polyhydroxyforbindelse med polyisocyanat i slikt forhold at man erholder minst to NCO-grupper pr. molekyl i overskudd. I visse tilfeller kan overskudd av NCO-grupper oppgå til seks pr. molekyl. Instead of the above-mentioned polyisocyanates, a plurality of addition products with -NCO end groups can also be used. These addition products are produced in such a way that one reacts a polyhydroxy compound with polyisocyanate in such a ratio that one obtains at least two NCO groups per molecule in excess. In certain cases, excess NCO groups can amount to six per molecule.
Som ovenfor omtalt innebærer anvendelse av butendiol eller visse blandinger inneholdende butendiol som hovedkompo-nent at fremgangsmåten kan utfores helt opplSsningsmiddelfritt. As discussed above, the use of butenediol or certain mixtures containing butenediol as the main component means that the process can be carried out completely solvent-free.
Fremgangsmåten ifolge oppfinnelsen bygger på en poly-addisjonsreaks jon mellom NCO-gruppene i polyisocyanatene og ak-tivt hydrogen i polyhydroxyforbindelsene. For at herdningsfor-lopet skal forlope tilstrekkelig hurtig, anvendes katalysatorer slik som metaUorganiske forbindelser, metallsalter henholdsvis opplosninger av disse ellec tertiære aminer. Ved valg av egnet konsentrasjon av disse katalysatorer kan bearbeidningstid og herdetid varieres innen bestemte grenser. Katalysatoren er for trinnsvis gassformig slik som triethylamin, hvorved den blåses inn i det appliserte belegg, hvilket medforer at herdningen skjer ytterst hurtig. For at denne form for katalysering skal kunne anvendes, må det appliserte belegg ikke være altfor tykt. The method according to the invention is based on a polyaddition reaction between the NCO groups in the polyisocyanates and active hydrogen in the polyhydroxy compounds. In order for the curing process to proceed sufficiently quickly, catalysts such as metalorganic compounds, metal salts or solutions of these or tertiary amines are used. By choosing a suitable concentration of these catalysts, the processing time and curing time can be varied within certain limits. The catalyst is too gaseous in stages, such as triethylamine, whereby it is blown into the applied coating, which means that the curing takes place extremely quickly. In order for this form of catalysis to be used, the applied coating must not be too thick.
Da oppfinnelsen anvendes for fremstilling av stopekjerner og -former, innebærer dette at sand blandes med opp til 20 vekt%, beregnet på sandmengden, av komposisjonen ifolge oppfinnelsen. Hensiktsmessig ligger komposisjonens innhold imidlertid mellom 0,5 og 3,5 vekt% beregnet på sandmengden. As the invention is used for the production of stope cores and moulds, this means that sand is mixed with up to 20% by weight, calculated on the amount of sand, of the composition according to the invention. Appropriately, however, the composition's content is between 0.5 and 3.5% by weight calculated on the amount of sand.
For at det iiblge oppfinnelsen fremstillede belegg skal oppvise akseptable mekaniske egenskaper, er det nodvendig at forholdet polyisocyanat/polyhydroxyforbindelse er In order for the coating produced according to the invention to exhibit acceptable mechanical properties, it is necessary that the ratio polyisocyanate/polyhydroxy compound is
NCO NCO
Ori = 0,' 8 -. 3,' 0, ' fortrinnsvis 1,5 - 3,0.Ori = 0,' 8 -. 3,' 0, ' preferably 1.5 - 3.0.
Ved anvendelse av fremgangsmåten ifolge oppfinnelsen for fremstilling av formmasser skjer nevnte fremstilling ved blanding av torr stopesand, f.eks. kvarts- eller olevinsand, When using the method according to the invention for the production of molding compounds, said production takes place by mixing dry stoping sand, e.g. quartz or olivine sand,
med polyisocyanatforbindelsen. Polyisocyanatforbindelsen kan tilfores med eller uten opplosningsmiddel. Inert opplosning s-middel kan tilsettes for å holde blandingens viskositet på et akseptabelt nivå. Blandingen av sand og polyisocyanat skjer hensiktsmessig under.fuktfri atmosfære og ved en temperatur på 20 - 25°C. Efter noye blanding av sanden med polyisocyanatet tilsettes polyhydroxyforbindelsene. Formmasser tilvirket på denne måte har som regel en bearbeidelsestid på flere timer. Formmassen transporteres ved hjelp av trykkluft eller på meka-nisk vei til kjerneformen og komprimeres der. Direkte i til-slutning til dette eller samtidig, tilfores katalysatoren, hensiktsmessig i form av tertiært amin i gassform. Dette medforer en spontan herdning av formmassen, og kjernen kan derefter direkte fjernes fra formen. Disse kjerners holdfasthet er så hoy at en ekstra armering ikke er nodvendig. Stopekjernene - henholdsvis -formene inneholder eventuelt endel opplosningsmiddel. Dette kan fjernes ved luftning med trykkluft. I visse tilfeller kan luftningen med varm trykkluft være fordelaktig. Samtidig med opplosningsmiddelrester fjernes på denne måte eventuelt over- with the polyisocyanate compound. The polyisocyanate compound can be added with or without a solvent. Inert dissolving agent can be added to keep the viscosity of the mixture at an acceptable level. The mixing of sand and polyisocyanate takes place conveniently under a moisture-free atmosphere and at a temperature of 20 - 25°C. After careful mixing of the sand with the polyisocyanate, the polyhydroxy compounds are added. Molding compounds produced in this way usually have a processing time of several hours. The mold mass is transported using compressed air or by mechanical means to the core mold and compressed there. Directly in connection with this or at the same time, the catalyst is supplied, suitably in the form of tertiary amine in gaseous form. This leads to a spontaneous hardening of the molding compound, and the core can then be directly removed from the mold. The strength of these cores is so high that additional reinforcement is not necessary. The stopper cores - respectively - the molds contain any solvent. This can be removed by aerating with compressed air. In certain cases, aeration with warm compressed air can be beneficial. At the same time as solvent residues are removed in this way, any excess
skudd av tertiære aminer. De således tilvirkede kjerner er direkte anvendbare for metalistopning. En lagerbeholdning av kjerner er ikke nodvendig, hvilket betyr en betydelig okonomisk fordel. For spesielle metallstdpninger er det imidlertid nodvendig å overflatebehandle stopekjernene henholdsvis -formene med så-kaldt "blacknin gsmiddel1'. Dette er innen stdperibrans jen vel-kjente komposisjoner bestående av grafitt og/eller metalloxyder med organiske eller uorganiske bindemidler. shot of tertiary amines. The cores produced in this way are directly usable for metal filling. A stock of cores is not necessary, which means a significant economic advantage. For special metal supports, however, it is necessary to surface-treat the stop cores and molds with a so-called "blackening agent1". These are well-known compositions in the support industry consisting of graphite and/or metal oxides with organic or inorganic binders.
Tilvirkningen av formmassene ifolge oppfinnelsen kan imidlertid også skje på den måte at man fremstiller to separate sandblandinger. Den ene sandblanding inneholder polyhydroxyforbindelsen med tilsetning av katalysator i form av tertiært amin eller meta Uorganisk forbindelse, mens den annen blanding inneholder sand og polyisocyanatforbindelse. Umiddelbart for eller samtidig med applisering i formene blandes de to formmasser under hdy hastighet. Herved erholdes en umiddelbar utherdning av kjernene. Derefter kan kjernene fjernes fra formene, og en efterfolgende gasningsoperasjon bortfaller på den måte. However, the production of the molding compounds according to the invention can also take place in such a way that two separate sand mixtures are produced. One sand mixture contains the polyhydroxy compound with the addition of a catalyst in the form of a tertiary amine or meta Inorganic compound, while the other mixture contains sand and polyisocyanate compound. Immediately before or simultaneously with application in the molds, the two molding compounds are mixed at high speed. This results in an immediate hardening of the cores. The cores can then be removed from the moulds, and a subsequent fumigation operation is thus dispensed with.
Ved overflatebelegning av et ikke-partikkelformig materiale blandes polyisocyanat- og polyhydroxykomponenten samt eventuelt opplosningsmiddel hensiktsmessig for appliseringen, hvorefter blandingen appliseres på konvensjonell måte, slik som ved hjelp av sproytning, bestrykning eller lignende, og gassformig katalysator blåses gjennom det appliserte belegg. When surface coating a non-particulate material, the polyisocyanate and polyhydroxy component and any solvent are mixed appropriately for the application, after which the mixture is applied in a conventional manner, such as by means of spraying, painting or the like, and gaseous catalyst is blown through the applied coating.
Ved oppfinnelsen er det mulig å tilvirke stopekjerner og -former kontinuerlig i store serier. Rå-holdfastheten, dvs. holdfastheten direkte eller efter tilvirkningen, er så hoy at en risikofri håndtering av kjerner og former er mulig. Ved egnet sammensetning av komposisjonen kan ifolge oppfinnelsen erholdte stopekjerner eller -former anvendes for stopning av stopejern, stål og lettmetall. With the invention, it is possible to manufacture stopper cores and molds continuously in large series. The raw holding strength, i.e. the holding strength directly or after production, is so high that risk-free handling of cores and molds is possible. With a suitable composition of the composition, the stop cores or molds obtained according to the invention can be used for stopping stop iron, steel and light metal.
De ifolge oppfinnelsen tilvirkede formmasser utmerker seg ved god varmesjokkbestandighet og utmerket smuldring efter metallstdpningen. Helt nye muligheter for styring av formmas-senes egenskaper åpner seg dessuten ved inkorporering av umet-tethet, dvs. dobbelt- og trippelbindinger i komposisjonen ifolge oppfinnelsen. Således muliggjor eksempelvis oppfinnelsen en styring av den såkaldte glanskulldannelse, dvs. styring av det stopte materiales overflate, bare ved hjelp av de reaktanter som inngår i polyaddis jonsreaksj onenNoe ekstra tilsetnings-middel slik som tidligere har måttet anvendes ved stoperier for dette formål,, behover således ikke tilfores formmassen. Ifolge oppfinnelsen reguleres glanskulldannelsen i stedet ved hjelp av de dobbelt- og trippelbindinger som inngår i komposisjonen, hvorved okende andel trippelbindinger gir okende glanskuldannelse. The molding compounds produced according to the invention are distinguished by good thermal shock resistance and excellent crumbling after the metal filling. Completely new possibilities for controlling the properties of the molding compounds also open up by incorporating unsaturation, i.e. double and triple bonds in the composition according to the invention. Thus, for example, the invention makes it possible to control the so-called luster formation, i.e. control the surface of the stopped material, only with the help of the reactants that are part of the polyaddition reaction. thus the molding compound is not supplied. According to the invention, the gloss formation is regulated instead by means of the double and triple bonds that are included in the composition, whereby an increasing proportion of triple bonds results in an increasing gloss formation.
Oppfinnelsen belyses nærmere i de efterfolgende eksempler. The invention is explained in more detail in the following examples.
Eksempel1Example 1
Der ble tilvirket en polyether med molekylvekt på 5000. Av denne ble der tilberedt en blanding inneholdende 50 % av polyetheren, 25 % butendiol og 25 % cellosolveacetat. Denne blanding inneholdt 6 milliekvivalenter hydroxyl pr. gram. 5 g av blandingen ble blandet med 500 g sand av veldefinert kornstor-relse, hvorefter ble tilfort 7,65 g difenylmethandiisocyanat og blandet ca. 2 minutter. Den derved erholdte fremdeles lose sandblanding ble formet til formkropper som ble herdet ved gjen-nomblåsning av en katalysator i form av gassformig triethylamin i lopet av ca. 20 sekunder. De erholdte provekroppers initial-holdfasthet umiddelbart efter gasningens slutt var IO kp/cm 2, A polyether with a molecular weight of 5000 was produced. From this, a mixture containing 50% of the polyether, 25% butenediol and 25% cellosolve acetate was prepared. This mixture contained 6 milliequivalents of hydroxyl per gram. 5 g of the mixture was mixed with 500 g of sand of well-defined grain size, after which 7.65 g of diphenylmethane diisocyanate were added and mixed approx. 2 minutes. The resulting still loose sand mixture was formed into shaped bodies which were hardened by blowing through a catalyst in the form of gaseous triethylamine over the course of approx. 20 seconds. The initial holding strength of the sample bodies obtained immediately after the end of gassing was 10 kp/cm 2,
og deres sluttholdfasthet efter 1 time var 50 kp/cm<2>.and their final holding strength after 1 hour was 50 kp/cm<2>.
Eksempel 2Example 2
Av samme polyether som i eksempel 1 ble tilberedt en blanding inneholdende 80 % av polyetheren og 20 % butendiol. Blandingen inneholdt 5,08 milliekvivalenter hydroxyl pr. gram. 5 g av denne blanding ble blandet med 500 g sand, derefter til-satt 20,65 g difenylmethandiisocyanat, og sandblandingen ble formet til provekropper som ble herdet ved gjennomgasning med triethylamin ifolge eks.empel 1. Efter 20 sekunder var initial-holdfastheten 15 kp/cm 2, og efter en times lagring var slutt-holdfastheten 55 kp/cm 2. A mixture containing 80% of the polyether and 20% butenediol was prepared from the same polyether as in example 1. The mixture contained 5.08 milliequivalents of hydroxyl per gram. 5 g of this mixture was mixed with 500 g of sand, then 20.65 g of diphenylmethane diisocyanate was added, and the sand mixture was formed into test bodies which were hardened by gassing with triethylamine according to example 1. After 20 seconds, the initial holding strength was 15 kp /cm 2 , and after one hour of storage the final holding strength was 55 kp/cm 2 .
Claims (25)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7407504A SE398983B (en) | 1974-06-07 | 1974-06-07 | BY ADDITION OF A CATALYST CURABLE COATING AND BINDING COMPOSITION, SPECIFICALLY LEMPADED FOR COATING PARTICULAR MATERIALS AS SAND |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO752002L true NO752002L (en) | 1975-12-09 |
Family
ID=20321356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO752002A NO752002L (en) | 1974-06-07 | 1975-06-06 |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE829711A (en) |
| DE (1) | DE2523615A1 (en) |
| DK (1) | DK255475A (en) |
| FR (1) | FR2273608A1 (en) |
| IT (1) | IT1035852B (en) |
| NL (1) | NL7506736A (en) |
| NO (1) | NO752002L (en) |
| SE (1) | SE398983B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3405939A1 (en) * | 1984-02-18 | 1985-08-22 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING URETHANE-MODIFIED POLYISOCYANATE PREPARATIONS AND THEIR USE IN THE PRODUCTION OF POLYURETHANE PLASTICS OR POLYISOCYANURATE PLASTICS |
| DE4033221A1 (en) * | 1990-10-19 | 1992-04-23 | Bayer Ag | TWO-COMPONENT POLYURETHANE ADHESIVES |
-
1974
- 1974-06-07 SE SE7407504A patent/SE398983B/en unknown
-
1975
- 1975-05-27 IT IT49802/75A patent/IT1035852B/en active
- 1975-05-28 DE DE19752523615 patent/DE2523615A1/en active Pending
- 1975-05-30 BE BE156886A patent/BE829711A/en unknown
- 1975-06-06 DK DK255475A patent/DK255475A/en unknown
- 1975-06-06 NO NO752002A patent/NO752002L/no unknown
- 1975-06-06 NL NL7506736A patent/NL7506736A/en unknown
- 1975-06-06 FR FR7517832A patent/FR2273608A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1035852B (en) | 1979-10-20 |
| DK255475A (en) | 1975-12-08 |
| SE398983B (en) | 1978-01-30 |
| NL7506736A (en) | 1975-12-09 |
| SE7407504L (en) | 1975-12-08 |
| FR2273608A1 (en) | 1976-01-02 |
| DE2523615A1 (en) | 1975-12-18 |
| BE829711A (en) | 1975-09-15 |
| FR2273608B3 (en) | 1978-02-03 |
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