DK165184B - FORMAL SKIN-BINDING AGENT, METHOD OF MANUFACTURING THE AGENT, AND USE OF IT. - Google Patents
FORMAL SKIN-BINDING AGENT, METHOD OF MANUFACTURING THE AGENT, AND USE OF IT. Download PDFInfo
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- DK165184B DK165184B DK045184A DK45184A DK165184B DK 165184 B DK165184 B DK 165184B DK 045184 A DK045184 A DK 045184A DK 45184 A DK45184 A DK 45184A DK 165184 B DK165184 B DK 165184B
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- soluble halide
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
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- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Dry Formation Of Fiberboard And The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
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Description
iin
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Opfindelsen angår et formaldehydbindende middel til anvendelse i plader fremstillet ud fra lignocellulo-sematerialer under anvendelse af formaldehydbaserede klæbemidler, en fremgangsmåde til fremstilling af det for-5 maldehydbindende middel, samt anvendelse af det formaldehydbindende middel.This invention relates to a formaldehyde binding agent for use in sheets made from lignocellulose materials using formaldehyde based adhesives, a process for preparing the formaldehyde binding agent, and the use of the formaldehyde binding agent.
Plader, såsom partikelplader, spånplader og lignende, fremstilles ud fra lignocelluloseholdige materialer ved anvendelse af klæbemidler. De foretrukne klæbe-10 midler (eller lim) er baseret på formaldehyd, såsom urinstof-formaldehyd-, melamin-formaldehyd-, phenol-formaldehyd- og resorcinol-formaldehydharpikser eller blandinger deraf. Det er et velkendt faktum, at plader, der fremstilles ved anvendelse af disse klæbemidler, har en 15 formaldehydlugt, der både er skadelig og ubehagelig.Sheets, such as particle boards, particle boards and the like, are made from lignocellulosic materials using adhesives. The preferred adhesives (or adhesives) are based on formaldehyde such as urea-formaldehyde, melamine-formaldehyde, phenol-formaldehyde and resorcinol-formaldehyde resins or mixtures thereof. It is a well-known fact that sheets made using these adhesives have a formaldehyde odor that is both harmful and unpleasant.
Formaldehyd afgives både under sådanne pladers fremstilling og under deres opbevaring og endelige anvendelse.Formaldehyde is released both during the manufacture of such plates and during their storage and final use.
Der er blevet foreslået mange fremgangsmåder til at undgå afgivelsen af formaldehyd, men de er alle enten 20 ineffektive eller reducerer pladernes egenskaber eller kræver komplicerede udførelsesprocedurer. Nogle af disse procedurer involverer sprøjtning eller maling af de varme plader, der kommer ud af pressen med forskellige opløsninger, såsom opløsninger af urinstof og/eller ammoniak 25 eller af ammoniumsalte. Generelt er disse fremgangsmådetyper ikke ønskelige til industriel anvendelse, eftersom de kræver yderligere behandlingstrin og under alle omstændigheder ikke er særlig effektive.Many methods have been proposed to avoid the release of formaldehyde, but they are either either ineffective or reduce the properties of the plates or require complicated execution procedures. Some of these procedures involve spraying or painting the hot plates coming out of the press with various solutions, such as solutions of urea and / or ammonia 25 or of ammonium salts. In general, these types of processes are not desirable for industrial use, as they require additional processing steps and are in any case not very effective.
Andre metoder involverer anvendelsen af meget 30 komplicerede blandinger af et stort antal komponenter, hvoraf nogle er naturlige limstoffer. Disse produkter er ej heller meget effektive. Et handicap derved er det faktum, at naturprodukternes egenskaber ikke er konstante.Other methods involve the use of very complicated mixtures of a large number of components, some of which are natural adhesives. These products are also not very effective. A handicap thereby is the fact that the properties of the natural products are not constant.
35 En anden måde til at reducere indholdet af fri formaldehyd involverer anvendelsen af en vandig suspension af urinstofpellets overtrukket med en speciel voks.Another way to reduce the content of free formaldehyde involves the use of an aqueous suspension of the urea pellets coated with a special wax.
Også denne metode kræver en separat fødelinie, eftersomThis method also requires a separate feed line, since
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2 produktet ikke sættes til selve klæbemiddelformuleringen.2 the product is not added to the adhesive formulation itself.
Svensk fremlæggelsesskrift nr. 395.712 omhandler anvendelsen af molekylforbindelser som limtilsætningsmidler. Disse molekylforbindelser har som den ene kompo-5 nent en alifatisk forbindelse som indeholder en amidogrup-pe, eller visse andre nitrogenholdige grupper, og som den anden komponent et metalsalt eller en forbindelse, der indeholder en alkoholgruppe. Molekylforbindelserne skal indeholde de to komponenter i hele forhold. Med det form-10 aldehydbindende middel ifølge opfindelsen opnås herbver-for både bedre pladeegenskaber af de fremstillede plader og en større formindskelse af den frie formaldehyd.Swedish Patent Specification No. 395,712 discloses the use of molecular compounds as adhesive additives. These molecular compounds have as one component an aliphatic compound containing an amidogroup, or certain other nitrogen-containing groups, and, as the other component, a metal salt or compound containing an alcohol group. The molecular compounds must contain the two components in whole ratios. With the mold-aldehyde-binding agent according to the invention, hereby, both better plate properties of the manufactured sheets are obtained and a greater reduction of the free formaldehyde.
Ved nærværende opfindelse skal komponenterne (a) og (b) ikke være til stede i støkiometriske forhold.In the present invention, components (a) and (b) should not be present in stoichiometric conditions.
15 Desuden er det en fordel ved nærværende opfindelse, at alle komponenter kan tilsættes sammen og opløses i ét trin uden opvarmning.In addition, it is an advantage of the present invention that all components can be added together and dissolved in one step without heating.
Britisk patent nr. 1.099.088 omhandler i eksempel 3 en væske indeholdende vand, urinstof og sorbitol som på-20 føres træspåner. De behandlede spåner tørres og limes og sprøjtes med urinstof og/eller melaminformaldehydharpiks. Fremgangsmåden har den ulempe, at den kræver et separat trin, og dens hovedformål er at formindske pladernes holdbarhed. I dette skrift nævnes intet om tilsætning af 25 en vandig opløsning af urinstof og sorbitol til et klæbemiddel baseret på formaldehyd. Der nævnes heller ikke, at der opnås en formindskelse af mængden af fri formaldehyd eller en synergistisk effekt.In British Patent No. 1,099,088, Example 3 discloses a liquid containing water, urea and sorbitol applied to wood chips. The treated shavings are dried and glued and sprayed with urea and / or melamine formaldehyde resin. The method has the disadvantage of requiring a separate step and its main purpose is to reduce the durability of the plates. This publication does not mention the addition of an aqueous solution of urea and sorbitol to an adhesive based on formaldehyde. Nor is it mentioned that a reduction in the amount of free formaldehyde or a synergistic effect is achieved.
Britisk patent nr. 1.280.961 angår en fremgangs-30 måde til fremstilling af et modificeret prækondensat af en aminoplastharpiks, hvori der til harpiksen sættes 1-20 vægt%, baseret på harpiksens tørstof af et modificeringsmiddel, som omfatter et amid med den almene formelBritish Patent No. 1,280,961 relates to a process for preparing a modified precondensate of an aminoplastic resin wherein 1 to 20% by weight of the resin is added to the resin of a modifier comprising an amide of the general formula
O HO H
1 II I 21 II I 2
35 R -C-N-RR -C-N-R
hvori R1 betegner hydrogen eller en alkylgruppe med 1-4 2 carbonatomer, og R en alkylgruppe med 1-6 carbonatomer.wherein R 1 represents hydrogen or an alkyl group of 1-4 carbon atoms and R is an alkyl group of 1-6 carbon atoms.
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Fortrinsvis tilsættes også en polyhydroxyforbindelse som et supplerende modificerende middel. Ved direkte sammenligning mellem træspånplader indeholdende det modificerede prækondensat ifølge GB 1.280.961 og træspånplader in-5 deholdende det formaldehydbindende middel ifølge opfindelsen viser det sig, at træspånpladerne fremstillet ifølge den kendte teknik næsten ikke udviser nogen formindskelse af formaldehydmængden, og at de fysiske egenskaber af pladerne er væsentligt ringere end for pladerne inde-10 holdende det formaldehydbindende middel ifølge opfindelsen. Hensigten med opfindelsen er at angive et formaldehydbindende middel, der er bedre end de kendte, og som effektivt reducerer formaldehydlugten uden at reducere pladens egenskaber, uden at ændre klæbemiddel-15 formuleringernes reaktivitet og uden at kræve yderligere trin ved fremstilling af partikelplader, krydsfiner eller blokplader. Dette opnås som foran angivet med det formaldehydbindende middel ifølge opfindelsen.Preferably, a polyhydroxy compound is also added as a supplemental modifier. By direct comparison of wood chipboard containing the modified precondensate of GB 1,280,961 and wood chipboard containing the formaldehyde binding agent of the invention, it is found that the wood chipboards made by the prior art show almost no reduction in the amount of formaldehyde and that the physical properties of the the plates are substantially inferior to the plates containing the formaldehyde binding agent of the invention. The object of the invention is to provide a better-known formaldehyde binding agent which effectively reduces the formaldehyde odor without reducing the properties of the plate, without altering the reactivity of the adhesive formulations, and without requiring additional steps in the manufacture of particle boards, plywood or block boards. . This is achieved as indicated above with the formaldehyde binding agent of the invention.
Opfindelsen angiver et formaldehydbindende middel 2Q til anvendelse i plader fremstillet ud fra lignocellulo-sematerialer under anvendelse af formaldehydbaserede klæbemidler, kendetegnet ved, at det omfatter en vandig opløsning af.The invention discloses a formaldehyde binding agent 2Q for use in sheets made from lignocellulosic materials using formaldehyde based adhesives, characterized in that it comprises an aqueous solution of.
a) i det mindste en organisk hydroxyforbindelse, 25 valgt blandt sorbitol, monosaccharider med op til 6 carbonatomer og disaccharider med op til 12 car-bonatomer, og b) i det mindste et amid udvalgt blandt urinstof og thiourinstof, og eventuelt 30 c) en alifatisk monovalent alkohol, og/eller d) et vandopløseligt halogenidsalt, idet forholdet mellem den eller de organiske hydroxyfor-bindelser og amidet eller amiderne og eventuelt tilstedeværende vandopløseligt halogenidsalt er ikke-støkiometrisk, 35 og vægtforholdet mellem på den ene side komponent (a) og de eventuelle komponenter (c) og (d), og på den anden side komponent (b) andrager fra 10:100 til 400:100 og det formaldehydbindende middel indeholder fra 20 til 80 vægt% aktive bestanddele.a) at least one organic hydroxy compound selected from sorbitol, monosaccharides of up to 6 carbon atoms and disaccharides of up to 12 carbon atoms, and b) at least one amide selected from urea and thiourea, and optionally c) one aliphatic monovalent alcohol, and / or d) a water-soluble halide salt, the ratio of the organic hydroxy compound (s) to the amide or amides and any water-soluble halide salt present being non-stoichiometric, and the weight ratio of, on the one hand, component (a) and the optional components (c) and (d), and on the other hand component (b) is from 10: 100 to 400: 100 and the formaldehyde binding agent contains from 20 to 80% by weight of active ingredients.
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Selv om de individuelle komponenter ikke er opløselige i vand, kan de opløses i vand, såfremt en blanding deraf opvarmes til 70°C i vand.Although the individual components are not soluble in water, they can be dissolved in water if a mixture thereof is heated to 70 ° C in water.
De organiske hydroxyforbindelser (komponent (a)) 5 er fortrinsvis opløselige i vand eller i lavere monovalente alifatiske alkoholer.The organic hydroxy compounds (component (a)) 5 are preferably soluble in water or in lower monovalent aliphatic alcohols.
Specifikke eksempler på passende organiske hydroxyforbindelser er fruktose, mannose, sorbitol, dextrose, sucrose, maltose, lactose, dextrin og lignende.Specific examples of suitable organic hydroxy compounds are fructose, mannose, sorbitol, dextrose, sucrose, maltose, lactose, dextrin and the like.
10 De amider (komponent (b)), der anvendes i det omhandlede formaldehydbindemiddel er ligeledes fortrinsvis opløselige i vand eller i lavere monovalente alifatiske alkoholer.The amides (component (b)) used in the present formaldehyde binder are also preferably soluble in water or in lower monovalent aliphatic alcohols.
Passende eksempler på amider er urinstof og thio-15 urinstof.Suitable examples of amides are urea and thio-15 urea.
Om ønsket kan det omhandlede formaldehydbindemiddel for at forøge opløseligheden yderligere indeholde additiver (komponent (c)), der er lavere monovalente alifatiske alkoholer såsom methanol, ethanol, isopropa-20 nol og lignende.If desired, the present formaldehyde binder may further increase solubility contain additives (component (c)) which are lower monovalent aliphatic alcohols such as methanol, ethanol, isopropanol and the like.
Et billigere og mere effektivt formaldehydbindemiddel opnås, såfremt der tilsættes uorganiske forbindelser (komponent (d)), bestående af halogenidsalte, fortrinsvis halogenider af alkalimetaller eller jordalka-25 limetaller, såsom natriumchlorid, kaliumchlorid og calci-umchlorid.A cheaper and more effective formaldehyde binder is obtained if inorganic compounds (component (d)) are added, consisting of halide salts, preferably halides of alkali metals or alkaline earth metals such as sodium chloride, potassium chloride and calcium chloride.
Forholdet mellem organisk hydroxyforbindelse (komponent (a) og komponent (c) , hvis den er tilstede) uorganisk forbindelse (komponent (d), såfremt den er 30 tilstede) og amid (komponent (b)) er fortrinsvis 10:100 til 200Ϊ100 efter vægt. Det omhandlede formaldehydbindemiddel kan sættes til de sædvanlige limformuleringer i mængder varierende fra 1 til 10%, fortrinsvis 3 til 7% formaldehydbindemiddel fas t-35 stoffer på basis af vægten af den flydende harpiks indeholdende 65% vægt-% harpiks-faststoffer.The ratio of organic hydroxy compound (component (a) to component (c), if present) inorganic compound (component (d), if present) and amide (component (b)) is preferably 10: 100 to 200Ϊ100 after weight. The present formaldehyde binder may be added to the usual adhesive formulations in amounts ranging from 1 to 10%, preferably 3 to 7% formaldehyde binder phase t-35 based on the weight of the liquid resin containing 65% wt% resin solids.
Det omhandlede formaldehydbindemiddel kan indeholde 20 til 80 vægt-%, fortrinsvis 50 til 70 vægt-%The present formaldehyde binder may contain 20 to 80% by weight, preferably 50 to 70% by weight.
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5 aktive ingredienser (komponenterne (a) og (b) samt, såfremt de er til stede komponenterne (c) og/eller (d)). Vandindholdet i formaldehydbindemidlet afhænger af de aktive ingrediensers opløselighed og den mængde 5 vand, der kan tolereres i limformuleringerne.5 active ingredients (components (a) and (b) and, if present, components (c) and / or (d)). The water content of the formaldehyde binder depends on the solubility of the active ingredients and the amount of water that can be tolerated in the adhesive formulations.
Det omhandlede formaldehydbindemiddel kan fremstilles som angivet i krav 4 ved blot at sætte de aktive ingredienser og vand til en mikser og blande, indtil de aktive ingredienser er opløste. Dette kan gøres ved stuetempera-10 tur eller ved en hævet temperatur op til 70°C.The present formaldehyde binder can be prepared as claimed in claim 4 by simply adding the active ingredients and water to a mixer and mixing until the active ingredients are dissolved. This can be done at room temperature or at a raised temperature up to 70 ° C.
Det omhandlede formaldehydbindemiddel kan anvendes når der fremstilles plader ud fra lignocellulose-holdige materialer, ved anvendelse af klæbemidler baseret på formaldehyd, såsom urinstof-formaldehyd-, mela-15 min-formaldehyd-, phenol-formaldehyd- eller resorcinol-formaldehydharpikser eller blandinger deraf.The present formaldehyde binder may be used when making sheets from lignocellulose-containing materials, using adhesives based on formaldehyde such as urea-formaldehyde, mela-15-min-formaldehyde, phenol-formaldehyde or resorcinol-formaldehyde resins or mixtures thereof.
Ved anvendelse af formaldehydbindemidlet ifølge opfindelsen som angivet i krav 7 er det muligt at fremstille plader, der faktisk indeholder mindre end 10 mg fri formaldehyd pr.Using the formaldehyde binder according to the invention as set forth in claim 7, it is possible to prepare plates that actually contain less than 10 mg of free formaldehyde per day.
20 too g tør plade, bestemt efter F.E.S.Y.P. (Fédération Européenne des Syndicats des Fabricants de Panneaux de Particules) perforatormetoden nr. EN 120.20 g dry plate, determined by F.E.S.Y.P. (Federation of European Syndicates of Manufacturers of Panneaux of Particulars) perforator method No. EN 120.
Størrelsen af den fri formaldehydreduktion af-. hænger af mange faktorer og kan derfor variere bredt.The size of the free formaldehyde reduction of. depends on many factors and can therefore vary widely.
25 såfremt afgivelsen af fri formaldehyd er stor (større end 50 mg formaldehyd pr. 100 g tør plade), kan reduktionen være så stor som op til 60 til 85%. Såfremt afgivelsen af fri formaldehyd er relativ lille, dvs. 20 til 50 mg fri formaldehyd pr. 100 g tør plade, er den maksimale reduktion i almindelighed 50 til 60%. Størrelsen af den opnåede reduktion afhænger også af den anvendte mængde formaldehydbindemiddel: Jo mere form aldehydbindemiddel der anvendes, jo mindre er mængden * af fri formaldehyd.If the release of free formaldehyde is large (greater than 50 mg of formaldehyde per 100 g of dry plate), the reduction can be as large as up to 60 to 85%. If the release of free formaldehyde is relatively small, ie. 20 to 50 mg of free formaldehyde per day. 100 g of dry plate, the maximum reduction is generally 50 to 60%. The size of the reduction obtained also depends on the amount of formaldehyde binder used: The more form of aldehyde binder used, the smaller the amount * of free formaldehyde.
35 Når de aktive ingredienser i formaldehydbindemid let anvendes i kombination med hinanden, er reduktionen af fri formaldehyd overraskende meget større end summen af virkningen af de enkelte komponenter, og de har ikke35 When the active ingredients of formaldehyde binder are readily used in combination with each other, the reduction of free formaldehyde is surprisingly much greater than the sum of the effects of the individual components and they do not
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6 nogen skadelig virkning på limformuleringens aktivitet eller pladernes egenskaber.6 any detrimental effect on the activity of the adhesive formulation or the properties of the sheets.
De følgende eksempler belyser opfindelsen. Dele og procentdele er efter vægt.The following examples illustrate the invention. Parts and percentages are by weight.
55
Eksempel 1 I dette eksempel vises seks forskellige typer polyalkoholer, hvoraf prøve 1, 5 og 6 er ifølge opfindelsen, to forskellige typer amider, et additiv og en 10 variation i forholdet mellem alkohol og amid dækkende et område fra 57,5/100 til 385/100.Example 1 In this example, six different types of polyalcohols of which samples 1, 5 and 6 are according to the invention are shown, two different types of amides, an additive and an alcohol to amide ratio ranging from 57.5 / 100 to 385 / 100th
De forskellige typer anvendt formaldehydbindemid-del er som følger:The various types of formaldehyde binder used are as follows:
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De i de forskellige prøver anvendte limpræpara-ter er som følger:The adhesive preparations used in the various samples are as follows:
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Der fremstilles enkeltlagsplader i laboratoriet ved at sprøjte hvert af disse præparater på 25 kg træspåner. Pladerne presses i 10 og 9 og 8 sek/mm. Pladernes tykkelse er 17,3 mm. Pressens temperatur er 2 5 200 C, og trykket er 35 kg/cm . De fremstillede pla ders dimensioner er 40 x 56 cm.Single-layer sheets are made in the laboratory by spraying each of these preparations on 25 kg wood chips. The plates are pressed for 10 and 9 and 8 sec / mm. The thickness of the plates is 17.3 mm. The temperature of the press is 2500 C and the pressure is 35 kg / cm. The dimensions of the sheets produced are 40 x 56 cm.
De opnåede resultater er anført i den følgende tabel og er gennemsnitsværdier.The results obtained are listed in the following table and are average values.
<<
DK 165184BDK 165184B
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DK 165184BDK 165184B
1111
De ovennævnte resultater viser, at alle de anvendte prøver har værdier, der er ækvivalente med værdierne for kontrollen, og at formaldehydreduktionen ligger i størrelsesordenen 32 til 47 %.The above results show that all the samples used have values equivalent to the control values and that the formaldehyde reduction is in the range of 32 to 47%.
55
Eksempel 2Example 2
Der er udført sammenligningsforsøg for at vise, at formindskelsen af mængden af frit formaldehyd, såvel som pladernes egenskaber, bliver bedre, når der anvendes 10 det formaldehydbindende middel ifølge opfindelsen, end når der anvendes det i svensk fremlæggelsesskrift nr.Comparative experiments have been performed to show that the reduction of the amount of free formaldehyde, as well as the properties of the plates, is better when the formaldehyde binding agent of the invention is used than when it is used in Swedish disclosure no.
395.712 omhandlede additiv, specielt ved højere tilsætningsniveauer.395,712 discloses additives, especially at higher addition levels.
De anvendte præparater var som følger: 15 TABEL 1The preparations used were as follows: TABLE 1
Præparat 1 2 3· * S *Preparation 1 2 3 · * S *
Dextrose »0 20 Sorbitol - ‘210 ·Dextrose »0 20 Sorbitol - '210 ·
Sucrose - · 300 · · ·Sucrose - · 300 · · ·
Monoethylenglycol · · · 320Monoethylene glycol · · · 320
Diethylenglycol - " " “ 200Diethylene glycol - "" "200
Hexandiol - - “ * 275 25 Orea 400 330 330 310Hexanediol - - “* 275 25 Orea 400 330 330 310
Thiourea · · · · 370 355Thiourea · · · · 370 355
Vand 370 370 370 370 370 370 ialt 1000 1000 1000 1000 1000 1000 « tørstof 03 03 03 03 . 03 03 30Water 370 370 370 370 370 370 total 1000 1000 1000 1000 1000 1000 «dry matter 03 03 03 03. 03 03 30
Præparaterne 1, 2 og 3 er formaldehydbindende midler ifølge opfindelsen, medens præparaterne 4, 5 og 6 er valgt blandt de, der foreslås i det svenske skrift.Compositions 1, 2 and 3 are formaldehyde binding agents according to the invention, while compositions 4, 5 and 6 are selected from those proposed in Swedish writing.
35 Mængderne af præparaterne er anført i vægtdele og er valgt således, at det totale tørstofindhold for de enkelte præparater er ens. I præparaterne 4, 5 og 6 anvendes de i det svenske skrift foreslåede molforhold.The amounts of the compositions are given in parts by weight and are selected such that the total dry matter content of the individual compositions is the same. In compositions 4, 5 and 6, the molar ratios suggested in Swedish writing are used.
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Der blev fremstillet lim, som anført i nærværende beskrivelse, og geleringstiden blev bestemt for at sammenligne præparaterne nr. 1, 2 og 3 med præparaterne nr.Adhesives were prepared as set forth in this specification and the gelation time was determined to compare compositions # 1, 2 and 3 with compositions no.
4, 5 og 6. Sammensætningen af limen er anført i vægtdele 5 i Tabel 2.4, 5 and 6. The composition of the adhesive is listed in parts by weight 5 of Table 2.
TABEL 2TABLE 2
Limpræparat 0 1 2-3 4 5 6 10Glue preparation 0 1 2-3 4 5 6 10
Ureaformaldehyd- 3077 3077 3077 3077 3077 3077 3077 harpiks, 65% (molforhold F:U = 1,4:1) 15 Hærdner 400 500 500 500 500 500 500 (ammoniumchlorid, 15%'s opløsning) 20Urea Formaldehyde 3077 3077 3077 3077 3077 3077 3077 Resin, 65% (molar ratio F: U = 1.4: 1) Cures 400 500 500 500 500 500 500 (ammonium chloride, 15% solution) 20
Paraffin- 250 250 250 250 250 250 250 emulsion, 50%Paraffin 250 250 250 250 250 250 emulsion, 50%
Ammoniakvand 25° Baurré 5 ----- -Ammonia water 25 ° Baurré 5 ----- -
Præparat 1 fra Tabel. 1 - 460 - - - - -Preparation 1 from Table. 1 - 460 - - - - - -
Præparat 2 fra Tabel 1 - " 460 - . - 25 Præparat 3 fra Tabel 1 - - - 460 - - -Preparation 2 from Table 1 - "460 - - - 25 Preparation 3 from Table 1 - - - 460 - - -
Præparat 4 fra Tabel 1 - - - - 460 - -Preparation 4 from Table 1 - - - - 460 - -
Præparat 5 fra Tabel 1 - - - 460Preparation 5 from Table 1 - - - 460
Præparat 6 fra Tabel 1 - - - 460 30 Vand 268 ------Preparation 6 from Table 1 - - - 460 30 Water 268 ------
Ialt 4000 4287 4287 4287 4287 4287 4287Total 4000 4287 4287 4287 4287 4287 4287
Geleringstid (s) 57 59 57 58 61 60 62Gelling time (s) 57 59 57 58 61 60 62
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Enkeltlagsplader blev fremstillet i laboratoriet ved at sprøjte hver af disse limpræparater på 25 kg træspåner. Pladerne blev presset i 10, 9 og 8 s/mm. Pladernes tykkelse var 17,3 mm. Pressens temperatur var 200°CSingle-layer sheets were made in the laboratory by spraying each of these adhesives on 25 kg wood chips. The plates were pressed at 10, 9 and 8 s / mm. The thickness of the plates was 17.3 mm. The temperature of the press was 200 ° C
2 5 og trykket 35 kg/cm . Pladernes dimensioner var 40 x 56 cm. De opnåede resultater fremgår af Tabel 3, som angiver gennemsnitsværdier.: TABEL· 3 102 and the pressure 35 kg / cm. The dimensions of the plates were 40 x 56 cm. The results obtained are shown in Table 3, which indicates average values: TABLE · 3 10
Limpræparat 01 23456Glue preparation 01 23456
Densitet (kg/ra3) 690 669 690 688 685 687 686 ' Bøjestyrke (N/mm2) 22,3 25,2 24,9 24,1 20,9 21,5 20,5 15 Trækstyrke (N/mm2 ) 0,75 0,81 0,85 0,82 0,65 0,63 0,61Density (kg / ra3) 690 669 690 688 685 687 686 'Bending strength (N / mm2) 22.3 25.2 24.9 24.1 20.9 21.5 20.5 15 Tensile strength (N / mm2) 0, 75 0.81 0.85 0.82 0.65 0.63 0.61
Tykkelsesforøgelse 69 6* M 6,5 7,1 7,2 7,1 ved 2 timers kvældning (%) 7Thickness Increase 69 6 * M 6.5 7.1 7.2 7.1 at 2 hours of swelling (%) 7
Tykkelsesforøgelse ved 19,3 18,8 18,6 18,9 20,2 20,5 20,9 24 timers kvældning (%)Thickness increase at 19.3 18.8 18.6 18.9 20.2 20.5 20.9 24 hour swelling (%)
Fri formaldehyd 42 9,3 8,4 7,1 22,3 20,2 21 20 tør plade)Free formaldehyde 42 9.3 8.4 7.1 22.3 20.2 21 20 dry plate)
Formindskelse af · 78 80 83 47 52 50 formaldehydmængde (%) 25 De i Tabel 3 anførte resultater viser, at præpara terne, som i Tabel 1 er betegnet 1 til 3, giver plader med bedre mekanisk styrke og vandbestandighed end kontrolprøven (limpræparat 0), selv om formindskelsen af formaldehydmængden er ekstrem stor. I modsætning hertil 30 giver præparaterne 4 til 6 i Tabel 1 plader, som er ringere end kontrolprøven på trods af, at formindskelsen af formaldehydmængden er meget mindre, end hvad der opnås med præparaterne 1 til 3.Reduction of · 78 80 83 47 52 50 Amount of formaldehyde (%) 25 The results shown in Table 3 show that the preparations, denoted in Table 1, 1 to 3, give plates with better mechanical strength and water resistance than the control sample (adhesive composition 0) , although the reduction in the amount of formaldehyde is extremely large. In contrast, compositions 4 to 6 of Table 1 yield plates that are inferior to the control sample, despite the reduction in the amount of formaldehyde being much smaller than that obtained with compositions 1 to 3.
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Eksempel 3Example 3
Der er udført sammenligningsforsøg for at vise, at opløsningen ifølge eksempel 3 i britisk patent nr.Comparative experiments have been carried out to show that the solution of Example 3 of British Patent No. 5,197,107 is a non-standard solution.
1 099 088 (prøve 2) er underlegen i forhold til det for-5 maldehydbindende middel i Eksempel 1-5 i nærværende ansøgning (prøve 1):1,099,088 (sample 2) is inferior to the formaldehyde binding agent of Examples 1-5 of the present application (sample 1):
De anvendte prøver var som følger: J_Væqtdele 2_Vægtdele 10 Sorbitol 140 Sorbitol (1:1 i vand) 10The samples used were as follows: J_Weight Parts 2_Weight Parts 10 Sorbitol 140 Sorbitol (1: 1 in water) 10
Methanol 140 Natriumfluorid 5Methanol 140 Sodium Fluoride 5
Urea 350 Urea 125Urea 350 Urea 125
Vand 370 Ammoniumdihydrogen- 15 phosphat -160Water 370 Ammonium dihydrogen phosphate -160
Vand 700Water 700
Ialt 1000 Ialt 1000 20Total 1000 Total 1000 20
Limpræparater blev fremstillet som i Eksempel 1 og geleringstiden og anvendelsestiden blev målt for at sammenligne præparaterne 1, 2 og 3 med kontrolpræparatet 0. Præparaterne såvel som resultaterne er anført i 25 den følgende tabel:Adhesive preparations were prepared as in Example 1 and the gelation time and use time were measured to compare preparations 1, 2 and 3 with the control preparation 0. The preparations as well as the results are given in the following table:
DK 165184BDK 165184B
15 Vægtdele_O (g) 1 (g) 2 (g) 5 (g)Parts by weight_O (g) 1 (g) 2 (g) 5 (g)
Urea-formaldehydharpiks 65% 3077 3077 3077 3077Urea-formaldehyde resin 65% 3077 3077 3077 3077
Molforhold F:U 1,25) Hærdner (Ammonium- ^00 500 500 — 5 chlorid 15%'s opløsning) Hærdner (85%'s myresyre) — — — 23.5Molecular ratio F: U 1.25) Cures (Ammonium - 500 500 - 5 chloride 15% solution) Cures (85% formic acid) - - - 23.5
Paraffinemulsion, 50% 250 250 250 250Paraffin emulsion, 50% 250 250 250 250
Ammoniakvand, 25° Baumé 5 _ —Ammonia water, 25 ° Baumé 5 _ -
Prøve 1 — 307 — — 10 Prøve 2 — — 307 307Sample 1 - 307 - - 10 Sample 2 - - 307 307
Vand__ 268_—_~_*76,5Water__ 268 _ — _ ~ _ * 76.5
Ialt 4000 4134 4134 4134Total 4000 4134 4134 4134
Geleringstid (i sekunder) 68 64 49 44 15 pH 7,88 7,13 5,7 3,75Gelling time (in seconds) 68 64 49 44 pH 7.88 7.13 5.7 3.75
Anvendelsestid (40°C) 4t 45a 4t15a 2t 20 ain .Application time (40 ° C) 4h 45a 4t15a 2h 20 ain.
Enkeltlagsplader blev fremstillet i laboratoriet 20 ved at sprøjte hvert af disse præparater på 25 kg træspåner. Pladerne blev presset i 10, 9 og 8 s/mm. Pladernes tykkelse var 17,3 mm. Pressens temperatur var 200°C, og trykket var 35 kg/m . Dimensionen af de fremstillede plader var 40 x 56 cm. De opnåede resultater er anført i ne-25 denstående tabel og er gennemsnitsværdier:Single-layer plates were made in the laboratory 20 by spraying each of these preparations on 25 kg wood chips. The plates were pressed at 10, 9 and 8 s / mm. The thickness of the plates was 17.3 mm. The temperature of the press was 200 ° C and the pressure was 35 kg / m. The dimension of the sheets produced was 40 x 56 cm. The results obtained are listed in the table below and are average values:
Præparat o 12. 3Preparation o 12. 3
Densitet (kg/m3) 690,00 687,00 689,00 650,00 30 Bøjestyrke (N/mm2) 19,70 19,40 14,80 10,50Density (kg / m3) 690.00 687.00 689.00 650.00 30 Bending strength (N / mm2) 19.70 19.40 14.80 10.50
Trækstyrke (N/mm2) 0,72 0,72 0,51 0,25Tensile strength (N / mm2) 0.72 0.72 0.51 0.25
Tykkelses forøgel se ved , 2 timers kvældning (%) 7>40 7»20 8>30 15'30Thickness increase see, 2 hours of swelling (%) 7> 40 7 »20 8> 30 15'30
Tykkelsesforøgelse ved 19,70 19,80 25,40 40,80 24 timers kvældning (%) •Fri formaldehyd * 18/20 10,10 15,30 16,10 35 (mg/J00 g tør plade)Thickness increase at 19.70 19.80 25.40 40.80 24 hour swelling (%) • Free formaldehyde * 18/20 10.10 15.30 16.10 35 (mg / J00 g dry plate)
Formindskelse af — 45,()0 15,90 11,50 formaldehyd (%)Decrease of - 45, () 0 15.90 11.50 formaldehyde (%)
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Det fremgår, at pladerne, som blev fremstillet med opløsningen ifølge Eksempel 3 fra britisk patent 1 099 088 (præparaterne 2 og 3 indeholdende prøve 2), har meget ringe egenskaber sammenlignet med plader frem-5 stillet med det formaldehydbindende middel ifølge opfindelsen (præparat 1 indeholdende prøve 1) på trods af, at formindskelsen af formaldehydmængden er betydeligt større i præparat 1 end i præparaterne 2 og 3.It can be seen that the plates prepared with the solution of Example 3 from British Patent 1,099,088 (Preparations 2 and 3 containing Sample 2) have very poor properties as compared to plates made with the formaldehyde binding agent of the invention (Preparation 1 containing sample 1) despite the fact that the decrease in the amount of formaldehyde is considerably greater in preparation 1 than in preparations 2 and 3.
10 Eksempel 4Example 4
Der er foretaget sammenligningsforsøg for at vise, at anvendelse af en vandig opløsning eller dispersion af et modificeringsmiddel ifølge britisk patent nr. 1 280 961 giver dårligere resultater, end hvad der opnås med det 15 formaldehydbindende middel ifølge opfindelsen:Comparative experiments have been made to show that using an aqueous solution or dispersion of a modifier of British Patent No. 1,280,961 gives worse results than that obtained with the formaldehyde binding agent of the invention:
To prøver ifølge opfindelsen (prøver 1 og 2) og to prøver ifølge britisk patent nr. 1 280 961 (prøver 3 og 4) blev fremstillet. Vandindholdet i prøverne 1 og 3 er lavere end i prøverne 2 og 4. Prøverne var som følger: 20Two samples according to the invention (samples 1 and 2) and two samples according to British Patent No. 1 280 961 (samples 3 and 4) were prepared. The water content of samples 1 and 3 is lower than in samples 2 and 4. The samples were as follows: 20
Prøver_-_1_2_3_4 vægtdeleSamples _-_ 1_2_3_4 parts by weight
Sucrose 250 - 250 -Sucrose 250 - 250 -
Ethylenglycol 250 230 250 230 N-methyl formamid - - 250 350 25 Urea 250 350Ethylene glycol 250 230 250 230 N-methyl formamide - - 250 350 Urea 250 350
Vand 250 420 250 420 *Water 250 420 250 420 *
Ialt 1000 1000 1000 1000 pH 9,3 9,4 6,0' 5,9 30Total 1000 1000 1000 1000 pH 9.3 9.4 6.0 '5.9 30
Der blev fremstillet limpræparater med nedenstående sammensætning. Geleringstid, pH og anvendelsestid blev målt for at sammenligne prøverne 1 til 4 med kontrolpræparatet 0.Adhesives of the following composition were prepared. Gelling time, pH and application time were measured to compare samples 1 to 4 with control preparation 0.
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Præparat 0(g)_Hl) 2(g) 3(g)_4(g)Preparation 0 (g) _H1) 2 (g) 3 (g) _4 (g)
Urea-formaldehyd 65% (molforhold F:U.Urea-formaldehyde 65% (molar ratio F: U.
1/25:1) 3077 3077 3077 3077 3077 Hærdner (Ammon i um-5 chlorid, 15%'s opløsning) 400 500 500 500 5001/25: 1) 3077 3077 3077 3077 3077 Cures (Ammonium in 5 chloride, 15% solution) 400 500 500 500 500
Paraffinemulsion, 50% 250 250 250 250 250 , Ammon i akvand, 25° Baumé 5 - - - -Paraffin emulsion, 50% 250 250 250 250 250, Ammon in water, 25 ° Baumé 5 - - - -
Prøve 1 * 307 - · -Sample 1 * 307 - · -
Prøve 2 " ** 707 - - 15 Prøve 3 ” ” “ 307 “Sample 2 "** 707 - - 15 Sample 3" "" 307 "
Prøve 4 · 307Sample 4 · 307
Vand 36· - - - -Water 36 · - - - -
Ialt 4000 4134 4134 4134 4134 20......... ........... ....................... .........................................Total 4000 4134 4134 4134 4134 20 ......... .......................... .........................................
Geleringstid (sek.) 4· 63 64 62 60 pH 7,8 7,14 7^13 7f19 7,10Gelation time (sec) 4 · 63 64 62 60 pH 7.8 7.14 7 ^ 13 7f19 7.10
Anvendelsestid (40°C)4t45« 4t20e .4t|5« 3t 15· 3.t05· 25 Enkeltlagsplader blev fremstillet i laboratoriet ved at sprøjte hvert af disse præparater på 25 kg træspåner. Pladerne blev presset ved 10, 9 og 8 sek/mm. Pladernes tykkelse var 17,3 mm. Pressens temperatur var 200°C, og trykket var 35 kg/cm2. Dimensionerne af de 30 fremstillede plader var 40 x 56 cm.Application time (40 ° C) 4t45 «4t20e .4t | 5« 3t 15 · 3.t05 · 25 Single layer sheets were made in the laboratory by spraying each of these preparations on 25 kg wood chips. The plates were pressed at 10, 9 and 8 sec / mm. The thickness of the plates was 17.3 mm. The temperature of the press was 200 ° C and the pressure was 35 kg / cm 2. The dimensions of the 30 sheets made were 40 x 56 cm.
De opnåede resultater fremgår af nedenstående tabel, som angiver gennemsnitsværdier:The results obtained are shown in the table below, which indicates average values:
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Præparat 01234Preparation 01234
Densitet (kg/mm2) 691 681 685 683 681 Bøjestyrke (N/mm2) 19,80 19,95 19,30 17,60 16,70Density (kg / mm2) 691 681 685 683 681 Bending strength (N / mm2) 19.80 19.95 19.30 17.60 16.70
Trækstyrke (N/mm2) 0,71 0,75 0,72 0,60 0,58 5 Tykkelsesforøgelse ved 2 timers kvæld- ning (%) 7,80 7,40 7,20 8,70 9,30Tensile strength (N / mm2) 0.71 0.75 0.72 0.60 0.58 5 Thickness increase at 2 hour swelling (%) 7.80 7.40 7.20 8.70 9.30
Tykkelsesforøgelse ved 24 timers kvæld- ning (%) 20,30 20,10 19,60 21,90 22,90 ,n Fri formaldehyd lu (mg/1OOg tør plade) 18,50 10,00 9,50 16,90 17,30Thickness increase at 24 hours swelling (%) 20.30 20.10 19.60 21.90 22.90, n Free formaldehyde lu (mg / 100g dry plate) 18.50 10.00 9.50 16.90 17 , 30
Formindskelse af formaldehydmængde (%) - 45,95 48,65 8,65 6,95 15 Det bemærkes, at selv om der praktisk taget ikke sker nogen reduktion af fri formaldehyd i pladerne, som fremstilles med prøverne 3 og 4 ifølge britisk patent nr. 1 280 961, er egenskaberne af disse plader væsentligt ringere, end hvad der opnås med prøverne 1 og 2, 20 fremstillet ifølge opfindelsen.Decrease in Formaldehyde Amount (%) - 45.95 48.65 8.65 6.95 15 It is noted that although there is practically no reduction of free formaldehyde in the plates made with samples 3 and 4 of British Patent No. 1 280 961, the properties of these plates are substantially inferior to those obtained with samples 1 and 2, 20 made according to the invention.
Claims (7)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8303350 | 1983-02-07 | ||
GB838303350A GB8303350D0 (en) | 1983-02-07 | 1983-02-07 | Formaldehyde binder |
GB838320128A GB8320128D0 (en) | 1983-02-07 | 1983-07-26 | Formaldehyde binder |
GB8320128 | 1983-07-26 |
Publications (4)
Publication Number | Publication Date |
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DK45184D0 DK45184D0 (en) | 1984-02-01 |
DK45184A DK45184A (en) | 1984-08-08 |
DK165184B true DK165184B (en) | 1992-10-19 |
DK165184C DK165184C (en) | 1993-03-01 |
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DK045184A DK165184C (en) | 1983-02-07 | 1984-02-01 | FORMAL SKIN-BINDING AGENT, METHOD OF MANUFACTURING THE AGENT, AND USE OF IT |
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JP (1) | JPH0613686B2 (en) |
AR (1) | AR242246A1 (en) |
AT (1) | AT385513B (en) |
AU (1) | AU570028B2 (en) |
CA (1) | CA1225630A (en) |
CH (1) | CH658218A5 (en) |
DD (1) | DD232018A5 (en) |
DE (1) | DE3403136C2 (en) |
DK (1) | DK165184C (en) |
ES (1) | ES8505398A1 (en) |
FI (1) | FI840448A (en) |
FR (1) | FR2540506B1 (en) |
GB (1) | GB2136008B (en) |
GR (1) | GR79713B (en) |
HU (1) | HU197591B (en) |
IL (1) | IL70844A (en) |
IT (1) | IT1177542B (en) |
LU (1) | LU85195A1 (en) |
MX (1) | MX168053B (en) |
MY (1) | MY8700455A (en) |
NL (1) | NL8400322A (en) |
NO (1) | NO169848C (en) |
NZ (1) | NZ206859A (en) |
PL (1) | PL144282B1 (en) |
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Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
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DE3439929A1 (en) * | 1984-11-02 | 1986-05-07 | Basf Ag, 6700 Ludwigshafen | HARDENER FOR AMINOPLAST RESIN, ITS USE IN THE LAMINATION AND FUNCTIONING OF WOODEN MATERIALS AND METHOD FOR LAMINATING AND FUNCTIONING WOODEN MATERIAL |
GB2170208B (en) * | 1985-01-29 | 1988-06-22 | Enigma Nv | A formaldehyde binder |
NZ220437A (en) * | 1986-06-06 | 1989-06-28 | Enigma Nv | Aldehyde/sugar/lignosulphonate mixture as a substitute for amino and phenolic resins in bonding agents |
GB2191207B (en) * | 1986-06-06 | 1989-12-13 | Enigma Nv | Substitute for amino and phenolic resins |
DE3815204A1 (en) * | 1988-05-04 | 1989-11-16 | Gruber & Weber Gmbh Co Kg | PROCESS FOR PRODUCING COMPOSITE MATERIALS WITH REDUCED FORMALDEHYDE EMISSION |
DE3943488C2 (en) * | 1989-09-14 | 1999-05-27 | Dieter Ekkehard Dip Autenrieth | Process for reducing or eliminating free formaldehyde with carbamates, which are generated on the substrate in the critical phase when formaldehyde is released |
DE10021849A1 (en) | 2000-05-05 | 2001-11-08 | Solutia Germany Gmbh & Co Kg | Aqueous aminoplast composition, used for impregnating paper or cardboard for use as finish foil or edge for furniture, contains specified formaldehyde-binding additive and optionally acrylate resin dispersion |
SG90767A1 (en) * | 2001-01-03 | 2002-08-20 | Yang Kuo Chen | Method of making non-polluting products |
US6720392B2 (en) | 2001-05-17 | 2004-04-13 | Solutia Germany Gmbh & Co. Kg | Aqueous amino resin blends |
GB201517867D0 (en) | 2015-10-09 | 2015-11-25 | Knauf Insulation Ltd | Wood particle boards |
EP3768478B1 (en) | 2018-03-23 | 2022-04-27 | Foresa Technologies S.L.U. | Hydrophobing and formaldehyde scavenging compositions comprising wax emulsions and resorcinol and their use for increasing the hydrophobicity of wood composite boards and fibreglass or rock wool insulations |
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DE1054232B (en) * | 1956-03-29 | 1959-04-02 | Basf Ag | Process for the production of foams |
AT261190B (en) * | 1965-03-25 | 1968-04-10 | Wilhelmi Holzwerk | Process for the treatment of wood chips with binding and impregnating agents |
GB1254786A (en) * | 1968-03-12 | 1971-11-24 | Beck Koller And Co England Ltd | Phenol modified urea-formaldehyde resins |
CH1426068A4 (en) * | 1968-09-24 | 1972-08-15 | ||
GB1280961A (en) * | 1969-10-29 | 1972-07-12 | Goldschmidt Ag Th | Aminoplast resin precondensates and a method of producing them |
GB1427927A (en) * | 1970-05-30 | 1976-03-10 | British Industrial Plastics | Hardener for urea-formaldehyde resin foams |
CH540947A (en) * | 1970-09-07 | 1973-08-31 | Ciba Geigy Ag | Process for the production of plasticized melamine-formaldehyde condensation products and their use |
FR2128472B1 (en) * | 1971-03-04 | 1976-03-26 | Basf Ag | |
BE789804A (en) * | 1971-10-07 | 1973-04-06 | Cassella Farbwerke Mainkur Ag | AMINOPLASTE INTENDED FOR COATING WOOD-BASED MATERIALS AND LAMINATES AS WELL AS A PROCESS FOR THE PREPARATION OF THIS AMINOPLAST |
DE2206696C3 (en) * | 1972-02-12 | 1978-05-24 | Eib, Wilhelm, 7417 Pfullingen | Use of molecular compounds as additives to adhesives based on formaldehyde-releasing condensates |
BE795631A (en) * | 1972-02-19 | 1973-08-20 | Basf Ag | AMINOPLAST BINDERS FOR WOOD-BASED MATERIALS |
FR2309575A1 (en) * | 1975-04-30 | 1976-11-26 | Saint Gobain | AQUEOUS SOLUTIONS OF ETHERIFIED MELAMINE-FORMALDEHYDE RESINS WITH A LONG SHELF LIFE AND LOW FREE FORMALDEHYDE CONTENT |
DE2324046A1 (en) * | 1973-05-12 | 1974-11-28 | Basf Ag | Fire-resistant, temp-variation resistant chipboard prepn. - by adding alcohol to glue or wood chips |
US3983084A (en) * | 1974-10-18 | 1976-09-28 | Krause Milling Company | Art of manufacturing compression molded particle board with nitrogenous modified amylaceous binder |
DE2740207B1 (en) * | 1977-09-07 | 1978-11-09 | Basf Ag | Process for the production of wood-based materials with reduced subsequent release of formaldehyde |
US4139507A (en) * | 1978-01-12 | 1979-02-13 | Allied Chemical Corporation | One-component binder for fiberboard |
US4192923A (en) * | 1978-10-27 | 1980-03-11 | Allied Chemical Corporation | Amino resin foam, one-phase solution foam precursor and method of producing foam |
DE3222195A1 (en) * | 1982-06-12 | 1983-12-15 | Basf Ag, 6700 Ludwigshafen | METHOD FOR THE PRODUCTION OF CHIPWOOD MATERIALS WITH REDUCED FORMALDEHYDEMISSION |
-
1984
- 1984-01-17 GB GB08401225A patent/GB2136008B/en not_active Expired
- 1984-01-17 NZ NZ206859A patent/NZ206859A/en unknown
- 1984-01-26 AU AU23810/84A patent/AU570028B2/en not_active Ceased
- 1984-01-30 DE DE3403136A patent/DE3403136C2/en not_active Expired - Fee Related
- 1984-01-30 AT AT0029784A patent/AT385513B/en not_active IP Right Cessation
- 1984-01-31 GR GR73668A patent/GR79713B/el unknown
- 1984-02-01 SE SE8400509A patent/SE463717B/en unknown
- 1984-02-01 IL IL70844A patent/IL70844A/en not_active IP Right Cessation
- 1984-02-01 CH CH471/84A patent/CH658218A5/en not_active IP Right Cessation
- 1984-02-01 DK DK045184A patent/DK165184C/en active
- 1984-02-02 NO NO840403A patent/NO169848C/en unknown
- 1984-02-02 NL NL8400322A patent/NL8400322A/en not_active Application Discontinuation
- 1984-02-03 RO RO84113506A patent/RO88986A/en unknown
- 1984-02-03 IT IT47647/84A patent/IT1177542B/en active
- 1984-02-03 FI FI840448A patent/FI840448A/en not_active Application Discontinuation
- 1984-02-06 ES ES529473A patent/ES8505398A1/en not_active Expired
- 1984-02-06 DD DD84259887A patent/DD232018A5/en unknown
- 1984-02-06 JP JP59020671A patent/JPH0613686B2/en not_active Expired - Lifetime
- 1984-02-06 LU LU85195A patent/LU85195A1/en unknown
- 1984-02-06 FR FR8401767A patent/FR2540506B1/en not_active Expired
- 1984-02-06 CA CA000446837A patent/CA1225630A/en not_active Expired
- 1984-02-06 HU HU84470A patent/HU197591B/en not_active IP Right Cessation
- 1984-02-06 PT PT78066A patent/PT78066B/en not_active IP Right Cessation
- 1984-02-07 AR AR84295655A patent/AR242246A1/en active
- 1984-02-07 MX MX200262A patent/MX168053B/en unknown
- 1984-02-07 PL PL1984246098A patent/PL144282B1/en unknown
-
1986
- 1986-05-20 YU YU827/86A patent/YU44138B/en unknown
-
1987
- 1987-12-30 MY MY455/87A patent/MY8700455A/en unknown
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