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WO2001094436A2 - Procedes pour produire des mousses a partir de condensats de melamine/formaldehyde - Google Patents

Procedes pour produire des mousses a partir de condensats de melamine/formaldehyde Download PDF

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Publication number
WO2001094436A2
WO2001094436A2 PCT/EP2001/006399 EP0106399W WO0194436A2 WO 2001094436 A2 WO2001094436 A2 WO 2001094436A2 EP 0106399 W EP0106399 W EP 0106399W WO 0194436 A2 WO0194436 A2 WO 0194436A2
Authority
WO
WIPO (PCT)
Prior art keywords
melamine
formaldehyde
ppm
foam
foams
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2001/006399
Other languages
German (de)
English (en)
Other versions
WO2001094436A3 (fr
Inventor
Horst Baumgartl
Bernd Gross
Isidor De Grave
Wulf Trauzettel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to AU2001285731A priority Critical patent/AU2001285731A1/en
Publication of WO2001094436A2 publication Critical patent/WO2001094436A2/fr
Publication of WO2001094436A3 publication Critical patent/WO2001094436A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
    • C08G12/32—Melamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2205/00—Foams characterised by their properties
    • C08J2205/04—Foams characterised by their properties characterised by the foam pores
    • C08J2205/05—Open cells, i.e. more than 50% of the pores are open
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2205/00—Foams characterised by their properties
    • C08J2205/06—Flexible foams
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
    • C08J2361/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08J2361/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08J2361/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine

Definitions

  • the invention relates to a process for producing open-cell elastic foams based on a melamine / formaldehyde condensation product, in which an aqueous solution or dispersion which contains a melamine / formaldehyde precondensate, an emulsifier, a blowing agent and a hardener and possibly contains conventional additives, foamed by heating and the foam cures by crosslinking the precondensate.
  • European patents 17 621 and 17 672 describe open-cell elastic foams based on melamine / formaldehyde condensation products and processes for their production.
  • a highly concentrated blowing agent-containing solution or dispersion of a melamine / formaldehyde precondensate is foamed and the foam is cured, the foaming being carried out by heating to a temperature above the boiling point of the blowing agent in such a way that a steep increase in viscosity essentially does not start until the foaming process is finished.
  • the heating is preferably carried out with hot air, it can also be done by steam, high-frequency radiation or by utilizing the heat of reaction.
  • relatively thick foam molded articles can be produced by heating the blowing agent-containing solution or dispersion by microwave radiation.
  • the mol of melamine to formaldehyde obtained can vary within wide limits between 1: 1.5 and 1: 5, preferably between 1: 2 and 1: 3.5.
  • the molar ratio in the examples also lies in this range.
  • a corresponding, industrially produced, elastic foam is BASOTECT ® from BASF Aktiengesellschaft. It is being used to an increasing extent for sound and thermal insulation of buildings and parts of buildings. Like all materials made from aminoplast resins, BASOTECT ® emits very small amounts of formaldehyde. However, formaldehyde emissions increase with increasing temperature and humidity.
  • the invention was therefore based on the object of providing open-cell, elastic melamine / formaldehyde foams with such low formaldehyde emission, even under warm / humid conditions, that they measured according to the EU standard EN ISO 14 184-1 5 (water storage at 40 ° C, 1 hour) emit less than 40 mg, preferably less than 30 mg, of formaldehyde per kg of foam and thus meet the ⁇ KOTEX Standard 100 (quality seal of the textile industry for particularly low-pollution textiles).
  • a melamine / formaldehyde precondensate is used in the production of the foam, in which the molar ratio of melamine to formaldehyde is greater than 1: 2, but the molar ratio is 1: 1.5
  • Foams produced in this way with a density of 5 to 50 g-1 " 1 are characterized in that no or only a very weak signal occurs in the 13 C / MAS spectrum in the range from 65 to 85 ppm, based on the signal intensity of the Melamine rings at 166 ppm.
  • the ratio of the areas in the 13 C / MAS spectrum under the signals between 65 to 85 ppm and 155 and 25 175 ppm should be ⁇ 0.2, preferably ⁇ 0.1, particularly preferably ⁇ 0.05.
  • the process according to the invention is based on a melamine / formaldehyde precondensate.
  • Melamine / formaldehyde condensation products can, in addition to melamine, up to 50, preferably
  • thermoset formers containing up to 50, preferably up to 20% by weight of other aldehydes in condensed form.
  • An unmodified melamine / formaldehyde condensation product is particularly preferred.
  • thermoset formers are: alkyl- and aryl-substituted
  • aldehydes e.g. Acetaldehyde, trimethylolacetaldehyde, acrolein, benzaldehyde, furfural, glyoxal, glutaraldehyde, phthalaldehyde and terephthalate
  • melamine to formaldehyde is greater than 1: 2.0, it is preferably between 1: 1.0 and 1: 1.9, in particular between 1: 1.3 and 1: 1.8.
  • the precondensate used should therefore contain practically no sulfite groups, ie the sulfite group content should be below 1%, preferably below 0.1% and in particular zero.
  • an emulsifier or an emulsifier mixture is required to emulsify the blowing agent and to stabilize the foam.
  • Anionic, cationic and nonionic surfactants and mixtures thereof can be used as emulsifiers.
  • Suitable anionic surfactants are diphenylene oxide sulfonates, alkane and alkylbenzenesulfonates, alkylnaphthalenesulfonates, olefin sulfonates, alkyl ether sulfonates, fatty alcohol sulfates, ether sulfates, alpha sulfo fatty acid esters, acylamino alkane sulfonates, acyl thisates, alkyl ether alkyl sulfates and n-acyl phosphates, N-acyl phosphates.
  • Alkyl-phenol polyglycol ethers, fatty alcohol polyglycol ethers, fatty acid polyglycol ethers, fatty acid alkanolamides, EO / PO block copolymers, amine oxides, glycerol fatty acid esters, sorbitan esters and alkyl polyglucosides can be used as nonionic surfactants.
  • Alkyl triammonium salts, alkylbenzyldimethylammonium salts and alkylpyridinium salts are used as cationic emulsifiers.
  • the emulsifiers are preferably added in amounts of 0.2 to 5% by weight, based on the resin.
  • blowing agent In order to produce a foam from the melamine resin solution, it must contain a blowing agent, the amount depending on the desired density of the foam.
  • suitable physical blowing agents are: hydrocarbons, halogenated, in particular fluorinated, hydrocarbons, alcohols, ethers, ketones and esters in liquid form or air and CO as gases.
  • Possible chemical blowing agents are, for example, isocyanates in a mixture with water, C0 being released as an effective blowing agent, carbonates and bicarbonates in a mixture with acids which also produce C0, and azo compounds such as azodicarbonamide.
  • the aqueous solution or dispersion is between 1 and 40 wt .-%, based on the resin, of a physical blowing agent with a Boiling point between 0 and 80 ° C added; pentane is preferably 5 to 15% by weight.
  • Acidic compounds are used as hardeners, which catalyze the further condensation of the melamine resin.
  • the amounts are between 0.01 and 20, preferably between 0.05 and 5% by weight, based on the resin.
  • Inorganic and organic acids e.g. Hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, formic acid, acetic acid; Oxalic acid, toluenesulfonic acids, amidosulfonic acids and acid anhydrides.
  • the aqueous solution or dispersion is preferably free of further additives.
  • further additives for some purposes, however, it can be advantageous to use up to 20% by weight, preferably less than 10% by weight, based on the resin, of conventional additives, such as dyes.
  • foams are generally open-pore and can absorb water, it may be necessary for some applications to add water repellents in amounts of 0.2 to 5% by weight.
  • water repellents for example, Silicones, paraffins, silicone and fluorine surfactants.
  • the concentration of the melamine / formaldehyde precondensate in the mixture of precondensate and solvent can vary within wide limits between 55 and 85, preferably between 63 and 80,% by weight.
  • the preferred viscosity of the mixture of precondensate and solvent is between 1 and 300 ° dPas, preferably between 5 and 2000 dPas.
  • the additives are homogeneously mixed with the aqueous solution or dispersion of the melamine resin, and the blowing agent can also be injected under pressure, if necessary.
  • the blowing agent can also be injected under pressure, if necessary.
  • a fixed, e.g. spray dried melamine resin and then mix it with an aqueous solution of the emulsifier, hardener and blowing agent.
  • Mixing the components can e.g. be made in an extruder. After mixing, the solution or dispersion is discharged through a nozzle and immediately heated and foamed.
  • the heating of the blowing agent-containing solution or dispersion can in principle - as described in EP-B 17671 - be carried out by hot gases or high-frequency radiation. However, the required heating is preferably carried out by ultra-high frequency irradiation according to EP-B 37470.
  • This dielectric radiation it is possible to work with microwaves in the frequency range from 0.2 GHz to 100 GHz. For In industrial practice, frequencies of 0.915, 2.45 and 5.8 GHz are available, with 2.45 GHz being particularly preferred.
  • the radiation source for dielectric radiation is the magnetron, it also being possible to irradiate with several magnetrons at the same time. It must be ensured that the field distribution is as homogeneous as possible during the irradiation.
  • the irradiation is expediently carried out in such a way that the power consumption of the solution or dispersion is between 5 and 200, preferably between 9 and 120 KW, based on 1 kg of water in the solution or dispersion. If the power consumed is lower, there is no more foaming and the mixture only cures. If you work within the preferred range, the greater the power consumption, the faster the mixture foams. Above about 200 KW per kg of water, the foaming speed no longer increases significantly.
  • the mixture to be foamed is irradiated immediately after it has emerged from the foaming nozzle.
  • the mixture foaming as a result of the temperature increase and evaporation of the blowing agent is applied to circulating belts which form a rectangular channel for shaping the foam.
  • the foams according to the invention are expediently subjected to a temperature treatment. They are heated for 1 to 180 minutes, preferably 5 to 60 minutes, to temperatures between 120 and 300 ° C., in particular between 150 and 250 ° C., water, blowing agent and formaldehyde being largely removed. In practice, annealing at 220 ° C. for 30 minutes is sufficient for the foams according to the invention.
  • the formaldehyde content measured according to the EU standard EN ISO 14184-1 is then less than 40 mg, preferably less than 30 and in particular less than 20 mg per kg of foam. In the test method mentioned, a foam sample is extracted for 1 hour in 40 ° C warm water and the extracted formaldehyde is determined analytically.
  • the elastic foams produced according to the invention which preferably contain practically no sulfite groups, have a density of 5 to 50 g-1 " 1 .
  • the foams can be tempered and pressed in order to improve their performance properties.
  • the foams can be produced as sheets or sheets with a height of up to 2 m or as foam sheets with a thickness of a few mm.
  • the preferred foam height (in the direction of foaming) is between 50 cm and 150 cm when using microwaves of the frequency 5 2.45 GHz. All desired plate or film thicknesses can be cut out from such foam sheets.
  • the foams can be provided on one or both sides with cover layers or laminated, for example with paper, cardboard, glass fleece, wood, plasterboard, metal sheets or 10 foils, plastic foils, which can also be foamed if necessary.
  • the main area of application of the foams produced according to the invention is the thermal and acoustic insulation of buildings and
  • the foams can also be used for slightly abrasive cleaning, grinding and PoH sponges.
  • the sponges can also be made hydrophobic and oleophobic for special cleaning tasks. Because of the extremely low FA emissions compared to those previously on the foam
  • the foams according to the invention can also be used in the hygiene sector, e.g. Use in the form of thin nonwovens as a wound dressing or as part of baby diapers and incontinence products.
  • Example 2 of EP-B 37470 was reworked.
  • the melamine resin had a molar ratio of 1: 2 and contained 6% sulfite groups. After 30 minutes of tempering at 220 ° C, the formaldehyde emission was 85 mg per kg of foam, the NMR spectrum showed a clear signal between 65 and 85 ppm.
  • a spray-dried melamine resin (molar ratio 1: 1.6) are dissolved in 30 parts of water.
  • the mixture is then foamed as described in Comparative Example 1 and dried at 100.degree.
  • the NMR spectrum of the untempered foam shows a signal at 65 to 85 ppm, but it is significantly lower than in comparison example 1, and the formaldehyde emission is also lower at 480 mg. After 30 minutes of tempering at 220 ° C, the formaldehyde is virtually completely eliminated, less than 20 mg per kg of foam (limit of quantification of the analytical method) are measured. No signal between 65 and 85 ppm can be seen in the NMR spectrum (see Figure 2).

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

L'invention concerne un procédé pour produire des mousses élastiques à base d'un produit de condensation de mélamine/formaldéhyde. Ce procédé consiste à expanser un précondensat présentant un rapport molaire mélanine/formaldéhyde égal à 1: 2. Ces mousses ne présentent pratiquement aucune émission de formaldéhyde. Dans le spectre RMN 13 C/MAS, il n'apparaît aucun signal ou qu'un signal très faible dans la plage comprise entre 65 et 85 ppm.
PCT/EP2001/006399 2000-06-07 2001-06-06 Procedes pour produire des mousses a partir de condensats de melamine/formaldehyde Ceased WO2001094436A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001285731A AU2001285731A1 (en) 2000-06-07 2001-06-06 Method for producing foamed materials from melamine /formaldehyde condensates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10027770.5 2000-06-07
DE2000127770 DE10027770A1 (de) 2000-06-07 2000-06-07 Verfahren zur Herstellung von Schaumstoffen aus Melamin/Formaldehyd-Kondensaten

Publications (2)

Publication Number Publication Date
WO2001094436A2 true WO2001094436A2 (fr) 2001-12-13
WO2001094436A3 WO2001094436A3 (fr) 2002-05-16

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Country Status (3)

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AU (1) AU2001285731A1 (fr)
DE (1) DE10027770A1 (fr)
WO (1) WO2001094436A2 (fr)

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Publication number Priority date Publication date Assignee Title
EP1498680A1 (fr) 2003-07-16 2005-01-19 Basf Aktiengesellschaft Accumulateur en mousse de mélamine-formaldéhyde pour le maintien de froid et de chaud
EP1505105A1 (fr) * 2003-08-04 2005-02-09 Basf Aktiengesellschaft Pièces moulées en mousse de mélamine-formaldéhyde ayant une émission de formaldéhyde réduite
WO2007003608A1 (fr) * 2005-07-06 2007-01-11 Basf Aktiengesellschaft Reservoir a liquides compose d'une mousse de melamine/formaldehyde
WO2007118803A1 (fr) * 2006-04-18 2007-10-25 Basf Se Mousse à base d'aminoplaste comme outil de travail pouvant être stérilisé
WO2008068278A1 (fr) 2006-12-06 2008-06-12 Basf Se Substrat végétal à base de mousse à cellules ouvertes en mélamine-formaldéhyde
WO2008095932A1 (fr) 2007-02-08 2008-08-14 Basf Se Système d'irrigation et procédé d'irrigation ou de fertilisation
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EP2042155A1 (fr) 2007-09-28 2009-04-01 Basf Se Procédé de suppression de substances indissolubles dans l'eau de surfaces de substrat
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WO2010010046A1 (fr) * 2008-07-24 2010-01-28 Basf Se Substrats flexibles étendus avec surface abrasive
DE102010009587A1 (de) 2010-02-26 2011-09-01 Basf Se Flüssigschaum-gefülltes Schaumstoffformteil auf Basis eines Aminoplasten und Verfahren zur Stabilisierung von flüssigen Schäumen
DE102011005334A1 (de) 2010-03-12 2011-09-15 Basf Se Verfahren zur Herstellung hydrophober Melamin-/Formaldehydharzschaumstoffe
EP2368476A2 (fr) 2010-03-25 2011-09-28 The Procter & Gamble Company Instrument de nettoyage comprenant une mousse hybride
WO2011117269A1 (fr) 2010-03-25 2011-09-29 Basf Se Mousses et pièces moulées en matières de base contenant des résines réactives expansibles
US8043383B2 (en) 2006-06-30 2011-10-25 Georgia-Pacific Chemicals Llc Reducing formaldehyde emissions
EP2382907A2 (fr) 2010-04-29 2011-11-02 The Procter & Gamble Company Instrument de nettoyage comprenant une mousse compressée élastique
WO2011134778A1 (fr) 2010-04-29 2011-11-03 Basf Se Procédé de production de mousses comprimées élastiques à base de résine de mélamine/formaldéhyde
DE102011108755A1 (de) 2010-08-02 2012-02-02 Basf Se Multifunktionelle Wandelemente
US8173716B2 (en) 2007-03-06 2012-05-08 Basf Se Open-cell foam modified with hydrophobines
US8173219B2 (en) 2006-06-09 2012-05-08 Georgia-Pacific Chemicals Llc Porous fiberglass materials having reduced formaldehyde emissions
WO2012076492A1 (fr) 2010-12-07 2012-06-14 Basf Se Mousses de résine de mélamine contenant des matières de charge nanoporeuses
DE102011009397A1 (de) 2011-01-25 2012-07-26 Basf Se Verbundschaumstoff zur Schalldämmung
CN102977550A (zh) * 2012-12-13 2013-03-20 山东联合化工股份有限公司 密胺绝热硬质发泡板材的制备方法
US8546457B2 (en) 2007-08-14 2013-10-01 Basf Se Method for the production of abrasive foams
EP2735584A1 (fr) 2012-11-26 2014-05-28 Basf Se Mousse en résine en mélamine déformable à chaud avec matériau de remplissage à particules
US8937106B2 (en) 2010-12-07 2015-01-20 Basf Se Melamine resin foams with nanoporous fillers
US20160115685A1 (en) * 2013-06-14 2016-04-28 Aspen Aerogels, Inc. Insulating composite materials comprising an inorganic aerogel and a melamine foam
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CN107629403A (zh) * 2017-10-09 2018-01-26 四川大学 一种低甲醛释放软质三聚氰胺甲醛泡沫的制备方法及其应用
WO2019053143A1 (fr) 2017-09-13 2019-03-21 Basf Se Mousses auxétiques de polyuréthane et de mélamine par compression triaxiale
WO2019232087A1 (fr) 2018-05-31 2019-12-05 Aspen Aerogels, Inc. Compositions d'aérogel renforcées de classe ignifuge
WO2020221800A1 (fr) 2019-05-02 2020-11-05 Basf Se Mousse de mélamine-formaldéhyde à émission de formaldéhyde réduite
WO2021113188A1 (fr) 2019-12-02 2021-06-10 Aspen Aerogels Inc. Composants et systèmes pour gérer des problèmes d'emballement thermique dans des batteries de véhicule électrique
WO2021113189A1 (fr) 2019-12-02 2021-06-10 Aspen Aerogels Inc. Composants à base d'aérogel et systèmes de gestion thermique de véhicules électriques
WO2021142169A1 (fr) 2020-01-07 2021-07-15 Aspen Aerogels Inc. Élément de gestion thermique de batterie
WO2021207154A1 (fr) 2020-04-06 2021-10-14 Aspen Aerogels Inc. Compositions d'aérogel amélioré et procédés
WO2021228739A1 (fr) 2020-05-14 2021-11-18 Basf Se Procédé de nettoyage d'équipement médical
DE202022107130U1 (de) 2022-12-21 2023-01-19 Basf Se Filtermedium aus einem offenzelligen Melamin-Formaldehyd-Schaumstoff zur Wasserreinigung

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Cited By (73)

* Cited by examiner, † Cited by third party
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