IT9021003A1 - USEFUL POLYESTERS AS SUBSTANCES THAT ELIMINATE SMOKE AND TOXIC GASES FOR POLYURETHANE - Google Patents
USEFUL POLYESTERS AS SUBSTANCES THAT ELIMINATE SMOKE AND TOXIC GASES FOR POLYURETHANE Download PDFInfo
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- IT9021003A1 IT9021003A1 IT021003A IT2100390A IT9021003A1 IT 9021003 A1 IT9021003 A1 IT 9021003A1 IT 021003 A IT021003 A IT 021003A IT 2100390 A IT2100390 A IT 2100390A IT 9021003 A1 IT9021003 A1 IT 9021003A1
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- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- GOCPTMPZDPBBSV-UHFFFAOYSA-N octadecanoic acid;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.CCCCCCCCCCCCCCCCCC(O)=O GOCPTMPZDPBBSV-UHFFFAOYSA-N 0.000 description 1
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 1
- 235000019407 octafluorocyclobutane Nutrition 0.000 description 1
- OWUDFCCCSKRXAN-UHFFFAOYSA-N oxalic acid;1,3,5-triazine-2,4,6-triamine Chemical compound OC(=O)C(O)=O.NC1=NC(N)=NC(N)=N1 OWUDFCCCSKRXAN-UHFFFAOYSA-N 0.000 description 1
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- QVJYHZQHDMNONA-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1 QVJYHZQHDMNONA-UHFFFAOYSA-N 0.000 description 1
- OBNAOHSAPQWLGU-UHFFFAOYSA-N phthalic acid;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OC(=O)C1=CC=CC=C1C(O)=O OBNAOHSAPQWLGU-UHFFFAOYSA-N 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4291—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from polyester forming components containing monoepoxy 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
DESCRIZIONE DELL'INVENZIONE INDUSTRIALE DESCRIPTION OF THE INDUSTRIAL INVENTION
"Poliesteri utili come sostanze che eliminano fumo e gas tossici per poliuretani" La presente invenzione riguarda l'eliminazione Polyesters Useful as Smoke Eliminating Substances and Toxic Gases for Polyurethanes The present invention relates to elimination
della formazione di fumo e di gas tossici nella the formation of smoke and toxic gases in the
combustione di sostanze polimeriche naturali e combustion of natural polymeric substances e
sintetiche, in particolare quelle contenenti porzioni synthetic, especially those containing portions
di isocianato, per esempio materiali espansi poliuretanici flessibili e rigidi, che vengono usati of isocyanate, for example flexible and rigid polyurethane foam materials, which are used
nella fabbricazione di mobili, nel settore dei in the manufacture of furniture, in the sector of
trasporti, in strutture decorative, isolanti e in transport, in decorative, insulating structures and in
strutture edilizie. building structures.
Gli acidi carbossilici sono sistemi che carbonizzano ben noti e vengono rivendicati come utili Carboxylic acids are well known carbonizing systems and are claimed to be useful
in qualità di additivi per eliminare il fumo in questo acting as additives to eliminate smoke in this
contesto. Tuttavia, i composti acidi reagiscono con context. However, acidic compounds react with
componenti che vengono usati nella produzione di components that are used in the production of
poliuretani e che sono molto difficili da introdurre polyurethanes and which are very difficult to introduce
in un materiale espanso poliuretanico, in particolari in a polyurethane foam material, in particular
materiali espansi poliuretanici flessibili e, così, flexible polyurethane foam materials and, thus,
non sono interessanti per il fabbricante di materiale they are of no interest to the material manufacturer
espanso . expanded.
Esteri di sistemi di acidi policarbossilici sono Esters of polycarboxylic acid systems are
descritti in EP 75424 come additivi per l'eliminazione del fumo per materiali espansi poliuretanici, ma soltanto quando vengono usati insieme con altri componenti. Inoltre, esteri di acidi policarbossilici derivati da alcooli monoossidrilici semplici non fanno diminuire il livello di fumo all'atto della combustione del materiale espanso. disclosed in EP 75424 as smoke suppression additives for polyurethane foam materials, but only when used in conjunction with other components. Furthermore, esters of polycarboxylic acids derived from simple monohydric alcohols do not decrease the level of smoke upon combustion of the foamed material.
Sorprendentemente, la Richiedente ha trovato che certi poliesteri fanno diminuire notevolmente sia la velocità di formazione che i livelli di fumo e di gas tossici all'atto della combustione del materiale espanso poliuretanico. Inoltre, questi poliesteri agiscono da soli e non richiedono l'aggiunta di altri componenti, sebbene, se si desidera, si possano usare altri componenti. Inoltre, i poliesteri della presente invenzione possono venire incorporati facilmente nel materiale espanso poliuretanico in normali condizioni di fabbricazione. Surprisingly, the Applicant has found that certain polyesters considerably decrease both the rate of formation and the levels of smoke and toxic gases upon combustion of the polyurethane foam material. Furthermore, these polyesters act alone and do not require the addition of other components, although other components may be used if desired. Furthermore, the polyesters of the present invention can be easily incorporated into the polyurethane foam material under normal manufacturing conditions.
Pertanto, la presente invenzione mette a disposizione un poliestere che ha un numero di acidità inferiore a 3 mg KOH/g e che è derivato da: Therefore, the present invention provides a polyester which has an acid number lower than 3 mg KOH / g and which is derived from:
I (A) un componente aromatico che contiene 4 gruppi carbossilici oppure una sua anidride ed eventualmente, (B) uno o più componenti che contengono da 2 a 12 preferibilmente da 2 a 4 gruppi carbossilici oppure da I a 6 preferibilmente 1 oppure 2 gruppi di anidridi carbossi 1iche , scelti da: I (A) an aromatic component which contains 4 carboxylic groups or one of its anhydrides and optionally, (B) one or more components which contain from 2 to 12 preferably from 2 to 4 carboxy groups or from I to 6 preferably 1 or 2 groups of carboxylic anhydrides, selected from:
(B1) un componente di un acido carbossilico alifatico che contiene da 2 a 16 atomi di carbonio; (B1) a component of an aliphatic carboxylic acid which contains from 2 to 16 carbon atoms;
(B2 ) un acido carbossilico non-aromatico ciclico che contiene da 7 a 16 atomi di carbonio; e (B2) a cyclic non-aromatic carboxylic acid containing 7 to 16 carbon atoms; And
(B3) un acido carbossilico aromatico contenente 8-16 atomi di carbonio; (B3) an aromatic carboxylic acid containing 8-16 carbon atoms;
II eventualmente (C) almeno un componente alifatico, cicloal ifatico oppure aromatico, preferibilmente alifatico, poliossidrilico contenente da 2 a 8, preferibilmente da 2 a 4 gruppi ossidrilici; e II optionally (C) at least one aliphatic, cycloaliphatic or aromatic, preferably aliphatic, polyhydroxy component containing from 2 to 8, preferably from 2 to 4 hydroxyl groups; And
III (D) un alchilen-ossido . III (D) an alkylene oxide.
Tra gli esempi di adatti componenti acidi [A3 sono compresi gli acidi piromellitico, naftalene-tetracarbossilico, 3,3' ,4,4'-benzofenontetracarbossilico, 3,3' ,4,4'-difeniltetracarbossilico, 3,3',-4,4 '-difeniletere-tetracarbossi lico e, 3, 3',4,4' -difeni lsolfonetetracarbossilico , relative anidridi e loro derivati alogenati. Preferibilmente, il componente lA3 è acido piromellitico oppure è dianidride dell'acido piromellitico. Examples of suitable acidic components [A3 include pyromellitic, naphthalene-tetracarboxylic acids, 3,3 ', 4,4'-benzophenontetracarboxylic, 3,3', 4,4'-diphenyltetracarboxylic, 3,3 ', - 4 , 4 '-diphenylether-tetracarboxylic and, 3, 3', 4,4 '-sulfonetetracarboxylic diphenes, relative anhydrides and their halogenated derivatives. Preferably, component 1A3 is pyromellitic acid or is pyromellitic acid dianhydride.
Un componente costituito da un acido carbossilico alifatico [B<1>] può essere saturo oppure insaturo, preferibilmente saturo, e può essere non sostituito oppure sostituito con uno o più alogeni, gruppi amminici oppure, preferibilmente, gruppi ossidrilici. Tra gli esempi di adatti acidi alifatici sono compresi gli acidi ossalico, maionico, succinico, glutarico ed adipico, miscele reperibili in commercio di acidi dicarbossilici per esempio AGS ( miscele di acidi adipico, glutarico e succinico), gli acidi pimelico, azelaico, sebacico, malico, tartarico, citrico, dibromosuccinico, etilendiamminotetracarbossilico, maleico, fumarico, itaconico, metileneglutarico , dicloromaleico e polimaleici e relative anidridi. Preferibilmente (Β1) è un acido saturo, più preferibilmente è un acido bicarbossilico , in particolare acido adipico. A component consisting of an aliphatic carboxylic acid [B <1>] can be saturated or unsaturated, preferably saturated, and can be unsubstituted or substituted with one or more halogens, amino groups or, preferably, hydroxyl groups. Examples of suitable aliphatic acids include oxalic, mayionic, succinic, glutaric and adipic acids, commercially available mixtures of dicarboxylic acids for example AGS (mixtures of adipic, glutaric and succinic acids), pimelic, azelaic, sebacic acids, malic, tartaric, citric, dibromosuccinic, ethylenediaminetetracarboxylic, maleic, fumaric, itaconic, methyleneglutaric, dichloromal and polymeric and relative anhydrides. Preferably (Β1) is a saturated acid, more preferably it is a dicarboxylic acid, in particular adipic acid.
Il componente acido non-aromatico ciclico [B<2>] può essere interrotto da un atomo -0- oppure può essere sostituito con uno o più gruppi chetonici. Tra gli esempi di acidi adatti sono compresi acidi ciclopentan- oppure cicloesan-poli-carbossilici , acido ciclopentanon-policarbossilico oppure acido cicloesanon-policarbossilico, acido tetraidrofuran-policarbossi lico e relative anidridi. Si preferiscono acidi tetracarbossilici , in particolare acido tetraidrofuran-tetracarbossilico e loro anidridi . The cyclic non-aromatic acid component [B <2>] can be interrupted by an -0- atom or it can be substituted with one or more ketone groups. Examples of suitable acids include cyclopentane- or cyclohexane-polycarboxylic acids, cyclopentanone-polycarboxylic acid or cyclohexanone-polycarboxylic acid, tetrahydrofuran-polycarboxylic acid and related anhydrides. Tetracarboxylic acids are preferred, in particular tetrahydrofuran-tetracarboxylic acid and their anhydrides.
Il componente acido aromatico[B<3>] può contenere da 2 a 4 gruppi carbossilici oppure 1 oppure 2 gruppi di anidride e può essere non sostituito oppure può essere sostituito con uno o più atomi di alogeno. Tra gli esempi di acidi adatti sono compresi gli acidi ftalico, isoftalico, tereftalico, naftalen-bicarbossilico, trimellitico , naftalen-tetracarbossilico , 3,3' ,4,4'-benzofenontetracarbossilico e acido 3,3' ,4,4'-difeniltetracarbossilico, relative anidridi e loro derivati alogenati per esempio acido 3, 5,6-tribromotrimellitico o relativa anidride. Gli acidi bicarbossilici sono preferiti come (B3), in particolare gli acidi ftalico, isoftalico e tereftalico. The aromatic acid component [B <3>] can contain from 2 to 4 carboxylic groups or 1 or 2 anhydride groups and can be unsubstituted or can be replaced with one or more halogen atoms. Examples of suitable acids include phthalic, isophthalic, terephthalic, naphthalene dicarboxylic, trimellitic, naphthalene-tetracarboxylic, 3,3 ', 4,4'-benzophenontetracarboxylic acids and 3,3', 4,4'-diphenyltetracarboxylic acid. , relative anhydrides and their halogenated derivatives, for example 3, 5,6-tribromotrimellitic acid or relative anhydride. Dicarboxylic acids are preferred as (B3), in particular phthalic, isophthalic and terephthalic acids.
Il componente poliossidrilico [C] può essere alifatico, cicloalifatico oppure aromatico, eventualmente sostituito con uno o più atomi di alogeno. Esso può essere un poliolo alifatico saturo contenente da 2 a 52 atomi di carbonio e da 2 a 4 gruppi ossidrilici oppure può essere un alcool ciclo-alifatico contenente da 6 a 10 atomi di carbonio e da 2 a 4 gruppi ossidrilici. The polyhydric component [C] can be aliphatic, cycloaliphatic or aromatic, optionally substituted with one or more halogen atoms. It can be a saturated aliphatic polyol containing from 2 to 52 carbon atoms and from 2 to 4 hydroxyl groups or it can be a cycloaliphatic alcohol containing from 6 to 10 carbon atoms and from 2 to 4 hydroxyl groups.
Tra gli esempi di adatti componenti dioli alifatici [C] sono compresi glicol etilenico, glicol propilenico, 1,4-butandiolo , 1,6-esandiolo , 1,10-decandiolo, dietilene glicol, poliossialchilene glicoli di diversi pesi molecolari per esempio polietilene glicol 200, polietilene glicol 400, polietilene glicol 600, polietilene glicol 1000, polipropilene glicol 200, polipropilene glicol 425, polipropilene glicol 700 e polipropilene glicol 1000 e glicoli sostituiti con alogeni come dibromoneopentil glicol. Tra gli esempi di componenti adatti contenenti 3 ò 4 gruppi ossìdrilici [C] sono compresi trimetiloletano, 1 ,1,1-trimetilolpropano, 1,2,6-esantriolo, glicerolo e pentaeritritolo . Examples of suitable aliphatic diol components [C] include ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,10-decanediol, diethylene glycol, polyoxyalkylene glycols of different molecular weights e.g. polyethylene glycol 200, polyethylene glycol 400, polyethylene glycol 600, polyethylene glycol 1000, polypropylene glycol 200, polypropylene glycol 425, polypropylene glycol 700 and polypropylene glycol 1000 and glycols substituted with halogens such as dibromoneopentyl glycol. Examples of suitable components containing 3 or 4 hydroxy groups [C] include trimethylolethane, 1,1-trimethylolpropane, 1,2,6-hexantriol, glycerol and pentaerythritol.
Tra gli esempi di adatti polioli cicloalifatici vi sono cicloesan-1 ,2-oppure 1,4-dimetanol i; e cicloesanone-oppure cicloesanol-2 ,21,6,6'-tetrametanolo . Examples of suitable cycloaliphatic polyols include cyclohexane-1, 2-or 1,4-dimethanol; and cyclohexanone-or cyclohexanol-2,1,6,6'-tetramethanol.
Tra gli esempi di adatti componenti poliolici aromatici [C] sono compresi dioli come catecolo, resorcinolo, idrochinone, naftalen-dioli , bisfenolo A, antrachinone-dioli , benzene 1,2-oppure 1,4-dimetanoli; difenil-4,4'-dimetanolo e loro derivati alogenati. Examples of suitable aromatic polyol components [C] include diols such as catechol, resorcinol, hydroquinone, naphthalen-diols, bisphenol A, anthraquinone-diols, benzene 1,2- or 1,4-dimethanols; diphenyl-4,4'-dimethanol and their halogenated derivatives.
Il componente (C) preferibilmente è un componente del poliestere ed è preferibilmente alifatico, più preferibilmente un diolo, in particolare dietilen-glicol oppure un poliossialchilen-glicol . Component (C) is preferably a component of the polyester and is preferably aliphatic, more preferably a diol, in particular diethylene glycol or a polyoxyalkylene glycol.
Esempi di adatti alchilen-ossidi (D) sono etilene-ossido, propilene-ossido oppure loro miscele. Si possono preparare i poliesteri della presente invenzione mediante procedimenti tradizionali noti a coloro che sono esperti nel settore come esterificazione oppure transesterificazione. Così, la preparazione può consistere nel fare reagire un acido policarbossilico oppure un *anidride di un acido policarbossilico (A) e qualsiasi altro componente acido (B) con il componente poliossidrilico (C) ad una temperatura compresa tra 20°C e 300°C, per esempio usando il poliolo (C) come solvente, oppure in presenza di un altro solvente adatto come metiletilchetone , tetraidrof urano, toluene oppure xilene, fino a che il numero di acidità è compreso tra 10 mg KOH/g e 100 mg KOH/g, preferibilmente fino a che 11 numero di acidità è compreso tra 20 mg KOH/g e 40 mg KOH/g e trattare il poliestere ottenuto con un alchilen-ossido (D), preferibilmente usando un adatto catalizzatore come bicarbonato di sodio e preferibilmente in un solvente come toluene oppure xilene, fino a che il numero di acidità è inferiore a 3 mg KOH/g. Si può effetturare la reazione tra (A), (B) e (C) in presenza di un catalizzatore per esempio alcossidi di stagno oppure alcossidi di titanio, N-metilimmidazolo, trietilendiammina, trifenil-fosfina, acido p-toluensolfonico oppure altri catalizzatori noti a coloro che sono esperti nel settore . ;Come alternativa, si possono fare reagire l'acido policarbossilico oppure la sua anidride (A) e qualsiasi altro componente acido (B) direttamente con l'ossido di alchilene (D) fino a che il numero di acidità è inferiore a 3 mg KOH/g. ;Si possono impiegare i poliesteri che eliminano il fumo della presente invenzione in diversi materiali plastici, ma essi sono particolarmente adatti per materiali nei quali sono incorporati legami di isocianato, in particolare poliisocianurati e poliuretani, principalmente i materiali espansi flessibili o rigidi comunemente a base di toluen-diisocianato (TDI) e di difenilmetan-4,4' -diisocianato (MDI ) e, in particolare, i materiali espansi flessibili basati usualmente su TDI, che vengono impiegati in mobili moderni, attrezzi e tubi di raccordo. Questi poliuretani possono essere basati, per esempio, su poliesteri polioli oppure su polieteri polioli, trialcanolammine oppure polioli amminici, per esempio quelli derivati da prodotti di addizione di alchilen-ossidi di ammine e ammoniaca. Esempi di polietere-polioli sono quelli basati su copolimeri di ossido di etilene e/o ossidi di propilene e anche su polioli modificati per esempio polioli di polimeri (per esempio polieteri polioli ai quali sono state innestate cariche poliviniliche), polieteri polioli contenenti particelle disperse di poliurea oppure polietere polioli contenenti prodotti di reazione di composti poliidrossiamminici e di poliisocianati . Tra gli esempi di poliesteri polioli sono compresi poli(ossidietilene adipati), poli(ossidietilene tereftalati) e policaprolattoni . In essi possono essere incorporati diversi agenti di rigonfiamento, come acqua, anidride carbonica e peraloidrocarburi per esempio cloruro di metilene, gas liquefatti che hanno punti di ebollizione inferiori a 27°C e superiori a 15°C, oppure altri gas inerti come azoto, anidride carbonica aggiunta come tale, metano, elio ed argon. Tra i gas inizialmente liquefatti adatti sono compresi idrocarburi fluorurati alifatici e cicloalifatici che vaporizzano in corrispondenza della temperatura della massa di espansione oppure al di sotto della temperatura della massa di espansione. Tali gas sono almeno parzialmente fluorurati e possono anche essere altrimenti alogenati. Esempi illustrativi degli agenti di rigonfiamento costituiti da idrocarburi fluorurati preferiti sono tri cloromonofluorometano; diclorodifluorometano; 1,1-dicloro-l-fluoroetano; esafluorociclobutano; e ottafluorociclobutano. Tra le altre sostanze coadiuvanti ( o loro residui) che possono venire introdotte sono compresi catalizzatori, per esempio composti dello stagno come ottoato stannoso, acetato di dibutil stagno e laurato di dibutil stagno, tensioattivi ed emulsionanti come nonil-fenoli sostituiti, prodotti di condensazione acido grasso/etilen ossido, copolimeri a blocco di alchilen-ossido oppure composti contenenti silicio, per esempio. poliidimetil silossani), poli(fenilmetilsilossani) oppure copolimeri ad innesto poli(dimetilsilossano) - poliossialchilene ed anche sostanze che ritardano la propagazione della fiamma, come allumine idrate, idrossido di magnesio, composti contenenti alogeno e/o contenenti fosforo ivi compresi sali di metalli di acidi fosfonici, ossidi di antimonio, composti contenenti boro come borace, grafite, per esempio un grafite defogliata, materiali ceramici oppure melammina oppure suoi derivati come per esempio sali di melammina. Tra i sali di melammina adatti sono compresi melammina borato, melammina cianurato, dimelammina fosfato, melammina fosfonati, melammina solfonati, e melammina carbossilati, come melammina ftalato, melammina stearato e melammina ossalato. Quando si usa un agente di ritardo della fiamma, il rapporto tra poliestere e agente di ritardo della fiamma nel materiale combustibile può essere compreso tra 10:90 e 90:10 in peso. Se si desidera, nella formulazione si possono introdurre ingredienti intumescenti, per esempio polifosfati di ammonio. ;Oltreacomposti dello stagno, il catalizzatore preferibilmente contiene un‘ammina. Tra i catalizzatori a base di ammine adatti sono compresi uno o più dei seguenti: Ν,Ν'-dimetilcicloesilammina; metil-dicicloesil-ammina; N-metilmorfolina; N-etilmorfolina; N-ottadecilmorfolina; trietilammina; tributilammina, triottilammina, Ν,Ν,Ν',N1-tetrametilendiammina; Ν,Ν,-Ν',Ν'-tetrametil-1,3-butan-diammina; trietanolammina; Ν,Ν-dimetiletanolammina; triisopropanolammina; N-metil-dietanolammina; bis(2-di-metilamminoeti1)-etere; esadecildimetilammina; Ν,Ν-dimetilbenzilammina; trimetilammina; trietilendiammina (ossia 1,4-diazabiciclo(2.2.2-ottanoJ); il formiato e altri sali di trietilen-diammina; prodotti di addizione di ossialchilene dei gruppi amminici di ammine primarie e secondarie e altri per esempio catalizzatori a base di ammine che sono ben noti nel settore della produzione dei poliuretani. ;Pertanto, la presente invenzione inoltre mette a disposizione una composizione che comprende una sostanza combustibile, preferibilmente un materiale espanso poliuretanico, contenente legami di uretani e, come sostanza che elimina il fumo e i gas tossici, un poliestere della presente invenzione. Il poliestere può venire incorporato mediante miscelazione con la formulazione di poliolo usata per preparare il poliuretano prima di mescolarlo con il componente isocianato. Il poliestere, che è di per sè un poliolo, può venire usato in una quantità che è compresa tra 5% e 100% preferibilmente tra 10% e 30% in peso del poliolo. Pertanto, il poliestere può costituire tutto il poliolo usato per preparare il poliuretano. ;Così, la presente invenzione, inoltre mette a disposizione un poliuretano, in particolare un materiale espanso poliuretanico formato da un diisocianato oppure da un poliisocianato e da un poliestere come definito sopra. ;Si possono usare le composizioni della presente invenzione in un'ampia varietà di prodotti per esempio seggiole, divani, seggiolini e diverse altre forme di sedili, materassi, imbottiture, cuscini, parti posteriori espanse per tappeti, tendine e materiali compositi tessili e anche materiali espansi per isolamenti termici e per isolamenti acustici. In tali applicazioni, le composizioni della presente invenzione, spesso, verranno usate in materiali compositi o in montaggi con un *ampia serie di altri materiali ivi compresi materiali tessili naturali e sintetici, per esempio cuoio, cotone, lana, poliestere, poliammide, composti acrilici, polivinilcloruro, polipropilene, velluti viscosi; imbottiture supplementari, interrivestimenti , tessiture, barriere e altri materiali diversi da costruzione come legno, metalli, materie plastiche, materiale per intonaci, fibre di vetro, etc. Inoltre si possono anche introdurre altri mezzi per ridurre l'infiammabilità e lo sviluppo di fumo e di gas tossici, per esempio interstrati, materiali espansi-barriera e materiali tessili per il ritardo della propagazione della fiamma. Examples of suitable alkylene oxides (D) are ethylene oxide, propylene oxide or their mixtures. The polyesters of the present invention can be prepared by conventional methods known to those skilled in the art such as esterification or transesterification. Thus, the preparation may consist in making a polycarboxylic acid or an anhydride of a polycarboxylic acid (A) and any other acid component (B) react with the polyhydric component (C) at a temperature between 20 ° C and 300 ° C , for example using polyol (C) as a solvent, or in the presence of another suitable solvent such as methylethylketone, tetrahydrofuran, toluene or xylene, until the acid number is between 10 mg KOH / g and 100 mg KOH / g , preferably until the acid number is between 20 mg KOH / g and 40 mg KOH / g and treat the polyester obtained with an alkylene oxide (D), preferably using a suitable catalyst such as sodium bicarbonate and preferably in a solvent such as toluene or xylene, as long as the acid number is less than 3 mg KOH / g. The reaction between (A), (B) and (C) can be carried out in the presence of a catalyst for example tin alkoxides or titanium alkoxides, N-methylimidazole, triethylenediamine, triphenylphosphine, p-toluenesulfonic acid or other known catalysts to those who are experts in the field. ; Alternatively, the polycarboxylic acid or its anhydride (A) and any other acid component (B) can be reacted directly with the alkylene oxide (D) until the acid number is less than 3 mg KOH / g. The smoke suppressing polyesters of the present invention can be used in various plastics, but they are particularly suitable for materials in which isocyanate bonds are incorporated, particularly polyisocyanurates and polyurethanes, mainly flexible or rigid foam materials commonly based on toluene-diisocyanate (TDI) and diphenylmethane-4,4 '-diisocyanate (MDI) and, in particular, the flexible foam materials usually based on TDI, which are used in modern furniture, tools and connecting pipes. These polyurethanes can be based, for example, on polyester polyols or on polyether polyols, trialkanolamines or amino polyols, for example those derived from addition products of alkylene oxides of amines and ammonia. Examples of polyether-polyols are those based on copolymers of ethylene oxide and / or propylene oxides and also on modified polyols for example polymer polyols (for example polyether polyols to which polyvinyl fillers have been grafted), polyether polyols containing dispersed particles of polyurea or polyether polyols containing reaction products of polyhydroxyamine compounds and polyisocyanates. Examples of polyester polyols include poly (oxyethylene adipates), poly (oxyethylene terephthalates) and polycaprolactones. Various swelling agents can be incorporated in them, such as water, carbon dioxide and peralohydrocarbons for example methylene chloride, liquefied gases that have boiling points below 27 ° C and above 15 ° C, or other inert gases such as nitrogen, anhydride added carbon as such, methane, helium and argon. Suitable initially liquefied gases include aliphatic and cycloaliphatic fluorinated hydrocarbons which vaporize at the temperature of the expansion mass or below the temperature of the expansion mass. Such gases are at least partially fluorinated and can also be otherwise halogenated. Illustrative examples of the preferred fluorinated hydrocarbon swelling agents are trichloromonofluoromethane; dichlorodifluoromethane; 1,1-dichloro-1-fluoroethane; hexafluorocyclobutane; and octafluorocyclobutane. Other adjuvant substances (or residues thereof) which may be introduced include catalysts, for example tin compounds such as stannous octoate, dibutyl tin acetate and dibutyl tin laurate, surfactants and emulsifiers such as substituted nonyl phenols, acid condensation products fat / ethylene oxide, alkylene oxide block copolymers or compounds containing silicon, for example. polyhydimethyl siloxanes), poly (phenylmethylsiloxanes) or graft copolymers poly (dimethylsiloxane) - polyoxyalkylene and also substances which retard the spread of flame, such as hydrated aluminas, magnesium hydroxide, compounds containing halogen and / or containing phosphorus including metal salts of phosphonic acids, antimony oxides, compounds containing boron such as borax, graphite, for example a defoliated graphite, ceramic materials or melamine or its derivatives such as melamine salts. Suitable melamine salts include melamine borate, melamine cyanurate, dimelamine phosphate, melamine phosphonates, melamine sulfonates, and melamine carboxylates, such as melamine phthalate, melamine stearate and melamine oxalate. When using a flame retardant agent, the ratio of polyester to flame retardant in the combustible material can be from 10:90 to 90:10 by weight. If desired, intumescent ingredients, for example ammonium polyphosphates, may be introduced into the formulation. In addition to tin compounds, the catalyst preferably contains an amine. Suitable amine catalysts include one or more of the following: Ν, Ν'-dimethylcyclohexylamine; methyl-dicyclohexyl-amine; N-methylmorpholine; N-ethylmorpholine; N-octadecylmorpholine; triethylamine; tributylamine, triotylamine, Ν, Ν, Ν ', N1-tetramethylenediamine; Ν, Ν, -Ν ', Ν'-tetramethyl-1,3-butan-diamine; triethanolamine; Ν, Ν-dimethylethanolamine; triisopropanolamine; N-methyl-diethanolamine; bis (2-di-methylaminoethyl) -ether; hexadecyldimethylamine; Ν, Ν-dimethylbenzylamine; trimethylamine; triethylenediamine (i.e. 1,4-diazabicyclo (2.2.2-octaneJ); formate and other triethylene diamine salts; oxyalkylene addition products of the amino groups of primary and secondary amines and other e.g. amine-based catalysts which are well known in the field of polyurethane production.; Therefore, the present invention further provides a composition which comprises a combustible substance, preferably a polyurethane foam material, containing urethane linkages and, as a substance which eliminates smoke and toxic gases, a polyester of the present invention. The polyester can be incorporated by mixing with the polyol formulation used to prepare the polyurethane before mixing it with the isocyanate component. The polyester, which is itself a polyol, can be used in an amount which is between 5% and 100% preferably between 10% and 30% by weight of the polyol. Therefore, the polyester can constitute all the polyol used. or to prepare the polyurethane. Thus, the present invention also provides a polyurethane, in particular a polyurethane foam material formed by a diisocyanate or a polyisocyanate and a polyester as defined above. The compositions of the present invention can be used in a wide variety of products such as chairs, sofas, booster seats and various other forms of seats, mattresses, upholstery, cushions, foam backs for carpets, curtains and textile composites and also materials foams for thermal and acoustic insulation. In such applications, the compositions of the present invention will often be used in composites or in assemblies with a wide range of other materials including natural and synthetic textile materials, e.g. leather, cotton, wool, polyester, polyamide, acrylic compounds. , polyvinyl chloride, polypropylene, viscous velvets; additional padding, interlinings, textures, barriers and other different construction materials such as wood, metals, plastics, plaster materials, glass fibers, etc. In addition, other means can also be introduced to reduce flammability and the development of smoke and toxic gases, for example interlayers, barrier foam materials and flame retardant textiles.
Gli esempi che seguono illustrano la presente invenzione . The following examples illustrate the present invention.
Esempio 1; 30,5 g (0,12 moli) di acido piromei litico, 17,5 g (0,12 moli) di acido adipico e 127,2 g (1,20 moli) di dietilenglicol vengono introdotti in un recipiente di reazione dotato di un efficace agitatore e vengono riscaldati lentamente a 200°C sotto un flusso di azoto gassoso. La miscela viene riscaldata a questa temperatura e l'acqua di condensazione viene distillata dalla massa di reazione con una temperatura di testa di 100°C (.±. 5°C). La reazione viene controllata effettuando determinazioni del numero di acidità. In corrispondenza di un numero di acidità di 20 mg KOH/g, la miscela di reazione viene raffreddata e l'apparecchiatura viene adattata, per il riflusso. Nella miscela si introducono 232 g (4 moli) di ossido di propilene, 200 mi di toluene e una quantità catalitica di bicarbonato di sodio. La miscela viene nuovamente controllata mediante determinazioni del numero di acidità fino a che si raggiunge un numero di acidità inferiore a 2 mg KOH/g. Example 1; 30.5 g (0.12 moles) of pyrometolytic acid, 17.5 g (0.12 moles) of adipic acid and 127.2 g (1.20 moles) of diethylene glycol are placed in a reaction vessel equipped with an effective stirrer and are slowly heated to 200 ° C under a stream of nitrogen gas. The mixture is heated to this temperature and the condensation water is distilled from the reaction mass with a head temperature of 100 ° C (. ±. 5 ° C). The reaction is controlled by making acid number determinations. At an acid number of 20 mg KOH / g, the reaction mixture is cooled and the apparatus is adapted, for reflux. 232 g (4 moles) of propylene oxide, 200 ml of toluene and a catalytic quantity of sodium bicarbonate are introduced into the mixture. The mixture is checked again by determining the acid number until an acid number lower than 2 mg KOH / g is reached.
L'ossido di propilene in eccesso, il toluene e il dietilenglicol vengono allontanati a pressione ridotta ottenendo così un olio avente un numero di acidità di 1,9 mg KOH/g, un numero di ossidrile di 309 mg KOH/g ed una viscosità di 9,875 Pa s. Excess propylene oxide, toluene and diethylene glycol are removed under reduced pressure thus obtaining an oil having an acid number of 1.9 mg KOH / g, a hydroxyl number of 309 mg KOH / g and a viscosity of 9.875 Pa s.
Esempio 2: 30,5 g (0,12 moli) di acido piromellitico, 17,5 g (0,12 moli) di acido adipico e 127,2 g (1,20 moli) di dietilenglicol vengono introdotti in un reattore dotato di un efficace agitatore e vengono riscaldati lentamente a 200°C sotto un flusso di azoto gassoso. La miscela viene riscaldata a questa temperatura e l'acqua di condensazione viene distillata dalla massa di reazione ad una temperatura di testa di 100°C (+ 5°C). La reazione viene controllata mediante determinazioni del numero di acidità. In corrispondenza di un numero di acidità di 30 mg KOH/g, la miscela di reazione viene raffreddata e l'apparecchiatura viene adattata per il riflusso. Nella miscela si introducono 116 g (2 moli) di ossido di propilene, 200 mi di toluene ed una quantità catalitica di bicarbonato di sodio. La reazione anche in questo caso viene controllata mediante determinazioni del numero di acidità fino a che si raggiunge un numero di acidità inferiore a 2 mg KOH/g. L'ossido di propilene in eccesso, il toluene e il dietilenglicol vengono allontanati a pressione ridotta ottenendo così un olio avente un numero di acidità di 2,8 mg KOH/g, un numero di ossidrile di 326 mg KOH/g ed una viscosità di 8.900 Pa s. Example 2: 30.5 g (0.12 moles) of pyromellitic acid, 17.5 g (0.12 moles) of adipic acid and 127.2 g (1.20 moles) of diethylene glycol are introduced into a reactor equipped with an effective stirrer and are slowly heated to 200 ° C under a stream of nitrogen gas. The mixture is heated to this temperature and the condensation water is distilled from the reaction mass at a head temperature of 100 ° C (+ 5 ° C). The reaction is controlled by acid number determinations. At an acid number of 30 mg KOH / g, the reaction mixture is cooled and the equipment is adapted for reflux. 116 g (2 moles) of propylene oxide, 200 ml of toluene and a catalytic quantity of sodium bicarbonate are introduced into the mixture. In this case too, the reaction is controlled by determining the acid number until an acid number lower than 2 mg KOH / g is reached. Excess propylene oxide, toluene and diethylene glycol are removed under reduced pressure thus obtaining an oil having an acid number of 2.8 mg KOH / g, a hydroxyl number of 326 mg KOH / g and a viscosity of 8,900 Pa s.
Esemplo 3: 65,4 g (0,3 moli) di dianidride piromell itica 1200 g (1,2 moli) di glicolpropilenico 1000 vengono introdotti in un reattore e riscaldati lentamente a 200°C sotto un flusso di azoto gassoso. La miscela viene riscaldata a questa temperatura e l'acqua di condensazione viene distillata dalla massa di reazione ad una temperatura di testa di 100°C (+_ 5°C). La reazione viene controllata mediante determinazioni del numero di acidità. In corrispondenza di un numero di acidità di 23,7 mg KOH/g, la miscela di reazione viene raffreddata e l'apparecchiatura viene adattata per il riflusso. Nella miscela si introducono 174 g (3,0 moli) di ossido di propilene ed una quantità catalitica di bicarbonato di sodio. Example 3: 65.4 g (0.3 moles) of pyromellic dianhydride 1200 g (1.2 moles) of propylene glycol 1000 are introduced into a reactor and slowly heated to 200 ° C under a nitrogen gas flow. The mixture is heated to this temperature and the condensation water is distilled from the reaction mass at a head temperature of 100 ° C (+ _ 5 ° C). The reaction is controlled by acid number determinations. At an acid number of 23.7 mg KOH / g, the reaction mixture is cooled and the equipment is adapted for reflux. 174 g (3.0 moles) of propylene oxide and a catalytic quantity of sodium bicarbonate are introduced into the mixture.
La reazione, anche in questo caso, viene controllata mediante determinazione del numero di acidità fino a che si raggiunge un numero di acidità inferiore a 2 mg KOH/g. L'ossido di propilene in eccesso viene allontanato a pressicre ridotta ottenendo così un olio avente un numero di acidità di 1,9 mg KOH/g, un numero di ossidrile di 112 mg KOH/g ed una viscosità di 0,7724 Pa s. The reaction, also in this case, is controlled by determining the acid number until an acid number lower than 2 mg KOH / g is reached. The excess propylene oxide is removed at reduced pressure thus obtaining an oil having an acid number of 1.9 mg KOH / g, a hydroxyl number of 112 mg KOH / g and a viscosity of 0.7724 Pa s.
Esempio 4: 50,8 g (0,2 moli) di acido piromellitico , 116,0 g (2,0 moli) di ossido di propilene e 100 mi di tetraidrofurano vengono introdotti in un reattore dotato di un efficiente agitatore e vengono riscaldati lentamente fino alla temperatura di riflusso. Si controlla la reazione mediante determinazioni del numero di acidità. In corrispondenza di un numero di acidità di 59 mg KOH/g, si aggiunge una quantità catalitica di bicarbonato di sodio e si controlla il numero di acidità fino ad ottenere un valore di 42 mg KOH/g. Si evapora a secco la miscela di reazione e si introduce l'olio ottenuto in un reattore insieme con 58,0 g (1,0 moli) di propi lenossido e 100 mi di toluene e si riscalda lentamente fino alla temperatura di riflusso. In corrispondenza di un numero di acidità di 9 mg KOH/g, si aggiunge un ' ulteriore quantità catalitica di bicarbonato di sodio e si controlla la reazione fino a che si ottiene un numero di acidità inferiore a 2 mg KOH/g. Si allontanano ossido di propilene in eccesso e toluene a pressione ridotta ottenendo così un olio avente un numero di acidità di 1,0 mg KOH/g e un numero di ossidrile di 321 mg KOH/g. Example 4: 50.8 g (0.2 mol) of pyromellitic acid, 116.0 g (2.0 mol) of propylene oxide and 100 ml of tetrahydrofuran are introduced into a reactor equipped with an efficient stirrer and are heated slowly up to the reflux temperature. The reaction is controlled by determining the acid number. At an acid number of 59 mg KOH / g, a catalytic quantity of sodium bicarbonate is added and the acid number is controlled until a value of 42 mg KOH / g is obtained. The reaction mixture is evaporated to dryness and the oil obtained is introduced into a reactor together with 58.0 g (1.0 moles) of propylene oxide and 100 ml of toluene and slowly heated up to the reflux temperature. At an acid number of 9 mg KOH / g, a further catalytic quantity of sodium bicarbonate is added and the reaction is controlled until an acid number lower than 2 mg KOH / g is obtained. Excess propylene oxide and toluene are removed under reduced pressure thus obtaining an oil having an acid number of 1.0 mg KOH / g and a hydroxyl number of 321 mg KOH / g.
L'uso delle nuove composizi erti,dipoliestere della presente invenzione come additivi che riducono efficacemente la quantità di fumo e di gas tossici sviluppati dalla combustione di un materiale espanso di poliuretano flessibile viene illustrato dai seguenti esempi 4-6. The use of the novel dipolyester compositions of the present invention as additives which effectively reduce the amount of smoke and toxic gases developed by the combustion of a flexible polyurethane foam is illustrated by the following Examples 4-6.
Esempio 5: Si preparara un materiale espanso poliuretanico flessibile usando la seguente formulazione . Example 5: A flexible polyurethane foam material is prepared using the following formulation.
Si mescolano tra di loro, il poliolo, acqua Ν,Ν-dlmetiletanolammina e tensioattivo siliconico usando un agitatore a 4 pale a 2000 giri/minuto. Polyol, water, Ν-dlmethylethanolamine and silicone surfactant are mixed together using a 4-blade agitator at 2000 rpm.
Si aggiunge il dilaurato di dibutil-stagno e si agita per 5 secondi. Alla fine, si aggiunge rapidamente TDI preventivamente pesato. Si mescola la miscela per 5 secondi, quindi la si versa in uno stampo. Si lascia espandere la schiuma e quindi la si conserva per 24 ore a 23°C e con umidità relativa 50%. The dibutyl tin dilaurate is added and stirred for 5 seconds. Finally, the pre-weighed TDI is quickly added. The mixture is stirred for 5 seconds, then poured into a mold. The foam is allowed to expand and then it is kept for 24 hours at 23 ° C and 50% relative humidity.
Il materiale espanso viene tagliato in cubi aventi un peso di 5 g (_+ 0,2 g) e si misura la quantità di fumo prodotta all’atto della combustione, nel modo che segue, usando una camera per fumo standard Aminco NBS descritta in ASTM E662, ma adottando un procedimento di prova modificato. Il campione di materiale espanso viene posto su una garza di filo metallico supportata su un cavalletto all'interno della camera del fumo e fatto .bruciare con un fiammifero. Ciascun campione di materiale espanso viene esaminato effettuando 3 prove. The foam is cut into cubes having a weight of 5 g (_ + 0.2 g) and the amount of smoke produced upon combustion is measured as follows, using a standard Aminco NBS smoke chamber described in ASTM E662, but using a modified test procedure. The foam sample is placed on a wire gauze supported on a tripod inside the smoke chamber and burned with a match. Each sample of foam material is examined by carrying out 3 tests.
La densità ottica specifica media viene calcolata in corrispondenza di 1 minuto (D1), 2 minuti (D2) e 3 minuti (D ) partendo dal momento dell'inizio della combustione. Si registra anche la densità ottica specifica massima media corretta per il deposito di fuliggine sulle lenti tDmax (corr)l. I risultati sono riportati nella tabella 1. The average specific optical density is calculated at 1 minute (D1), 2 minutes (D2) and 3 minutes (D) starting from the moment of combustion. The average maximum specific optical density corrected for the soot deposit on the lenses is also recorded tDmax (corr) l. The results are shown in Table 1.
Esempi 6 e 7: Si preparano campioni di materiale espanso poliuretanico flessibile contenente le composizioni di poliestere della presente invenzione adottando il metodo dell'esempio 5 mescolando l'opportuna quantità della composizionedi poliestere nella miscela prima dell'aggiunta del dilaurato di dibutil-stagno e di TDI . Le quantità usate sono indicate nella tabella 1 come parti per cento parti di poliolo (php). Examples 6 and 7: Samples of flexible polyurethane foam material containing the polyester compositions of the present invention are prepared by adopting the method of Example 5 by mixing the appropriate amount of the polyester composition in the mixture before adding the dibutyl tin dilaurate and TDI. The quantities used are indicated in Table 1 as parts per hundred parts of polyol (php).
Sebbene si possano usare le composizioni di poliestere senza la necessità di alcun cambiamento sostanziale per questa formulazione, coloro che sono esperti nel settore comprenderanno che si possono effettuare piccole modifiche, per esempio per ciò che riguarda le quantità di catalizzatore, allo scopo di controllare le proprietà del materiale espanso prodotto. Although polyester compositions can be used without the need for any substantial change for this formulation, those skilled in the art will understand that small changes can be made, for example in the amounts of catalyst, in order to control the properties. of the foam material produced.
Si preparano campioni del materiale espanso così ottenuto e si esaminano seguendo il procedimento descritto nell'esempio 5 e i valori della densità ottica così ottenuti sono indicati nella tabella 1. Samples of the foam material thus obtained are prepared and examined following the procedure described in Example 5 and the values of the optical density thus obtained are indicated in Table 1.
I risultati indicati nella tabella 1 indicano che l'introduzione dei poliesteri della presente invenzione nel materiale espanso poliuretanico flessibile fà diminuire la quantità totale di fumo formato durante la combustione, in confronto al materiale espanso non trattato (esempio 5) misurato mediante Dmax (corr). Inoltre, i poliesteri hanno l'effetto di fare diminuire notevolmente la velocità in corrispondenza della quale il fumo viene prodotto, The results indicated in table 1 indicate that the introduction of the polyesters of the present invention into the flexible polyurethane foam material decreases the total amount of smoke formed during combustion, compared to the untreated foam material (example 5) measured by Dmax (corr) . Furthermore, polyesters have the effect of significantly decreasing the rate at which smoke is produced,
misurata con i valori di densità ottica dopo 1 minuto, 2 minuti e 3 minuti (D 1 , D , e D ). measured with the optical density values after 1 minute, 2 minutes and 3 minutes (D 1, D, and D).
L'esempio che segue illustra l'uso dei nuovi poliesteri della presente invenzione come componente poliolo di un materiale espanso poliuretanico flessibile . The following example illustrates the use of the new polyesters of the present invention as a polyol component of a flexible polyurethane foam material.
Esempio 8: Si prepara un materiale espanso flessibile mediante il metodo dell'esempio 5, ma usando la seguente formulazione. Example 8: A flexible foam material is prepared by the method of Example 5, but using the following formulation.
Si esamina il materiale espanso ottenuto per ciò che riguarda lo sviluppo di fumo adottando il metodo dell'esempio 5. I risultati ottenuti sono quelli che seguono e indicano che il materiale espanso emette una quantità di fumo inferiore rispetto a quella del materiale espanso di controllo (esempio 5). The foam material obtained is examined as regards the development of smoke by adopting the method of Example 5. The results obtained are the following and indicate that the foam material emits a lower quantity of smoke than that of the control foam material ( example 5).
Densità ottica Optical density
Claims (20)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898916824A GB8916824D0 (en) | 1989-07-22 | 1989-07-22 | Polyester |
Publications (3)
Publication Number | Publication Date |
---|---|
IT9021003A0 IT9021003A0 (en) | 1990-07-20 |
IT9021003A1 true IT9021003A1 (en) | 1992-01-20 |
IT1247421B IT1247421B (en) | 1994-12-13 |
Family
ID=10660496
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IT02100390A IT1247421B (en) | 1989-07-22 | 1990-07-20 | USEFUL POLYESTERS AS SUBSTANCES THAT ELIMINATE SMOKE AND TOXIC GASES FOR POLYURETHANE |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPH0366726A (en) |
CA (1) | CA2021687A1 (en) |
DE (1) | DE4022999A1 (en) |
FR (1) | FR2649984B1 (en) |
GB (2) | GB8916824D0 (en) |
IT (1) | IT1247421B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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ES2543739T3 (en) * | 2009-04-09 | 2015-08-21 | Bayer Intellectual Property Gmbh | Polyester terephthalic acid and oligo alkylene oxides |
JP5475065B2 (en) * | 2011-07-08 | 2014-04-16 | 三洋化成工業株式会社 | Strength improver for polyurethane foam production |
JP2013036033A (en) * | 2011-07-12 | 2013-02-21 | Sanyo Chem Ind Ltd | Polyol composition for polyurethane foam production |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3454530A (en) * | 1966-03-07 | 1969-07-08 | Leslie C Case | Novel polyols which are reaction products of a monoepoxide and a cyclic monoanhydride |
US4039487A (en) * | 1976-01-19 | 1977-08-02 | The Upjohn Company | Cellular isocyanurate polymer |
FR2451383A1 (en) * | 1979-03-15 | 1980-10-10 | Witco Chemical | Non-flammable poly:isocyanurate foam prepn. - using poly:isocyanate and polyester derived from aromatic or aliphatic poly-acid and glycol |
US4446306A (en) * | 1982-05-20 | 1984-05-01 | Allied Corporation | Oligomer-containing mixtures useful as fiber surface treating agents and processes for the production and use thereof |
US4551519A (en) * | 1983-05-02 | 1985-11-05 | Allied Corporation | Process for the production of fluorinated pyromellitate containing mixtures useful as surfactants |
US4647651A (en) * | 1983-05-02 | 1987-03-03 | Allied Corporation | Process for the production of fluorinated pyromellitate containing mixtures useful as surfactants |
DE3613875A1 (en) * | 1986-04-24 | 1987-10-29 | Basf Ag | METHOD FOR PRODUCING POLYESTER POLYOLS |
GB8801525D0 (en) * | 1988-01-23 | 1988-02-24 | Ciba Geigy Ag | Smoke & toxic gas suppressant composition |
-
1989
- 1989-07-22 GB GB898916824A patent/GB8916824D0/en active Pending
-
1990
- 1990-07-16 GB GB9015599A patent/GB2234253B/en not_active Expired - Lifetime
- 1990-07-19 FR FR909009225A patent/FR2649984B1/en not_active Expired - Fee Related
- 1990-07-19 DE DE4022999A patent/DE4022999A1/en not_active Ceased
- 1990-07-20 IT IT02100390A patent/IT1247421B/en active IP Right Grant
- 1990-07-20 JP JP2192826A patent/JPH0366726A/en active Pending
- 1990-07-20 CA CA002021687A patent/CA2021687A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
FR2649984B1 (en) | 1994-09-16 |
GB9015599D0 (en) | 1990-09-05 |
JPH0366726A (en) | 1991-03-22 |
IT9021003A0 (en) | 1990-07-20 |
IT1247421B (en) | 1994-12-13 |
CA2021687A1 (en) | 1991-01-23 |
DE4022999A1 (en) | 1991-01-31 |
GB8916824D0 (en) | 1989-09-06 |
GB2234253A (en) | 1991-01-30 |
GB2234253B (en) | 1992-04-22 |
FR2649984A1 (en) | 1991-01-25 |
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