EP0000360A1 - Elastomères de polyuréthane-urée et leur procédé de préparation - Google Patents

Elastomères de polyuréthane-urée et leur procédé de préparation Download PDF

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Publication number
EP0000360A1
EP0000360A1 EP78100282A EP78100282A EP0000360A1 EP 0000360 A1 EP0000360 A1 EP 0000360A1 EP 78100282 A EP78100282 A EP 78100282A EP 78100282 A EP78100282 A EP 78100282A EP 0000360 A1 EP0000360 A1 EP 0000360A1
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EP
European Patent Office
Prior art keywords
polyurethane
diamino
diphenylmethane
tetramethyl
urea elastomers
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.)
Withdrawn
Application number
EP78100282A
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German (de)
English (en)
Inventor
Herbert Dr. Stutz
Karl Heinz Dr. Illers
Ludwig Dr. Schuster
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BASF SE
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BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0000360A1 publication Critical patent/EP0000360A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step

Definitions

  • the invention relates to polyurethane-urea elastomers with improved temperature behavior, produced on the basis of prepolymers containing cycloaliphatically bound NCO groups and 3,3 ', 5,5'-tetramethyl-4,4'-diamino-diphenylmethane and a process for their preparation.
  • the service temperature range of an elastomeric material is mainly determined by the temperature dependence of the module in chewing Schukelastic area determined, which is limited down by freezing and upwards by softening and melting away the material.
  • Moca-hardened elastomers are characterized above all by the low temperature dependence of the module between approx. -30 ° C and 130 0 e, which is practically completely temperature-independent, especially between room temperature and 130 ° C.
  • polyurethane-urea elastomers can be produced which the above described Do not have disadvantages and have a module that is practically independent of temperature in the range between room temperature and approx. 130 ° C. if prepolymers with cycloaliphatically bound isocyanate end groups with 3,3 ', 5,5'-tetramethyl-4,4'-diamino -diphenylmethane can be cured.
  • the polyurethane-urea elastomers produced according to the invention surprisingly have a greatly improved temperature behavior.
  • Higher molecular weight polyhydroxyl compounds suitable for the production of the polyurethanes according to the invention are the polyesters, polyester amides, polyethers, polyacetals and / or butanediene oils with terminal hydroxyl groups and molecular weights between 600 and 10,000, preferably from 800 to 3,000, which are known and customary in the prior art.
  • Linear, hydroxyl-containing polyesters and polyethers are preferably used.
  • the polyhydroxyl compounds must be at least predominantly linear, i.e. be constructed difunctionally in the sense of the isocyanate reaction. If polyfunctional polyfunctional compounds are used proportionally, they can only be used in such quantities that the average functionality of the mixture is between 2.0 and 2.2, preferably between 2.0 and 2.1.
  • the polyhydroxyl compounds mentioned can be used either as individual components or in the form of mixtures with one another.
  • Suitable hydroxyl-containing polyesters or polyester amides can be prepared, for example, from dicarboxylic acids having 2 to 12 carbon atoms and polyhydric alcohols, optionally with the use of amino alcohols or diamines.
  • suitable dicarboxylic acids are: aliphatic dicarboxylic acids such as succinic acid. Glutaric acid, adipic acid, suberic acid, azelaic acid and sebacic acid as well as aromatic dicarboxylic acids such as phthalic acid, Isophthalic acid and terephthalic acid.
  • the dicarboxylic acids can be used both individually and in a mixture with one another. Aliphatic dicarboxylic acids such as adipic acid and succinic acid are preferably used.
  • carboxylic acid derivatives such as carboxylic acid esters with 1 to 4 carbon atoms in the alcohol radical, carboxylic acid anhydrides or carboxylic acid chlorides, instead of the free carboxylic acids.
  • polyhydric alcohols examples include glycols with 2 to 16, preferably 2 to 6 carbon atoms, such as ethylene glycol, diethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,10-decanediol, 2,2-dimethylpropanediol -1,3, 2,2,4-trimethylpropanediol-1,3, propanediol-1,2 and -1,3, di- and tripropylene glycol.
  • the polyhydric alcohols can be used alone or, if appropriate, in mixtures with one another or with small amounts.
  • esters of carbonic acid with the diols mentioned in particular those with 4 to 6 carbon atoms, such as 1,4-butanediol and / or 1,6-hexanediol, condensation products of ⁇ -hydroxycarboxylic acids, for example w-hydroxycaproic acid, and preferably polymerization products of cyclic lactones , for example optionally substituted E-caprolactones.
  • Suitable polyethers with terminal hydroxyl groups can be prepared by reacting one or more alkylene oxides having 2 to 4 carbon atoms in the alkylene radical with a starter molecule which contains several, preferably two, active hydrogen atoms bonded.
  • Suitable alkylene oxides are, for example, ethylene oxide, propylene oxide, epichlorohydrin, 1,2- and 2,3-butylene oxide.
  • the alkylene oxides can be individually, older be used sequentially or as mixtures.
  • suitable starter molecules are: water, amino alcohols, such as N-alkyldiethanolamines and diols, such as ethylene glycol, propylene glycol, butanediol and hexanediol.
  • Suitable polyetherols are also the hydroxyl-containing polymerization products of tetrahydrofuran. Like the polyesters mentioned above, the hydroxyl-containing polyethers are predominantly linear, ie difunctional. Particularly suitable polyacetals are water-insoluble formals such as polybutanediol formal and polyhexanediol formal.
  • proportionally low molecular weight polyhydroxyl compounds with molecular weights below 300 can also be used in a mixture with the higher molecular weight polyhydroxyl compounds.
  • the molar ratios of the higher and lower molecular weight polyhydroxyl compounds should not exceed a value of approximately 1: 1, since otherwise the viscosities can easily increase too much.
  • polyhydroxyl compounds with molecular weights below 300 are: butanediol, hexanediol, di- and triethylene glycol and di- and tripropylene glycol.
  • Butanediol or diethylene glycol are preferably used.
  • Organic diisocyanates suitable for producing the polyurethane-urea elastomers according to the invention must have at least one cycloaliphatically bound isocyanate group in the molecule.
  • methylcyclohexyl diisocyanates such as 2,4- and 2,6-methyl-cyclohexyl diisocyanate, phenyl-cyclohexyl methane diisocyanates and preferably the different isomers of dicyclohexyl methane diisocyanate and 3-isocyanato-methyl-3,5,5-trimethylcyclo-hexyl isocyanate are suitable (JPDJ). Mixtures may also be used of these diisocyanates are used. Aliphatic diisocanates are not suitable for the production of the polyurethanes according to the invention.
  • the reaction of the higher molecular weight and optionally low molecular weight polyhydroxyl compounds with the organic diisocyanate or optionally with several of the organic diisocyanates described above to form a prepolymer with terminal isocyanate groups takes place in the known and customary manner at temperatures between 80 and 150 ° C., preferably from 80 to 120 ° C. .
  • the known and customary catalysts such as tertiary amines, tin compounds and the like can also be used to accelerate the reaction.
  • the molar ratios between higher and optionally low molecular weight polyhydroxyl compound and organic diisocyanate are, depending on the desired hardness of the end product, between 1: 1.2 to about 1:10, preferably from 1: 1.5 to 1: 5.
  • a molar ratio of polyhydroxy compound to diisocyanate such as 1: 1.2 should not be undercut, since otherwise the viscosities increase too much and the mixtures are difficult to process.
  • the polyhydroxyl compound can initially also be reacted with only part of the diisocyanate or one of the diisocyanates to form a prepolymer and the rest can be added subsequently.
  • the higher molecular weight riyhydroxyl compound is dewatered as usual by treatment at elevated temperatures and under reduced pressure, optionally mixed with the low molecular weight polyhydroxyl compounds and reacted with the organic diisocyanate.
  • the finished prepolymers containing NCO groups can be further processed immediately after production with the 3,3 ', 5,5'-tetramethyl-4,41-diamino-diphenylmethane, but since they have excellent storage stability, they can also be used over a longer period of time stored in the absence of humidity without changing their properties. If the prepolymer containing NCO groups is not further processed immediately after production, it is advisable to free it from dissolved gases by mixing it with the diamine by vacuum treatment at higher temperatures, since otherwise easily blown castings are obtained. This measure is common when casting compact polyurethanes.
  • the ratio of the isocyanate groups of the prepolymer to the amino group of the hardener should therefore generally between 0.8 and 1.2, preferably approximately 1: 1.
  • the NCO-group-containing prepolymers For processing, the NCO-group-containing prepolymers at temperatures of 80 to 120 o C, preferably around 100 ° C, with the previously molten 3,3 ', 5,5'-tetramethyl-4,4'-diamino-diphenylmethane mixed homogenized and the pourable mixture poured into molds.
  • the castings are cured to complete the reaction by tempering at temperatures between about 80 and 150 ° C for several hours.
  • annealing temperatures around 100 ° C give the best results.
  • the annealing time depends primarily on the temperatures used, in general 2 to 12 hours are sufficient at temperatures around 100 to 120 ° C.
  • auxiliaries and additives can also be added to the reaction mixture, such as catalysts, retarders, dyes, pigments, organic or mineral fillers, anti-aging or hydrolysis agents.
  • the polyurethane-urea elastomers produced according to the invention have outstanding hydrolysis resistance and low-temperature properties; They are particularly characterized by the fact that their module is largely constant over a wide temperature range. They can therefore be used for a variety of applications, for example for the manufacture of machine parts, rollers, rollers, seals without restrictions.
  • the hardness of this sample is 72 Shore A, the tear strength is 16.3 N / mm 2 and the tear resistance is 21 N / mm.
  • the shear modulus curve of this elastomer in the figure shows a continuous drop in the module between the glass transition at -51 ° C. and the end valid softening above 150 ° C.
  • the material is therefore very sensitive to temperature and therefore not suitable for general use.
  • Example 1 is repeated, but using 180 g (0.2 mol) of PTHF, 50.46 g of hexane-1,6-diisocyanate and 19.8 g of 4,4'-diaminodiphenylmethane.
  • the reactivity of this mixture is so high that it can no longer be processed by hand after the amine has been mixed in.
  • the experiment 1 b described above is repeated using 180 g (0.2 mol) of PTHF, 42.1 g of hexane-1,6-diisocyanate and 12.7 g of 3,3 ', 5,5'-tetramethyl-4 , 4'-diamino-diphenylmethane.
  • Comparative experiments 1b and 1c show that aliphatic diisocyanates are not suitable for the production of the polyurethane-urea elastomers according to the invention.
  • the material results in tough and transparent cast parts, which have a hardness of 85 Shore A, a tensile strength of 12 N / mm 2 , an elongation at break of 500% and a tear strength of 35 N / mm.
  • the shear modulus curve in the figure shows, analogously to example 1, a wide temperature range between approximately 0 and 150 o C, in which the module is only slightly temperature-dependent.
  • Example 2 The experiment from Example 2 is repeated using 180 g (0.2 mol) of PTHF, 78.6 g of dicyclohexylmethane diisocyanate (Hylene W) and 19.8 g of 4,4'-diamino-diphenylmethane.
  • an elastomer is produced using 180 g (0.2 mol) of PTHF, 55.6 g of IPDI and 12.7 g of 3,3 ', 5,5'-tetramethyl-4,4'. - diamino-diphenylmethane.
  • the glass temperature of this material is -53 ° C, the shear modulus between room temperature and approx. 130 ° C is almost independent of the temperature.
  • the glass temperature of this material is -32 ° C, the shear modulus is constant between room temperature and 120 ° C.
  • the glass temperature of this material is -72 o C, the shear modulus is practically constant in the range between 0 and 170 ° C.
  • the glass temperature of this material is -72 o C, the shear modulus is independent of the temperature between 0 and 170 ° C.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
EP78100282A 1977-07-14 1978-06-30 Elastomères de polyuréthane-urée et leur procédé de préparation Withdrawn EP0000360A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2731815 1977-07-14
DE19772731815 DE2731815A1 (de) 1977-07-14 1977-07-14 Polyurethan-harnstoff-elastomere

Publications (1)

Publication Number Publication Date
EP0000360A1 true EP0000360A1 (fr) 1979-01-24

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100282A Withdrawn EP0000360A1 (fr) 1977-07-14 1978-06-30 Elastomères de polyuréthane-urée et leur procédé de préparation

Country Status (6)

Country Link
US (1) US4208507A (fr)
EP (1) EP0000360A1 (fr)
CA (1) CA1134540A (fr)
DE (1) DE2731815A1 (fr)
ES (1) ES471695A1 (fr)
IT (1) IT1105235B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0026915A2 (fr) * 1979-10-08 1981-04-15 BASF Aktiengesellschaft Procédé pour la préparation de corps moulés à base de polyuréthanne-polyurée contenant éventuellement des cellules
GB2133802A (en) * 1983-01-17 1984-08-01 Grace W R & Co High molecular weight aromatic amine scavengers
GB2174709A (en) * 1985-04-29 1986-11-12 Mobay Corp Elastomer polyurethane-polyurea coatings based on bis(4-isocyanatocyclohexyl)methane
EP0807135A1 (fr) * 1995-02-02 1997-11-19 Simula Inc. Polyurethane resistant aux impacts et son procede de fabrication
US6127505A (en) * 1995-02-02 2000-10-03 Simula Inc. Impact resistant polyurethane and method of manufacture thereof

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2902090A1 (de) * 1979-01-19 1980-07-24 Bayer Ag Hitzehaertbare beschichtungsmassen und verfahren zur beschichtung von substraten
DE2920501A1 (de) * 1979-05-21 1980-11-27 Bayer Ag Verfahren zur herstellung von polyurethanharnstoffelastomeren
DE2933165A1 (de) * 1979-08-16 1981-03-26 Bayer Ag, 51373 Leverkusen Verfahren zur herstellung von dynamisch besonders belastbaren luftreifen
US4425468A (en) 1981-12-31 1984-01-10 Ppg Industries, Inc. Polyurea-polyurethane acrylate polymer dispersions
DE3200412A1 (de) * 1982-01-09 1983-07-21 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von gegebenenfalls zelligen polyurethanharnstoffelastomeren
DE3429149A1 (de) * 1984-08-08 1986-02-20 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von stabilisierten polyaminen, stabilisierte polyamine retardierter reaktivitaet und ihre verwendung zur polyurethanherstellung
US5077330A (en) * 1988-08-29 1991-12-31 Armstrong World Industries, Inc. Conductive polyurethane-urea/polyethylene oxide
US5510445A (en) * 1994-11-22 1996-04-23 Bayer Corporation Process for castable polyurea elastomers
US5811506A (en) * 1997-02-03 1998-09-22 Simula Inc. Extrudable thermoplastic elastomeric urea-extended polyurethane
US6258917B1 (en) 1996-05-21 2001-07-10 Simula, Inc. Extrudable thermoplastic elastomeric urea-extended polyurethane
US20060241273A1 (en) * 2001-11-16 2006-10-26 Bojkova Nina V High impact poly (urethane urea) polysulfides
US7144969B2 (en) * 2001-11-16 2006-12-05 Ppg Industries Ohio, Inc. Impact resistant polyureaurethane and polyureaurethane prepolymer having low NCO/OH ratio
US20030096935A1 (en) * 2001-11-16 2003-05-22 Nagpal Vidhu J. Impact resistant polyureaurethane and method of preparation
US20070142604A1 (en) * 2005-12-16 2007-06-21 Nina Bojkova Polyurethanes and sulfur-containing polyurethanes and methods of preparation
US8017720B2 (en) * 2005-12-16 2011-09-13 Ppg Industries Ohio, Inc. Sulfur-containing oligomers and high index polyurethanes prepared therefrom
JP3938515B2 (ja) * 2002-06-12 2007-06-27 Ｓｒｉスポーツ株式会社 ゴルフボール
US20040021133A1 (en) * 2002-07-31 2004-02-05 Nagpal Vidhu J. High refractive index polymerizable composition
US7009032B2 (en) * 2002-12-20 2006-03-07 Ppg Industries Ohio, Inc. Sulfide-containing polythiols
US11591436B2 (en) 2004-09-01 2023-02-28 Ppg Industries Ohio, Inc. Polyurethane article and methods of making the same
US11248083B2 (en) 2004-09-01 2022-02-15 Ppg Industries Ohio, Inc. Aircraft windows
US20090280709A1 (en) 2004-09-01 2009-11-12 Ppg Industries Ohio, Inc. Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same
US11149107B2 (en) 2004-09-01 2021-10-19 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US9598527B2 (en) 2004-09-01 2017-03-21 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US9464169B2 (en) 2004-09-01 2016-10-11 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US11008418B2 (en) 2004-09-01 2021-05-18 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20090280329A1 (en) 2004-09-01 2009-11-12 Ppg Industries Ohio, Inc. Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same
CN101437875B (zh) * 2006-05-05 2011-05-11 Ppg工业俄亥俄公司 硫醚官能的低聚多硫醇以及由其制备的制品
US9568643B2 (en) 2012-12-13 2017-02-14 Ppg Industries Ohio, Inc. Polyurethane urea-containing compositions and optical articles and methods for preparing them
US9500445B2 (en) * 2013-09-10 2016-11-22 The United States Of America As Represented By The Secretary Of The Army Multi-layer matrix composite having improved energy absorption, dissipation and shock wave mitigation capabilities
US11059746B2 (en) 2015-08-10 2021-07-13 America as represented by the Secretary of the Army Thermoplastic cycloaliphatic polyamide matrix resins for next-generation energy absorbing applications

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1479890A (fr) * 1965-05-14 1967-05-05 Bayer Ag Procédé de préparation de matières plastiques réticulées selon le processus depolyaddition d'isocyanates
FR2159530A1 (fr) * 1971-11-13 1973-06-22 Bayer Ag

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1240654B (de) * 1965-05-14 1967-05-18 Bayer Ag Verfahren zur Herstellung vernetzter Kunststoffe nach dem Isocyanat-Polyadditions-Verfahren

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1479890A (fr) * 1965-05-14 1967-05-05 Bayer Ag Procédé de préparation de matières plastiques réticulées selon le processus depolyaddition d'isocyanates
FR2159530A1 (fr) * 1971-11-13 1973-06-22 Bayer Ag

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0026915A2 (fr) * 1979-10-08 1981-04-15 BASF Aktiengesellschaft Procédé pour la préparation de corps moulés à base de polyuréthanne-polyurée contenant éventuellement des cellules
EP0026915A3 (en) * 1979-10-08 1981-07-29 Basf Aktiengesellschaft Process for preparing moulded polyurethane-polyurea articles which may contain cells
GB2133802A (en) * 1983-01-17 1984-08-01 Grace W R & Co High molecular weight aromatic amine scavengers
GB2174709A (en) * 1985-04-29 1986-11-12 Mobay Corp Elastomer polyurethane-polyurea coatings based on bis(4-isocyanatocyclohexyl)methane
EP0807135A1 (fr) * 1995-02-02 1997-11-19 Simula Inc. Polyurethane resistant aux impacts et son procede de fabrication
EP0807135A4 (fr) * 1995-02-02 1998-03-18 Simula Inc Polyurethane resistant aux impacts et son procede de fabrication
US5962617A (en) * 1995-02-02 1999-10-05 Simula Inc. Impact resistant polyurethane and method of manufacture thereof
US6127505A (en) * 1995-02-02 2000-10-03 Simula Inc. Impact resistant polyurethane and method of manufacture thereof

Also Published As

Publication number Publication date
CA1134540A (fr) 1982-10-26
IT1105235B (it) 1985-10-28
US4208507A (en) 1980-06-17
DE2731815A1 (de) 1979-02-01
IT7850185A0 (it) 1978-07-06
ES471695A1 (es) 1979-10-01

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