EP0879254A1 - Materiaux en polyurethanne - Google Patents

Materiaux en polyurethanne

Info

Publication number
EP0879254A1
EP0879254A1 EP97902240A EP97902240A EP0879254A1 EP 0879254 A1 EP0879254 A1 EP 0879254A1 EP 97902240 A EP97902240 A EP 97902240A EP 97902240 A EP97902240 A EP 97902240A EP 0879254 A1 EP0879254 A1 EP 0879254A1
Authority
EP
European Patent Office
Prior art keywords
polyols
alcohol
use according
mol
alcohols
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Withdrawn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
EP97902240A
Other languages
German (de)
English (en)
Inventor
Roland Grützmacher
Bernd Beuer
Andreas Heidbreder
Peter Döbrich
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0879254A1 publication Critical patent/EP0879254A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/04—Layered products comprising a layer of synthetic resin as impregnant, bonding, or embedding substance
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • C08G18/48—Polyethers
    • C08G18/4891—Polyethers modified with higher fatty oils or their acids or by resin acids
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups

Definitions

  • the invention relates to the production of polyurethane materials from storage-stable polyols and isocyanates.
  • the polyurethane materials according to the invention cure without bubbles even in a moist environment and have high mechanical strength.
  • Another advantage of the materials according to the invention is that the components required for production are stable in storage.
  • the inadequate material properties were generally taken into account by using castor oil mixed with polyether polyols as the polyol component. Although this process led to improved material properties in the polyurethanes formed after the reaction with isocyanates, at the same time the hydrophilicity of the polyol component was increased to such an extent that the materials released large amounts of CO 2 in a moist environment due to the reaction of the isocyanates with water, and thereby in particular There was a lot of blistering on the surface.
  • DE-OS 36 30 264 describes, for example, how the mechanical properties of polyurethanes from ring-opened, oleochemical polyols can be improved by first reacting the hydroxyl groups on the fatty acid residues of the polyols with alkylene oxides such as ethylene oxide or propylene oxide. Casting resins can thus be obtained whose mechanical properties are superior to those produced from castor oil.
  • the publication is silent about transesterification of the triglycerides with alkoxylated polyols.
  • US Pat. No. 3,424,766 teaches the production of so-called epoxidized urethane oils by first transesterifying epoxidized triglycerides with polyols having 2 to 6 hydroxyl groups in order to then convert them with polyisocyanates to give the epoxidized urethane oils.
  • the publication also mentions that the alcohols suitable for transesterification can be alkoxylated.
  • the publication does not indicate that triglycerides bearing hydroxyl groups, in particular castor oil, can also be transesterified with polyols and thus lead to improved polyurethane materials.
  • the unpublished patent application with the file number 195 29 406.8 describes the production of polyurethane prepolymers for use in one-component, moisture-curing foams or adhesives. Two-component (2-component) foams or casting resins are not mentioned. Although the transesterification of castor oil with low molecular weight polyols is mentioned here, the use of alkoxylated polyols for the transesterification is not disclosed. The oleochemical polyols are then immediately converted to polyurethane prepolymers. The attempt to store the polyols before the conversion to the polyurethane shows, surprisingly, that after a short time phase separation occurs which leads to the polyol being unusable. The use of the polyols in 2-component systems is therefore not possible
  • the invention therefore relates to the use of storage-stable ester polyols obtainable from
  • Storage stability in the sense of the present invention relates to the period in which the polyol can be stored at rest without the performance properties being impaired.
  • usage properties are understood to mean those properties which permit optimum handling of the polyol and after the reaction with Polyisocyanates lead to a material with at least approximately the same quality as before the storage of the polyol. If necessary, a storage stability of two weeks may be sufficient to achieve the desired purpose, but it will generally be advantageous to have longer storage stability, for example two to achieve or four months Ideally, the polyols according to the invention are stable over a period of at least twelve months
  • hydroxyl-bearing triglycerides are transesterified with polyols.
  • the hydroxyl-bearing triglycerides can be of either natural or synthetic origin.
  • unsaturated triglycerides can be epoxidized by persic acids and the oxiranes thus obtainable in acid or alkali-catalyzed ring-opening reactions with mono- or polyhydric alcohols convert to triglycerides bearing hydroxyl groups.
  • Unsaturated triglycerides of synthetic and / or natural origin come into consideration in an iodine number range from 30 to 150, preferably from 85 to 125
  • Typical examples of the group of unsaturated triglycerides are linseed oil, palmol, palm kernel oil, coconut oil, peanut oil, tea oil, olive oil, ohvenkernol, Babassuol, Meadowfoamol, Chaulmoograol, Ko ⁇ anderol, soybean oil, lardol, beef tallow, pork lard, Fischol, and sunflower oil and dermal oil and dermal oil and dermal oil new breed
  • the ring opening of such oxiranes is usually carried out with monofunctional or polyfunctional alcohols, but the use of monofunctional alcohols is preferred for the purposes of the invention.
  • Both the aliphatic and aromatic alcohols pay for the monofunctional alcohols, preference being given to the use of aliphatic alcohols.
  • the alcohols used can be branched or unbranched, saturated or unsaturated, but preference is given to using aliphatic, saturated alcohols, in particular methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, pentanol, hexanol, heptanol and the like higher homologues are used for ring opening.
  • fatty alcohols with 8 to 22 carbon atoms can also be used to open the ring.
  • Fatty alcohols are primary aliphatic alcohols of the formula (I)
  • R 1 represents an aliphatic, linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds
  • Typical examples are capron alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, my ⁇ styl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linoleol, alcohol alcohol, linoleol alcohol, linoleol alcohol, linoleol alcohol and brassidyl alcohol and their technical mixtures, which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols
  • the natural triglycerides with an OH function on the fatty acid residue such as cast
  • the alkoxylation products of polyfunctional, aliphatic alcohols are used according to the teaching of the invention.
  • the alcohols used for this generally have functionalities of 2 to 10, preferably 2 to 6.
  • These include in particular diols, e.g. 1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol or neopentyl glycol and polyols, such as e.g.
  • Trimethylolpropane, glycerin, trimethylolethane, pentaerythritol, sorbitol and / or oligomeric glycerols Trimethylolpropane, glycerin, trimethylolethane, pentaerythritol, sorbitol and / or oligomeric glycerols.
  • alkoxylated alcohols having 2 or 3 OH groups such as ethanediol, propanediol, glycerol, pentaerythritol, trimethylolpropane and / or trimethylolethane, is particularly preferred.
  • the alkoxylation can be carried out under conditions known per se with ethylene oxide (EO) and / or propylene oxide (PO), the use of PO or mixtures containing a predominant proportion of PO being preferred. Such mixtures should then contain more than 70, preferably more than 80 and particularly preferably more than 90% by weight of PO. Particularly good results are achieved with the exclusive use of PO for alkoxylation.
  • the polyols used according to the invention generally consist predominantly of alcohols with alkylene oxides, usually in a ratio of 0.1 to 20 moles per mole of OH functionality, with amounts of 0.5 to 8 or 0.8 to 2 moles being preferred , have been alkoxylated.
  • the use of the alkoxylation products of glycerol, in particular with about 3 mol PO, is particularly preferred according to the invention.
  • the alkoxylated polyols are then reacted with the triglycerides in a base-catalyzed transesterification reaction at temperatures between 120 and 250 ° C.
  • a base-catalyzed transesterification reaction at temperatures between 120 and 250 ° C.
  • the same catalysts are generally used as for the alkoxylation; in the optimal case, the catalyst used for the alkoxylation can also be used for the transesterification.
  • the use of basic lithium compounds such as lithium hydroxide, lithium carbonate, lithium acetate, lithium alkoxylates or the lithium salts of higher fatty acids has proven particularly useful here.
  • Lithium contents in particular of less than 100, preferably less than 70 and in particular less than 50 ppm have a positive effect on the storage stability of the polyols compared to higher or identical contents of other alkali metals.
  • the use of particularly small amounts of catalyst has proven to be particularly advantageous in that the catalyst does not have to be removed from the polyol mixture and does not adversely affect the conversion to the polyurethane and its resulting material properties.
  • the polyols which are most suitable for the purposes of the invention have no or only low contents, advantageously less than 1 ppm of alkali metals other than lithium, the lithium content advantageously being below 20 ppm.
  • the polyisocyanates are the second important building block for the polyurethane materials according to the invention.
  • Isocyanates react in a manner known to those skilled in the art with free hydroxyl groups in an addition reaction to form a urethane group.
  • Suitable isocyanate components according to the invention are generally all customary, polyfunctional aromatic and aliphatic isocyanates, such as, for example, also all oligomeric and polymeric isocyanate compounds as can be prepared from the oligomerization or cyclization of polyisocyanates under the influence of moisture or by reaction of polyfunctional alcohols with polyisocyanates.
  • the polyisocyanates can be used in excess and in deficit. examples for this are
  • Toluene diisocyanate (Desmodur L 67) (Bayer)
  • the isocyanates can be used both in pure form and in technical mixtures with or without solvents
  • the reaction between polyols and isocyanates usually takes place in a temperature range between 0 and 100 ° C., preferably between 5 and 50 ° C.
  • the components are usually first intensively mixed and then processed during the remaining pot life.
  • the mixing of the components can be carried out either by the user himself by stirring, whirling or other measures suitable for mixing, but the mixing can also be carried out by an automatic device, for example when removed from a pressurized can with separate compartments for polyol and isocyanate, the resulting mixture can be further processed into coatings, casting resins, foams or composite materials
  • the invention thus also relates to polyurethanes with the property that storage-stable ester polyols are obtainable through
  • At least one blowing agent and, if appropriate, a foam stabilizer are generally also necessary.
  • other additives can be added, for example solvents, flame retardants, Plasticizers, cell regulators, emulsifiers, fungicides, fillers, pigments and anti-aging agents
  • 1, 1,1,2-tetrafluoroethane, 1,1-difluoroethane and dimethyl ether are preferably used as blowing agents.
  • carbon dioxide, nitrous oxide, n-propane, n-butane and isobutane can also be used as blowing agents and chlorine-free fluorocarbons are advantageously used with boiling points from -40 to + 60 ° C propane / butane mixtures and dimethyl ether or mixtures thereof
  • the foam-forming composition can additionally contain stabilizers.
  • "Stabilizers” in the sense of this invention are, on the one hand, stabilizers which bring about a viscosity stability of the composition during production, storage or application.
  • monofunctional carboxylic acid chlorides, monofunctional highly reactive isocyanates, but also non- Corrosive inorganic acids are suitable.
  • Benzoyl chloride, toluenesulfonyl isocyanate, phosphoric acid or phosphorous acid may be mentioned as examples
  • stabilizers for the purposes of this invention are antioxidants, UV stabilizers or hydrolysis stabilizers.
  • the selection of these stabilizers depends, on the one hand, on the main components of the composition and, on the other hand, on the application conditions and the loads to be expected of the foam plastic.
  • the main antioxidants are usually , if necessary in combination with UV protection agents. Examples of these are the commercially available sterically hindered phenols and / or thioethers and / or substituted benzotriazoles or the sterically hindered amines of the HALS type ("hindered amine light stabilizer")
  • Hydrolysis stabilizers for example of the carbodhmide type, can optionally be used to stabilize the ester bonds
  • Another object of the invention is the use of the inventive.
  • Polyurethanes in composite materials and / or blends, where blends are homogeneous, Micro- or also macro-separated mixtures with other plastics are to be understood.
  • the polyurethanes in different mixture ratios with one or more additional components can be processed together to form a material with improved and / or new properties.
  • the fillers which mainly have a cost-reducing function
  • the additives mentioned below assume a functional task in the material, which is mainly associated with an improvement in the physical material properties.
  • the polyurethanes according to the invention are processed, for example, with natural or synthetic fibers, fiber short cuts, fabrics or the like.
  • Suitable materials are, for example, natural fibers such as silk, cotton, wool, jute, hemp, flax, sisal, straw or the like, but the secondary products of these fibers are just as suitable in their processed form m, for example as a fabric
  • the fibers can be incorporated into the polyurethanes according to the invention both in untreated and in treated form.
  • sizes based on siloxane or polyester, as are known to those skilled in the art for such surface treatments have proven to be suitable agents for surface treatment .
  • the resulting composite materials have excellent stability, tear resistance, abrasion resistance and toughness, as is required for many applications
  • synthetic fibers such as polyamide, polyester, polyether or carbon fibers
  • inorganic fibers such as glass fibers and glass fiber mats
  • the invention thus also relates to composite materials which can be produced from the storage-stable polyols according to the invention

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne l'utilisation de polyols d'ester stables au stockage pour la production de matériaux en polyuréthanne, lesdits polyols d'ester pouvant être obtenus par a) réaction d'alcools polyfonctionnels avec 0,5 à 60 moles d'oxyde d'éthylène (EO) et/ou d'oxyde de propylène (PO) par mole d'alcool et b) transestérification des polyols ainsi obtenus avec 0,1 à 30 moles de triglycérides par mole d'alcool alcoxylé, au moins un des restes d'acide gras comportant au moins un groupe OH par molécule de triglycéride, le mélange en comportant en moyenne au moins 1,5 par molécule.
EP97902240A 1996-02-06 1997-01-28 Materiaux en polyurethanne Withdrawn EP0879254A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19604177 1996-02-06
DE1996104177 DE19604177A1 (de) 1996-02-06 1996-02-06 Polyurethanwerkstoffe
PCT/EP1997/000363 WO1997029141A1 (fr) 1996-02-06 1997-01-28 Materiaux en polyurethanne

Publications (1)

Publication Number Publication Date
EP0879254A1 true EP0879254A1 (fr) 1998-11-25

Family

ID=7784599

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97902240A Withdrawn EP0879254A1 (fr) 1996-02-06 1997-01-28 Materiaux en polyurethanne

Country Status (4)

Country Link
EP (1) EP0879254A1 (fr)
JP (1) JP2000504750A (fr)
DE (1) DE19604177A1 (fr)
WO (1) WO1997029141A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1227895B1 (fr) * 1999-10-02 2004-11-24 E.I. Du Pont De Nemours And Company Procede de fabrication de vernissages bi-couches vernis de base/vernis clair et/ou de couches couvre-noeuds transparentes
KR20140007822A (ko) 2010-12-20 2014-01-20 바이엘 인텔렉쳐 프로퍼티 게엠베하 폴리에테르 에스테르 폴리올의 제조 방법
EP3161046B1 (fr) 2014-06-26 2026-03-25 Covestro Deutschland AG Composants composites à base de polyols hydrophobes
CN104311816A (zh) * 2014-11-11 2015-01-28 上海应用技术学院 一种以油菜秸秆为原料的聚醚多元醇的制备方法
CN113061242B (zh) * 2021-03-18 2023-10-27 金浦新材料股份有限公司 一种聚醚胺化合物、其制备方法及应用
EP4446353A1 (fr) 2023-04-14 2024-10-16 Covestro Deutschland AG Mousse de polyuréthane à stabilité dimensionnelle améliorée

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3177167A (en) * 1959-03-19 1965-04-06 Allied Chem Quick-drying urethane oil compositions
US2994674A (en) * 1959-08-07 1961-08-01 Atlas Powder Co Castor oil-based urethane coatings
US3332896A (en) * 1963-12-23 1967-07-25 Atlas Chem Ind Oil-modified polyurethanes
DE1745343A1 (de) * 1967-09-12 1971-09-09 Reichhold Albert Chemie Ag Verfahren zur Herstellung von wasserverduennbaren,oelmodifizierten Polyurethanharzen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9729141A1 *

Also Published As

Publication number Publication date
DE19604177A1 (de) 1997-08-07
WO1997029141A1 (fr) 1997-08-14
JP2000504750A (ja) 2000-04-18

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