WO2017054797A1 - Matière polymère molle réticulée par des isocyanates et produits associés - Google Patents

Matière polymère molle réticulée par des isocyanates et produits associés Download PDF

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Publication number
WO2017054797A1
WO2017054797A1 PCT/DE2016/100447 DE2016100447W WO2017054797A1 WO 2017054797 A1 WO2017054797 A1 WO 2017054797A1 DE 2016100447 W DE2016100447 W DE 2016100447W WO 2017054797 A1 WO2017054797 A1 WO 2017054797A1
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WO
WIPO (PCT)
Prior art keywords
isocyanate
crosslinked polymer
polymer material
material according
thiol
Prior art date
Application number
PCT/DE2016/100447
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German (de)
English (en)
Inventor
Matthias Ausmeier
Peter Gansen
Hans Hermann Dreyling
Frank Stefan Klingebiel
Original Assignee
Technogel Gmbh
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 Technogel Gmbh filed Critical Technogel Gmbh
Priority to EP16797716.4A priority Critical patent/EP3356437A1/fr
Publication of WO2017054797A1 publication Critical patent/WO2017054797A1/fr

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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
    • C08G18/52—Polythioethers
    • 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
    • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
    • C08G18/4676—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing sulfur
    • 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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5072—Polyethers having heteroatoms other than oxygen containing sulfur
    • 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
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6453—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having sulfur
    • 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
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic

Definitions

  • the invention relates to a soft, elastically deformable, 3-dimensionally isocyanate-crosslinked polymer material having an isocyanate index between 15 and 100, in particular a covalently crosslinked gel in the stationary phase, the material being formed from an isocyanate component and an isocyanate-reactive component and other additives and adjuvants, such as. B. in polyurethane chemistry known additives, catalysts, fillers and the like may contain, if desired or required. Both components may be uniform or mixed with respect to the functional substances.
  • the isocyanate component contains at least one at least difunctional isocyanate.
  • isocyanate also encompasses polymeric isocyanates or NCO prepolymers
  • the isocyanate-reactive component contains at least one at least difunctional isocyanate-reactive compound
  • the invention furthermore relates to products which are obtained using the material according to the invention and which consist of this material or in combination Contain with other materials or with other components.
  • the invention relates to the field of polyurethane chemistry in a broader sense.
  • the actual "polyurethanes" are polyaddition products of difunctional or polyfunctional alcohols and di- or polyfunctional isocyanates.
  • the polyurethanes can be varied in many ways. Suitable polyols include, inter alia, polyester, polyether, polycarbonate polyols and many other copolymeric compounds having free OH groups. There are also a variety of isocyanates. This leads to a large variety of products. Polyurethanes are used for i.a. used for hard and soft foams, for casting compounds, lacquers and adhesives. They can be represented as thermoplastics, elastomers, thermoplastic elastomers and thermosets. Polyurethanes are also available in a soft state with Shore (OOO) hardnesses below about 95 and in gelatinous consistency.
  • OOO Shore
  • the hetero analogs include the polyurea compounds including biurets and allophanates, the thionurethanes, thiolurethanes and dithiourethanes.
  • Thionethanes and thiolurethanes are also referred to as thiourethanes.
  • Thiolurethanes are used, for example, for highly transparent coatings and other coatings. They form electrically insulating thermosets with a high refractive index. Their use therefore relates to optical and electrical components and electrically insulating paints and castables, as described, inter alia, in EP 1 448 651 B1 and US 2009/0225425 A1.
  • WO 2014/180666 A1 describes polythiourethane casting resins or polythiourethane casting compounds for electronic or optical components and for optical lenses, which are distinguished by a high breaking strength with a relatively low specific weight and high refractive index. These materials are crystal clear hard thermosets with good heat resistance.
  • the isocyanate-reactive component contains for this purpose oligothioether dithiols with molecular weights up to 426. Further short-chain, branched and cyclic thiols may be added. All these materials are unsuitable for soft, elastically deformable materials.
  • EP 0 057 838 B1, EP 0 057 839 B1 and EP 0 51 1 570 B1 disclose elastically deformable and soft polyurethane gels and describe their basic structure.
  • the gel character manifests itself, inter alia, in a 3-dimensional mobility within the material under pressure, similar to a flow, the reacted gel nevertheless returns to its original shape after elimination of the strain (elasticity).
  • the gels are therefore particularly suitable for upholstery.
  • polyols are used as isocyanate-reactive compounds and used in a superstoichiometric manner so that some of the polyol in the polyurethane network is relatively freely mobile and acts like a liquid phase as a disperse gel phase in a stationary gel phase from the polyurethane network.
  • new polymer gels are to be found in which a covalent polymer network forms the stationary phase and the dispersion medium is firmly bound, so that in the material a good three-dimensional pressure distribution can be carried out with good resilience.
  • These gels are furthermore to be designed in such a way that they have a good appearance and feel for products made from them, with at best low tack, it being possible for them to be used as uncoated, uncovered material.
  • it is intended to be able to obtain from the material upholstery having good haptic properties, which are similar in their mechanical properties to known soft, elastically deformable polyurethanes.
  • a soft, elastic deformable isocyanate-crosslinked polymer material having an isocyanate number between 1 5 and 100 provided, in particular a gel covalently crosslinked in the stationary phase.
  • at least one long-chain at least difunctional thiol having an average molecular weight of at least 1200 is used as the isocyanate-reactive component or as a mixture within this component.
  • the material according to the invention is basically crosslinked. Both the isocyanate and the isocyanate-reactive compound which form the elastomer are at least difunctional, with a reaction partner having a higher functionality with a reactive functionality of from 2.1. If a mixture of several isocyanates or more isocyanate-reactive compounds is used, the average (total) functionality should refer to the weighted average of the individual functionalities. Accordingly, 50% by weight of an isocyanate-reactive compound having the functionality 3 and 50% by weight of an isocyanate-reactive compound having the functionality 6 would result in the mean functionality 4.5 within a mixed isocyanate-reactive component. The same applies to mixed isocyanates.
  • the components each contain one or more of the reactive species of the component type and, optionally, additives, processing aids, one or more catalysts and, if necessary, solvents.
  • the additives include fillers, reaction accelerators, reaction retarders, UV protectants, flame retardants, additives to increase the thermal or electrical conductivity, hydrophobizing additives, dyes and pigments.
  • the processing aids include, among other mold release agents, as far as the mass added, adhesion promoters and emulsifiers. Immediately before processing - before the start of the reaction - often only the two components are mixed. This can be z. For example, with a commercially available 2-component mixing and dosing, as known for polyurethane processing.
  • Prepolymers can also be used in particular in the isocyanate component.
  • An isocyanate prepolymer is an intermediate, namely a polyaddition product of at least one isocyanate-reactive compound and the isocyanate or isocyanates in which terminal NCO groups are present.
  • This intermediate referred to as prepolymer, is then further reacted with the same isocyanate-reactive compound or mixture to obtain the final product, or further reacted with another isocyanate-reactive compound or component. It is likewise possible to use prepolymers of the isocyanate-reactive component which are correspondingly stopped polyaddition products with isocyanate-reactive groups.
  • prepolymers improves the homogeneity in the last stage of the process and even out the material quality.
  • the advantages of prepolymers are u.a. in "Polyurethane Handbook", 2nd Edition, Günter Oertel (Ed.), Carl Hanser Verlag, Kunststoff, 1994, in Chapter 3.3. "Conversion Products of Raw Materials", pp. 84-97, in particular under 3.3.2.4. "Polyisocyanates Prepolymers, p. 92.
  • the isocyanate-reactive component contains at least one long-chain, at least difunctional, thiol having an average molecular weight of at least 1000.
  • the average molecular weight is at least 1200 or more preferably at least 1300.
  • the molecular weights are as those of usually indicated to the manufacturers of the substances. In the case of high molecular weight substances with molecular weight distribution are weight average.
  • the mathematical product of the average NCO functionality and the average functionality of the isocyanate-reactive component is at least 4.2. More preferably 5.2, in particular at least 6 and in particular embodiments at least 24th
  • the product of the functionalities can furthermore preferably be less than or equal to 32.
  • This mathematical product characterizes important properties of the crosslinking structure, such as i.a. in EP 0 057 838 A1. Accordingly, for a reaction product of a mixed isocyanate-reactive component with functionalities 3 and 6, as exemplified above (50:50) and a diisocyanate, a mathematical product of average functionality of 9 (4.5 x 2) would result.
  • the SH functionality of the thiols is 2 to 8, preferably 3 to 6.
  • the isocyanate functionality (NCO functionality) is preferably 2 to 6, more preferably 2 to 4.
  • the long-chain thiols according to the invention having molecular weights from 1200 g / mol preferably polymeric thiols, in which the chain structure results from the polymerization, polycondensation or other formation reaction of their preparation.
  • the long-chain thiols of this invention also include branched compounds containing at least one, preferably a terminal SH-functionalized chain.
  • the long-chain thiol is selected from the group of polyether thiols, polyester thiols, polyetherester thiols, polythioether thiols, and mixed poly (ether thioether) thiols, wherein the thiols include at least difunctional compounds dithiols and polythiols.
  • the long-chain, two or more SH-functionalized compounds which are preferably used as isocyanate-reactive compounds according to this invention include, in particular, polyethers (di- or poly) thiols, for example obtainable by alkoxylation of di- or multifunctional initiators, such as ethyl - Glycol (functionality 2), 1, 1, 1 -Trimethylolpropan (TMP) (Fkt.3), pentaerythritol (Fkt. 4) or dipentaerythritol (Fkt. 6), and further reaction with thiirane (ethylene sulfide, ES).
  • Preferred alkylene oxides are butylene oxide, propylene oxide, and ethylene oxide, more preferably PO / EO (with ES tip).
  • Polyether ester thiols which can be obtained by esterification of polyether polyols with omega-mercaptocarboxylic acids, are also included in this group.
  • the long-chain thiols according to the invention include long-chain, at least twice SH-functionalized polyesters, in particular polyesters esterified terminally with omega-mercaptocarboxylic acid and polyester polyols.
  • SH-functionalized polycaprolactone polyols from PCL Polyols obtained PCL (di- or poly) thiols).
  • polystyrene resin in general, a wide variety of polyols, polyether polyols, polyester polyols or polythioether polyols and, for example, poly (ether thioether) polyols obtainable by condensation of thioglycol with omega-mercaptocarboxylic acids can be converted into polymeric di- or polyhydric thiols which are basically all used in this invention can.
  • Suitable polyether polyols, polyester polyols and polyether polyester polyols are known from polyurethane chemistry and therefore need not be described separately here.
  • long-chain thiols according to the invention include long-chain, in particular linear thioetherthiols of the form
  • the isocyanate-reactive component contains at least 30% by weight of a uniform thiol or a mixture of a plurality of thiols.
  • the largest part by weight should consist of the long-chain thiols according to the invention with MW> 1000.
  • the isocyanate-reactive component contains, in addition to the long-chain thiol according to the invention, OH-functional compounds, in particular polyols.
  • the isocyanate-reactive component preferably comprises, in addition to the thiol, at least one polyether polyol and / or one polyester polyol, as are well known from polyurethane chemistry.
  • a polyol present in the isocyanate-reactive component for the polymer material according to the invention preferably has an OH number of not more than 150 mg KOH / g, more preferably not more than 120 and more preferably not more than 80.
  • the isocyanate index (also isocyanate index) of the polymer material, namely the hetero-analogous polyurethane material is between 15 and 100.
  • the isocyanate-reactive groups are in each case in excess relative to the isocyanate groups.
  • the isocyanate index is between 15 and 90 and for particularly soft, elastically deformable materials and gels between 15 and 75.
  • the isocyanate may in principle be a di- or a polyisocyanate, preferably having a functionality of from 2 to 6.
  • the isocyanate is a diisocyanate, in particular an aliphatic or an aromatic diisocyanate (eg HDI, TDI, MDI and IPDI) ,
  • the isocyanate is an NCO prepolymer and especially a polyether NCO prepolymer. Preference is given to using difunctional NCO-HDI prepolymers.
  • the hetero-analogous polyurethane material of this invention may contain additives (adjuvants and additives) as known in polyurethane chemistry. These additives can be used here accordingly.
  • additives adjuvants and additives
  • An overview of the various additives is given by Oertel, a.a. O., p. 98 - 1 17, "3.4. Additives and Auxilliary Materials ".
  • At least one filler selected from the group of expanded and expandable polymeric hollow microspheres and pyrogenic metal oxides.
  • Pyrogenic, highly dispersed silicon dioxide eg Aerosil®
  • pyrogenic metal oxide is preferred as pyrogenic metal oxide.
  • Suitable processes for the preparation of the materials according to the invention generally include the combination of the isocyanate-reactive compounds described above in detail or the isocyanate-reactive component with the isocyanate or the isocyanates or the isocyanate component by means of a customary manufacturing process known from polyurethane chemistry.
  • the invention further encompasses products obtained using the "hetero-analogous polyurethane material" of the invention and consisting of this material or containing it in combination with other materials or with other components.
  • Particularly preferred products in the context of this invention are upholstery of any kind, for.
  • upholstery of any kind for.
  • Characteristic of the products according to the invention is in each case a layer, layer or a three-dimensionally shaped element of the soft, elastically deformable, three-dimensionally isocyanate-crosslinked polymer material according to the invention, the soft hetero-analogous polyurethane elastomer.
  • This preferably forms a deformable elastic body, which with components of other materials, for.
  • supports to be padded hard components, but also with other soft materials such as foams, natural cushioning materials and the like may be connected.
  • Sandwich constructions are just as possible as a composite of several moldings.
  • the material according to the invention can be sprayed or cast for the production of various products, shaped by a nozzle, by a
  • PCL polyol a pentaerythritol started, medium long-chain, branched polycaprolactone polyol
  • PCL polyol a pentaerythritol started, medium long-chain, branched polycaprolactone polyol
  • Viscosity approx. 4000 mPa s (23 ° C)
  • isocyanureactive components were reacted with the same isocyanate.
  • the catalyzed isocyanate-reactive substance was homogenized using commercially available 2-component low-pressure mixing plant with the polyisocyanate.
  • An Eldomix 603 from the manufacturer Hilger & Kern was used.
  • the media was conveyed by gear pumps.
  • the mixing was carried out with a static dynamic mixing tube 1 3-12 (rotary mixer, bells connection, 12 mixing elements, inner diameter: 12.5 mm, length 198 mm).
  • the catalyst used was Dabco® 33-LV from the manufacturer Air Products & Chemicals Inc.
  • the variation of the hardness of the polymer material was realized by varying the mixing ratio of isocyanate-reactive component and polyisocyanate.
  • isocyanate-reactive component and polyisocyanate.
  • PE film / thickness 100 microns
  • the tack of the material was determined by means of a standardized peel strength test.
  • the peel strength provides information about the specific adhesion or also "adhesion".
  • the force is measured in Newton, which is required to peel off a test strip of the material to be tested from a planar substrate. The removal takes place with a force acting parallel to the substrate, which acts on the folded-out test strip. The result value is related to the test specimen width in mm and is given in "N / 25mm". Testing of the peel strength according to DIN 1939
  • Substrate Polished chromium-nickel steel with 17% Cr and 8% Ni
  • Thiol gels according to the invention are to be compared with polyol gels known from the prior art.
  • SH gels and OH gels with structurally similar structure as possible were used.
  • polyester polyol gels were compared with polyesterpolythiol gels, namely gels of the invention according to composition examples 3 and 4 with OH gels according to composition examples 1 and 2, wherein both gel types were further varied according to the information to Table 1 in their hardness with additional intermediate examples.
  • OH-functional Capa 4101 (gravimetric mixing ratios for setting the degrees of hardness: 100: 52 to 100: 61)
  • Soft polyurethane gels with Shore (OOO) hardnesses between about 8 and 95 are Particularly suitable for cushioning elements, but show a significant tack or high peel strength values, which are usually undesirable and complicate the use in upholstery. This tackiness decreases towards higher hardness and higher isocyanate ratios.

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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)

Abstract

Pour une matière polymère molle, réticulée de manière tridimensionnelle par des isocyanates, déformable élastiquement, dont l'indice d'isocyanate est compris entre 15 et 100, en particulier pour un gel réticulé de façon covalente dans la phase stationnaire, on utilise comme composant réactif à l'isocyanate ou en mélange à l'intérieur de ce composant au moins un thiol au moins difonctionnel à longue chaîne dont le poids moléculaire moyen est d'au moins 1 200. La matière contient des motifs de réticulation thioluréthane du type -NH-(C=0)-S-. L'utilisation de thiols à chaîne longue au lieu de polyols permet d'obtenir une adhésivité nettement plus faible et des variantes d'autres propriétés des produits et de pouvoir se passer du gainage de la matière molle ou en forme de gel avec des films ou des couches de revêtement ou d'enveloppe. L'invention concerne en outre des produits qui sont obtenus à l'aide de la matière polyuréthane hétéro-analogue de l'invention et qui sont constitués de cette matière ou qui contiennent celle-ci en combinaison avec d'autres matières ou avec des constituants supplémentaires.
PCT/DE2016/100447 2015-10-01 2016-09-26 Matière polymère molle réticulée par des isocyanates et produits associés WO2017054797A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP16797716.4A EP3356437A1 (fr) 2015-10-01 2016-09-26 Matière polymère molle réticulée par des isocyanates et produits associés

Applications Claiming Priority (2)

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DE102015012660.1 2015-10-01
DE102015012660.1A DE102015012660A1 (de) 2015-10-01 2015-10-01 Weicher isocyanatvernetzter Polymerwerkstoff und zugehörige Erzeugnisse

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WO2017054797A1 true WO2017054797A1 (fr) 2017-04-06

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DE (1) DE102015012660A1 (fr)
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3450899A1 (fr) * 2017-09-05 2019-03-06 TechnoGel GmbH Rembourrage de magasin d'arme à feu
CN111876097A (zh) * 2020-07-03 2020-11-03 江门市长河化工实业集团有限公司 一种预制型的聚氨酯运动地胶及其制备方法
CN114058314A (zh) * 2021-12-19 2022-02-18 北京大学 一种聚硫氨酯胶黏剂的制备方法

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EP0057838A1 (fr) 1981-02-03 1982-08-18 Bayer Ag Gels, procédé pour leur fabrication et leur utilisation
EP0057839B1 (fr) 1981-02-03 1985-08-28 Bayer Ag Gels sur la base d'une matrice de polyuréthane et de polyols de haut poids moléculaire, contenant, le cas échéant, des substances actives, un procédé pour leur fabrication ainsi que leur utilisation
EP0511570B1 (fr) 1991-05-01 1997-03-12 Bayer Ag Gels, leur préparation et leur utilisation
US20060167167A1 (en) * 2002-07-24 2006-07-27 Toray Fine Chemicals Co., Ltd A Corporation Of Japan A curing composition comprising a polymer having two or more thiol groups per molecule, a compound having two or more isocyanate groups per molecule, carbon black and silicic acid or silicate filler, and/or a pulverized coal filler.
EP1448651B1 (fr) 2001-11-16 2008-04-30 PPG Industries Ohio, Inc. Polysulfures de poly(urethanne uree) hautement resistants
US20090225425A1 (en) 2006-09-06 2009-09-10 Shin Dae Specialties Co., Ltd. Optical resin composition having excellent impact resistance and method for fabricating optical lens using the same
US20110092639A1 (en) * 2007-05-01 2011-04-21 Prc-Desoto International, Inc. Compositions Including a Polythioether
US20130230336A1 (en) * 2012-03-05 2013-09-05 Fuji Xerox Co., Ltd. Roll member, charging device, image forming apparatus, and process cartridge
WO2014180666A1 (fr) 2013-05-07 2014-11-13 Bruno Bock Chemische Fabrik Gmbh & Co. Kg Résine moulée à base de polythio-uréthane présentant une résistance élevée à la rupture et un faible poids spécifique

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0057838A1 (fr) 1981-02-03 1982-08-18 Bayer Ag Gels, procédé pour leur fabrication et leur utilisation
EP0057838B1 (fr) 1981-02-03 1985-03-27 Bayer Ag Gels, procédé pour leur fabrication et leur utilisation
EP0057839B1 (fr) 1981-02-03 1985-08-28 Bayer Ag Gels sur la base d'une matrice de polyuréthane et de polyols de haut poids moléculaire, contenant, le cas échéant, des substances actives, un procédé pour leur fabrication ainsi que leur utilisation
EP0511570B1 (fr) 1991-05-01 1997-03-12 Bayer Ag Gels, leur préparation et leur utilisation
EP1448651B1 (fr) 2001-11-16 2008-04-30 PPG Industries Ohio, Inc. Polysulfures de poly(urethanne uree) hautement resistants
US20060167167A1 (en) * 2002-07-24 2006-07-27 Toray Fine Chemicals Co., Ltd A Corporation Of Japan A curing composition comprising a polymer having two or more thiol groups per molecule, a compound having two or more isocyanate groups per molecule, carbon black and silicic acid or silicate filler, and/or a pulverized coal filler.
US20090225425A1 (en) 2006-09-06 2009-09-10 Shin Dae Specialties Co., Ltd. Optical resin composition having excellent impact resistance and method for fabricating optical lens using the same
US20110092639A1 (en) * 2007-05-01 2011-04-21 Prc-Desoto International, Inc. Compositions Including a Polythioether
US20130230336A1 (en) * 2012-03-05 2013-09-05 Fuji Xerox Co., Ltd. Roll member, charging device, image forming apparatus, and process cartridge
WO2014180666A1 (fr) 2013-05-07 2014-11-13 Bruno Bock Chemische Fabrik Gmbh & Co. Kg Résine moulée à base de polythio-uréthane présentant une résistance élevée à la rupture et un faible poids spécifique

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Title
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"Polyurethane Hand-book", 1994, CARL HANSER VERLAG, article "Konversion.Products of Raw Materials", pages: 84 - 97

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3450899A1 (fr) * 2017-09-05 2019-03-06 TechnoGel GmbH Rembourrage de magasin d'arme à feu
CN111876097A (zh) * 2020-07-03 2020-11-03 江门市长河化工实业集团有限公司 一种预制型的聚氨酯运动地胶及其制备方法
CN114058314A (zh) * 2021-12-19 2022-02-18 北京大学 一种聚硫氨酯胶黏剂的制备方法

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