EP0000381B1 - Verfahren zur Herstellung von seitenständige Hydroxylgruppen aufweisenden Isocyanat-Polyadditionsprodukten und die nach diesem Verfahren erhaltenen Produkte. - Google Patents

Verfahren zur Herstellung von seitenständige Hydroxylgruppen aufweisenden Isocyanat-Polyadditionsprodukten und die nach diesem Verfahren erhaltenen Produkte. Download PDF

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Publication number
EP0000381B1
EP0000381B1 EP78100323A EP78100323A EP0000381B1 EP 0000381 B1 EP0000381 B1 EP 0000381B1 EP 78100323 A EP78100323 A EP 78100323A EP 78100323 A EP78100323 A EP 78100323A EP 0000381 B1 EP0000381 B1 EP 0000381B1
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EP
European Patent Office
Prior art keywords
groups
water
parts
oxazolidine
prepolymers
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.)
Expired
Application number
EP78100323A
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German (de)
English (en)
French (fr)
Other versions
EP0000381A1 (de
Inventor
Klaus Dr. Noll
Klaus Dr. Nachtkamp
Josef Dr. Pedain
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Bayer AG
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Bayer AG
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Filing date
Publication date
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Publication of EP0000381A1 publication Critical patent/EP0000381A1/de
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Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/904—Isocyanate polymer having stated hydrophilic or hydrophobic property

Definitions

  • the present invention relates to a new process for the preparation of new isocyanate polyaddition products having pendant hydroxyl groups and to the compounds obtainable by this process.
  • the process according to the invention is based on the principle of reacting reactive systems containing isocyanate groups and oxazolidine groups with water, the chain extension reaction taking place essentially with the formation of urea groups from the isocyanate groups and the amino groups hydrolytically released from the oxazolidines, while the hydrolytic cleavage of the oxazolidine groups also takes place comparatively inert hydroxyl groups do not participate in the reaction and are present laterally in the process products.
  • compositions of these publications are generally systems which are stable in the absence of moisture and have oxazolidines and isocyanates which, under the influence of atmospheric moisture, i.e. react under the influence of traces of water to form high-molecular, cross-linked structures.
  • the present invention in particular also relates to an embodiment of this method in which prepolymers which are hydrophilically modified and / or contain an external emulsifier and a preponderant excess of water with respect to the chain extension reaction are used, so that an aqueous dispersion or solution of the polyadducts is obtained directly.
  • the process according to the invention for the first time opens up a possibility of producing predominantly linear polyurethanes which are therefore soluble in common solvents and which have pendant hydroxyl groups and are therefore accessible to a subsequent crosslinking reaction, for example with organic polyisocyanates. Because of their linear structure, the process products according to the invention can be converted without difficulty into aqueous dispersions or solutions, with the simultaneous incorporation of hydrophilic groups and / or with the use of external emulsifiers, from which it is then also possible to subsequently produce simply crosslinkable fabrics.
  • Starting materials for the process according to the invention are essentially linear prepolymers which have a statistical average of 1.8 to 2.2, preferably 2, terminal isocyanate groups and which generally have an average molecular weight of 500 to 10,000, preferably 800 to 4,000.
  • the NCO prepolymers are prepared by known methods of polyurethane chemistry by reacting excess amounts of organic polyisocyanates, preferably diisocyanates, with suitable, preferably difunctional, compounds having groups which are reactive toward isocyanate groups. Starting materials for the preparation of the NCO prepolymers are accordingly.
  • any organic polyisocyanates preferably diisocyanates of the formula wherein Q represents an aliphatic hydrocarbon group having 4 to 12 carbon atoms, a cycloaliphatic hydrocarbon group having 6 to 15 carbon atoms, an aromatic hydrocarbon group having 6 to 15 carbon atoms or an araliphatic hydrocarbon group having 7 to 15 carbon atoms.
  • Q represents an aliphatic hydrocarbon group having 4 to 12 carbon atoms, a cycloaliphatic hydrocarbon group having 6 to 15 carbon atoms, an aromatic hydrocarbon group having 6 to 15 carbon atoms or an araliphatic hydrocarbon group having 7 to 15 carbon atoms.
  • Examples of such preferred diisocyanates are Tetramethylene diisocyanate, hexamethylene diisocyanate, dodecamethylene diisocyanate.
  • 1,4 - diisocyanato - cyclohexane 1 - isocyanato - 3,3,5 - trimethyl - 5 - isocyanatomethylcyclohexane, 4,4 '- diisocyanatodicyclohexylmethane, 4,4' - dilsocyanato - dicyclohexylpropane - (2,2), 1,4 - diisocyanatobenzene, 2,4 - diisocyanatotoluene, 2,6 - diisocyanatotoluene, 4,4 '- diisocyanatodiphenylmethane, 4,4' - diisocyanato - diphenylpropane - (2,2), p - xylylene - diisocyanate or ⁇ , a, a ', ⁇ '- Tetramethyl - m - or p - xylylene diisocyanate
  • polyfunctional polyisocyanates known per se in polyurethane chemistry, or else modified polyisocyanates containing, for example, carbodiimide groups, allophanate groups, isocyanurate groups, urethane groups and / or biuret groups.
  • Any organic compounds with at least two groups that are reactive toward isocyanate groups in particular a total of two amino groups, thiol groups, carboxyl groups and / or hydroxyl-containing organic compounds of the molecular weight range 62-10,000, preferably 1,000 to 6,000.
  • the corresponding dihydroxy compounds are preferably used.
  • tri-functional or higher-functional compounds in the sense of the isocyanate polyaddition reaction in small proportions to achieve a certain degree of branching is possible, as is the possible use of tri- or higher-functional polyisocyanates already mentioned for the same purpose.
  • the polyethers which are preferred according to the invention and preferably have two hydroxyl groups are those of the type known per se and are, for example, polymerized by themselves with epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin, for example in the presence of BF 3 , or by addition of these epoxides, optionally in a mixture or in succession, to starting components with reactive hydrogen atoms such as alcohols and amines, for example water, ethylene glycol, propylene glycol - (1,3) or - (1,2), 4,4 '- dihydroxy-diphenylpropane, Aniline.
  • epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin
  • reactive hydrogen atoms such as alcohols and amines
  • Polyethers modified by vinyl polymers e.g. by polymerization of styrene or acrylonitrile in the presence of polyethers (American patents 3,383,351, 3,304,273, 3,523,093, 3,110,695, German patent 1,152,536) are also suitable.
  • the proportionally higher-functionality polyethers to be used, if appropriate, are formed in an analogous manner by known alkoxylation of higher-functionality starter molecules, e.g. Ammonia, ethanolamine, ethylenediamine or sucrose.
  • the condensation products of thiodiglycol with itself and / or with other glycols, dicarboxylic acids, formaldehyde, aminocarboxylic acids or amino alcohols should be mentioned in particular.
  • the products are polythio ether, polythio ether ester, polythio ether ester amide.
  • polyacetals e.g. the compounds which can be prepared from glycols, such as diethylene glycol, triethylene glycol, 4,4'-diethoxy-diphenyldimethylmethane, hexanediol and formaldehyde.
  • glycols such as diethylene glycol, triethylene glycol, 4,4'-diethoxy-diphenyldimethylmethane, hexanediol and formaldehyde.
  • Polyacetals suitable according to the invention can also be prepared by polymerizing cyclic acetals.
  • Suitable polycarbonates containing hydroxyl groups are those of the type known per se. which, for example, by reacting diols such as propanediol - (1,3), butanediol - (1,4) and / or Hexanediol - (1,6), diethylene glycol, triethylene glycol, tetraethylene glycol with diaryl carbonates, for example diphenyl carbonate, or phosgene, can be prepared.
  • diols such as propanediol - (1,3), butanediol - (1,4) and / or Hexanediol - (1,6)
  • diethylene glycol triethylene glycol
  • tetraethylene glycol for example diphenyl carbonate, or phosgene
  • polyester amides and polyamides include e.g. the predominantly linear condensates obtained from polyvalent saturated and unsaturated carboxylic acids or their anhydrides and polyvalent saturated and unsaturated amino alcohols, diamines, polyamines and their mixtures. Polyhydroxyl compounds already containing urethane or urea groups can also be used.
  • Low molecular weight polyols can also be used, e.g. Ethanediol, 1,2-and 1,3-propanediol, 1,4-and 1,3-butanediol, pentanediols, hexanediols, trimethylolpropane, hexanetriols, glycerol and pentaerythritol.
  • hydrophilically modified prepolymers are to be used, they are produced by known processes of the prior art, for example in accordance with DT-OSs 1 495 745, 1 495 847, 2 446 440, 2 340 ⁇ 512, US Pat 310, GB-PS'en 1 158 088 or 1 076 688 described methods.
  • references related to the preparation of aqueous polyurethane dispersions or solutions i.e. for example, diisocyanates, diamines or dihydroxy compounds or diisocyanates or glycols containing ionic or potential ionic groups or polyethylene oxide units can also be used.
  • the preferred hydrophilically modified structural components include in particular the sulfonate group-containing aliphatic diols according to DE-A 2 446 440, the cationic or also anionic internal emulsifiers which can be incorporated according to German patent application P 26 51 506.0 and also the monofunctional incorporable polyethers described in this patent application.
  • the reactants are generally used in such proportions that a ratio of isocyanate groups to hydrogen atoms reactive towards NCO, preferably from hydroxyl groups, from 1.05 to 10, preferably from 1.1 to 3 correspond.
  • the order in which the individual reactants are added is largely arbitrary. You can either mix the hydroxyl compounds and add the polyisocyanate, or you can gradually add the mixture of hydroxyl compounds or the individual hydroxyl compounds to the polyisocyanate component.
  • the NCO prepolymers are preferably produced in the melt at 30 to 190 ° C., preferably at 50 to 120 ° C.
  • the prepolymers could of course also be produced in the presence of organic solvents.
  • Suitable solvents e.g. in an amount up to 25% by weight, based on the solid, could be used e.g. Acetone, methyl ethyl ketone, ethyl acetate, dimethylformamide or cyclohexanone.
  • NCO prepolymers in the process according to the invention, in the production of which none of the hydrophilic structural components mentioned have been used, in which the content of the groups mentioned above under b) or c) is therefore 0.
  • ionic emulsifiers such as alkali and ammonium salts of long-chain fatty acids or long-chain aryl (alkyl) sulfonic acids are suitable, as are nonionic emulsifiers such as ethoxylated alkylbenzenes with an average molecular weight of 500 to 10,000.
  • These external emulsifiers are thoroughly mixed with the NCO prepolymers before the process according to the invention is carried out. They are generally used in amounts of 1 to 30, preferably 5 to 20,% by weight, based on the weight of the NCO prepolymer. It is also possible to increase the hydrophilicity of the hydrophilic modified NCO prepolymers by using such external emulsifiers, although this is generally not necessary.
  • the reactants are preferably used in proportions such that 0.37-0.53, preferably 0.4-0.51 mol, hydroxyl groups of the hydroxyoxyzolidine are present in each mole of isocyanate groups in the NCO prepolymer.
  • Reaction mixtures are obtained on these which have about 0.6-1.1, preferably about 0.65-1.05, oxazoline groups per remaining isocyanate group. Since the monohydroxyoxazolidines are monofunctional compounds, there is no appreciable increase in molecular size in this reaction.
  • the reaction products like the NCO prepolymers used as starting materials, are therefore essentially linear compounds.
  • hydroxyoxazolidines and the bisoxazolidines mentioned are compounds known from the literature (see, for example, the references mentioned at the beginning with regard to the moisture-curing oxazolidine compositions of the prior art).
  • Bisoxazolidines or hydroxyoxazolidines to be used with particular preference are the corresponding compounds mentioned in US Pat. No. 4,002,601 and DE-A 2,446,438.
  • Bis- (2-hydroxyethyl) amine and bis- (2-hydroxypropyl) amine are particularly suitable. In principle, however, bis- (2-hydroxybutyt) amine, bis- (2-hydroxyhexyl) amine, bis- (3-hydroxyhexyl) amine, or N- (2-hydroxypropyl) -N- ( 6-hydroxyhexyl) amine.
  • the bisoxazolidines to be used according to the invention can be reacted with diisocyanates of the formula (in which Z has the meaning given above), for example hexamethylene diisocyanate.
  • diisocyanates of the formula (in which Z has the meaning given above)
  • Z has the meaning given above
  • diisocyanates of the formula (in which Z has the meaning given above) for example hexamethylene diisocyanate.
  • IPDI 3,3,5-trimethyl-5-isocyanatomethyl-cyclohexyl isocyanate
  • 4'-diisocyanatodicyclohexyl methane 2,4- and 2,6-diisocyanatotoluene or 4,4'-diisocyanatodiphenytmethane.
  • dicarboxylic acids, aliphatic, cycloaliphatic or aromatic in nature of the formula leads to bisoxazolidines containing ester groups which can be used according to the invention.
  • a decisive advantage over the previously known methods of the prior art for the solvent-free or low-solvent production of aqueous polyurethane dispersions is that an intimate mixing with the chain extender takes place even before being brought together with water, or chemical fixation even before being brought together with water the chain-extending group (oxazolidine group) takes place, so that the chain extension leads to particularly homogeneous products.
  • the process according to the invention is particularly suitable for the production of aqueous dispersions or solutions, which have a solids content of 10 to 70, preferably 30 to 65 wt .-%.
  • the particles of the discontinuous phase in the dispersions generally have a diameter of 50 to 1000 nm.
  • the preparation of sols with an average particle diameter of the discontinuous phase of about 1-50 nm or clear, aqueous solutions in which the solid is present in molecularly disperse form or at most in the form of associates is also possible according to the invention.
  • solutions or dispersions of the polyurethanes in water are obtained in the process according to the invention depends above all on the molecular weight and the hydrophilicity of the dissolved or dispersed particles, which in turn depends on the suitable choice of type and quantitative ratio of the starting materials, in particular in the preparation of the NCO prepolymers , can be adjusted according to the known principles of polyurethane chemistry.
  • the use of an NCO prepolymer with a mean NCO functionality slightly below 2 leads to the polyaddition reaction being terminated before excessively high molecular weights are reached.
  • the polyurethanes produced by the process according to the invention and present in aqueous dispersion or solution are on a par with the known polyurethanes produced in organic solvents. Films made from them have excellent mechanical strength and hydrolysis resistance and can be used for a wide variety of applications.
  • pendant hydroxyl groups incorporated in the process products according to the invention can be crosslinked after shaping, for example by evaporation of the solvent or water after a chemically or thermally activatable crosslinking agent has been added to the solution or the dispersion.
  • Suitable crosslinking agents are e.g. Polyisocyanates with blocked isocyanate groups or melamine resins which are reactive towards hydroxyl groups. Even if the process products according to the invention are not chemically crosslinked via the pendant hydroxyl groups, these can be advantageous since they often increase the physical affinity of the process products according to the invention for substrates which are coated with the compounds according to the invention.
  • the film was not sticky after moistening with toluene and acetone and did not dissolve in hot DMF.
  • the NCO prepolymer from Example 1 was at 60 ° C with 361.8 parts of a bisoxazolidine of the formula transferred. 5100 parts of deionized water were added with vigorous stirring. The resulting one Dispersion had a solids content of 30% and a viscosity of 18 seconds (Ford cup, 4 mm). It showed a Tyndall effect in the translucent light.
  • the dispersion dries to a clear, colorless and tack-free film which, after the water has been completely removed, has a Shore A hardness of 78. After heating to 130 ° C. for 20 minutes, the hardness had risen to 85 (Shore-A) and the film was only swellable in hot DMF, but no longer soluble.
  • the resulting aqueous dispersion had a solids content of 30% and a viscosity of 15 seconds (Ford cup, 4 mm).
  • the dispersion showed a Tyndall effect in the translucent light.
  • the dispersion After pouring, the dispersion dried into a clear, hard film, which was easy to scratch with a fingernail.
  • the pencil hardness was HB-H. After heating at 130 ° C. for 20 minutes, the temperature had risen to 3 hours.

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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)
EP78100323A 1977-07-15 1978-07-07 Verfahren zur Herstellung von seitenständige Hydroxylgruppen aufweisenden Isocyanat-Polyadditionsprodukten und die nach diesem Verfahren erhaltenen Produkte. Expired EP0000381B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772732131 DE2732131A1 (de) 1977-07-15 1977-07-15 Verfahren zur herstellung von seitenstaendige hydroxylgruppen aufweisenden isocyanat-polyadditionsprodukten
DE2732131 1977-07-15

Publications (2)

Publication Number Publication Date
EP0000381A1 EP0000381A1 (de) 1979-01-24
EP0000381B1 true EP0000381B1 (de) 1980-08-06

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EP78100323A Expired EP0000381B1 (de) 1977-07-15 1978-07-07 Verfahren zur Herstellung von seitenständige Hydroxylgruppen aufweisenden Isocyanat-Polyadditionsprodukten und die nach diesem Verfahren erhaltenen Produkte.

Country Status (6)

Country Link
US (1) US4192937A (enrdf_load_stackoverflow)
EP (1) EP0000381B1 (enrdf_load_stackoverflow)
JP (1) JPS5420098A (enrdf_load_stackoverflow)
DE (2) DE2732131A1 (enrdf_load_stackoverflow)
ES (1) ES471750A1 (enrdf_load_stackoverflow)
IT (1) IT1105095B (enrdf_load_stackoverflow)

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ES471750A1 (es) 1979-02-01
DE2732131A1 (de) 1979-01-25
JPS6131728B2 (enrdf_load_stackoverflow) 1986-07-22
EP0000381A1 (de) 1979-01-24
IT1105095B (it) 1985-10-28
DE2860113D1 (en) 1980-11-27
JPS5420098A (en) 1979-02-15
US4192937A (en) 1980-03-11
IT7850255A0 (it) 1978-07-12

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