EP1817385A1 - Polyols stables a l'hydrolyse, hydrophobes et exempts de solvants - Google Patents

Polyols stables a l'hydrolyse, hydrophobes et exempts de solvants

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Publication number
EP1817385A1
EP1817385A1 EP05802667A EP05802667A EP1817385A1 EP 1817385 A1 EP1817385 A1 EP 1817385A1 EP 05802667 A EP05802667 A EP 05802667A EP 05802667 A EP05802667 A EP 05802667A EP 1817385 A1 EP1817385 A1 EP 1817385A1
Authority
EP
European Patent Office
Prior art keywords
polyols
weight
molecular weight
ester group
groups
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Withdrawn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
EP05802667A
Other languages
German (de)
English (en)
Inventor
Meike Niesten
Gerhard Ruttmann
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.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
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 Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of EP1817385A1 publication Critical patent/EP1817385A1/fr
Withdrawn legal-status Critical Current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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
    • 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
    • C08G18/58—Epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes

Definitions

  • the invention relates to novel hydrophobic, hydrolysis-stable polyols, a process for their preparation and based thereon solvent-free binder mixtures, which in particular for the corrosion protection of metallic substrates and for coating mineral (alkaline) substrates z. B. are suitable for floor coatings.
  • Solvent-free two-component coating systems (2K systems) of the prior art are essentially divided into epoxy resin (2K-EP) systems and polyurethane (2K-PUR) systems.
  • Coatings based on 2-component EP systems combine good mechanical strength with high resistance to solvents and chemicals. In addition, they are characterized by a very good substrate adhesion.
  • a significant disadvantage over the polyurethane systems is their poor elasticity, especially at low temperatures. This brittleness leads to a poor crack bridging through the coating, so that an attack on the substrate can take place here.
  • An additional disadvantage is the very low resistance to organic acids. This is particularly problematic for applications in the food sector, since there are often released organic acids as waste products.
  • a balanced combination of hardness and elasticity is the outstanding feature of 2K-PUR coatings and the biggest advantage over 2K-EP coatings.
  • organic acid resistance of 2K PUR coatings is significantly better than 2K EP coatings.
  • polyether polyols Due to their relatively high tendency to absorb water, however, polyether polyols can also be used to a limited extent only as a binder component for this field of application.
  • the correspondingly large amount of absorbed water can lead to the reaction with NCO groups, in which CO 2 is split off. This leads due to blistering in Lackf ⁇ lm to inhomogeneities and turbidity.
  • 2-component PUR coatings based on polyacrylate polyols are characterized by good resistance to saponification, but their relatively high viscosity level is disadvantageous. Therefore, either solvents or reactive diluents such as polyether polyols or polyfunctional alcohols are always added to adjust the viscosity. As is the case with the exclusive use of polyether polyols as crosslinkers, the water absorption behavior generally increases as a result.
  • oligomeric bisphenol A resins which are obtained by reacting bisphenol A with epichlorohydrin, sufficiently, for example, from Kittel,, Textbook of coatings and coatings, S. Hirzel Verlag, Stuttgart, Leipzig, Second Edition 1998, Part 2 , Page 267 - 320 known.
  • Such resins are typically used in combination with amines in 2K epoxy systems.
  • WO8304414 describes, for example, polyol resins which are obtained from aliphatic diepoxides, aromatic diepoxides and compounds which contain at least 2 aromatic hydroxyl groups. These resins can be cured with polyisocyanates in room temperature Coating systems are used. However, due to the high viscosities of the OH-functional resins described therein, they can only be used in solvent-based coating systems.
  • solvent-free diols are known, which are obtained by ring opening of epoxides with amines. Such diols can be cured in principle with polyisocyanates, wherein the presence of amine groups interferes. Since, especially when aromatic polyisocyanates are used, the NCO / NH reaction is extremely fast, such systems cure too quickly, so that manual processing in thick-film applications into homogeneous, bubble-free layers is hardly possible.
  • the object of the present invention was therefore to provide a hydrophobic, low-viscosity polyol component which can be further processed manually to give solvent-free binder mixtures and which does not have the abovementioned disadvantages of the lack of resistance of the coatings based thereon.
  • the invention relates to a method for producing an ester-free hydrophobic polyol having an OH number of 100 to 500 mg KOH / g, an average OH functionality of 1.8 to 4.5, a viscosity at 23 0 C from 1 000 to 50 000 mPa.s and a water absorption after 21 days at 23 0 C and a humidity of 97% less than 5 wt .-%, in which
  • R and R 'independently of one another are hydrogen or an organic radical having 1 to 6 C atoms A2) 0 to 40 wt .-% of one or more aliphatic diglycidyl ethers having a number average molecular weight of 200 to 700 g / mol corresponding to the general formula (II)
  • X is a divalent aliphatic hydrocarbon radical
  • R is a monovalent optionally oxygen-containing alkyl, aryl or aralkyl radical
  • R "' is a C 8 -C 20 -alkyl radical
  • an object of the present invention is the polyols prepared by the process essential to the invention.
  • the components Al) to A3) are particularly preferably used in amounts of from 20 to 40% by weight of Al), from 5 to 35% by weight of A2) and from 20 to 55% by weight of A3).
  • the molar ratio of Epoxidgrappen from Al) to OH groups from A2) and A3) 1: 0.8 to 1: 1.7.
  • component Al for example, bisphenol A, bisphenol F, trimethylcyclohexyl-bisphenol can be used. Preference is given to using bisphenol A in Al).
  • component A2 for example 1,2-Ethandioldiglycidy ether, 1,3-Propandioldiglyci- dylether, 1,2-Propandioldiglycidy ether, 1,4 Butandioldiglycidylether, 1,6-Hexandioldiglycidyl- ether, Neopentylglykoldiglycidylether, Cyclohexandimethanoldiglycidylether, Glycerindiglycidyl- ether, Polypropylenglykoldiglycidylether or mixtures thereof are used.
  • the latter are commercially available, for example, under the names Polypox R3, Polypox Rl 8 or Polypox Rl 4 from UPPC Baltringen, Germany.
  • component A3) for example, 2-ethylhexyl glycidyl ether, dodecyl glycidyl ether, Tetradecylglycidylether, Hexadecylglycidylether, Octadecylglycidylether, monoepoxides of ⁇ -olefins having 8 to 20 carbon atoms, tert-Butylphenylglycidylether, Kresylglycidylether, 2-methyl phenylglycidylether, 4-tert Butylphenylglycidylether, 4-Methoxyphenylglycidylether, 3-pentadecadienylphenylglycidylether or mixtures thereof.
  • mixtures of dodecylglycidyl ether and tetradecylglycidyl ether are preferably used.
  • the preparation of the polyols of the invention is typically carried out by mixing the components Al) to A3) with each other in any order and simultaneous or subsequent forming heating the mixture at 50 to 200 0 C, preferably 100 to 180 ° C.
  • the reaction can be carried out catalyst-free or using a catalyst. If a catalyst is used, these may be the compounds and catalyst systems known per se to the person skilled in the art, for example alkali metal hydroxides, tertiary amines, quaternary ammonium salts, quaternary phosphonium salts, trialkylphosphines or triarylphosphines.
  • the reaction is typically carried out until a complete reaction of the epoxy groups (determined according to DIN 16945, wherein the content is based on a molar mass of 42 g / mol) can be detected.
  • the thus obtainable polyols preferably have a viscosity at 23 0 C 1000-50000 mPa.s.
  • the polyols thus obtainable preferably have a number average molecular weight of 500 to 2500 g / mol.
  • the polyols thus obtainable preferably have OH functionalities of 1.8 to 4.5 and OH numbers of 100 to 500 mg KOH / g.
  • esterfteien polyols are characterized by a particularly high hydrophobicity. They are therefore particularly suitable for the production of 2-component polyurethane coating systems (2-K PUR systems) for thick-film applications, for example in the construction sector.
  • the water uptake of the polyols obtainable according to the invention after 21 days at 23 0 C storage and a humidity of 97% below 3 wt .-%.
  • a sample is stored open at 23 ° C. and 97% relative humidity for 21 days and the weight increase is subsequently determined.
  • organic polyisocyanates having an average NCO functionality of at least 2 and a molecular weight of at least 140 g / mol are typically used.
  • unmodified organic polyisocyanates of the molecular weight range 140 to 300 g / mol
  • lacquer polyisocyanates having a molecular weight in the range from 300 to 1000 g / mol
  • urethane-containing NCO prepolymers of more than 1000 g / Mol lying molecular weight or mixtures of (i) to (iii).
  • polyisocyanates of group (i) are 1,4-dinocyanatobutane, 1,6-diisocyanatohexane (HDI), 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- and 2,4,4- Trimethyl-l, 6-diisocyanatohexane, 1-isocyanato-3, 3,5-trimethyl-S-isocyanatomethylcyclohexane (IPDI), 1-isocyanato-1-methyl-4- (3) - isocyanatomethylcyclohexane, bis ( 4-isocyanatocyclohexyl) methane, 1, 10-diisocyanatodecane, 1,12-diisocyanato-dodecane, cyclohexane-1,3- and 1,4-diisocyanate, xylylene diisocyanate isomers, triisocyanatononane (TIN), 2,4-diisocyana
  • Polyisocyanates of group (ii) are the conventional lacquer polyisocyanates.
  • lacquer polyisocyanates is understood as meaning compounds or mixtures of compounds which are obtained by per se known oligomerization reaction of simple diisocyanates of the type mentioned under (i) by way of example. Suitable oligomerization reactions are e.g. carbodiimidization, dimerization, trimerization, biuretization, urea formation, urethanization, allophanatization and / or cyclization to form oxadiazine structures. Often, during the "oligomerization", several of the reactions mentioned proceed simultaneously or in succession.
  • the "paint polyisocyanates” (ii) are preferably biuret polyisocyanates, isocyanurate group-containing polyisocyanates, isocyanurate- and uretdione-group-containing polyisocyanate mixtures, urethane and / or allophanate group-containing polyisocyanates or isocyanurate and allophanate group-containing polyisocyanate mixtures based on simple diisocyanates.
  • Polyisocyanates of group (iii) are the per se known isocyanate group-containing prepolymers based on simple diisocyanates of the type exemplified above and / or based on lacquer polyisocyanates (ii) on the one hand and organic polyhydroxy compounds of a molecular weight above 300 g / mol on the other hand.
  • the urethane group-containing lacquer polyisocyanates of group (ii) are derivatives of low molecular weight polyols in the molecular weight range 62 to 300 g / mol
  • suitable polyols are, for example, ethylene glycol, propylene glycol, trimethylolpropane, glycerol or mixtures of these alcohols are used to prepare the NCO -Prepolymeren of group (iii) Polyhydroxylver- compounds of over 300 g / mol, preferably over 500 g / mol, more preferably a lying between 500 and 8000 g / mol molecular weight.
  • Such polyhydroxyl compounds are, in particular, those which have 2 to 6, preferably 2 to 3, hydroxyl groups per molecule and are selected from the group consisting of ether, ester, thioether, carbonate and polyacrylate polyols and mixtures of such polyols .
  • the stated higher molecular weight polyols can also be used in mixtures with the mentioned low molecular weight polyols, so that directly mixtures of low molecular weight urethane groups having Lackpolyiso- cyanaten (ii) and higher molecular weight NCO prepolymers (iii) result.
  • diisocyanates (i) of the type exemplified above or lacquer polyisocynatates of the type exemplified under (ii) with the higher molecular weight hydroxyl compounds or mixtures thereof with low molecular weight polyhydroxy compounds are exemplified mentioned type while maintaining an NCO / OH equivalent ratio of 1.1: 1 to 40: 1, preferably 2: 1 to 25: 1 reacted with urethane formation.
  • an excess of distillable starting diisocyanate it may be removed by distillation following the reaction so that monomer-free NCO prepolymers, i. Mixtures of starting diisocyanates (i) and true NCO prepolymers (iii).
  • 2,2'-, 2,4'-, 4,4'-, diisocyanatodiphenylmethane or technical polyisocyanate mixtures of the diphenylmethane series or polyisocyanates of the above-defined group ii) are preferably used in b).
  • the amounts of components a), b) and optionally further constituents are chosen such that an NCO: OH equivalent ratio of 0.5: 1 to 2.0: 1, preferably 0.8 : 1 to 1.5: 1, results.
  • the compounds known per se in polyurethane chemistry can be used to accelerate the NCO / OH reaction (cf "Kunststoff Handbuch 7, Polyurethanes” Carl-Hanser-Verlag, Kunststoff-Vienna, 1984, pp. 97-98).
  • tertiary amines such as triethylamine, pyridine, methylpyridine, benzyldimethylamine, N, N-endoethylenepiperazine, N-methylpiperidine, pentamethyldiethylenetriamine, N 5 N-dimethylaminocyclohexane, N, N'-dimethylpiperazine or metal salts such as iron (IH) chloride, zinc chloride, zinc 2-ethylcaproate, tin (IT) octoate, tin (H) -ethylcaproate, tin (II) palmitate, dibutyltin (TV) dilaurate and molybdenum glycolate or any mixtures of such catalysts. It is preferable to use tin compounds as compounds of component C).
  • auxiliaries or additives in the 2-K PUR systems z.
  • surfactants internal release agents, fillers, dyes, pigments, flame retardants, hydrolysis
  • the components a) and b) are mixed with one another such that an NCO: OH equivalent ratio of 0.5: 1 to 2.0: 1, preferably 0.8: 1 to 1 , 5: 1 results.
  • the auxiliaries and additives mentioned and also catalysts can be admixed.
  • the application of the 2-component PU systems according to the invention can be carried out by methods customary per se in the art, such as brushing, knife coating, spraying, dipping.
  • Preferred layer thicknesses are from 0.5 to 10 mm, preferably from 0.7 to 6 mm, whereby the production of thinner or thicker layers is not excluded.
  • the 2-component PU systems are preferably used for the production of coatings for the protection of metallic substrates against mechanical damage and corrosion and for the protection of mineral substrates, such as concrete, against environmental influences and mechanical damage.
  • the dynamic viscosities were determined according to DIN 53019 at 23 0 C with a rotational viscometer (Viscotester 550, Thermo Haakke GmbH, D-76227 Düsseldorf, Germany) at a shear rate of 40 s -1.
  • the Shore D hardness was determined according to DIN 53505.
  • the water uptake was determined by the weight gain of a sample after 21 days open storage at 23 0 C and 97% humidity.
  • the water absorption is defined according to the following formula:
  • the polyol would have an OH number of 185 mg KOH / g, a content of epoxy groups of 6.0 wt .-%, a viscosity at 23 0 C of 4370 mPa.s and a water absorption of 2.6 wt .-%.
  • the polyol had an OH number of 170 mg KOH / g, a content and epoxy groups of 39 wt .-%, a viscosity at 23 ° C of 11 800 mPa.s, and a water absorption of 1.1 wt .-%.
  • Desmophen ® 1150 commercial product of Bayer MaterialScience, Leverkusen, Germany. With an OH number of 155 mg KOH / g and a viscosity of 3500 mPa.s and a water absorption of 1.2 wt.%.
  • Desmophen ® VPLS 2328 commercial product of Bayer MaterialScience AG, Leverkusen, Germany, solvent-free polyester having an OH number of 257 mg KOH / g and a viscosity at 23 ° C of 800 mPa.s and a water absorption of 6.2 wt.% ,
  • the polyol has at room temperature (23 0 C) has a viscosity> 200 000 mPa.s and is therefore not manually processable.
  • the polyol component with the polyisocyanate component in an NCO / OH ratio of 1: 1 (amounts according to Table 1) mixed and poured onto a plastic substrate in a layer thickness of 3 to 5 mm.
  • the subsequent curing was carried out by 7 days storage of the plates at room temperature.
  • composition (parts by weight) 1 2 3
  • the Lissemittle clar polyols according to the invention are characterized by a good hydrolytic stability. After storage of the cured samples in NaOH and sulfuric acid no significant loss of hardness was observed when using the essential polyols. Furthermore, they have a very low water absorption of ⁇ 5 wt.%. Comparative polyol 5 shows that when an aromatic diglycidyl ether is used instead of an aliphatic diglycidyl ether, the polyols are no longer solvent-free processable due to the sharply increasing viscosity.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

Nouveaux polyols hydrophobes et stables à l'hydrolyse, procédé de production desdits polyols et mélanges liants exempts de solvants à base de ces polyols, qui sont appropriés en particulier pour la protection contre la corrosion de substrats métalliques, ainsi que pour couvrir des fonds minéraux (alcalins), par exemple pour couvrir des sols.
EP05802667A 2004-11-23 2005-11-10 Polyols stables a l'hydrolyse, hydrophobes et exempts de solvants Withdrawn EP1817385A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004056398A DE102004056398A1 (de) 2004-11-23 2004-11-23 Hydrolysestabile, hydrophobe, lösemittelfreie Polyole
PCT/EP2005/012013 WO2006056320A1 (fr) 2004-11-23 2005-11-10 Polyols stables a l'hydrolyse, hydrophobes et exempts de solvants

Publications (1)

Publication Number Publication Date
EP1817385A1 true EP1817385A1 (fr) 2007-08-15

Family

ID=35500583

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05802667A Withdrawn EP1817385A1 (fr) 2004-11-23 2005-11-10 Polyols stables a l'hydrolyse, hydrophobes et exempts de solvants

Country Status (4)

Country Link
US (1) US20060111545A1 (fr)
EP (1) EP1817385A1 (fr)
DE (1) DE102004056398A1 (fr)
WO (1) WO2006056320A1 (fr)

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US4284574A (en) * 1979-06-15 1981-08-18 Ciba-Geigy Corporation Diglycidyl ethers of di-secondary alcohols, their preparation, and curable compositions containing them
US4758638A (en) * 1982-06-10 1988-07-19 The Dow Chemical Company Advanced epoxy resins
GB2129808B (en) * 1982-06-10 1986-07-09 Dow Chemical Co Advanced epoxy resins and coating compositions containing the advanced epoxy resins
US4608313A (en) * 1982-06-10 1986-08-26 The Dow Chemical Company Advanced epoxy resins crosslinked with polyisocyanates
US4783509A (en) * 1985-03-25 1988-11-08 The Dow Chemical Company Non-thermoset thermally stable capped epoxy resin compositions
EP0223403B1 (fr) * 1985-10-25 1993-08-04 Beecham Group Plc Dérivé de pipéridine, sa préparation et son utilisation comme médicament
US4868230A (en) * 1987-07-02 1989-09-19 The Dow Chemical Company Cationic, advanced epoxy resins from (1) diglycidyl ethers of phenols (2) diglycidyl ethers of alkane diols and (3) a dihydric phenol
US4698141A (en) * 1986-07-18 1987-10-06 The Dow Chemical Company Cationic, advanced epoxy resin compositions
US4977202A (en) * 1987-07-02 1990-12-11 The Dow Chemical Company Cationic, advanced epoxy resin compositions from (1) diglycidyl ethers of phenols (2) diglycidyl ethers of alkane diols and (3) dihydric phenols
US4980397A (en) * 1987-07-02 1990-12-25 The Dow Chemical Company Cationic, advanced epoxy resin compositions based on aliphatic diols, dihydric phenols and diglycidyl ethers of dihydric phinols
US4863575A (en) * 1987-07-16 1989-09-05 The Dow Chemical Company Cationic, advanced epoxy resin compositions incorporating glycidyl ethers of oxyalkylated aromatic or cycloalkphatic diols
US5591788A (en) * 1987-07-16 1997-01-07 The Dow Chemical Company Cationic, advanced epoxy resin compositions incorporating glycidyl ethers of oxyalkylated aromatic or cycloaliphatic diols
US5248741A (en) * 1987-07-16 1993-09-28 The Dow Chemical Company Cationic, advanced epoxy resin compositions incorporating glycidyl ethers of oxyalkylated aromatic or cycloaliphatic diols
CA1336029C (fr) * 1987-11-06 1995-06-20 Michiharu Kitabatake Composition de resine de revetement contenant une resine epoxy-polyamine
US5360838A (en) * 1987-12-03 1994-11-01 The Dow Chemical Company Cationic, capped advanced epoxy resin compositions from glycidyl ethers of oxyalkylated aromatic or cycloaliphatic diols
US5212262A (en) * 1987-12-03 1993-05-18 The Dow Chemical Company Epoxy resin advanced with diphenol/diglycidyl ether adducts
TW311923B (fr) * 1992-01-27 1997-08-01 Ciba Sc Holding Ag
WO2000071337A1 (fr) * 1999-05-26 2000-11-30 Henkel Corporation Revetements appliques par depot sans courant
US6565772B2 (en) * 2001-09-25 2003-05-20 Midwest Thermal Spray Conductive resin composition
US7615604B2 (en) * 2003-01-17 2009-11-10 The United States Of America As Represented By The Secretary Of The Navy Diols formed by ring-opening of epoxies

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Also Published As

Publication number Publication date
DE102004056398A1 (de) 2006-05-24
WO2006056320A1 (fr) 2006-06-01
US20060111545A1 (en) 2006-05-25

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