EP2900714A1 - Systèmes durcissant à l'humidité à base de carbodiimides et d'anhydrides - Google Patents

Systèmes durcissant à l'humidité à base de carbodiimides et d'anhydrides

Info

Publication number
EP2900714A1
EP2900714A1 EP13760031.8A EP13760031A EP2900714A1 EP 2900714 A1 EP2900714 A1 EP 2900714A1 EP 13760031 A EP13760031 A EP 13760031A EP 2900714 A1 EP2900714 A1 EP 2900714A1
Authority
EP
European Patent Office
Prior art keywords
groups
carbodiimide
compound
composition
composition according
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Withdrawn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
EP13760031.8A
Other languages
German (de)
English (en)
Inventor
Emmanouil Spyrou
Friedrich Georg Schmidt
Marion EWALD
Susanne Kreischer
Andrea Henschke
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa 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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP2900714A1 publication Critical patent/EP2900714A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • 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
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • C08G18/025—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing carbodiimide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C267/00—Carbodiimides
    • 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

Definitions

  • Moisture-curing polyurethane systems based on isocyanates are known (for example in US7317051, WO2001070839, US5369208 or DE4236562). They are z. B. used as paint, adhesive or sealants and apply in the application as user-friendly, since no mixing or stirring operations are necessary here. The curing is done by the
  • an approximately equimolar ratio of the carbodiimide group to the released carboxylic acid group, i. of about 1: 1 is particularly preferred.
  • methyldiphenyl diisocyanate such as diphenylmethane-2,2'-diisocyanate, diphenylmethane-2,4-diisocyanate, diphenylmethane-4,4'-diisocyanate or mixtures comprising the abovementioned MDIs, 2,4- and / or 2, 6-tolylene diisocyanate (TDI), 4-methylcyclohexane-1,3-diisocyanate, 2-butyl-2-ethylpentamethylene diisocyanate, 3 (4) -isocyanatomethyl-1-methylcyclohexyl isocyanate, 2-isocyanatopropylcyclohexyl isocyanate, 2, 4'-methylene-bis (cyclohexyl) diisocyanate, 1, 4-diisocyanato-4-methyl-pentane.
  • MDI methyldiphenyl diisocyanate
  • TDI 6-tolylene diis
  • composition comprising carbodiimide-containing compounds which have been prepared by reacting a
  • trimethylolpropane trimethylolpropane
  • compound B is preferably selected from the following compounds without limiting the compounds to those mentioned:
  • alkyl-substituted derivatives of the compound having at least one carboxylic anhydride group preferably having 1 to 20 carbon atoms, or other carboxy-containing compounds having at least one carboxylic acid anhydride group can be used, preferably dodecenylsuccinic anhydride,
  • component B all compounds can be used which have at least one carboxylic acid anhydride group. In simple cases simple intramolecular
  • Carboxylic anhydrides with 2 to 8 carbon atoms Preferred compounds have a intramolecularly formed carboxylic acid anhydride group. These are in particular succinic anhydride, malonic anhydride, maleic anhydride, 1, 2-cyclohexanedioic anhydride, phthalic anhydride, pyrromellitic anhydride and
  • Trimellitic Also possible are intermolecular carboxylic anhydrides.
  • the solvents optionally present in the composition are preferably anhydrous and are in particular inert to the carbodiimide, anhydride and / or NCO groups.
  • Preferred solvents C) are inert solvents in the presence of compounds A) and B); in particular, the solvents are also inert under the reaction conditions, as in the later polymerization or polyaddition. Preference is given to using an organic or inorganic inert liquid or mixture containing at least two inert liquids as the solvent C).
  • the solvent is anhydrous, i. the solvent contains less than or equal to 10 ppm by weight, in particular less than or equal to 5 ppm by weight, preferably less than or equal to 1 ppm by weight of water.
  • the water content can be determined by methods known to the person skilled in the art, for example by the Karl Fischer method.
  • solvent C) is selected from aromatic or aprotic solvents, preferably acetone, ethyl acetate, butyl acetate, xylene, aromatic solvents with boiling points above xylenes, in particular aromatic solvents with boiling points of 145 to 250 ° C.,
  • Solvesso 100 95-100% aromatic low boilers, aromatic solvents naphtha ( * 64742-95-6), 0 - 5% mixed xylenes (1330-20-7) [215-535-7], 35 - 45% 1 , 2,4-trimethylbenzene (95-63-6, 0-5% cumene (98-82-8), which is an aromatic solvent Solvesso 100 has an aromatics content of 99% by weight (boiling point 164-180 ° C);
  • Solvesso 150 aromatic solvent, content of aromatics 99 wt .-% boiling point 181 - 207 ° C.
  • the composition may also contain auxiliaries and additives D).
  • auxiliaries and additives can be selected from:
  • leveling agent and / or light stabilizer for example polysilicone or acrylate being used as leveling agent and / or sterically hindered amines and / or customary auxiliaries being used as light stabilizer, for example
  • catalyst in particular dibutyltin dilaurate, or tertiary amines, such as. B. 1, 4-diazabicyclo [2,2,2,] octane, as well as
  • composition may comprise:
  • Leveling agents polysilicone or acrylates are used and / or, for example, as light stabilizers sterically hindered amines and / or as auxiliaries mentioned in EP 669 353,
  • catalyst 0.01 to 0.5 wt .-% catalyst, in particular organometallic compounds, dibutyltin dilaurate, or tertiary amines, such as. B. 1, 4-diazabicyclo [2.2.2,] octane, and ad. 100 wt .-% of the total composition, the component A) at least one compound containing at least one carbodiimide group and the component B) at least one compound containing at least one anhydride group and optionally C) solvent.
  • organometallic compounds such as. B. 1, 4-diazabicyclo [2.2.2,] octane
  • Solvent mixture C) and optionally in the presence of auxiliaries and additives D) are used in formulations of the composition in the molar ratio of the reactive groups
  • the carbodiimide group and the carboxylic acid anhydride group do not react with each other.
  • the carboxylic acid anhydride group is hydrolyzed to two carboxylic acid groups. Humidity may be sufficient for hydrolysis. Then the carboxylic acids react within a short time with the carbodiimide group with crosslinking.
  • the invention likewise relates to a process for the preparation of a composition, in particular a moisture-activatable or in the presence of moisture-reactive composition, and a composition obtainable by this process, wherein the following components
  • the composition is prepared essentially anhydrous and, in particular with the exclusion of moisture, filled into a hermetically sealable container, and preferably the container is substantially closed in such a way that the composition does not come in contact with moisture.
  • component A) is preferably selected from carbodiimide groups and NCO-containing compounds and / or prepolymers containing carbodiimide groups, the prepolymers being prepared by compounds containing carbodiimide and isocyanate groups with monomeric, oligomeric or polymer polyols and / or polyamines are reacted, optionally to a
  • polyols are the abovementioned polyvalent monomeric or oligomeric alcohols and also polymeric polyols.
  • polyols or polyamines for example, polyesters, polycaprolactones, polyethers, polycarbonates, polyamides, polyurethanes, polyureas or poly (meth) acrylates having terminal OH and / or amine groups can be used.
  • polymeric amines there may be exemplified the following, such as polyetheramines, polyether glycolamine or polypropylene glycolamine.
  • the invention likewise relates to a process for preparing the composition in which the prepolymers, in particular the prepolymers containing carbodiimide groups, are prepared by a molar ratio of the NCO groups of the isocyanates and NCO-reactive groups, such as hydroxyl groups or NH groups.
  • Groups of polyols or polyamines from 5: 1 to 1: 5 is set, preferably, a ratio of 1: 1 is set, and optionally reacted at a temperature of 10 to 200 ° C. Preferably, it is reacted at 40 to 120 ° C.
  • An additional object of the invention is the use of a composition in which the composition is admixed with a defined amount of moisture, water or water-containing solvents, in particular for activation of the composition or for reaction, preferably for crosslinking of an activated composition.
  • the activation of the composition is carried out by the reaction of H 2 0 with a
  • Carboxylic anhydride to form two carboxylic acid groups, which then react with one or two carbodiimide groups.
  • the subject of the invention is a by
  • Moisture activatable composition comprising compounds containing carbodiimide group groups and compounds containing carboxylic anhydride groups, optionally containing solvents, and optionally auxiliaries and additives.

Landscapes

  • 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)
  • Sealing Material Composition (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition comprenant des composants qui sont choisis parmi A) au moins un composé contenant au moins un groupe carbodiimide, B) au moins un composé contenant au moins un groupe anhydride carboxylique, C) facultativement un solvant, et D) des adjuvants et additifs. L'invention concerne en outre un procédé pour la produire ainsi que son utilisation.
EP13760031.8A 2012-09-27 2013-09-09 Systèmes durcissant à l'humidité à base de carbodiimides et d'anhydrides Withdrawn EP2900714A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012217552.0A DE102012217552A1 (de) 2012-09-27 2012-09-27 Feuchtigkeitshärtende Systeme auf Basis von Carbodiimiden und Anhydriden
PCT/EP2013/068535 WO2014048700A1 (fr) 2012-09-27 2013-09-09 Systèmes durcissant à l'humidité à base de carbodiimides et d'anhydrides

Publications (1)

Publication Number Publication Date
EP2900714A1 true EP2900714A1 (fr) 2015-08-05

Family

ID=49162136

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13760031.8A Withdrawn EP2900714A1 (fr) 2012-09-27 2013-09-09 Systèmes durcissant à l'humidité à base de carbodiimides et d'anhydrides

Country Status (6)

Country Link
US (1) US20150197674A1 (fr)
EP (1) EP2900714A1 (fr)
JP (1) JP2016500711A (fr)
CN (1) CN104781296A (fr)
DE (1) DE102012217552A1 (fr)
WO (1) WO2014048700A1 (fr)

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2853518A (en) 1956-07-30 1958-09-23 Du Pont Chemical process
US2853473A (en) 1956-08-27 1958-09-23 Du Pont Production of carbodiimides
US2941966A (en) 1956-08-27 1960-06-21 Du Pont Carbodiimide polymers
US4332925A (en) * 1981-03-30 1982-06-01 General Electric Company Modified polyamideimide resins
DE3512918A1 (de) 1985-04-11 1986-10-16 Bayer Ag, 5090 Leverkusen Carbodiimidgruppen enthaltende isocyanat-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als zusatzmittel fuer waessrige loesungen oder dispersionen von kunststoffen
DE4019026A1 (de) * 1990-06-14 1991-12-19 Bayer Ag Beschichtungsmittel und seine verwendung zur beschichtung hitzeresistenter substrate
DE4236562A1 (de) 1992-10-29 1994-05-05 Elastogran Gmbh Feuchtigkeitshärtende Polyurethan-Einkomponenten-Bindemittel
US5369208A (en) 1993-05-24 1994-11-29 Olin Corporation Low VOC, fast drying, moisture curable, one-component isocyanate-based coating compositions
US5578675A (en) * 1993-07-21 1996-11-26 Basf Corporation Non-isocyanate basecoat/clearcoat coating compositions which may be ambient cured
DE4406444A1 (de) 1994-02-28 1995-08-31 Huels Chemische Werke Ag Hydroxyl- und uretdiongruppenhaltige Polyadditionsprodukte und Verfahren zu ihrer Herstellung sowie deren Verwendung zur Herstellung abspaltfreier Polyurethan-Pulverlacke hoher Reaktivität und die danach hergestellten Polyurethan-Pulverlacke
DE19804911A1 (de) * 1998-02-07 1999-08-12 Basf Ag Verfahren zur Herstellung von Fluorchlorkohlenwasserstoff-freien weichelastischen, halbharten oder harten Polyurethanformkörpern mit einem zelligen Kern und einer verdichteten Randzone
TW574242B (en) 2000-03-23 2004-02-01 Huntsman Int Llc Low temperature cure diphenylmethane diisocyanate (MDI) prepolymers and reaction system and method for preparing the same
US7317051B2 (en) 2003-11-14 2008-01-08 Chem Link Moisture curable sealer and adhesive composition
DE102009027246A1 (de) * 2009-06-26 2010-12-30 Evonik Degussa Gmbh Katalysatorarme Carbodiimidgruppen und/oder Uretonimingruppen aufweisende Isocyanatmischungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2014048700A1 *

Also Published As

Publication number Publication date
WO2014048700A1 (fr) 2014-04-03
CN104781296A (zh) 2015-07-15
DE102012217552A1 (de) 2014-03-27
US20150197674A1 (en) 2015-07-16
JP2016500711A (ja) 2016-01-14

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