EP0998507A1 - Systemes oligomeres epoxyde/isocyanate - Google Patents

Systemes oligomeres epoxyde/isocyanate

Info

Publication number
EP0998507A1
EP0998507A1 EP98935946A EP98935946A EP0998507A1 EP 0998507 A1 EP0998507 A1 EP 0998507A1 EP 98935946 A EP98935946 A EP 98935946A EP 98935946 A EP98935946 A EP 98935946A EP 0998507 A1 EP0998507 A1 EP 0998507A1
Authority
EP
European Patent Office
Prior art keywords
hydroxyl
composition
component
epoxy
isocyanate
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Withdrawn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
EP98935946A
Other languages
German (de)
English (en)
Inventor
Robert John Barsotti
Lee R. Harper
John David Nordstrom
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0998507A1 publication Critical patent/EP0998507A1/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Withdrawn legal-status Critical Current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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
    • 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4045—Mixtures of compounds of group C08G18/58 with other macromolecular compounds
    • 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
    • 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
    • C09D175/08—Polyurethanes from polyethers

Definitions

  • This invention concerns coating systems comprising non-isocyanate and isocyanate components in organic solvents.
  • the non-isocyanate components being an oligomer or blend of oligomers containing at least two functional groups, at least one being epoxy; optionally present is a polyester or oligo-ester or acrylic polymer having at least two hydroxyl groups.
  • U.S. 5,215,783 discloses a process for coating a substrate with a waterborne basecoat and a clearcoat containing a polymeric epoxy group.
  • the invention specifically concerns a curable coating composition of a binder in organic solvent comprising A) a non-isocyanate component wherein: i) 5-100% of the non-isocyanate component is an oligomer or blend of oligomers with a weight average molecular weight not exceeding about 3,000, a polydispersity not exceeding 1.7, containing at least two functional groups with at least one being an epoxy group, the remaining being epoxy or hydroxyl; ii) 0-95% by weight of the non-isocyanate component of a polyester, oligo-ester or acrylic polymer each having at least two hydroxyl groups; and
  • Contemplated embodiments of the invention are those wherein component (ii) is absent and cure is accelerated by ambient moisture, and where component (ii) contains at least one hydroxyl group derived from acrylates and/or methacrylates, and at least one epoxy group derived from glycidyl methacrylate and/or glycidyl acrylate.
  • compositions cured at ambient conditions or baked at elevated temperatures.
  • Such composition can include hydroxyl and/or epoxy-functional nonaqueous dispersions, and these optional crosslinkers: aldimines, ketimines, and polyaspartic esters.
  • Catalysts such as tin and tertiary amines (alone or in combination with acetic acid) can be employed.
  • the disclosed composition is useful in clearcoats and pigmented compositions to coat substrates, preferably vehicle bodies and vehicle body parts.
  • compositions of this invention show a remarkable combination of wet-properties and film-properties.
  • the combination of oligomeric epoxies crosslinked by oligomeric isocyanates have shown
  • VOC volatile organic content
  • binder components of these systems include epoxy- functional oligomers, epoxy/hydroxyl-functional oligomers and isocyanate- fiinctional oligomers.
  • Other functional oligomers and polymers can also be included in the formulations of this invention.
  • the oligomeric component contains at least two functional groups and should have a molecular weight of less than about 3000.
  • Typical epoxy components containing a hydroxy functionality or (OH) group include, among others, sorbitol polyglycidyl ether, mannitol polyglycidyl ether, pentaerythritol polyglycidyl ether, glycerol polyglycidyl ether, low molecular weight epoxy resins such as epoxy resins of epichlorohydrin and bisphenol- A, and polyglycidyl ethers of isocyanurates, for example, "Denecol" EX301 from Nagase and DCE-358® sorbitol polyglycidyl ether from Dixie Chemical. These types of oligomers are preferred for ambient cure, but are also useful for baked systems.
  • Epoxy components which typically do not contain significant hydroxy functionality include, among others, di- and polyglycidyl esters of polycarboxylic acids, and di- and polyglycidyl esters of acids, such as Araldite CY-184® from Ciba-Geigy, or XU-71950 from Dow Chemical are preferred since they form high quality finishes. Cycloaliphatic epoxies can also be used, such as ERL-4221 from Union Carbide. These oligomers are primarily used in baked systems, but can be used at low levels in ambient cured systems. Component B
  • the composition also contains an organic isocyanate crosslinking agent in the amount of 0.5 to 3.0 equivalents of isocyanate per equivalent of epoxy or epoxy/hydroxyl.
  • an organic isocyanate crosslinking agent in the amount of 0.5 to 3.0 equivalents of isocyanate per equivalent of epoxy or epoxy/hydroxyl.
  • Optimum film properties are achieved when one epoxy group reacts with two isocyanate groups. However, it was determined that a broad latitude in stoichiometry of isocyanate to epoxy can sometimes be useful depending on final wet- and dry-coating properties desired.
  • Any of the conventional aromatic, aliphatic, or cycloaliphatic isocyanates; trifunctional isocyanates and isocyanate functional adducts of a polyol and a diisocyanate can be used.
  • diisocyanates are 1,6-hexamethylene diisocyanate, isophorone diisocyanate, 4,4'-biphenylene diisocyanate, toluene diisocyanate, bis-cyclohexyl diisocyanate, tetramethylene xylene diisocyanate, ethyl ethylene diisocyanate, 2, 3 -dimethyl ethylene diisocyanate, 1-methyltrimethylene diisocyanate, 1,3-phenylene diisocyanate, 1,5-napthalene diisocyanate, bis-(4-isocyanatocyclohexyl)-methane, 4,4'-diisocyanatodiphenyl ether and the like.
  • Typical trifunctional isocyanates that can be used are triphenylmethane triisocyanate, 1,3,5-benzene triisocyanate, 2,4,6-toluene triisocyanate and the like, Trimers of diisocyanates also can be used such as the trimer of hexamethylene diisocyanate which is sold under the tradename "Desmodur”® N-3390 and the trimer of isophorone diisocyanate. Trifunctional adducts of triols and diisocyanates can be used.
  • Optional Ingredients are triphenylmethane triisocyanate, 1,3,5-benzene triisocyanate, 2,4,6-toluene triisocyanate and the like. Trimers of diisocyanates also can be used such as the trimer of hexamethylene diisocyanate which is sold under the tradename "Desmodur”® N-3390 and the trimer of isophorone diisocyanate. Trifunctional
  • the present coating composition can further comprise a functional amount of catalyst, generally about 0.1 to 5 weight percent, based on the weight of solids in the formulation.
  • catalysts can be used, such as dibutyl tin dilaurate or tertiary amines such as triethylenediamine. These catalysts can be used alone or in conjunction with carboxylic acids such as acetic acid. It is preferred that a catalyst be employed.
  • the coating compositions of the present invention are formulated into high solids coating systems dissolved in at least one solvent.
  • the solvent is usually organic.
  • Preferred solvents include aromatic hydrocarbons such as petroleum naphtha or xylenes; ketones such as methyl amyl ketone, methyl isobutyl ketone, methyl ethyl ketone or acetone; esters such as butyl acetate or hexyl acetate; and glycol ether esters such as propylene glycol monomethyl ether acetate. It is preferred to employ solvent.
  • aromatic hydrocarbons such as petroleum naphtha or xylenes
  • ketones such as methyl amyl ketone, methyl isobutyl ketone, methyl ethyl ketone or acetone
  • esters such as butyl acetate or hexyl acetate
  • glycol ether esters such as propylene glycol monomethyl ether acetate. It is preferred to employ solvent.
  • the coating compositions of the present invention can also contain up to 40% of total binder of a dispersed acrylic component which is a polymer particle dispersed in an organic media, which particle is stabilized by what is known as steric stabilization.
  • a dispersed acrylic component which is a polymer particle dispersed in an organic media, which particle is stabilized by what is known as steric stabilization.
  • the dispersed phase or particle, sheathed by a steric barrier will be referred to as the "macromolecular polymer” or "core”.
  • the stabilizer forming the steric barrier, attached to this core will be referred to as the "macromonomer chains" or "arms”.
  • the dispersed polymer contains about 10 to 90%, preferably 50 to 80%, by weight, based on the weight of the dispersed polymer, of a high molecular weight core having a weight average molecular weight of about 50,000 to 500,000.
  • the preferred average particle size is 0.1 to 0.5 microns.
  • the arms, attached to the core make up about 10 to 90%, preferably 10 to 59%, by weight of the dispersed polymer, and have a weight average molecular weight of about 1,000 to 30,000, preferably 1,000 to 10,000.
  • the macromolecular core of the dispersed polymer is comprised of polymerized acrylic monomer(s) optionally copolymerized with ethylenically unsaturated monomer(s).
  • Suitable monomers include styrene, alkyl acrylate or methacrylate, ethylenically unsaturated monocarboxylic acid, and/or silane- containing monomers.
  • Such monomers as methyl methacrylate contribute to a high Tg (glass transition temperature) dispersed polymer, whereas such "softening" monomers as butyl acrylate or 2-ethylhexylacrylate contribute to a low Tg dispersed polymer.
  • the macromolecular core can be crosslinked through the use of diacrylates or dimethacrylates such as allyl methacrylate or post reaction of hydroxyl moieties with polyfunctional isocyanates.
  • the macromonomer arms attached to the core can contain polymerized monomers of alkyl methacrylate, alkyl acrylate, each having 1 to 12 carbon atoms in the alkyl group, as well as glycidyl acrylate or glycidyl methacrylate or ethylenically unsaturated monocarboxylic acid for anchoring and/or crosslinking.
  • useful hydroxy-containing monomers are hydroxy alkyl acrylates or methacrylates as described above.
  • Additional crosslinkers can be included in this formula such as aldemine, including the reaction product of isobutyraldehyde with diamines such as isophorone diamine and the like; ketimines such as the reaction product of methyl isobutyl ketone with diamines such as isophorone diamine; and polyaspartic esters.
  • the coating compositions of the present invention can also contain conventional additives such as pigments, stabilizers, ultraviolet light stabilizers, antioxidants, rheology control agents, flow agents, toughening agents and fillers. Such additional additives will, of course, depend on the intended use of the coating composition. Fillers, pigments, and other additives that would adversely effect the clarity of the cured coating will not be included if the composition is intended as a clear coating.
  • the coating compositions of the present invention can also an acrylic polymer of weight average molecular weight greater than 3,000, or a conventional polyester such as SCD® - 1040 from Etna Product Inc. for improved properties and appearance, sag resistance, flow and leveling and such.
  • the acrylic polymer can be composed of typical monomers such as acrylates, methacrylates, styrene and the like and functional monomers such as hydroxy ethyl acrylate, glycidyl methacrylate, or the like.
  • hydroxyl-functional oligomers that can be employed as component A(ii) include the reaction product of multifunctional alcohols such as pentaerythritol, hexanediol, trimethylol propane, and the like, with cyclic monomeric anhydrides such as hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, and the like, said reaction product further extended by reaction with monofunctional epoxies such as butylene oxide, propylene oxide, and the like to form hydroxyl oligomers.
  • multifunctional alcohols such as pentaerythritol, hexanediol, trimethylol propane, and the like
  • cyclic monomeric anhydrides such as hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, and the like
  • monofunctional epoxies such as butylene oxide, propylene oxide, and the like to form hydroxyl oligomers.
  • Non-alicyclic oligomers can include succinic anhydride- or phthalic anhydride-derived moieites such as described above.
  • Caprolactone oligomers which can be made by reacting caprolactone with a cycloaliphatic, aliphatic or aromatic polyol can also be used. Particulary useful caprolactone oligomers are described in columns 4 to 5 of U.S. Patent 5,286,782.
  • Preferred oligomers A(ii) have weight average molecular weights not exceeding about 3,000 with a polydispersity not exceeding about 1.7; more preferred oligomers have molecular weights not exceeding about 2,500 and polydispersity not exceeding about 1.4; most preferred oligomers have molecular weights not exceeding about 2,200, and polydisperity not exceeding about 1.25.
  • the coating compositions are typically applied to a substrate by conventional techniques such as spraying, electrostatic spraying, roller coating, dipping or brushing.
  • the present formulations are particularly useful as a clear coating for outdoor articles, such as automobile and other vehicle body parts.
  • the substrate is generally prepared with a primer and/or a color coat or other surface preparation prior to coating with the present compositions.
  • the present compositions can be cured by heating to a temperature of about 120° to 150°C for a period of about 15 to 90 minutes or with the proper formulation can be cured at ambient conditions (about 60° to 110°F, depending on the geographical location, usually 65° to 90°F).
  • the performance characteristics of the final cured coating composition are excellent, providing a combination of excellent gloss and durability to abrasion, sunlight and acidic rain. At the same time, the compositions provide low volatile organic content and ease of handling. The ability to apply the present compositions by spraying techniques with the unusually low VOC content is surprising.
  • Tinuvin®384 UVA substituted benzotriazole (Ciba-Geigy) Tinuvin®292 (HALS) hindered amine derivative (Ciba-Geigy)
  • Tolonate®HDT or HDT-LV isocyanurate oligomers of hexamethylene diisocyanate (Rhone-Poulenc)
  • Tinuvin®384 UV Screener from Ciba-Geigy 11.01
  • Tinuvin®292 Hindered Amine Light Stabilizer from Ciba-Geigy
  • B YK-301 ® flow additive from B YK Chemie
  • Tinuvin®384 UV Screener from Ciba-Geigy
  • Tinuvin®292 Hindered Amine Light Stabilizer from Ciba-Geigy
  • BYK-301® flow additive from BYK Chemie
  • Tolonate HDT-LV® (Isocyanurate trimer of hexamethylene diisocyanate from Rhone-Poulenc) 335.92
  • the components are mixed, the clear is then thinned to a Zahn #2 viscosity of 30 seconds with butyl acetate.
  • the clear is spray-applied over a black water-borne basecoat which has already received a warm air flash of 5 minutes at
  • the coating is cured for 30 minutes at 141°C (285°F). This coating exhibits excellent cure, hardness, and appearance.
  • Desmophen® XP-7069 (Aldimine from Bayer) 101.5 Tinuvin®384 (UV Screener from Ciba-Geigy) 10.64
  • Tinuvin®292 Hindered Amine Light Stabilizer from Ciba-Geigy 7.98
  • Tolonate HDT® (Isocyanurate trimer of hexamethylene diisocyanate from Rhone-Poulenc) 340.04 Components (i) and (B) are mixed, the clear is then thinned to a Zahn
  • This coating exhibits excellent cure, hardness, and appearance.
  • Tolonate HDT® (Isocyanurate trimer of hexamethylene diisocyanate from Rhone-Poulenc) 36.14
  • Components (i) and (B) are mixed.
  • the clear is drawn down over primed steel panels and TEDLAR® to a thickness of about 2 mils.
  • the coating is cured for 30 minutes at 141°C (285°F). This coating exhibits excellent cure, hardness, mar resistance, and appearance.
  • the percent gel fraction as measured by boiling the free film of this coating in acetone for 6 hours is 97.7%, which is excellent.
  • This same coating was cured at ambient conditions and found to give good hardness, appearance and cure.
  • the gel fraction on the air dried system after 30 days of room temperature aging was 94.7%.
  • the "surface dry time" as measured by a BK dry time tester was 260 minutes.
  • Tolonate HDT® (Isocyanurate trimer of hexamethylene diisocyanate from Rhone-Poulenc) 35.86
  • Components (i) and (B) are mixed.
  • the clear is drawn down over primed steel panels and TEDLAR® to a thickness of about 2 mils.
  • the coating is cured for 30 minutes at 141°C (285°F). This coating exhibits excellent cure, hardness, and appearance.
  • the gel fraction as measured by boiling the free film of this coating in acetone for 6 hours is 96.2%.
  • Sorbitol Ether Epoxy-hydroxyl from Dixie Chemical 2 ⁇ nd 3 -Surface dry time using BK dry time tester

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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)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

L'invention concerne une composition de revêtement durcissable comprenant, dans un solvant organique, un liant composé comme suit : (i) oligomère non isocyanate ou mélange d'oligomères ayant au moins deux groupes fonctionnels dont l'un est au moins un groupe époxyde, les autres étant époxyde ou hydroxyle; (ii) éventuellement polyester, oligoester ou polymère acrylique ayant au moins deux groupes hydroxyle; et (iii) réticulant oligomère ou mélange de réticulants ayant au moins deux groupes isocyanate.
EP98935946A 1997-07-24 1998-07-23 Systemes oligomeres epoxyde/isocyanate Withdrawn EP0998507A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US5355697P 1997-07-24 1997-07-24
US53556P 1997-07-24
PCT/US1998/015230 WO1999005193A1 (fr) 1997-07-24 1998-07-23 Systemes oligomeres epoxyde/isocyanate

Publications (1)

Publication Number Publication Date
EP0998507A1 true EP0998507A1 (fr) 2000-05-10

Family

ID=21985085

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98935946A Withdrawn EP0998507A1 (fr) 1997-07-24 1998-07-23 Systemes oligomeres epoxyde/isocyanate

Country Status (10)

Country Link
EP (1) EP0998507A1 (fr)
JP (1) JP2001510867A (fr)
KR (1) KR20010022142A (fr)
AU (1) AU741972B2 (fr)
BR (1) BR9810777A (fr)
CA (1) CA2297808A1 (fr)
IL (1) IL133924A (fr)
NZ (1) NZ502717A (fr)
TW (1) TWI239966B (fr)
WO (1) WO1999005193A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7144526B2 (en) * 2003-02-04 2006-12-05 E.I. Du Pont De Nemours And Company Conductive primer composition for ambient cure
WO2007136645A2 (fr) 2006-05-16 2007-11-29 E. I. Du Pont De Nemours And Company Composition de revêtement hautement productive pour retouche de carrosserie

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169825A (en) * 1975-05-15 1979-10-02 The Sherwin-Williams Company High solids coating compositions
US4409381A (en) * 1981-12-28 1983-10-11 Ford Motor Company Novel diblocked diisocyanate urea urethane oligomers and coating compositions comprising same
US4749743A (en) * 1986-10-06 1988-06-07 Ppg Industries, Inc. Epoxy-functional polyurethanes and high solids thermosetting coating compositions thereof
JPS6465179A (en) * 1987-09-04 1989-03-10 Nippon Paint Co Ltd Coatings composition for rustpreventive steel sheet having thin coating film

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9905193A1 *

Also Published As

Publication number Publication date
BR9810777A (pt) 2000-09-19
JP2001510867A (ja) 2001-08-07
AU8509298A (en) 1999-02-16
IL133924A (en) 2004-12-15
KR20010022142A (ko) 2001-03-15
CA2297808A1 (fr) 1999-02-04
AU741972B2 (en) 2001-12-13
IL133924A0 (en) 2001-04-30
NZ502717A (en) 2002-05-31
WO1999005193A1 (fr) 1999-02-04
TWI239966B (en) 2005-09-21

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