EP0331682A1 - Composition de revetement a duree de vie en pot prolongee - Google Patents

Composition de revetement a duree de vie en pot prolongee

Info

Publication number
EP0331682A1
EP0331682A1 EP87907952A EP87907952A EP0331682A1 EP 0331682 A1 EP0331682 A1 EP 0331682A1 EP 87907952 A EP87907952 A EP 87907952A EP 87907952 A EP87907952 A EP 87907952A EP 0331682 A1 EP0331682 A1 EP 0331682A1
Authority
EP
European Patent Office
Prior art keywords
coating composition
component
composition according
tertiary
pot life
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.)
Pending
Application number
EP87907952A
Other languages
German (de)
English (en)
Inventor
Dieter Möller
Udo Vorbeck
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.)
BASF Farben und Fasern AG
Original Assignee
BASF Lacke und Farben 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 BASF Lacke und Farben AG filed Critical BASF Lacke und Farben AG
Publication of EP0331682A1 publication Critical patent/EP0331682A1/fr
Pending 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
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/089—Reaction retarding 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • C08G18/2835—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds having less than 5 ether groups

Definitions

  • the invention relates to a coating composition containing organic solvents, a mixture of a polyhydroxy component (A) and a polyisocyanate component (B) and an agent which extends the pot life, and the use of this coating composition, in particular for automotive refinishing.
  • 2-component polyurethane systems are used in the automotive industry, where they are used in automotive refinishing, for example.
  • a disadvantage of these known compositions is that the pot life of the compositions is too short, so that a reaction between the two components can take place during application to a substrate. This problem is exacerbated when a catalyst is used for polyurethane formation. It is therefore desirable that a two-component polyurethane composition have an extended pot life and that despite the extended pot life it can be cured quickly after application to a substrate.
  • tertiary alcohols as agents which extend pot life in a system which contains isocyanate groups and groups which are reactive with them. It is known from EP-B-1 304 that the pot life of a coating composition which contains a mixture of a polyhydroxy compound and a polyisocyanate in an organic solvent can be extended by adding 2-methyl-2-propanol and / or 2-methyl-2-butanol if at least 0.8 equivalents of the alcohol are used per equivalent of the polyisocyanate.
  • the object of the present invention was to effectively extend the pot life of the systems from combinations of polyols with carboxyl groups and polyisocyanates.
  • the coating composition of the type mentioned at the outset which is characterized in that the polyhydroxy component has an acid number of 5 to 25 mg KOH / g and a mixture of 0.1 to 4.0 wt. , based on the total weight of the coating composition, a compound having a tertiary amino group or an amide group (C) and 1 to 15% by weight, based on the total weight of the coating composition, of a tertiary monoalcohol (D), 2-methyl being the tertiary alcohols -2-propanol and 2-methyl-2-butanol are excluded.
  • Suitable polyhydroxy components with an acid number of 5 to 25 mg KOH / g are hydroxyacrylates, polyester polyols and polyether polyols.
  • the polyhydroxy compounds generally have a hydroxyl number of at least 80.
  • Suitable hydroxyacrylates are copolymers of styrene, vinyltoluene, acrylic acid, methacrylic acid, esters of maleic or fumaric acid, alkyl acrylates and alkyl methacrylates with 1 to 14 carbon atoms in the alkyl radical, such as, for example, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, isopropyl acrylate, isobutyl acrylate, isobutyl acrylate , 2-ethylhexyl acrylate, octyl acrylate, decyl acrylate, dodecyl acrylate, pentyl methacrylate, isoamyl methacrylate, hexyl methacrylate, 2-ethyl butyl methacrylate, octyl methacrylate, decyl methacrylate, decyl methacrylate,
  • Dodecyl methacrylate, methyl methacrylate and hydroxyl-containing esters of acrylic acid or methacrylic acid such as, for example, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, hydroxyamylacrylate, hydroxyhexyl acrylate, hydroxyoctyl acrylate, 2-hydroxypropyl acrylate,
  • the suitable hydroxyacrylates preferably have a hydroxyl number in the range from 80 to 750.
  • Suitable polyether polyols are, for example, polytetrahydrofuran diol and polypentane ether diol, and branched polyether polyols which are produced from a polyhydric alcohol and an alkylene oxide, such as ethylene oxide or propylene oxide.
  • the polyester polyols that can be used are produced by polycondensation of di- and / or polyvalent carboxylic acids, such as adipic acid, maleic acid, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, trimellitic acid, with di- and / or polyhydric alcohols, such as neopentyl glycol, glycerol and trimethylol propane, trimethylol propane .
  • the polyester polyols can also contain monohydric alcohols, such as, for example, benzyl alcohol, and / or monohydric carboxylic acids, such as, for example, senzoic acid.
  • the polylsocyanates which can generally have 2 to 4 isocyanate groups per molecule, can be aliphatic, cycloaliphatic or aromatic.
  • suitable polyfunctional isocyanates are 2,4-tolylene diisocyanate, 2,5-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, hexamethylene diisocyanate, 3,5,5-trimethyl-1-isocyanato-3-isocyanatomethylcyclohexane, m-xylylene diisocyanate, p-xylylene diisocyanate , Tetramethylene diisocyanate, cyclohexane-1,4-diisocyanate.
  • the polyisocyanates can be linked to prepolymers with a higher molecular weight.
  • examples include adducts of tolylene diisocyanate and trimethylol propane and the trimers of hexamethylene diisocyanate and isophorone diisocyanate.
  • the adduct of one molecule of pentaerythritol and 4 molecules of hexamethylene-1,6-diisocyanate may be mentioned as a suitable tetraisocyanate. Mixtures of the polyisocyanates can of course also be used.
  • Suitable solvents are ketones, ethers, esters and hydrocarbons.
  • the polyisocyanate component (B) advantageously has only secondary isocyanate groups which are substantially less reactive than primary isocyanate groups.
  • examples include the polyisocyanate polyisocyanates of isophorone diisocyanate, the reaction products of 3 moles of isophorone diisocyanate / and with 1 mole of water, the adducts of 3 moles of isophorone diisocyanate with 1 mole of a triol.
  • polylsocyanates with tertiary NCO groups can also be used.
  • Tertiary substances containing nitrogen-based groups generally have an accelerating effect in polyisocyanate-curing systems. It was therefore particularly surprising and unpredictable that the combination of a compound with a tertiary amino group or an amide group with a tertiary monoalcohol leads to an effective pot life extension.
  • the compound (C) is advantageously selected from the group dimethylacetamide, dimethylcyclohexylamine,
  • the tertiary monoalcohols (D) advantageously have an evaporation number below 60. It is particularly advantageous if the tertiary monoalcohols (D) have a flash point above 21 ° C.
  • 1-Methoxy tert-butanol-2 (CAS Reg. No. 3587-64-2) is particularly preferably used as the tertiary monoalcohol, since this alcohol has a flash point of 26 ° C.
  • the polyhydroxy component (A) has an acid number in the range from 10 to 20 mg KOH / g.
  • (B) is preferably in the range of 0.5 to 2.
  • compositions of the invention can be any coating compositions of the invention.
  • Contain additives such as fillers, anti-settling agents and leveling agents as well as pigments and catalysts for the formation of polyurethane.
  • the coating compositions according to the invention can be applied to a substrate in various ways, for example by brushing, spraying, flooding, dipping, rolling or knife coating.
  • the organic solvents and the pot-lengthening agents evaporate during or after application to the substrate.
  • the coating agents are hardened at temperatures up to about 120 ° C.
  • the curing time which depends on the temperature, the catalyst used and of course the binder itself, is in the range of a few minutes to several days. Because of the possible low curing temperatures, the coating compositions according to the invention are advantageously used as automotive refinish paints.
  • pot life of two-component polyurethane lacquers can be extended considerably according to the invention, the pot life extensions being of the order of 4 hours and longer.
  • the pot life is defined as the time that leads to a doubling of the viscosity.
  • the solid line in the diagrams of Examples 1 to 20 illustrates the temporal viscosity curve of the corresponding two-component polyurethane system without the addition of the mixture of (C) and (D).
  • the percentages given in the examples are based on the total weight of the coating composition.
  • Example 1 Polyol component I isocyanate component (a) (Desmodur Z 4370) 0.3% dimethylacetamide
  • Isocyanate component (a) (Desmodur Z 4370)
  • Example 3 Polyol Component I Isocyanate Component (a) (Desmodur z 4370)
  • Example 4 Polyol component I isocyanate component (a) (Desmodur z 4370) 0.3% dimethylcyclohexylamine
  • Example 5 Polyol Component I Isocyanate Component (a) (Desmodur z 4370) 0.6% Dimethylcyclohexylamine
  • Example 7 Polyol component I isocyanate component (a) (Desmodur z 4370) 0.3% N-methylmorpholine
  • Example 8 Polyol component I isocyanate component (a) (Desmodur z 4370) 0.6% N-methylmorpholine
  • Example 9 Polyol component I isocyanate component (a) (Desmodur z 4370) 0.9% N-methylmorpholine
  • Example 10 Polyol Component II Isocyanate Component (a) (Desmodur z 4370) 0.3% Dimethtylacetamide
  • Example 11 Polyol component II isocyanate component (a) (Desmodur z 4370) 0.9% dimethylacetamide
  • Example 12 Polyol component II isocyanate component (a) (Desmodur z 4370) 0.3% dimethylcyclohexylamine
  • Example 13 Polyol component II isocyanate component (a) (Desmodur Z 4370) 0.6% dimethylcyclohexylamine
  • Example 14 Polyol component II isocyanate component (a) (Desmodur Z 4370) 0.9% dimethylcyclohexylamine
  • Example 15 Polyol component II isocyanate component (a) (Desmodur Z 4370) 0.3% N-methylmorpholine
  • Example 16 Polyol component II isocyanate component (a) (Desmodur Z 4370) 0.6% N-methylmorpholine
  • Example 17 Polyol component II isocyanate component (a) (Desmodur Z 4370) 0.9% N-methylmorpholine
  • Example 13 Polyol component I isocyanate component (b) (Desmodur N) 0.3% dimethylacetamide
  • Example 20 Polyol component I isocyanate component (b) (Desmodur N) 0.9% dimethylacetamide

Landscapes

  • 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)
  • Paints Or Removers (AREA)

Abstract

Composition de revêtement renfermant un solvant organique, un mélange d'un constituant polyhydroxy (A) et d'un constituant polyisocyanate (B) ainsi qu'un agent prolongeant la durée de vie en pot. Le constituant polyhydroxy présente un indice d'acidité compris entre 5 et 25 mg KOH/g, et on utilise comme agent prolongeant la durée de vie en pot un mélange composé de 0,1 à 4,0 % en poids, rapportés au poids total de la composition de revêtement, d'un composé avec un groupe amino tertiaire ou un groupe amide (C), et de 1 à 15 % en poids, rapportés au poids total de (A) et (B), d'un monoalcool tertiaire. Comme alcools tertiaires sont exclus le 2-méthyl-2-propanol et le 2-méthyl-2-butanol. Est également décrite l'utilisation des compositions de revêtement, notamment pour la peinture dans la réparation automobile.
EP87907952A 1986-11-20 1987-11-20 Composition de revetement a duree de vie en pot prolongee Pending EP0331682A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19863639637 DE3639637A1 (de) 1986-11-20 1986-11-20 Ueberzugszusammensetzung mit verlaengerter topfzeit
DE3639637 1986-11-20

Publications (1)

Publication Number Publication Date
EP0331682A1 true EP0331682A1 (fr) 1989-09-13

Family

ID=6314351

Family Applications (2)

Application Number Title Priority Date Filing Date
EP87117125A Expired - Lifetime EP0270892B1 (fr) 1986-11-20 1987-11-20 Composition de revêtement ayant une vie en pot prolongée
EP87907952A Pending EP0331682A1 (fr) 1986-11-20 1987-11-20 Composition de revetement a duree de vie en pot prolongee

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP87117125A Expired - Lifetime EP0270892B1 (fr) 1986-11-20 1987-11-20 Composition de revêtement ayant une vie en pot prolongée

Country Status (6)

Country Link
US (1) US4983703A (fr)
EP (2) EP0270892B1 (fr)
AT (1) ATE67772T1 (fr)
DE (2) DE3639637A1 (fr)
ES (1) ES2025616T3 (fr)
WO (1) WO1988003935A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4999213A (en) * 1990-02-21 1991-03-12 E. I. Du Pont De Nemours And Company Monofunctional alcohols to prevent gelation in two component isocyanate coatings
CN113831780A (zh) * 2021-08-25 2021-12-24 天津德威涂料化工有限公司 一种耐高湿聚氨酯腻子及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7710099A (nl) * 1977-09-15 1979-03-19 Akzo Nv Bekledingscompositie met verlengde verwer- kingstijd.
DE3523971A1 (de) * 1985-07-04 1987-01-08 Basf Farben & Fasern Rberzugszusammensetzung mit verlaengerter topfzeit

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8803935A1 *

Also Published As

Publication number Publication date
EP0270892B1 (fr) 1991-09-25
ATE67772T1 (de) 1991-10-15
ES2025616T3 (es) 1992-04-01
DE3639637A1 (de) 1988-05-26
DE3773349D1 (de) 1991-10-31
EP0270892A1 (fr) 1988-06-15
US4983703A (en) 1991-01-08
WO1988003935A1 (fr) 1988-06-02

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