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US4578426A Expired / Lapsed US ⏱️ 0.0 years remaining

Production of coatings

Assignee: BASF SE
•
Filing: 1984-06-25
•
Granted: 1986-03-25
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Expires: 2004-06-25
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Abstract

Abstract A process for the production of coatings based on reaction products of (A) mixtures of (A1) polyhydroxypolyacrylate resins obtained from hydroxylalkyl esters of acrylic acid and/or methacrylic acid, alkyl esters of acrylic acid and/or methacrylic acid, and one or more polymerizable, olefinically unsaturated nitrogen-containing heterocyclic compounds, with or without vinylaromatics, (meth)acrylamides and other monomers, and (A2) polyesterpolyols with (B) isocyanurate-containing polyisocyanates which may or may not contain biuret groups, have a functionality of from 2.5 to 6 and possess predominantly cycloaliphatically bonded isocyanate groups, some of which may be replaced by aliphatically bonded isocyanate groups. The process is particularly useful for coating metal components.

Inventors

  • 👤 Werner Lenz
  • 👤 Hans Sander
  • 👤 Dieter Moeller

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 18:52
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/79; C08G18/791; C08G18/792; C08G18/28; C08G18/40; C08G18/4009; C08G18/4063; C08G18/62; C08G18/6283; C08G18/721; C09; C09D; C09D133/00; C09D133/04; C09D133/14

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 782 words
A process for the production of a coating based on a reaction product of (A) a mixture of (A1) a polyhydroxypolyacrylate resin obtained from an ester of acrylic acid or methacrylic acid with a monofunctional aliphatic alcohol, or a mixture of esters of acrylic acid and mehtacrylic acid with monofuctional aliphatic alcohols, a monoester of acrylic acid or methacrylic acid with a polyfunctional aliphatic alcohol, or a mixture of monoesters of acrylic acid and methacrylic acid woth polyfunctional aliphatic alcohols, and other compolymerizable olefinically unsaturated monomers, and (A2) a polyesterpolyol whcih is soluble in organic solvents with (B) a polyisocyanate which is unblocked or partially or completely blocked with CH-, NH- or OH-acidic blocking agents, contains isocyanurate groups and may or may not contain biuret groups and has a functionality of from 2.5 to 6, wherein the polyhydroxypolyacrylate resin (A1) used comprises from 40 to 99% by weight of hydroxyl-containing copolymers consisting of (a) from 6 to 70% by weight of one or more esters of the formula ##STR9## where R is hydrogen or methyl and R' is a straight-chain or branched alkylene radical of 2 to 18 carbon atoms or alkylene of 7 to 17 carbon atoms which contains one, two or three cycloaliphatic groups, (b) from 0 to 50% by weight of one or more hydroxylalkyl esters of acrylic acid or methacrylic acid of the formula ##STR10## where R is hydrogen or methyl and R" is the alkyl radical of a branched aliphatic carboxylic acid of 4 to 26 carbon atoms, (c) from 10 to 50% by weight of one or more alkyl esters of acrylic acid or methacrylic acid, which form homopolymers having a glass transition temperature of from +5° to +120° C., (d) from 0 to 10% by weight of a vinylaromatic, (e) from 10 to 60% by weight of one or more alkyl esters or alkylglycol esters of acrylic acid or methacrylic acid, which form homopolymers which have a glass transition temperature of from -80° to +4.5° C., the alkylglycol esters containing not more than 2 ether oxygen bridges, (f) from 0 to 10% by weight of an acrylamide or a methacrylamide which may or may not be substituted at the amide nitrogen atom by one or two alkyl radicals of 1 to 8 carbon atoms which may or may not contain a carbonyl group, or by one or two phenyl radicals, (g) from 1 to 25% by weight of one or more polymerizable olefinically unsaturated heterocyclic compodnds of the formula ##STR11## where R 1 , R 2 and R 3 are each hydrogen, methyl, ethyl, a straight-chain or branched alkyl radical of 3 or 4 carbon atoms, or phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms or by halogen or nitro, or R 2 and R 3 can form an aromatic six-membered ring which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms or by halogen or nitro, which ring is fused to the heterocyclic ring and (h) from 0 to 20% by weight of monomers which are not included under (a) to (g) and whose copolymerized radicals are inert to isocyanate groups, with the proviso that the sum of the percentages stated under (a) and (b) is from 6 to 70, the sum of the percentages stated under (c), (d) and (g) is from 11 to 60, and the sum of the percentages of the components stated under (a) to (h) is 100, the polyesterpolyol (A2) used comprises from 1 to 60% by weight of a hydroxyl-containing polyester which has a hydroxyl number of from 30 to 500 and an acid number of from 0 to 30 and is soluble in conventional surface coating solvents or solvent mixtures which are inert to isocyanates and essentially contain one or more aromatic, halogen, ether, ester or keto groups, or several different groups from amongst these, and this polyesterpolyol (A2) can also contain as much as 10% by weight of a polyfunctional alcohol having a molecular 1 weight of from 62 to 300, with the proviso that the sum of the percentages stated under (A1) and (A2) is 100, and the polyisocyanate (B) used, which contains isocyanurate groups, may or may not contain biuret groups and has a functionality of from 2.5 to 6 comprises (B1) from 60 to 100% by weight of an isocyanurate-containing polyisocyanate which possesses predominantly cycloaliphatically bonded isocyanate groups, and (B2) from 0 to 40% by weight of a polyisocyanate which contains biuret or isocyanurate groups or both biuret and isocyanurate groups and possesses predominantly aliphatically bonded isocyanate groups, with the proviso that the sum of the percentages stated under (B1) and (B2) is 100.
Claim 2
Dependent Claim 782 words
A process for the production of a coating based on a reaction product of (A) a mixture of (A1) a polyhydroxypolyacrylate resin obtained from an ester of acrylic acid or methacrylic acid with a monofunctional aliphatic alcohol, or a mixture of esters of acrylic acid and mehtacrylic acid with monofuctional aliphatic alcohols, a monoester of acrylic acid or methacrylic acid with a polyfunctional aliphatic alcohol, or a mixture of monoesters of acrylic acid and methacrylic acid woth polyfunctional aliphatic alcohols, and other compolymerizable olefinically unsaturated monomers, and (A2) a polyesterpolyol whcih is soluble in organic solvents with (B) a polyisocyanate which is unblocked or partially or completely blocked with CH-, NH- or OH-acidic blocking agents, contains isocyanurate groups and may or may not contain biuret groups and has a functionality of from 2.5 to 6, wherein the polyhydroxypolyacrylate resin (A1) used comprises from 40 to 99% by weight of hydroxyl-containing copolymers consisting of (a) from 6 to 70% by weight of one or more esters of the formula ##STR9## where R is hydrogen or methyl and R' is a straight-chain or branched alkylene radical of 2 to 18 carbon atoms or alkylene of 7 to 17 carbon atoms which contains one, two or three cycloaliphatic groups, (b) from 0 to 50% by weight of one or more hydroxylalkyl esters of acrylic acid or methacrylic acid of the formula ##STR10## where R is hydrogen or methyl and R" is the alkyl radical of a branched aliphatic carboxylic acid of 4 to 26 carbon atoms, (c) from 10 to 50% by weight of one or more alkyl esters of acrylic acid or methacrylic acid, which form homopolymers having a glass transition temperature of from +5° to +120° C., (d) from 0 to 10% by weight of a vinylaromatic, (e) from 10 to 60% by weight of one or more alkyl esters or alkylglycol esters of acrylic acid or methacrylic acid, which form homopolymers which have a glass transition temperature of from -80° to +4.5° C., the alkylglycol esters containing not more than 2 ether oxygen bridges, (f) from 0 to 10% by weight of an acrylamide or a methacrylamide which may or may not be substituted at the amide nitrogen atom by one or two alkyl radicals of 1 to 8 carbon atoms which may or may not contain a carbonyl group, or by one or two phenyl radicals, (g) from 1 to 25% by weight of one or more polymerizable olefinically unsaturated heterocyclic compodnds of the formula ##STR11## where R 1 , R 2 and R 3 are each hydrogen, methyl, ethyl, a straight-chain or branched alkyl radical of 3 or 4 carbon atoms, or phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms or by halogen or nitro, or R 2 and R 3 can form an aromatic six-membered ring which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms or by halogen or nitro, which ring is fused to the heterocyclic ring and (h) from 0 to 20% by weight of monomers which are not included under (a) to (g) and whose copolymerized radicals are inert to isocyanate groups, with the proviso that the sum of the percentages stated under (a) and (b) is from 6 to 70, the sum of the percentages stated under (c), (d) and (g) is from 11 to 60, and the sum of the percentages of the components stated under (a) to (h) is 100, the polyesterpolyol (A2) used comprises from 1 to 60% by weight of a hydroxyl-containing polyester which has a hydroxyl number of from 30 to 500 and an acid number of from 0 to 30 and is soluble in conventional surface coating solvents or solvent mixtures which are inert to isocyanates and essentially contain one or more aromatic, halogen, ether, ester or keto groups, or several different groups from amongst these, and this polyesterpolyol (A2) can also contain as much as 10% by weight of a polyfunctional alcohol having a molecular 1 weight of from 62 to 300, with the proviso that the sum of the percentages stated under (A1) and (A2) is 100, and the polyisocyanate (B) used, which contains isocyanurate groups, may or may not contain biuret groups and has a functionality of from 2.5 to 6 comprises (B1) from 60 to 100% by weight of an isocyanurate-containing polyisocyanate which possesses predominantly cycloaliphatically bonded isocyanate groups, and (B2) from 0 to 40% by weight of a polyisocyanate which contains biuret or isocyanurate groups or both biuret and isocyanurate groups and possesses predominantly aliphatically bonded isocyanate groups, with the proviso that the sum of the percentages stated under (B1) and (B2) is 100.
Claim 3
Dependent Claim 25 words
The process of claim 1, wherein the cycloaliphatic isocyanurate-containing polyisocyanate (B1) used is a product obtained from 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate) as the diisocyanate monomer.
Claim 4
Dependent Claim 45 words
The process of claim 1, wherein a product which contains, as copolymerized units, from 60 to 99% by weight of isophorone diisocyanate and from 1 to 40% by weight of hexamethylene diisocyanate is used as the isocyanurate-containing polyisocyanate (B1) possessing predominantly cycloaliphatically bonded isocyanate groups.
Claim 5
Dependent Claim 33 words
The process of claim 3, wherein the polyisocyanate (B1) used contains, is copolymerized units, from 70 to 98% by weight of isophorone diisocyanate and from 2 to 30% by weight of hexamethylene diisocyanate.
Claim 6
Dependent Claim 34 words
The process as of claim 1, wherein a product obtained from hexamethylene diisocyanate, as the diisocyanate monomer, is used as the polyisocyanate (B2) which contains biuret groups and possesses predominantly aliphatically bonded isocyanate groups.
Claim 7
Dependent Claim 29 words
The process of claim 1, wherein a product obtained from hexamethylene diisocyanate, as the diisocyanate monomer, is used as the isocyanurate-containing polyisocyanate (B2) possessing predominantly aliphatically bonded cyanate groups.
Claim 8
Dependent Claim 18 words
The process of claim 1, wherein the hydroxyl number of the hydroxyl-containing copolymer (A1) is from 30to 250.
Claim 9
Dependent Claim 19 words
The process of claim 1, wherein the hydroxyl number of the hydroxyl-containing copolymer (A1) is from 50 to 150.
Claim 10
Dependent Claim 28 words
The process of claim 1, wherein hydroxyethyl acrylate or methacrylate, or a mixture of hydroxyethyl acrylate and hydroxyethyl methacrylate, is used as component (a) of the hydroxyl-containing copolymer.
Claim 11
Dependent Claim 36 words
The process of claim 1, wherein one or more compounds from the group consisting of butane-1,4-diol monacrylate, butane-1, 4-diol monomethacrylate, hexane-1, 6-diol monoacrylate and hexane-1, 6-diol monomethacrylate are used as component (a) of the hydroxyl-containing copolymer.
Claim 12
Dependent Claim 21 words
The process of claim 1, wherein from 2 to 20% by weight of component (g) is used for the hydroxyl-containing copolymer.
Claim 13
Dependent Claim 19 words
The process of claim 1, wherein the hydroxyl number of the soluble polyesterpolyol (A2) is from 50 to 400.
Claim 14
Dependent Claim 19 words
The process of claim 1, wherein the acid number of the soluble polyesterpolyol (A2) is from 0 to 15.
Claim 15
Dependent Claim 31 words
The process of claim 1, wherein the soluble polyesterpolyol (A2) is used in an amount of from 5 to 55% by weight, based on the total amount of the polyol (A).
Claim 16
Dependent Claim 14 words
The process of claim 1, wherein a branched polyesterol is used as component (A2).
Claim 17
Dependent Claim 19 words
The process of claim 1, wherein the hydroxyl number of the polyol mixture (A) is from 30 to 250.
Claim 18
Dependent Claim 19 words
The process of claim 1, wherein the hydroxyl number of the polyol mixture (A) is from 50 to 170.
Claim 19
Dependent Claim 57 words
The process of claim 1, wherein the ratio of the reactants (A) and (B) is cohsen so that the ratio of the number of equivalents of isocyanate groups which are unblocked or partially or completely blocked with CH-, NH- or OH-acidic blocking agents to the number of equivalents of reactive hydroxyl groups is from 0.25:1 to 4:1.
Claim 20
Dependent Claim 22 words
The process of claim 1, wherein a monofunctional ketoxime is used as the blocking agent for the partially or completely blocked polyisocyanate.
Claim 21
Dependent Claim 21 words
The process of claim 19, wherein dimethyl ketoxime or methyl ethyl ketoxime is used as the blocking agent for the polyisocyanate.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-03-24 1989-09-23 1990-03-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-03-24 1993-09-23 1994-03-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-03-24 1997-09-23 1998-03-25 $7700.00 Window Closed / Lapsed

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