CN110734693A - coating compositions - Google Patents
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- CN110734693A CN110734693A CN201810809380.1A CN201810809380A CN110734693A CN 110734693 A CN110734693 A CN 110734693A CN 201810809380 A CN201810809380 A CN 201810809380A CN 110734693 A CN110734693 A CN 110734693A
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- 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
- C09D175/02—Polyureas
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention relates to coating compositions comprising (a) an isocyanate-reactive component comprising (a1) at least days more aspartate and (a2) optionally polyether days aspartate, (b) an isocyanate component comprising (b1) at least an isocyanate prepolymer having an isocyanate group equivalent weight of 300-1100, and (b2) at least an isocyanate oligomer having not less than 2 isocyanate groups, the isocyanate prepolymer (b1) and isocyanate oligomer (b2) being present in a weight ratio of 1: 4 to 4: 1, (c) a catalyst, and (d) optionally a additive, the coating composition having a molar ratio of isocyanate groups to isocyanate-reactive groups of 1.5: 1 to 8: 1.
Description
Technical Field
The invention relates to coating compositions, a coating method and application of the coating compositions, and a product coated by using the coating compositions.
Background
The double-component coating containing the aspartate of has the advantages of weather resistance, wear resistance, humidity resistance, heat resistance and salt mist resistance, can meet the requirements of high solid content, low viscosity and environmental protection, is widely used in , and is particularly widely used as a floor finish in .
EP0573860B discloses two-component coatings comprising a polyisocyanate, an isocyanate-reactive component and a catalyst, wherein the equivalent ratio of isocyanate groups to isocyanate-reactive groups is from 0.8: 1 to 20: 1.
US2004067315A discloses two-component coatings comprising a prepolymer of isocyanate groups and an isocyanate-reactive component.
CN103834282A discloses weather-resistant anticorrosive polyurea coatings, which are composed of a component A and a component B, wherein the component A is composed of aliphatic polyisocyanate tripolymer and xylene, the component B is composed of modified dimeric type aspartate polyurea resin, a dispersing agent, a leveling agent, an antifoaming agent, an anti-settling agent, organic bentonite, a pigment, a filler, a delustering agent, xylene and propylene glycol monomethyl ether acetate, and the weight ratio of the component A to the component B is 1: 4.
The two-component coating has short working life, can be constructed only by using special spraying equipment, and increases the construction cost and difficulty.
The current method for prolonging the pot life mainly comprises 1) adding a large amount of reactive diluents or solvents into a coating formula to reduce the viscosity increase speed of the coating so as to ensure enough pot life, but many reactive diluents (such as vinylene carbonate) have toxicity determined by , and the addition of a large amount of reactive diluents or solvents causes additional environmental pollution and does not meet the trend and requirements of environmental protection, such as CN 106147560A; 2) selecting low-activity isocyanates, such as macromolecular prepolymers, to reduce the reaction so as to ensure enough pot life of the coating, but the viscosity of the -like low-activity macromolecular prepolymers is very high, which not only increases the difficulty of construction, but also slows down the drying speed of the coating, the hardness of the coating formed by the coating is low, and the coating surface can not be dried completely even for a long time, such as US20040067315A, CN 00894, US-A3428610 and WO 2007/039133.
Therefore, it is desirable to develop kinds of paints with long pot life, which form coatings with the advantages of fast drying and high hardness.
Disclosure of Invention
The object of the present invention is to provide coating compositions, a method for coating and the use of the coating compositions, and the products coated with the coating compositions.
The coating composition according to the present invention comprises:
(a) an isocyanate-reactive component comprising:
(a1) at least days aspartic esters, and
(a2) optionally polyether aspartate ;
(b) an isocyanate component comprising:
(b1) at least an isocyanate prepolymer having an isocyanate group equivalent weight of 300-1100, and
(b2) at least an isocyanate oligomer containing not less than 2 isocyanate groups,
the weight ratio of the isocyanate prepolymer (b1) to the isocyanate oligomer (b2) is 1: 4 to 4: 1;
(c) catalyst, and
(d) an optional additive;
the coating composition has a molar ratio of isocyanate groups to isocyanate-reactive groups of from 1.5: 1 to 8: 1.
According to aspects of the present invention, there is provided the use of a coating composition provided according to the present invention for protecting a substrate surface or a coating on a substrate surface.
According to a further aspect of the invention, coating methods are provided comprising the steps of applying a coating composition provided according to the invention to a substrate surface followed by curing and drying.
According to a further aspect of the invention, coated products are provided comprising substrate and a coating composition provided according to the invention applied to the substrate to cure and dry to form a coating.
The coating composition has long service life, and the coating formed by the composition has the advantages of quick drying and high hardness.
Detailed Description
The present invention provides coating compositions comprising:
(a) an isocyanate-reactive component comprising:
(a1) at least days aspartic esters, and
(a2) optionally polyether aspartate ;
(b) an isocyanate component comprising:
(b1) at least an isocyanate prepolymer having an isocyanate group equivalent weight of 300-1100, and
(b2) at least an isocyanate oligomer containing not less than 2 isocyanate groups,
the weight ratio of the isocyanate prepolymer (b1) to the isocyanate oligomer (b2) is 1: 4 to 4: 1;
c) catalyst, and
d) an optional additive;
the coating composition has a molar ratio of isocyanate groups to isocyanate-reactive groups of from 1.5: 1 to 8: 1. The invention also provides a coating method and application of the coating composition, and a product coated by using the coating composition.
Coating composition
Zerewitinov active hydrogen is defined with reference to the tenth edition of the Romp chemical dictionary (Romp encyclopedia of chemistry), Georg Thieme Verlag Stuttgart, 1996. generally, groups containing Zerewitinov active hydrogen include, but are not limited to, hydroxyl, amino, and thiol groups.
The coating composition described herein may comprise a two-component coating composition, the term two-component referring to a coating composition comprising at least two components that have to be stored in separate containers due to their mutual reactivity. When the two separate components are mixed and applied to a substrate, the two sets of minutes of mutually reactive compounds react to crosslink and form a cured coating.
The term "cure, dry" as used herein refers to the process by which a liquid coating composition passes from a liquid state to a cured state.
The term "independently" as used herein means that the identities of R may be the same or different.
The molar ratio of isocyanate groups and isocyanate-reactive groups of the composition is preferably from 1.5: 1 to 4: 1, most preferably from 1.9: 1 to 2.5: 1.
The isocyanate reactive groups may be hydroxyl, mercapto and amino groups, with secondary amino groups being most preferred.
The organic solvent content of the coating composition is preferably less than 60 g/L.
Isocyanate reactive component (a)
Douda aspartate (a1)
The term "polyamine" as used herein refers to compounds containing at least two free primary and/or secondary amino groups, and polyamines include polymers containing at least two pendant and/or terminal amino groups.
The multi-day aspartate is derived from a Michael addition reaction of a system comprising a polyamine and an ester.
The esters are preferably or more of the following maleic and fumaric esters.
The reaction to prepare the multi-day aspartate can be carried out without solvent or in the presence of a suitable solvent.
The solvent is preferably or more selected from the group consisting of alcohols, ethers, acetates and ketones.
The alcohol is preferably or more of methanol, ethanol, butyl glycol and propanol.
The acetate is preferably n-butyl acetate.
The ketone is preferably methyl ethyl ketone dioxane.
The multi-day aspartate (a1) preferably includes a multi-day aspartate conforming to formula I:
wherein the content of the first and second substances,
x represents an aliphatic residue and X represents a cyclic or acyclic,
R1and R2Independently of one another, are organic radicals which do not react with isocyanate groups at atmospheric pressure at temperatures of up to 100 ℃,
n is an integer of not less than 2.
The R is1And R2Each independently preferably an alkyl residue having 1 to 10 carbon atoms, most preferably or more of methyl, ethyl and butyl.
Said n is preferably an integer from 2 to 4, most preferably 2.
The aliphatic residue herein is preferably derived from an alcohol compound, preferably or more of ethylene glycol, 1, 2-dihydroxypropane, 1, 4-dihydroxybutane, 1, 6-dihydroxyhexane, 2, 4-and/or 2, 4, 4-trimethyl-1, 6-dihydroxyhexane, 1-hydroxy-3, 3, 5-trimethyl-5-hydroxymethylcyclohexane, 4, 4 '-dihydroxydicyclohexylmethane, 3' -dimethyl-4 ', 4' -dihydroxydicyclohexylmethane, 1, 5-dihydroxy-2-methylpentane, 1, 1, 1-trimethylolpropane and 2, 2-bis (hydroxymethyl) 1, 3-propanediol (pentaerythritol).
The aliphatic residues of the multi-day aspartate are preferably or more of straight chain alkyl residues, branched chain-containing alkyl residues and cycloalkyl residues, most preferably cycloalkyl residues.
The amount of the multi-day aspartate is preferably more than 50 wt% based on 100 wt% of the isocyanate-reactive component (a).
The amount of the multi-day aspartate is most preferably 65-100 wt%, based on 100 wt% of the isocyanate-reactive component (a).
The equivalent weight of the amino group of the multi-day aspartate is preferably 200-500.
The viscosity of the multi-day aspartate is preferably 500-4000 mpa.s.
When the multi-day aspartate has an n of 2, it is obtained from the reaction of a polyamine comprising the formula:
the polyamine is preferably or more selected from the group consisting of ethylenediamine, 1, 2-diaminopropane, 1, 4-diaminobutane, 1, 3-diaminopentane, 1, 6-diaminohexane, 2, 5-diamino-2, 5-dimethylhexane, 2, 4-trimethyl-1, 6-diaminohexane, 2, 4, 4-trimethyl-1, 6-diaminohexane, 1, 11-diaminodeca -ane, 1, 12-diaminododecane, 1, 3-cyclohexanediamine and 1, 4-cyclohexanediamine, amino-3, 3, 5-trimethyl-5-aminomethylcyclohexane, 2, 4-hexahydrotoluenediamine, 2, 6-hexahydrotoluenediamine, 2, 4 '-diamino-dicyclohexylmethane, 4, 4' -diamino-dicyclohexylmethane, 3 '-dialkyl-4, 4' -diaminodicyclohexylmethane, 2, 4, 4 '-triamino-5-methyldicyclohexylmethane, 2-methyl-1, 5-pentanediamine, 1, 3-diaminodiaminocyclohexane and 1, 3' -diamino-4, 4 '-dicyclohexylmethane, 3' -diaminodicyclohexylmethane, 4, 4 '-diaminodicyclohexylmethane, 3-4, 3-dimethyldicyclohexylmethane, 3-4' -diaminocyclohexane, 3-dimethylcyclohexane, 3-4-dimethylcyclohexane, 3-dimethylcyclohexane, 3-4-dimethylcyclohexane, 3-dimethylcyclohexane, 3-1, 3-dimethylcyclohexane, 6-3-1, 3-dimethylcyclohexane, 3-1, 6-1, 3-dimethylcyclohexane, 6-dimethylcyclohexane, 3-1, 6-dimethylcyclohexane, 3-1, 6-dimethylcyclohexane, 3-.
The maleate and/or fumarate is preferably or more of dimethyl maleate, diethyl maleate, dibutyl maleate, dimethyl fumarate, diethyl fumarate and dibutyl fumarate.
The temperature of the reaction is preferably 0 ℃ to 100 ℃.
The weight ratio of the maleic and/or fumaric esters to the polyamines is preferably 2: 1.
The weight ratio of the olefinic double bonds of the maleates and/or fumarates to the primary amino groups of the polyamines is preferably 1: 1.
The product obtained from the reaction is preferably purified by rectification.
The components of the reaction may or may not comprise a solvent, preferably a solvent.
The solvent is preferably or more selected from methanol, ethanol, propanol and dioxane.
The polyaspartic aspartate (a1) preferably includes or more polyaspartic (i) polyaspartic having the structure of formula II,
(ii) A polyaspartic acid ester of formula III , and
(iii) a polyaspartic acid ester of formula IV of ,
wherein R is1And R2Each independently of the following list, methyl, ethyl and butyl.
The R is1And R2Each independently most preferably ethyl.
Said polyaspartic acid ester of multiple is most preferably or more of the isocyanate-reactive components, Desmophen NH1220, Desmophen NH1420, Desmophen NH1520 NH and Desmophen NH1521 according to the description in US512617, US523674, US5489704, US5243012, US5736604, US6458293, US6833424, US7169876 or US 2006/0247371.
Polyether Tian aspartate (a2)
The amount of polyether tetraacetate is preferably less than 35% by weight, based on 100% by weight of the isocyanate-reactive component.
The amount of polyether urethane aspartate is most preferably 10-35 wt%, based on 100 wt% of the isocyanate-reactive component.
The polyether day preferably has an equivalent weight of 200-500 of the amino group of the aspartate.
The viscosity of the polyether aspartate is preferably 50-2000 mPa.s.
The polyether aspartate (a2) preferably comprises a polyether aspartate that conforms to formula V:
wherein Z represents an aliphatic residue,
R1and R2Independently of one another, are organic radicals which do not react with isocyanate groups at atmospheric pressure at temperatures of up to 100 ℃,
R3represents C1-C6The alkyl residue of (a) is,
n is an integer of not less than 2,
m is an integer of 1 to 5.
The R is1And R2Each independently preferably an alkyl residue having 1 to 10 carbon atoms, most preferably or more of methyl, ethyl and butyl.
The aliphatic residue of the polyether tetraacetate is preferably or more of a straight chain alkyl residue, a branched chain-containing alkyl residue and a cycloalkyl residue.
The polyether aspartate is preferably obtained by the Michael addition reaction of a system comprising a polyetheramine and a dialkyl maleate.
The polyether urethane aspartate is preferably obtained by the reaction of a polyether polyamine comprising the formula:
wherein p is an integer of not less than 2, further steps are preferably 2 to 35, more preferably 2 to 8, most preferably 2.5 to 6.1, R1And R2Independently of one another, are organic radicals which do not react with isocyanate groups at atmospheric pressure at temperatures of up to 100 ℃,
R4and R5Each independently kinds or more of a hydrogen atom and a C group1-C4Alkyl residue of (A), R6And R7Each independently or more of hydrogen and an isocyanate non-reactive organic group.
The R is1And R2Each independently preferably an alkyl residue having 1 to 10 carbon atoms, most preferably or more of methyl, ethyl and butyl.
The R is4And R5Most preferably kinds or more of a hydrogen atom and a methyl group, each independently.
The R is6And R7Each independently preferablyAnd (3) hydrogen.
The number average molecular weight of the polyetherpolyamines is preferably from 100g/mol to 1000g/mol, most preferably from 148g/mol to 600 g/mol.
The polyether polyamine is preferably an aliphatic polyether polyamine comprising a primary amino group, such as Jeffamine polyether polyamine, available from Huntsman Corporation, The Woodlands, TX.
The polyetherpolyamine is preferably a mixture of polyetherpolyamines having an average value of p of 2.5 and polyetherpolyamines having an average value of p of 6.1.
The amount of the polyetherpolyamine in which the average value of p is 2.5 is 50 to 99% by weight, preferably 50 to 90% by weight, most preferably 80 to 90% by weight, based on 100% by weight of the polyetherpolyamine.
The amount of the polyetherpolyamine in which the average value of p is 6.1 is 1 to 50% by weight, preferably 10 to 50% by weight, most preferably 10 to 20% by weight, based on 100% by weight of the polyetherpolyamine.
The maleate and/or fumarate preferably contains groups of dimethyl ester, diethyl ester, dibutyl ester, diamyl ester, di-2-ethylhexyl ester, substituted by methyl in the 2-position and substituted by methyl in the 3-position.
The dibutyl esters are preferably or more of di-n-butyl, di-sec-butyl and di-tert-butyl esters.
The maleate and/or fumarate esters are most preferably or more of dimethyl maleate, diethyl maleate, dibutyl maleate, dimethyl fumarate, diethyl fumarate and dibutyl fumarate.
The component for preparing the polyether aspartate (a2) preferably further comprises a polyether polyamine corresponding to the formula :
wherein Y' is kinds or more of a straight chain alkyl residue, a branched chain-containing alkyl residue and a cycloalkyl residue,
q is an integer of 1 to 35,
R8is provided with C1-C6An alkyl residue of (2).
The polyether aspartate (a2) preferably includes a polyether aspartate that conforms to formula VI:
wherein r is an integer of 2 to 4,
q is an integer of 1 to 35,
y' is an alkyl residue of a compound represented by formula (I),
R1and R2Independently of one another, are organic radicals which do not react with isocyanate groups at atmospheric pressure at temperatures of up to 100 ℃,
R8is provided with C1-C6An alkyl residue of (2).
Said q is preferably an integer from 1 to 8, most preferably an integer from 1 to 5.
The R is1And R2Each independently preferably an alkyl residue having 1 to 10 carbon atoms, most preferably or more of methyl, ethyl and butyl.
The Y 'is preferably kinds or more of a straight-chain alkyl residue, a branched-chain-containing alkyl residue and a cycloalkyl residue, and most preferably kinds or more of ethyl, propyl, butyl, hexyl, cyclohexyl, dicyclohexylmethyl, 3' -dimethyldicyclohexylmethyl, 2-methylpentyl, 1, 1, 1-tri (methyl) propyl and 2, 2-bis (methyl) propyl.
R8 is preferably or more of methyl, ethyl and butyl.
The polyetheraspartic acid ester is most preferably Desmophen NH2850 XP, available from ColtsingChu, Lewakusen, Germany.
Isocyanate component (b)
The isocyanate groups of the compositions of the present invention include free and potentially free isocyanate groups.
Isocyanate prepolymer (b1)
The isocyanate group functionality of the isocyanate prepolymer is preferably from 1.9 to 4.5, most preferably 2.
The isocyanate group content of the isocyanate prepolymer is preferably 1 to 40% by weight, most preferably 1 to 20% by weight, based on 100% by weight of the isocyanate prepolymer.
The viscosity of the isocyanate prepolymer is preferably 1000-10000 mPas.
The isocyanate prepolymer is preferably the reaction product of a system comprising isocyanate monomers and/or isocyanate oligomers and a polyol.
The NCO/OH molar ratio of the reaction for preparing the isocyanate prepolymer is preferably from 1.1: 1 to 40: 1, most preferably from 2: 1 to 25: 1.
The excess isocyanate monomer of the reaction for preparing the isocyanate prepolymer may be removed by distillation to obtain a prepolymer free of monomer.
The isocyanate monomer preferably has an isocyanate functionality of not less than 2.
The isocyanate monomer is preferably or more selected from aliphatic isocyanate, aromatic isocyanate and alicyclic isocyanate.
The aliphatic isocyanate is preferably or more of Hexamethylene Diisocyanate (HDI), 2-dimethylpentanedionate, 2, 4-trimethylhexamethylene diisocyanate, butene diisocyanate, 1, 3-butadiene-1, 4-diisocyanate, 2, 4, 4-trimethyl-1, 6-hexamethylene diisocyanate, bis (isocyanatoethyl) carbonate, bis (isocyanatoethyl) ether and lysine methyl ester diisocyanate, most preferably hexamethylene diisocyanate.
The cycloaliphatic isocyanates are preferably or more of isophorone diisocyanate (IPDI), isomeric bis (4, 4' -isocyanatocyclohexyl) methanes or mixtures thereof in any isomer content, 1, 4-cyclohexylene diisocyanate, 1, 3-bis (isocyanatomethyl) benzene (XDI), 1, 3-and/or 1, 4-bis (2-isocyanatoprop-2-yl) -benzene (TMXDI), norbornane diisocyanate (NBDI), hydrogenated xylylene diisocyanate (H6XDI), 1, 4-cyclohexyl diisocyanate (H)6PPDI), 1, 5-Pentamethylene Diisocyanate (PDI) and dicyclohexylmethane diisocyanate, most preferably isophorone diisocyanate.
The aromatic isocyanate is preferably Toluene Diisocyanate (TDI).
The polyol is preferably or more of high molecular weight polyol and low molecular weight polyol, and further step is preferably or more of polyether polyol, polyester polyol and polycarbonate polyol, most preferably polyether polyol and/or polyester polyol.
The molecular weight of the polyol is preferably greater than 300g/mol, further steps are preferably greater than 500g/mol, most preferably 500-.
The polyol preferably contains 2 to 6 hydroxyl functional groups, most preferably 2 to 3 hydroxyl functional groups.
The isocyanate prepolymer preferably contains groups of urethane and allophanate groups.
Isocyanate oligomer (b2)
The isocyanate oligomer is preferably obtained by Oligomerization (Oligomerization) of a system comprising or more components selected from the group consisting of 1, 4-diisocyanatobutane, 1, 5-diisocyanatopentane, 1, 6-diisocyanatohexane (HDI), 1, 5-diisocyanato-2, 2-dimethylpentane, 2, 4-or 2, 4, 4-trimethyl-1, 6-diisocyanatohexane, 1-isocyano-3, 3, 5-trimethyl-5-isocyanomethylcyclohexane (IPDI), 1-isocyano-1-methyl-4- (3) -isocyanomethylcyclohexane, bis (4) -isocyanocyclohexylmethane, 2, 4-or 4, 4-diisocyanatocyclohexylmethane, 1, 10-diisocyanato-decane, 1, 12-diisocyanatododecane, 1, 3-or 1, 4-cyclohexane diisocyanate, m-xylylene diisocyanate and isomers thereof, 4-isocyanomethyl-1, 8-octanediisocyanate (TIN), 2, 4-isocyano-diisocyanate, 2, 6-diisocyanatotoluene, 2 '-diphenylmethane and 2, 4' -diisocyanatotoluene.
When the system for preparing the isocyanate oligomer comprises 2, 6-diisocyanotoluene, the amount of the 2, 6-diisocyanotoluene is preferably not less than 35% by weight based on 100% by weight of the system.
The oligomerization reaction can be carbodiimidization, dimerization, trimerization, biuretization, ureidoization, urethanization, allophanatization or cyclization to form oxadiazine groups, which reactions typically occur simultaneously or in succession.
The isocyanate oligomer preferably contains or more groups selected from the group consisting of iminooxadiazinedione, isocyanurate, uretdione, urethane, allophanate, biuret, urea, oxadiazinetrione, oxazolidone, acyl urea and carbodiimide groups, and most preferably or more groups selected from the group consisting of allophanate groups, biuret groups, uretdione groups, isocyanurate groups and iminooxadiazinedione groups.
The isocyanate oligomer having not less than 2 isocyanate groups is preferably or more of aliphatic triisocyanate, alicyclic triisocyanate, araliphatic triisocyanate, aromatic triisocyanate and their derivatives having iminooxadiazinedione, isocyanurate, uretdione, urethane, allophanate, biuret, urea, oxadiazinetrione, oxazolidone, acylurea and/or carbodiimide groups, further steps are preferably aliphatic triisocyanate, alicyclic triisocyanate, araliphatic triisocyanate, derivatives having allophanate, biuret, uretdione, isocyanurate and/or iminooxadiazinedione groups of aromatic triisocyanate, further preferably aliphatic triisocyanate, derivatives having allophanate, biuret, uretdione, isocyanurate and/or iminooxadiazinedione groups of alicyclic triisocyanate, and most preferably or more of Desmodur N2580, Desmodur N3200, Desmodur N3400, Desmodur N3600 and Desmodur N3900.
The isocyanate group content of the isocyanate oligomer is preferably 10 to 50% by weight, most preferably 20 to 35% by weight, based on 100% by weight of the isocyanate oligomer.
The isocyanate oligomer preferably has an isocyanate group functionality of 2 to 4.
The viscosity of the isocyanate oligomer is preferably 100-4000 mPas.
The weight ratio of the isocyanate prepolymer to the isocyanate oligomer is preferably from 1: 4 to 2: 1, most preferably from 1: 2 to 1: 1.
The sum of the amounts of the isocyanate-reactive component (a) and the isocyanate component (b) is preferably 94 to 100% by weight, based on 100% by weight of the composition.
Catalyst (c)
The catalyst may be a catalyst capable of accelerating the reaction of isocyanate groups with moisture, such as water.
The catalyst is preferably or more of tertiary amines and metal salts, most preferably tertiary amines.
The tertiary amine catalyst is preferably or more of triethylamine, dimorpholinodiethyl ether, N-dimethylaminocyclohexane, tris- (dimethylaminomethyl) phenol, 1, 3, 5-tris (dimethylaminopropyl) hexahydrotriazine, bis (dimethylaminoethyl) ether, and 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol.
The metal salt is preferably or more of ferric chloride, zinc chloride, bismuth isooctanoate, and bismuth carboxylate.
The amount of the catalyst is preferably 0.001 to 5% by weight, further steps preferably 0.01% to 3% by weight, particularly preferably 0.1 to 1.5% by weight, most preferably 0.15% to 0.35% by weight, based on the amount of the isocyanate mixture being 100% by weight.
Additive (d)
The additives are preferably or more of wetting agents, dispersants, matting agents, defoamers, film formers, thickeners, elastomers, pigments, leveling agents and other additives known to those skilled in the art that can be added to the coating composition.
The amount of the additive may be an amount that can be added as is well known to those skilled in the art.
The pot life of the coating composition is preferably more than 40 minutes.
Use of
Base material
The substrate may be artificial stone, wood, artificial wood, marble, terrazzo, ceramic, linoleum, metal, mineral material, plastic, rubber, concrete, composite board, paper, leather or glass.
The plastic is preferably a polyethylene resin or a polypropylene resin.
The substrate may be pre-treated, preferably sanded or coated.
Coating method
The curing and drying temperature is preferably 25 +/-2 ℃, and the humidity is preferably 60 +/-10%.
The application may be by methods well known to those skilled in the art, such as knife coating, dipping, brushing, rolling, spraying or curtain coating.
Coated product
The coated product is preferably a floor.
The thickness of the coating is preferably 60 to 150 μm.
The coating may be single or multi-layered.
Examples
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In the event that a definition of a term in this specification conflicts with a meaning commonly understood by those skilled in the art to which the invention pertains, the definition set forth herein shall govern.
Unless otherwise indicated, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood as being modified by the term "about". Accordingly, unless indicated to the contrary, the numerical parameters set forth herein are approximations that can vary depending upon the desired properties to be obtained.
As used in this specification, unless otherwise indicated, "," , "" , "and" the "are intended to include" at least "or" or more.
As used herein, "and/or" means or all of the elements mentioned.
As used herein, "comprising" and "comprises" encompass the presence of only the recited elements as well as the presence of other, non-recited elements in addition to the recited elements.
All percentages in the present invention are by weight unless otherwise indicated.
The analytical measurements according to the invention were carried out at 25. + -. 2 ℃ and 60. + -. 10% humidity, unless otherwise stated.
The number average molecular weight was determined by gel permeation chromatography using tetrahydrofuran as the mobile phase against polystyrene standards at 23 ℃.
The isocyanate group (NCO) content is determined volumetrically according to DIN-EN ISO 11909 and the data determined include the free and potentially free NCO content.
Isocyanate functionality was determined according to GPC.
Amino group content was determined according to AFAM 2011-06054.
The viscosity of the individual components was measured at 25. + -. 2 ℃ according to DIN 53019 using a Brookfield DV-II + Pro. rotational viscometer.
V5minDenotes the viscosity of the coating composition after storage for 5 minutes at room temperature, and so on, V10min，V15min，V20min，V25min，V30min，V35min，V40min，V45minThe viscosities of the coating compositions after storage at room temperature for 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 35 minutes, 40 minutes and 45 minutes, respectively, are shown.
Surface drying time: the time taken from application of the composition to the surface of the glass until the coating dries is considered to be the open time, as determined in accordance with GB/T13477.5-2002, when the coated surface is touched with a finger, if it feels tacky, but no coating sticks to the finger.
And (3) measuring the hardness of the coating by adopting a BYK swing rod hardness tester, wherein the swing rod hardness (1d) refers to the hardness of the swing rod after the coating is stored for days, and the swing rod hardness (7d) refers to the hardness of the swing rod after the coating is stored for seven days.
The working life is as follows: the time required when the viscosity of the coating composition reached 5 times the viscosity of the coating composition after 5 minutes storage. The longer the pot life, the longer the workable time of the coating composition.
Raw materials and reagents
Desmophen NH 1420: amino group functionality of 2.0, amino group equivalent of 279, viscosity of 900-2000mPa.s (25 ℃), available from Kostex, Inc., Germany.
Desmophen NH 2850: 295 equivalents of amino groups and a viscosity of > 80mPa.s (25 ℃) and is commercially available from Kostex Industrie GmbH, Germany.
Desmodur N3600: based on the aliphatic trimer of HDI, 100% by weight solids, NCO equivalent 183, NCO content 23.0 wt.%, HDI monomer content less than 0.25 wt.%, viscosity about 1200mPa · s (23 ℃), NCO functionality 3.0-3.5, available from kossi gmbh.
Desmodur N3900: based on HDI aliphatic trimer, 100% by weight solids, NCO content 23.5 wt.%, HDI monomer content less than 0.25 wt.%, viscosity about 730mPa · s (23 ℃), NCO functionality 3.0-3.5, available from korsin gmbh.
Desmodur N3200: an aliphatic biuret based on HDI having 100% by weight solids, an NCO content of 23 wt.%, an HDI monomer content of less than 0.4 wt.%, a viscosity of about 2500mPa · s (23 ℃), an NCO functionality of 3.0-3.5, available from corsin gmbh.
Desmodur XP 2840: allophanate based on HDI, 100% by weight solids, NCO content of 23 wt.%, HDI monomer content of less than 0.26 wt.%, viscosity of about 500mPa · s (23 ℃), NCO functionality of 2.5 to 3.0, commercially available from kossi gmbh.
Desmodur VL R21: MDI-based aromatic trimer having 100% by weight solids, an NCO content of 31.5 wt.%, a viscosity of about 200 mPa-s (23 ℃), an NCO functionality of 2.5-3.0, commercially available from kossi pioneer.
Desmodur E2863 XP: the reaction product of an aliphatic polyester polyol and HDI having an NCO equivalent weight of 380, an NCO content of 11.1 wt.%, an NCO functionality of about 2.0, an HDI monomer content of less than 0.3 wt.%, a viscosity of about 1350 mPa-s (23 ℃), is available from korse, inc.
Desmodur XP 2617: the reaction product of an aliphatic polyether polyol and HDI having an NCO equivalent weight of 336, an NCO content of 12.5 wt.%, an NCO functionality of about 2.0, an HDI monomer content of less than 0.5 wt.%, and a viscosity of about 4250 mPa-s (23 ℃), is available from corson corporation.
Desmodur VP LS 2371: the reaction product of an aliphatic polyether polyol and IPDI having an NCO equivalent weight of 1100, an NCO content of 3.7 wt.%, an NCO functionality of about 2.0, an IPDI monomer content of less than 2 wt.%, a viscosity of about 9800 mPa-s (23 ℃), is available from cockscomb incorporated.
Desmodur E15: the reaction product of an aliphatic polyether polyol and TDI having an NCO equivalent weight of 950, an NCO content of 4.4 wt.%, an NCO functionality of about 2.0, a TDI monomer content of less than 0.5 wt.%, a viscosity of about 7000 mPa-s (23 ℃), is available from cockscomb incorporated.
Desmodur E21: the reaction product of an aliphatic polyether polyol and MDI having an NCO equivalent weight of 263, an NCO content of 16.0 wt.%, an NCO functionality of about 2.0, and a viscosity of about 5400 mPa-s (23 ℃), commercially available from korsco, inc.
Polycat-41: tertiary amine catalysts, viscosity 33 mPas (25 ℃ C.), are commercially available from air chemistry.
BYK 085: silicone surface aids for solventless coatings are available from BYK Assistant.
BYK 331: silicone surface aids for solventless, solvent and water borne coatings and printing inks are available from BYK aids.
PGDA: low odor solvents, available from dow chemistry.
BA: volatile solvents are available from the national pharmaceutical group chemical company, ltd.
Viscosity, pot life and coating performance index reference values of coating compositions
Table 1 is the viscosity, pot life and coating performance index reference values for the coating compositions.
TABLE 1 viscosity, pot life and coating Performance index references for coating compositions
| Index (I) | Reference value |
| V5min | ＜800mpa·s |
| Pot life | ≥40min |
| Time to surface dry | ≤2h |
| Swing stem hardness (1d) | 40-200s |
| Swing stem hardness (7d) | 70-200s |
Method for preparing coating composition
The amounts of the components are shown in tables 2-6. the catalyst is added dropwise to the isocyanate-reactive component, stirred at room temperature for 10-30min to obtain a mixture A. the isocyanate prepolymer is added to the isocyanate oligomer, stirred at room temperature for 10-30min to obtain a mixture B. the additive is added dropwise to the mixture A, stirred at room temperature for 10-30min, allowed to stand for days, the mixture B is added, and stirred at room temperature for 3-5min to obtain the coating composition.
Method for producing a coating
The coating composition was applied to the glass surface using a 200 μm doctor blade with an application area of 15cm x 10cm, cured at 27 ℃ and 68% RH and dried to give a coating.
Examples 1-2 and comparative examples 1-9
Table 2 shows the components of the compositions of examples 1-2 and comparative examples 1-9, and the results of testing the compositions and their coatings.
Table 2 components and test results of compositions of examples 1-2 and comparative examples 1-9
Comparing examples 1, 2 and comparative examples 1-2, 7-8, the coating compositions have long pot life, short tack free time and good pendulum hardness when the isocyanate component of the coating composition comprises an isocyanate prepolymer and an isocyanate oligomer.
Comparing example 1 and comparative examples 3-4, the molar ratio of isocyanate groups to isocyanate-reactive groups of the coating composition of the present invention was 2.5 and the molar ratio of isocyanate groups to isocyanate-reactive groups of the comparative coating composition was 1.0, the pot life of the coating composition of the present invention was significantly better than that of the comparative coating composition.
Comparing example 2 with comparative example 9, the molar ratio of isocyanate groups and isocyanate-reactive groups of the coating composition of the present invention was 1.5 and the molar ratio of isocyanate groups and isocyanate-reactive groups of the comparative coating composition was 1.0, the pot life of the coating composition of the present invention was significantly better than that of the comparative coating composition.
Comparing example 1 and comparative examples 5-6, the coating compositions of the present invention have a weight ratio of isocyanate prepolymer to isocyanate oligomer in the range of 1: 4 to 4: 1, the weight ratio of the comparative coating compositions is less than 1: 4 or greater than 4: 1, and the pot life, open time and pendulum hardness of the coating compositions of the present invention are significantly better than those of the comparative coating compositions.
Example 3 and comparative examples 10 to 12
Table 3 shows the components of the compositions of example 3 and comparative examples 10 to 12, and the results of testing the compositions and their coatings.
Table 3 components and test results for the compositions of example 3 and comparative examples 10-12
Comparing example 3 and comparative examples 10-11, when the isocyanate component of the coating composition comprises an isocyanate prepolymer and an isocyanate oligomer, the coating composition has a long pot life, short tack free time and good pendulum hardness.
Comparing example 3 and comparative example 12, the coating composition had a molar ratio of isocyanate groups to isocyanate-reactive groups of 3.0 and the comparative coating composition had a molar ratio of isocyanate groups to isocyanate-reactive groups of 1.05, and the pot life of the coating composition of the present invention was significantly better than that of the comparative coating composition.
From example 3 it can be seen that when the isocyanate-reactive component of the composition comprises poly-d- aspartate (NH1420) and poly-d- aspartate (NH2850), the coating composition has a long pot life, short tack free time and good pendulum hardness.
Example 4 and comparative examples 13 to 18
Table 4 is the components of the compositions of example 4 and comparative examples 13-18, as well as the results of testing the compositions and their coatings.
Table 4 components and test results for the compositions of example 4 and comparative examples 13-18
Comparing example 4 with comparative examples 13-14, 16, the coating composition has a long pot life, short tack free time and good pendulum hardness when the isocyanate component of the coating composition comprises an isocyanate prepolymer and an isocyanate oligomer.
Comparing example 4 with comparative examples 15, 17, the coating compositions had a molar ratio of isocyanate groups and isocyanate-reactive groups of 4.0 and the comparative coating compositions had a molar ratio of isocyanate groups and isocyanate-reactive groups of 1.07, 1.02, respectively, the pot life of the coating compositions of the present invention was significantly better than that of the comparative coating compositions.
Comparing example 4 and comparative example 18, when the isocyanate prepolymer in the comparative composition has an isocyanate group equivalent weight of less than 300, the pot life of the coating composition is significantly shorter than that of the coating composition of the present invention.
From example 4 it can be obtained that when the isocyanate-reactive component of the composition comprises poly-d- aspartate (NH1420) and poly-d- aspartate (NH2850), the coating composition has a long pot life, short tack free time and good pendulum hardness.
Comparative examples 19 to 20
Table 5 shows the components of the compositions of comparative examples 19 to 20, and the results of the tests of the compositions and their coatings.
Table 5 Components and test results of the compositions of comparative examples 19-20
As can be seen from comparative examples 19 to 20, when the isocyanate oligomer in the isocyanate component is obtained by reacting an aromatic isocyanate, the pot life of the coating composition comprising the same is short, manual application is impossible, and the tack-free time of the coating layer formed from the coating composition is short.
Example 5 and comparative exampleExamples 21 to 24
Table 6 is the components of the compositions of example 5 and comparative examples 21-24, as well as the results of testing the compositions and their coatings.
Table 6 components and test results for the compositions of example 5 and comparative examples 21-24
Comparing example 5 and comparative examples 21-22, the coating compositions have long pot lives, short tack free times, and good pendulum hardness when the isocyanate component of the coating composition comprises an isocyanate prepolymer and an isocyanate oligomer.
Comparing example 5 and comparative examples 23-24, the coating compositions had a molar ratio of isocyanate groups to isocyanate-reactive groups of 2.5 and the comparative coating compositions had a molar ratio of isocyanate groups to isocyanate-reactive groups of 1.05, respectively, and the pot life of the coating compositions of the present invention was significantly better than that of the comparative coating compositions.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing description, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description; and therefore any changes which come within the meaning and range of equivalency of the claims are to be embraced within their scope.
Claims (23)
1, A coating composition comprising:
(a) an isocyanate-reactive component comprising:
(a1) at least days aspartic esters, and
(a2) optionally polyether aspartate ;
(b) an isocyanate component comprising:
(b1) at least an isocyanate prepolymer having an isocyanate group equivalent weight of 300-1100, and
(b2) at least an isocyanate oligomer containing not less than 2 isocyanate groups,
the weight ratio of the isocyanate prepolymer (b1) to the isocyanate oligomer (b2) is 1: 4 to 4: 1;
(c) catalyst, and
(d) an optional additive;
the coating composition has a molar ratio of isocyanate groups to isocyanate-reactive groups of from 1.5: 1 to 8: 1.
2. The composition of claim 1, wherein the polyaspartic ester (a1) comprises a polyaspartic ester according to formula I:
wherein the content of the first and second substances,
x represents an aliphatic residue and X represents a cyclic or acyclic,
R1and R2Independently of one another, are organic radicals which do not react with isocyanate groups at atmospheric pressure at temperatures of up to 100 ℃,
n is an integer of not less than 2.
3. The composition of claim 2, wherein the aliphatic residues of the multi-day aspartate (a1) are species or more of straight chain alkyl residues, branched chain-containing alkyl residues, and cycloalkyl residues.
4. The composition of claim 1, wherein the amount of the multi-day aspartate (a1) is greater than 50% by weight, based on 100% by weight of the isocyanate-reactive component (a).
5. The composition of claim 2, wherein n of the polyaspartic acid ester of (a1) is 2, resulting from the reaction of a polyamine comprising the formula:
6. the composition of claim 2, wherein the polyaspartic ester (a1) comprises or more polyaspartic esters of:
(i) a multi-day aspartate having a structure of formula II,
(ii) A polyaspartic acid ester of formula III , and
(iii) a polyaspartic acid ester of formula IV of ,
wherein R is1And R2Each independently of the following list, methyl, ethyl and butyl.
7. The composition of claim 1, wherein the polyether aspartate (a2) comprises a polyether aspartate conforming to formula V:
wherein Z represents an aliphatic residue,
R1and R2Each is independentThe organic group which does not react with isocyanate group under normal pressure and at 100 ℃ or lower,
R3represents C1-C6The alkyl residue of (a) is,
n is an integer of not less than 2,
m is an integer of 1 to 5.
8. The composition of claim 7, wherein the aliphatic residue of polyether sky aspartate (a2) is one or more of linear alkyl residues, branched alkyl residues, and cycloalkyl residues.
9. The composition of claim 1, wherein the polyether tetraacetate of (a2) is obtained from the reaction of a polyether polyamine comprising the formula:
wherein p is an integer of not less than 2,
R1and R2Independently of one another, are organic radicals which do not react with isocyanate groups at atmospheric pressure at temperatures of up to 100 ℃,
R4and R5Each independently kinds or more of a hydrogen atom and a C group1-C4The alkyl residue of (a) is,
R6and R7Each independently or more of hydrogen and an isocyanate non-reactive organic group.
10. The composition of claim 9, wherein component of the preparation of the polyether aspartate (a2) comprises a polyether polyamine corresponding to the formula:
wherein Y' is kinds or more of a straight chain alkyl residue, a branched chain-containing alkyl residue and a cycloalkyl residue,
q is an integer of 1 to 35,
R8is provided with C1-C6An alkyl residue of (2).
11. The composition of claim 1 or 10, wherein polyether aspartate (a2) comprises polyether aspartate according to formula VI:
wherein r is an integer of 2 to 4,
q is an integer of 1 to 35,
y' is an alkyl residue of a compound represented by formula (I),
R1and R2Independently of one another, are organic radicals which do not react with isocyanate groups at atmospheric pressure at temperatures of up to 100 ℃,
R8is provided with C1-C6An alkyl residue of (2).
12. The composition of claim 1 wherein said isocyanate prepolymer (b1) contains or more of urethane and allophanate groups.
13. The composition as claimed in claim 1, wherein the isocyanate group content of the isocyanate prepolymer (b1) is preferably 1 to 40% by weight, based on 100% by weight of the isocyanate prepolymer.
14. The composition of claim 1 wherein said isocyanate oligomer (b2) comprises or more of allophanate, biuret, uretdione, isocyanurate and iminooxadiazinedione groups.
15. The composition of claim 1 wherein the isocyanate oligomer (b2) is or more of derivatives of aliphatic and cycloaliphatic triisocyanates having allophanate, biuret, uretdione, isocyanurate and/or iminooxadiazinedione groups.
16. The composition as claimed in claim 1, wherein the isocyanate oligomer (b2) preferably has an isocyanate group content of 10 to 50% by weight, based on 100% by weight of the isocyanate oligomer.
17. The composition of claim 1, wherein the weight ratio of isocyanate prepolymer (b1) to isocyanate oligomer (b2) is from 1: 4 to 2: 1.
18. The composition of claim 1 wherein catalyst (c) is or more of a tertiary amine and a metal salt.
19. The composition of any one of claims 1-18 and , wherein the composition has a molar ratio of isocyanate groups to isocyanate-reactive groups of from 1.5: 1 to 4: 1.
20. Use of the coating composition of any of claims 1-19 to protect a surface of a substrate or a coating on a surface of a substrate.
21, coating method comprising the steps of applying the coating composition of any one of claims 1-19 to to a substrate surface, followed by curing and drying.
22, coated product comprising a substrate and a coating formed by applying the coating composition of any of claims 1-19 to the substrate and curing and drying.
23. The coated product of claim 22, wherein the coated product is a floor.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810809380.1A CN110734693A (en) | 2018-07-20 | 2018-07-20 | coating compositions |
| EP19739304.4A EP3824011B1 (en) | 2018-07-20 | 2019-07-17 | A coating composition |
| PCT/EP2019/069232 WO2020016292A1 (en) | 2018-07-20 | 2019-07-17 | A coating composition |
| ES19739304T ES2961667T3 (en) | 2018-07-20 | 2019-07-17 | A coating composition |
| US17/258,487 US20210277277A1 (en) | 2018-07-20 | 2019-07-17 | A coating composition |
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| CN201810809380.1A CN110734693A (en) | 2018-07-20 | 2018-07-20 | coating compositions |
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Cited By (3)
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| CN111635498A (en) * | 2020-05-11 | 2020-09-08 | 上海嘉宝莉涂料有限公司 | Modified polyurea and application thereof |
| CN113930142A (en) * | 2020-06-29 | 2022-01-14 | 科思创德国股份有限公司 | Two-component coating composition |
| WO2022148082A1 (en) * | 2021-01-06 | 2022-07-14 | 江苏凯伦建材股份有限公司 | Photo-curable two-component polyurea waterproofing coating and preparation method therefor |
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Application publication date: 20200131 |