GB1604545A - Coating compositions - Google Patents
Coating compositions Download PDFInfo
- Publication number
- GB1604545A GB1604545A GB23776/78A GB2377678A GB1604545A GB 1604545 A GB1604545 A GB 1604545A GB 23776/78 A GB23776/78 A GB 23776/78A GB 2377678 A GB2377678 A GB 2377678A GB 1604545 A GB1604545 A GB 1604545A
- Authority
- GB
- United Kingdom
- Prior art keywords
- coating composition
- aqueous coating
- composition according
- acid
- nitrogen
- 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.)
- Expired
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- 239000008199 coating composition Substances 0.000 title claims description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
- 239000003431 cross linking reagent Substances 0.000 claims description 18
- 239000012736 aqueous medium Substances 0.000 claims description 16
- 239000006185 dispersion Substances 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000004202 carbamide Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 229920003180 amino resin Polymers 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 150000002118 epoxides Chemical group 0.000 claims description 5
- 235000014655 lactic acid Nutrition 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 238000003860 storage Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical class OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 19
- 239000000758 substrate Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 10
- 238000000151 deposition Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- -1 glycol ethers Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000007746 phosphate conversion coating Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
- C09D5/443—Polyepoxides
- C09D5/4434—Polyepoxides characterised by the nature of the epoxy binder
- C09D5/4438—Binder based on epoxy/amine adducts, i.e. reaction products of polyepoxides with compounds containing amino groups only
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
Description
(54) COATING COMPOSITIONS
(71) We, IMPERIAL CHEMICAL INDUSTRIES LIMITED, Imperial Chemical
House, Millbank, London SW1P 3JF, a British Company do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
This invention relates to the preparation of aqueous coating compositions; in particular to such compositions which are useful for application to a conductive substrate by electrodeposition.
A conductive substrate may be coated with certain synthetic film-forming polymers by immersing the substrate in an aqueous dispersion of the polymer and making the substrate one electrode in an electrical current through which is passed a suitable electrical current.
The current is passed between the substrate and a counter-electrode, the counter-electrode being in electrical contact with the dispersion. Suitable polymers usually contain ionisable groups. Those polymers which are to be deposited at an anodic substrate usually contain anionic groups and those which are to be deposited at a cathodic substrate usually contain cationic groups. Other materials may be co-deposited at the substrate-electrode with the polymer, for example pigment and/or a crosslinking agent for the polymer.
Deposition of film-forming polymer at a cathodic substrate has certain advantages over deposition at an anodic substrate since, for example, there is no dissolution of metal from a cathodic metal substrate, such as a ferrous metal substrate. In the case of anodic deposition dissolution of metal can discolour the polymer coating. A further advantage of using a cathodic substrate is that a previously applied phosphate conversion coating is substantially unaffected by the passage of electric current.
Suitable synthetic film-forming polymers which may be applied by cathodic deposition are those polymers which contain basic nitrogen-containing groups. Suitable basic nitrogen-containing groups are amino or amine groups or residues of these groups. These polymers are preferably dispersed in an aqueous medium in the presence of an acid, for example phosphoric acid, which is capable of ionising at least some of the basic nitrogen-containing groups.
One suitable type of synthetic polymer containing basic nitrogen-containing groups which can be applied to a cathodic substrate is described in British Patent 1,461,823 and the disclosure of this patent is incorporated herein by this reference to it. The polymers described in this patent are essentially ionisable epoxy-amine abducts which are dispersible in aqueous medium in the presence of an acid, and which may be crosslinked with crosslinking agents such as phenol/formaldehyde or aminoplast resins.
One important requirement in a coating composition comprising an aqueous dispersion of synthetic film-forming polymer, and particularly one which is to be applied to a substrate by cathodic deposition under industrial conditions, is good stability to prolonged storage or usage and to variation in pH or temperaure. In general, the useful polymers having nitrogen-containing groups do not usually form true solutions in an aqueous medium but instead at least part of the polymer exists in the aqueous medium as discrete liquid, solid, colloidal or other forms of disperse particles which owe their stability in the coating bath to various factors, for example the number and/or the nature of the ionisable basic groups in the polymer and the degree of neutralisation of such groups by an acid.
Whilst the aqueous dispersions of synthetic polymers having basic nitrogen-containing groups, together with a desired crosslinking agent, may be of satisfactory stability for certain purposes, particularly when the pH is relatively low, good stability of the dispersions at a higher pH is often desired. In general the stability of most polymer dispersions is satisfactory at high acid concentrations but stability at higher pH values, for example a pH 5 - 7 is desirable since the coulombic yield of polymer deposited at a cathodic substrate is thereby increased due to the smaller amount of neutralising acid required.
We have now found that there is an improvement in the stability of aqueous coating compositions, particularly those suitable for cathodic deposition, which comprise a dispersion of an epoxy-amine adduct and certain crosslinking agents for the polymer, when the adduct and the crosslinking agent are mixed and heated together before they are dispersed in an aqueous medium in the presence of an acid.
According to this invention we provide an aqueous coating composition which comprises (a) a dispersion in an aqueous medium of a product obtained by mixing as the sole film forming components of a mixture and heating,
i) an epoxy-amine adduct having ionisable nitrogen-containing groups, and
ii) a crosslinking agent for the adduct, which agent is free from & arboxyl groups selected from phenoUformaldehyde and aminoplast resins or blends thereof to effect an increase in viscosity of the initial mixture of (i) and (ii); b) an acid which is capable of ionising the nitrogen-containing groups in the product defined in (a), there being present sufficient of the acid to neutralise at least 30% of the nitrogen-containing groups and form a dispersion of said product in the aqueous medium.
The increase in viscosity of the mixture is determined by comparing the viscosity of the mixture before and after heating, after dilution with a suitable solvent for example 2-butoxy ethanol to a solids content of 40%.
Preferably the increase in viscosity achieved by heating is at least 10% and preferably is in the range of 10 - 70%. The adduct and the crosslinking agent may be heated in the absence of a solvent but preferably one or both of them is or are dissolved or substantially dissolved in a solvent before mixing together, and further suitable solvent may be added to the mixture, for example to ensure homogeneity. Suitable solvents include alcohols, glycol ethers and esters, ketones, and aromatic hydrocarbons.
Preferably, in order to increase its viscosity by the desired amount, the mixture of adduct and crosslinking agent is heated at a temperature of at least 50"C and more preferably of 100"C or higher, for example in the range 100 - 150"C. Heating may be continued for any desired penod of time, for example over 1/2 to 5 hours.
The viscosity of the mixture before and after heating may be determined by conventional procedures which are used in the coating art.
The reaction product obtained by mixing and heating the adduct and crosslinking agent may be dispersed in an aqueous medium in the presence of the acid by suitable procedures.
Suitable acids to be used in the aqueous coating compositons of the invention include phosphoric, acetic, lactic acids, dimethylolpropionic, methane sulphonic and gluconic
acids.
Particularly suitable crosslinking agents include phenol/formaldehyde, urea/formaldehy
de and melamine formaldehyde resins. Urea/formaldehyde resins are particularly suitable especially when butylated.
Epoxy-amine adducts which are particularly suitable in this invention are those described in British Patent 1,461,823 which are selected from compounds of formula a B1 - A1 - C1 - A2 - B2 or (b) B1 - Al - C1 - A2 - C2 - A3 - B2, wherein A1 A2 and A3 are residues of essentially straight chain di-epoxides and are free of unreacted epoxide groups, B1 and B2 are residues of primary or secondary monoamines of
PKb value not greater than 4 and C1 and C2 are residues of diamines or primary
monoamines the adduct having a molecular weight of from 1,500 to 7,000.
The aqueous coating compositions of this invention may contain pigment and other
conventional paint additives. The compositions may be used in application processes other than cathodic electrodeposion, for example in spraying or brushing.
The invention is illustrated by the following Example in which parts and percentages are
by weight: (a) Preparation of an epoxy-amine adduct
The following ingredients
2-ethoxy ethanol 10.0 parts
n-butanol 3.3 parts
epoxy resin (having epoxide)
equivalent of 475 and
commercially available as
"Epikote" 1001 "Epikote" is a
Registered Trade Mark. 13.4 parts
epoxy resin (having epoxide
equivalent of 901 and
commercially available as
"Epikote" 1004) 13.4 parts were heated to 80 - 1000C with stirring until dissolved.
Diethylamine 1.6 parts was added to the above solution at 500C and after 2 hours at 55"C there were added:
Ethylene diamine 0.4 parts The temperature was maintained at 550C for 3 hours, raised to 15"C over 1 hour and heating under reflux was continued for 1 hour. 1.2 parts of volatile materials were removed by distillation.
(b) Preheating of epoxy-amine adduct and urea-formaldehyde resin
A mixture of
epoxy-amine adduct as obtained in
(a) above 55.7 parts and urea/formaldehyde (a 53% solution
in xylol/butanol of a butylated
urea/formaldehyde resin
(urea/formaldehyde = 1/2.25 molar) 18.9 parts were heated for 3 hours at 100 - 1200C during which time the viscosity of a sample (diluted to 40% solids by weight with 2-butoxy ethanol) increased from 8.0 stokes to 10.0 stokes.
(c) Preparation of unpigmented coating compositions
(i) According to the invention
The total product of (b) above (74.7 parts)
was cooled and emulsified by mixing with
Commercial lactic acid (free
lactic acid content of 71.7%
by titration) 4.1 parts
and water 77.5 parts
The translucent emulsion produced was stable for at least 3 months and its particle size was too small to resolve by optical microscopy.
(ii) Not according to the invention
Epoxy-amine adduct from (a) 55.7 parts
Urea/formaldehyde resin as
in (b) 18.9 parts were mixed without heating and emulsified in a solution of lactic acid in water in the manner described in (i). The emulsion produced had a milky appearance. It settled out on storage after several days and discrete particles were Just visible under an optical microscope X400.
WHAT WE CLAIM IS:
1. An aqueous coating composition which comprises
(a) a dispersion in an aqueous medium of a product obtained by mixing as the sole film-forming components of a mixture and heating,
(i) an epoxy-amine adduct having ionisable nitrogen-containing groups, and
(ii) a crosslinking agent for the adduct, which agent is free from carboxyl groups, selected from phenol/formaldehyde and aminoplast resins, or blends thereof to effect an increase in viscosity of the initial mixture of (i) and (ii); and
(b) an acid which is capable of ionising the nitrogen-containing groups in the product defined in (a), there being present sufficient of the acid to neutralise at least 30% of the nitrogen-containing groups and form a stable dispersion of said product in the aqueous medium.
2. An aqueous coating composition according to claim 1 wherein there is an increase in viscosity of the initial mixture of (i) and (ii) of at least 10% on a 40% by weight resin solids basis.
3. An aqueous coating composition according to claim 1 or claim 2 wherein the mixture of (i) and (ii) is heated to at least 500C.
4. An aqueous coating composition according to any one of claims 1-3 wherein the acid is selected from phosphoric, lactic, acetic, and dimethylol propionic acids.
5. An aqueous coating composition according to any one of Claims 1 - 4 wherein the crosslinking agent is a urea/formaldehyde, or melamine/formaldehyde resin.
6. An aqueous coating composition according to claim 5 wherein the crosslinking agent is a butylated urea/formaldehyde resin.
7. An aqueous coating composition according to any one of claims 1-6 wherein the epoxy-amine adduct is a compound of formulae (a) B1 - A1 - C1 - A2 - B2 or (b) B1 - A1 - C1 - A2 - C2 - A3 - B2, wherein A1 A2 and A3 are residues of essentially straight chain di-epoxides and are free from unreacted epoxide groups, B1 and B2 are residues of primary or secondary monoamines of p b value not greater than 4, and C1 and C2 are residues of diamines or primary monoamines, the adduct having a molecular weight of from 1,500 to 7,000.
8. An aqueous coating composition according to claim 1 substantially as herein defined and with reference to the Example.
9. A process of a preparing an aqueous coating composition which comprises
(a) mixing as the sole film forming components of a mixture and heating (i) an epoxy-amine adduct having ionisable nitrogen-containing groups, and
(ii) a crosslinking agent for the adduct which agent is free from carboxyl groups selected from phenol/formaldehyde and aminoplast resins or blends thereof, to effect an increase in viscosity of the initial mixture of (i) and (ii), including any solvent which is present, of at least 10%; and
(b) dispersing the product of (a) in an aqueous medium in the presence of an acid which is capable of ionising the nitrogen-containIng groups in the product of (a), there being sufficient of said acid to neutralise at least 30% of the nitrogen-containing groups and form a stable dispersion of said product in the aqueous medium.
10. A process of prepanng an aqueous coating composition according to claim 10 substantially as herein defined and with reference to the Example.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (10)
1. An aqueous coating composition which comprises
(a) a dispersion in an aqueous medium of a product obtained by mixing as the sole film-forming components of a mixture and heating,
(i) an epoxy-amine adduct having ionisable nitrogen-containing groups, and
(ii) a crosslinking agent for the adduct, which agent is free from carboxyl groups, selected from phenol/formaldehyde and aminoplast resins, or blends thereof to effect an increase in viscosity of the initial mixture of (i) and (ii); and
(b) an acid which is capable of ionising the nitrogen-containing groups in the product defined in (a), there being present sufficient of the acid to neutralise at least 30% of the nitrogen-containing groups and form a stable dispersion of said product in the aqueous medium.
2. An aqueous coating composition according to claim 1 wherein there is an increase in viscosity of the initial mixture of (i) and (ii) of at least 10% on a 40% by weight resin solids basis.
3. An aqueous coating composition according to claim 1 or claim 2 wherein the mixture of (i) and (ii) is heated to at least 500C.
4. An aqueous coating composition according to any one of claims 1-3 wherein the acid is selected from phosphoric, lactic, acetic, and dimethylol propionic acids.
5. An aqueous coating composition according to any one of Claims 1 - 4 wherein the crosslinking agent is a urea/formaldehyde, or melamine/formaldehyde resin.
6. An aqueous coating composition according to claim 5 wherein the crosslinking agent is a butylated urea/formaldehyde resin.
7. An aqueous coating composition according to any one of claims 1-6 wherein the epoxy-amine adduct is a compound of formulae (a) B1 - A1 - C1 - A2 - B2 or (b) B1 - A1 - C1 - A2 - C2 - A3 - B2, wherein A1 A2 and A3 are residues of essentially straight chain di-epoxides and are free from unreacted epoxide groups, B1 and B2 are residues of primary or secondary monoamines of p b value not greater than 4, and C1 and C2 are residues of diamines or primary monoamines, the adduct having a molecular weight of from 1,500 to 7,000.
8. An aqueous coating composition according to claim 1 substantially as herein defined and with reference to the Example.
9. A process of a preparing an aqueous coating composition which comprises
(a) mixing as the sole film forming components of a mixture and heating (i) an epoxy-amine adduct having ionisable nitrogen-containing groups, and
(ii) a crosslinking agent for the adduct which agent is free from carboxyl groups selected from phenol/formaldehyde and aminoplast resins or blends thereof, to effect an increase in viscosity of the initial mixture of (i) and (ii), including any solvent which is present, of at least 10%; and
(b) dispersing the product of (a) in an aqueous medium in the presence of an acid which is capable of ionising the nitrogen-containIng groups in the product of (a), there being sufficient of said acid to neutralise at least 30% of the nitrogen-containing groups and form a stable dispersion of said product in the aqueous medium.
10. A process of prepanng an aqueous coating composition according to claim 10 substantially as herein defined and with reference to the Example.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23776/78A GB1604545A (en) | 1978-05-30 | 1978-05-30 | Coating compositions |
| AU47338/79A AU4733879A (en) | 1978-05-30 | 1979-05-23 | Coating compositions |
| NZ190540A NZ190540A (en) | 1978-05-30 | 1979-05-24 | Aqueous coating composition based on a crosslinked epoxy-amine adduct |
| IT23045/79A IT1121516B (en) | 1978-05-30 | 1979-05-28 | COVERING COMPOSITIONS |
| PL21592479A PL215924A1 (en) | 1978-05-30 | 1979-05-28 | |
| FR7913570A FR2427368A1 (en) | 1978-05-30 | 1979-05-29 | AQUEOUS COMPOSITION BASED ON AN EPOXY-AMINE ADDITIONAL PRODUCT AND A CROSS-LINKING AGENT, ITS PRODUCTION PROCESS AND ITS APPLICATION TO THE COATING OF A CONDUCTIVE SUBSTRATE |
| ZA792636A ZA792636B (en) | 1978-05-30 | 1979-05-29 | Coating compositions |
| CA000328722A CA1148678A (en) | 1978-05-30 | 1979-05-30 | Epoxy-amine adduct water soluble acid, and phenoplast or aminoplast crosslinker aqueous coating composition |
| CS793727A CS209809B2 (en) | 1978-05-30 | 1979-05-30 | Method of preparation of the watery coating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23776/78A GB1604545A (en) | 1978-05-30 | 1978-05-30 | Coating compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1604545A true GB1604545A (en) | 1981-12-09 |
Family
ID=10201148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23776/78A Expired GB1604545A (en) | 1978-05-30 | 1978-05-30 | Coating compositions |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU4733879A (en) |
| CA (1) | CA1148678A (en) |
| CS (1) | CS209809B2 (en) |
| FR (1) | FR2427368A1 (en) |
| GB (1) | GB1604545A (en) |
| IT (1) | IT1121516B (en) |
| NZ (1) | NZ190540A (en) |
| PL (1) | PL215924A1 (en) |
| ZA (1) | ZA792636B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6670041B2 (en) | 2000-11-15 | 2003-12-30 | Solutia Austria Gmbh | Self-crosslinking water-dilutable binders |
| CN100436559C (en) * | 2006-11-21 | 2008-11-26 | 中国化工建设总公司常州涂料化工研究院 | Crosslinking agent in use for baking coating material of epoxy resin in monocomponent |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3538548A1 (en) * | 1985-10-30 | 1987-05-07 | Hoechst Ag | METHOD FOR PRODUCING SOLUBLE RESIN RESIN FREE FROM MONOMERIC AMINES WITH NH BONDS AND THE USE THEREOF |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1199497B (en) * | 1962-10-23 | 1965-08-26 | Albert Ag Chem Werke | Mixture with phenol-aldehyde condensation products as hardeners for epoxy resins |
| IT1012971B (en) * | 1973-06-04 | 1977-03-10 | Dullux Ltd | WATER COMPOSITIONS FOR COVERINGS |
-
1978
- 1978-05-30 GB GB23776/78A patent/GB1604545A/en not_active Expired
-
1979
- 1979-05-23 AU AU47338/79A patent/AU4733879A/en not_active Abandoned
- 1979-05-24 NZ NZ190540A patent/NZ190540A/en unknown
- 1979-05-28 IT IT23045/79A patent/IT1121516B/en active
- 1979-05-28 PL PL21592479A patent/PL215924A1/xx unknown
- 1979-05-29 FR FR7913570A patent/FR2427368A1/en not_active Withdrawn
- 1979-05-29 ZA ZA792636A patent/ZA792636B/en unknown
- 1979-05-30 CS CS793727A patent/CS209809B2/en unknown
- 1979-05-30 CA CA000328722A patent/CA1148678A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6670041B2 (en) | 2000-11-15 | 2003-12-30 | Solutia Austria Gmbh | Self-crosslinking water-dilutable binders |
| CN100436559C (en) * | 2006-11-21 | 2008-11-26 | 中国化工建设总公司常州涂料化工研究院 | Crosslinking agent in use for baking coating material of epoxy resin in monocomponent |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1121516B (en) | 1986-04-02 |
| CS209809B2 (en) | 1981-12-31 |
| FR2427368A1 (en) | 1979-12-28 |
| IT7923045A0 (en) | 1979-05-28 |
| ZA792636B (en) | 1980-11-26 |
| CA1148678A (en) | 1983-06-21 |
| NZ190540A (en) | 1981-07-13 |
| PL215924A1 (en) | 1980-02-25 |
| AU4733879A (en) | 1979-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |