JPS61179266A - Water reducible coating composition - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to aqueous dispersions of tertiary amine terminated polyethers and carboxylic acid functional polymers, processes for their preparation and coating compositions based on aqueous dispersions of the polymers. The coating compositions of the present invention are useful, among other things, for lining metal containers for food, beer, and other beverages.

Epoxy resins are generally recognized as offering an excellent combination of properties, providing good adhesion, flexibility and resistance to solvents and chemical attack.

There is an increasing demand worldwide for low V, O, C, water-reducing coating compositions to replace solvent-based systems (V, O, C are f/
weight of organic solvent per unit volume of solid coating, expressed in ft]. Epoxy resins are hydrophobic in nature.

Accordingly, many attempts have been made to modify epoxy resins to render them water-dispersible without losing their desirable properties. These solutions have met with varying degrees of success.

For example, European Patent Nos. 6334, 116225 and related patents describe the grafting of epoxy resins onto hydrophilic acrylic polymers containing carboxyl groups by reaction between the epoxy groups of the epoxy resin and the carboxylic acid groups of the acrylic polymer. It teaches how to become Therefore, the bond between the hydrophilic component and the hydrophobic component of the copolymer is an ester bond. This procedure has the disadvantage that in water-based coating compositions, the ester bonds have a tendency to hydrolyze, resulting in poor storage stability.

GB 1,585,486 and GB 1,585,487 teach a solution for growing hydrophilic acrylic polymers containing carboxyl groups by free-2 radical addition polymerization in the presence of modified epoxy resins. The key to this approach is the use of relatively high concentrations of free radical initiators (mainly benzoyl peroxide) with high hydrogen attraction; bring about to graft. This method has the disadvantage of a relatively small degree of grafting. Additionally, water-based coating compositions made in this manner have relatively high viscosities for a given solids.

Yet another means is disclosed in US Pat. No. 4,247,439, WO 8
No. 3,103,613 and related patents. These patents teach the reaction of residual epoxy groups of an epoxy resin with a tertiary amine in the presence of water to form a quaternary amine hydroxide terminated polyether.

The product of this reaction is dispersed in water by incorporating a mixture of carboxylic acid functional polymers. This process has the major drawback of requiring a relatively large number of intermediate products to build up the final product, and is therefore expensive.

According to the present invention, the tertiary amine-terminated polyether is the reaction product of the epoxy groups of the epoxy resin and the hydroxy groups of the hydroxy-functional tertiary amine, and the carboxylic acid-functional polymer makes this combination water-dispersible. An aqueous dispersion of a carboxylic acid functional polymer and a tertiary amine terminated polyether is provided in an amount sufficient to provide an aqueous dispersion of a carboxylic acid functional polymer and a tertiary amine terminated polyether.

The present invention also provides a method of making this aqueous dispersion, which method comprises: (a) reacting the epoxy groups of an epoxy resin with a hydroxy-functional tertiary amine to form a tertiary amine terminated polyether; (b) dispersing the tertiary amine terminated polyether in water with the aid of an amount of carboxylic acid functional polymer sufficient to render the combination dispersible.

The present invention further provides for the stability in water of (1) tertiary amine terminated polyethers in ion association with a ++in crosslinker and (ii) a polymer derived at least in part from carboxylic acid functional monomers. A coating composition comprising a dispersion is provided.

Actually (1) type and /-! It will also be appreciated that some associative polymers of type (ii) are present in the composition.

The ionically associated polymer complexes are believed to result from the acid-base relationship between the amine-terminated polyether and the carboxylic acid-containing polymer. Amine-terminated polyethers combine the 1,2-r-poquine groups of an epoxy resin with a hydroxy-functional tertiary amine (e.g., N,N-dimethylethanolamine).
is formed by reacting the hydroxy groups of

Optionally the coating may contain zinc oxide or other pigments depending on the end use.

An advantage of this product is that it allows considerable flexibility in formulating the coating composition with the desired solid viscosity relationship. A typical example is a 26 second Ford A4 at 25°C.
Cup viscosity is 45% solids and 21 seconds Ford A4
The viscosity of the solid in a cup is 17.5 inches.

In the simplest method for making the amine-terminated polyethers used in this invention, low molecular weight epoxy resins (
For example, DER 343) is reacted with bisphenol A in a suitable organic solvent.

A hydroxy-functional tertiary amine is added to the formed epoxy resin and the reaction mixture is maintained at about 100° C. for about 1 hour.

Examples of suitable hydroxy-functional tertiary amines include N,N-dimethylethanolamine (DMEA), N,
N-diethylethanolamine (DEEA), 2-dimethylamine-2-methyl-propertool (DMAMP)
) and triethanolamine.

During the course of the reaction, the tertiary amine group of the hydroxy-functional amine catalyzes the reaction between the remaining epoxy group of the epoxy resin and the hydroxy group according to the reaction formula below. In the case of DMEA in this formula, IRI and R2 are methyl groups and R3 is -0H20H2-. It must be kept in mind that the presence of hydroxy-functional solvents (eg butanol or butyl cellosolve) competes with the hydroxyl groups of the tertiary amine and reduces the yield of tertiary amine end groups. If significant amounts of water are present, undesirable quaternary amine hydroxides form. Favorable results are therefore achieved when the reaction is carried out under anhydrous conditions.

In order to confirm the above-mentioned reaction products and to facilitate the analysis, we have identified 1 and 2 available for the reaction.
- Maximized number of epoxide groups.

Experiment I Reaction of DMEA and Epoxy Groups 146.69 t of dry propylene oxide and 224.9 t of dry DMEA (water content 0.05
%) were mixed. The reaction mixture was heated to 40°C,
There it generated heat, reaching 90 degrees Celsius before the temperature started to drop. Excess reaction components were distilled off using a rotary evaporator. Analysis of the product by NMR and GPO showed that although there was some polymerization, the reaction products were mainly as shown below.

Experiment 2 Dry DKR311 119 in a 500-round bottom flask equipped with a condenser, thermometer, stirrer and temperature controller.
and dry DMEA2112, heated to 105°C,
It was held at that temperature for 1 hour. Excess DMEA was removed from the reaction mixture using a rotary evaporator. NMR analysis showed that the amount of residue in the product obtained was due to the reaction between the epoxy groups of DBR331 and the hydroxyl groups of DMFjA. Another evidence for tertiary amine end group products is
It was soluble in water only at low pH.

Experiment 3 DKR3312, 2r, DMEA 10.7 F, water 2
08 and 283 tons of dimethylformamide were mixed in a round bottom flask equipped with a reflux condenser, stirrer and thermometer and heated to reflux (106° C.). The mixture was kept under reflux for 6 hours. The product was purified using a rotary evaporator. Analysis of the product was consistent with it being a quaternary amine salt.

Furthermore, the product was soluble in water under neutral, acidic and basic conditions.

In the products of the invention, tertiary amine terminated polyethers are dispersed in sewage water with the aid of carboxylic acid functional polymers. At a given amount of product, the number of carboxylic acid groups in the carboxylic acid functional polymer is sufficient for stable dispersion in the water formed and for effective ionic association with the amine-terminated polyether. It requires something.

If the carboxylic acid-functional polymer is a copolymer of an ethylenically unsaturated acid, such as acrylic acid or methacrylic acid, and a hydrophilic comonomer, such as 2-hydroxyethyl acrylate, 2-hydroxyethyl acrylate or acrylamide, part of the product The number of acid groups on the carboxylic acid-functional polymer in a sufficient amount may be less than the number of tertiary amine groups on the polyether in the same amount of product. However, when the carboxylic acid-functional polymer is a copolymer of an ethylenically unsaturated acid and a highly hydrophobic monomer such as styrene or butyl acrylate, a larger proportion of acid groups is present than when a hydrophilic comonomer is used. Requires.

Our experiments with this type of system have revealed that, for a given amount of solids, the final viscosity of the coating composition is governed by:

(1) Spacing of carboxylic acid groups in a carboxylic acid functional polymer; when the total number of carboxyl groups is constant, the more the acid groups are spaced apart by other monomers, the lower the viscosity will be.

(ii) voa; The smaller the voa, the less the clay.

(in) Degree of neutralization of carboxylic acid groups; the lower the degree of neutralization, the lower the viscosity. However, it is always necessary to ensure a suitable neutralization history to provide a stable dispersion.

(1v) Ratio of carboxylic acid-functional polymer to tertiary amine-terminated polyether; the higher the ratio of carboxylic acid-functional polymer, the higher the viscosity.

(V) Molecular weight of carboxylic acid polymer: The higher the molecular weight, the higher the viscosity.

As mentioned above, the role of the solvent can be important in determining the properties of the final coating composition. When the degree of ionic association between polyether and polycarboxylic acid-functional polymer is too high, the polymer mixture gels and it is no longer possible to disperse it in water. The degree of ionic association is controlled by controlling the amine value of the polyether; in particular, by minimizing the number of molecules having tertiary amine groups at both ends. In the first case, this is 4-! Each end +c 1, 2
- This can be achieved by minimizing the number of modified epoxy resin molecules having epoxide groups; the second case can be achieved by reacting some of these groups with hydroxy-functional solvents, such as butyl cellosolve or butanol. Apparently, when the amine end-termination reaction is carried out in the presence of a hydroxy-functional solvent, the degree of amine end-termination is reduced because the tertiary amine is thought to bring about a reaction between the solvent hydroxyl groups and the epoxy groups of the epoxy resin. will.

Example 1 Weight (f) aa Acrylic acid 584ab
Styrene 843aC benzoyl peroxide 7. Obb Butyl Cellosolve 1414bC Ethyl Alcohol 1106cc t-Butyl Perbenzoate 5.4cd) Toluene
18,4dd t-butylbenzoate 5.4 de toluene 1841, aa
, ab, and ac were added to a flange-topped 52 round bottom flask equipped with a condenser, stirrer, and thermometer and stirred until the ac was dissolved.

2. Then bb and bc were added and the mixture was heated to reflux temperature (approximately 96° C.) and kept at this temperature for 1 hour.

3. Then cc and cd were premixed and added to the flask and kept under reflux for 30 minutes.

4, d, d and de were premixed and added to the flask and kept at reflux temperature for 1 hour.

Example 2 Weight (f) ab Bisphenol A 4
70ac Butyl Cellosolve 2
85.

bbDMEA 5
3bC butyl cellosolve 107a
aDMEA
70ee water
18881, aa, ab, and ac were added to a flange-top 52 round bottom flask equipped with a condenser, stirrer, and thermometer and mixed well.

The contents of the vessel were heated to 170° C. for 1 hour, then the heat was turned off and the reaction was exothermic to reflux temperature (195-200° C.).

The reaction was allowed to run until a viscosity of W at 25° C. (diluted to 52% solids in butyl cellosolve) was obtained (total treatment time was 1.5 hours), after which the vessel contents were evaporated for 45 minutes. The mixture was cooled to 130°C.

2. Then bb and be were premixed and slowly added to the flask with stirring. Cool the contents of the container to 100°C,
It was kept at that temperature for 1 hour. Approximately 15 Of of the solvent was removed by distillation under a stream of air to remove excess amine.

3. Next, add ca to the container and mix well. An additional stream of air was used to distill the 736f solvent.

4. Add act and mix well.

5. Added ee and mixed well.

5. ff was added and mixed well for 20 minutes.

The final coating composition was 45% solids, 166r/I! .

It had a VOC of 26 seconds at 25° C. and a viscosity of 4 cups at 25°C. A sample of this coating composition was dropped onto aluminum foil and cured for 10 minutes at 200°C. The coating showed excellent film properties.

Example 3 Weight (f) aa Acrylic acid 477a
b Acrylamide 115a
c water 3
280bb potassium persulfate
6bc water
1201, aa, ab and aC were added to a 5λ round bottom flask with a 7 lunge top equipped with a condenser, stirrer and thermometer and heated to reflux (10
0℃). Then the heating was turned off.

2, bb and bc were premixed and added to the flask for 2 hours, then heated and the vessel contents were kept under reflux for 1 hour.

Example 4 Weight (r) aa Epicoat 8920 5
19ab bisphenol A
470ac butyl cellosolve
285bb DMFiA
53bC butyl cellosolve
107CC Polyelectrolyte Solution (Example 3) 1
390adDMzA94 ee water
615ff Cymel 303
The method for producing 427 was the same as in Example 2, except that the solvent was not distilled off in step 3.

The coating composition formed had a Ford Cup Goose 4 viscosity of 78 seconds at 25°C when adjusted to 17 parts solids with water. Samples of this coating composition were dropped onto aluminum foil and cured for 10 minutes at 200°C. The coating showed excellent film properties.

Example 5 Polymer weight (f) aa Methoxypropoxypropanol 4
00ab deionized water 4.4
ac methyl ethyl ketone 45b
b Ethyl acrylate 680b
C Acrylic acid 65bd Hydroxypropyl methacrylate 210CC Benzoyl peroxide 4.5cd
Methyl ethyl ketone 45aa
t-Butyl perbenzoate 4
do butyl cellosolve 4cd
g water
5θat-butyl perbenzoate
4ef Butyl cellosolve 5
0eg water
5hhN,N-dimethylethanolamine
4011 water
1385jj Butyl cellosolve
2231, aa, ab, ac, and ad were added to a flange-topped 52-tube round bottom flask equipped with a condenser, stirrer, two addition funnels, and a thermometer-temperature controller and heated to 100° C. under a nitrogen atmosphere.

2. bb simultaneously for 2 hours while maintaining the temperature at 110°C.

Added bc and ba and CC and cd.

3. da, dθ, and df were added and kept at 100°C for 1 hour.

4, θθ, ef and eg were added and kept at 100°C for 1 hour.

5. Add hh and mix well.

6.11 was added and mixed well. 184Of solvent was distilled off at a temperature of 1009C to 120C.

7. Add jj and mix well.

Example 6 Weight 1f) aa DI! Ji 343 (Dow Chemical Company) 341ab Bisphenol A
293ac Butyl Cellosolve
1771)'b N,N-dimethylethanolamine 34bC butyl cellosolve 34cc Product of Example 5 707d(i Water
1600eθ Cymel 303 (Cyanamide Company) 120ff
water
2071, aa, ab, and ac were added to a flange-top 5A round bottom flask equipped with a condenser, stirrer, and thermometer and temperature controller and mixed well.

The contents of the container were heated to 170°C, the heating was stopped, and the exothermic reaction was brought to reflux temperature (195-200°C). The reaction was cooled to 170°C.

2. Cool to 130°C, add bll and be, 1
It was kept at 05°C for 1 hour. The solvent of 34f was distilled off.

3.cc was added and stirred well at 70°C for 30 minutes.

4. Add cud gradually while mixing well. Cooled to 50°C.

5. Added ee and mixed well.

5. ff was added to adjust the viscosity and mixed well.

7. gg was added and mixed until the precipitate was redispersed.

The coating composition formed had a solids content of 38% and a temperature of 50% at 25°C.
It had a viscosity of a Ford cup cup of 4 seconds.

Example 7 Weight (fl aa DF!R343681 ab Bisphenol A 58
6ac Butyl Cellosolve 35
5bb DMzA67 bC butyl cellosolve 671,
aa, ab and aC were mixed in a 2Il flask equipped with a condenser, thermometer-temperature controller and stirrer, heated to 170°C and heating was stopped. An exothermic reaction resulted in a temperature of 200°C.

When the temperature fell to 170°C, the reaction mixture was cooled to 130°C.

2. bb and bc were premixed and added to the reaction mixture. The temperature was maintained at 105° C. for 1 hour, after which 67 t of solvent was distilled off.

The following two examples illustrate methods for making carboxylic acid functional polymers in the presence of amine-terminated polyethers.

Example 8 Weight (f) ab Butanol 50
0ac pax wax 6364 LA
20bb Butyl acrylate
866be styrene
158ba acrylic acid
220be hydroxypropyl methacrylate 354aa benzoyl peroxide 8ce) luene aa t-butyl perbenzoate
2aS Butanol
20eθ t-butyl perbenzoate
6ef Butanol
2゜ff t-butyl perbenzoate efg Butanol
20gg dimethylethanolamine 136gh water
400hh
water 40
0211 Cymel 303
212jj water
46001, 52 with thermometer-temperature controller, condenser, stirrer and two dropping funnels
Aa, ab and ac were added to the flask and mixed.

The mixture was heated to 100°C.

2. bb , be , bd and be and also c
c and ce were premixed and added slowly into the flask over 2 hours at a controlled temperature of 100°C. Temperature: 100℃ for 1 hour
I kept it.

3. Premix da and da, add, reaction is 15
It was kept at 110°C for 10 minutes.

4, eθ and θf were premixed and added, and the reaction was kept at 120° C. for 1 hour.

5. Premix ff and fg, add, 6 hours 120
It was heat treated at 0.degree. C. and then cooled to 90.degree.

Distribution method 6. Add gg with constant stirring.

7. Add hh gradually while mixing well.

8. Added 11 while stirring.

9. Add jj while stirring.

The above coating composition was diluted to 17.5% solids and heated at 25°C.
It was found to have a viscosity of Ford Cup Black 4 of 16 seconds. The coating was sprayed onto two aluminum plates using a Nordsun Laboratory sprayer, both of which gave excellent coverage of about 1001+v and about 180 cm per plate.

Example 9 Weight (f) aa Amine-terminated polyether (Example 7)
659ab Methoxypropoxypropanol 400ac Pack Wax 6364
LA 20bb acrylic acid
]69bc styrene
242CC benzoyl peroxide 4adl-luene
40(ld t-butyl perbenzoate 2de methoxypropoxypropanol 20θe
t-butyl perbenzoate 2e
f methoxypropoxypropanol
2.1, aa in a 2 L flask equipped with a thermometer, temperature controller, condenser, stirrer and two dropping funnels.
, ab and aQ were mixed. The mixture was heated to 100°C.

2. Premix bb and bc and also cc and cd
were premixed. The two premixes were added separately over 1 hour and 15 minutes at 100°C. The temperature was then increased to 120°C and held at that temperature for 45 minutes.

3, aa and de were premixed and added. The reaction is 1
The temperature was kept at 150 for an exothermic reaction during 15 minutes.
It has become ℃.

4, eθ and ef were premixed and added to the flask.

The reaction was maintained at 120°C for 1 hour and 15 minutes. In order to remove residual monomers, the organic solvent of 1409 was distilled off.

The reaction product was dispersed in water in the same manner as in Example 8.

The coating composition formed had a viscosity of 40 seconds at 25° C. with a solids content of 29.4%.

The examples below demonstrate the use of hydroxy-functional tertiary amines other than DMI.

Example 10 Weight (r) aa DBR343213 ab Bisphenol A 182
ac butyl cellosolve 111b
b DEgA27.6 be Butyl cellosolve 27.
6aa water
7771, 2I with thermometer, temperature controller, condenser, and stirrer! , aa, ab and a in a flask
c was mixed and heated to 170°C, and heating was stopped at that temperature. The reaction was exothermic to a temperature of 195°C. Temperature 17
The temperature was lowered to 0°C and then to 130°C.

2. Premix bb and bC and add. The reaction is 1
It was kept at 105°C for an hour. Thereafter, the organic solvent of 51F was distilled off to remove residual DEEA.

3. Next, cc was added and mixed well at 70°C for 30 minutes.

4. While maintaining constant stirring (1d was then added gradually).

The coating composition formed exhibits excellent stability and is
It had a Ford Cup Black 4 viscosity of 31 seconds at 42% solids.

Example 11 Production of 2-dimethylamino-2-methylolprovaliether The production method was the same as in Example 10 except that 1 and component bb were DMAMP.

The coating composition formed has excellent stability, with 37%
The solid content had a viscosity of Ford Cup M4 of 23 seconds at 25°C.

Example 12 Dimethylisopropanolamine (DMPA) The manufacturing method was the same as Example 10 except that DMPA was used as the t-component bb.

The coating composition formed had excellent stability, with a solids content of 34 mm and a viscosity of 4 mm, 24 seconds at 25°C.

Example 13 Aqueous dispersion based on triethanolamine-terminated polyether The preparation method was the same as in Example 10, except that component bb was triethanolamine.

The coating composition formed has excellent stability and 34.8
% solids, had a Ford e-cup point 4 viscosity of 32 seconds at 25°C.

The following examples demonstrate that modified epoxy resins having a wide range of epoxy equivalent weights can be successfully amine-terminated and water dispersible according to the present invention.

Examples 14-19 Part 1: Modification of Epoxy Resins In each of these examples, 2 with a flange top equipped with a temperature probe, a stirrer and a condenser connected to a temperature controller.
Bisphenol A with a total amount of 803 f in 2 round bottom flasks.
The appropriate molar ratio of DFIR343 and DFIR343 (see Table 1) is 162f.
of butyl cellosolve. 170 for each ingredient for 1 hour
Mix continuously while heating to °C, then stop heating,
The exothermic reaction was carried out to reach a reflux temperature (195-200°C). The reaction was cooled to 100° C. and sampled for epoxy equivalent measurements.

Part 2: Amine-terminated After taking the sample, a mixture of DMEA and butyl cellosolve was added to the vessel and the temperature was maintained at 100° C. for 1 hour. The mixture used was as follows.

DMEiA(f) Butyl cellosolve(ri) Example 1
0 190 9B Example 11
190 49 Example 12 98
98 Examples 13 to 194949 Next, the reaction mixture was distilled for 1 hour under a nitrogen stream to remove excess DMEiA.

In each case 200 v of the product of the second part were thoroughly mixed with the carboxylic acid-functional polymer of 1782 at a temperature of 70° C. for 1 hour. Then in each case 450 water? was added to the reaction mixture and stirred to obtain a uniform dispersion.

Example 20 Weight (f) aa DKR3431500 ab Bisphenol A 12
89ac Butyl Cellosolve 7
82bbDM1nA
148bC butyl cellosolve 1
Mix aa, ab and ac in a flask equipped with 48 da water 6704 1, condenser, thermometer, temperature controller and stirrer. The mixture was heated to 170°C and heating was stopped. The reaction was annealed to a temperature of up to 190° C. (reflux temperature). The reaction was then maintained at reflux temperature for 5 hours. After this time, the modified epoxy resin was found to have an epoxy equivalent weight of 65,000. The mixture was then cooled to 130°C.

2, bb and be were premixed and added to the flask;
The reaction was maintained at 105° C. for 1 hour, after which 148 t of organic solvent was distilled off.

3. Next, add CC and mix well. The above resin mixture was gradually added under constant stirring to disperse it in the water. The viscosity of the paint was Ford Cup AIL 4 viscosity of 126 seconds at 25°C and 37% solids.

Example 21 Weight <1> aa Coating composition of Example 10 1026
ab titanium dioxide 214
bb Butanol 2
0°. water
201, aa and ab for 30 minutes in a high speed mill
was pulverized to obtain a pulverized product with a particle size of less than 6 μm.

2. bb was added to remove bubbles, and QQ was added to adjust the viscosity.

The pigmented coating composition has good stability and
It had a viscosity of 28 seconds of Ford Cup Magic 4 with a solid content of 50 grams.

Example 22 bb Carboxylic Acid Functional Polymer 9.2
0co DMFfA
O,8 Baa Water 154 1. The carboxylic acid functional polymer used was made as follows. Add 8402 acrylic acid, 767 t styrene, 11 f benzoyl peroxide, and 3055 f butyl cellosolve to a flange-top 5 L round bottom flask equipped with a condenser, stirrer, and thermometer, stir until ac is dissolved, heated to ℃. Heating was then stopped and the exothermic reaction was brought to reflux temperature, after which the temperature began to drop. When the temperature drops to 130℃,
Heating was started and the solvent of 273r was distilled off. The polyelectrolyte formed had an NVM of 35%.

When the sample was diluted with the same weight of butyl cellosolve, 25
It had a Gardner-Holch viscosity of W at °C.

2. Aa and bb were mixed well in a 750-degree flask at 70°C.

3.cc was added under constant stirring.

4. ad was added in 30 minutes.

The dispersion is stable, with 46% solids and 18% solids at 25°C.
It had a viscosity of Ford-Cup Falls 4 seconds.

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Claims (1)

[Scope of Claims] 1. An aqueous dispersion of a tertiary amine-terminated polyether and a carboxylic acid-functional polymer, wherein the tertiary amine-terminated polyether is an epoxy group of an epoxy resin and a hydroxy-functional tertiary amine. is a reaction product with the hydroxy group of
An aqueous dispersion characterized in that the carboxylic acid functional polymer is present in an amount sufficient to render the combination water dispersible. 2. The aqueous dispersion according to claim 1, wherein the amine-terminated polyether is formed from a bisphenol A epoxy resin. 3. The aqueous dispersion according to claim 2, wherein the molecular weight of the bisphenol A epoxy resin is increased by further reacting with bisphenol A. 4. The aqueous dispersion according to any one of claims 1 to 3, wherein the epoxy resin has an epoxy equivalent of more than 5,000. 5. The aqueous dispersion according to any one of claims 1 to 4, wherein the hydroxy-functional tertiary amine is a monohydroxy tertiary amine. 6. Claim 1, wherein the hydroxy-functional tertiary amine is N,N-dimethylethanolamine (DMEA)
The aqueous dispersion according to any one of items 5 to 5. 7. The aqueous dispersion according to claim 1, wherein the hydroxy-functional tertiary amine is triethanolamine. 8. Aqueous dispersion according to any one of claims 1 to 7, wherein the carboxylic acid-functional polymer is a polymer containing acrylic acid and/or methacrylic acid and/or crotonic acid. . 9. Any of claims 1 to 8, wherein the carboxylic acid functional polymer is a copolymer containing hydrophobic monomers such as styrene, butyl acrylate, ethyl acrylate, methyl methacrylate and butyl methacrylate. The aqueous dispersion according to one of the above. 10. The carboxylic acid functional polymer is a copolymer containing hydrophilic monomers such as hydroxyethyl acrylate and hydroxypropyl methacrylate. Aqueous dispersion. 11. Aqueous dispersion according to any one of claims 1 to 10, wherein the carboxylic acid-functional polymer contains acrylamide. 12. Aqueous dispersion according to any one of claims 1 to 11, in which the carboxylic acid-functional polymer is polymerized separately from the amine-terminated polyether and subsequently mixed with said polyether. . 13. Claims 1 to 1 in which a carboxylic acid functional polymer is polymerized in the presence of an amine-terminated polyether.
The aqueous dispersion according to any one of Item 2. 14. (a) reacting the epoxy groups of the epoxy resin with a hydroxy-functional tertiary amine to form a tertiary amine-terminated polyether; (b) dispersing the tertiary amine-terminated polyether in water; 1. A process for preparing an aqueous dispersion of a tertiary amine-terminated polyether and a carboxylic acid-functional polymer, characterized in that the dispersion is carried out with the aid of a sufficient amount of a carboxylic acid-functional polymer to provide a tertiary amine-terminated polyether and a carboxylic acid-functional polymer. 15. The method of claim 14, wherein the tertiary amine terminated polyether is formed under substantially anhydrous reaction conditions. 16. The method of claim 14, wherein the carboxylic acid functional polymer is dissolved in water prior to use to disperse the tertiary amine terminated polyether. 17. A coating composition comprising the aqueous dispersion according to any one of claims 1 to 13. 18, (i) a tertiary amine terminated polyether in ionic association with (ii) a polymer at least partially derived from a carboxylic acid functional monomer;
iii) Coating compositions consisting of stable dispersions of crosslinking agents in water. 19. A coating composition according to claim 18 formulated for use in lining metal containers for food and beverages.