JP5639208B2 - Use of dioxolane derivatives in coating systems and coating system formulations - Google Patents

Description

  The present invention relates to coatings and paints such as paints and varnishes (especially industrial, graphics and architectural paints), as film formers, as agent de coalescence and It relates to the use of dioxolane derivatives as drying inhibitors.

  Throughout the rest of this specification, architectural paints are understood as water-based paints (water-based paints), and industrial paints such as furniture, original automotive and repair paints are solvent-borne paints ( Solvent-based paints), but these are only for the sake of simplicity and do not imply any limitation on the scope of the invention.

  Architectural paints are evaluated for their quality and good appearance after application from the viewpoints of finish, coverage and durability. These properties are a result of the quality of paint components such as thickeners, pigments and surfactants. An important ingredient for obtaining good quality in architectural coatings is coalescing agents, which provide uniformity of contact between particles, giving the film a good appearance in terms of gloss and durability, wear resistance Give in the context of. Similarly, to ensure optimum application, industrial paints are solvent-based so that the drying time of the paint is adequate and prevents the presence of undesirable defects in the finished product. Must balance the composition.

  Several attempts have already been disclosed to improve paint quality, including:

  Japanese Patent Application Laid-Open No. Sho 62-241977 uses a solvent derived from glycerol as a solvent for pen ink, provides good viscosity, and makes it possible to obtain particularly fine and non-bleed characters, etc. Is described.

  In JP 62-156983 A, a solvent obtained by condensation of glycerol with aldehyde or acetone is applied to the surface of a printing material in order to give a good absorption of the paint and a clear blur-free image. It is described.

  JP 62-084171 describes the use of solvents obtained by condensation of glycerol with aldehydes or ketones in the production of graphics paints that dries more quickly and does not bleed.

  Japanese Unexamined Patent Publication No. 01-013080 relates to the use of polyoxyalkylene solvents as solvents and emulsifiers for paints.

  JP 06-073318 mentions the use of a glycerol / acetone mixture as solvent in the production of paint strippers / removers.

JP 62-241977 JP 62-156983 A JP 62-084171 A Japanese Patent Laid-Open No. 01-013080 Japanese Patent Laid-Open No. 06-073318

  The present invention uses dioxolane derivatives as film formers, in other words as coalescing agents, or as drying inhibitors in paint systems or paint formulations (particularly industrial, architectural or graphics paints), Different from art interieur.

  The term “film former” is commonly used and refers to any additive capable of changing, for example, the coalescence (cohesiveness) of the system and the speed of drying.

  One important advantage resides in the fact that the quality of the coating system can be maintained while using a lower amount of additive compared to the amount employed for other known additives of the prior art.

  In contrast to the prior art, the present invention is based not only on the use of one or more dioxolane derivatives as film formers, in other words as coalescing agents acting as film-forming aids in aqueous systems, but also on the basis of solvents. It is also used as a drying time retarder in systems, systems for coating substrates, especially in paints used in the field of graphics or construction industry.

  Film former is understood as an additive that, when present in a coating formulation, promotes the formation of a film when applied to a substrate.

  As is well known to those skilled in the art, the characteristic obtained when the drying time of the film is delayed is that it allows for good paint spreading and enhanced paint gloss.

  It will also be appreciated by those skilled in the art that coalescing agents can facilitate contact between particles, facilitate and improve film formation, and thereby improve the appearance and durability of the applied film (eg, paint or varnish). Is well known. These improvements are related to the glass transition temperature and minimum film formation temperature (MFFT), and are achieved as a result of the decrease in glass transition temperature and minimum film formation temperature, which are caused by coalescing agents.

  According to the present invention, a coalescing agent is understood as a substance used as a plasticizer that acts as an adjuvant in the formation of a film, and a retarding agent changes the drying time after applying a coating formulation to a substrate. To be understood

（ここで、Ｒ₁及びＲ₂は同一であっても異なっていてもよく、水素又は少なくともアルキル、アルケニル若しくはフェニル基を含む群から選択される基を表わし、
ｎは整数１、２、３、４又は５である。） The dioxolane derivatives used as film formers according to the present invention are of the following formula (I):

(Wherein R ₁ and R ₂ may be the same or different and each represents hydrogen or a group selected from the group comprising at least an alkyl, alkenyl or phenyl group;
n is an integer 1, 2, 3, 4 or 5. )

In particular R ₁ and R ₂ are groups selected from the group comprising methyl, ethyl, n-propyl, isopropyl or isobutyl groups.

  Preferably n is 1 or 2.

FIG. 1A is a graph representing the consumption of NCO functionality by the solvent hydroxyl functionality for system F1 / F2. FIG. 1B is a graph representing the consumption of NCO functionality by the hydroxyl functionality of the solvent for system F3 / F4. FIG. 1C is a graph representing the consumption of NCO functionality by the hydroxyl functionality of the solvent for system F5 / F6. FIG. 2A is a graph representing a comparison of the change in Brookfield viscosity of the test formulation for system F1 / F2. FIG. 2B is a graph representing a comparison of the change in Brookfield viscosity of the test formulation for system F3 / F4. FIG. 2C is a graph representing a comparison of the change in Brookfield viscosity of the test formulation for system F5 / F6. FIG. 3A is a graph representing a comparison of pH stability for pure acrylic resin systems SR1 and SR2. FIG. 3B is a graph representing a comparison of Brookfield viscosity stability for pure acrylic resin systems SR1 and SR2. FIG. 3C is a graph representing a comparison of the change in MFFT as a function of coalescent agent concentration for pure acrylic resin systems SR1 and SR2. FIG. 4A is a graph showing a comparison of pH stability for styrene-acrylic resin systems SR3 and SR4. FIG. 4B is a graph showing a comparison of Brookfield viscosity stability for styrene-acrylic resin systems SR3 and SR4. FIG. 4C is a graph showing a comparison of the change in MFFT as a function of coalescent agent concentration for styrene-acrylic resin systems SR3 and SR4. FIG. 5A is a graph representing a comparison of pH stability for vinyl-acrylic resin systems SR5 and SR6. FIG. 5B is a graph showing a comparison of Brookfield viscosity stability for vinyl-acrylic resin systems SR5 and SR6. FIG. 5C is a graph showing a comparison of the change in MFFT as a function of coalescent agent concentration for vinyl-acrylic resin systems SR5 and SR6. FIG. 6A is a graph representing a comparison of pH stability for pure acrylic paint systems F1 and F2. FIG. 6B is a graph representing a comparison of Krebs viscosity stability for pure acrylic paint systems F1 and F2. FIG. 6C is a graph showing a comparison of wear resistance (number of cycles) for pure acrylic paint systems F1 and F2. FIG. 6D is a graph representing a comparison of the change in gloss at 60 ° for pure acrylic paint systems F1 and F2. FIG. 7A is a graph showing a comparison of pH stability for styrene-acrylic paint systems F3 and F4. FIG. 7B is a graph representing a comparison of Krebs viscosity stability (KU) for styrene-acrylic paint systems F3 and F4. FIG. 7C is a graph showing a comparison of abrasion resistance (number of cycles) for styrene-acrylic paint systems F3 and F4. FIG. 7D is a graph representing a comparison of gloss change at 60 ° for styrene-acrylic paint systems F3 and F4. FIG. 8A is a graph representing a comparison of pH stability for vinyl-acrylic paint systems F5 and F6. FIG. 8B is a graph representing a comparison of Krebs viscosity stability for vinyl-acrylic paint systems F5 and F6. FIG. 8C is a graph showing a comparison of wear resistance (number of cycles) for vinyl-acrylic paint systems F5 and F6. FIG. 8D is a graph showing a comparison of the change in gloss at 60 ° for vinyl-acrylic paint systems F5 and F6.

  In one preferred embodiment of the present invention, the dioxolane derivative of formula (I) of the present invention is 2,2-dimethyl-1,3-dioxolane-4-methanol, also known by the name of Solketal. It has been. This derivative is particularly advantageous as a coalescing agent for formulating aqueous coatings (water-based coatings).

  In another preferred embodiment of the present invention, the dioxolane derivative of formula (I) of the present invention is 2,2-diisobutyl-1,3-dioxolane-4-methanol, which is also known as 1-isobutylisopropylideneglycerol. It is also known by the acronym IIPG. This derivative is particularly advantageous as a dry time retarder for formulations of solvent-borne coatings (solvent-based coatings).

  The present invention also provides a coating system formulation (coating system formulation) comprising at least one dioxolane derivative as a film former. These formulations can in particular be based on water or non-aqueous solvents.

  In accordance with the present invention, the amount of the dioxolane derivative of the present invention that is added to the paint formulation to obtain the desired enhancement effect is significantly less than that employed for other known additives. For example, the amounts employed for the compounds of the present invention are the prior art additives such as ethyl glycol acetate (EGA), butyl glycol acetate (BGA) and propylene glycol monomethyl ether acetate (PMA) for comparable performance. Can be 10% of the amount employed. In addition, formulations using the dioxolane derivatives of the present invention have been shown to be even more economical, resulting in a better cost / benefit tradeoff.

  Solvent-based coating systems suitable for the present invention whose properties are improved by the addition of dioxolane derivatives according to the present invention include, for example, systems based on nitrocellulose, polyester, cellulose acetate butyrate (CAB) and polyurethanes, epoxies, acrylics , Melamine or phenolic.

  Water-based architectural coatings suitable for the present invention include vinyl, vinyl-acrylic, pure acrylic and styrene-acrylic systems.

  The amount of one or more dioxolane derivatives used in the coating formulation ranges from about 0.1 to about 10% by weight, more specifically from about 0.1 to about 5% by weight, based on the total weight of the paint. Is advantageously in the range of In architectural systems, the amount of dioxolane derivative added is in the range of 0.1-5% of the paint formulation.

  Other advantages and details of the invention will become more apparent upon reading the exemplary embodiments of the invention given below. However, these specific examples are not intended to be more restrictive than those included in the appended claims.

Industrial paint

  Eight formulations were prepared according to Table I below. This system is a polyurethane varnish that contains 65% of a mixture of isocyanate and polyol and 35% of a solvent group and is generally used as a coating for metal and wood substrates. In the table, EGA represents ethyl glycol acetate, BGA represents butyl glycol acetate, and PMA represents propylene glycol monomethyl ether acetate. Solketal is the dioxolane derivative Solketal used.

  AB9 represents an alkylbenzene compound containing an alkyl substituent having 9 carbon atoms and is sold under the name IR9 by Shell. Toluene and xylene compounds are hydrocarbons sold by the company Petrobras.

  The following points were tested:

a. Measuring the percentage of free NCO over time:
This test is well known to those skilled in the art and determines whether the NCO functionality has reacted with the OH functionality of the solvent. This measurement is performed by a back titration technique, which is by adding a certain amount of amine to the paint. This amine reacts with the NCO functional group to give the urea functional group; the unconverted amine is analyzed by neutralization with acid (hydrochloric acid). NCO% is equal to the amount of amine added minus the analytical amount of excess amine.

b. Drying time of film on metal substrate:
This test evaluates the drying properties of the system and the results are expressed as a function of time. These results are as follows:
• Dust-free drying: The time when dust no longer remains on the surface.
-Finger touch drying: The time when the surface no longer shows tackiness when touched.
Handling Drying: The time during which a surface with higher pressure than touched no longer shows deformation.

c. Gloss:
This test defines the degree to which the surface finish approaches an ideal theoretical specular gloss that can be considered as a perfect specular based on an arbitrary value of 100 (valeur arbitraire).

d. Mechanical strength and chemical resistance:
This measurement defines the degree of resistance (expressed in number of cycles) to the compression action of the finished surface, using polishing in the mechanical strength test and the solvent methyl ethyl ketone (MEK) in the chemical resistance test. Is used.

e. Cross-cut (cross cut) or score (striated) adhesiveness:
These tests are performed to check the adhesion between the film layers, and are performed using a traveling device provided with a plurality of parallel cutting blades fixed to the handle. After the surface is completely dried, a series of cuts are made at 90 ° crossing angles to form a grid. Next, an adhesive tape is affixed to the cut area, and this is quickly removed. Check if the tape removes the grid from the surface or coating.

f. Hardness of the formed film:
This measurement is performed using a series of graphics pencils grouped according to hardness increasing from 8B (softest) to 10H (hardest). A line is drawn with this series of pencils on the formed film and it is checked which pencil of hardness has caused the line to scratch.

g. Flexibility by bending (bending) on a conical mandrel:
This test is carried out using a device called a conical mandrel that includes a lever over the entire length of the conical cylinder. First, a test piece is attached to one end of the device and then deflected. This test evaluates the behavior of the coating in terms of flexibility.

h. Brookfield viscosity of the formulation:
This test is performed using a Brookfield LV DV II viscometer. Viscosity is an important parameter for both product utilization and storage.

  The results of these tests and measurements are shown in the following table and attached drawings.

1A-1C represent the consumption of NCO functionality by the solvent hydroxyl functionality for the following:
・ System F1 / F2 (Fig. 1A)
System F3 / F4 (FIG. 1B) and System F5 / F6 (FIG. 1C).

2A-2C represent a comparison of the change in Brookfield viscosity of the test formulation for the following.
・ System F1 / F2 (Fig. 2A)
System F3 / F4 (FIG. 2B) and System F5 / F6 (FIG. 2C).

  A comparison of the drying times for the various systems tested is shown in Tables 2A, 2B, and 2C below.

  Tables 3A, 3B and 3C summarize the results obtained for the gloss measurements of each system tested.

  Tables 4A, 4B, and 4C relate to the mechanical strength and chemical resistance results of films obtained using the tested formulations.

  Tables 5A, 5B and 5C relate to the score tack results of the tested formulations.

  Tables 6A, 6B and 6C list the hardness results of the films obtained for the tested formulations.

  Tables 7A, 7B, and 7C show the flexural flexibility results for the tested formulations.

  The above results indicate that the formulation according to the present invention containing a small amount of film-forming additive (solketal) is the main solvent in the prior art formulations (especially when the prior art solvents are EGA, PMA and BGA) ), It shows that it exhibits equivalent performance and characteristics for various test aspects.

Architectural paint

  This example shows the combination agent Texanol (2,2,4-trimethyl-1,3-pentanediol monobutyrate, CAS No. 25265-77-4, sold by Eastman Chemical Company) well known in the prior art and the present The aim is to compare the use of IIPG (CAS No. 5694-81-5) according to the invention in architectural coatings.

  Illustrate the following items:

(A) Three resin systems (pure acrylic base, styrene-acrylic base or vinyl-acrylic base) commonly sold in the paint market and their respective polymerization processes. These polymerization processes and the equipment used for this purpose are routine and well known to those skilled in the art. A preferred combination device consists essentially of a polymerization reactor equipped with a heating / cooling system and respective control systems, a condenser, a reservoir of various starting materials and respective metering devices, a pump and an inerting system.

(B) The paint base containing the coalescing agent is an existing product, and three kinds of paint bases containing the above-mentioned system are prepared in two series. In the first series, each resin system is mixed with 2 wt% Texanol coalescence, and in the second series, each of the three resin systems is mixed with 2 wt% IIPG coalescence.

(C) A comparative test is performed on the paint base mixed with these six coalescing agents for testing the stability of pH, viscosity stability, MFFT as a function of coalescent agent concentration.

(D) A series of three architectural paint formulations selected from the above bases and added with 2% by weight Texanol as a prior art product, and 2% by weight as a product formulated according to the teachings of the present invention. Comparison with another series of three architectural paint formulations with the addition of IIPG.

(E) A comparative test is carried out on the six formulations described above for pH stability, viscosity stability, abrasion resistance and gloss change.

Perform the following polymerization:
1. Charge the reaction components of the charge into the reactor.
2. After the condenser is started, the reactor is stirred under inactivation.
3. Heat to a suitable temperature (eg 80 ° C.).
4). A monomer is added simultaneously with water and a surfactant to obtain a pre-emulsion (pre-mix).
5. Catalyst 1 is added slowly.
7). Add catalyst 2 slowly.
8). Finally, the pH is adjusted to the range of 8.7 to 9.2.

  In the figure, SR1 and SR2 respectively represent those obtained by adding 2 wt% Texanol or 2 wt% IIPG to a resin system referred to herein as pure acrylic according to Table II above.

Polymerization process Charge the reaction components of the charge into the reactor.
2. After the condenser is started, the reactor is stirred under inactivation.
3. Heat to a suitable temperature (eg 80 ° C.).
4). A monomer is added simultaneously with water and a surfactant to obtain a pre-emulsion (pre-mix).
5. Slowly add the catalyst solution.
6). Finally, the pH is adjusted to a range of 8.5-9.

  In the figure, SR3 and SR4 respectively represent styrene-acrylic resin systems according to Table III described above containing 2% by weight of Texanol or 2% by weight of IIPG.

Polymerization process Charge the reaction components of the charge into the reactor.
2. After the condenser is started, the reactor is stirred under inactivation.
3. Heat to a suitable temperature (eg 80 ° C.).
4). Add monomer.
5. Slowly add the catalyst solution.
6). Add the redox solution.

  In the figure, SR5 and SR6 are obtained by adding 2% by weight of Texanol or 2% by weight of IIPG to the vinyl-acrylic resin system according to Table IV above.

  In the figure, F1 and F2, respectively, are 2% by weight of Texanol or 2% by weight of a paint formulation containing the pure acrylic resin system of Table II and the semi-gloss paint formulation base of Table V in a weight ratio of 45/55. The one containing 2% by weight of IIPG is shown.

  Similarly, F3 and F4 are each 2% by weight of Texanol in a paint formulation containing the styrene-acrylic resin system of Table III and the semi-gloss paint formulation base of Table V in a weight ratio of 45/55. Or the thing containing 2 weight% IIPG is shown.

(1) ABEX EP110 Anionic surfactant Sold by Rhodia Poliamida e Especialidades in Brazil.
(2) SIPOMER COPS 1 Stabilizer Sold by Rhodia Poliamida e Especialidades in Brazil.
(3) IGEPAL CO-630 Nonionic surfactant Sold by Rhodia Poliamida e Especialidades in Brazil.
(4) TRIGONOX AW 70 catalyst Sold by Akzo Nobel.
(5) LUREDOX RC 99% catalyst Sold by BASF.
(6) Rhodoline 211 Polymer electrolyte dispersant Sold by Rhodia North America in the United States.
(7) Rhodoline 681F Antifoam Agent Sold by Rhodia North America in the United States.
(8) PROXEL GLX Biocide Sold by Avecia Group Plc.
(9) Acrysol RM-5000 Rheological additive Sold by Rohm and Haas.
(10) Acrysol (TM) TT 935 Rheological additive Sold by Rohm and Haas.

  In the figure, F5 and F6 are each 2% by weight of Texanol in a paint formulation containing the vinyl-acrylic resin system of Table IV above and the matte paint formulation base of Table VI in a weight ratio of 18/82. Or the thing containing 2 weight% IIPG is shown.

  A description of the analytical methods used to test the above resin systems and paints is given below.

Evaluation method of wear resistance

1. After cleaning a 20 × 50 cm glass plate with alcohol, attach a Leneta P 121-10N test panel (sold by The Leneta Company, USA);
2. Clean the test panel with alcohol;
3. Place a spreader (a 175 μm thick film) in the center of the Leneta panel at the top of the test panel;
4). Place a reference sample from the left to the center of the spreader;
5. Place the sample for evaluation on the right hand side of the test panel.
6). Pull the spreader by hand at a speed of 3-5 seconds until reaching the bottom of the test panel. Repeat this process three times for each sample;
7). Leave the applied sample in a controlled environment (temperature 22 ± 2 ° C., relative humidity 55 ± 5%) for 7 days to dry;
8). After this period, on the glass plate of the GAT device (Gardner abrasion tester, manufactured according to ASTM standard D-2486), the test glass for evaluation is placed on the inner side of the table with the sand glass part facing up. Fixing;
9. 10 g of abrasive paste (prepared according to NBR standard 14940) is weighed onto a brush and this brush is mounted in the apparatus. Add 10 ml of demineralized water to the whole test panel, set the cycle number counter to 0 and connect the device, then start the start operation;
10. Each front and back stroke of the brush constitutes one cycle, and the paint on which the brush is applied is completely removed from one area to the other, and the black background of the Leneta panel is completely exposed with a continuous line. The paint is worn out when
11. The device automatically stops at 400 cycles each. At this point, remove the brush without washing. A further 10 g of abrasive paste and 10 milliliters of demineralized water are applied onto the brush path.

  This process is performed until the end of the test. The cycle count is stopped when the connection between the wear line of the paint being analyzed is first confirmed.

Evaluation method of MFFT (minimum film formation temperature)

  Equipment used: Rhopoint MFFT bar 60, in 6 temperature steps ranging from -5 ° C to + 60 ° C. Evaluation is performed according to ASTM standard D-2354 65T.

1. Lift the glass cover covering the heating platform of the device;
2. Smear a uniform layer of propylene glycol with a brush on the heating table;
3. Cut a piece of aluminum foil and place it on a heating table with a layer of propylene glycol to ensure a uniform and uniform appearance and adhere firmly to the table;
4). Clean the surface of the aluminum foil with a piece of paper soaked in ethanol, and then dry the surface;
5. Adjust the temperature to an appropriate width by lowering the cover, connecting the device and opening the temperature control water supply valve;
6). After the temperature has stabilized, nitrogen is blown at a rate of 4 liters / minute at a pressure of 4 bar to remove moisture from the surface of the table;
7). Lift the cover and apply at least three parallel layers of the sample being analyzed using a spreader on a 75 μm film for a width of 1.5 cm; close the cover and allow the dispersion to dry completely under nitrogen Wait for
8). Use a spatula to examine the transition from the point where the film becomes brittle to the point where the film is flexible and continuous after drying;
9. Move the guide ruler of the device to this point and read the corresponding temperature (° C) on the scale of the device.
10. Repeat this operation for the remaining coating layers and take the arithmetic average.

Stability evaluation method

1. Homogenize the sample with a spatula;
2. Add sample for evaluation to fill about 90% of 250 ml flask;
3. Place a plastic film in the mouth of the flask and close it with a cover to prevent vapors from leaking;
4). Keep the flask in an oven at 60 ° C. for 1 month;
Every 5.7 days, remove the flask from the oven and wait for it to stabilize at ambient temperature and examine the following property changes:
・ Color and smell;
Phase separation, surface liquid formation and / or sedimentation;
• If there is no phase separation, measure viscosity and pH.

pH measurement method

1. Using a known calibrated pH measuring device, the pH measuring electrode is directly inserted into the sample.
2. Wait 1 minute for the device to stabilize.
3. Read the pH.

Brookfield viscosity measurement method

Apparatus: Brookfield viscometer

1. Approximately 400 milliliters of sample is placed in a constant temperature bath at 25 ° C. for 2 hours. After this time, homogenize the sample with a glass rod and check with a thermometer that the sample is at 25 ° C;
2. Transfer the sample to a 600 ml glass beaker up to the 400 ml mark.
3. A suitable spindle for reading the viscosity is selected so that the reading shown on the instrument dial is in the range of 20% to 80%.
4). Attach the spindle to the apparatus, place it in the center of the flask and adjust the dip height to the mark of the rod;
5. Read for 1 minute. Viscosity values are expressed in centipoise (cP).

Method for measuring Krebs viscosity

Equipment used: Stormer viscometer

1. The sample is placed in a constant temperature bath at 25 ° C. for 2 hours.
2. When this time has elapsed, homogenize the sample using a glass rod and check whether it is at 25 ° C.
3. Place the sample in the viscometer and insert the spindle to be measured by lowering the lever of the instrument to the existing mark on the spindle.
4). When the lever is lowered, the instrument starts the measurement and continues with the measurement for one minute as measured by the stopwatch.

Gloss measurement method

Equipment used: Gardner Micro-TRI-Glossy system. Method according to ASTM standard D 523 and ASTM standard D2457.

1. After cleaning a 20 × 50 cm glass plate with alcohol, attach a Leneta P 121-10N test panel (sold by The Leneta Company, USA);
2. Clean the test panel with alcohol;
3. Place a spreader (with a film thickness of 175 μm) in the center of the Leneta panel at the top of the test panel;
4). Put paint from left to right of spreader;
5. Pull the spreader by hand to the bottom of the test panel at a speed of 3-5 seconds;
6). Leave the applied sample in a controlled environment (temperature 22 ± 2 ° C., relative humidity 55 ± 5%) for 7 days to dry;
7). Connect gloss device, set to 60 ° angle, adjust to take 20 readings;
8). Take measurements at various points on the film so that the final average is reliable;
9. The average of the measurement is the gloss value.

Figure:

  The figure contains the following information:

3A: Pure acrylic resin: pH stability FIG. 3B: Pure acrylic resin: Brookfield viscosity stability FIG. 3C: Pure acrylic resin: MFFT change as a function of coalescent agent concentration FIG. 4A: Styrene-acrylic resin: pH Figure 4B: Styrene-acrylic resin: Brookfield viscosity stability Figure 4C: Styrene-acrylic resin: change in MFFT as a function of coalescent agent concentration Figure 5A: Vinyl-acrylic resin: pH stability Figure 5B: Vinyl-acrylic resin: Stability of Brookfield viscosity Figure 5C: Vinyl-acrylic resin: MFFT change as a function of coalescent agent concentration Figure 6A: Pure acrylic paint: pH stability Figure 6B: Pure acrylic paint: Krebs viscosity Stability Figure 6C: Pure acrylic paint: Abrasion resistance (number of cycles)
6D: Pure acrylic paint: Gloss change at 60 ° FIG. 7A: Styrene-acrylic paint: pH stability FIG. 7B: Styrene-acrylic paint: Krebs viscosity stability (KU)
FIG. 7C: Styrene-acrylic paint: Abrasion resistance (number of cycles)
Fig. 7D: Styrene-acrylic paint: Gloss change at 60 ° Fig. 8A: Vinyl-acrylic paint: pH stability Fig. 8B: Vinyl-acrylic paint: Krebs viscosity stability Fig. 8C: Vinyl-acrylic paint: abrasion resistance (Number of cycles)
FIG. 8D: Vinyl-acrylic paint: change in gloss at 60 °

Conclusion:

  In comparison of prior art coalesces with coalesces according to the subject matter of the present invention, even in resin systems in which coalesces are mixed, in paint formulations containing these resin systems and additional amounts of these coalesces. It has also been observed that the dioxolane derivatives according to the invention exhibit comparable properties and are perfectly compatible for use as coalescing agents in architectural coatings.

  From the information and examples provided herein, those skilled in the art will make modifications to the invention that are not expressly set forth herein or described in the claims, and are similar regardless of other forms. Can be achieved to achieve the same result, which is also encompassed within the scope of protection as set forth in the appended claims.

Claims (11)

The following formula (I):

(Wherein R ₁ and R ₂ may be the same or different and each represents a hydrogen atom or a group selected from the group comprising alkyl and alkenyl groups;
n is an integer 1, 2, 3, 4 or 5)
Dry time retarder for solvent-borne coating formulations, characterized in that it comprises at least one dioxolane derivative according to claim 1.   The solvent-based paint formulation is a nitrocellulose, polyester or cellulose acetate butyrate (CAB), or a formulation based on polyurethane, epoxy, acrylic, melamine or phenolic. Drying time retarder for solvent based paint formulations. Methyl R ₁ and R ₂ are ethyl, n- propyl, and wherein the isopropyl or isobutyl group, the drying time retarders for solvent-borne coating formulation according to claim 1 or 2.   The drying time retarder for solvent-borne paint formulations according to any one of claims 1 to 3, wherein n is 1 or 2.   5. A drying time retarder for solvent-borne paint formulations according to any of claims 1 to 4, characterized in that the dioxolane derivative is 2,2-dimethyl-1,3-dioxolane-4-methanol.   The drying time retarder for solvent-borne paint formulations according to any one of claims 1 to 4, characterized in that the dioxolane derivative is 2,2-diisobutyl-1,3-dioxolane-4-methanol. Solvent-based paint based on nitrocellulose, polyester or cellulose acetate butyrate (CAB), or based on polyurethane, epoxy, acrylic, melamine or phenol and containing at least one dioxolane derivative as a drying time retarder A compound comprising:
The dioxolane derivative has the following formula (I):

(Wherein R ₁ and R ₂ may be the same or different and each represents a hydrogen atom or a group selected from the group comprising alkyl and alkenyl groups;
n is an integer 1, 2, 3, 4 or 5)
According to claim 1, characterized in that R ₁ and R ₂ are methyl, ethyl, n- propyl, and wherein the isopropyl or isobutyl group, formulation according to claim 7. 9. Formulation according to claim 7 or 8 , characterized in that n is 1 or 2. 10. Formulation according to any one of claims 7 to 9 , characterized in that the dioxolane derivative is 2,2-dimethyl-1,3-dioxolane-4-methanol. 10. Formulation according to any one of claims 7 to 9 , characterized in that the dioxolane derivative is 2,2-diisobutyl-1,3-dioxolane-4-methanol.

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