GLYCIDYL ESTERS OF ALPHA, ALPHA BRANCHED ACIDS COMPOSITIONS

Abstract

The invention relates to compositions of ,-branched alkane carboxylic acids glycidyl esters with a defined isomeric composition where the sum of the concentration of the blocked and of the highly branched isomers is maximum 55% preferably below 40%, and most preferably below 30%.

The mixture of neononanoic acid glycidyl esters comprising at least 2,2-dimethyl heptanoic acid glycidyl ester and 2-methyl 2-ethyl hexanoic acid glycidyl ester and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters.

Claims

1. A composition of ,-branched alkane carboxylic glycidyl esters from butene oligomers, comprising a glycidyl ester mixture of neo-acid derived from a dimer (C9) or trimer (C13) of butene having both blocked isomers and highly branched isomers wherein a sum of a concentration of blocked isomers and the concentration of highly branched isomers of the glycidyl ester mixture is 55% weight or less based on the weight of the composition, wherein the glycidyl ester mixture comprises 2,2-dimethyl heptanoic acid glycidyl ester in 4 to 10 weight %, 2-methyl 2-ethyl hexanoic acid glycidyl ester in 40 to 70 weight % and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) in 10 to 25 weight % based on the weight of the composition.

2. A binder composition for paints or adhesives comprising the composition of claim 1 as a reactive diluent or as monomer.

3. A resin comprising the composition of claim 1 wherein the resin is selected from the group consisting of a polyester polyol resin, an acrylic polyol resin, a polyether polyol resin or an epoxy resin.

4. A composition of ,-branched alkane carboxylic glycidyl esters from butene oligomers, comprising a glycidyl ester mixture of neo-acid derived from a dimer (C9) or trimer (C13) of butene having both blocked isomers and highly branched isomers wherein a sum of a concentration of blocked isomers and the concentration of highly branched isomers of the glycidyl ester mixture is 55% weight or less based on the weight of the composition, wherein the glycidyl ester mixture comprises 2,2-dimethyl heptanoic acid glycidyl ester in 5 to 10 weight %, 2-methyl 2-ethyl hexanoic acid glycidyl ester in 45 to 65 weight % and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) in 12 to 22 weight % based on the weight of the composition.

5. A binder composition for paints or adhesives comprising the composition of claim 4 as a reactive diluent or as monomer.

6. A resin comprising the composition of claim 4 wherein the resin is selected from the group consisting of a polyester polyol resin, an acrylic polyol resin, a polyether polyol resin or an epoxy resin.

7. A composition of ,-branched alkane carboxylic glycidyl esters from butene oligomers, comprising a glycidyl ester mixture of neo-acid derived from a dimer (C9) or trimer (C13) of butene having both blocked isomers and highly branched isomers wherein a sum of a concentration of blocked isomers and the concentration of highly branched isomers of the glycidyl ester mixture is 55% weight or less based on the weight of the composition, wherein the glycidyl ester mixture comprises 2,2-dimethyl heptanoic acid glycidyl ester in 6 to 9 weight %, 2-methyl 2-ethyl hexanoic acid glycidyl ester in 47 to 61 weight % and 2-methyl 2-ethyl 3-methyl pentanoic acid glycidyl esters (sum of stereoisomers) in 14 to 21 weight % based on the weight of the composition.

8. A binder composition for paints or adhesives comprising the composition of claim 7 as a reactive diluent or as monomer.

9. A resin comprising the composition of claim 7 wherein the resin is selected from the group consisting of a polyester polyol resin, an acrylic polyol resin, a polyether polyol resin or an epoxy resin.

Description

EXAMPLES

Chemicals Used

[0064] Cardura E10: available from Momentive Specialty Chemicals [0065] Neononanoic glycidyl ester from Momentive Specialty Chemicals [0066] GE9S: neononanoic glycidyl ester of composition A (see table 2 below) [0067] GE9H: neononanoic glycidyl ester of composition B (see table 2 below) [0068] Neononanoic glycidyl ester of composition C (see table 2 below) [0069] Neononanoic glycidyl ester of composition D (see table 2 below) [0070] Neononanoic glycidyl ester of composition E (see table 2 below) GE5: glycidyl ester of pivalic acid obtained by reaction of the acid with epichlorhydrin. [0071] Ethylene glycol from Aldrich [0072] Monopentaerythritol: available from Sigma-Aldrich [0073] Methylhexahydrophtalic anhydride: available from Sigma-Aldrich [0074] Boron trifluoride diethyl etherate (BF3.OEt2) from Aldrich [0075] Acrylic acid: available from Sigma-Aldrich [0076] Hydroxyethyl methacrylate: available from Sigma-Aldrich [0077] Styrene: available from Sigma-Aldrich [0078] 2-Ethylhexyl acrylate: available from Sigma-Aldrich [0079] Methyl methacrylate: available from Sigma-Aldrich [0080] Butyl acrylate: available from Sigma-Aldrich [0081] Xylene [0082] Di-t-Amyl Peroxide is Luperox DTA from Arkema [0083] tert-Butyl peroxy-3,5,5-trimethylhexanoate: available from Akzo Nobel [0084] n-Butyl Acetate from Aldrich [0085] Dichloromethane from Biosolve [0086] Thinner: A: is a mixture of Xylene 50 wt %, Toluene 30 wt %, ShellsolA 10 wt %, 2-Ethoxyethylacetate l0 wt %. Thinner B: is butyl acetate [0087] Curing agents, HDI: 1,6-hexamethylene diisocyanate trimer, Desmodur N3390 BA from Bayer Material Science or Tolonate HDT LV2 from Perstorp [0088] Leveling agent: BYK 10 wt % which is BYK-331 diluted at 10% in butyl acetate [0089] Catalyst: DBTDL 1 wt % which is Dibutyl Tin Dilaurate diluted at 1 wt % in butyl acetate

TABLE-US-00002 TABLE 2 Composition of the neononanoic glycidyl ester (according to the described gas chromatography method for glycidyl esters of neo-acid) Glycidyl ester of acid V9XX (described in Table 1) A (%) B (%) C (%) D (%) E (%) V901 6.5 0.1 3.7 0.1 8.9 V902 0.6 2.55 0.6 2.4 0.7 V903 1.1 0.7 0.3 1.0 2.0 V904 0.8 1 0.1 2.2 1.8 V905 0.2 13.1 0.5 4.1 0.1 V906 0.4 11.6 0.4 9.6 0.4 V907 0.2 15.4 0.1 36.4 0.6 V908 0.1 0 0.1 0.0 0.1 V909 54.8 2.55 52.8 2.4 52.8 V910 K1 7.8 0 10.0 0.0 6.5 V910 K2 7.7 0.6 12.8 0.4 4.8 V911 2.4 1.2 0.7 2.0 4.2 V912 0.0 28.3 0.0 22.4 0.0 V913 6.8 0.1 6.4 0.1 6.5 V914 4.5 0 3.8 0.0 5.7 V915 0.6 22.3 0.6 16.8 0.4 V916 4.4 0.1 5.2 0.1 3.8 V917 1.1 0.4 2.1 0.1 0.5

Example 1

[0090] The following constituents were charged to a reaction vessel equipped with a stirrer, a condenser and a thermometer: 92.4 grams of GE9S, 24.0 grams of Butyl Acetate. That initial reactor charge has been heated up to 135 C. Then, the following mixture was added over a period of 1 h20 while keeping the temperature constant: 30.7 grams of acrylic acid, 1.2 grams of Di-t-Amyl Peroxide, 12.0 grams of n-Butyl Acetate. After further adding 1.2 grams of Di-t-Amyl Peroxide and 20.4 grams of n-Butyl Acetate, a post-cooking was pursued at 135 C. for 1 h. The acrylic polyol had a molecular weight (Mw) of 11400 Daltons and a Tg of about 10 C.

Example 2 Comparative

[0091] The following constituents were charged to a reaction vessel equipped with a stirrer, a condenser and a thermometer: 92.4 grams of GE9H, 24.0 grams of Butyl Acetate. That initial reactor charge has been heated up to 135 C. Then, the following mixture was added over a period of 1 h18 while keeping the temperature constant: 30.2 grams of acrylic acid, 1.2 grams of Di-t-Amyl Peroxide, 12.0 grams of n-Butyl Acetate. After further adding 1.2 grams of Di-t-Amyl Peroxide and 20.4 grams of n-Butyl Acetate, a post-cooking was pursued at 135 C. for 1 h. The acrylic polyol had a molecular weight (Mw) of 8600 Daltons and a Tg of about +26 C.

[0092] Observations: Tg of acrylic polyols is impacted by the composition of the neononanoic glycidyl ester (see examples 1, 2).

Example 3

The Adducts of Glycidyl Neononanoate, GE9S and Acrylic Acid or Methacrylic Acid

[0093] The adducts of Glycidyl neononanoate GE9S (see table 3) with acrylic acid (ACE-adduct) and with methacrylic acid (MACE-adduct) are acrylic monomers that can be used to formulate hydroxyl functional (meth)acrylic polymers.

TABLE-US-00003 TABLE 3 Compositions of the adducts intakes in parts by weight Meth acrylic Acrylic acid adduct acid adduct Initial reactor charge GE9S 250 250 Acrylic acid 80 Methacrylic acid 96.5 Radical Inhibitor 4-Methoxy phenol 0.463 0.463 Catalyst DABCO T9 (0.07 wt % on 0.175 0.175 Glycidyl ester) [0094] DABCO T9 and 4-Methoxy phenol (185 ppm calculated on glycidyl ester weight), are charged to the reactor. [0095] The reaction is performed under air flow (in order to recycle the radical inhibitor). [0096] The reactor charge is heated slowly under constant stirring to about 80 C., where an exothermic reaction starts, increasing the temperature to about 100 C. [0097] The temperature of 100 C. is maintained, until an Epoxy Group Content below 30 meq/kg is reached. The reaction mixture is cooled to room temperature.

Example 4

Acrylic Resins for High Solids Automotive Refinish Clearcoats

[0098] A glass reactor equipped with stirrer was flushed with nitrogen, and the initial reactor charge (see table 4) heated to 160 C. The monomer mixture including the initiator was then gradually added to the reactor via a pump over 4 hours at this temperature. Additional initiator was then fed into the reactor during another period of 1 hour at 160 C. Finally the polymer is cooled down to 135 C. and diluted to a solids content of about 68% with xylene.

TABLE-US-00004 TABLE 4 Acrylic resins recipe Weight % in Reactor 1 L (g) Initial Reactor Charge GE9S (or GE9H comparative) 28.2 169.1 Xylene 2.7 16.2 Feeding materials Acrylic acid 10 59.8 Hydroxy ethyl methacrylate 16.0 96.0 Styrene 30.0 180.0 Methyl methacrylate 15.8 95.0 Di t-Amyl peroxide 4.0 24.0 Xylene 8.3 49.8 Post cooking Di t-Amyl peroxide 1.0 6.0 Xylene 3.0 18.0 Solvent adding at 130 C. Xylene 50.8 305.0 Final solids content 61.8% Hydroxyl content 4.12%

Example 5

Clear Coats for Automotive Refinish

[0099] Solvents were blended to yield a thinner mixture of the following composition (table 5):

TABLE-US-00005 TABLE 5 Thinner composition Thinner Weight % in solvent blend, theory Toluene 30.1% ShellSolA 34.9% 2-ethoxyethyl acetate 10.0% n-Butyl acetate 25.0% Total 100%
A clearcoat was then formulated (table 6) with the following ingredients (parts by weight):

TABLE-US-00006 TABLE 6 Clearcoat formulation Resin of Desmodur BYK 10 wt % in DBTDL 1 wt % example ex 4 N3390 ButAc in ButAc Thinner 80.1 27.01 0.53 1.17 40.45

TABLE-US-00007 Clearcoat properties GE9H (comparative) GE9S Volatile organic content 480 g/l 481 g/l Initial viscosity 54 cP 54 cP Dust free time 12 minutes 14.5 minutes Koenig Hardness after 6 h 8.3 s 7.1 s

Example 6

Acrylic Resins for First Finish Automotive Topcoats

GE9S Based (28%) Acrylic Polymers for Medium Solids First-Finish Clear Coats

[0100] A reactor for acrylic polyols is flushed with nitrogen and the initial reactor charge (see table 7) heated to 140 C. At this temperature the monomer mixture including the initiator is added over 4 hours to the reactor via a pump. Additional initiator is fed into the reactor during one hour, and then the mixture is kept at 140 C. to complete the conversion in a post reaction. Finally the polymer is cooled down and diluted with butyl acetate to a solids content of about 60%.

TABLE-US-00008 TABLE 7 Acrylic resins recipe Intakes (parts by weight) Initial reactor charge GE9S 164.40 Xylene 147.84 Monomer mixture Acrylic acid 53.11 Butyl methacrylate 76.88 Butyl acrylate 48.82 Hydroxy-ethyl methacrylate 27.20 Styrene 177.41 Methyl methacrylate 47.31 Initiator Di-tert.-amyl peroxide (DTAP) 8.87 Post addition Di-tert.-amyl peroxide 5.91 Solvent (to dilute to 60% solids) Butyl acetate 246.00 Total 1000.0

Clear Lacquer Formulation

[0101] Clear lacquers are formulated (see table 8) from the acrylic polymers by addition of Cymel 1158 (curing agent from CYTEC), and solvent to dilute to spray viscosity. The acidity of the polymer is sufficient to catalyze the curing process, therefore no additional acid catalyst is added. The lacquer is stirred well to obtain a homogeneous composition.

TABLE-US-00009 TABLE 8 Clear lacquer formulations and properties of the polymers Intakes (part by weight) Ingredients Acrylic polymer 60.0 Cymel 1158 8.8 Butyl acetate (to application 24.1 viscosity) Properties Solids content [% m/m] 45.3 Density [g/ml] 0.97 VOC [g/l] 531

Application and Cure

[0102] The coatings are applied with a barcoater on Q-panels to achieve a dry film thickness of about 40 m. The systems are flashed-off at room temperature for 15 minutes, then baked at 140 C. for 30 minutes. Tests on the cured systems are carried out after 1 day at 23 C.

Example 7

[0103] In a reactor equipped with an anchor stirrer, a thermometer, condenser and monomer/initiator feeding system, 188.6 g of GE9S and 90 g of ethoxypropanol (EPR) were loaded and heated to about 150 C. (see table 9). A mixture of 52 g of hydroxyethylmethacrylate (HEMA), 160 g of styrene, 68 g of acrylic acid (AA), 10 g of dicumylperoxide (DCP), 37.7 g of GE9S and 40 g of ethoxypropanol (EPR) were added over 2 hours 30 minutes to the reactor while keeping its content at 150 C. After the feed, the reactor content was held for 30 minutes at this temperature. After the 30 minutes hold period, 108 g of HEMA, 30 g of AA, 142 g of isobutyl methacrylate (IBMA), 5 g of DCP and 45 grams of EPR were added over 2 hours and 30 minutes at about 150 C. followed by a rinsing step for the feed system with 5 g of EPR. After the rinsing step, the content of the reactor was held for 2 hours at 150 C. The reactor content was cooled down to 100 C. and 100 parts of EPR were distilled off at atmospheric pressure.

[0104] The polyacrylate polyol has a solids content of the solution of 90% by weight.

TABLE-US-00010 TABLE 9 Composition of polyol Materials Intake (g) Initial charge EPR 90 GE9S 188.6 Monomer Addition 1 AA 68 Styrene 160 GE9S 37.7 HEMA 52 EPR 40 DCP 10 Monomer Addition 2 AA 30 IBMA 142 HEMA 108 DCP 5 EPR 45 TOTAL 976.3

Example 8

[0105] The following constituents were charged to a reaction vessel: 0.7153 grams of a neononanoic glycidyl ester of composition C, 0.5958 grams of hexahydro-4-methylphthalic anhydride, 0.0014 grams of ethylene glycol. The reaction took place for 3 to 4 days at 140 C. The sample has been dried by evaporation. The polyester had a molecular weight (Mn) of 4700 Daltons and a Tg of +18.8 C.

Example 9 Comparative

[0106] The following constituents were charged to a reaction vessel: 0.5823 grams of a neononanoic glycidyl ester of composition D, 0.4775 grams of hexahydro-4-methylphthalic anhydride, 0.0011 grams of ethylene glycol, 0.2841 grams of n-Butyl Acetate. The reaction took place for 3 to 4 days at 120-140 C. and the solvent was then thoroughly removed by evaporation. The polyester had a molecular weight (Mn) of 5000 Daltons and a Tg of +43.7 C.

Example 10

[0107] The following constituents were charged to a reaction vessel: 0.7235 grams of a neononanoic glycidyl ester of composition E, 0.5981 grams of hexahydro-4-methylphthalic anhydride, 0.0014 grams of ethylene glycol. The reaction took place for 3 to 4 days at 140 C. The sample has been dried by evaporation. The polyester had a molecular weight (Mn) of 5700 Daltons and a Tg of +17.6 C.

[0108] Observations:

[0109] Tg of polyesters is impacted by the composition of the neononanoic glycidyl ester (see examples 8, 9, 10).

[0110] The resins of the examples can be formulated in coating compositions such as 2K (polyurethane) with a low VOC (volatile organic compound) level and still providing and excellent appearance.

Example 11

Monopentaerythritol/Methylhexahydrophtalic Anhydride/GE9S (1/3/3 Molar Ratio)=CE-GE9S

[0111] 80.4 g amount of butylacetate, 68.3 g of monopentaerythritol, 258.2 g of methylhexahydrophthalic anhydride are loaded in a glass reactor and heated to reflux until complete dissolution. Afterwards, the temperature is decreased down to 120 C. and 333.0 g of GE9S are added over about one hour. The cooking is pursued at 120 C. for the time needed to decrease epoxy group content and acid value down to an acid value below 15 mg KOH/g. Then, further 82.4 g of butylacetate are added. Test results are indicated in table 10.

Example 12 Comparative

Monopentaerythritol/Methylhexahydrophtalic Anhydride/GE9H (1/3/3 Molar Ratio)=CE-GE9Ha

[0112] 80.4 g amount of butylacetate, 68.3 g of monopentaerythritol, 258.2 g of methylhexahydrophthalic anhydride are loaded in a glass reactor and heated to reflux until complete dissolution. Afterwards, the temperature is decreased down to 120 C. and 337.1 g of GE9H are added over about one hour. The cooking is pursued at 120 C. for the time needed to decrease epoxy group content and acid value down to an acid value below 15 mg KOH/g. Then, further 83.4 g of butylacetate are added. Test results are indicated in table 10.

TABLE-US-00011 TABLE 10 Polyesters characterization Polyester SC Viscosity resin (%) Mw (Da) Mn (Da) Mw/Mn (PDI) (cP) CE-GE9S 78.6 974 919 1.06 2450 CE-GE9Ha 80.0 921 877 1.05 6220 SC: solids content

Formulation of the Clear Coats

[0113] The clearcoat has been formulated as follows: CE-GEx polyester with Tolonate HDT LV2 as hardener (0.03 wt % DBTDL)(see table 11).

TABLE-US-00012 TABLE 11 Clear coats, formulations DBTDL Binder 2 HDI BYK 10 wt % 1 wt % Thinner B CE-GEx (g) (g) (g) (g) (g) GE9S 80.0 36.56 0.72 3.15 89.75 GE9Ha 80.4 37.27 0.73 3.20 87.83

Characterization of the Clear Coats

[0114] The clearcoat formulations are barcoat applied on degreased Q-panel. The panels are dried at room temperature, optionally with a preliminary stoving at 60 C. for 30 min. Results are indicated in table 12.

TABLE-US-00013 TABLE 12 Clear coats, performances Drying DFT (min) Koenig Hardness (s) CE-GEx SC (%) conditions Cotton Balls 6 h 24 h 7 d GE9S 48.4 RT 223 3 17 159 GE9Ha 49.2 RT 91 3 36 212 GE9S 48.4 Stoving 30 Dust 4 44 174 min/60 C. free out of oven GE9Ha 49.2 Stoving 30 Dust 10 55 211 min/60 C. free out of oven

Example 13 Comparative

[0115] The following constituents were charged to a reaction vessel: 2.5500 grams of a neononanoic glycidyl ester of composition D, 1.1571 grams of dichloromethane, 0.0137 grams of boron trifluoride diethyl etherate. The reaction took place for 3 days at room temperature and the solvent was then thoroughly removed by evaporation. The polyether had a molecular weight (Mw) of 1900 Daltons and a Tg of 40.5 C.

Example 14

[0116] The following constituents were charged to a reaction vessel: 2.5438 grams of a neononanoic glycidyl ester of composition C, 1.0150 grams of dichloromethane, 0.0128 grams of boron trifluoride diethyl etherate. The reaction took place for 3 days at room temperature and the solvent was then thoroughly removed by evaporation. The polyether had a molecular weight (Mw) of 1500 Daltons and a Tg of 51.1 C.

[0117] Observations:

[0118] Tg of the modified polyether resin is impacted by the composition of the neononanoic glycidyl ester (see examples 13, 14).

Example 15

Polyether Resin

[0119] The following constituents were charged to a reaction vessel equipped with a stirrer, a thermometer and a condenser: 134 grams of di-Trimethylol propane (DTMP), 900 grams of glycidyl neononanoate, GE9S, 135.5 grams of n-butylacetate (BAC) and 2.5 grams of Tin 2 Octoate. The mixture was heated to its reflux temperature of about 180 C. for about 4 hours till the glycidyl neononaoate was converted to an epoxy group content of less than 0.12 mg/g. After cooling down the polyether had a solids content of about 88%.

Example 16 Comparative

Polyether Resin

[0120] The following constituents were charged to a reaction vessel equipped with a stirrer, a thermometer and a condenser: 28.8 grams of monopentaerythritol, 201.5 grams of Cardura E10P, 19.4 grams of n-butylacetate and 0.3552 grams of Tin (II) 2-ethylhexanoate. The mixture was heated to a temperature of about 180 C. for about 6 hours till the Cardura E10P was converted to an epoxy group content of about 25 mmol/kg. After cooling down the polyether had a solids content of about 94%.

Example 17

Polyether Resin

[0121] The following constituents were charged to a reaction vessel equipped with a stirrer, a thermometer and a condenser: 28.8 grams of monopentaerythritol, 187.1 grams of GE9S, 18.3 grams of n-butylacetate and 0.3550 grams of Tin (II) 2-ethylhexanoate. The mixture was heated to a temperature of about 180 C. for about 5.5 hours till the GE9S was converted to an epoxy group content of about 29 mmol/kg. After cooling down the polyether had a solids content of about 95%.

Example 18 Comparative

Polyether Resin

[0122] The following constituents were charged to a reaction vessel equipped with a stirrer, a thermometer and a condenser: 28.8 grams of monopentaerythritol, 189.4 grams of GE9H, 18.5 grams of n-butylacetate and 0.3572 grams of Tin (II) 2-ethylhexanoate. The mixture was heated to a temperature of about 180 C. for about 4 hours till the GE9H was converted to an epoxy group content of about 27 mmol/kg. After cooling down the polyether had a solids content of about 95%.

Formulation of the Clear Coats

[0123] A clear coat is formulated with one of the polyether (from examples 16, 17, or 18, the curing agent (HDI, Desmodur N3390), the thinner (Methyl Amyl Ketone), the levelling agent (BYK-331) and the catalyst (dibutyltin dilaurate, DBTDL) according to the amounts indicated in table 13.

TABLE-US-00014 TABLE 13 Clear coats, formulations BYK 10 DBTDL CEP- Binder Binder HDI wt % 1 wt % Thinner Example (ID) (g) (g) (g) (g) (g) CEP-16 From 40.1 30.7 0.47 1.03 15.1 Example 16 CEP-17 From 40.0 33.0 0.48 1.07 >12.5 Example 17 CEP-18 From 40.0 32.5 0.48 1.06 17.7 Example 18

Characterization of the Clear Coats

[0124] The clearcoat formulations (from table 13) are barcoat applied on degreased Q-panel, optionally on basecoated Q-panel. The panels are dried at room temperature after a preliminary stoving at 60 C. for 30 min. Clear coats have been characterized among others by measuring the Koenig hardness development (see table 14).

TABLE-US-00015 TABLE 14 Clear coats, drying (curing) properties CEP-16 CEP-17 CEP-18 1/Koenig Hardness (Degreased Q panels) (sec) 6 hours 8 10 11 24 hours 10 11 47 7 days 18 20 94 2/Koenig Hardness (Basecoated Q panels) (sec) 6 hours 7 8 7 24 hours 8 8 14 7 days 12 13 34

Example 19

Preparation for Vacuum Infusion of Composite Structures

[0125] A. resin for vacuum infusion of large structures such as yacht and wind turbines was prepared by mixing 27.7 part by weight of curing agent blend and 100 part of epoxy resins blend described here:

[0126] Epoxy resins blend: 850 part by weight Epikote 828 and 150 part of glycidyl neononanoate, GE9S.

[0127] Curing Agent blend: 650 part by weight of Jeffamine D230 and 350 part by weight of Isophorone diamine (IPDA).

[0128] Jeffamine D230 is a polyoxyalkyleneamines available from Huntsman Corporation. Epikote 828 is an epoxy resin available from Momentive Specialty Chemicals

Example 20

Example of Trowellable Floor and Patching Compound

[0129] The ingredients presented in the table 15 below were mixed for the preparation of a trowellable flooring compound

TABLE-US-00016 TABLE 15 Preparation of a trowellable flooring compound Weight (parts) Volume (parts) Supplier BASE COMPONENT EPIKOTE 63.2 126.3 Momentive 828LVEL 11.1 22.3 GE9S Byk A530 4.8 13.4 Byk Chemie Mix the additives into the EPIKOTE resin before filler addition Total 79.1 162.0 FILLERS Sand 1-2 mm 582.3 496.4 SCR Sibelco Sand 0.2-0.6 mm 298.4 254.4 SCR Sibelco Total 880.7 750.8 Disperse into the base component using a concrete mixer CURING AGENT COMPONENT EPIKURE F205 40.2 87.2 Momentive Total 40.2 87.2 Mix the curing agent well with the EPIKOTE resin base and Fillers before application Total formulation 1000.0 1000.0

Example 21

Formulation for a Water Based Self-Leveling Flooring

[0130] The ingredients presented in the table 16 below were mixed for the preparation of a waterbased self leveling flooring system.

TABLE-US-00017 TABLE 16 Preparation of a waterbased self leveling flooring system Weight (parts) Supplier Comment CURING AGENT COMPONENT (A) EPIKURE 8545-W-52 164.00 Momentive (HEW = 320 g/eq) EPIKURE 3253 4.00 Momentive Accelerator BYK 045 5.00 BYK CHEMIE defoamer Antiterra 250 4.00 BYK CHEMIE Dispersing Byketol WS 5.00 BYK CHEMIE Wetting agent Bentone EW (3% in water) 20.00 Elementis Anti-settling Mix the additive into the EPIKURE curing agents before filler addition Titanium dioxide 2056 50.00 KronosTitan Disperse the pigment for 10 minutes at 2000 rpm. EWO-Heavy Spar 195.00 Sachtleben Barium sulphate Chemie Quartz powder W8 98.00 Westdeutsche Quarzwerke Disperse fillers at 2000 rpm for 10 minutes Water 55.00 Sand 0.1-0.4 mm 400.00 Euroquarz Total component A 1000.00 RESIN COMPONENT (B) EPIKOTE 828LVEL 81.00 Momentive GE9S 19.00 Mix (B) into (A) Total formulation A + B 1081.00

TABLE-US-00018 Formulation characteristics Fillers + Pigment/Binder ratio 3.9 by weight PVC 37.7 % v/v Density 1.9 g/ml Water content 12.5 % m/m