Document pp2R7MVp5ZYVX19BL2v3xGO4D

ti /iftiJLc BENTHAL** . APPLICATION IN ALKYD RESINS Monsanto Chemicals-Plastics X/4 Monsanto Technical Bulletin No. O-D-503 March 15, 1950 Development Dept. Organic Chemicals Division Monsanto Chemical Co., St. Louis 4, Mo. INTRODUCTION Short oil modified alkyd resins, when prepared under certain conditions with dibasic acids or anhydrides and polyhydric alcohols, react rapid ly and give products with high acid values. The replacement of a portion of the dibasic acid by BENTHAL in such alkyd resins will retard the bodylng and permit longer processing time In order to reduce the acid value of the product. The BENTHAL polyhydric alcohol product becomes part of the resin molecule and acts ,as an internal plasticizer, thus improving flexibility and adhesion of the dried film. *Reg.U.S.Pat.Off. The information contained in this bulletin is, to our best knowledge, true and accurate, but all recommenJatlont ut suggestions are made without guarantee, since the conditions of use err beyond our control, The Monsanto Chemical Company disclaims any liability incurred in connection with the use of these date or suggestions. Fivthermore. nothing contained herein shall be^ construed as recommendation to use sny product In conflict with existing patents covering any material or its uss. , OZO1*607 TOWOLDMONOQ25036 BENTHAL Specifications Appearance Ash Odor Melting Point Light yellow powder 0.20$ Max. Strong characteristic ll8C. Min. to start Properties Given to Alkyd Resins by BENTHAL BENTHAL reacts with ethylene glycol, glycerol and pentaerythrltol to form a liquid resin with low acid value. It is effective In alkyd resins when added in recommended quantities with phthalic anhydride during processing. 1. Reduces the acid value. 2. Reduces the viscosity. 3. Slightly improves the original color. 4. Retards yellowing on baking at elevated temperature. 5- Retards after-bodying. 6. Improves flow properties. 7. Does not retard air drying or baking. 8. Does not change water or chemical resistance of dried films. 9. Improves stability. 10. Improves film adhesion of pentaerythritol types. 11. Improves flexibility of dried films. Reactions of BENTHAL in Alkyd Resins Three parts by weight of BENTHAL react with one part of glycerol if heated and agitated 3 hours at 450F. in the presence of an inert gas. The final product has an acid value of 2-3. a viscosity K-M (Gardner-Holdt viscosimeter) and a color 4-5 (Gardner color standards). It is non-drying and has plasticizing properties. The replacement of 3-l# of phthalic anhydride by BENTHAL in short oil (40$) modified alkyd resins lengthens the processing time, lowers the acid value, and retards the bodying action. The BENTHAL was added with the phthalic anhydride. Properties, such as air drying, baking, and resistance to water, alkali, and weather, are not appreciably changed in alkyd resins of the linseed, soy, or castor oil type. The color is slightly paler. In all the experiments following, a 600 ft./min. peripheral speed turbine was used as agitator. Carbon dioxide was bubbled through the alkyd resins mixture and was started at the beginning of heat ing and continued until the batch was ready for thinning. The carbon dioxide was introduced into the bottom of the batch directly beneath the turbine through a perforated ring near the bottom of the kettle. -2- 020*608 TOWOLDMONOQ25037 Other Modifications Other polyhydric alcohols such as sorbitol and mannitol can be used In alkyd resins containing 3-10$ BENTHAL based on the phthalic anhydride replacement with satisfactory results for lengthening the processing time, reducing the acid value, and retarding the bodying. Experimental Data on Processing Alkyd Resins with BENTHAL (1) Castor Oil Alkyd Resin -- Short Oil Modified Reagents: Raw castor oil (40$ oil modified) 2.6 moles glycerine . 3-0 moles phthalic anhydride BENTHAL replacement for 5 and 10$ phthalic anhydride . Process: All Ingredients were added to the kettle and heated slowly to 480F. and held for body. Evaluation: TABLE I Alkyd Resin Processing Time at 480F. Acid Value Viscosity 50$ Xylol Color 50$ Xylol Sward Hardness Alkyd 70$ Solids Melamine 30$ Solids 1/2 Hr. 300F. Control 60 min. 22.0 Z-2 5 5$ BENTHAL 107 min. 9-4 Z-2 4-5 10$ BENTHAL 210 min. 7-2 Z-2 4-5 16-18 16-18 16-18 (2) Linseed Oil Alkyd Resin -- Short Oil Modified Reagents: Varnish type linseed oil (40$ oil modified) 2.4 moles glycerine 3 moles phthalic anhydride BENTHAL replacement for 3 and 5$ phthalic anhydride Process: The linseed oil and glycerine (25$ by welght0of the former) were subjected to alcoholysis at 450 p. in the presence of a litharge catalyst (0.10$ Pb of the weight of glycerine). The balance of glycerine was added, followed by the phthalic anhydride and BENTHAL and the total batch processed to 450P. and held for body. -3- 0204609 TOWOLDMONOQ25038 Evaluation: TABLE II Alkyd Resins Processing Color Time at 450f. Acid Viscosity 50$ Minutes Value 50$ Xylol Xylol Control 3$ BENTHAL 5$ BENTHAL 60 75 90 15 F 12 F 8F 6-7 6-7 6 Sward Hardness Bake at 300 F 1 Hr. 12 12 11 (3) Soy Fatty Acid-Alkyd Resin -- Short Oil Modified Reagents: Double distilled soy fatty acids (40$ oil modified) 2.4 moles glycerine (98$) 3 moles phthalic anhydride BENTHAL replacement for 2 and 4$ phthalic anhydride Extra glycerine in amount of 10$ of soy fatty acids Process: All ingredients were added to the kettle and heated slowly to 450F. and held for body. Evaluation: TABLE III Alkyd Resins Processing Color Sward Hardness Time at 450F. Acid Viscosity 50$ Bake 300F. Minutes Value 50$ Xylol Xylol 1 Hr. Control 2$ BENTHAL 4$ BENTHAL 90 100 120 12 F 10 F 8F 5-6 11 5-6 11 5 10 (4) Cocoanut Fatty Acids Alkyd Resin -- Short Oil Modified Reagents: Distilled cocoanut fatty acids (34$ modification) 2.4 moles glycerine 3.0 moles phthalic anhydride Pentaerythritol replacement for 10$ of glycerine extra glycerine in amount of 10$ of cocoanut fatty acids BENTHAL replacement for 3 and 5$ phthalic anhydride Process: All ingredients were added to the kettle and processed slowly to 450F- and held for body. 0ZCH610 TOWOLDMONOQ25039 Evaluation: Alkyd Resins Processing Time at 450f. Minutes Control 3$ BENTHAL 5$ BENTHAL 75 90 120 TABLE IV Color Acid Viscosity 60$ Value 60$ Xylol Xylol Sward Hardness Alkyd Resins 70$ Sol:' Melamine 30$ Solid ____ l/2 Hr. 300F. 18 u-W 5-6 15 U 12 U 5 5 S (5) Soy-Tung-Pentaerythrltol-Malelc Anhydride-Alkyd ~Resln -- Long Oil Modified Reagents: 50$ Alkali refined soy oil 8$ Pentaerythrltol . 20$ W. W. Rosin or 12$ W. W. Rosin and 8$ BENTHAL 17$ Tung oil 5$ Maleic anhydride Process: The soy oil and pentaerythrltol were subjected to alcoholysis in the presence of a litharge catalyst (0.10$ Pb per weight of pentaerythritol), by heating for 20 min. to 480F. for sol ubility of 1:1 in methyl alcohol. The tem perature was reduced to 400F. and the rosin, BENTHAL and finally tung oil were added. The batch was heated until clear when cold. Final ly the maleic anhydride was added and the batch was heated to 500F. and the process completed at 5706F. Evaluation: TABLE V Alkyd Resin Processing at 500-570 F. Acid ___ Minutes Value Viscosity 50$ Mineral Spirits Air Drying Time Co-drier Rosin type 75 BENTHAL type 120, 18 E-F 4 hours-dust free 10 E 4 hours-dust free (6) Soy Fatty Acld-Glyoerlne-Malelc Anhydride-BENTHALAltcyd Resin-Short Oil Modified Reagents: 39-4$ Distilled soy fatty acids 15-8$ Glycerine 15-4$ Maleic anhydride 29-4$ BENTHAL 0204611 -5- TOWOLDMONOQ25040 Process and Evaluation: . All ingredients were heated at 450F. for one hour and forty minutes. The batch was thinned with 50$ xylene. The product had an acid value of 8.4 (solids), viscosity S, color 5, and the film baked hard in 1/4 hour at 300&F. and air dried (Pb and Co drier) in 2 hours to dust free stage. (7) Soy Fatty Acld-Pentaerythrltol-Glycerine, ~BENTHAL-Al'kyd Resin-Short' 611 Modified ' Reagents: 41$ Distilled soy fatty acids 4$ Glycerine (9$) 21$ Technical pentaerythritol 32$ Phthalic anhydride 2$ BENTHAL Process and Evaluation: ` All ingredients were heated to 430F. and held for 3-1/2 hours. The batch was thinned with 50$ xylene. The product had an acid value of 10 (solids), color 7, viscosity W. The films baked hard in 1/2 hour at 30DF. (8) Soy 011-Pentaerythrltol-BENTHAL-Phthallc AnhydrldeAlkyd"Resln-Short Oil Modified Reagents: 270 g. Alkali refined soy oil 133 Technical pentaerythritol 180 g. Phthalic anhydride 120 g. BENTHAL ', Process and Evaluation: Alkali refined oil and 27 g. technical penta erythritol were processed at 48oF. using calcium catalyst for 30 minutes until clear (soluble in methyl alcohol l-l). Then 106 g. technical pentaerythritol were added and the batch temperature was held at 480F. until clear. The temperature was then dropped to 400F. and phthalic anhydride and BENTHAL were added and processed at 450F. for six hours. The batch was thinned with 50$ xylene. The product had an acid value of 12 (solids), vis cosity W, color 8. The film baked hard in l/2 hour at 300F. (Sward 12). 0204612 TOWOLDMON0025041 (9) Soy Oll-Pentaerythrltol-BENTHAL-Succlnic Acld-Alkyd Resin-Long Oil Modified' ' Reagents: 240 g. Alkali refined soy oil 69 g. Technical pentaerythritol 63 g. Succinic acid 60 g. BENTHAL Process and Evaluations ' Alkali refined soy oil and 24 g. technical pentaerythritol were processed at 480F. using calcium catalyst, for 30 minutes until clear and then 45 g. technical penta erythritol were added and held until clear. Succinic acid and BENTHAL were added at 400F. and processed at 450F. for 4 hours. The batch was thinned with 50# mineral spirts. The product had an acid value of 5.8 (solids), viscosity D, and color 6. The film air dried (Pb and Co drier) in 3 hours to a dust free stage. For further Information about BENTHAL contact the nearest Monsanto office. MONSANTO CHEMICAL COMPANY St. Louis Akron Birmingham Boston Charlotte Chicago Cincinnati Cleveland Detroit Houston Los Angeles New York Philadelphia Portland (Ore.) San Francisco Monsanto Chemicals Ltd London Seattle Monsanto Chemicals (Australia) Ltd. Melbourne Monsanto (Canada) Ltd. Montreal Toronto Vancouver Representatives in the Principal Cities of the World PEM:WA-549-.5M; 649-.5M -350- M Printed In U.S.A. -7- 0204613 TOWOLDMONOQ25042