Document J3VZgyvwRDBXX6BJgZV52mZd6
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Monsanto
Chemicals ** Plastics _______ u________
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BENTHAL*
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APPLICATION IN ALKYD RESINS
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Monsanto Technical Bulletin No. 0-D-503 .....March 15, 1950
Development Dept. Organic Chemicals Division Monsanto Chemical Co., St. Louis 4, Mo.
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INTRODUCTION
Short oil modified alkyd resins, vhen 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 body
ing 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.
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Reg.U.S.Pat.Off.
The information contained In this bulletin i, to Our beet knowledge, true end accurate, but all recommendation* or suggestion* are made without guarantee, since the conditions of use are beyond our control* The Monsanto Chemical Company disclaims any liability incurred in connection with the use of these data or suggestions. Fwthermore, nothing contained herein shall be! construed as a recommendation to use any product in conflict with
existing patents covering any material or Its use. .
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DSW 305354
STLCOPCB4069508
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 penta* erythritol 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.
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2. Reduces the viscosity.
3* Slightly improves the original color.
4. Retards yellowing on taking at elevated temperature.
5* Retards after-bodying.
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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 3-1$ of phthalic anhydride by BENTHAL in short oil (40$) modified alkyd resins lengthens the processing time, lowers the acid value, and retards the bodying action. The BENTHAL was added with the phthalic anhydride. Properties, such as air drying, baking, and resistance to water, alkali, and weather, are not appreciably changed in alkyd resins of the linseed, soy, or castor oil type. The color is slightly paler. In all the experiments following, a 600 ft./min. peripheral speed turbine was used as agitator. Carbon dioxide was bubbled through the alkyd resins mixture and was started at the beginning Of heat ing and continued until the batch was ready for thinning. The carbon dioxide was introduced into the bottom of the batch directly beneath the turbine through a perforated ring near the bottom of the kettle.
DSW 305355 2
STLCOPCB4069509
Other Modifications ..................................................................................
Other polyhydric alcohols such as sorbitol and mannitol can
be used in aikyd resins containing 3-i$ BENTHAL based on the
phthalic anhydride replacement with satisfactory results for
lengthening the processing time, reducing the acid value, and
retarding the bodying.
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Experimental Data on Processing Aikyd Resins with BENTHAL
(l) Castor Oil Aikyd 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
Aikyd Resin
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Processing Time at 480F.
y> Acid Value
...... -
Viscosity 50$ Xylol
Color 50$
Xylol
Sward Hardness Aikyd 70$ Solids Melamine 30$ Solids l/2 Hr. 300 F.
Control 5$ BENTHAL
10$ BENTHAL
60 min. 107 min. 210 min.
22.0 9.4 7.2
Z-2 Z-2 Z-2
5 4-5 4-5
16-18 16-18 16-18
(2) Linseed Oil Aikyd Resin -- Short Oil Modified
Reagents:
Varnish type linseed oil (40$ oil modified)
2.4 moles glycerine
;
3 moles phthalic anhydride
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BENTHAL replacement for 3 and 5$ phthalic anhydride
Process: -
The linseed oil and glycerine (25$ by weightQof the former) were subjected to alcoholysis at 450 F. in the presence of a litharge catalyst (0.10$ Fb of the weight of glycerine). The balance of glycerine was added, followed by the phthalic anhydride and BENTHAL and the total batch processed to 450F. and
held for body.
DSW 305356 STLCOPCB4069510
Evaluation:
...TABLE II
Alkyd Resins
Processing
Time at 450F. ..... Minutes
Acid Value
Viscosity 50$ Xylol
Color ' Sward Hardness
50$ Bake at 300P"
Xylol
1 Hr.
Control
60
15 F 6-7 : 12
3$ BENTHAL
75
. 12
F
6-7
12
5$ BENTHAL
90
,8
F,
6.
11
(3) Soy Fatty Acid-Alkyd Resin -- Short Oil Modified
Reagents:
. . -.. - .. - '
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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
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Alkyd Resins
Processing Time at 450F. __ Minutes
. Acid Value
Color Viscosity 50$. 50$ Xylol Xylol
Sward Hardness Bake 300F.
____ 1 Hr.
Control 2$ BENTHAL 4$ BENTHAL
90 100 120
12 F 10 F
8F
5-6 5-6 5
11 11 10
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(4) Cocoanut Fatty Acids Alkyd Resin -- Short Oil Modified
Reagents: ; .
.
Distilled cocoanut fatty acids (34$ modification)
2.4 moles glycerine
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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.
r-4-
DSW 305357 STLCOPCB4069511
Evaluation:
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TABLE IV
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Sward Hardness
Processing ..... Color Alkyd Resins 70% Soli
Alkyd
Time at 450F. Acid Viscosity 60#
Melamine 30# Solid
Resins .Minutes
Value 60# Xylol Xylol
l/2 Hr. 300F.
Control 3# BENTHAL . 5# BENTHAL
75 ;
- ` 18 '
90 , , 120 4
15 12
u-W ; 5-6 U *'5 u, 5
16 15 14
(5) Soy-Tung-Pentaerythritol-Maleic Anhydride-Alkyd :: . Resin -- Long Oil Modified
Reagents: :
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50$ Alkali refined soy oil
;
8# Pentaerythritol
;
20# W. W. Rosin or 12# W. . Rosin and 8% BENTHAL
17^ Tung oil
;
5% Maleic anhydride
Process:
The soy oil and pentaerythritol were subjected
to alcoholysis in the presence of a litharge
catalyst (0.10# Pb per weight of pentaerythri-
tol), 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 570F.
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Evaluation:
TABLE V
Alkyd Resin
Processing
at 500-570 F. Acid
Minutes
Value
Viscosity
50# Mineral Spirits
Air Drying Time Co-drier
Rosin type BENTHAL type
75 120, ,
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;V\.
18 10
E-F .. E
4 hours-dust free 4 hours-dust free
(6) Soy Fatty Acid-Glycerine-Maleic Anhydride-BENTHALAlkyd Resin-Short Oil Modified
Reagents:
39.4# Distilled soy fatty acids 15-8# Glycerine 15-4# Maleic anhydride 29.4# BENTHAL
DSW 305358
STLCOPCB4069512
Process and Evaluation:
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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 5f and the film baked hard in 1/4 hour
at 300F. and air dried (Pb and Co drier) in
2 hours to dust free stage.
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(7) Soy Fatty Acid-Pentaerythritol-Glycerine, BENTHAL-Alkyd Resin-Short Oil Modified""
Reagents:
4l$ "Distilled soy fatty acids
4$ Glycerine (98$)
21$ Technical pentaerythritol
32$ Phthalic anhydride
2$ BENTHAL
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Process and Evaluation:
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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 l/2 hour at 300F.
(8) Soy Oil-Pentaerythritol-BENTHAL-Phthalic AnhydrideAlkyd Resin-Short Oil Modified
Reagents:
270 g. Alkali refined soy oil 133 g* Technical pentaerythritol 180 g. Phthalic anhydride 120 g. BENTHAL
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Process and Evaluation:
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Alkali refined oil and 27 g. technical pentaerythritol were processed at 480F. 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).
DSW 305359 STLCOPCB4069513
(9) Soy 011-Pentaerythrltol-BENTHAL-Succinic Acid-Alkyd
Res in-Long Oil Modified
-.
Reagents;
240 g. Alkali refined soy oil
69 g* Technical pentaerythritol
63 g. Succinic acid
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60 g. BENTHAL
,;
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Process and
Evaluation:
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
. v:400F. and processed at 450F. for 4 hours.
: . V 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.
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For further information about BENTHAL contact the nearest Monsanto office.
MONSANTO CHEMICAL COMPANY St. Louis
Akron * Birmingham Boston Charlotte Chicago
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New York * Philadelphia Portland (Ore.) San Francisco
. v;
. Monsanto Chemicals Ltd. . London.
Seattle
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Monsanto (Canada) Ltd. Montreal Toronto Vancouver
Representatives in the Principal Cities of the World
PEM:WA-549-.5Mj 649-.5M -350- M
Printed In U.S.A.
DSW 305360 -7
STLCOPCB4069514
