CA1203938A - Additive for alkyd resin coating composition - Google Patents
Additive for alkyd resin coating compositionInfo
- Publication number
- CA1203938A CA1203938A CA000443208A CA443208A CA1203938A CA 1203938 A CA1203938 A CA 1203938A CA 000443208 A CA000443208 A CA 000443208A CA 443208 A CA443208 A CA 443208A CA 1203938 A CA1203938 A CA 1203938A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- acid
- binder
- additive
- alkyd resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4288—Polycondensates having carboxylic or carbonic ester groups in the main chain modified by higher fatty oils or their acids or by resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
Abstract
ABSTRACT
An additive for alkyd resin coating compositions which is a blend of an isocyanate isocyanurate, dibutyltindilaurate and an organic solvent. Coating compositions containing this additive are used for coating automobiles and trucks and have good initial gloss and hardness and good gloss retention on weathering.
An additive for alkyd resin coating compositions which is a blend of an isocyanate isocyanurate, dibutyltindilaurate and an organic solvent. Coating compositions containing this additive are used for coating automobiles and trucks and have good initial gloss and hardness and good gloss retention on weathering.
Description
3~33i~
TITLE
Additive for Alkyd Resin Coating Compositions BACKGROUND OF THE INVENTION
This invention relates to an additive or alkyd resin coating compositions.
Alkyd resin coating compositions are well known in the art as shown in Moffe~t et al.
U.S. 3,102,866 issued September 3, 1963, and 10 Haubert U.S. 3,228,787 issued January llr 1966.
These compositions form good quality finishes but do not cure rapidly to hard, glossy, durable finishes which are required for repairing auto and truck bodies. The use of polyisocyanates in alkyd resin compositions to improve rate of cure and physical properties of the resulting finish is shown in Miller UOS. 3,789,037 issued January 29~ 1974.
However, there is a need for a composition which forms finishes that cure rapidly, have improved gloss, hardness and gloss retention upon extended weathering.
The additive of this invention provides alkyd resin coating compositions with the aforemen-tioned improvements.
SUGARY OF THE INVENTION
. . _ . _ .
An additive for alkyd resin based coating compositions which contains about 10-50% by weight of isocyanato isocyanurate having the formula I: :
' ~3~3~
r O
OCN-R- - R~NCO
O=C\ C=O
R-NCO
n wherein R is --.C / C--,~
and n is an integer of 1-5, 0.5-5% by weight of the dibutyltin-dilaurate and I: 49.5-89.5% by weight of organlc : 20 solvent.
DESCRIPTION OF_THE INVENTION
To provide finishes of an alkyd resin : based coatinq composition that have improved hardness, inltlal gloss and gloss retent.ion and 25. rapid cure in comparison to prior art compos.itions, about 1 50% by weight, based on the weiqht of the : ooating campositions, of the additive is blended with ca~x~
sition. Generally, the additive is blended with the I composltion shortly before it is applied/ for example : 30 1 minute - 4 hours before application. If the additive is blender with the composition for a long I: period before application, gellation can occur : or viscosity can increase to a level that would l make application of the composition impossible.
35 .
' , .
' : 2 3~
The additive is a solution of 10-50~ by weight of isocyanato i~ocyanur~te having the formula OCN R R-NCO
\ N /
R-NCO
wherein R is and n is an integer of 1-5.
The preparation of this isocyanato isocyanurate is described in Schmitt et al. U.S. Patent 3,919,218 issued November 11, 1975. Preferably, 3-isocyanato-methyl-3,5,5-trimethylcyclohexyl isocyanate is used to prepare the isocyanato isocyanurate. However, other ~;~ 25 isomers can also be used. Preferably, the isocyanato isocyanurate has a isocyanate functionality of 3.0-4Ø The additive also contains 0.5-5% by weight dibutyltindilaurate and 49.5-89.5% by weight of an organic solvent.
Preferably, the additive contains about 25-30% by weight of the isocyanurate, 1-3~ by weight of dibutyltindilaurate and 69-74% by weight of toluene.
Other organic solvents can also be used such as xylene, ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone and other esters and ketones.
:
~3~8 Typical alkyd resin coating comPositions which use the additive o this invention have a binder solids content of 10-60% by weight but preferably, have a 30-50% by weight binder solids content. These compositions can be clear or can contain pigment. If pigmented, a pigment to binder ratio of about 1:100 to 150:100 is used. The pigments are dispersed in an alkyd resin solution by usual procedures such as sand grinding, attritor grinding, ball mill~g and the like and then added to the coating composition.
Examples of the great variety of pigments which are used in the coating composition are metallic oxides, preferably titanium dioxide, zinc oxide, and the like, metal hydroxides, metal flakes, metal pcwders, mates, such as lead chromate, sulfides, sulfates, carbonates, carbon black, silica, talc, china clay, iron blues, organic reds, maroons, organic dyes, lakes, and the like.
The alkyd resin used in the coatlng compo-sitions is of drying oil or fatty acids of drying oil, an estex of an organic dicarboxylic acid constituent and a polyol and can contain up to 10% by weight of an ester o-f an aromatic monocarboxylic acid and`a polyol and can contain up to 5% by weight of excess polyol.
Preferably, the alkyd resin contains 30-65% by weight of a drying oil, 30-50% by weight of an ester of polyol and an aromatic dicarboxylic acid, 2-9% by weight of an ester of an aromatic monocarboxylic acid and a polyol and 2-5~ by weight of excess polyol.
The alkyd resin is prepared by conventional techniques in which the constituents are charged into a reaction vessel along with an esterifica~ion cataIyst and, preferably, a solvent, and heated to ;~ about 80-200C for about 0.5-6 hours. Water is removed us the constituents are esterified. The resulting alkyd resin should have an acid number less than 30, and preferably, less than lS.
The following drying oils and fatty acids 33~3 of drying oils are used to prepare the alkyd resin:
tung oil, tall oil, linseed oil, dehydrated castor oil, soya oil, mixtures of these drying oils and fatty acids of these drying oils.
Any of the following acids or anhydrides or mixtures thereof are used to prepare the alkyd resin: maleic acid, maleic anhydride, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid.
The polyol used to prepare the alkyd resin is one of the following: glycerol, ethylene glycol, propylene glycol, diethylene glycol, butane diol, trimethylol propane, trimethylol ethane, pentaery-thritol, sorbitol, mannitol or mixtures of these polyols.
The following aromatic mono-carboxylic acids can be used to prepare the alkyd resin: benzoic acid, paratertiaxy butylbenzoic acid, phenol acetic :: acid, triethyl benzoic acid and the like.
The following are preferred alkyd resins used in coating composition:
An alkyd resin of 25-50% by weight of linseed oil, 5-20% by weight of tung oil 35-45% by weight of glycerol phthalate, 4-8~ by weighi of glycerol isophthalate, and
TITLE
Additive for Alkyd Resin Coating Compositions BACKGROUND OF THE INVENTION
This invention relates to an additive or alkyd resin coating compositions.
Alkyd resin coating compositions are well known in the art as shown in Moffe~t et al.
U.S. 3,102,866 issued September 3, 1963, and 10 Haubert U.S. 3,228,787 issued January llr 1966.
These compositions form good quality finishes but do not cure rapidly to hard, glossy, durable finishes which are required for repairing auto and truck bodies. The use of polyisocyanates in alkyd resin compositions to improve rate of cure and physical properties of the resulting finish is shown in Miller UOS. 3,789,037 issued January 29~ 1974.
However, there is a need for a composition which forms finishes that cure rapidly, have improved gloss, hardness and gloss retention upon extended weathering.
The additive of this invention provides alkyd resin coating compositions with the aforemen-tioned improvements.
SUGARY OF THE INVENTION
. . _ . _ .
An additive for alkyd resin based coating compositions which contains about 10-50% by weight of isocyanato isocyanurate having the formula I: :
' ~3~3~
r O
OCN-R- - R~NCO
O=C\ C=O
R-NCO
n wherein R is --.C / C--,~
and n is an integer of 1-5, 0.5-5% by weight of the dibutyltin-dilaurate and I: 49.5-89.5% by weight of organlc : 20 solvent.
DESCRIPTION OF_THE INVENTION
To provide finishes of an alkyd resin : based coatinq composition that have improved hardness, inltlal gloss and gloss retent.ion and 25. rapid cure in comparison to prior art compos.itions, about 1 50% by weight, based on the weiqht of the : ooating campositions, of the additive is blended with ca~x~
sition. Generally, the additive is blended with the I composltion shortly before it is applied/ for example : 30 1 minute - 4 hours before application. If the additive is blender with the composition for a long I: period before application, gellation can occur : or viscosity can increase to a level that would l make application of the composition impossible.
35 .
' , .
' : 2 3~
The additive is a solution of 10-50~ by weight of isocyanato i~ocyanur~te having the formula OCN R R-NCO
\ N /
R-NCO
wherein R is and n is an integer of 1-5.
The preparation of this isocyanato isocyanurate is described in Schmitt et al. U.S. Patent 3,919,218 issued November 11, 1975. Preferably, 3-isocyanato-methyl-3,5,5-trimethylcyclohexyl isocyanate is used to prepare the isocyanato isocyanurate. However, other ~;~ 25 isomers can also be used. Preferably, the isocyanato isocyanurate has a isocyanate functionality of 3.0-4Ø The additive also contains 0.5-5% by weight dibutyltindilaurate and 49.5-89.5% by weight of an organic solvent.
Preferably, the additive contains about 25-30% by weight of the isocyanurate, 1-3~ by weight of dibutyltindilaurate and 69-74% by weight of toluene.
Other organic solvents can also be used such as xylene, ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone and other esters and ketones.
:
~3~8 Typical alkyd resin coating comPositions which use the additive o this invention have a binder solids content of 10-60% by weight but preferably, have a 30-50% by weight binder solids content. These compositions can be clear or can contain pigment. If pigmented, a pigment to binder ratio of about 1:100 to 150:100 is used. The pigments are dispersed in an alkyd resin solution by usual procedures such as sand grinding, attritor grinding, ball mill~g and the like and then added to the coating composition.
Examples of the great variety of pigments which are used in the coating composition are metallic oxides, preferably titanium dioxide, zinc oxide, and the like, metal hydroxides, metal flakes, metal pcwders, mates, such as lead chromate, sulfides, sulfates, carbonates, carbon black, silica, talc, china clay, iron blues, organic reds, maroons, organic dyes, lakes, and the like.
The alkyd resin used in the coatlng compo-sitions is of drying oil or fatty acids of drying oil, an estex of an organic dicarboxylic acid constituent and a polyol and can contain up to 10% by weight of an ester o-f an aromatic monocarboxylic acid and`a polyol and can contain up to 5% by weight of excess polyol.
Preferably, the alkyd resin contains 30-65% by weight of a drying oil, 30-50% by weight of an ester of polyol and an aromatic dicarboxylic acid, 2-9% by weight of an ester of an aromatic monocarboxylic acid and a polyol and 2-5~ by weight of excess polyol.
The alkyd resin is prepared by conventional techniques in which the constituents are charged into a reaction vessel along with an esterifica~ion cataIyst and, preferably, a solvent, and heated to ;~ about 80-200C for about 0.5-6 hours. Water is removed us the constituents are esterified. The resulting alkyd resin should have an acid number less than 30, and preferably, less than lS.
The following drying oils and fatty acids 33~3 of drying oils are used to prepare the alkyd resin:
tung oil, tall oil, linseed oil, dehydrated castor oil, soya oil, mixtures of these drying oils and fatty acids of these drying oils.
Any of the following acids or anhydrides or mixtures thereof are used to prepare the alkyd resin: maleic acid, maleic anhydride, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid.
The polyol used to prepare the alkyd resin is one of the following: glycerol, ethylene glycol, propylene glycol, diethylene glycol, butane diol, trimethylol propane, trimethylol ethane, pentaery-thritol, sorbitol, mannitol or mixtures of these polyols.
The following aromatic mono-carboxylic acids can be used to prepare the alkyd resin: benzoic acid, paratertiaxy butylbenzoic acid, phenol acetic :: acid, triethyl benzoic acid and the like.
The following are preferred alkyd resins used in coating composition:
An alkyd resin of 25-50% by weight of linseed oil, 5-20% by weight of tung oil 35-45% by weight of glycerol phthalate, 4-8~ by weighi of glycerol isophthalate, and
2-5~ by weight of glycerine;
: An alkyd resin of 35-55~ by weight of soya oil, 35~50% by weight of pentaerythritol : phthalate, 5-10% by weight of pentaerythritol butyl benzoate, and 2-6% by weight of pentaerythritol;
mixtures of the above alkyd resins can be used to form a high quality composition.
: An alkyd resin of 35-55~ by weight of soya oil, 35~50% by weight of pentaerythritol : phthalate, 5-10% by weight of pentaerythritol butyl benzoate, and 2-6% by weight of pentaerythritol;
mixtures of the above alkyd resins can be used to form a high quality composition.
3~3~3 The alkyd resin coating composition can contain about 1-15% by weight, based on the weight of the binder, of an alkylated ~elamine formal-dehyde resin having 1-4 carbon atoms in the alkyd group. Typical resins are fully and partially methylated melamine formaldehyde resins, methylated-butylated melamine formaldehyde resins and the like.
To increase the rate of cure of the compo-sition, it is preferred to add about 0.1-3% by weight, based on the weight of the binder, of a metallic drier. Typical driers that are used are, for example, nickel naphthenate, cobalt naphthenate, manganese naphthenate, lead tallate; metal salts of a 6-12 carbon atom saturated aliphatic monocarboxylic acid, such as nickel octoate, cobalt octoate, nickel caprylate, nickel-2-ethylhexoate and the like.
Plasticizers can be used in the coating composition in amounts up to 10% by weight of the binder. Polymeric plasticizers which can be used are epoxidized soya bean oil, oil free and oil modified alkyds and polyesters, such as polyorotho-phthalate esters, polyalkylene adipate esters or polyarylene adipate esters. Monomeric plasticizers that can be used are butylbenzyl phthalate r dibutyl phthalate, triphenyl phosphate, 2-ethylhexylbenzyl phthalate, dicyclohexyl phthalate, dibenzyl phthalate, butylcyclohexyl phthalate, mixed benzoic acid and fatty oil acid esters of pentaerythritol poly(propylene adipate)dibenzoate, diethylene glycol .
:
~3~3313 dibenzoate, tetrabutylthiodisuccinate, butyl phthalyl butyl glycolate, acetyltributyl citrate, dibenzyl sebacate, tricresyl phosphate, toluene ethyl sulfonamide and di-2-ethylhexyl ester of hexamethylene diphthalate, di(methylcyclo-hexyl)phthalate.
One to 20~ by weight, based on the weight of the binder, of cellulose acetate butyrate can be used in the coating composition. The cellulose acetate butyrate preferably has a butyryl content of about 45-55~ by weight and a viscosity of 0.1-6 seconds determined at 25C according to ASTM-D
1343-56.
The alkyd resin composition containing the additive of this invention can be used as a primary topcoat on automobiles and trucks or as a repair coat for damaged finishes. The resulting composition can be diluted to an application viscosity with any of the conventional solvents and thinners and can be applied by conventional techniques, such as brushing, spraying, electro-static spraying, flow coating, dip coating, roller coating and the like. By choosing the desirable solvents and by varying the ratio of the solvents, the resulting composition can be provided with the physical properties required for the aforementioned application methods. The resuIting finish is then air dried or can be force dried at about 100-150C.
The resulting composition can be applied over primers, sealers and ground coats conventionally used on automobiles and trucKs or may be applied directly o'er a sanded damaged paint to repair the finish.
The following example illustrates the invention. The parts and percentages are on a weight basis unless otherwise specified.
, ~3~3~
An additive (A) was prepared by blending the following constituents:
Parts by Portion 1 Toluene S12 Dibutyltindilaurate 18 Portion 2 Isocyanato isocyanaurate(described above 237 having an i~x~anate functionality of 3-4 prepared from 3-isocyanatamethyl-3,5,5-trim~thyl-cyclohexyl isocyanate -I
Total 767 Portion 1 is mixed for lOmunute6 and then portion 2 is added and mixed for 15 minutes.
An additive (B) representative of thy prior art was prepared by blending the following constituents:
Parts by Portion 1 Weight Toluene 521 Alkyd resin(415.25 parts tall 38 oil fatty acids, 355.92 parts glycidyl ester of tertiary carboxylic acid Cardura* E ester, 0O83 epoxy xesin catalyst DBVIII
made by Argus Chemical Corp.) ~ibu~yltindilaurate 9 Portion 2 Desmodur* N Solution (75~ 130 solids solution of the biuret of hexamethylene diisocyanate in a 1:1 solvent blend of xylol and Cellosolve* acetate) __ 3Q Total 758 A white alkyd resin paint was prepared as described in Example 1 of U.S. 3,789,037, Column 4, line 57 - Column 5, line 30.
White Paint A was ormulated by blending the following *denotes trade mark Parts by Volume White alkyd resin paint Additive(A) White paint B was formulated by blending the following Parts by Weight White alkyd resin paint 8 Additive(B) A green metallic paint was formulated using the same constituents that were used to make the white alkyd resin paint except a green metallic lS mill base was substituted for the white mill base.
A green metallic paint A and a green metallic paint B were fonmulated using the same formulations as shown above to make white paints A and B except the green metallic paint was substituted for the white paint.
A dark green paint was formulated using the same constituents that were used to make the white alkyd resin paint except a green mill base was sub-stituted for the white mill base. A green paint A
and a green paint B were formulated using the same formulations as shown above to make white paints A and B except the green paint was substituted for the white paint.
A blue metallic paint was formulated using the same constituents that were used to make the white alkyd resin paint exept a blue metallic mill base was substituted for the white mill base.
A blue metallic paint A and a hlue metallic paint B were formulated using the same formulations as shown above; to make white paints A and B except the blue metallic paint was substituted for the white paLnt.
A silver paint was formulated using the same constituents that were used to make the white alkyd resin paint exept a silver mill base was 3~
substituted or the white mill base. A silver paint A and a silver paint B were formulated using the same formulations as shown above to make paints A and B
except the silver paint was substituted for the white paint.
A red paint was formulated using the same constituents that were used to make the white alkyd resin paint except a red mill base was substituted for the white mill base. A red paint A and a red paint B were formulated using the same formulations as shown above to make white paints A and B except the red paint was substituted for the white paint.
Each of the above paints were sprayed onto a steel panel primed with l mil of an alkyd resin primer pigmented with iron oxide and having a 0.5 mil thick coating of black dip alkyd resin primer over the iron oxide primer. The coating was allowed to air dry. The resulting dried coating was about 2 mils thick.
The initial gloss at 20 and 60 and nardness in knoops was measured. The panels were then exposed to outdoor weathering in Florida and the 20 and 60 gloss again was measured after 6 months, 9 months and 12 months. The data is recorded in the Table.
The data shows that initial 20and 60 gloss and hardness was higher using additive A of this invention in comparison to the prior art additive B.
The available data generally shows that the 20and 60 gloss after weathering for 6, 9 and lZ months was substantially higher with the additive of this invention in comparison to the prior art additive B.
3~3~
TABLE
, .
Gloss Aster Cutdoor ~i7eatherina ______~ .
Ini- Ini-Oil tial 6 M~s 9 r~S 12 us .
A~yd20/ Ward- 20/ 20/ 20f Resin Pamt Additive Gloss ness 61Oss loss Gloss __ __ _ , ~hiteA ~n~entior 92/97 2.5 7 V89 __ 8/46 WhiteB Prior A 86/95 0.7 51f83 __ 2f26 Green Met. A Inventior 64/91 2.2 17f56 5f26 __ Green Met. B Prior Ar 59f88 1.5 12f47 5f22 __ Dark Green A Inventior 84/93 1.3 6 V8715/54 __ Dark Green B Prior Art 78/91 ~0.7 37/714/39 __ Blue Met. Inventior 74/93 1.7 40/7S 12/44 __ Blue Met. B Prior At 55/87 0.7 28f67 9/33 __ SilverA ~lventior 88f97 2.5 13f50 __ 2/8 SilverB Prior Axt 72/94 0.6 7/40 lf6 RedA Inventior 81f94 5.6 7f42 Of9 Red~rior Art 46f81 1.9 lf30 Of16 __ : ' _______ _ :~
: :~ :
::
To increase the rate of cure of the compo-sition, it is preferred to add about 0.1-3% by weight, based on the weight of the binder, of a metallic drier. Typical driers that are used are, for example, nickel naphthenate, cobalt naphthenate, manganese naphthenate, lead tallate; metal salts of a 6-12 carbon atom saturated aliphatic monocarboxylic acid, such as nickel octoate, cobalt octoate, nickel caprylate, nickel-2-ethylhexoate and the like.
Plasticizers can be used in the coating composition in amounts up to 10% by weight of the binder. Polymeric plasticizers which can be used are epoxidized soya bean oil, oil free and oil modified alkyds and polyesters, such as polyorotho-phthalate esters, polyalkylene adipate esters or polyarylene adipate esters. Monomeric plasticizers that can be used are butylbenzyl phthalate r dibutyl phthalate, triphenyl phosphate, 2-ethylhexylbenzyl phthalate, dicyclohexyl phthalate, dibenzyl phthalate, butylcyclohexyl phthalate, mixed benzoic acid and fatty oil acid esters of pentaerythritol poly(propylene adipate)dibenzoate, diethylene glycol .
:
~3~3313 dibenzoate, tetrabutylthiodisuccinate, butyl phthalyl butyl glycolate, acetyltributyl citrate, dibenzyl sebacate, tricresyl phosphate, toluene ethyl sulfonamide and di-2-ethylhexyl ester of hexamethylene diphthalate, di(methylcyclo-hexyl)phthalate.
One to 20~ by weight, based on the weight of the binder, of cellulose acetate butyrate can be used in the coating composition. The cellulose acetate butyrate preferably has a butyryl content of about 45-55~ by weight and a viscosity of 0.1-6 seconds determined at 25C according to ASTM-D
1343-56.
The alkyd resin composition containing the additive of this invention can be used as a primary topcoat on automobiles and trucks or as a repair coat for damaged finishes. The resulting composition can be diluted to an application viscosity with any of the conventional solvents and thinners and can be applied by conventional techniques, such as brushing, spraying, electro-static spraying, flow coating, dip coating, roller coating and the like. By choosing the desirable solvents and by varying the ratio of the solvents, the resulting composition can be provided with the physical properties required for the aforementioned application methods. The resuIting finish is then air dried or can be force dried at about 100-150C.
The resulting composition can be applied over primers, sealers and ground coats conventionally used on automobiles and trucKs or may be applied directly o'er a sanded damaged paint to repair the finish.
The following example illustrates the invention. The parts and percentages are on a weight basis unless otherwise specified.
, ~3~3~
An additive (A) was prepared by blending the following constituents:
Parts by Portion 1 Toluene S12 Dibutyltindilaurate 18 Portion 2 Isocyanato isocyanaurate(described above 237 having an i~x~anate functionality of 3-4 prepared from 3-isocyanatamethyl-3,5,5-trim~thyl-cyclohexyl isocyanate -I
Total 767 Portion 1 is mixed for lOmunute6 and then portion 2 is added and mixed for 15 minutes.
An additive (B) representative of thy prior art was prepared by blending the following constituents:
Parts by Portion 1 Weight Toluene 521 Alkyd resin(415.25 parts tall 38 oil fatty acids, 355.92 parts glycidyl ester of tertiary carboxylic acid Cardura* E ester, 0O83 epoxy xesin catalyst DBVIII
made by Argus Chemical Corp.) ~ibu~yltindilaurate 9 Portion 2 Desmodur* N Solution (75~ 130 solids solution of the biuret of hexamethylene diisocyanate in a 1:1 solvent blend of xylol and Cellosolve* acetate) __ 3Q Total 758 A white alkyd resin paint was prepared as described in Example 1 of U.S. 3,789,037, Column 4, line 57 - Column 5, line 30.
White Paint A was ormulated by blending the following *denotes trade mark Parts by Volume White alkyd resin paint Additive(A) White paint B was formulated by blending the following Parts by Weight White alkyd resin paint 8 Additive(B) A green metallic paint was formulated using the same constituents that were used to make the white alkyd resin paint except a green metallic lS mill base was substituted for the white mill base.
A green metallic paint A and a green metallic paint B were fonmulated using the same formulations as shown above to make white paints A and B except the green metallic paint was substituted for the white paint.
A dark green paint was formulated using the same constituents that were used to make the white alkyd resin paint except a green mill base was sub-stituted for the white mill base. A green paint A
and a green paint B were formulated using the same formulations as shown above to make white paints A and B except the green paint was substituted for the white paint.
A blue metallic paint was formulated using the same constituents that were used to make the white alkyd resin paint exept a blue metallic mill base was substituted for the white mill base.
A blue metallic paint A and a hlue metallic paint B were formulated using the same formulations as shown above; to make white paints A and B except the blue metallic paint was substituted for the white paLnt.
A silver paint was formulated using the same constituents that were used to make the white alkyd resin paint exept a silver mill base was 3~
substituted or the white mill base. A silver paint A and a silver paint B were formulated using the same formulations as shown above to make paints A and B
except the silver paint was substituted for the white paint.
A red paint was formulated using the same constituents that were used to make the white alkyd resin paint except a red mill base was substituted for the white mill base. A red paint A and a red paint B were formulated using the same formulations as shown above to make white paints A and B except the red paint was substituted for the white paint.
Each of the above paints were sprayed onto a steel panel primed with l mil of an alkyd resin primer pigmented with iron oxide and having a 0.5 mil thick coating of black dip alkyd resin primer over the iron oxide primer. The coating was allowed to air dry. The resulting dried coating was about 2 mils thick.
The initial gloss at 20 and 60 and nardness in knoops was measured. The panels were then exposed to outdoor weathering in Florida and the 20 and 60 gloss again was measured after 6 months, 9 months and 12 months. The data is recorded in the Table.
The data shows that initial 20and 60 gloss and hardness was higher using additive A of this invention in comparison to the prior art additive B.
The available data generally shows that the 20and 60 gloss after weathering for 6, 9 and lZ months was substantially higher with the additive of this invention in comparison to the prior art additive B.
3~3~
TABLE
, .
Gloss Aster Cutdoor ~i7eatherina ______~ .
Ini- Ini-Oil tial 6 M~s 9 r~S 12 us .
A~yd20/ Ward- 20/ 20/ 20f Resin Pamt Additive Gloss ness 61Oss loss Gloss __ __ _ , ~hiteA ~n~entior 92/97 2.5 7 V89 __ 8/46 WhiteB Prior A 86/95 0.7 51f83 __ 2f26 Green Met. A Inventior 64/91 2.2 17f56 5f26 __ Green Met. B Prior Ar 59f88 1.5 12f47 5f22 __ Dark Green A Inventior 84/93 1.3 6 V8715/54 __ Dark Green B Prior Art 78/91 ~0.7 37/714/39 __ Blue Met. Inventior 74/93 1.7 40/7S 12/44 __ Blue Met. B Prior At 55/87 0.7 28f67 9/33 __ SilverA ~lventior 88f97 2.5 13f50 __ 2/8 SilverB Prior Axt 72/94 0.6 7/40 lf6 RedA Inventior 81f94 5.6 7f42 Of9 Red~rior Art 46f81 1.9 lf30 Of16 __ : ' _______ _ :~
: :~ :
::
Claims (10)
1. An additive for alkyd resin coating compositions consisting essentially of about 10-50% by weight of isocyanato iso-cyanurate having the formula wherein R is and n is an integer of 1-5, 0.5-5% by weight of dibutyltindilaurate and 49.5-89.5% by weight of an organic solvent.
2. The additive of claim 1 in which the isocyanato isocyanurate is formed from 3-isocyanato-methyl-3,5,5-trimethyl-cyclohexyl isocyanate and has an isocyanate functionality of 3.0-4Ø
3. The additive of claim 1 in which the solvent is toluene.
4. The additive of claim 1 consisting essentially of about 25-30% by weight of the isocyanato isocyanate of 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexyl isocyanate and has an isocyanate functionality of 3.0-4.0, 1-3% by weight dibutyltindilaurate and 69-74% by weight of toluene.
5. A coating composition having an alkyd resin binder containing about 1-50% by weight, based on the weight of the coating compo-sition, of the additive of claim 1.
6. The coating composition of claim 5 in which the alkyd resin consists essentially of drying oil or drying fatty acids, an ester of an organic dicarboxylic acid or anhydride and an ester of an aromatic monocarboxylic acid and a polyol.
7. The coating composition of claim 6 containing in addition to the alkyd resin about 1-15% by weight, based on the weight of the binder, of an alkylated melamine formaldehyde crosslinking resin.
8. A coating composition comprising about 10-60% by weight of a binder of an alkyd resin, an organic solvent and pigments in a pigment to binder weight ratio of about 1:100 to 150:100; wherein the binder consists essentially of about 30-65% by weight, based on the weight of the binder, of a drying oil selected from the group consisting of tung oil, tall oil, linseed oil, dehydrated castor oil, soya oil and mixtures thereof, 30-50% by weight, based on the weight of the binder, of an ester of an organic dicarboxylic acid or anhydride and a polyol;
said acid or anhydride being selected from the group consisting of maleic acid, maleic anhydride, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and mixtures thereof;
2-9% by weight, based on the weight of the binder, of an ester of an aromatic monocarboxylic acid and a polyol and 2-5% by weight, based on the weight of the binder of a polyol, wherein the polyol is selected from the group consisting of glycerol, ethylene glycol, propylene glycol, diethylene glycol, butane diol, trimethylol propane, trimethylol ethane, pentaery-thritol, sorbitol, mannitol and mixtures thereof;
and the composition contains additionally about 1-50% by weight, based on the weight of the coating composition, of the additive of claim 4.
said acid or anhydride being selected from the group consisting of maleic acid, maleic anhydride, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and mixtures thereof;
2-9% by weight, based on the weight of the binder, of an ester of an aromatic monocarboxylic acid and a polyol and 2-5% by weight, based on the weight of the binder of a polyol, wherein the polyol is selected from the group consisting of glycerol, ethylene glycol, propylene glycol, diethylene glycol, butane diol, trimethylol propane, trimethylol ethane, pentaery-thritol, sorbitol, mannitol and mixtures thereof;
and the composition contains additionally about 1-50% by weight, based on the weight of the coating composition, of the additive of claim 4.
9. The coating composition of claim 8 containing additionally about 1-15% by weight, based on the weight of the binder, of an alkylated melamine formaldehyde crosslinking agent.
10. The coating composition of claim 9 containing 0.1-3% by weight, based on the weight of the binder, of an organo metallic drier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US450,220 | 1982-12-06 | ||
| US06/450,220 US4442256A (en) | 1982-12-16 | 1982-12-16 | Additive for alkyd resin coating compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1203938A true CA1203938A (en) | 1986-04-29 |
Family
ID=23787245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000443208A Expired CA1203938A (en) | 1982-12-06 | 1983-12-13 | Additive for alkyd resin coating composition |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4442256A (en) |
| BE (1) | BE898466A (en) |
| CA (1) | CA1203938A (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605596A (en) * | 1982-12-20 | 1986-08-12 | E. I. Du Pont De Nemours And Company | Additive for coating compositions |
| AU582614B2 (en) * | 1984-12-25 | 1989-04-06 | Nippon Paint Co., Ltd. | Composition containing dispersed pigment and preparation method thereof |
| EP0379598A1 (en) * | 1988-12-14 | 1990-08-01 | BASF Corporation | Novel clearcoat composition |
| EP0375823A1 (en) * | 1988-12-16 | 1990-07-04 | BASF Corporation | Polyurethane coating composition |
| JPH0710964B2 (en) * | 1991-12-18 | 1995-02-08 | イサム塗料株式会社 | Polyurethane coating composition |
| IL116376A (en) * | 1994-12-15 | 2001-03-19 | Cabot Corp | Aqueous ink jet ink compositions containing modified carbon products |
| IL116378A (en) * | 1994-12-15 | 2003-05-29 | Cabot Corp | Non-aqueous coating or ink composition with improved optical properties containing modified carbon product and method of preparation of the composition |
| IL116379A (en) * | 1994-12-15 | 2003-12-10 | Cabot Corp | Aqueous inks and coatings containing modified carbon products |
| US5559169A (en) * | 1994-12-15 | 1996-09-24 | Cabot Corporation | EPDM, HNBR and Butyl rubber compositions containing carbon black products |
| US5807494A (en) * | 1994-12-15 | 1998-09-15 | Boes; Ralph Ulrich | Gel compositions comprising silica and functionalized carbon products |
| US5571311A (en) * | 1994-12-15 | 1996-11-05 | Cabot Corporation | Ink jet ink formulations containing carbon black products |
| US5575845A (en) * | 1994-12-15 | 1996-11-19 | Cabot Corporation | Carbon black products for coloring mineral binders |
| US5554739A (en) * | 1994-12-15 | 1996-09-10 | Cabot Corporation | Process for preparing carbon materials with diazonium salts and resultant carbon products |
| IL116377A (en) * | 1994-12-15 | 2003-05-29 | Cabot Corp | Reaction of carbon black with diazonium salts, resultant carbon black products and their uses |
| US5622557A (en) * | 1995-05-22 | 1997-04-22 | Cabot Corporation | Mineral binders colored with silicon-containing carbon black |
| WO1996037546A1 (en) * | 1995-05-22 | 1996-11-28 | Cabot Corporation | Elastomeric compounds incorporating partially coated carbon blacks |
| US6028137A (en) * | 1995-05-22 | 2000-02-22 | Cabot Corporation | Elastomeric compounds incorporating silicon-treated carbon blacks |
| US6323273B1 (en) | 1995-05-22 | 2001-11-27 | Cabot Corporation | Elastomeric compounds incorporating silicon-treated carbon blacks |
| US5958999A (en) * | 1996-04-05 | 1999-09-28 | Cabot Corporation | Ink compositions and method for generating images produced therefrom |
| US20020056686A1 (en) * | 1996-06-14 | 2002-05-16 | Agathagelos Kyrlidis | Chromatography and other adsorptions using modified carbon adsorbents |
| AU720312B2 (en) * | 1996-06-14 | 2000-05-25 | Cabot Corporation | Modified carbon adsorbents and processes for adsorption using the same |
| US5707432A (en) * | 1996-06-14 | 1998-01-13 | Cabot Corporation | Modified carbon products and inks and coatings containing modified carbon products |
| US5747562A (en) * | 1996-06-14 | 1998-05-05 | Cabot Corporation | Ink and coating compositions containing silicon-treated carbon black |
| US5698016A (en) * | 1996-06-14 | 1997-12-16 | Cabot Corporation | Compositions of modified carbon products and amphiphilic ions and methods of using the same |
| US5919855A (en) * | 1997-02-11 | 1999-07-06 | Cabot Corporation | Use of modified carbon black in gas-phase polymerizations |
| US7491419B2 (en) * | 2005-01-26 | 2009-02-17 | Ei Du Pont De Nemours & Company | Process for vehicle repair coating |
| CN102115523B (en) * | 2010-12-27 | 2012-08-08 | 嘉宝莉化工集团股份有限公司 | Modified polyurethane curing agent for alkyd resin with high hydroxyl content and preparation method thereof |
| US20220010148A1 (en) * | 2020-07-08 | 2022-01-13 | Swimc Llc | Paint tinting adjuvant with siccative for liquid colorant system |
| CN112011026B (en) * | 2020-08-21 | 2021-05-07 | 华南农业大学 | Tung oil-based positive electrode binder for lithium-sulfur battery, positive electrode for lithium-sulfur battery and preparation method of positive electrode |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3102866A (en) * | 1961-02-13 | 1963-09-03 | Du Pont | Heat-curable coating compositions |
| US3228787A (en) * | 1961-12-20 | 1966-01-11 | Du Pont | Heat curable top-coating composition |
| US3789037A (en) * | 1971-06-28 | 1974-01-29 | Du Pont | Thermosetting coating composition of an alkyd resin mixture and aliphatic polyisocyanate cross-linking agent |
| DE2325826C3 (en) * | 1973-05-22 | 1981-01-29 | Chemische Werke Huels Ag, 4370 Marl | Isocyanato-isocyanurates and the production of storage-stable solutions thereof |
| US4288351A (en) * | 1979-03-16 | 1981-09-08 | E. I. Du Pont De Nemours And Company | Water reducible alkyd resin coating composition |
| US4321169A (en) * | 1980-06-03 | 1982-03-23 | E. I. Du Pont De Nemours And Company | Water based alkyd resin coating composition containing a polyisocyanate crosslinking agent |
| US4359541A (en) * | 1981-01-19 | 1982-11-16 | Basf Wyandotte Corporation | Process for the preparation of polyisocyanurate dispersions and compositions prepared therefrom |
-
1982
- 1982-12-16 US US06/450,220 patent/US4442256A/en not_active Expired - Lifetime
-
1983
- 1983-12-13 CA CA000443208A patent/CA1203938A/en not_active Expired
- 1983-12-15 BE BE0/212051A patent/BE898466A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US4442256A (en) | 1984-04-10 |
| BE898466A (en) | 1984-06-15 |
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