US3205192A - Particulate filled coating composition of hydroxyl polyester cured with pyromellitic acid and a anhydride - Google Patents
Particulate filled coating composition of hydroxyl polyester cured with pyromellitic acid and a anhydride Download PDFInfo
- Publication number
- US3205192A US3205192A US131084A US13108461A US3205192A US 3205192 A US3205192 A US 3205192A US 131084 A US131084 A US 131084A US 13108461 A US13108461 A US 13108461A US 3205192 A US3205192 A US 3205192A
- Authority
- US
- United States
- Prior art keywords
- parts
- weight
- acid
- pyromellitic
- equivalent percent
- 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 - Lifetime
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/18—Processes for applying liquids or other fluent materials performed by dipping
- B05D1/22—Processes for applying liquids or other fluent materials performed by dipping using fluidised-bed technique
- B05D1/24—Applying particulate materials
-
- 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
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
- C08G18/4219—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from aromatic dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/006—Additives being defined by their surface area
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
Definitions
- the invention relates to resinous coating powders which are characterized by desirable flow characteristics and gel time which permit adequate coverage of articles to be coated in a minimum number of treatments and which are characterized by good corner coverage and bridging of discontinuous surfaces such as those of non-welded stators for electrodynamic machines, bundled wire structures as in wound stator end turns and the like.
- a principal object, therefore, of this invention is to provide resinous coating powders which will fulfill the above requirements, namely, to provide adequate coverage in a minimum number of treatments not only of surfaces but of corners and at one and the same time to provide such flow characteristics as will bridge and adequately coat discontinuities as above in the surface of the article to be coated with a reasonable gel time.
- the invention relates to coating powders comprising a polyester material, and filler material along with a critically balanced curing agent comprising pyromellitic 3,265,192 Patented Sept. 7, 1965 ice acid and pyromellitic dianhydride and pigment where desired.
- a resinous composition comprising a polyester material and fillers to promote flow that if pyromellitic acid and pyromellitic anhydride were used in proportions ranging from 4 to l, the total amount of curing agent ranging from about 8 to 14 parts, by weight, per 100 parts of polyester material, a material was provided which would fulfill all of the above desirable characteristics. It was further found that if the weight ratio of pyromellitic acid to pyromellitic dianhydride was more than 4, the gel time of the resulting resinous composition was too long to attain curing in a reasonable time. Furthermore, excess pyromellitic acid lowers the bonding strength.
- the polyester resin comprises (a) from about 25 to 56 equivalent percent, preferably from 36 to 50 equivalent percent, of isophthalic or terephthalic acid or a lower dialkyl ester of a member selected from the class consisting of isophthalic acid and terephthalic acid and mixtures therof, (b) from about 15 to 46 equivalent percent, and preferably from 25 to 40 equivalent percent, of ethylene glycol, and (c) from about 13 to 44 equivalent percent, and preferably from 20 to 32 equivalent percent, of a saturated aliphatic polyhydric alcohol having at least three hydroxyl groups.
- Typical of the isophthalic and terephthalic acid esters which may be used are those dialkyl esters containing from 1 to 8, and preferably from 1 to 4, carbon atoms including the dimethyl, diethyl, dipropyl, dibutyl, etc. esters.
- polyhydric alcohol and saturated aliphatic polyhydric alcohol having at least three hydroxyl groups include both polyhydric alcohols in which the hydroxyl groups are connected by a plurality of carbon to carbon linkages, as well as other alcohols having three or more hydroxyl groups, such as glycerin, 1,1,l-trimethylol ethane, sorbitol, mannitol, diglycerol, trimethylol propanes, dipentaerythritol, etc.
- the ethylene glycol can be replaced in whole or in part by other diols including but not limited to butane diol, neopentyl diol, pentane diol, etc. which will occur to those skilled in the art.
- diol is herein taken to mean such diols as well as mixtures thereof.
- equivalent percent is employed in its usual sense herein, it being the number of equivalents of the reactant divided by the total number of equivalents of all reactants times one hundred.
- the number of equiv- 4 alents of a reactant is the number of moles of the reactant multiplied by the number of functional groups Typical of the polyesters along with the others described in the above cited patent which can be used and is preferred in the practice of the invention, is one prepared from the following ingredients:
- lead acetate as an alcoholysis catalyst based on the weight of the dimethyl terephthalate is added and heating continued for about three and one-half hours to a final temperature of about 240 C.
- other alcoholysis catalysts can be used such as lead oxides, zinc oxide, cadmium acetate, cuprous acetate, zinc acetate, etc.
- the fillers employed in connection with this invention are well known and are characterized by the fact that they have a surface to volume ratio expressed in square meters per cubic centimeter of from about 100 to 500. Lesser amounts and as little as several or even less parts of the finer fillers or those of the larger surface to volume ratios can be used with each 100 parts by weight of polyester resin while up to 100 parts of the coarser fillers are usually indicated.
- the fillers which have been found useful in connection with this invention are fumed silicas, such as Cab-O-Sil made by the Godfrey L. Cabot Company, which have a surface to volume ratio of about 420 square meters per cubic centimeter. Also useful are the Micro-Cel materials, which are silicates prepared by the Johns-Manville Company.
- Micro-Cel C has a similar surface to volume ratio of 394; Micro-Cel E has a similar ratio of 232 and Micro-Cel T-35 has a like ratio of 121. Also useful are the clay-like materials, such as Attagel 20, of Minerals and Chemicals Corporation of America which has a ratio of 495 square meters per cubic centimeter. Other suitable fillers will occur to those skilled in the art.
- the pyromellitic acid and .pyromellitic dianhydride used in the present invention are of the usual commercial grades.
- polyester material there are used from up to about 90 parts of finely divided filler having the above characteristics and from about 8 to 14 parts of a curing or crosslinking agent comprising pyromellitic acid and pyromellitic dianhydride such that the weight proportions of acid to dianhydride ranges from 4 to 1 and most preferably 65/35.
- a curing or crosslinking agent comprising pyromellitic acid and pyromellitic dianhydride such that the weight proportions of acid to dianhydride ranges from 4 to 1 and most preferably 65/35.
- a dough mixer is typically employed into which the polyester material is slowly added until it has all melted and reached a temperature of from about 130 C. to 138 C., the pigment, if any being added after this temperature range is reached and with the machine still in operation. About minutes are allowed for incorporation of the pigment.
- the finely divided filler is added in convenient proportions and thoroughly mixed between additions, care being taken so that the filler does not overflow from the dough mixer.
- the composition is further mixed up to several hours.
- the cross-linking mixture is added in convenient portions over a period of between 4 to 6 minutes.
- the cross-linking agent is prepared simply by measuring out the prescribed amounts of pyromellitic acid to which is add-ed the proper amount of pyromellitic dianhydride, which latter is thoroughly dispersed throughout the acid and sealed against moisture until actual mixing with the polyester. After the preparation of the resin-filler-curing agent mixture has been completed, the material is dumped from the mixer and allowed to cool to room temperature and ground to a size as required by the particular coating procedure to be used. The primary consideration in the preparation of the materials is through admixture and blending. Equivalent methods of preparation will occur to those skilled in the art.
- the filler is to be cold-blended, this is done preferably just before use, the additional amount of finely divided filler to be cold-blended being added in convenient amounts in a usual blending machine.
- the gel time of the present materials is of the order of five minutes.
- the materials after coating can be cured with heat in the well-known manner such hardening being of a time-temperature nature.
- the coating is cured for forty-five minutes at 220 C. to 225 C. It will be realized that a step cure can be used, for example, heating at 180 C. for one-half hour and then 220 C. for a like period.
- the curing cycle is of a timetemperature nature and other useful cycles will occure to those skilled in the art.
- Example 1 There were added to a dough mixture with stirring parts by weight of the above preferred polyester, the material being added slowly until it had melted and reached a temperature of from about C. to 138 C. Ten parts of titanium dioxide pigment were added at this point with the machine in operation, five minutes being allowed for incorporation of the pigment. Next, with the dough mixture stopped, a total of 11 parts of fumed. silica or Cab-O-Sil were added in convenient proportionswith thorough mixing between additions. When the fumed silica had all been dispersed, the material was further mixed for about two hours.
- Example 2 Example 1 was repeated except that 12 parts per 100 parts of fumed silica of the above type were used. Once again, good bridging and general and corner coverage, as well as thorough coverage of continuous surfaces, were obtained.
- Example 3 Example 1 was repeated except that 14 parts by weight of fumed silicate per 100 parts of the polyester were used. Results were similar for those of Examples 1 and 2.
- Example 4 Example 1 was repeated using 6 parts of fumed silica filler. After the complete coating powder had been made and pulverized, an additional 0.5 part of fumed silica was cold blended thoroughly with the coating mixture. This material when coated on a test piece as above in a suspended bed of powder coated on corners adequately bridged discontinuities and in general provided a good coating on continuous surfaces as well.
- Example 5 Example 1 was repeated using 3 parts of titanium dioxide and a mixture of 3.5 parts pyromellitic dianhydride and 6.5 parts pyromellitic acid per 100 parts of by weight the above preferred polyester. Fumed silica in the amount of 2.5 parts was hot-blended while about 0.8 part was cold blended. The material coated very well from a suspension in the manner of the material of Example 1.
- Example 6 Example 5 was repeated using 1 part of fumed silica cold-blended to produce a good coating material.
- Example 7 Example 5 was repeated using 2.5 parts of fumed silica hot-blended and 1 part fumed silica cold-blended. Again, a good coating material resulted.
- Example 8 Example 1 was repeated using 3 parts of titanium dioxide and 2.5 parts of fumed silica per 100 parts of preferred polester.
- the curing agent was 10 parts of pyromellitic acid. While this provided a smooth flowing coating material the gel time of about 30 minutes was far too long.
- Example 9 Example 8 was repeated except that 10 parts of 60% by weight pyromellitic dianhydride and 40% pyromellitic acid were used. This material while flowing and covering very well, gelled in about two minutes after addition of the curing agent which is too short a time for production work.
- Example 10 Example 5 was repeated using 10 parts of pyromellitic dianhydride. This material gelled too quickly to form a good coating composition.
- Example 11 Example 1 was repeated except that in lieu of the fumed silica, a silicate known as Micro-Cel C having surface to volume ratio of 394 square meters per cubic centimeter was used. Once again, when test pieces were coated from a suspended bed of this material, good coatings as above were secured.
- a silicate known as Micro-Cel C having surface to volume ratio of 394 square meters per cubic centimeter was used.
- Example 12 Example 11 was repeated except that 13 parts per 100 of the silicate material of that example were used, once again, with salutary results.
- Example 13 Example 11 was repeated using 15 parts of the Micro- Cel silicate material of Example 11. Test pieces coated from a suspended bed of this material were thoroughly coated including corners as well as bridging of discontinuities.
- Example 14 Example 1 was repeated except that in lieu of the fumed silica 11 parts of a silicate known as Micro-Cel E having a surface to volume ratio of 232 square meters per cubic centimeter was used. This material provided a coating composition which thoroughly coated heated test pieces submerged therein, including corners, continuous surfaces, as well as discontinuous surfaces.
- a silicate known as Micro-Cel E having a surface to volume ratio of 232 square meters per cubic centimeter
- Example 15 Example 14 was repeated except that 15 parts of the finely divided silicate were used in lieu of 11 parts. Once again, a good coating composition was obtained which satisfactorily coated test pieces as above.
- Example 16 Example 14 was repeated except that 20 parts of the finely divided silicate were used to produce a coating composition which satisfactorily coated heated test pieces as above.
- Example 17 Example 1 was repeated except that 70 parts of a finely divided silicate known as Micro-Cel T-35 having a surface to volume ratio of 121 square meters per cubic centimeter were used. This coating composition when used to coat heated test pieces dipped in a suspended body of the composition thoroughly coated continuous surfaces, corners and discontinuous surfaces as above.
- a finely divided silicate known as Micro-Cel T-35 having a surface to volume ratio of 121 square meters per cubic centimeter were used.
- This coating composition when used to coat heated test pieces dipped in a suspended body of the composition thoroughly coated continuous surfaces, corners and discontinuous surfaces as above.
- Example 18 Example 17 was repeated except that 75 parts of the finely divided silicate were used, once again, producing a good coating composition.
- Example 19 Example 17 was repeated except that parts of the finely divided silicate of Example 17 were used to produce a coating composition having the same superior coating qualities.
- Example 20 Example 1 was repeated except that a clay-like silicate material Attagel 20 having a surface to volume ratio of 495 square meters per cubic centimeter was used in amounts of 19 parts per parts of the above preferred polyester resin.
- the coating composition when used to coat heated test pieces dipped in a suspension thereof adequately covered the continuous surfaces of the test piece as well as corners and discontinuities therein.
- Example 21 Example 20 was repeated except that 25 parts of the Attagel material were used, once again, producing a good coating composition.
- Example 22 Example 20 was repeated in all respects except that 29 parts of the Attagel were used to produce a good coating composition.
- coating compositions which are characterized by ready application to production processes. They can be used to coat continuous surfaces, at the same time adequately covering corners of the objects to be coated as Well as discontinuities in the structure to be coated.
- the coating compositions are characterized by good electrical insulating qualities as well as resistance to solvents and other chemical action. They are tough and resistant to mechanical shock such as is encountered in assembling electrical machinery, the parts of which are so coated. They are useful in general where any struc tural part or article is desired to be coated with a resinous material.
- a resinous composition comprising (1) 100 parts, by weight, of a composition comprising the curable heat reaction product of (a) from about 25 to 56 equivalent percent of a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of terephthalic acid and mixtures thereof, (b) from about 15 to 46 equivalent percent of aliphatic diol, and (c) from 13 to 44 equivalent percent of saturated aliphatic polyhydric alcohol having at least three hydroxyl groups, (II) an amount up to about 90 parts, by weight, of a finely divided filler having a surface to volume ratio ranging from about 100 to 500 square meters per cubic centimeter, and (III) from 8 to 14 parts, by weight, of a mixture of pyromellitic acid and pyromellitic dianhydride in which the ratio of pyromellitic acid to pyromellitic dianhydride ranges from about 4 to 1.
- a resinous composition comprising 100 parts, by weight, of (I) a composition comprising the curable heat reaction product of (a) 46 equivalent percent of a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of terephthalic acid, and mixtures thereof, (b) 31 equivalent percent of aliphatic diol, and (c) 23 equivalent percent of saturated aliphatic polyhydric alcohol having at least thre hydroxyl groups, (II) an amount up to about 90 parts, by weight, of a finely divided filler having a surface to volume ratio ranging from about 100 to 500 square meters per cubic centimeter, and (III) from 8 to 14 parts, by weight, of a mixture of pyromellitic acid and pyromellitic anhydride in which the ratio of pyromellitic acid to pyromellitic dianhydride ranges from about 4 to 1.
- a resinous composition comprising (I) 100 parts, by weight, of a composition comprising the curable heat reaction product of (a) from about 25 to 56 equivalent percent of a material selected from the class consisting of isophthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of terephthalic acid and mixtures thereof, (b) from about 15 to 46 equivalent percent of aliphatic diol, and (c) from 13 to 44 equivalent percent of saturated aliphatic polyhydric alcohol having at least three hydroxyl groups, (II) an amount up to about 90 parts, by weight, of a finely divided filler, and (III) from 8 to 14 parts, by weight, of a mixture of pyromellitic acid and pyromellitic dianhydride in which the ratio of pyromellitic acid to pyromellitic dianhydride ranges from about 4 to 1.
- a resinous composition comprising 100 parts, by weight, of (I) a composition comprising the curable heat reaction product of (a) 46 equivalent percent of a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of terephthalic acid, and mixtures thereof, (b) 31 equivalent percent of aliphatic diol, and (c) 23 equivalent percent of saturated aliphatic polyhydric alcohol having at least three hydroxyl groups, (II) an amount up to about parts, by weight, of a finely divided filler, and (III) from 8 to 14 parts, by weight, of a mixture of pyromellitic acid and pyromellitic anhydride in which the ratio of pyromellitic acid to pyromellitic dianhydride ranges from about 4 to 1.
- a resinous composition comprising (I) parts, by weight, of a composition comprising the curable heat reaction product of (a) from about 25 to 56 equivalent percent of dimethyl terephthalate, (b) from about 15 to 46 equivalent percent of ethylene glycol, and (c) from 13 to 44 equivalent percent of glycerine, (II) an amount up to about 90 parts, by weight, of a finely divided filler, and (III) from 8 to 14 parts, by weight, of a mixture of pyro mellitic acid and pyromellitic dianhydride in which the ratio of pyromellitic acid to pyromellitic dianhydride ranges from about 4 to l.
- a resinous composition comprising 100 parts, by weight, of (I) a composition comprising the curable heat reaction product of (a) 46 equivalent percent of dimethyl terephthalate, (b) 31 equivalent percent of ethylene glycol and (c) 23 equivalent percent of glycerine, (II) an amount up to about 90 parts, by weight, of a finely divided filler, and (III) from 8 to 14 parts, by weight, of a mixture of pyromellitic acid and pyromellitic anhydride in which the ratio of pyromellitic acid to pyromellitic dianhydride ranges from about 4 to 1.
- a resinous composition comprising (I) 100 parts, by weight, of a composition comprising the curable heat reaction product of (a) 25 to 56 equivalent percent of a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of terephthalic acid, and mixtures thereof, (b) 15 to 46 equivalent percent of aliphatic diol, and (c) 13 to 44 equivalent percent of saturated aliphatic polyhydric alcohol having at least three hydroxyl groups, (II) about 3 parts, by weight, of fumed silica, (III) 10 parts, by weight, of a mixture of 3.5 parts, by weight, of pyromellitic dianhydride and 6.5 parts, by weight, of pyromellitic acid and (IV) 3 parts, by weight, of pigment.
- a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid,
- a resinous composition comprising (I) 100 parts by weight of a composition comprising the curable heat reaction product of (a) 46 equivalent percent of a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of terephthalic acid, and mixtures thereof, (b) 31 equivalent percent of aliphatic diol, and (c) 23 equivalent percent of saturated aliphatic polyhydric alcohol having at least three hydroxyl groups, (II) about 3 parts, by weight, of fumed silica, (III) 10 parts, by weight, of a mixture of 3.5 parts, by weight, of pyromellitic dianhydride and 6.5 parts, by weight, of pyromellitic acid, and (IV) 3 parts, by weight, of pigment.
- a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of
- a resinous composition comprising (I) 100 parts, by weight, of a composition comprising the curable heat reaction product of (a) from about 25 to 56 equivalent percent of a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of terephthalic acid and mixtures thereof, (b) from about 15 to 46 equivalent percent of aliphatic diol, and (c) from 13 to 44 equivalent percent of saturated aliphatic polyhydric alcohol having at least three hydroxyl groups, (II) an amount up to about 15 parts, by weight, of fumed silica, and (III) from 8 to 14 parts, by weight, of a mixture of pyromellitic acid and pyromellitic dianhydride in which the ratio of pyromellitic acid to pyromellitic dianhydride ranges from about 4 to 1.
- a resinous composition comprising (I) 100 parts, by weight, of a composition comprising the curable heat reaction product of (a) from about 46 equivalent percent of a material selected from the class consisting of isophthalic acid, terephthalic acid, lower dialkyl ester of isophthalic acid, lower dialkyl ester of terephthalic acid and mixtures thereof, (b) from about 31 equivalent percent of aliphatic diol and (c) 23 equivalent percent of saturated aliphatic polyhydric alcohol having at least three hydroxyl groups, (II) an amount to about 15 parts, by weight, of fumed silica, and (III) from 8 to 14 parts, by Weight, of a mixture of pyromellitic acid and pyromellitic dianhydride in which the ratio of pyromellitic acid to pyromellitic dianhydride ranges from about 4 to 1.
- a resinous composition comprising (I) 100 parts of a composition comprising the curable heat reaction 10 product of (a) 46 equivalent percent dimethyl terephthalate, (b) 31 equivalent percent ethylene glycol and (c) 23 equivalent percent glycerine, (II) about 3 parts, by weight, of fumed silica, (III) 10 parts, by weight, of a mixture of 3.5 parts, by weight, of pyromellitic dianhydride and 6.5 parts, by weight, of pyromellitic acid, and (IV) 3 parts, by weight, of titanium dioxide.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Laminated Bodies (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE631377D BE631377A (US06168776-20010102-C00028.png) | 1961-08-14 | ||
US131084A US3205192A (en) | 1961-08-14 | 1961-08-14 | Particulate filled coating composition of hydroxyl polyester cured with pyromellitic acid and a anhydride |
GB29626/62A GB984153A (en) | 1961-08-14 | 1962-08-01 | Improvements in resinous polyester compositions |
FR906982A FR1347691A (fr) | 1961-08-14 | 1962-08-14 | Compositions résineuses de revêtement, comprenant un polyester |
GB16390/63A GB1047684A (en) | 1961-08-14 | 1963-04-25 | Polyester compositions |
FR932712A FR1355986A (fr) | 1961-08-14 | 1963-04-25 | Perfectionnements apportés aux compositions résineuses pour former des revêtements, et aux procédés pour leur utilisation |
DE1519155A DE1519155C3 (de) | 1961-08-14 | 1963-04-25 | Pulverförmiges und hitzehärtbares Überzugsmittel |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US131084A US3205192A (en) | 1961-08-14 | 1961-08-14 | Particulate filled coating composition of hydroxyl polyester cured with pyromellitic acid and a anhydride |
US19723862A | 1962-05-24 | 1962-05-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3205192A true US3205192A (en) | 1965-09-07 |
Family
ID=26829120
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US131084A Expired - Lifetime US3205192A (en) | 1961-08-14 | 1961-08-14 | Particulate filled coating composition of hydroxyl polyester cured with pyromellitic acid and a anhydride |
Country Status (5)
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3536516A (en) * | 1966-10-26 | 1970-10-27 | Shell Oil Co | Fluidized bed process for coating articles with polylactones |
US3723572A (en) * | 1970-03-13 | 1973-03-27 | Albert Ag Chem Werke | Synthetic resins |
DE2531094A1 (de) * | 1974-07-11 | 1976-01-22 | Teijin Ltd | Waermehaertbare und loesungsmittelloesliche estergruppen enthaltende polymerzusammensetzungen und verfahren zu deren herstellung |
US4007146A (en) * | 1974-02-15 | 1977-02-08 | Nitto Electric Industrial Co., Ltd. | Aqueous insulating varnishes |
US4011185A (en) * | 1973-04-13 | 1977-03-08 | Showa Densen Denran Kabushiki Kaisha | Aqueous insulating varnishes |
US4074006A (en) * | 1976-12-16 | 1978-02-14 | General Electric Company | Powder coatable polyester composition and electrical conductor coated therewith |
US4113898A (en) * | 1971-07-27 | 1978-09-12 | Rutgerswerke Aktiengesellschaft | Method of applying powder coatings of unsaturated branched hydroxyester resins |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1381262A (en) * | 1970-12-23 | 1975-01-22 | Unilever Ltd | Coating composition |
DE3301729A1 (de) * | 1983-01-20 | 1984-07-26 | Hoechst Ag, 6230 Frankfurt | Bindemittelmischung und deren verwendung zur herstellung von einer zweischichten-metallic-lackierung |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2936296A (en) * | 1954-12-10 | 1960-05-10 | Gen Electric | Polyesters from terephthalic acid, ethylene glycol and a higher polyfunctional alcohol |
-
0
- BE BE631377D patent/BE631377A/xx unknown
-
1961
- 1961-08-14 US US131084A patent/US3205192A/en not_active Expired - Lifetime
-
1962
- 1962-08-01 GB GB29626/62A patent/GB984153A/en not_active Expired
- 1962-08-14 FR FR906982A patent/FR1347691A/fr not_active Expired
-
1963
- 1963-04-25 GB GB16390/63A patent/GB1047684A/en not_active Expired
- 1963-04-25 FR FR932712A patent/FR1355986A/fr not_active Expired
- 1963-04-25 DE DE1519155A patent/DE1519155C3/de not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2936296A (en) * | 1954-12-10 | 1960-05-10 | Gen Electric | Polyesters from terephthalic acid, ethylene glycol and a higher polyfunctional alcohol |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3536516A (en) * | 1966-10-26 | 1970-10-27 | Shell Oil Co | Fluidized bed process for coating articles with polylactones |
US3723572A (en) * | 1970-03-13 | 1973-03-27 | Albert Ag Chem Werke | Synthetic resins |
US4113898A (en) * | 1971-07-27 | 1978-09-12 | Rutgerswerke Aktiengesellschaft | Method of applying powder coatings of unsaturated branched hydroxyester resins |
US4011185A (en) * | 1973-04-13 | 1977-03-08 | Showa Densen Denran Kabushiki Kaisha | Aqueous insulating varnishes |
US4007146A (en) * | 1974-02-15 | 1977-02-08 | Nitto Electric Industrial Co., Ltd. | Aqueous insulating varnishes |
DE2531094A1 (de) * | 1974-07-11 | 1976-01-22 | Teijin Ltd | Waermehaertbare und loesungsmittelloesliche estergruppen enthaltende polymerzusammensetzungen und verfahren zu deren herstellung |
US4074006A (en) * | 1976-12-16 | 1978-02-14 | General Electric Company | Powder coatable polyester composition and electrical conductor coated therewith |
Also Published As
Publication number | Publication date |
---|---|
DE1519155A1 (de) | 1970-03-05 |
GB1047684A (en) | 1966-11-09 |
GB984153A (en) | 1965-02-24 |
BE631377A (US06168776-20010102-C00028.png) | |
FR1347691A (fr) | 1964-01-04 |
DE1519155B2 (de) | 1973-06-20 |
DE1519155C3 (de) | 1978-05-18 |
FR1355986A (fr) | 1964-03-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3205192A (en) | Particulate filled coating composition of hydroxyl polyester cured with pyromellitic acid and a anhydride | |
US3269974A (en) | Powdered epoxy resin compositions | |
US2916403A (en) | Bonding compositions | |
US4568606A (en) | Powder coatable epoxy/polyester composition and electrical conductors coated therewith | |
JPS5923582B2 (ja) | 粉末塗料 | |
US3039987A (en) | Pulverulent coating compositions adapted for use in fluidizing processes containing epoxy resin and fillers | |
CN100582184C (zh) | 一种高压电机定子线圈及绕组端部用气干高电阻防电晕漆 | |
JPS61183367A (ja) | エポキシ樹脂およびカルボキシ化ポリエステルを主成分とした粉末被覆用組成物の製造法 | |
US3504431A (en) | Method of manufacturing insulated electrical members | |
US4214040A (en) | Cross-linkable, saturated polyester coating compositions | |
US3571491A (en) | Electrical insulating compositions of polyester resin, epoxy resin, polyvinyl acetal resin and finely divided filler | |
US3288759A (en) | Polyesters containing an organic carboxylic acid polyanhydride, and a tertiary amineas cure accelerator | |
US3366591A (en) | Thixotropic solutions of copolyesters based on 2-amino 2-methylol 1, 3-propane diol utilizing dimethyl amide solvents | |
US3058925A (en) | Process for the preparation of polyurethane foams | |
US3529034A (en) | One-part long-shelf-life epoxy-based compositions | |
US3567673A (en) | Biphenyl modified polyesterimide wire enamel | |
US3074818A (en) | Insulated conductor and method of producing same | |
US2526427A (en) | Flame and heat resistant sealing compounds | |
US2627482A (en) | Gasket material and process for making same | |
US3577274A (en) | Resin coatings containing zinc inclusions | |
JPS62104837A (ja) | 熱硬化性樹脂組成物 | |
US2945829A (en) | High temperature alkyd resin varnish | |
US3487349A (en) | Fire retardant composition and elements coated therewith | |
US3389015A (en) | Dicyclopentadiene polymer modified polyester wire enamel and varnish | |
US3115476A (en) | Process for making polyester resin aqueous suspension and resulting composition |