US2268022A - Drying oil composition - Google Patents

Drying oil composition Download PDF

Info

Publication number
US2268022A
US2268022A US266959A US26695939A US2268022A US 2268022 A US2268022 A US 2268022A US 266959 A US266959 A US 266959A US 26695939 A US26695939 A US 26695939A US 2268022 A US2268022 A US 2268022A
Authority
US
United States
Prior art keywords
oil
drying
wrinkling
oils
glyceride
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
Application number
US266959A
Inventor
Folsom E Drummond
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
New Wrinkle Inc
Original Assignee
New Wrinkle Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by New Wrinkle Inc filed Critical New Wrinkle Inc
Priority to US266959A priority Critical patent/US2268022A/en
Application granted granted Critical
Publication of US2268022A publication Critical patent/US2268022A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/28Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for wrinkle, crackle, orange-peel, or similar decorative effects

Definitions

  • My invention relates to coating compositions and more particularly to compositions of the drying oil and wrinkle finish type.
  • the invention is applicable broadly in the compounding of varnishes, paints, enamels, printing inks.
  • One object of this invention is to provide a conjugated double bond modified oil composition wherein the drying of a coating film comprising the modified oil vehicle is controlled by varying the constituents so as to produce either a wrinkle film or a smooth non-wrinkling film as desired. Another object is to accelerate the polymerization and oxidation of paint oil compositions by the incorporation of certain amounts of unsaturated fatty acid glycerides having poly-conjugated double bond molecular structure.
  • Another object is to provide a coating composition of the character described comprising unsaturated fatty acid compounds of the polyconjugated double bond type modified by the addition of metallic driers having improved drying properties.
  • Another object is to control the rapidity of drying of the coating film by varying the percentage amount of unsaturated organic compounds having conjugated double bonds introduced into the coating.
  • Still another object of this invention is to control the drying rate and wrinkling effect by varying the amount and type of poly-conjugated double bond glyceride compounds whereby the non-wrinkling oils may be made to dry to a wrinkle finish.
  • a further object is to provide a method of producing fast drying coating composition of the drying oil type without the necessity of introducing metallic driers.
  • Another object is to provide a method of treating drying and semi-drying oils so as to substantially enhance their drying properties.
  • a still further object is to provide a method of treating non-wrinkling oils so as to make them function as wrinkling oils. In this way the use of high priced blown China-wood and oiticica oils or wrinkling resins may be avoided.
  • Figure 1 is a view in perspective illustrating a surface having applied thereto a coating composition of this invention which is dried to a plain smooth surface;
  • Figure 2 is a similar view showing a like coating presenting a wrinkle finish
  • Figures 3 and 4 are enlarged fragmentary sectional views taken on the line 3-3 of Figure 1 and 4 4 of Figure 2, respectively.
  • 5 designates a panel or suitable base material provided with a coating film 6 of the rapid drying smooth surface type.
  • a like base material having a wrinkle surface finish coating 1 is illustrated in Figures 2 and 4.
  • the surface comprises irregular folds 8 which are formed in the skin portion of the coating film due to the rapid drying of the surface.
  • compositions of the drying oil type according to my invention, utilization is made principally of the triglycerides of the fatty acids having polyconjugated double bond molecular structure as heretofore mentioned.
  • the oil and glyceride are combined by heating so that the product contains sufficient amount of glyceride having 3 or more conjugated double bond linkage so that the desired drying properties can be obtained.
  • the percentage by weight of the glyceride added varies with each oil but may comprise upwards of 50 per cent by weight for producing wrinkling drying oil products. In this case the percentage amount of triglyceride is preferably in the neighborhood of 90 per cent of the paint oil composition.
  • the triglycerides are used since they produce the most pronounced drying effect.
  • the use of di-unsaturated glycerides in place of the tri or mixtures thereof may be eme ployed if desired.
  • Further utilization may be made of the fatty acids alone when a suflicient amount of glycerol or glyceride constituents is present in the oil mixture. in the absence of glycerol or glyceride compound do not exhibit good drying properties.
  • Formulationsmade using the glycerides having only 2 conjugated double bonds produce a drying oil paint vehicle having superior drying and waterproofing qualities to those of linseed oil. Addition of suitable metallic driers to these modified drying oil vehicles will further enhance the drying of the composition to a smooth-non-wrinkling film when applied and air dried or baked at low temperatures.
  • non-wrinkling oil vehicles are as follows:
  • the mixture of oil and glyceride is heated to incorporate the fatty acid glyceride to form a homogeneous composition. Heating the oil and glyceride mixture to a temperature of 350 to 450 degrees F. for one-half to one hour is suflicient to produce a satisfactory product.
  • Suitable driers or drier combinations may be incorporated in the modified oil vehicles if desired, such as the acetate, resinate or linoleate of cobalt, manganese or lead.
  • the glyceride modified oil vehicles illustrated in Examples 1 to 8 may be compounded with suitable resins, natural or synthetic; for example, kauri, congo, damar, pontianak, manila, elemi, mastic or synthetic resins such as Cumar," ester gum, phenol formaldehyde resin, glycerolphthalic acid resin'particularly of the oilsoluble type or mixtures of these.
  • suitable resins natural or synthetic; for example, kauri, congo, damar, pontianak, manila, elemi, mastic or synthetic resins such as Cumar," ester gum, phenol formaldehyde resin, glycerolphthalic acid resin'particularly of the oilsoluble type or mixtures of these.
  • the coating compositions employing the glyceride modified oil vehicles may be either air dried or baked to produce a dry, smooth, flexible, water-resistant film, A baking temperature range between 250 to 400 degrees F. for one-half to one and one-half hours may be employed.
  • modified oil vehicles comprising large percentages of fatty acid glycerides having 3 or more conjugated double bond molecular structure are employed.
  • Typical examples of wrinkling oil-yehicles are:
  • Example 9 x Per cent by weight Linseed oil 5 to 25 Triglyceryl-elaeostearate to '15 azespaa Erample 10 Linseed oil to 25 Trigiyceryl-lacanate 95 to 75
  • Example 11 Linseed oil 20 to 40 Triglyceryl octodecatetraenate 80 to 60
  • Example 12 Perilla oil 5 to 25 Triglyceryl-elaeostearate 95 to 75
  • Example 13 Perilla oil 5 to 25 Triglyceryl-licanate 95 to 75
  • Example 14 Perilla oil 20 to 40 Triglyceryl-octodecatetraenate 80 to 60
  • Example 16 Soya bean oil 5 to 20 Triglyceryl-licanate 95 to 80
  • Example 17 Soya bean oil to 25 Triglyceryl-octodecatetraenate 90 to 75
  • the fatty acid glycerides are thoroughly incorporated with
  • raw, refined or blown drying oils may be used in preparing the wrinkling oils.
  • blown or prepoiymerized oils less amount of the glyceride constituent is required to produce a product which will dry in a given time.
  • the glycerides having triple or more conjugated double bonds may also be blended with tung oil or oiticica, which are wrinkling oils, to modify their wrinkling characteristics.
  • tung oil or oiticica which are wrinkling oils, to modify their wrinkling characteristics.
  • incorporation of natural or synthetic resins and driers may be made.
  • compositions comprising the modified drying oil may be applied as a film by .flowing or spraying and baked at temperatures of the order of 250 to 350 degrees F. for one to two hours to produce a wrinkle finish. Enamels require somewhat longer and higher temperatures of baking.
  • paint oil vehicles petroleum naphtha, toluol, or mixtures of the two may be employed.
  • the u se err-various natural or synthetic resins may be made to provide-7 a resinous type coating'zcompos'ition.
  • Various resins may be added to the composition in order to modify the properties comprising natural and synthetic resins such as heretofore mentioned.
  • a suitable plasticizing agent such as castor oil, dibutyl phthalate or tricresyl-phosphate may be incorporated.
  • the paint oil compositions herein illustrated can also be used in making enamels and similar pigmented compositions. To produce such compositions 5 to 25% of a suitable pigment is ground into the glyceride modified oil or resinous oil composition and the required amount of thinner such as petroleum naphtha and the like is added.
  • Clear varnish-like compositions may be applied finish or a smooth glossy surface depending upon whether-the oils are those of Examples 1 to 8 or the wrinkling oils of Examples 9 to 17.
  • Thin coatings may also be applied over materials such as paper, foil, parchment and the like to produce a light transmitting sheet applicable for making various articles such as window shades, drapes, lamp shades and the like.
  • the coating compositions of this invention may also be applied 'over metal, wood, pottery, glass, paper, leather and the like, and baked or air dried to a flexible, tough film.
  • Various ornamental effects of the wrinkle finishes can be produced by varying the percentage of poly-conjugated double bond glyceride constituent in the paint oil. Other modified results of the finish may be obtained by variations in the method of applying the compositions. Further one or more coats may be applied to an article and dried and thereafter cellulose lacquer or like composition disposed v,
  • non-wrinkling drying oil is intended to encompass drying oils and semidrying oils of the type used in the examples hereinbefore set forth.
  • drying oil having incorporated therewith a sufficient amount of a siccative to produce a wrinkling composition on drying, said siccative consisting of a fatty acid glyceride of an acid having the conjugated double bond structural alkyl radical and a: is equal to 4.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Lubricants (AREA)

Description

Patented Dec. 30, 1941 Folsom E. Drummond, Dayton, Ohio, assignor, by mesne assignments, to New Wrinkle, Inc., Wilmington, Del., a corporation of Delaware Application April 10, 1939, Serial No. 266,959
Claims.
My invention relates to coating compositions and more particularly to compositions of the drying oil and wrinkle finish type. The invention, however, is applicable broadly in the compounding of varnishes, paints, enamels, printing inks.
and the like.
One object of this invention is to provide a conjugated double bond modified oil composition wherein the drying of a coating film comprising the modified oil vehicle is controlled by varying the constituents so as to produce either a wrinkle film or a smooth non-wrinkling film as desired. Another object is to accelerate the polymerization and oxidation of paint oil compositions by the incorporation of certain amounts of unsaturated fatty acid glycerides having poly-conjugated double bond molecular structure.
Another object is to provide a coating composition of the character described comprising unsaturated fatty acid compounds of the polyconjugated double bond type modified by the addition of metallic driers having improved drying properties.
Another object is to control the rapidity of drying of the coating film by varying the percentage amount of unsaturated organic compounds having conjugated double bonds introduced into the coating.
Still another object of this invention is to control the drying rate and wrinkling effect by varying the amount and type of poly-conjugated double bond glyceride compounds whereby the non-wrinkling oils may be made to dry to a wrinkle finish.
A further object is to provide a method of producing fast drying coating composition of the drying oil type without the necessity of introducing metallic driers.
Another object is to provide a method of treating drying and semi-drying oils so as to substantially enhance their drying properties.
A still further object is to provide a method of treating non-wrinkling oils so as to make them function as wrinkling oils. In this way the use of high priced blown China-wood and oiticica oils or wrinkling resins may be avoided.
In the drawing:
Figure 1 is a view in perspective illustrating a surface having applied thereto a coating composition of this invention which is dried to a plain smooth surface;
Figure 2 is a similar view showing a like coating presenting a wrinkle finish;
Figures 3 and 4 are enlarged fragmentary sectional views taken on the line 3-3 of Figure 1 and 4 4 of Figure 2, respectively.
Referring to the drawing in detail, 5 designates a panel or suitable base material provided with a coating film 6 of the rapid drying smooth surface type. A like base material having a wrinkle surface finish coating 1 is illustrated in Figures 2 and 4. The surface comprises irregular folds 8 which are formed in the skin portion of the coating film due to the rapid drying of the surface.
I have discovered that the drying of coating compositions can be controlled so as to produce either rapid drying, smooth surface compositions or films drying to a wrinkle finish by varying the amount of compounds present having conjugated double bond structure as illustrated by the general formula: (CH=CH), where a: represents 2 or more. Examples of compounds which comprise conjugated double bonds are unsaturated acids such as follows:
CH:(CH2) 5-(CH=CH) 2(CH2) 1COOH Iso-linoleic acid I Iso-linolenic acid CHs-(CHz) a(CH=CH) 3(CH2) qcoon Elaeostearic acid Licanic acid CI-IzCHz-(CH=CH) 4-(CH2) 7COOH Octadecatetraenoic acid in the compound the more readily reactive it is.'
Similarly under the same conditions the greater vthe percentage amount of conjugated double bond compound in the coating film the drying time.
In the formulation of rapid drying coating the shorter is compositions of the drying oil type, according to my invention, utilization is made principally of the triglycerides of the fatty acids having polyconjugated double bond molecular structure as heretofore mentioned.
employed are: 1
(a) Triglyceryl-isolinoleate (b) Triglyceryl-isolinolenate CHa(CH:)r-(CH=CH):CHr-CH=CH(CHr)1COO-C J By incorporating various amounts of the triunsaturated glycerides in the conventional non-. wrinkling paint oils the drying properties may be greatly enhanced and the waterproofing and flexibility of the product increased. Further by compounding the paint oils with a sufiicient amount of fatty acid triglyceride compounds having three or more conjugated double bonds in the molecular structure drying oils. such as linseed, perilla, soya bean and the like, paint oils may be made to function as a wrinkling oil similar to China-wood oil. For bringing this about the oil and glyceride are combined by heating so that the product contains sufficient amount of glyceride having 3 or more conjugated double bond linkage so that the desired drying properties can be obtained. The percentage by weight of the glyceride added varies with each oil but may comprise upwards of 50 per cent by weight for producing wrinkling drying oil products. In this case the percentage amount of triglyceride is preferably in the neighborhood of 90 per cent of the paint oil composition.
Preferably the triglycerides are used since they produce the most pronounced drying effect. However, the use of di-unsaturated glycerides in place of the tri or mixtures thereof may be eme ployed if desired. Further utilization may be made of the fatty acids alone when a suflicient amount of glycerol or glyceride constituents is present in the oil mixture. in the absence of glycerol or glyceride compound do not exhibit good drying properties.
Formulationsmade using the glycerides having only 2 conjugated double bonds produce a drying oil paint vehicle having superior drying and waterproofing qualities to those of linseed oil. Addition of suitable metallic driers to these modified drying oil vehicles will further enhance the drying of the composition to a smooth-non-wrinkling film when applied and air dried or baked at low temperatures.
Typical examples of non-wrinkling oil vehicles are as follows:
The fatty acids alone- Typical examples which illustrate the glycerides Example 1 Per cent by weight Linseed oil .15 to 40 Triglyceryl-isolinoleate to 60 Example 2 Linseed oil 15 to 40 'lnglyceryl-isolinolenate 85 to 60 Example 3 Perillaoil 15 to 40 Triglyceryl-isolinoleate 85 to 60 Example 4 Perilla oil 15 to 40 Triglyceryl-isolinolenate 85 to 60 Example 5 Soya bean oil 10 to 30 'Iriglyceryl-isolinoleate to 70 Example 6 Soya bean oil 10 to 30 Triglyceryl-isolinolenate 90 to 70 Example 7 China-wood oil 40 to 60 Triglyceryl-isolinoleate 60 to 40 Example 8 China-wood oil 40 to 60 Triglyceryl-isolinolenate 60 to 40 In the examples of paint and varnish vehicles given the drying and semi-drying oils may be used either in the raw state, refined or in blown condition as desired. Various mixtures of the different oils also may be utilized. Further use may be made of other oils, for example oiticica, P ppy seed oil, sunfloweroil, as well as fish and marine mammal oils heretofore used in paint and varnish coating compositions.
The mixture of oil and glyceride is heated to incorporate the fatty acid glyceride to form a homogeneous composition. Heating the oil and glyceride mixture to a temperature of 350 to 450 degrees F. for one-half to one hour is suflicient to produce a satisfactory product.
Suitable driers or drier combinations may be incorporated in the modified oil vehicles if desired, such as the acetate, resinate or linoleate of cobalt, manganese or lead.
The glyceride modified oil vehicles illustrated in Examples 1 to 8 may be compounded with suitable resins, natural or synthetic; for example, kauri, congo, damar, pontianak, manila, elemi, mastic or synthetic resins such as Cumar," ester gum, phenol formaldehyde resin, glycerolphthalic acid resin'particularly of the oilsoluble type or mixtures of these. The coating compositions employing the glyceride modified oil vehicles may be either air dried or baked to produce a dry, smooth, flexible, water-resistant film, A baking temperature range between 250 to 400 degrees F. for one-half to one and one-half hours may be employed.
For the production of similar coating compositions wherein the film readily dries to a wrinkle finish surface, modified oil vehicles comprising large percentages of fatty acid glycerides having 3 or more conjugated double bond molecular structure are employed.
Typical examples of wrinkling oil-yehicles are:
Example 9 x Per cent by weight Linseed oil 5 to 25 Triglyceryl-elaeostearate to '15 azespaa Erample 10 Linseed oil to 25 Trigiyceryl-lacanate 95 to 75 Example 11 Linseed oil 20 to 40 Triglyceryl octodecatetraenate 80 to 60 Example 12 Perilla oil 5 to 25 Triglyceryl-elaeostearate 95 to 75 Example 13 Perilla oil 5 to 25 Triglyceryl-licanate 95 to 75 Example 14 Perilla oil 20 to 40 Triglyceryl-octodecatetraenate 80 to 60 Example 15 Soya bean oil 5 to 20 Triglyceryl-elaeostearate 95 to 80 Example 16 Soya bean oil 5 to 20 Triglyceryl-licanate 95 to 80 Example 17 Soya bean oil to 25 Triglyceryl-octodecatetraenate 90 to 75 In compounding the oil compositions of Examples 9 to 1'7, the fatty acid glycerides are thoroughly incorporated with the oils to provide a homogeneous drying oil vehicle in a similar manner to that described in Examples 1 to 8. It will be understood also that raw, refined or blown drying oils may be used in preparing the wrinkling oils. In general when using blown or prepoiymerized oils less amount of the glyceride constituent is required to produce a product which will dry in a given time.
The glycerides having triple or more conjugated double bonds may also be blended with tung oil or oiticica, which are wrinkling oils, to modify their wrinkling characteristics. In like manner the incorporation of natural or synthetic resins and driers may be made.
The compositions comprising the modified drying oil may be applied as a film by .flowing or spraying and baked at temperatures of the order of 250 to 350 degrees F. for one to two hours to produce a wrinkle finish. Enamels require somewhat longer and higher temperatures of baking. For thinning the paint oil vehicles, petroleum naphtha, toluol, or mixtures of the two may be employed.
Further in utilizing the wrinkling oils of Example 9 to 17 the u se err-various natural or synthetic resinsmay be made to provide-7 a resinous type coating'zcompos'ition. Various resins may be added to the composition in order to modify the properties comprising natural and synthetic resins such as heretofore mentioned. when it is desired to give added flexibility to the films, a suitable plasticizing agent such as castor oil, dibutyl phthalate or tricresyl-phosphate may be incorporated. The paint oil compositions herein illustrated can also be used in making enamels and similar pigmented compositions. To produce such compositions 5 to 25% of a suitable pigment is ground into the glyceride modified oil or resinous oil composition and the required amount of thinner such as petroleum naphtha and the like is added.
Clear varnish-like compositions may be applied finish or a smooth glossy surface depending upon whether-the oils are those of Examples 1 to 8 or the wrinkling oils of Examples 9 to 17. Thin coatings may also be applied over materials such as paper, foil, parchment and the like to produce a light transmitting sheet applicable for making various articles such as window shades, drapes, lamp shades and the like. The coating compositions of this invention may also be applied 'over metal, wood, pottery, glass, paper, leather and the like, and baked or air dried to a flexible, tough film. Various ornamental effects of the wrinkle finishes can be produced by varying the percentage of poly-conjugated double bond glyceride constituent in the paint oil. Other modified results of the finish may be obtained by variations in the method of applying the compositions. Further one or more coats may be applied to an article and dried and thereafter cellulose lacquer or like composition disposed v,
thereover.
It will be understood that I desire to comprehend within my invention such modifications as come within the scope of my invention as described and the appended claims.
It will be further understood that the term "non-wrinkling drying oil," as used in the claims, is intended to encompass drying oils and semidrying oils of the type used in the examples hereinbefore set forth.
Having thus fully described my invention, what I claim as new and desire to secure by Letters Patent is:
1. A drying oil vehicle for coating compositions comprising a non-wrinkling drying oil having admixed therewith a triglyceride accelerator consisting of a high molecular weight unsaturated fatty acid triglyceride compound having conjugated double bond linkage of the formula (-CH=CH):,wherein a: is equal to 4.
2. A drying oil vehicle for coating compositions 7 comprising a non-wrinkling drying oil and a drying accelerator incorporated therewith consisting of an unsaturated fatty acid glyceride compound having conjugated double bond linkage of the formula (CH=CH)=, wherein a: is equal to 4.,
3. A coating composition comprising a nonwrinkling drying oil to which is added a wrinkle producing fatty acid glyceride comprising poly- 7 conjugated double bond linkage in the molecular structure together with a metallic drier for producing a wrinkling composition, said double bond linkage being of the formula (--CH=CH-)z, wherein a: is equal to 4.
4. A coating composition adapted for use as a quick drying coating, comprising a non-wrinkling.
drying oil having incorporated therewith a sufficient amount of a siccative to produce a wrinkling composition on drying, said siccative consisting of a fatty acid glyceride of an acid having the conjugated double bond structural alkyl radical and a: is equal to 4.
FOLSOM E. DRUMMOND.
US266959A 1939-04-10 1939-04-10 Drying oil composition Expired - Lifetime US2268022A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US266959A US2268022A (en) 1939-04-10 1939-04-10 Drying oil composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US266959A US2268022A (en) 1939-04-10 1939-04-10 Drying oil composition

Publications (1)

Publication Number Publication Date
US2268022A true US2268022A (en) 1941-12-30

Family

ID=23016699

Family Applications (1)

Application Number Title Priority Date Filing Date
US266959A Expired - Lifetime US2268022A (en) 1939-04-10 1939-04-10 Drying oil composition

Country Status (1)

Country Link
US (1) US2268022A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2472152A (en) * 1944-08-05 1949-06-07 Union Oil Co Diesel engine fuel
US2640783A (en) * 1950-02-02 1953-06-02 Nat Printing Ink Res Inst Ink having improved drying properties
US2744833A (en) * 1952-08-27 1956-05-08 Ohio Commw Eng Co Wrinkle drying oil siccative
US2744832A (en) * 1952-07-17 1956-05-08 Ohio Commw Eng Co Wrinkle drying oil siccative

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2472152A (en) * 1944-08-05 1949-06-07 Union Oil Co Diesel engine fuel
US2640783A (en) * 1950-02-02 1953-06-02 Nat Printing Ink Res Inst Ink having improved drying properties
US2744832A (en) * 1952-07-17 1956-05-08 Ohio Commw Eng Co Wrinkle drying oil siccative
US2744833A (en) * 1952-08-27 1956-05-08 Ohio Commw Eng Co Wrinkle drying oil siccative

Similar Documents

Publication Publication Date Title
US1950417A (en) Wrinkle finish for flexible articles
US2268022A (en) Drying oil composition
US1999413A (en) Method of decorating surfaces
US2381653A (en) Method of producing rapid drying
US1976191A (en) Wrinkle resin finish
US1831323A (en) Ornamented article and process of making same
US1689892A (en) Wrinkling finish
US1896594A (en) Wrinkle coating
US1864763A (en) Ornamental finish
US1955355A (en) Asphaltic coating compositions and materials coated therewith
US2268002A (en) Paint vehicle
US2294703A (en) Wrinkle finish composition and method of making
US2344189A (en) Wrinkling enamel and method of making
US2744832A (en) Wrinkle drying oil siccative
US2467229A (en) Coating process and article
US2123206A (en) Synthetic resins and compositions containing them
US2394498A (en) Wrinkle finish composition
US1883408A (en) Wrinkle finish coating
US2110072A (en) Mixed synthetic glyceride varnish
US2319507A (en) Composition containing wood oil ob
US2275239A (en) Pigment paste
US2332031A (en) Method of producing irregular finishes
US1818576A (en) Rubber coated fabric and process of making it
US2373177A (en) Wrinkle finish drying compositions
US1995957A (en) Asphaltic coating composition and material coated therewith