MXPA99011611A - Yellow, hot melt alkyd traffic marking compositions - Google Patents

Abstract

A yellow, hot melt alkyd traffic marking composition is described. The yellow, hot melt alkyd traffic marking composition contains 10 - 25 percent by weight ofa hot melt alkyd binder, 5 - 10 percent by weight of a thermally stable 1,5- or 1,8-substituted anthraquinone colorant selected from a 1,5- or 1,8-substituted anthraquinone aromatic thioether and a 1,5- or 1,8-substituted anthraquinone aromatic thioether polyester, and 65 - 85 weight percent of a filler. The yellow, hot melt alkyd traffic marking composition of the invention may also contain other components used in traffic marking compositions, such as a reflectivity aid, a plasticizer, or an impact modifier. Other optional components are discussed below. The yellow, hot melt alkyd traffic marking compositions may be applied to any paved surface.

Description

COMPOSITIONS FOR MARKING OF PAVEMENTS, ALKYDES, YELLOWS. FUNDEN IN WARM.

The invention relates to compositions for the marking of pavements, yellow alkyds that melt hot. More particularly, the invention relates to hot melt yellow marking compositions containing a 1,5- or 1,8-substituted aromatic anthraquinone thioether or polyester. These hot melt, yellow, alkyd pavement marking compositions are generally used to mark pavement surfaces, such as roads.

BACKGROUND OF THE INVENTION The marking of yellow or white pavements used to demarcate lanes in pavements is a common signal in almost all roads. This marking ensures safety conditions for handling under varying environmental conditions. As described in US Patents 3,337,483 and 3,523,029, these white and yellow labels are formed from thermoplastic marking compositions containing an idrocarbon resin, a filler, a white or yellow pigment or dye, and glass beads. These marking compositions are applied to surfaces, such as roads, as a hot melt.

Ref .. 032323 During application, the marking compositions form a layer on the pavement surface which is allowed to cool to room temperature such that a solidified layer is formed in a short period of time. The compositions are generally applied to the pavement of roads, lots of parking lots, walkways and air tracks. Other examples of compositions for marking are described in U.S. Patent Nos. 3,897,378; 3,998,645; 4,025,476; 4,324,711; 4,406,706; 5,312,439; and 5,709.908.

Currently a large number of thermoplastic compositions for marking are used for pavement marking purposes. The conventional coloring component that has been incorporated in the. paints of yellow thermoplastic pavements, is lead chromate or cadmium yellow pigment alone or mixed with yellow chromium pigment bathed. These pigments are used in large quantities, for example, 2 pounds of lead chromate are used per gallon of marking composition. Unfortunately, these pigments contain lead, cadmium and chromium, heavy metals that are toxic to the environment. Therefore, while they are desirable from the color point of view, they are discouraging due to their toxic nature. In fact, with the growing environmental concern surrounding the use of pigments in paints and heavy metal baths, there is a pressure to replace heavy metals in hot melt marking compositions with pigments or organic dyes. Many states, such as California and Texas, have already ordered that lead chromate will be replaced where possible. Consequently, efforts have been made to use other coloring materials, ie non-toxic pigments or dyes, for the purposes of paints for yellow marking of pavements.

Efforts to replace heavy metal pigments have not been as successful as severe requirements on the performance of thermoplastic marking compositions have imposed, and consequently on the property of the dye they contain. For example, a fairly high heat resistance is required, because the thermoplastic marking compositions are applied after they are melted by heating. In addition, a climate resistance that lasts for more than a year is very essential because the thermoplastic marking compositions are typically used outdoors.

No success has been found in previous attempts to formulate hot melt labeling compositions containing organic dyes. For example, U.S. Patent Nos. 3,337,483 and 3,523,029 disclose hot melt marking compositions containing a coloring agent, such as Benzidine Yellow or Benzidine Orange. Unfortunately, Benzidine dyes and their intermediates are highly toxic and are suspected to be carcinogenic. Therefore, there is a need in the art for a hot melt marking composition that is non-toxic and safe for the environment.

BRIEF DESCRIPTION OF THE INVENTION The invention provides a composition for the marking of pavements, alkyd, yellow hot melting, which uses a dye that is non-toxic and is safe for highway workers and will not contribute to pollution of water with heavy metals. More particularly, the invention relates to the use of 1,5- or 1,8-substituted aromatic anthraquinone thioethers or 1,5- or 1,8-substituted aromatic anthraquinone thioether polyesters in pavement marking compositions. According to this, a composition of the invention for pavement marking, alkyd, hot-melting yellow, contains 10-25 weight percent of a hot-melting, alkyd binder of 5-10 weight percent of a dye thermally stable of 1,5- or 1,8-substituted aromatic anthraquinone thioether and a substituted 1,5 or 1,8-substituted aromatic anthraquinone thioether polyester, and 65-85 weight percent of a filler. A hot melt yellow, alkyd, pavement marking composition may also contain other components used in pavement marking compositions, such as a reflectivity aid, a plasticizer, or an impact modifier. Other optional components are discussed below. The compositions of the invention for the marking of pavements, alkyds, yellows that melt hot can be applied on any paved surface. The invention is described in more detail below.

DETAILED DESCRIPTION OF THE INVENTION The invention relates to a composition for the marking of pavements, alkyd,. yellow that melts hot. The composition for marking pavements can be applied on any paved road or surface.

Examples of these surfaces include roads, highways, entrance and exit ramps, elevated roads, pavements, walkways or parking lots for vehicles such as cars, bicycles, trucks, etc. Preferably, the paved surface is a porous surface such as an asphalt or concrete surface. A composition of the invention for marking pavements contains a binder, a thermally stable anthraquinone 1,5- or 1,8-substituted dye selected from a 1,5- 1,8-substituted anthraquinone aromá :: icc thioether and a polyester 1,5 or 1,8 substituted aromatic anthraquinone thioether, and an inert filler.

A hot melt, yellow, hot-melt, pavement marking composition of the invention contains 10-25 weight percent of an alkyd binder that melts hot. Preferably, the binder is present at 18-22 weight percent. Any hot-melting alkyd (eg, an alkyd, short-medium or long-chain oil, modified acrylic alkyd, or uranium) can be used as a binder in the composition of the invention for marking pavements. An example of an alkyd which can be used is a Pentanox ream, available from Pentagon Chemicals, Ltd. The hot melting alkyd binder should have a softening point in the range of 90-110 ° C.

A 1,5- or 1,8-substituted aromatic anthraquinone thioether or a thermally stable aromatic 1,5- or 1,8-substituted aromatic thioether anthraquinone polyester constitutes the cclorant of a pavement, alkylic, yellow marking composition which hot melt of the invention. This dye is present in 3-10 weight percent of the composition, preferably 5-8 weight percent. A 1,5- or 1,8-substituted aromatic anthraquinone thioether or a "thermally stable" 1,5- or 1,8-substituted aromatic anthraquinone thioether polyester is capable of supporting at least 400 ° C for five hours. Preferably a 1,5- or 1,8-substituted aromatic anthraquinone thioether or a 1,5- or 1,8-substituted aromatic thioether anthraquinone polyester are those that remain stable at 500 ° C for five hours. The 1,5- or 1,8-substituted aromatic anthraquinone thioether or a 1,5- or 1,8-substituted aromatic anthraquinone thioether polyester should also have good resistance to discoloration by prolonged exposure to the sun.

Thermally stable 1,5- or 1,8-substituted aromatic anthraquinone thioethers useful as hot, yellow thermally stable, hot-melt, pavement marking, pavement marking compositions of the invention are those of the formula I: In formula I, R is where R 1 represents a branched or unbranched saturated hydrocarbon radical containing from 6-20 carbon atoms and optionally contains one or more heteroatoms selected from oxygen, sulfur and nitrogen or a substituted phenyl group having the structure: R2 is selected from hydrogen, Ci-Cß alkyls, C al-C6 alkoxy, halogen or -COXR1; R3 represents a branched or unbranched saturated hydrocarbon radical containing from 6-20 carbon atoms and optionally containing one or more heteroatoms selected from oxygen, sulfur and nitrogen; R4 is selected from hydrogen, C3-C8 cycloalkyl, alkyl and C6-C6 aryl; X is selected from -0-, -N (R1) - and -N (R4) -; R 5 represents R 3, -0-R 3, -S-R 3, -N (R 1) R 3, or -N (R 4) R 3.

Preferred compounds of Formula I are those where R is: and where X is 0-; R 1 represents a branched or unbranched saturated hydrocarbon radical of 8-12 carbon atoms; R2 is hydrogen. Examples of various 1,5- or 1,8-substituted aromatic anthraquinone thioethers useful in hot melt, yellow, alkyd, and pavement marking compositions are shown in Table 1.

Table 1 Anthraquinone compounds 1, 5 or 1, 8-substituted for formula I can be prepared from the corresponding 1,5- or 1,8-dichloroanthraquinones by substitution of chlorine with aromatic anions thiolates using standard techniques. Preferably, the reaction takes place at elevated temperatures in a high boiling polar solvent such as, for example, dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), or diethylene glycol monopropyl ether.

The thermally stable aromatic anthraquinone 1, 5 or 1, 8-substituted thioether polyesters useful in the present invention are those having a substituted 1.5 or 1.8 substituted anthraquinone unit of formula I above, where R is : where X is selected from -CO¿R7, - (CHJ r, CO_R7, 0 (CHJnC02R7, - (CH2CH20) mR8, and - (OCH2CH2) OR8; Y is selected from - (CH nC02R7, -CH2-CdH4- C02R7, and - (CH_CH_0) mR8; R6 is selected from the hydrogen, alkyl and aryl CC ", R7 is selected from the hydrogen and C-Cr alkanoyloxy, m is in the range of 1-3; 1-4 With the proviso that two reactive polyester groups selected from hydroxy, carboxy, carboxylic acid ester, and C?-C6 alkanoyloxy are present Examples of 1,5- or 1,8-substituted aromatic anthraquinone thioether monomers are shown in Table 2.

Table 2: The 1,5- or 1,8-substituted aromatic anthraquone thioether polyester compounds contain sufficient repeating anthraquinone units to provide the desired yellow color, generally at least 10 weight percent of the anthraquinone repeating unit in the polyester. Preferably, the polyester contains 20-30 weight percent of the anthraquinome repeat unit.

The aromatic anthraquinone 1, 5 or 1,8-substituted thioether polyesters can be prepared by the reaction of anthraquinone with a carboxylic acid and polyol under polycondensation conditions as with other polyesters. The preparation of 1,5- or 1,8-substituted aromatic anthraquinone thioether polyesters is described in U.S. Patent 3,424,708; U.S. Patent 4,892,922; U.S. Patent 5,102,980; and PCT applications WO 92/13921 and WO 97/22255; each of which is incorporated here as a reference.

Suitable diol components of the 1,5- or 1,8-substituted aromatic thioether anthraquinone polyesters can be selected, for example, from ethylene glycol, 1-cyclohexanedimethanol, 1,2-propanediol, 1,3-propanediol, 1, 4-butanediol, 2,2-dimethyl-1,3-propanediol, 1,6-hexanediol, 1,2-cyclohexanediol, 1,4-cyclohexanediol, 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, Z, 8a (hydroxymethyl) - tricyclo - [5.2.1.0] - decane, where Z represents 3, 4, or 5; and diols containing one or more oxygen atoms in the chain, for example, diethylene glycol, triethylene glycol, dipropylene glycol and the like. In general, these diols contain from 2 to 18, preferably from 2 to 8, carbon atoms. The cycloliphatic diols can be used in their cis or trans configurations or as mixtures of both forms. Suitable acidic components (aliphatic, alicyclic, or aromatic dicarboxylic acids) of the 1,5- or 1,8-substituted aromatic anthraquinone thioether polyesters are selected, for example, from terephthalic acid, isophthalic acid, 1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, 1,12-dodecanedioic acid, 2,6-naphthalenedicarboxylic acid and the like. In the preparation of the polymer, the use of an acid functional derivative such as dimethyl, diethyl, or dipropyl ester of the carboxylic acid is often preferred. The anhydrides or acid halides of these acids can also be used when practical.

The 1,5- or 1,8-substituted aromatic anthraquinone thioether polyesters can be prepared according to conditions well known in the art for the formation of the polyester. For example, a mixture of one or more dicarboxylic acids, preferably aromatic dicarboxylic acids, or steres forming derivatives thereof, and one or more diols can be heated in the presence of esterification and / or polyesterification catalysts in the temperature range of between 150 ° to about 300 ° C, and atmospheric pressures to about 0.2 mm Hg. Normally the dicarboxylic acid or derivative thereof is esterified or transesterified with the diol (s) at atmospheric pressure and at temperature at the lower end of the specified range. Then the polycondensation is carried out by increasing the temperature and decreasing the pressure while the excess of diol is removed from the mixture.

In the above definitions, the term "Ci-C6 alkyl" is used to represent a saturated hydrocarbon radical containing from one to six carbon atoms, either straight or branched chain. The term "Ci-Cβ alkoxy" is used to represent an alkyl-O- (C? -C6) group. The term "C3-C8 cycloalkyl" is used to represent a saturated hydrocarbon radical containing from three to eight carbon atoms. The term "aryl" is used to represent a phenyl or phenyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogen. The term halogen is used to represent fluorine, chlorine, bromine and iodine.

In a preferred aspect, the anthraquinone dye may be first dispersed in a linear or branched polyester which is dispersed in water, such as is described in U.S. Patent Nos. 4,946,932 and 4,939,233. US Pat. No. 5,543,488 discloses branched polyesters which are dispersed in water, which is incorporated herein by reference. Branched polyesters that disperse in water offer advantages over linear polyesters that are dispersed in water, because they generally have lower viscosities that allow them to mix faster with anthraquinone dye 1,5- and 1,8-substituted and others ingredients in a composition for marking pavements of the invention. Examples of polyesters that are dispersed in water useful in this invention include the Eastman AQ-375 and Eastman AQ-1350 polyesters available from the Eastman Chemical Company, Kingsport, Tennessee. To disperse with the anthraquinone dye 1,5- and 1,8-substituted in a polyester that is dispersed in water, the dye and the polyester can be mixed with heating until a continuous phase is formed. The ratio of dye to polyester can be in the range of 1:99 to 99: 1. When such dispersed dye is employed, the disperse dye is used in the same amounts as discussed above, ie, 5-10 weight percent of the composition. Advantageously, the use of a disperse dye may allow using less dye. For example, if 5 percent of a disperse dye is used, the polyester that is dispersed in water may be preferably present as 4-4.9 weight percent of the composition and the 1,5- and 1,8-substituted anthraquinone dye in an amount of 0.1-1 weight percent. If other pigments, such as titanium dioxide, are used in the pavement marking composition, these pigments can be mixed with the 1,5- and 1,8-substituted anthraquinone dye and the polyester which is dispersed in water.

A hot melt yellow, alkyd, pavement marking composition also contains 30-85 weight percent of an inert filler. Preferably the inert filler may be present in 40-65 percent of the composition. Typical fillings include, but are not limited to, silica, sand, earth marble, calcium carbonate, alumina, quartzite, and diatomaceous earth. Mixtures of said fillers can also be used.

To provide specific enhancements, a hot-melt, alkyd, yellow hot-melt pavement marking composition of the invention may contain other typical ingredients used in pavement marking compositions. For example, a hot-melt, alkyd, yellow hot-melt pavement marking composition of the invention may contain up to 30 weight percent of a reflectivity aid such as glass beads, plastic beads or plastic bubbles. The reflectivity aid may be used in addition to or in place of all or part of the inert filler. This reflectivity assistant can have mesh sizes of 16-400. Glass beads are preferred reflectivity modifiers and preferably 15-25 weight percent are present.

One or more plasticizers may also be used in an inventive hot melt yellow, hot melt, pavement marking composition. Typically, a plasticizer may be present of 1-5 weight percent of the composition. Suitable plasticizers are, for example, phthalates such as dimethyl phthalate, diethyl phthalate, dibutyl phthalate, di-n-octylphthalate, di-isooctylphthalate, di- (2-ethylhexyl) phthalate, dinonyl phthalate, isooctyl isodecyl phthalate, diisodecyl phthalate, diallyl phthalate, butyl benzyl phthalate, and dimethoxyethyl phthalate or trimellitATES such as di-isooctyl mono-isodecyl trimellitate, tri-isooctyl trimellitate, tri-isodecyl trimellitate, and trioctyl trimellitate. A preferred plasticizer is dioctyl terephthalate.

An impact modifier (also known as viscosity modifiers) can be incorporated into the composition for marking pavements of the invention. Generally, the impact modifier is present at up to 5 weight percent, and preferably at 2-4 weight percent. Typical impact modifiers include polyethylene resins, copolyethylene propylene resins, and the like. When these resins are used, they must have a melt index at 190 ° C of 200 or less, preferably less than 100, and more preferably less than 50. The inclusion of waxes can also improve the processing of the composition for marking pavements and the dispersion of thioether dyes or aromatic anthraquinone polyesters. A preferred type as a useful impact modifier in the pavement marking composition of the invention are the Epol ene polymers, available from the Eastman Chemical Company of Kingsport, Tennessee. Epol polymers are means for reducing the molecular weight of polyethylene or polypropylene, which can be branched or chemically branched.

Additional pigments may also be included in the pavement marking composition of the invention, as are known in the art. Typically, the pigments can be present in up to 10 weight percent. For example, titanium dioxide can be added to increase opacity and brilliance. Iron sulfide can be added to enhance nighttime visibility, typically by 2-4 percent by weight.

To improve the longevity of the composition for marking pavements, antioxidants and ultraviolet (UV) absorbing compounds can also be added to the composition. The UV light absorbing compounds can also improve the light stability of the 1,5- or 1,8-substituted aromatic anthraquinone thioether or polyester dyes. Some antioxidants that can be used are, for example, 2,6-ditertiary-butyl-para-cresol and diamylphenol. Benzophenones, such as 2,4-dihydroxybenzophenone, represent typical UV light absorbing compounds. Generally, such antioxidants and UV absorbing compounds are employed at combined levels of less than 1 weight percent and often less than 0.5 weight percent.

A hot-melting, alkyd, yellow-based pavement composition is typically prepared by intimate combination of ingredients such that the hot-melting alkyd binder becomes the continuous phase. No special mixing techniques are required. A blender that is capable of being heated to about 200 ° C and 400 ° C is sufficient to melt and mix the above ingredients from thirty minutes to one hour. As is known in the art, the temperature, the heating time and the appliances may depend on the particular composition that is prepared. Typically, the pavement marking composition is melted and mixed in place, just before being applied to the road surface. The hot melting alkyd binder is first melted, and then the 1,5-or 1,8-substituted aromatic anthraquinone thioether or polyester dye can be added together with the filler. Any other ingredient can also be added. Alternatively, the thioether or aromatic anthraquinone polyester 1,5-? 1,8- substituted can be melted and mixed with hot melting alkyd and / or impact modifier (eg, polyethylene) if employed, to produce a binder / dye portion, generally in the form of spheres or pieces preformed Then, these spheres or preformed pieces can be melted and mixed with the other ingredients of the composition for marking pavements before being used. 0, the other ingredients of the composition for flooring, alkyd, hot melting yellow can also be premixed to produce a portion of the filling. The binder / dye portion can be melted and mixed with the filling portion at the point of use. Generally, 17-25 percent of the binder / dye portion is combined with 65-83 weight percent of the filler portion.

The following examples are intended to illustrate, but not limit the invention. It is contemplated and understood that other hot-melting alkyd binders, thioether dyes or 1,5- or 1,8-substituted aromatic anthraquinone polyesters, fillers, impact modifiers, etc., such as discussed above can be used for a flooring, alchemical, yellow hot melting of the invention.

Example 1 Preparation of 1,5-bis (2-ethylexyloxycarbonyl-1-phenylthio) 9,10-anthraquinone They were added to 5 parts of 1,5-bis (2-carboxy-phenylthio) 9,10-anthraquinone in 50 parts of 2-ethyl-l hexanol, 0.5 parts of concentrated sulfuric acid. The mixture was stirred vigorously at 175 ° C for 20 hr. During this period, the solution became clear and colored red.The mixture was allowed to cool to room temperature at which point the product crystallized.The solids were recovered by filtration and washed with methanol to obtain 6.8 parts of 1.5. bis (2-ethylexyloxycarbonyl-1-phenylthio) 9,10-anthraquinone (95% yield).

Example 2 To 95 parts by weight of terephthalic acid (TPA), 59 parts by weight of butanediol (BD), and 60 parts by weight of 1,5-bis (2-carboxy-1-phenylthio) 9, 10-anthraquinone (dye) were added 75 parts per million titanium in the form of titanium tetraisopropoxide. This mixture was heated with stirring at 200 ° C for 2 hours and additionally heated at 220 ° C for two more hours. During this time, water and tetrahydrofuran were generated and collected by means of a dry ice condenser. The temperature rose to 250 ° C and the pressure was decreased in a period of 15 min to 0.002 psi (0.1 mm Hg). After 35 minutes at this temperature and pressure, the heating was removed, the pressure was returned to atmospheric and the resulting dark reddish yellow polymer was cooled. The polymer yield was 200 parts by weight of poly (butylene terephthalate) copolymerized with 305 weight of dye.

Example 3 A mixture of 1,5-bis (2-carboxyphenylthio) 9,10-anthraquinone (25.60 g, 0.05 mol), 1,2-ethanediol dimethanesulfate (10.90 g, 0.05 mol), potassium carbonate (13.82 g, 0.10 mol) and N-methyl-2-pyrrolidinone (NMP) (400mL) were heated with stirring at 125 ° C for one hr The reaction mixture was poured into methanol (600mL) and stirred The yellow polymeric product was recovered by filtration and washing with methanol, until the filtrate was essentially clear.The paste moistened in ethanol was slurried in 1.0 L of water, the mixture was acidified with the addition of acetic acid and the yellow product was collected by filtration, washed with water hot and dried in air (21.16g product). By gel permeation chromatography (GPC) the polymer product has an average molecular weight of 6.083 and a molecular weight of 3,000 and a polydispersity value of 2.03.

Example 4 To 99 parts of Eastman AQ-375 (a linear polyester resin, which is dispersed in water) was added 1 part of poly (yellow) dye prepared in Example 3 in the form of powder and 1 part of TiQ_. This mixture was mixed perfectly at 450 ° F. It was found that the melt viscosity of the mixture was 92,000 cP.

Example 5 To 99 parts of Eastman AQ-1350 (a branched polyester resin that is dispersed in water) was added 1 part of poly (yellow) dye prepared in Example 3 in the form of powder and 1 part of Ti02. This mixture was mixed perfectly at 450 ° F. It was found that the melt viscosity was 5,400 cP. This represents a significant reduction in the melt viscosity corresponding to an increase in the mobility of the compound.

Example 6 To 15 parts of alkyd resin (Pentanox resin, ring and ball softening point of 90-100 ° C), 5 parts of castor oil, 20 parts of glass beads, 5 parts of TiO and 50 parts of CaC03 (Georgia Marble) were added 5 parts of the mixture of Example 4. This gave a satisfactory pavement marking composition after vigorous mixing.

Use 7 To 15 parts of alkyd resin (Pentanox resin, ring and ball softening point 90-100 ° C), 5 parts of castor oil, 20 parts of glass beads, 5 parts of TiO_ and 50 parts of CaC03 (Georgia Marble) parts of the mixture of Example 5 were added. This gave a satisfactory pavement marking composition with good flowability and ease of mixing.

EXAMPLE 8 A mixture of 77.87 parts of 3-m.ercapta-1,2,4-triazole, 96.75 parts of potassium carbonate, and 96.99 parts of 1,5-dichloroquinoline in 1322 parts of dimethylformamide (DMF) was mixed and heated at 100 ° C and maintained at that temperature for 6 hours. The reaction mixture was then cooled to room temperature and poured into 4000 parts of water. The mixture was acidified with HCl and then filtered on a paste filter. The solids were washed with water and dried. The product yield is typically 85-90 ...

Example 9 Preparation of 1,5-bis (2-carboxyphenylthio) anthraquinone A mixture of 28 parts of 1,5-dichloroanthraquinone, 34 parts of 2-mercaptobenzoic acid, 38 parts of potassium carbonate in 750 parts of diethylene glycol monopropyl ether was stirred and heated to reflux for 4 hours, the mixture was cooled to about 100 ° C and poured into 750 parts of water. Acetic acid (50 parts) was added in the form of a drop to precipitate the product. The mixture was heated to ~ 5 ° C and filtered hot. The solids were repeatedly washed with hot water and then dried. The typical yield of the product is 90-95 _.

It is noted that in relation to this date, the best method known by the applicant to carry out the aforementioned invention, is the conventional one for the manufacture of the objects to which it relates.

Having described the invention as above, the contents of the following are claimed as property.

Claims (1)

1. CLAIMS A hot melt yellow, alkyd, pavement marking composition, characterized in that it comprises: 10-25 weight percent of a hot-melting alkyd binder, 5-10 weight percent of a thermally stable anthraquinone dye , 1,5- or 1, 8-substituted selected from an aromatic anthraquinone thioether 1,5 or 1, 8 substituted and of a 1,5 or 1,8 substituted aromatic anthraquinone thioether polyester, 30-85 weight percent of a filler. 0-30 weight percent of a reflectivity aid, 0-5 weight percent of a plasticizer, and 0-5 weight percent of an impact modifier. A hot melt, yellow, alkyd, pavement marking composition of claim 1, characterized in that it additionally comprises: 15-25 weight percent of a reflectivity aid selected from among glass beads, plastic beads and bubbles. plastic, 1-5 weight percent of a plasticizer, 2-5 weight percent of an impact modifier selected from among low molecular weight polyethylene, low molecular weight polypropylene, and low molecular weight copolyethylene propylene. A hot melt yellow, alkyd, and pavement marking composition of claim 1, characterized in that in the substituted aromatic anthrachone thioether 1,5 or 1,8 dye of the formula: where R is where R1 represents a branched or unbranched hydrocarbon radical containing from 6-20 carbon atoms and optionally containing one or more heteroatoms selected from oxygen, sulfur and nitrogen or a substituted phenyl group having the structure: where R 2 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen or -C0XR 1; R3 represents a branched or unbranched saturated hydrocarbon radical containing from 6-20 carbon atoms and optionally one or more heteroatoms selected from oxygen, sulfur and nitrogen; R4 is selected from hydrogen, C3-C8 cycloalkyl; alkyl and aryl C? -C6; X is selected from -Ot-, -N (Rl) - and -N (R4) -; R 5 represents R 3, -0-R 3, -S-R 3, -N (R 1) R 3, or -N (R 4) R 3. A hot-melt, alkyd, yellow hot-melt pavement marking composition of claim 3, characterized in that R is and where X is 0-; R 1 represents a branched or unbranched saturated hydrocarbon radical of 8-12 carbon atoms; R2 is hydrogen. A hot melt yellow, alkyd, pavement marking composition of claim 1, characterized in that the substituted 1,5- or 1-anthraquinone dye is a substituted 1,5 or 1,8-substituted anthraquinone aromatic thioether polyester. , which has a substituted unit of substituted anthraquinone 1.5 or 1.8 of the formula: where R is: and where X is selected from -CO_R7, - (CH • CO_R7, Q (CHJnC02R7, - (CH_CH: 0) mR8, and - (OCH.CHJ OR8; Y is selected from - (CHJ nC02R7, -CH_-C .H4-CO.R7, and - (CHCH_0) mR8; R6 is selected from hydrogen, alkyl and aryl C? -C6, R7 is selected from hydrogen and C_-C3 alkyl, substituted C _ -C. , cycloalkyl C _ - CT and aryl, R 8 is selected from hydrogen, Ci-C β alkanoyloxy, m is in the range of 1-3, and n in the range of 1-4, with the proviso that two reactive polyester groups selected from between hydroxy, carboxy, carboxylic acid ester, and Ci-Cβ alkanoyloxy are present. A composition for marking pavement, alkyd, hot melting yellow of claim 1, characterized in that the 1,5- or 1,8-substituted anthraquinone dye is dispersed in a linear or branched polyester which is dispersed in water.