US20040171787A1 - Novel aromatic polysulfide and an asphalt composition containing the same - Google Patents
Novel aromatic polysulfide and an asphalt composition containing the same Download PDFInfo
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- US20040171787A1 US20040171787A1 US10/792,459 US79245904A US2004171787A1 US 20040171787 A1 US20040171787 A1 US 20040171787A1 US 79245904 A US79245904 A US 79245904A US 2004171787 A1 US2004171787 A1 US 2004171787A1
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- asphalt
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- 0 CC.CCC.OC1=CC=CC=C1.[1*]C.[2*]C.[3*]C Chemical compound CC.CCC.OC1=CC=CC=C1.[1*]C.[2*]C.[3*]C 0.000 description 10
- BUJFTKPQXSIZFX-UHFFFAOYSA-N CCC(C)(C)NC Chemical compound CCC(C)(C)NC BUJFTKPQXSIZFX-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Oc1ccccc1 Chemical compound Oc1ccccc1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/14—Polysulfides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/04—Polysulfides
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/14—Polysulfides
- C08G75/16—Polysulfides by polycondensation of organic compounds with inorganic polysulfides
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/04—Polysulfides
Definitions
- the present invention relates to a novel aromatic polysulfide and an asphalt composition containing the same. More particularly, this invention relates to a novel aromatic polysufide and an asphalt composition, an adhesive promoter and an ultraviolet absorber containing the same.
- Korean Patent Application No. 1993-14434 discloses a modified asphalt composition comprising 0.5-100 wt % of polyolefin-type metal complex based on the 100 wt % of asphalt in order to improve physical properties of prior asphalt composition.
- Korean Patent Application No. 1996-81058 reports a novel asphalt modifier with lower viscosity and odor-free character and an asphalt composition containing the above asphalt modifier, prepared in such a manner that naphtenic acid containing sulfur compound and other impurities is separated by distillation at the temperature of 70-200° C. and then remaining volatile portions are removed by passing inert gas, after which oils such as lubricating oil are added to the treated compound.
- Korean Patent Application No. 1992-8279 also sets forth a cold-mixed asphalt paving composition containing straight asphalt, gas oil and polymeric hardening agent.
- U.S. Pat. Nos. 4,244,747, 4,234,346 and 4,801,332 disclose an improved asphalt composition further comprising organic metal compound such as organic manganese compound, organic cobalt compound.
- organic metal compound such as organic manganese compound, organic cobalt compound.
- U.S. Pat. No. 4,008,095 describes an asphalt paving composition comprising microgranular undigested coal particles, bituminous coal and asphalt.
- U.S. Pat. No. 5,710,196 provides an asphalt composition comprising a graft copolymer, for example, acrylonitrile-butadiene-styrene copolymer resin so as to enhance the properties of asphalt composition. Furthermore, in order to reduce the cracking of asphalt, especially at low temperatures due to heavy loads, U.S. Pat. Nos. 4,547,399, 4,835,199 and 5,002,987 suggest compositions of elastomeric copolymers and asphalt.
- a graft copolymer for example, acrylonitrile-butadiene-styrene copolymer resin
- the conventional asphalt compositions including the aforementioned compositions fail to meet the requirement for excellent asphalt, for example, adhesiveness, water resistance, cracking-durability and abrasion resistance.
- Korean Patent Application No. 1989-18583 provides conjugated bis-1,3-diketone derivatives of benzene and Korean Patent Application No. 1989-19891 provides a composition comprising oligomer of cyclohexenilidene cyanoacetate.
- an object of this invention is to provide a novel aromatic polysulfide polymer and a method for preparing the same.
- Another object of this invention is to provide an asphalt composition comprising the above polysulfide.
- Still another object of this invention is to provide an adhesion promoter applied to polymer resin and an UV absorber.
- FIG. 1 is a graph representing the UV transmission pattern of the present polysulfide.
- This invention relates to a novel aromatic polysulfide having repeating units of the following formula (I):
- R 1 , R 2 and R 3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 1-4; and n is an integer of 2-10,000.
- the structural feature of the present aromatic polysulfide is that elements in the 6B group, oxygen and sulfur, which have two electron lone pairs, are bonded to benzene nucleus.
- the electron lone pairs of oxygen and sulfur can simultaneously interact with cations, which may be components of asphalt paving composition, through electrostatic interaction, thereby improving a variety of physical properties of an asphalt paving composition.
- the benzene ring of the polysulfide provides an ability to serve as excellent an UV absorber.
- the average molecular weight of the present polysulfide may vary depending on polymerization, but preferably in the range of 5,000 to 20,000, and more preferably in the range of 7,000 to 15,000. If the molecular weight of the polysulfide is less than 5,000, an asphalt composition and an asphalt paving composition containing such polymer may be worse in view of durability, though inducing better processability. If the molecular weight is more than 20,000, the processability may be decreased, though temperature susceptibility and durability are increased.
- the substituents in the aromatic polysulfide of this invention may be any substituents, but preferably including unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group.
- alkyl means a branched or unbranched saturated hydrocarbon chain, which can be unsubstituted or substituted.
- C 1 -C 6 straight or branched alkyl hydrocarbon chain contains 1 to 6 carbon atoms, and includes but is not limited to substituents such as methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, tert-butyl, n-pentyl, n-hexyl, and the like, unless otherwise indicated.
- the substituted alkyl has substituent(s) at one or more positions selected from halo, nitro, hydroxyl, alkyl, alkeyl, alkoxy, alkenyloxy, phenoxy, benzyloxy or aryl.
- aryl alone or in combination, is defined herein as a monocyclic or polycyclic group, preferably a monocyclic or bicyclic group, i.e. phenyl or naphthyl, which can be unsubstituted or substituted, for example, with one or more and, in particular, one to three substituents selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl.
- Some exemplary aryl groups include phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 4-methoxyphenyl, 3-trifruoromethylphenyl, 4-mitrophenyl, and the like.
- This invention also relates to a method for preparing a novel aromatic polysulfide represented by the following scheme (I), comprising the step of reaction between phenol analogue and sulfur chloride species:
- R 1 , R 2 and R 3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 1-4; and n is an integer of 2-10,000.
- the method of the present invention is performed by the reaction of phenol or phenol derivatives and sulfur chloride species, which may be classified as condensation polymerization, and the reaction condition is mild.
- the preferred reaction temperature is in the range of 50° C.-90° C.
- the method of this invention further comprises the step of adding an alkyl halide or aryl halide so as to add various substituents into the benzene nucleus.
- the sulfur chloride species used is selected from the group consisting of sulfur dichloride, sulfur monochloride, trisulfur dichloride and tetrasulfur dichloride, and the most preferred sulfur chloride species is sulfur monochloride.
- This invention provides an asphalt composition
- R 1 , R 2 and R 3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 1-4; and n is an integer of 2-10,000; and (ii) an asphalt.
- the aromatic polysulfide contained in the asphalt composition is responsible for improving various properties such as penetration, ductility, and temperature susceptibility.
- the amount of the polysulfide compound is from 0.5 to 10 wt % and the amount of the asphalt is from 90 to 99.5 wt % based on the weight of the composition. If the amount of the polysulfide is less than 0.5 wt %, the effect of adding polysulfide may be negligible, but in case of exceeding 10 wt %, cracking is caused by hardening of the composition. Furthermore, if the amount of asphalt composition is less than 90 wt %, the fluidity may be decreased, but in excess of 99.5 wt %, the durability may be dramatically decreased though strength is increased.
- This invention also relates to an asphalt paving composition
- an asphalt paving composition comprising an asphalt composition aforementioned (comprising 0.5 to 10 wt % of polysulfide having repeating units of formula (I) and 90 to 99.5 wt % of asphalt), aggregate, stone powder and sand.
- the asphalt paving composition comprises 4 to 10 wt % of the asphalt composition, 65 to 85 wt % of the aggregate, 3 to 10 wt % of the stone powder and 8 to 25 wt % of the sand.
- an useful asphalt can be any conventional asphalt in the art, and preferably includes straight asphalt, blown asphalt, lake asphalt, rock asphalt, sand asphalt, asphaltite, etc., and the most preferably includes straight asphalt.
- the amount of the asphalt composition is less than 4 wt %, the physical strength and the fluidity may be remarkably decreased, but in case of exceeding 10 wt %, the durability may be decreased.
- the asphalt paving composition exhibits excellent adhesiveness to aggregate component and better water resistance, and renders the temperature susceptibility less sensitive, thereby greatly improving durability.
- This invention also provides an adhesion promoter applied to polymer resin, which comprises a novel aromatic polysulfide having repeating units of the following formula (I):
- R 1 , R 2 and R 3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 1-4; and n is an integer of 2-10,000.
- the aromatic polysulfide serving as an adhesion promoter renders polymer resin (for example, polyethylene, polypropylene, polyisobutylene, polyvinylchloride, polystyrene, polyvinylacetate, polyisoprene) containing the polysulfide to be more adhesive.
- polymer resin for example, polyethylene, polypropylene, polyisobutylene, polyvinylchloride, polystyrene, polyvinylacetate, polyisoprene
- This invention provides an UV absorber comprising a novel aromatic polysulfide having repeating units of the following formula (I):
- R 1 , R 2 and R 3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 14; and n is an integer of 2-10,000.
- the aromatic polysulfide may function as an UV absorber in paint, plastic film, etc. to reduce sensitivity to UV, thereby extending the life span of such product.
- the resultant polymer shows about 8,000 of the average molecular weight and 80° C. of the melting point.
- the IR absorption spectrum of the polymer exhibits troughs at 3400 cm ⁇ 1 , 1440 cm ⁇ 1 , 1220 cm ⁇ 1 and 1160 cm ⁇ 1 .
- the aromatic polysulfide according to this invention was prepared in the same manner as in EXAMPLE 1, except that phenol was used instead of para-cresol.
- the final product shows about 8,000 of the average molecular weight and 80° C. of the melting point.
- aromatic polysulfide according to this invention was prepared in the same manner as in EXAMPLE 1, except that meta-cresol was used instead of para-cresol.
- the yielded product shows about 8,000 of the average molecular weight and 80° C. of the melting point.
- the aromatic polysulfide according to this invention was prepared in the same manner as in EXAMPLE 1, except that mixed cresol (including ortho-cresol, para-cresol and meta-cresol) was used instead of para-cresol.
- the yielded product shows about 8,000 of the average molecular weight and 80° C. of the melting point.
- the polysulfide of this invention may remarkably enhance the adhesion of polymer resin.
- A( ⁇ ) is absorbance
- the polysulfide of this invention represents a much lower transmittance in the UV region and therefore has excellent property as an UV absorber.
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- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Civil Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention relates to a novel aromatic polysulfide and an asphalt composition containing the same, and more particularly, to a novel aromatic polysufide having repeating units of the following formula (I), an asphalt composition, an asphalt paving composition, an adhesion promoter and an UV absorber containing the same:
The asphalt paving composition of this invention exhibits excellent adhesiveness to aggregate component and better water resistance, and renders the temperature susceptibility less sensitive, thereby greatly improving durability.
Description
- This application is a divisional patent application of U.S. Ser. No. 10/088,186 filed Jul. 25, 2002, which is a 371 of PCT/KR00/01039 filed Sep. 15, 2000 claiming priority to Korea 1999-39522 filed Sep. 15, 1999, all of which are hereby incorporated by reference.
- 1. Field of the Invention
- The present invention relates to a novel aromatic polysulfide and an asphalt composition containing the same. More particularly, this invention relates to a novel aromatic polysufide and an asphalt composition, an adhesive promoter and an ultraviolet absorber containing the same.
- 2. Description of the Related Art
- Korean Patent Application No. 1993-14434 discloses a modified asphalt composition comprising 0.5-100 wt % of polyolefin-type metal complex based on the 100 wt % of asphalt in order to improve physical properties of prior asphalt composition.
- Korean Patent Application No. 1996-81058 reports a novel asphalt modifier with lower viscosity and odor-free character and an asphalt composition containing the above asphalt modifier, prepared in such a manner that naphtenic acid containing sulfur compound and other impurities is separated by distillation at the temperature of 70-200° C. and then remaining volatile portions are removed by passing inert gas, after which oils such as lubricating oil are added to the treated compound. Korean Patent Application No. 1992-8279 also sets forth a cold-mixed asphalt paving composition containing straight asphalt, gas oil and polymeric hardening agent.
- Meanwhile, U.S. Pat. Nos. 4,244,747, 4,234,346 and 4,801,332 disclose an improved asphalt composition further comprising organic metal compound such as organic manganese compound, organic cobalt compound. Furthermore, U.S. Pat. No. 4,008,095 describes an asphalt paving composition comprising microgranular undigested coal particles, bituminous coal and asphalt.
- An asphalt composition comprising polyolefins modified with a carboxyl group and/or other functional group derived from the carboxyl group is described in Japanese Patent Kokai Nos. Sho 54-139925, Sho 59-138263, Sho 60-158256, Sho 62-181358 and Sho 62-275160.
- U.S. Pat. No. 5,710,196 provides an asphalt composition comprising a graft copolymer, for example, acrylonitrile-butadiene-styrene copolymer resin so as to enhance the properties of asphalt composition. Furthermore, in order to reduce the cracking of asphalt, especially at low temperatures due to heavy loads, U.S. Pat. Nos. 4,547,399, 4,835,199 and 5,002,987 suggest compositions of elastomeric copolymers and asphalt.
- However, the conventional asphalt compositions including the aforementioned compositions fail to meet the requirement for excellent asphalt, for example, adhesiveness, water resistance, cracking-durability and abrasion resistance.
- In the meantime, copolymer of metacrylic ester mono and vinyl monomer, which has the chromophore group representing different ultraviolet (hereinafter referred to as “UV”) absorption patterns from the metacrylic ester mono is provided as an UV absorber in Korean Patent Application No. 1988-700951. In addition, Korean Patent Application No. 1995-3408 discloses a novel bezazol compound designed for the UV absorber, prepared in such a manner that carboxylic derivatives and o-phenyldiamine are reacted at the temperatures ranging between 20° C.-90° C. in the presence of chloro sulfonic acid.
- In an effort to reduce the detrimental effect of UV by absorbing UV, Korean Patent Application No. 1989-18583 provides conjugated bis-1,3-diketone derivatives of benzene and Korean Patent Application No. 1989-19891 provides a composition comprising oligomer of cyclohexenilidene cyanoacetate.
- To solve the long-felt need in the art, the inventor has made intensive studies and as a result, developed a novel aromatic polysulfide polymer, noting that the aromatic polysulfide polymer may improve various properties of asphalt composition and serve as excellent an UV absorber.
- Accordingly, an object of this invention is to provide a novel aromatic polysulfide polymer and a method for preparing the same.
- Another object of this invention is to provide an asphalt composition comprising the above polysulfide.
- Still another object of this invention is to provide an adhesion promoter applied to polymer resin and an UV absorber.
- Other objects and advantages of this invention will become more apparent from the detailed description to follow taken in conjunction with the appended claims.
- FIG. 1 is a graph representing the UV transmission pattern of the present polysulfide.
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- wherein R1, R2 and R3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 1-4; and n is an integer of 2-10,000.
- The structural feature of the present aromatic polysulfide is that elements in the 6B group, oxygen and sulfur, which have two electron lone pairs, are bonded to benzene nucleus. The electron lone pairs of oxygen and sulfur can simultaneously interact with cations, which may be components of asphalt paving composition, through electrostatic interaction, thereby improving a variety of physical properties of an asphalt paving composition.
- The benzene ring of the polysulfide provides an ability to serve as excellent an UV absorber.
- The average molecular weight of the present polysulfide may vary depending on polymerization, but preferably in the range of 5,000 to 20,000, and more preferably in the range of 7,000 to 15,000. If the molecular weight of the polysulfide is less than 5,000, an asphalt composition and an asphalt paving composition containing such polymer may be worse in view of durability, though inducing better processability. If the molecular weight is more than 20,000, the processability may be decreased, though temperature susceptibility and durability are increased.
- The substituents in the aromatic polysulfide of this invention may be any substituents, but preferably including unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group.
- As used herein, “alkyl” means a branched or unbranched saturated hydrocarbon chain, which can be unsubstituted or substituted. For example, C1-C6 straight or branched alkyl hydrocarbon chain contains 1 to 6 carbon atoms, and includes but is not limited to substituents such as methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, tert-butyl, n-pentyl, n-hexyl, and the like, unless otherwise indicated. The substituted alkyl has substituent(s) at one or more positions selected from halo, nitro, hydroxyl, alkyl, alkeyl, alkoxy, alkenyloxy, phenoxy, benzyloxy or aryl.
- The term “aryl”, alone or in combination, is defined herein as a monocyclic or polycyclic group, preferably a monocyclic or bicyclic group, i.e. phenyl or naphthyl, which can be unsubstituted or substituted, for example, with one or more and, in particular, one to three substituents selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl. Some exemplary aryl groups include phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 4-methoxyphenyl, 3-trifruoromethylphenyl, 4-mitrophenyl, and the like.
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- wherein R1, R2 and R3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 1-4; and n is an integer of 2-10,000.
- As explained above, the method of the present invention is performed by the reaction of phenol or phenol derivatives and sulfur chloride species, which may be classified as condensation polymerization, and the reaction condition is mild. For instance, the preferred reaction temperature is in the range of 50° C.-90° C. In addition, it is preferred that the method of this invention further comprises the step of adding an alkyl halide or aryl halide so as to add various substituents into the benzene nucleus. According to the method of this invention, the sulfur chloride species used is selected from the group consisting of sulfur dichloride, sulfur monochloride, trisulfur dichloride and tetrasulfur dichloride, and the most preferred sulfur chloride species is sulfur monochloride.
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- wherein R1, R2 and R3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 1-4; and n is an integer of 2-10,000; and (ii) an asphalt.
- The aromatic polysulfide contained in the asphalt composition is responsible for improving various properties such as penetration, ductility, and temperature susceptibility. According to the preferred example, the amount of the polysulfide compound is from 0.5 to 10 wt % and the amount of the asphalt is from 90 to 99.5 wt % based on the weight of the composition. If the amount of the polysulfide is less than 0.5 wt %, the effect of adding polysulfide may be negligible, but in case of exceeding 10 wt %, cracking is caused by hardening of the composition. Furthermore, if the amount of asphalt composition is less than 90 wt %, the fluidity may be decreased, but in excess of 99.5 wt %, the durability may be dramatically decreased though strength is increased.
- This invention also relates to an asphalt paving composition comprising an asphalt composition aforementioned (comprising 0.5 to 10 wt % of polysulfide having repeating units of formula (I) and 90 to 99.5 wt % of asphalt), aggregate, stone powder and sand. According to the preferred example, the asphalt paving composition comprises 4 to 10 wt % of the asphalt composition, 65 to 85 wt % of the aggregate, 3 to 10 wt % of the stone powder and 8 to 25 wt % of the sand.
- According to this invention, an useful asphalt can be any conventional asphalt in the art, and preferably includes straight asphalt, blown asphalt, lake asphalt, rock asphalt, sand asphalt, asphaltite, etc., and the most preferably includes straight asphalt.
- In the asphalt paving composition of this invention, if the amount of the asphalt composition is less than 4 wt %, the physical strength and the fluidity may be remarkably decreased, but in case of exceeding 10 wt %, the durability may be decreased.
- The asphalt paving composition exhibits excellent adhesiveness to aggregate component and better water resistance, and renders the temperature susceptibility less sensitive, thereby greatly improving durability.
-
- wherein R1, R2 and R3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 1-4; and n is an integer of 2-10,000.
- The aromatic polysulfide serving as an adhesion promoter renders polymer resin (for example, polyethylene, polypropylene, polyisobutylene, polyvinylchloride, polystyrene, polyvinylacetate, polyisoprene) containing the polysulfide to be more adhesive.
-
- wherein R1, R2 and R3 are the same or different from each other, and independently represent H, unsubstituted alkyl group, substituted alkyl group, unsubstituted aryl group or substituted aryl group; x is an integer of 14; and n is an integer of 2-10,000.
- The aromatic polysulfide may function as an UV absorber in paint, plastic film, etc. to reduce sensitivity to UV, thereby extending the life span of such product.
- The following specific examples are intended to be illustrative of the invention and should not be construed as limiting the scope of the invention as defined by the appended claims.
- In a 5-necked flask of 5 liters fitted with 2-additional funnels, water cooled condenser, agitator and thermometer was placed para-cresol (2160 g: 20 mole) and heated to 70° C. To it was added sulfur monochloride (2835 g: 21 mole) dropwise while maintaining the reaction temperature at 50° C.-70° C. When 70% of the sulfur monochloride was added, methylene chloride (1000 ml) was introduced. Then, the remaining sulfur monochloride was added, and heated for an additional hour at 70° C.-80° C.
- Upon completion of the reaction, 2000 ml of water was added to remove any unreacted sulfur monochloride. Removal of solvent and water gave a dark yellowish solid polymer.
- The resultant polymer shows about 8,000 of the average molecular weight and 80° C. of the melting point. The IR absorption spectrum of the polymer exhibits troughs at 3400 cm−1, 1440 cm−1, 1220 cm−1 and 1160 cm−1.
- The aromatic polysulfide according to this invention was prepared in the same manner as in EXAMPLE 1, except that phenol was used instead of para-cresol.
- The final product shows about 8,000 of the average molecular weight and 80° C. of the melting point.
- The aromatic polysulfide according to this invention was prepared in the same manner as in EXAMPLE 1, except that meta-cresol was used instead of para-cresol.
- The yielded product shows about 8,000 of the average molecular weight and 80° C. of the melting point.
- The aromatic polysulfide according to this invention was prepared in the same manner as in EXAMPLE 1, except that mixed cresol (including ortho-cresol, para-cresol and meta-cresol) was used instead of para-cresol.
- The yielded product shows about 8,000 of the average molecular weight and 80° C. of the melting point.
- 1 wt %, 2 wt % and 3 wt % of aromatic polysulfide prepared in EXAMPLE 1 were respectively added to 99 wt %, 98 wt % and 97 wt % of straight asphalt, thereby making total weight percent of the final composition 100 wt %. Then while melting, each mixture was completely mixed to yield the asphalt composition at 150° C.
- 6 wt % of each asphalt composition prepared in EXAMPLE 5, 34 wt % of aggregate having 19-13 mm of particle size, 40 wt % of aggregate having less than 13 mm of particle size, 15 wt % of sand and 5 wt % of stone powder were heated and mixed to yield the asphalt paving composition at 150° C.
- The various physical properties (including penetration, ductility, softening temperature and index of temperature susceptibility) of the asphalt composition prepared in EXAMPLE 5 were evaluated based on KS M 2252, KS M 2254 and KS M 2250, respectively. The results are summarized below Table 1:
- The Marshall test on asphalt paving composition prepared in EXAMPLE 6 was carried out based on KS F 2337. And the Wheel tracking test on the asphalt paving composition prepared in EXAMPLE 6 was performed so as to evaluate resistance to rutting caused by wheels based on the Manual for Testing Qualities of Construction issued by the Korea Highway Corporation. The results are summarized below in Table 1:
TABLE 1 Amount of aromatic polysulfide(wt %) Items Physical Properties 1 2 3 Asphalt Penetration (1/10 mm, 85 82 79 Composition 25° C.) Ductility (cm, 25° C.) 150 150 150 Index of temperature 0.0263 0.0178 0.0161 susceptibility (° C.) Softening temp.(° C.) 59 67 72 Asphalt Marshall test Paving Stability(kg) 1.687 1.892 1.956 Composition Fluidity(1/100 cm) 30 28 27 Porosity(%) 4.02 4.51 4.78 Wheel tracking Ratio of 0.035 0.014 0.009 deformation(mm/min) Dynamic 921 1237 1516 stability (times/mm) - In order to evaluate the adhesion enhancement of the polysulfide, 3 wt % of the polysulfide prepared in EXAMPLE 1 were added to the PVC solution in THF (tetrahydrofuran), the resultant was then coated on a stainless steel plate and finally dried. Following the lapse of proper time, the extent of adhesion was observed with the naked eyes. It was noted that the PVC solution containing the polysulfide of this invention adhered strongly to the stainless steel plate, thus not observing peeling off, but the PVC solution without the polysulfide was peeled off from the plate with a lapse of time.
- As a result, it is confirmed that the polysulfide of this invention may remarkably enhance the adhesion of polymer resin.
- In an effort to evaluate the UV transmittance of the polysufide prepared in EXAMPLE 1, 0.016 g of the polysulfide was dissolved in 8 ml of chloroform solution and then the UV transmittance was measured with UV-spectrophotometer (HP-8454). The transmittance was calculated in the following equation and the result was plotted as shown in FIG. 1:
- Transmittance(T)=10−A(λ) Equation (I)
- wherein A(λ) is absorbance.
- As shown in FIG. 1, the polysulfide of this invention represents a much lower transmittance in the UV region and therefore has excellent property as an UV absorber.
Claims (7)
1. A novel aromatic polysulfide having repeating units of the following formula (I):
2. The novel aromatic polysulfide according to claim 1 , wherein the average molecular weight of the aromatic polysulfide is from 5,000 to 20,000.
3. A method for preparing a novel aromatic polysulfide represented by the following scheme (I), comprising the step of reaction between phenol or derivatives thereof and sulfur chloride species:
4. The method according to claim 3 , wherein the sulfur chloride species is sulfur monochloride.
5. The method according to claim 3 , wherein the method further comprises the step of adding an alkyl halide or aryl halide.
6. An adhesion promoter applied to polymer resin, which comprises a novel aromatic polysulfide having repeating units of the following formula (I):
7. An UV absorber comprising a novel aromatic polysulfide having repeating units of the following formula (I):
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/792,459 US20040171787A1 (en) | 1999-09-15 | 2004-03-03 | Novel aromatic polysulfide and an asphalt composition containing the same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1999-39522 | 1999-09-15 | ||
KR1019990039522A KR100330727B1 (en) | 1999-09-15 | 1999-09-15 | Asphalt Paving Composition Containing Aromatic Polysulfides |
US10/088,186 US6727299B1 (en) | 1999-09-15 | 2000-09-15 | Aromatic polysulfide and an asphalt composition containing the same |
US10/792,459 US20040171787A1 (en) | 1999-09-15 | 2004-03-03 | Novel aromatic polysulfide and an asphalt composition containing the same |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
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PCT/KR2000/001039 Division WO2001019724A2 (en) | 1999-09-15 | 2000-09-15 | A novel aromatic polysulfide and an asphalt composition containing the same |
US10/088,186 Division US6727299B1 (en) | 1999-09-15 | 2000-09-15 | Aromatic polysulfide and an asphalt composition containing the same |
Publications (1)
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US20040171787A1 true US20040171787A1 (en) | 2004-09-02 |
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US10/088,186 Expired - Fee Related US6727299B1 (en) | 1999-09-15 | 2000-09-15 | Aromatic polysulfide and an asphalt composition containing the same |
US10/792,459 Abandoned US20040171787A1 (en) | 1999-09-15 | 2004-03-03 | Novel aromatic polysulfide and an asphalt composition containing the same |
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US10/088,186 Expired - Fee Related US6727299B1 (en) | 1999-09-15 | 2000-09-15 | Aromatic polysulfide and an asphalt composition containing the same |
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US (2) | US6727299B1 (en) |
JP (1) | JP2003509542A (en) |
KR (1) | KR100330727B1 (en) |
CN (1) | CN1188452C (en) |
AU (1) | AU7041900A (en) |
WO (1) | WO2001019724A2 (en) |
Cited By (3)
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US20060128939A1 (en) * | 2004-12-03 | 2006-06-15 | Vijayendra Kumar | One pot process for making polymeric antioxidants |
US10294423B2 (en) | 2013-11-22 | 2019-05-21 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
US11578285B2 (en) | 2017-03-01 | 2023-02-14 | Polnox Corporation | Macromolecular corrosion (McIn) inhibitors: structures, methods of making and using the same |
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JP4903933B2 (en) * | 2000-11-29 | 2012-03-28 | アイジー工業株式会社 | Phenolic resin and its foam |
KR20030091463A (en) * | 2002-05-28 | 2003-12-03 | 주식회사 엠엔비그린어스 | Method to produce aromatic sulfide organic compound and aromatic sulfide organic compound prepared by the said method |
PL204928B1 (en) * | 2003-06-02 | 2010-02-26 | Przedsi & Eogon Biorstwo Prod | Method for production of highway engineering mixes |
FR3007766B1 (en) * | 2013-07-01 | 2017-11-03 | Arkema France | PHENOLIC POLYSULFIDES WITH IMPROVED ODOR |
CN103613940A (en) * | 2013-11-15 | 2014-03-05 | 同济大学 | Rock asphalt composite modifier as well as preparation method and application thereof |
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Publication number | Priority date | Publication date | Assignee | Title |
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US20060128939A1 (en) * | 2004-12-03 | 2006-06-15 | Vijayendra Kumar | One pot process for making polymeric antioxidants |
US10294423B2 (en) | 2013-11-22 | 2019-05-21 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
US10683455B2 (en) | 2013-11-22 | 2020-06-16 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
US11060027B2 (en) | 2013-11-22 | 2021-07-13 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
US11578285B2 (en) | 2017-03-01 | 2023-02-14 | Polnox Corporation | Macromolecular corrosion (McIn) inhibitors: structures, methods of making and using the same |
Also Published As
Publication number | Publication date |
---|---|
CN1188452C (en) | 2005-02-09 |
WO2001019724A2 (en) | 2001-03-22 |
US6727299B1 (en) | 2004-04-27 |
KR100330727B1 (en) | 2002-04-03 |
AU7041900A (en) | 2001-04-17 |
KR20000006649A (en) | 2000-02-07 |
JP2003509542A (en) | 2003-03-11 |
WO2001019724A3 (en) | 2001-08-02 |
CN1376174A (en) | 2002-10-23 |
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