# US 11,898,037 B2 · Rejuvenating compositions for asphalt applications and methods of manufacturing the same

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- Number: US 11,898,037 B2
- Document ID: US11898037B2
- Status: Granted
- Kind: B2
- Application number: 16/227,915
- Filed: 2018-12-20
- Published: 2019-04-25
- Granted: 2024-02-13
- Earliest claimed: 2015-02-27
- Assignees: Cargill, Incorporated
- Applicants: Cargill, Incorporated
- Inventors: Todd L. Kurth; Scott Nivens; Christopher Patrick Stevermer; Hassan Ali Tabatabaee
- Web page: https://patentgrep.com/patent/US11898037B2

## CPC

- C08L 91/00: Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08H 3/00: Vulcanised oils, e.g. factice
- C08L 91/02: Vulcanised oils, e.g. factice
- C08L 95/00: Compositions of bituminous materials, e.g. asphalt, tar, pitch
- C08L 95/005: {Aqueous compositions, e.g. emulsions}
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 195/00: Coating compositions based on bituminous materials, e.g. asphalt, tar, pitch
- E01C 7/26: mixed with other materials, e.g. cement, rubber, leather, fibre {(fibrous material reinforcements for bituminous paving E01C11/165)}
- E01C 7/262: {with fibrous material, e.g. asbestos; with animal or vegetal admixtures, e.g. leather, cork (E01C7/265 takes precedence)}
- E01C 11/005: {Methods or materials for repairing pavings (E01C7/35 takes precedence; for concrete coverings E01C7/147; for bituminous coverings E01C7/187; devices for repair works E01C23/06; repairing bridge floorings E01D22/00)}
- C08L 2205/02: containing two or more polymers of the same C08L -group
- C08L 2205/08: containing additives to improve the compatibility between two polymers
- C08L 2555/10: Design or test methods for bitumen or asphalt mixtures, e.g. series of measures, procedures or tests to obtain a bitumen or asphalt mixture having preset defined properties, general or international test methods, procedures or standards
- C08L 2555/22: Asphalt produced above 140°C, e.g. hot melt asphalt
- C08L 2555/24: Asphalt produced between 100°C and 140°C, e.g. warm mix asphalt
- C08L 2555/28: Asphalt produced between 0°C and below 65°C, e.g. cold mix asphalt produced between 0°C and 35°C
- C08L 2555/34: Recycled or waste materials, e.g. reclaimed bitumen, asphalt, roads or pathways, recycled roof coverings or shingles, recycled aggregate, recycled tires, crumb rubber, glass or cullet, fly or fuel ash, or slag
- C08L 2555/52: Aggregate, e.g. crushed stone, sand, gravel or cement
- C08L 2555/64: Oils, fats or waxes based upon fatty acid esters, e.g. fish oil, olive oil, lard, cocoa butter, bees wax or carnauba wax
- C08L 2555/70: from natural non-renewable resources
- C08L 2555/80: Macromolecular constituents
- C08L 2555/82: from natural renewable resources, e.g. starch, cellulose, saw dust, straw, hair or shells
- C08L 2555/84: Polymers comprising styrene, e.g. , polystyrene, styrene-diene copolymers or styrene-butadiene-styrene copolymers
- C11B 3/00: Refining fats or fatty oils
- G01N 25/4866: {by using a differential method}
- Y02A 30/30: in transportation, e.g. on roads, waterways or railways
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- E01C: CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR (forming roads or like surfaces by compacting or grading snow or ice E01H)
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Disclosed herein are rejuvenating compositions for asphalt applications. In one aspect, the rejuvenating composition comprises a polymerized oil having a polymeric distribution ranging from about 2 to about 80 wt % oligomer content and Hildebrand solubility ranging from about 6 to about 12. In another aspect, the rejuvenating composition comprises an oil having a Hildebrand solubility ranging from about 6 to about 12 and a flash point ranging from about 100° C. to about 400° C. In yet another aspect, the rejuvenating composition comprises a modified oil having a Hildebrand solubility ranging from about 6 to about 12 and a flash point ranging from about 100° C. to about 400° C.

## Claims

### Claim 1

A rejuvenating composition for asphalt applications, comprising a polymerized oil comprising a starting material oil crosslinked with elemental sulfur, the polymerized oil comprising a Hildebrand solubility ranging from about 6 to about 12 and a flash point ranging from about 100° C. to about 400° C., wherein the polymerized oil has a sulfur content of 0.01 wt % to 8.7 wt %, and all sulfur-containing crosslinks present in the polymerized oil are between molecules of the starting material oil.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the starting material oil is a biorenewable oil comprising soybean oil, canola oil, rapeseed oil, castor oil, tall oil, sunflower oil, palm oil, peanut oil, safflower oil, corn oil, corn stillage oil, lecithin, an animal-based oil, or a combination thereof.

### Claim 3 (depends on 1)

The composition of claim 1, further comprising a biorenewable oil or petroleum-based oil.

### Claim 4 (depends on 1)

The composition of claim 1, further comprising a modified oil.

### Claim 5 (depends on 1)

The composition of claim 1, further comprising asphalt, recycled asphalt, or a combination thereof.

### Claim 6 (depends on 1)

The composition of claim 1, further comprising thermoplastic, elastomeric, or plastomeric polymers, polyphosphoric acid, anti-stripping additives, warm mix additives, emulsifiers, fibers, or a combination thereof.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the composition is an emulsion.

### Claim 8 (depends on 7)

The composition of claim 7, further comprising asphalt, recycled asphalt, or a combination thereof.

### Claim 9 (depends on 7)

The composition of claim 7, further comprising thermoplastic, elastomeric, or plastomeric polymers, polyphosphoric acid, anti-stripping additives, warm mix additives, emulsifiers, fibers, or a combination thereof.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the polymerized oil is achieved via a bodying reaction, a blowing reaction, or a reaction with a polyglycerol ester.

### Claim 11 (depends on 1)

The composition of claim 1, wherein the crosslinking comprises heating to about 130° C. to about 250° C.

### Claim 12 (depends on 1)

The composition of claim 1, wherein the polymerized oil is a modified oil.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the oil comprises a polymeric distribution ranging from about 2 to about 80 wt % oligomer content.

### Claim 14 (depends on 1)

A method comprising applying the composition of claim 1 to an existing pavement surface.

### Claim 15 (depends on 1)

A method comprising applying the composition of claim 1 to treat RAS or RAP and further mixing the treated recycled asphalt shingles (RAS) or recycled asphalt pavement (RAP) with virgin asphalt thereby obtaining a rejuvenated asphalt blend.

### Claim 16 (depends on 1)

A method comprising applying the composition of claim 1 as part of a cold patching material, a high performance cold patch or cold mix application that contains recycled asphalt thereby obtaining treated RAS or RAP.

### Claim 17 (depends on 1)

A method comprising applying the composition of claim 1 to milled asphalt pavement during cold-in-place recycling of the milled asphalt pavement during or hot-in-place recycling of the milled asphalt pavement.

### Claim 18 (depends on 1)

The composition of claim 1, wherein the polymerized oil crosslinked with the sulfur-containing compound is a liquid at 40° C.

### Claim 19

A rejuvenating composition for asphalt applications, comprising a polymerized oil comprising a starting material oil crosslinked with elemental sulfur, the polymerized oil comprising a Hildebrand solubility ranging from about 6 to about 12 and a flash point ranging from about 100° C. to about 400° C., wherein the polymerized oil has a sulfur content of 0.01 wt % to 8.7 wt %.

### Claim 20

A rejuvenating composition for asphalt applications, comprising a polymerized oil comprising a starting material oil crosslinked with elemental sulfur, the polymerized oil comprising a Hildebrand solubility ranging from about 6 to about 12 and a flash point, ranging from about 100° C. to about 400° C. the polymerized oil having a sulfur content of 0.01 wt % to 8.7 wt %, wherein the starting material oil comprises a biorenewable, previously modified, or functionalized oil comprising soybean oil, canola oil, rapeseed oil, castor oil, tall oil, sunflower oil, palm oil, peanut oil, safflower oil, corn oil, corn stillage oil, lecithin, an animal-based oil, or a combination thereof.