US3895172A - Method of waterproofing with asphalts containing polyamines - Google Patents

Method of waterproofing with asphalts containing polyamines Download PDF

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US3895172A
US3895172A US29889972A US3895172A US 3895172 A US3895172 A US 3895172A US 29889972 A US29889972 A US 29889972A US 3895172 A US3895172 A US 3895172A
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asphalts
asphalt
waterproofing
percent
weight
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Thornton K Jones
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Chevron USA Inc
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Chevron Research and Technology Co
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D195/00—Coating compositions based on bituminous materials, e.g. asphalt, tar, pitch
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31815—Of bituminous or tarry residue

Definitions

  • This invention relates to a method of water-proofing with asphalts displaying increased resistance to deterioration produced by weathering. More specifically, it involves coating construction surfaces, and more particularly roofs, with non-catalyzed oxidized asphalts containing minor amounts of certain polyamines.
  • Asphalt has been used extensively in forming protective coatings for roofs. It is commonly employed in making sheet-or roll-type covering and shingles and is also frequently applied in molten form and spread by brushing or mopping the material evenly over the roof and allowing it to solidify to form a smooth coating. Asphalts are relatively inexpensive and are especially desirable roofing materials, being waterproof, easily applied and providing protection from the elements for relatively long periods of time. While asphaltic materi als are, in general, quite stable to ordinary conditions of weathering, i.e., snow, rain, sleet, and sun, etc., it is important that materials of even greater stability to weathering be provided.
  • U.S. Pat. No. 3,028,249 discloses that the addition of certain amines to asphalts which have been oxidized in the presence of a phosphorous containing catalyst produces a material with a higher softening point without affecting the penetration characteristic of the asphalt. However, it is also disclosed that no apparent effect results from the addition of an amine to a noncatalytically oxidized asphalt.
  • the amine additives of this invention include polyalkylene polyamines, examples of which are ethylene diamine, diethylene tetramine, triethylene tetramine and tetraethylene pentamine.
  • Duomeens Other operable amines are diamines such as the commercially available Duomeen compounds which are aliphatic polyamines marketed by Armour and Company.
  • Examples of the Duomeens are Duomeen C, which is prepared by condensation of a dodecyl amine (coco) with acrylonitrile followed by hydrogenation to the corresponding diamine.
  • the Duomeens possess the formula:
  • R is preferably a C to C aliphatic chain.
  • Duomeen T is a C or octadecyl (tallow) amine of the type described.
  • N-alkyl derivatives of the above enumerated polyalkylene polyamines such as N-dodecyl tetraethylene pentamine, N,N-didodecyl tetraethylene pentamine, etc.
  • the polyamines are employed in the asphalts in minor proportions sufficient to impart weathering resistance. Generally, amounts of from 0.1 to 10 percent by weight are sufficient; amounts of from 0.1 to 5 percent by weight are preferred.
  • the polyamine compounds are prepared by any suitable method.
  • the preparation of these types of compounds is well known in the art and the invention does not lie in the preparation.
  • the polyamine additives may be introduced into the asphalts either prior to the air-blowing or the oxidation step, during this operation or after the oxidized material is obtained.
  • the preferred method is to add the amine to the asphalt prior to the blowing operation; the asphalt is melted during the blowing step and is under extreme agitation and the additives will then disperse easily throughout the material.
  • the amine can be introduced into the previously prepared oxidized asphalts by heating the asphalt until it is molten and stirring the additive into the molten mixture.
  • Asphalts suitable for use in the method of this invention are air-blown asphalts.
  • the blown or oxidized asphalts are particularly suitable for coating applications and generally possess desirable low temperature susceptibility, a higher softening point for a given penetration as compared with unoxidized materials, and moderately high ductility.
  • the non-catalyzed oxidized asphalts should have softening points above F. In general, asphalts with softening points between and 250F. are preferred.
  • the stabilization i.e., increase in resistance to weathering deterioration resulting from the addition of the amines of this invention were determined in an accelerated weathering test.
  • This test was conducted in a Weather-Ometer apparatus, Model DMC, manufactured by the Atlas Electric Devices Company of Chicago, Ill. Briefly, the test involves exposing an asphalt coating on a metal panel to a carbon arc lamp, to a water spray and to cold for intermittent periods.
  • the panels are prepared by the heated platen press method (ASTM D 1669- 97).
  • asphaltic compositions were heated in an oil bath maintained at 500F. until the desired fluidity was obtained, usually at a temperature of from 400 425F.
  • Aluminum panels were masked with tape and heated to 300F.
  • the molten asphalt was poured onto the hot panel, covered with a sheet of Teflon, and pressed by hydraulic press platens which were heated to about 225F.
  • the panels were then removed from the press and allowed to cool to room temperature.
  • the Teflon and masking tape were then removed.
  • the thickness of the asphaltic coating was maintained at 0.025 i 0.001 inch.
  • the panels thus prepared were exposed in the Weather-Ometer within twenty-four hours of preparation.
  • the panels which had been prepared by the abovedescribed method were exposed in Model DMC Weather-Ometers using the ASTM D 529-59T Daily Cycle A, which is otherwise known as the 51-9C cycle.
  • This cycle consists of exposure to single arc light for 51 minutes at 140F. and for 9 minutes to light plus a cold water spray.
  • the spray water was deionized to a maximum solids content of 20 ppm and cooled to 40F. i lF. Exposure was maintained for 22 hours per day, days per week.
  • the line voltage to the Weather- Ometers was maintained at 216 volts by an automatic voltage regulator. Power consumption by the arcs and are control solenoids was held within the range of 1750 to 1850 watts by adjustment of the arc lamp wattage.
  • the panels thus prepared were exposed in sets of 4, 6, and 8 pairs in two or three machines or in sets of 4 in 2 machines.
  • the multiple exposures gave values within about I 0 percent of the true value at the 95 percent confidence level.
  • Panel inspection was made daily by the high voltage spark technique (ASTM D l670-59T). Briefly, this involves applying a high voltage to the aluminum backing of each panel, placing a sheet of photographic paper over the asphaltic surface, and placing an electrode over the paper. Thus, where a crack has developed in the coating, a spark will jump through the paper to the electrode and, upon developing the paper, an impression will remain indicating a point of coating faulure; i.e., a crack. In these tests, spark voltage was held at 7500 volts, and current at 180 microamperes. The spark failure pattern was recorded on Kodak Velite photographic paper and examined under a 60-square transparent grid. In the tests, a panel was considered to have failed when cracks appeared in 30 of the squares.
  • Asphaltic compositions containing the additives of this invention were prepared.
  • the amine additives were added to the crude asphalt residue and the mixtures were blown, without catalyst, to a softening point of 2l5225F. in a conventional manner.
  • the additives were stirred into the molten asphalt which had already been blown, without catalyst, to the prescribed softening point range.
  • EXAMPLE 1 1% by weight of Duomeen T was added to a molten sample of a blown asphalt which had been blown to a softening point of 215 225F. The additive was added after the residua had been air-blown by a conventional technique. This composition is designated as Composition A.
  • EXAMPLE 2 1% by weight of tetraethylene pentamine was added to a portion of the California Coastal residuum described above and this material was blown to a softening point of 215 225F. This material is designated as Composition B.
  • the asphalt is applied in a molten state to the surface to be protected. It may thus be brushed, rolled, sprayed, or otherwise applied, in a convenient thickness and allowed to cool. While the method is particularly applicable to roofs, other parts of building and like construction may be protected in the same manner.
  • the asphalts may contain other materials commonly employed in coating compositions.
  • certain fillers or extenders may be included.
  • the composition may contain from 5 to 60 percent by weight of granular or non-fibrous extenders, such as limestone, flue dust, slate flour, talc, ground silica, aluminum silicate ore, diatomaceous earth, etc., or from 1 to 10 percent by weight of fibrous extenders, for example, asbes' tos, mineral wool, beet sugar residues, corn stalks, bagasse, etc.
  • the asphalt which is applied contains polyamines of the general formula:
  • a and B are selected from the group consisting of hydrogen and hydrocarbon radicals of from 2 to 24 carbon atoms, R is lower alkylene of from 2 to 4 carbon atoms and n is a whole number from 1 to 5.
  • the method of waterproofing a surface which comprises coating said surface with a composition consisting essentially of from -99.9 percent by weight of a molten, non-catalytically oxidized asphalt having a ring and ball softening point in the range of l30F.-250F., and from 01-10 percent by weight of a polyamine of the general formula:
  • a and B are selected from the group consist- 6 ing of hydrogen and hydrocarbon radicals to from 2 to 5.
  • A is hydrogen
  • Carbon is an alkyl group of from 10 to 24 carbon atoms
  • R is atomsan nisawoenum ero mm to.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Working-Up Tar And Pitch (AREA)
  • Paints Or Removers (AREA)

Abstract

Method of waterproofing a surface which comprises coating said surface with a non-catalyzed oxidized asphalt composition having a ring and ball softening point in the range of 130* to 250*F., said asphalt containing from 0.1 to 10 percent by weight of a polyamine of the general formula:

Description

United States Patent [1 1 Jones METHOD OF WATERPROOFING WITH ASPHALTS CONTAINING POLYAMINES [75] Inventor: Thornton K. Jones, Greenbrae,
Calif.
[73] Assignee: Chevron Research Company, San Francisco, Calif.
[22] Filed: Oct. 19, 1972 [21] Appl. No.: 298,899
Related US. Application Data [63] Continuation of Ser. No. 723,297, April 22, 1968, abandoned, which is a continuation-in-part of Ser. No. 354,792, March 25, 1974, abandoned.
[52] US. Cl. 428/489; 106/2; 106/273 N; 106/277 [51] Int. Cl C09d 3/46 [58] Field of Search 106/2, 273 N, 277; 117/168 [56] References Cited UNITED STATES PATENTS 2,716,616 8/1955 Rendall et al 106/273 [451 July 15,1975
2,797,169 6/1957 Mcrtens 106/273 2,886,458 5/1959 Ceintreg... 106/277 3,028,249 4/1962 Hoiberg.... 106/273 Primary ExaminerMichael R. Lusignan Attorney, Agent, or Firm-G. F. Magdeburger; C. J. Tonkin; B. G. Fehringer ABSTRACT in which A and B are selected from the group consisting of hydrogen and hydrocarbon radicals of from 2 to 24 carbon atoms, R is lower alkylene of 2 to 4 carbon atoms and n is a whole number from 1 to 5.
7 Claims, No Drawings METHOD OF WATERPROOFING WITH ASPHALTS CONTAINING POLYAMINES CROSS REFERENCE TO RELATED APPLICATIONS This application is a continuation of copending application Ser. No. 723,297, filed Apr. 22, 1968, now abandoned, which in turn was a continuation-in-part of copending application Ser. No. 354,792 filed Mar. 25,
1964, now abandoned.
BACKGROUND OF THE INVENTION This invention relates to a method of water-proofing with asphalts displaying increased resistance to deterioration produced by weathering. More specifically, it involves coating construction surfaces, and more particularly roofs, with non-catalyzed oxidized asphalts containing minor amounts of certain polyamines.
Asphalt has been used extensively in forming protective coatings for roofs. It is commonly employed in making sheet-or roll-type covering and shingles and is also frequently applied in molten form and spread by brushing or mopping the material evenly over the roof and allowing it to solidify to form a smooth coating. Asphalts are relatively inexpensive and are especially desirable roofing materials, being waterproof, easily applied and providing protection from the elements for relatively long periods of time. While asphaltic materi als are, in general, quite stable to ordinary conditions of weathering, i.e., snow, rain, sleet, and sun, etc., it is important that materials of even greater stability to weathering be provided.
The manifestations of weathering deterioration in asphaltic coatings include the changes in appearance and coloration, wrinkling, cracks and pin holes, etc. Commonly, small cracks or checks" appear in the coating and these cracks eventually widen to produce a condition described as alligatoring. The appearance of these cracks, of course, diminishes the water-proof characteristics ofa roof and the delaying of such deterioration is a highly desirable object in the coating and roofing art. A number of agents which have been employed in the past have been somewhat successful in extending the weathering life of asphaltic compositions in certain aspects, however, as far as is known, prior to the present invention, no compositions have as yet been developed that successfully extend weathering lives of asphaltic coatings for extended periods.
U.S. Pat. No. 3,028,249 discloses that the addition of certain amines to asphalts which have been oxidized in the presence of a phosphorous containing catalyst produces a material with a higher softening point without affecting the penetration characteristic of the asphalt. However, it is also disclosed that no apparent effect results from the addition of an amine to a noncatalytically oxidized asphalt.
SUMMARY It has now been found that surfaces can be given substantially increased protection from weathering by applying to the surface as a water-proofing agent, a molten, non-catalytically oxidized asphalt containing minor amounts of certain polyamines. The method is particularly applicable to the protection of roofs.
DESCRIPTION The amine additives of this invention include polyalkylene polyamines, examples of which are ethylene diamine, diethylene tetramine, triethylene tetramine and tetraethylene pentamine.
Other operable amines are diamines such as the commercially available Duomeen compounds which are aliphatic polyamines marketed by Armour and Company. Examples of the Duomeens are Duomeen C, which is prepared by condensation of a dodecyl amine (coco) with acrylonitrile followed by hydrogenation to the corresponding diamine. Thus, the Duomeens possess the formula:
in which R is preferably a C to C aliphatic chain. Duomeen T is a C or octadecyl (tallow) amine of the type described.
Also included are the N-alkyl derivatives of the above enumerated polyalkylene polyamines, such as N-dodecyl tetraethylene pentamine, N,N-didodecyl tetraethylene pentamine, etc.
In the method of this invention, the polyamines are employed in the asphalts in minor proportions sufficient to impart weathering resistance. Generally, amounts of from 0.1 to 10 percent by weight are sufficient; amounts of from 0.1 to 5 percent by weight are preferred.
The polyamine compounds are prepared by any suitable method. The preparation of these types of compounds is well known in the art and the invention does not lie in the preparation.
The polyamine additives may be introduced into the asphalts either prior to the air-blowing or the oxidation step, during this operation or after the oxidized material is obtained. The preferred method is to add the amine to the asphalt prior to the blowing operation; the asphalt is melted during the blowing step and is under extreme agitation and the additives will then disperse easily throughout the material. Though somewhat less effective in reducing weather-caused deterioration, the amine can be introduced into the previously prepared oxidized asphalts by heating the asphalt until it is molten and stirring the additive into the molten mixture.
Asphalts suitable for use in the method of this invention are air-blown asphalts. The blown or oxidized asphalts are particularly suitable for coating applications and generally possess desirable low temperature susceptibility, a higher softening point for a given penetration as compared with unoxidized materials, and moderately high ductility. In addition, they possess a high stability and resistance to flow, a characteristic particularly important when coatings are to be applied to surfaces which are other than horizontal.
The non-catalyzed oxidized asphalts should have softening points above F. In general, asphalts with softening points between and 250F. are preferred.
The stabilization, i.e., increase in resistance to weathering deterioration resulting from the addition of the amines of this invention were determined in an accelerated weathering test. This test was conducted in a Weather-Ometer apparatus, Model DMC, manufactured by the Atlas Electric Devices Company of Chicago, Ill. Briefly, the test involves exposing an asphalt coating on a metal panel to a carbon arc lamp, to a water spray and to cold for intermittent periods.
More specifically, the panels are prepared by the heated platen press method (ASTM D 1669- 97). The
asphaltic compositions were heated in an oil bath maintained at 500F. until the desired fluidity was obtained, usually at a temperature of from 400 425F. Aluminum panels were masked with tape and heated to 300F. The molten asphalt was poured onto the hot panel, covered with a sheet of Teflon, and pressed by hydraulic press platens which were heated to about 225F. The panels were then removed from the press and allowed to cool to room temperature. The Teflon and masking tape were then removed. The thickness of the asphaltic coating was maintained at 0.025 i 0.001 inch. The panels thus prepared were exposed in the Weather-Ometer within twenty-four hours of preparation.
The panels which had been prepared by the abovedescribed method were exposed in Model DMC Weather-Ometers using the ASTM D 529-59T Daily Cycle A, which is otherwise known as the 51-9C cycle. This cycle consists of exposure to single arc light for 51 minutes at 140F. and for 9 minutes to light plus a cold water spray. The spray water was deionized to a maximum solids content of 20 ppm and cooled to 40F. i lF. Exposure was maintained for 22 hours per day, days per week. The line voltage to the Weather- Ometers was maintained at 216 volts by an automatic voltage regulator. Power consumption by the arcs and are control solenoids was held within the range of 1750 to 1850 watts by adjustment of the arc lamp wattage.
The panels thus prepared were exposed in sets of 4, 6, and 8 pairs in two or three machines or in sets of 4 in 2 machines. The multiple exposures gave values within about I 0 percent of the true value at the 95 percent confidence level.
Panel inspection was made daily by the high voltage spark technique (ASTM D l670-59T). Briefly, this involves applying a high voltage to the aluminum backing of each panel, placing a sheet of photographic paper over the asphaltic surface, and placing an electrode over the paper. Thus, where a crack has developed in the coating, a spark will jump through the paper to the electrode and, upon developing the paper, an impression will remain indicating a point of coating faulure; i.e., a crack. In these tests, spark voltage was held at 7500 volts, and current at 180 microamperes. The spark failure pattern was recorded on Kodak Velite photographic paper and examined under a 60-square transparent grid. In the tests, a panel was considered to have failed when cracks appeared in 30 of the squares.
Asphaltic compositions containing the additives of this invention were prepared. In some cases, the amine additives were added to the crude asphalt residue and the mixtures were blown, without catalyst, to a softening point of 2l5225F. in a conventional manner. In the other examples, the additives were stirred into the molten asphalt which had already been blown, without catalyst, to the prescribed softening point range.
The asphaltic compositions derived from a California Coastal residuum having a penetration of 65 at 77F.
The following examples illustrate the preparation of composition of this invention.
EXAMPLE 1 1% by weight of Duomeen T was added to a molten sample of a blown asphalt which had been blown to a softening point of 215 225F. The additive was added after the residua had been air-blown by a conventional technique. This composition is designated as Composition A.
EXAMPLE 2 1% by weight of tetraethylene pentamine was added to a portion of the California Coastal residuum described above and this material was blown to a softening point of 215 225F. This material is designated as Composition B.
The following table shows the results of accelerated weathering tests performed on compositions of Examples l and 2. The tests were run by the above described method.
TABLE I Weather-Ometer Composition Softening Point Life Days 2 l 5 4 l A 66 B 62 These data indicate that the polyamine additives of this invention significantly improve the weathering characteristics of the non-catalytically oxidized asphalts. The method of this invention thus provides protection from water damage for roofs of up to 50% greater periods than when coating with an asphalt with no additive. This can be translated into 5 or more additional years of service for the roof.
The asphalt is applied in a molten state to the surface to be protected. It may thus be brushed, rolled, sprayed, or otherwise applied, in a convenient thickness and allowed to cool. While the method is particularly applicable to roofs, other parts of building and like construction may be protected in the same manner.
In addition to the weathering life additives, the asphalts may contain other materials commonly employed in coating compositions. Thus, certain fillers or extenders may be included. For example, the composition may contain from 5 to 60 percent by weight of granular or non-fibrous extenders, such as limestone, flue dust, slate flour, talc, ground silica, aluminum silicate ore, diatomaceous earth, etc., or from 1 to 10 percent by weight of fibrous extenders, for example, asbes' tos, mineral wool, beet sugar residues, corn stalks, bagasse, etc.
In the preferred method of the invention the asphalt which is applied contains polyamines of the general formula:
in which A and B are selected from the group consisting of hydrogen and hydrocarbon radicals of from 2 to 24 carbon atoms, R is lower alkylene of from 2 to 4 carbon atoms and n is a whole number from 1 to 5.
I I claim:
1. The method of waterproofing a surface which comprises coating said surface with a composition consisting essentially of from -99.9 percent by weight of a molten, non-catalytically oxidized asphalt having a ring and ball softening point in the range of l30F.-250F., and from 01-10 percent by weight of a polyamine of the general formula:
in which A and B are selected from the group consist- 6 ing of hydrogen and hydrocarbon radicals to from 2 to 5. The method of claim 1 in which A is hydrogen, B 24 atcfmsq :1 y g tl of to 2' Carbon is an alkyl group of from 10 to 24 carbon atoms, R is atomsan nisawoenum ero mm to.
t th I d l. 2. The method of claim 1 wherein A and B are hydroy ene an n 6. The method of claim 5 in which E is dodecyl.
7. The method of claim 5 in which E is octadecyl.
gen and R is ethylene. 5
3. The method of claim 2 in which n is 2. 4. The method of claim 2 in which n is 4.

Claims (7)

1. THE METHOD OF WATERPROOFING A SURFACE WHICH COMPRISES CATING SAID SURFACE WITH A COMPOSITION CONSISTING ESSENTIALLY OF FROM 90-99.9 PERCENT BY WEIGHT OF A MOLTEN, NON-CATALYTICALLY OXIDIZED ASPHALT HAVING A RING AND BALL SOFTENING POINT IN THE RANGE OF 130*F, AND FROM 0.0-10 PERCENT BY WEIGHT OF A POLYAMINE OF THE GENERAL FORMULA:
2. The method of claim 1 wherein A and B are hydrogen and R is ethylene.
3. The method of claim 2 in which n is 2.
4. The method of claim 2 in which n is 4.
5. The method of claim 1 in which A is hydrogen, B is an alkyl group of from 10 to 24 carbon atoms, R is trimethylene, and n is
6. The method of claim 5 in which B is dodecyl.
7. The method of claim 5 in which B is octadecyl.
US29889972 1968-04-22 1972-10-19 Method of waterproofing with asphalts containing polyamines Expired - Lifetime US3895172A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997354A (en) * 1974-01-31 1976-12-14 Pierrefitte-Auby Bituminous binder compositions
US4561900A (en) * 1980-12-23 1985-12-31 Ceca S.A. Use of novel amines as bases for the preparation of emulsions of hydrocarbon binders
US4786329A (en) * 1987-09-09 1988-11-22 The Dow Chemical Company Asphalt compositions containing anti-stripping additives prepared from amines or polyamines and phosphonates
US5362314A (en) * 1992-06-15 1994-11-08 Exxon Chemical Patents, Inc. Additive modified bituminous emulsions
WO1996034058A1 (en) * 1995-04-28 1996-10-31 Shell Internationale Research Maatschappij B.V. Asphalt composition
US5961730A (en) * 1997-10-30 1999-10-05 Morton International, Inc. Method of asphalt removal from surfaces
US20100022688A1 (en) * 2008-07-23 2010-01-28 Baker Hughes Incorporated Process for improving the transfer properties of bitumen

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2716616A (en) * 1949-05-23 1955-08-30 Minnesota Mining & Mfg Treated bituminous and aggregate compositions
US2797169A (en) * 1953-05-11 1957-06-25 California Research Corp Non-dusting asphaltic coatings
US2886458A (en) * 1956-05-25 1959-05-12 Routiere De La Gironde Soc Chi Binder for coating surfacing materials and applications thereof
US3028249A (en) * 1962-04-03 Asphaltic compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028249A (en) * 1962-04-03 Asphaltic compositions
US2716616A (en) * 1949-05-23 1955-08-30 Minnesota Mining & Mfg Treated bituminous and aggregate compositions
US2797169A (en) * 1953-05-11 1957-06-25 California Research Corp Non-dusting asphaltic coatings
US2886458A (en) * 1956-05-25 1959-05-12 Routiere De La Gironde Soc Chi Binder for coating surfacing materials and applications thereof

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997354A (en) * 1974-01-31 1976-12-14 Pierrefitte-Auby Bituminous binder compositions
US4561900A (en) * 1980-12-23 1985-12-31 Ceca S.A. Use of novel amines as bases for the preparation of emulsions of hydrocarbon binders
US4786329A (en) * 1987-09-09 1988-11-22 The Dow Chemical Company Asphalt compositions containing anti-stripping additives prepared from amines or polyamines and phosphonates
US5362314A (en) * 1992-06-15 1994-11-08 Exxon Chemical Patents, Inc. Additive modified bituminous emulsions
WO1996034058A1 (en) * 1995-04-28 1996-10-31 Shell Internationale Research Maatschappij B.V. Asphalt composition
US5961730A (en) * 1997-10-30 1999-10-05 Morton International, Inc. Method of asphalt removal from surfaces
US20100022688A1 (en) * 2008-07-23 2010-01-28 Baker Hughes Incorporated Process for improving the transfer properties of bitumen
US9034093B2 (en) * 2008-07-23 2015-05-19 Baker Hughes Incorporated Process for improving the transfer properties of bitumen

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