CA1201554A - Process for producing organosilane-containing asphalt masses - Google Patents
Process for producing organosilane-containing asphalt massesInfo
- Publication number
- CA1201554A CA1201554A CA000437441A CA437441A CA1201554A CA 1201554 A CA1201554 A CA 1201554A CA 000437441 A CA000437441 A CA 000437441A CA 437441 A CA437441 A CA 437441A CA 1201554 A CA1201554 A CA 1201554A
- Authority
- CA
- Canada
- Prior art keywords
- organosilane
- process according
- mixture
- atoms
- finely divided
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Civil Engineering (AREA)
- Engineering & Computer Science (AREA)
- Structural Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Road Paving Structures (AREA)
- Working-Up Tar And Pitch (AREA)
- Silicon Polymers (AREA)
- Fittings On The Vehicle Exterior For Carrying Loads, And Devices For Holding Or Mounting Articles (AREA)
- Special Wing (AREA)
- Window Of Vehicle (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Road Paving Machines (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
The present invention provides a process for producing organosilane-containing asphalt compositions in which a finely divided mixture consisting of at least one organosilane and at least one finely divided inorganic solid is mixed with mineral components and this mixture is subsequently mixed with hot liquid bitumen.
The present invention provides a process for producing organosilane-containing asphalt compositions in which a finely divided mixture consisting of at least one organosilane and at least one finely divided inorganic solid is mixed with mineral components and this mixture is subsequently mixed with hot liquid bitumen.
Description
~tJ~
The present invention xelates to a process fox prodllcing org~nosi~lane-containing ~sphalt compositions which are suttable, for example, as a road surface.
Organosilane-containing asphalt compositions are disclosed in various patents. Ger~an Offenlegungsschrift 3,028,365 discloses bitu~inous binders containing at least one organosilane. They are produced by stirring the organo-silane into the ~itumen, pre~iously heated to a temperature of 120 to 230C and thus liquefied. In U.S. Patent 4,036,661 organosilane conta~n;ng asphalt co~positions are disclosed in which the silane also is first added to the molten bitumen, which is subsequently mixed with mineral components to form an asphalt suita~le as a road cover.
From U.~. Patent 4,03~,661, it is also disclosed that the mineral components can ~e treated with the solution of an organosilane prior to ~eing mixed with bitumen. Because of the burden on the environment and the increased fire hazard which can ~e caused ~y the solvents this process variant is discussed only theoretically. The purpose of adding organo-silane is to increase the adhesion between the bitumen andthe ~ineral components of the asphalt.
Howe~er, the conventional processes have the disadyantage that the organosilane must be added to the hot bitumen. This results in a long thermal stress of the si-lanes which, depending on the properties of the material, can result ~n los~ ~f ~ater~l and pollution of the environ-~ent due to eyapoxation and decomposition of the silanes.
The present invention pxovides ~ proce$s ~or produc~ng org~nos~lane~conta~ning asphalt co~positions which does not haYe tfiese di~adYa~nta~es.
- Accoxdi~ng t~ the pre5ent inYention there is pxo ~ided a process for producing org~nosilane-conta; n; ng asphalt - 1 - ~X~
5~
compositionS in which at least one oxganosilane in the form oE a finely divided mixture consis-ting of a-t least one organo-silane and at least one finely divided inorganic solid filler is mixed with mineral aggregate and -thls mixture is subsequent-ly mixed with liquid bitumen in a conventional manner.
The mineral ag~regate consist of materials divided according to screening in-to fine gravel (2 to 32 mm granulation), crushed sand (0.09 to 2 mml and filler ( ~0.09 mm), are mixed with the bitumen for the production of asphalt surfaces according to the technical standards of building authorities.
In a suitable embodiment of the filler which is sprinkled or wetted in some other suitable manner with at least one organosilane for t~e production of the organosilane-containing mixture can be used as the finely divided inorganic solid.
The total amount or only a portion of the filler required for producing the asphalt surface can be trea-ted with the organosilane.
The mixing of a powdered organosilane/carbon black mixture containing 30 to 60~ by weight, preferably 47 to 53%
by weight of at least one organosilane relative to the total amount is particularly suitable for the production of asphalt compositions. This type of mixture can be prepared analogous-ly to the process described in the German Patent No. 2,747,277 The organosilane/carbon black mixture can selectively be mixed first with one component, pxeferably the filler, or eVen irnmediately with thetotal amount of m~neral substance.
The amount o~ the o~ganosilane/carbon black mi~ture is always such that the concentration o~ the organo-silane, relatiYe to the asphalt IS between 0.005 and 0.09 by ~7eight.
Powdered m~xtures containing one or several
The present invention xelates to a process fox prodllcing org~nosi~lane-containing ~sphalt compositions which are suttable, for example, as a road surface.
Organosilane-containing asphalt compositions are disclosed in various patents. Ger~an Offenlegungsschrift 3,028,365 discloses bitu~inous binders containing at least one organosilane. They are produced by stirring the organo-silane into the ~itumen, pre~iously heated to a temperature of 120 to 230C and thus liquefied. In U.S. Patent 4,036,661 organosilane conta~n;ng asphalt co~positions are disclosed in which the silane also is first added to the molten bitumen, which is subsequently mixed with mineral components to form an asphalt suita~le as a road cover.
From U.~. Patent 4,03~,661, it is also disclosed that the mineral components can ~e treated with the solution of an organosilane prior to ~eing mixed with bitumen. Because of the burden on the environment and the increased fire hazard which can ~e caused ~y the solvents this process variant is discussed only theoretically. The purpose of adding organo-silane is to increase the adhesion between the bitumen andthe ~ineral components of the asphalt.
Howe~er, the conventional processes have the disadyantage that the organosilane must be added to the hot bitumen. This results in a long thermal stress of the si-lanes which, depending on the properties of the material, can result ~n los~ ~f ~ater~l and pollution of the environ-~ent due to eyapoxation and decomposition of the silanes.
The present invention pxovides ~ proce$s ~or produc~ng org~nos~lane~conta~ning asphalt co~positions which does not haYe tfiese di~adYa~nta~es.
- Accoxdi~ng t~ the pre5ent inYention there is pxo ~ided a process for producing org~nosilane-conta; n; ng asphalt - 1 - ~X~
5~
compositionS in which at least one oxganosilane in the form oE a finely divided mixture consis-ting of a-t least one organo-silane and at least one finely divided inorganic solid filler is mixed with mineral aggregate and -thls mixture is subsequent-ly mixed with liquid bitumen in a conventional manner.
The mineral ag~regate consist of materials divided according to screening in-to fine gravel (2 to 32 mm granulation), crushed sand (0.09 to 2 mml and filler ( ~0.09 mm), are mixed with the bitumen for the production of asphalt surfaces according to the technical standards of building authorities.
In a suitable embodiment of the filler which is sprinkled or wetted in some other suitable manner with at least one organosilane for t~e production of the organosilane-containing mixture can be used as the finely divided inorganic solid.
The total amount or only a portion of the filler required for producing the asphalt surface can be trea-ted with the organosilane.
The mixing of a powdered organosilane/carbon black mixture containing 30 to 60~ by weight, preferably 47 to 53%
by weight of at least one organosilane relative to the total amount is particularly suitable for the production of asphalt compositions. This type of mixture can be prepared analogous-ly to the process described in the German Patent No. 2,747,277 The organosilane/carbon black mixture can selectively be mixed first with one component, pxeferably the filler, or eVen irnmediately with thetotal amount of m~neral substance.
The amount o~ the o~ganosilane/carbon black mi~ture is always such that the concentration o~ the organo-silane, relatiYe to the asphalt IS between 0.005 and 0.09 by ~7eight.
Powdered m~xtures containing one or several
2 -
3 ~
silanes hayin~ the formula ~ I~ CZ-Alkm~5nH~2-ml are particularl~ suitable.
In this fo.rmula (I~
~ 2 z = - Si - ~ t - Si _ ~2, _ Si _ ~2 2 ~.2 _2 with Rl being alkyl containing 1 to 4 Catoms, R2 ~eing alkoxy containing 1 to 4C atoms, ~lk being divalent saturated ali-phatic hydrocarbon containing 1 to 4C atoms, m being 1 or 2,and n being 1 to 6 when m = 2.
Among these silanes the following compounds are preferably used:
bis-(3-[triethoxy-silyl]-propyl)-disulphane, -sulphane, or -tetrasulphane.
Powdered concentrates cont~'n;ng one or several silanes having the formula ~ (NH2~a-R -~2-a))a-~iR4-P
are particularly suitable for the purposes according to the present invention. In this formula (II) R is alkyl cont~in;ng 1 to 4 C atcm~4 R3 = trivalent saturated aliphatic hydrocarbon cont~; n ing 1 to 4 Catoms, m = 1 or 2, and n-1 or 2.
The organosilane-cont~;n;ng asphalt composition can be used for producing so called asphalt for road construc-tion and also for producing special surfaces as for example for bridges, depending of the type and quantity of the mineral mixture. The~ can also be used for producing mastic asphal~
for road construction ox building construction ox for pxoduc-ing xoof.~n~ mate~ial, roo~ sections, undercoating protectionfor veh~cles as fox cable ~aterial.
Because of the incorporation of the organo-.
~2~
~ilaneC~ into the ~ineral su~stance, ~hich is suhsequently mixed ~ith the hot Bitumen, there xesults a substantial reduction of the thermal stress of the processed silanes as compaxe~ with the prio~ axt. Furthermore the evaporation losses are ~n~mal since an organosilane adsorbed to an in-organic solid does not evaporate as easily as a liquid silane stir~ed into the hot bitumen. The lower thermal stress also permits the economic use of organosilanes which, according to the process of the prior art, could be used in bitumen only with high losses of substances.
Surprisingly it has been found that the effect of mixtures of organosilane and inorganic solid used accord-ing to the present invention improves distinctly. It has also heen found that, for example, in order to attain identical splitting tensile strength there is required according to the present invention only one half the amount of organosilane which must be incorporated into the hot bitumen according to the prior art.
The following Examples ~ill serve to illustrate the present invention:
An asphalt concrete 0/11 rich in fine gravel is produced. Its content of binder is so chosen that a void content in the order of 7% by volume on the Marshall specimen is obtained. When using a 5.4% by ~eight road-construction bitume~ 80 the follo~ing kind of dosing for asphalt concrete 0/11 rich in fine gravel is obtained:
Crushed sand and fine gravel having a particle size Qf up to 5 ~m consist of qua~tzitic ~xay~ack~ from the Osnabruck ~eg~on. ~s a ver~ acid rock type it causes problems in the ~dhesion o~ the bindex film to the rock surface.
-- 4 ~
5,~
Dosin~ Resulting C~ h~ welghtl (~ b~ weightl binder content 5.4 5.4 binder type B8Q B80 filler 7.Q filler 7.8 limestone powder Hehl.en ~ ~ Q.09 quartzite crushed sand 0.09/0.25 8.3 ~ 0.09 1.5 0.25/0.71 14.0 0.09 - 0.25 7.6 0.71/2 20.0 0.25 - 0.71 14.0 2/5 22.0 .71 - 2 20.0 5/8 13.9 8/11 14.0 quartzite fine gravel 2 - 5 22.0 5 - 8 13.9 8 - 11 14.0 With the characterized composition Marshall spe-cimens whose void content is to be in the ordex of 7% by volume according to the conditions are produced. The splitting tensile strength is determined on the Marshall specimens.
When stored in water an unfavourable affinity between rock surface and bitumen ~ecome evident in that a water film slides between binder skin and rock surface, that it reduces the splitting tensile strength and it becomes noticeable to some extent by the increased volume of the specimens.
The splitting tensile test was carried out on a universal press of the test class I with a constant feed rate of 50 mm per minute at a test temperature of 25C. The splitting tensile strength is o~tained from the numerical value equation:
~ Z .d.h wherein P represents the ma~t~l compressive force in N, d ~epxe~ents the d~a~eter o~ the s~ecimen in m~ and h repre-se~ts the he~ght of the specimen: in m~.
r3 ~5 The test ~esults are listed in the followin~
Table 1 which contains the type o~ adhesive, the dosing rela-tive to the ~inder content ~n % ~ weight and the type of addition in variation o~ an addition to the bitumen or to the mineral substance mixture Bis-(3-ethoxy-silyl-propyl)tetra-sulphane (Si69) or a commercial powdery mixtur~ consisting of 50% by wei~ht of Si69 and 50% ~y weight of carbon black is used as silane, i.e. that 0.5% by weight X 50S correspond to an Si69 proportion of 0.25% by weight.
Test 1 serves as a comparison test without the use of a silane.
Table 1 Test No. 1 2 3 4 adhesive - Si69 Si69 X 50S
dosing - 0.25 0.5 0.5 addition to - bitumenbitumen mineral sub-stance mixture ~sz(N/mm ~
without stress 0.86 0.86 0.86 0.86 after storage in water 48h 0.45 0.68 0.68 0.81 192h 0.30 0.63 0.64 0.71 768h 0.18 0.59 0.66 0.6S
decrease Bsz (%)48h -47.7 -20.9 -20.9 -5.8 192h -66.1 -26.7 -25.6 -17.4 768h -79.1 -31.4 -23.3 -24.0 It is evident that the asphalt composition having 0.5~ by weight X 50S in the mineral substance mixture shows almost the same decrease of the splitting tensile value as that in whXch 0.5% by weight of Si69 were mixed directly with the hot bltu~en.
silanes hayin~ the formula ~ I~ CZ-Alkm~5nH~2-ml are particularl~ suitable.
In this fo.rmula (I~
~ 2 z = - Si - ~ t - Si _ ~2, _ Si _ ~2 2 ~.2 _2 with Rl being alkyl containing 1 to 4 Catoms, R2 ~eing alkoxy containing 1 to 4C atoms, ~lk being divalent saturated ali-phatic hydrocarbon containing 1 to 4C atoms, m being 1 or 2,and n being 1 to 6 when m = 2.
Among these silanes the following compounds are preferably used:
bis-(3-[triethoxy-silyl]-propyl)-disulphane, -sulphane, or -tetrasulphane.
Powdered concentrates cont~'n;ng one or several silanes having the formula ~ (NH2~a-R -~2-a))a-~iR4-P
are particularly suitable for the purposes according to the present invention. In this formula (II) R is alkyl cont~in;ng 1 to 4 C atcm~4 R3 = trivalent saturated aliphatic hydrocarbon cont~; n ing 1 to 4 Catoms, m = 1 or 2, and n-1 or 2.
The organosilane-cont~;n;ng asphalt composition can be used for producing so called asphalt for road construc-tion and also for producing special surfaces as for example for bridges, depending of the type and quantity of the mineral mixture. The~ can also be used for producing mastic asphal~
for road construction ox building construction ox for pxoduc-ing xoof.~n~ mate~ial, roo~ sections, undercoating protectionfor veh~cles as fox cable ~aterial.
Because of the incorporation of the organo-.
~2~
~ilaneC~ into the ~ineral su~stance, ~hich is suhsequently mixed ~ith the hot Bitumen, there xesults a substantial reduction of the thermal stress of the processed silanes as compaxe~ with the prio~ axt. Furthermore the evaporation losses are ~n~mal since an organosilane adsorbed to an in-organic solid does not evaporate as easily as a liquid silane stir~ed into the hot bitumen. The lower thermal stress also permits the economic use of organosilanes which, according to the process of the prior art, could be used in bitumen only with high losses of substances.
Surprisingly it has been found that the effect of mixtures of organosilane and inorganic solid used accord-ing to the present invention improves distinctly. It has also heen found that, for example, in order to attain identical splitting tensile strength there is required according to the present invention only one half the amount of organosilane which must be incorporated into the hot bitumen according to the prior art.
The following Examples ~ill serve to illustrate the present invention:
An asphalt concrete 0/11 rich in fine gravel is produced. Its content of binder is so chosen that a void content in the order of 7% by volume on the Marshall specimen is obtained. When using a 5.4% by ~eight road-construction bitume~ 80 the follo~ing kind of dosing for asphalt concrete 0/11 rich in fine gravel is obtained:
Crushed sand and fine gravel having a particle size Qf up to 5 ~m consist of qua~tzitic ~xay~ack~ from the Osnabruck ~eg~on. ~s a ver~ acid rock type it causes problems in the ~dhesion o~ the bindex film to the rock surface.
-- 4 ~
5,~
Dosin~ Resulting C~ h~ welghtl (~ b~ weightl binder content 5.4 5.4 binder type B8Q B80 filler 7.Q filler 7.8 limestone powder Hehl.en ~ ~ Q.09 quartzite crushed sand 0.09/0.25 8.3 ~ 0.09 1.5 0.25/0.71 14.0 0.09 - 0.25 7.6 0.71/2 20.0 0.25 - 0.71 14.0 2/5 22.0 .71 - 2 20.0 5/8 13.9 8/11 14.0 quartzite fine gravel 2 - 5 22.0 5 - 8 13.9 8 - 11 14.0 With the characterized composition Marshall spe-cimens whose void content is to be in the ordex of 7% by volume according to the conditions are produced. The splitting tensile strength is determined on the Marshall specimens.
When stored in water an unfavourable affinity between rock surface and bitumen ~ecome evident in that a water film slides between binder skin and rock surface, that it reduces the splitting tensile strength and it becomes noticeable to some extent by the increased volume of the specimens.
The splitting tensile test was carried out on a universal press of the test class I with a constant feed rate of 50 mm per minute at a test temperature of 25C. The splitting tensile strength is o~tained from the numerical value equation:
~ Z .d.h wherein P represents the ma~t~l compressive force in N, d ~epxe~ents the d~a~eter o~ the s~ecimen in m~ and h repre-se~ts the he~ght of the specimen: in m~.
r3 ~5 The test ~esults are listed in the followin~
Table 1 which contains the type o~ adhesive, the dosing rela-tive to the ~inder content ~n % ~ weight and the type of addition in variation o~ an addition to the bitumen or to the mineral substance mixture Bis-(3-ethoxy-silyl-propyl)tetra-sulphane (Si69) or a commercial powdery mixtur~ consisting of 50% by wei~ht of Si69 and 50% ~y weight of carbon black is used as silane, i.e. that 0.5% by weight X 50S correspond to an Si69 proportion of 0.25% by weight.
Test 1 serves as a comparison test without the use of a silane.
Table 1 Test No. 1 2 3 4 adhesive - Si69 Si69 X 50S
dosing - 0.25 0.5 0.5 addition to - bitumenbitumen mineral sub-stance mixture ~sz(N/mm ~
without stress 0.86 0.86 0.86 0.86 after storage in water 48h 0.45 0.68 0.68 0.81 192h 0.30 0.63 0.64 0.71 768h 0.18 0.59 0.66 0.6S
decrease Bsz (%)48h -47.7 -20.9 -20.9 -5.8 192h -66.1 -26.7 -25.6 -17.4 768h -79.1 -31.4 -23.3 -24.0 It is evident that the asphalt composition having 0.5~ by weight X 50S in the mineral substance mixture shows almost the same decrease of the splitting tensile value as that in whXch 0.5% by weight of Si69 were mixed directly with the hot bltu~en.
Claims (7)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for producing an organosilane-containing asphalt composition in which at least one organosilane in the form of a finely divided mixture of at least one organosilane and at least one finely divided inorganic solid filler is mixed with mineral aggregate and the mixture is subsequently mixed with liquid bitumen, the concentration of the organo-silane, relative to the asphalt, being between 0.005 and 0.09% by weight.
2. A process according to claim 1, in which a filler having a particle size of up to 0.09 mm is used as the inorganic filler.
3. A process according to claim 1, in which a mix-ture of 30 to 60% by weight of at least one organosilane and 70 to 40% by weight of carbon black is used.
4. A process according to claim 1, 2 or 3, in which a finely divided mixture containing at least one organosilane having the formula (I) wherein with R1 being alkyl containing 1 to 4 C atoms, R2 being alkoxy containing 1 to 4 C atoms, Alk being divalent saturated aliphatic hydrocarbon containing 1 to 4 C atoms, m being 1 or 2, and n being 1 to 6 when m is 2, is used.
5. A process according to claim 1, 2 or 3, in which a finely divided mixture containing at least one organosilane having the formula (II) ((NH2)a-R3-H(2-a))p-SioR1 4-p wherein R1 is alkyl containing 1 to 4 C atoms, R3 is a trivalent saturated aliphatic hydrocarbon radical containing 1 to 4 C atoms, a is 1 or 2, and p is 1 or 2, is used.
6. A process according to claim 1, 2 or 3, in which the organosilane is selected from bis-(3-[triethoxy-silyl]-propyl-sulphane, disulphane, and tetrasulphane.
7. A process according to claim 3, in which the organo-silane is used in an amount of 47-53% by weight of the mixture.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3236381A DE3236381C2 (en) | 1982-10-01 | 1982-10-01 | Process for the production of organosilane-containing asphalt compounds |
| DEP3236381.8 | 1982-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1201554A true CA1201554A (en) | 1986-03-11 |
Family
ID=6174680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000437441A Expired CA1201554A (en) | 1982-10-01 | 1983-09-23 | Process for producing organosilane-containing asphalt masses |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0105133B1 (en) |
| JP (1) | JPS5966456A (en) |
| AT (1) | ATE30434T1 (en) |
| CA (1) | CA1201554A (en) |
| DE (2) | DE3236381C2 (en) |
| DK (1) | DK441283A (en) |
| ES (1) | ES8405053A1 (en) |
| FI (1) | FI74719C (en) |
| NO (1) | NO166537C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3516660A1 (en) * | 1985-05-09 | 1986-11-13 | Degussa Ag, 6000 Frankfurt | POWDER-BASED BINDER CONCENTRATE |
| CN102532922B (en) * | 2011-12-15 | 2013-11-06 | 四川维城磁能有限公司 | Synthetic rubber asphalt and preparation method thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2609305A (en) * | 1947-07-24 | 1952-09-02 | Standard Oil Dev Co | Process for preparing asphalt coated aggregate |
| FR2102794A5 (en) * | 1970-08-21 | 1972-04-07 | France Etat | Mineral granulates - treated with a methyltrialkylsilane hydrolysate for road surfaces |
| US4036661A (en) * | 1973-02-12 | 1977-07-19 | Chevron Research Company | Asphalt mineral aggregate compositions containing silanes as adhesion promoters |
| US4173489A (en) * | 1978-04-12 | 1979-11-06 | Texaco Inc. | Asphalt mineral aggregate compositions |
-
1982
- 1982-10-01 DE DE3236381A patent/DE3236381C2/en not_active Expired
-
1983
- 1983-08-06 EP EP83107765A patent/EP0105133B1/en not_active Expired
- 1983-08-06 AT AT83107765T patent/ATE30434T1/en not_active IP Right Cessation
- 1983-08-06 DE DE8383107765T patent/DE3374205D1/en not_active Expired
- 1983-08-15 NO NO832926A patent/NO166537C/en unknown
- 1983-08-22 ES ES525075A patent/ES8405053A1/en not_active Expired
- 1983-08-25 JP JP58154233A patent/JPS5966456A/en active Granted
- 1983-09-01 FI FI833122A patent/FI74719C/en not_active IP Right Cessation
- 1983-09-23 CA CA000437441A patent/CA1201554A/en not_active Expired
- 1983-09-27 DK DK441283A patent/DK441283A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO832926L (en) | 1984-04-02 |
| FI74719C (en) | 1988-03-10 |
| JPS5966456A (en) | 1984-04-14 |
| NO166537B (en) | 1991-04-29 |
| JPS6111975B2 (en) | 1986-04-05 |
| FI74719B (en) | 1987-11-30 |
| DE3374205D1 (en) | 1987-12-03 |
| EP0105133A1 (en) | 1984-04-11 |
| DK441283A (en) | 1984-04-02 |
| DE3236381A1 (en) | 1984-04-05 |
| NO166537C (en) | 1991-08-07 |
| FI833122A0 (en) | 1983-09-01 |
| DK441283D0 (en) | 1983-09-27 |
| DE3236381C2 (en) | 1986-11-06 |
| EP0105133B1 (en) | 1987-10-28 |
| ATE30434T1 (en) | 1987-11-15 |
| FI833122A (en) | 1984-04-02 |
| ES525075A0 (en) | 1984-05-16 |
| ES8405053A1 (en) | 1984-05-16 |
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