GB1583740A - Aqueous emulsions of bitumen and process for their production - Google Patents
Aqueous emulsions of bitumen and process for their production Download PDFInfo
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- 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
- C08L95/005—Aqueous compositions, e.g. emulsions
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Abstract
An aqueous bitumen and rubber emulsion is described which comprises a bituminous compound, a block copolymer with radial configuration of conjugated diene and aromatic vinyl compound and an emulsifier consisting of an amine salt and water. The process for the preparation of these aqueous bitumen and rubber emulsions consists in mixing a bituminous compound with a block copolymer with radial configuration of conjugated diene and aromatic vinyl compound, in introducing a proportion of the total quantity of amine into this mixture and in emulsifying this mixture in an aqueous phase containing the remainder of the quantity of amine as well as an acid in a quantity which is at least sufficient to neutralise all the amine. This emulsion can be employed in the field of road surfacing and roofing.
Description
(54) AQUEOUS EMULSIONS OF BITUMEN AND
PROCESS FOR THEIR PRODUCTION
(71) We, LABOFINA S.A., a Belgian
Body Corporate, of 33 rue de la Loi, 1040
Brussels, Belgium and SCREG ROUTES et
TRAVAUX PUBLICS, a French Body Corporate, of 19 rue Broca, 75240 Paris, France, do hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
The present invention relates to aqueous emulsions of bitumen and to an improved process for producing aqueous emulsions of bitumen which contain a rubbery compound.
Bituminous compositions comprising a bitumen and rubber, which is usually a copolymer of a conjugated diene containing from 4 to 12 carbon atoms and of a vinylaromatic hydrocarbon, are widely used, for example in road building, as adhesives and as coating or roofing materials.
When these compositions are used in road building, large amounts of solvent have to be added in order to lower the viscosity of these compositions and to make their application on the roads easier. However, this procedure has some drawbacks; thus, large amounts of solvent must be evaporated into the atmosphere and it is usually necessary to wait a relatively long time before admitting traffic to the road.
A first improvement has been reached by producing aqueous emulsions of bitumen and rubber. According to this process, rubber or more particularly a rubbery block copolymer of a conjugated diene and of a vinylaromatic hydrocarbon is mixed with bitumen and the mixture is then emulsified with water containing an emulsifying agent and an acid. However, it is not easy to wholly emulsify the mixture of bitumen and rubber at the temperatures generally used for their application on the road, these being of the order of from 120" to 1400C.
In fact, the amount of mixture which is emulsified does not generally exceed 40%.
The aim of the present invention is to overcome these drawbacks, by providing a novel aqueous emulsion containing a mixture of bitumen, rubber and an emulsifying agent, and by providing an improved process for producing aqueous emulsions of bitumen and rubber, which makes it possible to emulsify the whole of the mixture of bitumen and rubber.
It has been found that aqueous emulsions of bitumen and rubber having very small micelles can be obtained when the rubber is a radial block copolymer of a vinyl aromatic hydrocarbon, e.g. styrene, and butadiene.
According to one aspect of the present invention, there is provided an aqueous emulsion of bitumen and a rubber comprising:a) a bituminous compound, b) A radial block copolymer of a conjugated diene and of a vinylaromatic hydrocarbon, c) an emulsifying agent resulting from the neutralisation during emulsification of an aliphatic or alicyclic amine containing at least 10 carbon atoms with an acid to form a salt, and d) water.
According to a further aspect of the invention there is provided a process for producing aqueous emulsions of bitumen and rubber of the above mentioned kind comprising the steps of mixing a bituminous compound with a radial block copolymer of a conjugated diene and of a vinylaromatic hydrocarbon, introducing into this mixture a part of the total amount of amine which is required to produce the emulsion, and emulsifying the resulting mixture with water containing the remaining amount of amine and an acid which is used in an amount which is at least the amount required for meutralizing the total amine.
The bituminous compound, which is the main component of the aqueous emulsions of the invention, can be, for example, natural bitumen, a tar resulting from the distillation of crude oil, or oxidized or blown bitumen. A bituminous compound is generally characterised by its penetration value, which is determined by the depth (in tenths of millimeter) that a standard needle penetrates the com- pound under a load of 100 g at a temperature of 25"C and for 5 seconds (ASTM-D-551).
Another characteristic of a bitumen is its softening temperature which is determined by the Ring and Ball method (ASTM-D-3626).
The bituminous compounds used in the present invention preferably have a penetration in the range of 10 to 300 and a softening tem perature of from 25 to 950C.
The radial block copolymers are prepared from a conjugated diene and a vinylaromatic hydrocarbon, more particularly from butadiene and styrene. These block copolymers may be represented as composed of at least 3 block copolymer branches. Each branch comprises a segment of diene polymer with a segment of vinylaromatic polymer at one end. The other end is coupled to other similar branches. Such a radial block copolymer may be prepared, for example, by the procedure described in U.S.
Patent Specification No. 3,281,383. The radial block copolymers comprise generally 4 branches in a star-shaped structure. The diene polymer segment and the vinylaromatic polymer segment in each branch, as well as the total diene and the total vinyl portions of the radial block copolymer, may vary within wide limits. Generally, the amount of diene is from 50 to 70 weight % and the amount of vinylaromatic hydrocarbon is from 50 to 30 weight %. The molecular weight of these radial block copolymers may vary from 50,000 to 300,000 and is generally from 75,000 to 250,000. The amount of radial block copolymers used in the aqueous solutions of the present invention is generally from 2 to 20my, and more particularly from 4 to 15%, based on the total weight of bitumen and copolymer.
The emulsifying agents which are used in the compositions of this invention are cationic emulsifers which result from the neutralisation of an aliphatic or alicyclic amine each containing at least 10 carbon atoms, by an organic or inorganic acid, such as acetic, hydrochloric, sulfuric or phosphoric acid. According to the process of the present invention this neutralisation is carried out during emulsification of the bitumen composition. The said amine may be a mono-amine, a di-amine, a poly-amine, or a mixture of such amines. Examples of suitable amines are tallow diamine (having an alkyl chain comprising mainly 16-18 carbon atoms) or an amido-amine derivative of a resinic acid.
The choice of acid used for neutralisation of these amines will depend on its price, its availability and the technology used for preparing the emulsions. A suitable acid will be one which is easily available at low price and which is not too volatile. Hydrochloric acid is therefore particularly useful.
The amount of emulsifier which is used in the present compositions may vary between wide limits. Generally, the chosen amount of emulsifier will be the lowest amount which can be used to obtain an emulsion having a suitable stability. Moreover, too large amounts of emulsifier slow the breakdown of the emulsion after its application at the chosen site. Amounrs of emulsifiers from 0.05 to 2%, and particularly from 0.1 to 1.5%, based on the total weight of emulsion, are generally used.
A feature of the process of the present invention for producing the aqueous emulsions of bitumen and rubber consists of introducing 40 to 70% of the total amount of amine into the bitumen rubber mixture, the remaining portion of the amine being added with the acid to the aqueous phase. The whole of the bitumen rubber mixture cannot be emulsified when the total amount of amine is added either to said mixture of bitumen and rubber or to the aqueous phase.
Another characteristic of the process of the present invention is the high viscosity of the mixtures of bitumen and rubber which can be emulsified without the need of a solvent. It is known that the addition of the block copolymer to a bitumen results in a sharp increase of the viscosity of the bitumen. However if mixtures of bitumen and rubber are to be emulsified their viscosity must generally be lower than 400 centipoises at the emulsification temperature, otherwise a solvent must be used.
With the process of the invention, however, mixtures of bitumen and of radial block copolymers having a viscosity reaching 5,000 centipoises can be emulsified, without the need of any solvent, at the emulsification temperature which is generally from 140 to 1900C. It is however more convenient to use mixtures of bitumen and radial block copolymer which have a viscosity from 1,000 to 2,000 centipoises at the emulsification temperature.
The amount of water depends on the desired viscosity for the aqueous emulsion. On the one hand, it is not easy to handle an emulsion having a high viscosity at the temperature at which it is applied. On the other hand, an emulsion having too low a viscosity could flow away from the site where it has been applied. Generally, the amount of water will be from 25 to 55%, and particularly from 30 to 40%, based on the total weight of emulsion.
The aqueous phase also contains an acid which is used in an amount which is at least the amount required for the neutralisation of all the amine present both in the mixture of bitumen and radial copolymer and in the aqueous phase. This amount of acid must be sufficiently high to ensure the stability of the emulsion.
Diffusion of the amine towards the exterior of the micelles is relatively slow and may require several days. In the event of the amount of added acid not being sufficient, an emulsion which looks stable when it is prepared breaks several days later with appearance of amine compounds which are not neutralized. Generally, the amount of acid is from 1.2 to 2 times the stoichiometric amount required for neutralizing the amine used.
The following Examples illustrate the present invention. The Examples contain data on the mean size of the emulsion micelles and on the settling index which give indications respectively on the storage stability of the bituminous emulsions and on their breaking rate. The breaking rate is determined by the breaking index which is the number of grams of SiO2 which must be added to 100 g of emulsion to break said emulsion. The lower the breaking index the higher the breaking rate. This rate must be neither too small (unstable emulsions) nor too large (too stable emulsions). It is generally considered that the breaking index should be from 25 to 100. The breaking rate can also be estimated by the time required for breaking of the emulsion after its application at the site.
This rate depends also on atmospheric conditions; it is usually from 20 to 90 minutes.
EXAMPLE 1
A bitumen with a penetration of 200 and a softening point of 42"C was mixed with a radial block copolymer (M.W. 250,000), sold by Phillips Petroleum Company, U.S.A. under the trade mark Solprene 406. The amount of copolymer was 6%, based on the total weight bitumen + copolymer. The mixing time was 2 1/2 h.
0.3 % of tallow diamine and 0.075% of tallow polyamine (based on the weight of bitumen + copolymer) were added to this mixture.
The viscosity of the resulting mixture was 1,500 centipoises at 1750C (determination with a Brookfield viscosimeter).
This latter mixture was emulsified by introducing it at normal pressure and at 1 75o into a colloid mill (type Hurrell) together with an aqueous phase containing water, 0.3 wt. % of tallow diamine, 0.075 wt. % of tallow polyamine and 1.2 wt. % of hydrochloric acid (density 1.19), these percentages being based on the weight of water. This aqueous phase had a temperature of 60"C. The weight ratio of the bituminous mixture to the aqueous phase was 66 : 34.
The emulsified composition had the following characteristics: - mean size of the micelles : 3 - 5 um.
- settling index (ASTM-D-244
75) :3% - breaking index : 35 - breaking rate (on the site) : 30 minutes.
By way of comparison, the same mixture of bitumen and radial block copolymer was prepared, but no amine was added to this mixture .
Said mixture was then emulsified by introducing it at atmospheric pressure and at 1750C into a colloid mill with an aqueous phase containing 0.88 wt. % of tallow diamine, 0.23 wt. % of tallow polyamine and 1.2 wt. % of hydrochloric acid (density 1.19), these percentages being based on the weight of water. This aqueous phase had a temperature of 60"C. The weight ratio of the bituminous mixture to the aqueous phase was 66 : 34. Only 70 % of this bituminous mixture was emulsified.
In another comparative example, the same mixture of bitumen and radial block copolymer was prepared and then 0.45 wt. % (based on the weight of bitumen + copolymer) of tallow diamine and 0.12 wt. % (based on the weight of bitumen + copolymer) of tallow polyamine were added - This composition was emulsified as described above, but with the use of an aqueous phase containing only hydrochloric acid (density 1.19; 1.2 wt. % based on the weight of water). This aqueous phase had a temperature of 60"C. The weight ratio of the bituminous mixture to the aqueous phase was 66 : 34. Only 40 % of said bituminous mixture was emulsified.
EXAMPLE 2
A bitumen with a penetration of 180 and a softening point of 42"C was mixed with the radial block copolymer of Example 1. The amount of copolymer was 7 %, based on the total weight of bitumen and copolymer. The mixing time was 3 h.
0.4 % of tallow diamine and 0.1 wt. % of tallow polyamine (percentages based on the total weight of bitumen + copolymer) were added to the mixture.
The viscosity of the resulting mixture was 2,500 centipoises at 1450C (determination with a Brookfield viscosimeter).
This latter mixture was emulsified by introducing it at atmospheric pressure and at 1450C into a colloid mill (type Hurrell) with an aqueous phase containing water, 0.4 % wt. % of tallow diamine, 0.1 wt. % of tallow polyamine and 2 wt. of hydrochloric acid (d 1.19), these percentages being based on the weight of water.
The temperature of the aqueous phase was 60"C. The weight ratio of the bituminous mixture to the aqueous phase was 70 : 30.
The whole of bituminous mixture was emulsified. The emulsion had the following characteristics: - mean size of the micelles : 15 - 30 um.
settling index : 20 % - breaking index :90
EXAMPLE 3
The procedure described in Example 1 was repeated, but with the use of 1.9 wt. % (based on the amount of water) of a 85 % solution of phosphoric acid instead of hydrochloric acid - The whole of bituminous mixture was emulsified. The emulsion had the following characteristics: mean size of the micelles : 4 - 7 jim -- settling index : 4 % - breaking index : 35 EXAMPLE 4
A bitumen with a penetration of about '0 was mixed with a radial block copolymer of polystyrene and polybutadiene having a molecular weight of 150,000. The amount of copolymer was 5 wt. % based on the total weight of bitumen + copolymer.The mixture time was 2 hrs.
0.4 wt. % (based on the weight of this mixture) of amido-amine of resinic acids was added to the mixture. The viscosity of the resulting mixture at 1750C was 1,750 centipoises (as determined with a Brookfield viscosimeter).
This latter mixture was emulsified by introducing it at atmospheric pressure and at 1750C into a colloid mill (type l Hurrell) with an aqueous phase containing water, 0.4 wt. pO of the above amino compound and 0.8 wt. % of hydrochloric acid (d 1.19), these percentages being based on the weight of water. The temperature of the aqueous phase was 60 C. The weight ratio of the bituminous mixture to the aqueous phase was 66 : 34.
The whole of the bitumen was emulsified.
The emulsion had the following characteristics: - mean size of the micelles : 3 - 5 jim - settling index : 3 - breaking index : 40.
EXAMPLE 5
A bituminous composition was prepared as described in Example 1, but with the use of tallow diamine (0.4 % based on the total weight of bitumen + copolymer). The viscosity of the resulting mixture at 175 C was 1,500 centipoises.
This mixture was emulsified by introducing it at atmospheric pressure and at 1750C into a colloid mill (type Charlotte), with an aqueous phase containing water, 0.4 wt. % of tallow diamine and 1.2 wt. % of hydrochloric acid (d 1.19) these percentages being based on the amount of water. The temperature of the aqueous phase was 60"C. The weight ratio of the bituminous mixture to the aqueous phase was 68:32.
The whole of the bitumen was emulsified.
The emulsion had the following characteristics: - mean size of the micelles : 4 - 6 jim - settling index :3 - breaking index : 33
By way of comparison, the same procedure was repeated but with the use of a copolymer which was a linear block copolymer comprising blocks of polystyrene (M.W. 14,000) and blocks of polybutadiene (M.W. : 65,000).
The emulsion had the following characteristics: - mean size of the micelles : 20 - 30 jim (with some
micelles having
a size com- prised between
200 and 500 zm) - settling index :45 - breaking index :30
EXAMPLE 6
A bitumen with a penetration of about 180 was mixed with a radial block copolymer of styrene and butadiene (molecular weight 150,000). The amount of copolymer was 15 % based on the total weight of bitumen and copolymer. The mixing time was 3 hrs.
0.4 % of tallow diamine and 0.4 % of tallow polyamine (percentages based on the total weight of bitumen and copolymer) were added to the mixture. The viscosity of the resulting mixture was 4,500 centipoises at 1900C, as ileteilnincd with a Brookfield viscosimeter.
The latter mixture was emlllsified by intro ducing it at atmospheric pressure and at a temperature of 190"C into a colloid mill (type
Hurrell) together with an aqueous phase containing water, 0.4 % of tallow diamine, 0.4 % of tallow polyamine and 2 % of hydrochloric acid (d 1.19), these percentages being based on the weight of bituminous composition. The temperature of the aqueous phase was 60"C.
The weight ratio of the bituminous mixture to the aqueous phase was 60 : 40.
The whole of the bitumen was emulsified.
The emulsion had the following characteristics: - mean size of the micelles : about 80 %
between 5 and 10 jim and
about 20 % be
tween 30 and 50 jim.
- settling index : 40 - breaking index : 90
WHAT WE CLAIM IS:
1. An aqueous emulsion of bitumen and a rubber comprising:
a) a bituminous compound
b) a radial block copolymer of a conjugated
diene and of a vinylaromatic hydrocarbon,
c) an emulsifier resulting from the neutral
isation during emulsification of an aliphatic
or alicyclic amine containing at least 10
carbon atoms with an acid to form a salt, and
d) water.
2. An aqueous emulsion according to claim 1 in which the amount of water is from 25 to 55%, based on the weight of emulsion, and the amount of emulsifier is from 0.05 to 2%, based on the weight of emulsion, the remainder being a mixture of the bituminous compound and the radial block copolymer wherein the amount of copolymer is from 2 to 20 weight %.
3. An aqueous emulsion according to claim 2, in which the amount of water is from 30 to 40% based on the weight of emulsion.
4. An aqueous emulsion according to claim 2 or claim 3, in which the amount of copolymer is from 4 to 15 weight %.
5. An aqueous emulsion according to any one of the preceding claims, in which the bituminous compound has a penetration of from 10 to 300 and a softening point of from 25 to 95 95"C.
6. An aqueous emulsion according to any one of the preceding claims, in which the molecular weight of the radial block copolymer is from 50,000 to 300,000.
7. An aqueous emulsion according to claim 6, in which the molecular weight of the radial block copolymer is from 75,000 to 250,000.
8. An aqueous emulsion according to any one of the preceding claims, in which the quantity of emulsifier is from 0.05 to 2%, based on the weight of the emulsion.
9. An aqueous emulsion according to claim 8, in which the quantity of emulsifier is from 0.1 to 1.5%, based on the weight of the emulsion.
10. An aqueous emulsion according to claim
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (22)
- **WARNING** start of CLMS field may overlap end of DESC **.aqueous phase containing water, 0.4 wt. pO of the above amino compound and 0.8 wt. % of hydrochloric acid (d 1.19), these percentages being based on the weight of water. The temperature of the aqueous phase was 60 C. The weight ratio of the bituminous mixture to the aqueous phase was 66 : 34.The whole of the bitumen was emulsified.The emulsion had the following characteristics: - mean size of the micelles : 3 - 5 jim - settling index : 3 - breaking index : 40.EXAMPLE 5 A bituminous composition was prepared as described in Example 1, but with the use of tallow diamine (0.4 % based on the total weight of bitumen + copolymer). The viscosity of the resulting mixture at 175 C was 1,500 centipoises.This mixture was emulsified by introducing it at atmospheric pressure and at 1750C into a colloid mill (type Charlotte), with an aqueous phase containing water, 0.4 wt. % of tallow diamine and 1.2 wt. % of hydrochloric acid (d 1.19) these percentages being based on the amount of water. The temperature of the aqueous phase was 60"C. The weight ratio of the bituminous mixture to the aqueous phase was 68:32.The whole of the bitumen was emulsified.The emulsion had the following characteristics: - mean size of the micelles : 4 - 6 jim - settling index :3 - breaking index : 33 By way of comparison, the same procedure was repeated but with the use of a copolymer which was a linear block copolymer comprising blocks of polystyrene (M.W. 14,000) and blocks of polybutadiene (M.W. : 65,000).The emulsion had the following characteristics: - mean size of the micelles : 20 - 30 jim (with some micelles having a size com- prised between200 and 500 zm) - settling index :45 - breaking index :30 EXAMPLE 6 A bitumen with a penetration of about 180 was mixed with a radial block copolymer of styrene and butadiene (molecular weight 150,000). The amount of copolymer was 15 % based on the total weight of bitumen and copolymer. The mixing time was 3 hrs.0.4 % of tallow diamine and 0.4 % of tallow polyamine (percentages based on the total weight of bitumen and copolymer) were added to the mixture. The viscosity of the resulting mixture was 4,500 centipoises at 1900C, as ileteilnincd with a Brookfield viscosimeter.The latter mixture was emlllsified by intro ducing it at atmospheric pressure and at a temperature of 190"C into a colloid mill (type Hurrell) together with an aqueous phase containing water, 0.4 % of tallow diamine, 0.4 % of tallow polyamine and 2 % of hydrochloric acid (d 1.19), these percentages being based on the weight of bituminous composition. The temperature of the aqueous phase was 60"C.The weight ratio of the bituminous mixture to the aqueous phase was 60 : 40.The whole of the bitumen was emulsified.The emulsion had the following characteristics: - mean size of the micelles : about 80 % between 5 and 10 jim and about 20 % be tween 30 and 50 jim.- settling index : 40 - breaking index : 90 WHAT WE CLAIM IS: 1. An aqueous emulsion of bitumen and a rubber comprising: a) a bituminous compound b) a radial block copolymer of a conjugated diene and of a vinylaromatic hydrocarbon, c) an emulsifier resulting from the neutral isation during emulsification of an aliphatic or alicyclic amine containing at least 10 carbon atoms with an acid to form a salt, and d) water.
- 2. An aqueous emulsion according to claim 1 in which the amount of water is from 25 to 55%, based on the weight of emulsion, and the amount of emulsifier is from 0.05 to 2%, based on the weight of emulsion, the remainder being a mixture of the bituminous compound and the radial block copolymer wherein the amount of copolymer is from 2 to 20 weight %.
- 3. An aqueous emulsion according to claim 2, in which the amount of water is from 30 to 40% based on the weight of emulsion.
- 4. An aqueous emulsion according to claim 2 or claim 3, in which the amount of copolymer is from 4 to 15 weight %.
- 5. An aqueous emulsion according to any one of the preceding claims, in which the bituminous compound has a penetration of from 10 to 300 and a softening point of from 25 to 95 95"C.
- 6. An aqueous emulsion according to any one of the preceding claims, in which the molecular weight of the radial block copolymer is from 50,000 to 300,000.
- 7. An aqueous emulsion according to claim 6, in which the molecular weight of the radial block copolymer is from 75,000 to 250,000.
- 8. An aqueous emulsion according to any one of the preceding claims, in which the quantity of emulsifier is from 0.05 to 2%, based on the weight of the emulsion.
- 9. An aqueous emulsion according to claim 8, in which the quantity of emulsifier is from 0.1 to 1.5%, based on the weight of the emulsion.
- 10. An aqueous emulsion according to claim1, in which the amine is a mono-, di- or polyamine.
- 11. An aqueous emulsion according to claim 10, in which the amine is tallow diamine, or an amido-amine derivative of a resinic acid.
- 12. An aqueous emulsion according to claim 1, substantially as described in any one of the foregoing Examples.
- 13. A process for producing an aqueous emulsion according to any one of the preceding claims which comprises the steps of mixing a bituminous compound with a radial block copolymer of conjugated diene and of vinylaromatic hydrocarbon, introducing into this mixture a part of the total amount of amine, and emulsifying the resulting mixture with an aqueous phase containing the remaining portion of amine and an acid which is used in an amount which is at least the amount required for neutralizing the total amine.
- 14. A process according to claim 13, wherein the amine is used in an amount of from 0.05 to 2%, based on the weight of emulsion.
- 15. A process according to claim 14, wherein the amine is used in an amount of from 0.1 to 1.5%, based on the weight of emulsion.
- 16. A process according to any one of claims 13 to 15, wherein the quantity of amine which is introduced in the mixture of bituminous compound and of radial copolymer is from 40 to 70% of the total amount of amine.
- 17. A process according to any one of claims 13 to 16, wherein the emulsification is carried out at a temperature of from 140 to 1900C.
- 18. A process according to any one of claims 13 to 17, wherein the viscosity of the mixture of bituminous compound and of radial block copolymer is from 1,000 to 5,000 centipoises at the emulsification temperature.
- 19. A process according to claim 18, wherein the viscosity of the mixture of bituminous compound and of radial block copolymer is from 1,000 to 2,000 centipoises at the emulsification temperature.
- 20. A process according to any one of claims 13 to 19, wherein the acid is used in an amount offrom 1.2 to 2 times the stoichiometric amount required for neutralizing the total amount of amine.
- 21. A process according to claim 13, substantially as described in any one of the foregoing Examples.
- 22. An aqueous emulsion according to any one of claims 1 to 12 whenever produced by a process according to any one of claims 13 to 21.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7804683A FR2417526A1 (en) | 1978-02-20 | 1978-02-20 | AQUEOUS BITUMEN EMULSIONS AND METHOD FOR PREPARING THEM |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1583740A true GB1583740A (en) | 1981-02-04 |
Family
ID=9204758
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23120/78A Expired GB1583740A (en) | 1978-02-20 | 1978-05-26 | Aqueous emulsions of bitumen and process for their production |
Country Status (18)
Country | Link |
---|---|
JP (1) | JPS54111540A (en) |
BE (1) | BE874001A (en) |
BR (1) | BR7804966A (en) |
CH (1) | CH632778A5 (en) |
CS (1) | CS207641B2 (en) |
DE (1) | DE2834138B2 (en) |
DK (1) | DK169180B1 (en) |
ES (1) | ES472311A1 (en) |
FR (1) | FR2417526A1 (en) |
GB (1) | GB1583740A (en) |
HU (1) | HU180004B (en) |
IT (1) | IT1099596B (en) |
NL (1) | NL175313C (en) |
NO (1) | NO148224C (en) |
PL (1) | PL116463B1 (en) |
RO (1) | RO75079A (en) |
SE (1) | SE440228B (en) |
SU (1) | SU1109053A3 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5278207A (en) * | 1992-11-06 | 1994-01-11 | Shell Oil Company | Asphalt amine functionalized polymer composition |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU200354B (en) * | 1988-04-08 | 1990-05-28 | Chem Epitoeanyagipari | Process for emulsion modification of bitumen with elastomers |
FR2813309B1 (en) * | 2000-08-30 | 2003-02-21 | Total Raffinage Distribution | AQUEOUS SYNTHETIC BITUMEN EMULSIONS, THEIR PREPARATION PROCESS AND THEIR APPLICATIONS |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3281383A (en) * | 1962-08-09 | 1966-10-25 | Phillips Petroleum Co | Branched polymers prepared from monolithium-terminated polymers and compounds having at least three reactive sites |
US3577250A (en) * | 1968-03-20 | 1971-05-04 | Phillips Petroleum Co | Method of rubberizing asphalt |
US3565842A (en) * | 1968-06-12 | 1971-02-23 | Phillips Petroleum Co | Rubber-asphalt emulsions |
GB1338477A (en) * | 1971-02-16 | 1973-11-21 | Shell Int Research | Bituminous emulsions |
US3766107A (en) * | 1971-07-19 | 1973-10-16 | Phillips Petroleum Co | Emulsions for treating asphalts and asphalt structures and methods ofemploying the same in the treatment of asphalts and asphalt structure |
-
1978
- 1978-02-20 FR FR7804683A patent/FR2417526A1/en active Granted
- 1978-05-26 GB GB23120/78A patent/GB1583740A/en not_active Expired
- 1978-07-28 CS CS785012A patent/CS207641B2/en unknown
- 1978-08-01 NL NLAANVRAGE7808092,A patent/NL175313C/en not_active IP Right Cessation
- 1978-08-01 NO NO782620A patent/NO148224C/en unknown
- 1978-08-02 RO RO7894870A patent/RO75079A/en unknown
- 1978-08-02 BR BR7804966A patent/BR7804966A/en unknown
- 1978-08-03 DE DE2834138A patent/DE2834138B2/en active Granted
- 1978-08-03 ES ES472311A patent/ES472311A1/en not_active Expired
- 1978-08-04 CH CH835478A patent/CH632778A5/en not_active IP Right Cessation
- 1978-08-04 JP JP9534178A patent/JPS54111540A/en active Granted
- 1978-08-07 SE SE7808426A patent/SE440228B/en not_active IP Right Cessation
- 1978-08-10 SU SU782646406A patent/SU1109053A3/en active
- 1978-08-11 PL PL1978208986A patent/PL116463B1/en unknown
- 1978-08-15 DK DK360078A patent/DK169180B1/en active
- 1978-08-25 HU HU78LA942A patent/HU180004B/en unknown
- 1978-08-30 IT IT27134/78A patent/IT1099596B/en active
-
1979
- 1979-02-07 BE BE193323A patent/BE874001A/en not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5278207A (en) * | 1992-11-06 | 1994-01-11 | Shell Oil Company | Asphalt amine functionalized polymer composition |
Also Published As
Publication number | Publication date |
---|---|
BE874001A (en) | 1979-05-29 |
DE2834138B2 (en) | 1981-07-30 |
JPS5758371B2 (en) | 1982-12-09 |
IT7827134A0 (en) | 1978-08-30 |
NO148224B (en) | 1983-05-24 |
DK169180B1 (en) | 1994-09-05 |
IT1099596B (en) | 1985-09-18 |
CS207641B2 (en) | 1981-08-31 |
SE440228B (en) | 1985-07-22 |
FR2417526B1 (en) | 1980-11-14 |
JPS54111540A (en) | 1979-08-31 |
NO782620L (en) | 1979-08-21 |
NO148224C (en) | 1983-08-31 |
PL116463B1 (en) | 1981-06-30 |
CH632778A5 (en) | 1982-10-29 |
SU1109053A3 (en) | 1984-08-15 |
DE2834138A1 (en) | 1979-08-23 |
NL175313C (en) | 1986-09-16 |
ES472311A1 (en) | 1979-02-16 |
SE7808426L (en) | 1979-08-21 |
DK360078A (en) | 1979-08-21 |
BR7804966A (en) | 1979-09-25 |
NL175313B (en) | 1984-05-16 |
DE2834138C3 (en) | 1987-09-10 |
HU180004B (en) | 1983-01-28 |
PL208986A1 (en) | 1979-08-27 |
FR2417526A1 (en) | 1979-09-14 |
NL7808092A (en) | 1979-08-22 |
RO75079A (en) | 1981-08-30 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19980525 |