WO2011153267A1 - Polyphosphoric acid compositions having a reduced viscosity - Google Patents
Polyphosphoric acid compositions having a reduced viscosity Download PDFInfo
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- WO2011153267A1 WO2011153267A1 PCT/US2011/038797 US2011038797W WO2011153267A1 WO 2011153267 A1 WO2011153267 A1 WO 2011153267A1 US 2011038797 W US2011038797 W US 2011038797W WO 2011153267 A1 WO2011153267 A1 WO 2011153267A1
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- WIPO (PCT)
- Prior art keywords
- ppa
- polyphosphoric acid
- additive
- viscosity
- weight
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2555/00—Characteristics of bituminous mixtures
- C08L2555/40—Mixtures based upon bitumen or asphalt containing functional additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2555/00—Characteristics of bituminous mixtures
- C08L2555/40—Mixtures based upon bitumen or asphalt containing functional additives
- C08L2555/80—Macromolecular constituents
Definitions
- Polyphosphoric acid is typically made by the polymerization of phosphoric acid via a thermocondensation process.
- the resulting PPA product has a concentration that can be as high as 1 18% wt expressed as H 3 P0 4 content.
- PPA is composed of polymers having different chain lengths, and the composition of PPA varies with its concentration.
- PPA is used in a multitude of applications where mildly strong acidity and dehydration properties are needed.
- one of the drawbacks of PPA is that, as its concentration increases, its viscosity also increases.
- PPA viscosity of PPA
- PPA in order to easily use PPA for many processes, PPA must be heated to a sufficient temperature to reduce its viscosity to a level that it can be more easily handled and used, for example by pumping. In some processes, however, increased PPA temperature might not be desirable. In addition, PPA is sometimes stored in plastic containers that are not able to withstand the required higher temperature to allow the PPA to be pumped.
- the present invention is generally directed to polyphosphoric acid compositions having a reduced viscosity compared to neat polyphosphoric acid.
- the viscosity of the polyphosphoric acid is reduced by combining the polyphosphoric acid with an additive that reduces the viscosity of the polyphosphoric acid composition.
- additives that can cause solvation and/or partial neutralization of the PPA without the addition of water may be used.
- MEl U798180V.1 compositions is that the polyphosphoric acid can be used with little or no heating to reduce the viscosity of the polyphosphoric acid.
- Figure 1 shows a comparison of the rotational viscosity of neat PPA (1 15% wt) with a composition combining PPA (1 15% wt) with 0.1% by weight tributylphosphate at temperatures from 30°C to 100°C.
- Figure 2 shows a comparison of the rotational viscosity of neat PPA (1 15% wt) with a composition combining PPA (115% wt) with 0.1% by weight of a tall oil polyamine (Evotherm) at temperatures from 30°C to 100°C.
- Figure 3 shows the change in viscosity with temperature for various mixtures of PPA (105% wt) with tributylphosphate and dibutyl butyl phosphonate. Two of the six tests used an "aged" PPA while the remaining four tests used recently produced PPA.
- Figure 4 shows the change in viscosity with temperature for various mixtures of PPA (1 15% wt) with tributylphosphate and dibutyl butyl phosphonate.
- Polyphosphoric acid is a concentrated grade of phosphoric acid (H 3 P0 4 ) above 95%. At these high concentrations, the P0 4 unites are polymerized. PPA can have a concentration that can be as high as 118% wt expressed as H 3 P0 4 content. As the concentration and degree of polymerization of PPA increases, the viscosity also increases. As a result, PPA in its neat form can be difficult to handle at ambient temperatures. In order to use PPA in some applications, it may be necessary to pump PPA from a storage container into a mixing vessel. Due to the high viscosity of the PPA, it is often necessary to heat the PPA for pumping. This is expensive and may be difficult, particularly when the PPA is provided in a plastic storage container.
- the increase in the viscosity of the PPA as its concentration is caused by the interaction of the PPA polymers and residual monomer at a molecular level.
- the inventor has discovered that by reducing those interactions without modifying the acidity of the PPA, it is possible to reduce the viscosity of PPA at low temperatures by 80% or more depending upon the additive used. Any additive that can cause solvation and/or
- MEl 1 1798180v.l partial neutralization of the PPA without the addition of water may be used. These types of additives can prevent the hydrogen to hydrogen interaction that may cause increased viscosity of PPA.
- the PPA used in the compositions may have a concentration between 95% to 1 18% wt expressed as expressed as H 3 P0 4 content.
- the PPA may be produced by any available method, and may have the purity required for a typical application.
- the PPA is used as an additive to improve the properties of asphalt used in road paving applications.
- the additive used to reduce the viscosity of the PPA is present in a concentration sufficient to reduce the viscosity of the PPA to the desired value.
- additives that may be used to reduce the viscosity of PPA include polyamines, amines,
- the additive is present in concentrations between 0.01% by weight to 10% by weight. In other embodiments, the additive is present in concentrations between 0.02% by weight to 5% by weight. The additive may be added to achieve a concentration of 0.1 % by weight in the PPA.
- the reduced viscosity PPA of the present invention may be used for any purpose for which neat PPA may be used.
- the reduced viscosity PPA is added to asphalt to produce an improved asphalt for road pavements.
- the reduced viscosity PPA is added to neat asphalt in the amounts typically used as an additive in asphalt pavements, and the amount is determined based on the properties desired in the final asphalt product.
- reduced viscosity PPA is added to achieve a concentration of PPA of between 0.05% and 5% by weight PPA.
- reduced viscosity PPA is added to the asphalt to achieve a concentration of about 1% PPA in the asphalt.
- tributylphosphate TBP
- EvothermTMJl a tall oil polyamine
- TBP and/or DBBP dibutyl butyl phosphonate
- PPA concentration of 105% wt expressed as H 3 P0 4 content.
- the viscosity of neat PPA i.e. PPA 105% wt.
- PPA 105% wt. was measured at temperatures ranging from 30°C to 100°C and compared to the viscosity of various mixtures of the PPA with TBP, DBBP or combinations of TBP and DBBP.
- Two of the tests used "aged" PPA i.e. PPA that had been produced in December 2007, while the remaining tests used PPA that had been more recently produced. The results are shown in the chart in Figure 3.
- TBP and/or DBBP was added to PPA having a concentration of 1 15% wt expressed as H 3 P0 4 content.
- the viscosity of neat PPA i.e. PPA 1 15% wt.
- PPA 1 15% wt. was measured at temperatures ranging from 30°C to 100°C and compared to the viscosity of various mixtures of the PPA with TBP, DBBP or combinations of TBP and DBBP. The results are shown in the chart in Figure 4.
- Tests were performed to assess whether the lower viscosity PPA produced by the addition of the additives discussed above affects the properties of PPA in a particular application.
- PPA is typically used to increase the softening point of neat asphalt.
- a first composition was made composed of neat asphalt combined with standard 1 15% PPA to produce a composition having 1% by weight PPA.
- a second composition was made composed of neat asphalt combined with a reduced viscosity PPA produced by the addition of 0.1 %> Evotherm Jl .
- the softening point of the asphalt compositions is summarized in Table 1 below.
- the asphalt produced with an embodiment of the low viscosity PPA of the present invention has approximately the same softening point as that of standard PPA. This demonstrates that the low viscosity PPA is satisfactory for this application.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Working-Up Tar And Pitch (AREA)
Abstract
Polyphosphoric acid compositions having a reduced viscosity compared to neat polyphosphoric acid. The viscosity of the polyphosphoric acid is reduced by combining the polyphosphoric acid with an additive that reduces the viscosity of the polyphosphoric acid composition. In one embodiment, additives that can cause solvation and/or partial neutralization of the polyphosphoric acid without the addition of water may be used. The reduced viscosity polyphosphoric acid may be used, for example, as an additive in asphalts used in road pavements.
Description
POLYPHOSPHORIC ACID COMPOSITIONS HAVING A REDUCED
VISCOSITY
Prior Applications
This application claims the benefit of U.S. Provisional Application No.
61/396,670 filed on June 1 , 2010, the entire contents of which are hereby incorporated by reference.
Background
Polyphosphoric acid (PPA) is typically made by the polymerization of phosphoric acid via a thermocondensation process. The resulting PPA product has a concentration that can be as high as 1 18% wt expressed as H3P04 content. PPA is composed of polymers having different chain lengths, and the composition of PPA varies with its concentration. PPA is used in a multitude of applications where mildly strong acidity and dehydration properties are needed. However, one of the drawbacks of PPA is that, as its concentration increases, its viscosity also increases.
As a result of the increased viscosity of PPA, in order to easily use PPA for many processes, PPA must be heated to a sufficient temperature to reduce its viscosity to a level that it can be more easily handled and used, for example by pumping. In some processes, however, increased PPA temperature might not be desirable. In addition, PPA is sometimes stored in plastic containers that are not able to withstand the required higher temperature to allow the PPA to be pumped.
Accordingly, it would be desirable to have a PPA composition that provides the desired PPA concentration while having a viscosity that allows easy handling at lower temperatures than required by current PPA products.
Summary of the Invention
The present invention is generally directed to polyphosphoric acid compositions having a reduced viscosity compared to neat polyphosphoric acid. The viscosity of the polyphosphoric acid is reduced by combining the polyphosphoric acid with an additive that reduces the viscosity of the polyphosphoric acid composition. In one embodiment, additives that can cause solvation and/or partial neutralization of the PPA without the addition of water may be used. Among the advantages of the polyphosphoric acid
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MEl U798180V.1
compositions is that the polyphosphoric acid can be used with little or no heating to reduce the viscosity of the polyphosphoric acid.
Brief Description of the Drawings
Figure 1 shows a comparison of the rotational viscosity of neat PPA (1 15% wt) with a composition combining PPA (1 15% wt) with 0.1% by weight tributylphosphate at temperatures from 30°C to 100°C.
Figure 2 shows a comparison of the rotational viscosity of neat PPA (1 15% wt) with a composition combining PPA (115% wt) with 0.1% by weight of a tall oil polyamine (Evotherm) at temperatures from 30°C to 100°C.
Figure 3 shows the change in viscosity with temperature for various mixtures of PPA (105% wt) with tributylphosphate and dibutyl butyl phosphonate. Two of the six tests used an "aged" PPA while the remaining four tests used recently produced PPA.
Figure 4 shows the change in viscosity with temperature for various mixtures of PPA (1 15% wt) with tributylphosphate and dibutyl butyl phosphonate.
Detailed Description of Preferred Embodiments
Polyphosphoric acid (PPA) is a concentrated grade of phosphoric acid (H3P04) above 95%. At these high concentrations, the P04 unites are polymerized. PPA can have a concentration that can be as high as 118% wt expressed as H3P04 content. As the concentration and degree of polymerization of PPA increases, the viscosity also increases. As a result, PPA in its neat form can be difficult to handle at ambient temperatures. In order to use PPA in some applications, it may be necessary to pump PPA from a storage container into a mixing vessel. Due to the high viscosity of the PPA, it is often necessary to heat the PPA for pumping. This is expensive and may be difficult, particularly when the PPA is provided in a plastic storage container.
The increase in the viscosity of the PPA as its concentration is caused by the interaction of the PPA polymers and residual monomer at a molecular level. The inventor has discovered that by reducing those interactions without modifying the acidity of the PPA, it is possible to reduce the viscosity of PPA at low temperatures by 80% or more depending upon the additive used. Any additive that can cause solvation and/or
- 2 -
MEl 1 1798180v.l
partial neutralization of the PPA without the addition of water may be used. These types of additives can prevent the hydrogen to hydrogen interaction that may cause increased viscosity of PPA.
The PPA used in the compositions may have a concentration between 95% to 1 18% wt expressed as expressed as H3P04 content. The PPA may be produced by any available method, and may have the purity required for a typical application. In one embodiment, the PPA is used as an additive to improve the properties of asphalt used in road paving applications.
The additive used to reduce the viscosity of the PPA is present in a concentration sufficient to reduce the viscosity of the PPA to the desired value. Examples of additives that may be used to reduce the viscosity of PPA include polyamines, amines,
amidazoline, amidoamine, diester phosphate, triester phosphate, phosphonate, phosphinate, thiodiester phosphate, thiotriester phosphate, phosphonate, phosphinate, organic solvents or combinations thereof. In addition, surfactants used in asphalt emulsions, such as Evotherm™, Cecabase, may be used to produce the reduced viscosity PPA. In one embodiment, the additive is present in concentrations between 0.01% by weight to 10% by weight. In other embodiments, the additive is present in concentrations between 0.02% by weight to 5% by weight. The additive may be added to achieve a concentration of 0.1 % by weight in the PPA.
The reduced viscosity PPA of the present invention may be used for any purpose for which neat PPA may be used. In one embodiment, the reduced viscosity PPA is added to asphalt to produce an improved asphalt for road pavements. The reduced viscosity PPA is added to neat asphalt in the amounts typically used as an additive in asphalt pavements, and the amount is determined based on the properties desired in the final asphalt product. In one embodiment, reduced viscosity PPA is added to achieve a concentration of PPA of between 0.05% and 5% by weight PPA. In another embodiment of the invention, reduced viscosity PPA is added to the asphalt to achieve a concentration of about 1% PPA in the asphalt.
The following examples of embodiments of the invention demonstrate that the types of additives described above can reduce the viscosity of PPA at temperatures as low
- 3 -
MEl 1 1798180V.1
as 30°C to levels where the PPA can be easily handled and pumped without heating. These examples are not intended to limit the full scope of the invention in any way.
Example 1;
In this example, tributylphosphate (TBP) was added to PPA having a
concentration of 1 15% wt expressed as H3P04 content to achieve a concentration of 0.1% by weight TBP. The viscosity of neat PPA (i.e. PPA 1 15% wt.) was measured at temperatures ranging from 30°C to 100°C and compared to the viscosity of the TBP/PPA mixture. The results are shown in Figure 1.
As can be seen in Figure 1 , the addition of TBP slightly reduced the viscosity of the PPA at low temperatures, and had less effect on the viscosity at higher temperatures.
Example 2;
In this example, Evotherm™Jl , a tall oil polyamine, was added to PPA having a concentration of 1 15% wt expressed as H3P04 content to achieve a concentration of 0.1% by weight Evotherm in the PPA. The viscosity of neat PPA (i.e. PPA 1 15% wt.) was measured at temperatures ranging from 30°C to 100°C and compared to the viscosity of the 0.1% Evotherm/PPA mixture. The results are shown in the chart in Figure 2.
As can be seen in Figure 2, the viscosity of the Evotherm/PPA mixtures is greatly reduced at all temperatures as compared to neat PPA.
Example 3
In this example, TBP and/or DBBP (dibutyl butyl phosphonate) was added to PPA having a concentration of 105% wt expressed as H3P04 content. The viscosity of neat PPA (i.e. PPA 105% wt.) was measured at temperatures ranging from 30°C to 100°C and compared to the viscosity of various mixtures of the PPA with TBP, DBBP or combinations of TBP and DBBP. Two of the tests used "aged" PPA, i.e. PPA that had been produced in December 2007, while the remaining tests used PPA that had been more recently produced. The results are shown in the chart in Figure 3.
- 4 - El 1 1798180V.1
This data illustrates that the effect of TBP on the viscosity of PPA depends on both the temperature and the age of the PPA. As shown in Figure 3, the effect of the addition of TBP and DBBP was greater in tests using the "aged" PPA.
Example 4
In this example, TBP and/or DBBP was added to PPA having a concentration of 1 15% wt expressed as H3P04 content. The viscosity of neat PPA (i.e. PPA 1 15% wt.) was measured at temperatures ranging from 30°C to 100°C and compared to the viscosity of various mixtures of the PPA with TBP, DBBP or combinations of TBP and DBBP. The results are shown in the chart in Figure 4.
As shown in Figure 4, at low temperatures (for example below 70°C), the addition of TBP and/or DBBP reduces the viscosity of the 1 15%) PPA significantly below the viscosity of neat 115% PPA.
Example 5
Tests were performed to assess whether the lower viscosity PPA produced by the addition of the additives discussed above affects the properties of PPA in a particular application. PPA is typically used to increase the softening point of neat asphalt. A first composition was made composed of neat asphalt combined with standard 1 15% PPA to produce a composition having 1% by weight PPA. A second composition was made composed of neat asphalt combined with a reduced viscosity PPA produced by the addition of 0.1 %> Evotherm Jl . The softening point of the asphalt compositions is summarized in Table 1 below.
Table 1
As can be seen in the results in Table 1 , the asphalt produced with an embodiment of the low viscosity PPA of the present invention has approximately the same softening point as that of standard PPA. This demonstrates that the low viscosity PPA is satisfactory for this application.
ME l 1 1798180V.1
Example 6
In this example, 2-ethyl hexyl phosphoric acid was added to PPA having a concentration of 1 15% wt expressed as H3P04 content. The viscosity of neat PPA (i.e. PPA 115% wt.) was measured at 70°C and compared to the viscosity of mixtures of PPA with various concentrations of ethyl hexyl phosphoric acid. Four different lots of PPA were used for the testing. The results are shown in Table 2 below.
Table 2
As can be seen from the results in Table 2, all of the compositions containing ethyl hexyl phosphate have a reduced viscosity compared to neat PPA. The viscosity is further reduced as the concentration of ethyl hexyl phosphate is increased.
While preferred embodiments have been shown and described, various modifications may be made to the processes described above without departing from the spirit and scope of the invention as described in the appended claims. Accordingly, it is to be understood that the present invention has been described herein by way of example and not by limitation.
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MEl 1 1798180v. l
Claims
1. A reduced viscosity polyphosphoric acid composition comprising polyphosphoric acid having an acid concentration of between 95% and 118% wt expressed as H3P04 content and from about 0.01% by weight to about 10% by weight of an additive that reduces the viscosity of the polyphosphoric acid.
2. The reduced viscosity polyphosphoric acid composition of claim 1, wherein the additive is selected from the group consisting of polyamines, amines, amidazoline, amidoamine, diester phosphate, triester phosphate, phosphonates, phosphinates, thiodiester phosphate, thiotriester phosphate, phosphomate, phosphinate, organic solvents or combinations thereof.
3. The reduced viscosity polyphosphoric acid composition of claim 1 , wherein the additive is selected from the group consisting of tributylphosphate, dibutyl butyl phosphonate and combinations thereof.
4. The reduced viscosity polyphosphoric acid composition of claim 3, wherein the additive concentration in the polyphosphoric acid is between about 0.02% and 0.2% by weight.
5. The reduced viscosity polyphosphoric acid composition of claim 1, wherein the additive is a tall oil polyamine.
6. The reduced viscosity polyphosphoric acid composition of claim 5, wherein the additive concentration in the polyphosphoric acid is between about 0.02% and 0.2% by weight.
7. The reduced viscosity polyphosphoric acid composition of claim 1 , wherein the additive is 2-ethyl hexyl phosphoric acid.
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MEl 1 1798180V.1
8. The reduced viscosity polyphosphoric acid composition of claim 7, wherein the additive concentration in the polyphosphoric acid is between about 0.02% and 0.5% by weight.
9. An asphalt composition comprising (a) asphalt and (b) .polyphosphoric acid having an acid concentration of between 95% and 1 18% wt expressed as H3P04 content and from about 0.01%) by weight to about 10% by weight of an additive that reduces the viscosity of the polyphosphoric acid.
10. The asphalt composition of claim 9, wherein the additive is selected from the group consisting of polyamines, amines, amidazoline, amidoamine, diester phosphate, triester phosphate, phosphonates, phosphinates, thiodiester phosphate, thiotriester phosphate, phosphomate, phosphinate, organic solvents or combinations thereof.
1 1. The asphalt composition of claim 9, wherein the additive is selected from the group consisting of tributylphosphate, dibutyl butyl phosphonate and combinations thereof.
12. The asphalt composition of claim 1 1, wherein the additive concentration in the polyphosphoric acid is between about 0.02% and 0.2% by weight.
13. The asphalt composition of claim 9, wherein the additive is a tall oil polyamine.
14. The asphalt composition of claim 13, wherein the additive concentration in the polyphosphoric acid is between about 0.02% and 0.2% by weight.
15. The asphalt composition of claim 9, wherein the additive is 2-ethyl hexyl phosphoric acid.
16. The asphalt composition of claim 15, wherein the additive concentration in the polyphosphoric acid is between about 0.02% and 0.5% by weight.
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MEl 1 1798180v.l
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11790352.6A EP2576437B1 (en) | 2010-06-01 | 2011-06-01 | Polyphosphoric acid compositions having a reduced viscosity |
PL11790352T PL2576437T3 (en) | 2010-06-01 | 2011-06-01 | Polyphosphoric acid compositions having a reduced viscosity |
LTEP11790352.6T LT2576437T (en) | 2010-06-01 | 2011-06-01 | Polyphosphoric acid compositions having a reduced viscosity |
CN201180027565.3A CN103221337B (en) | 2010-06-01 | 2011-06-01 | The polyphosphoric acid composition of decrease in viscosity |
ES11790352.6T ES2681648T3 (en) | 2010-06-01 | 2011-06-01 | Polyphosphoric acid compositions having a reduced viscosity |
ZA2012/09375A ZA201209375B (en) | 2010-06-01 | 2012-12-11 | Polyphosphoric acid compositions having a reduced viscosity |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39667010P | 2010-06-01 | 2010-06-01 | |
US61/396,670 | 2010-06-01 |
Publications (1)
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WO2011153267A1 true WO2011153267A1 (en) | 2011-12-08 |
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ID=45067063
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Application Number | Title | Priority Date | Filing Date |
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PCT/US2011/038797 WO2011153267A1 (en) | 2010-06-01 | 2011-06-01 | Polyphosphoric acid compositions having a reduced viscosity |
Country Status (9)
Country | Link |
---|---|
US (1) | US8801849B2 (en) |
EP (1) | EP2576437B1 (en) |
CN (1) | CN103221337B (en) |
ES (1) | ES2681648T3 (en) |
LT (1) | LT2576437T (en) |
PL (1) | PL2576437T3 (en) |
TR (1) | TR201810030T4 (en) |
WO (1) | WO2011153267A1 (en) |
ZA (1) | ZA201209375B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104684402A (en) * | 2012-07-24 | 2015-06-03 | 雪印惠乳业株式会社 | Processed cheese and manufacturing method therefor |
WO2018055315A1 (en) | 2016-09-26 | 2018-03-29 | Eurovia | Hydrocarbon-based mix suitable for integrating a heat exchanger device |
WO2018055314A2 (en) | 2016-09-26 | 2018-03-29 | Eurovia | Method for the high-speed embedding of a recyclable heat exchanger in land-based infrastructure |
WO2018224781A1 (en) | 2017-06-07 | 2018-12-13 | Eurovia | Method for producing a road surface comprising a heat exchanger device |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3007035A1 (en) * | 2013-06-13 | 2014-12-19 | Ceca Sa | ADDITIVES FOR INDUSTRIAL BITUMES |
CN108439359A (en) * | 2018-04-02 | 2018-08-24 | 安徽赛诺制药有限公司 | A kind of technique using wet phosphoric acid purifying acid polyphosphoric acids |
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US2541027A (en) * | 1948-05-11 | 1951-02-13 | Shell Dev | Compositions of matter containing epoxy ethers and phosphorus-containing compounds |
US4397970A (en) * | 1981-06-24 | 1983-08-09 | The Dow Chemical Company | Process for epoxy phosphate coating resins |
US20090068348A1 (en) * | 2007-09-07 | 2009-03-12 | Reinke Gerald H | Warm asphalt binder compositions containing lubricating agents |
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US3751278A (en) * | 1972-03-06 | 1973-08-07 | Tosco Lion Inc | Method of treating asphalt |
CA2044407A1 (en) * | 1990-06-15 | 1991-12-16 | William C. Uy | Anisotropic spin dopes of reduced viscosity |
FR2739863B1 (en) * | 1995-10-16 | 1997-11-21 | Elf Antar France | PROCESS FOR THE PREPARATION OF BITUMEN / POLYMER COMPOSITIONS WITH REINFORCED MULTIGRADE CHARACTER AND APPLICATION OF THE COMPOSITIONS OBTAINED IN THE PRODUCTION OF BITUMEN / POLYMER BINDERS FOR COATINGS |
US6261356B1 (en) * | 1998-09-11 | 2001-07-17 | Kao Corporation | Asphalt-additive composition |
FR2841561B1 (en) * | 2002-07-01 | 2004-08-06 | Rhodia Cons Spec Ltd | BITUMINOUS PRODUCT AND ITS PREPARATION PROCESS |
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WO2011057085A2 (en) * | 2009-11-06 | 2011-05-12 | Innophos, Inc. | Asphalt additive with improved performance |
-
2011
- 2011-06-01 LT LTEP11790352.6T patent/LT2576437T/en unknown
- 2011-06-01 WO PCT/US2011/038797 patent/WO2011153267A1/en active Application Filing
- 2011-06-01 CN CN201180027565.3A patent/CN103221337B/en not_active Expired - Fee Related
- 2011-06-01 US US13/151,038 patent/US8801849B2/en not_active Expired - Fee Related
- 2011-06-01 EP EP11790352.6A patent/EP2576437B1/en active Active
- 2011-06-01 PL PL11790352T patent/PL2576437T3/en unknown
- 2011-06-01 TR TR2018/10030T patent/TR201810030T4/en unknown
- 2011-06-01 ES ES11790352.6T patent/ES2681648T3/en active Active
-
2012
- 2012-12-11 ZA ZA2012/09375A patent/ZA201209375B/en unknown
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THERMPHOS: "Polyphosphoric acids", 2005, XP055131786, Retrieved from the Internet <URL:http://www.thermphos.com/en/Products%20Quick%20Searoh/Polyphosphoric%20acids.aspx> [retrieved on 20110901] * |
Cited By (6)
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WO2018055315A1 (en) | 2016-09-26 | 2018-03-29 | Eurovia | Hydrocarbon-based mix suitable for integrating a heat exchanger device |
WO2018055314A2 (en) | 2016-09-26 | 2018-03-29 | Eurovia | Method for the high-speed embedding of a recyclable heat exchanger in land-based infrastructure |
US10711413B2 (en) | 2016-09-26 | 2020-07-14 | Eurovia | Method for the high speed indentation of a recyclable heat exchanger in a land-based infrastructure |
WO2018224781A1 (en) | 2017-06-07 | 2018-12-13 | Eurovia | Method for producing a road surface comprising a heat exchanger device |
US11371193B2 (en) | 2017-06-07 | 2022-06-28 | Eurovia | Method for manufacturing a road pavement comprising a heat exchanger device |
Also Published As
Publication number | Publication date |
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CN103221337B (en) | 2016-06-08 |
US20120006227A1 (en) | 2012-01-12 |
ES2681648T3 (en) | 2018-09-14 |
CN103221337A (en) | 2013-07-24 |
EP2576437B1 (en) | 2018-05-02 |
TR201810030T4 (en) | 2018-08-27 |
US8801849B2 (en) | 2014-08-12 |
EP2576437A4 (en) | 2015-04-08 |
EP2576437A1 (en) | 2013-04-10 |
PL2576437T3 (en) | 2018-10-31 |
LT2576437T (en) | 2018-11-12 |
ZA201209375B (en) | 2016-08-31 |
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