PatentDe  


Dokumentenidentifikation EP0326125 19.11.1992
EP-Veröffentlichungsnummer 0326125
Titel Plastifizierungsmittel, Verfahren zu seiner Herstellung sowie seine Verwendung.
Anmelder Perstorp AB, Perstorp, SE
Erfinder Olsson, Lars-Inge R., S-252 33 Helsingborg, SE;
Hamacek, Kent F., S-284 00 Perstorp, SE
Vertreter Eitle, W., Dipl.-Ing.; Hoffmann, K., Dipl.-Ing. Dr.rer.nat.; Lehn, W., Dipl.-Ing.; Füchsle, K., Dipl.-Ing.; Hansen, B., Dipl.-Chem. Dr.rer.nat.; Brauns, H., Dipl.-Chem. Dr.rer.nat.; Görg, K., Dipl.-Ing.; Kohlmann, K., Dipl.-Ing.; Ritter und Edler von Fischern, B., Dipl.-Ing.; Kolb, H., Dipl.-Chem. Dr.rer.nat., Pat.-Anwälte; Nette, A., Rechtsanw., 8000 München
DE-Aktenzeichen 68903177
Vertragsstaaten AT, BE, CH, DE, FR, GB, IT, LI, NL, SE
Sprache des Dokument En
EP-Anmeldetag 26.01.1989
EP-Aktenzeichen 891013369
EP-Offenlegungsdatum 02.08.1989
EP date of grant 14.10.1992
Veröffentlichungstag im Patentblatt 19.11.1992
IPC-Hauptklasse C04B 24/22

Beschreibung[en]

The present invention relates to a flowability improving agent, a process for the production thereof and a use thereof.

The flowability improving agent is mostly intended as an additive to a composition containing cement, lime and/or gypsum.

It is well-known that cement based mixtures, for instance mortar, plaster, concrete, putty and screeding are composed in such a way that they contain a surplus of water as compared to the minimum amount necessary for the curing or binding reaction of the cement.

If you tried to use exactly the amount of water necessary for the curing, the mixture would get an unsatisfactory consistency and workability due to the strong attractive forces between the cement particles.

On the other hand, a too high water content in the mixture mentioned results in a drastic decrease of the strength of the cured mixture. However, to a certain extent this can be compensated by an increase of the cement content at the composition of the mixture. A too high content of cement per unit of volume has, however, the negative effect that the heat release at the curing reaction results in crack formations and other less desirable effects. Also from an economical viewpoint it is undesirable with a higher content of cement that necessary.

Nowadays, cement based mixtures are often pumped under pressure through a pipeline at the use on the different building work sites. Then it is important that the mixture has a pumpable consistency but not a too high water content.

It is known before to use certain concrete additives to be able to decrease the water content of the concrete mixture and at the same time get a good flowability. The most known of these additives are sulphonated naphtalene formaldehyde resins, sulphonated melamine formaldehyde resins and sodium and calcium salts of ligninsulphonic acid.

Thus, these known additives give a certain effect in the respect mentioned above, but in many cases it is desirable with still better effect. Up to now this has, however, not been possible to attain.

According to the present invention it has now quite unexpectedly been possible to solve the above problem and bring about a flowability improving agent comprising a combination of

  • A) a sulphonated melamine-formaldehyde resin, a sulphonated melamine-urea-formaldehyde resin or a sulphonated naphtalene-formaldehyde resin and
  • B) a compound with the general formula
    where Ar is a possibly substituted benzene group or naphtalene group, R&sub1; is an oxyethylene group;

    - CH&sub2;CH&sub2;O - or an oxypropylene group;
    an oxyethylene chain or an oxypropylene chain with up to fifteen oxyethylene groups or oxypropylene groups or a combination of oxyethylene groups and oxypropylene groups to a chain where the sum of these groups is at most fifteen; the mean value n for n is 1-15 and R2 is hydrogen or a phosphonate group with the formula
    where M&sub1; and M&sub2; are hydrogen ion or alkali metal ion or where R&sub2; is a group with the formula
    where M&sub2; has the above meaning and M&sub3; is
    where R&sub1;, n and Ar have the above meaning.

The compound A) of the flowability improving agent can be produced in many different ways. One suitable method is shown in the Swedish patent 7414830-5, which discloses sulphonated melamine-formaldehyde resins. The commercial product Melment L-10 sold by Cementa under the name Cementa flow additive V 33 as well as the products PERAMIN F® and PERAMIN F P®, both sold by Perstorp AB, can be used as component A) according to the present invention.

The published Japanese patent application 57-100959 also relates to production of sulphonated melamine-formaldehyde resins. Said process can be used too at the production of the component A) above.

Furthermore, the U.S. patent 2,730,516, the Austrian patent 263,607 and the European patent 59,353 can be mentioned. They also relate to the production of sulphonated melamine-formaldehyde resins.

Sulphonated naphtalene-formaldehyde resins are also commercially available for instance from the French company Compagnie Francaise De Produits Industriels.

Certain embodiments of the component B) of the flowability improving agent are disclosed before in the German patent 2,461,359. Said patent concerns a method of preventing corrosion on iron and steel in cement products containing chlorides. Then, a mixture of nitrite and a polyoxyethylene phosphoric acid ester, an alkyl phosphoric acid ester, a phenyl phosphoric acid ester or an alkylaryl phosphoric acid ester or a combination of nitrite and a boric acid ester is added to the cement.

The addition of the mentioned phosphoric acid ester and boric acid ester respectively to the nitrite is said to increase the rust protecting properties of the nitrite on iron and steel in the concrete. By the way, from examples 27-35 in Table 1 of the German patent it is evident that the phosphoric acid ester does not per se give any rust protecting effect.

Consequently, the presence of nitrite in the known mixture is quite necessary.

No flowability improving effect at all of the known additive is mentioned in the German patent. This is rather natural in itself, since neither the known combination of nitrite and phosphoric acid ester, nor solely phosphoric acid ester gives any such effect. This will be shown below.

Accordingly, the present invention solves a totally different problem than that according to the German patent.

It is very surprising that you can achieve a flowability improving effect according to the present invention by a combination of the components A) and B) above. As mentioned above, the component B) does not per se give any flowability improving effect at all on the present products.

According to a preferred embodiment of the invention, R&sub1; in the compound B) is an oxyethylene group and n is 1-6.

In another preferred embodiment of the invention, R&sub1; in the compound B) consists of an oxypropylene group, whereby n is 3-8.

Ar in the compound B) is preferably a benzene group and R&sub2; is a phosphonate group with the formula

where M&sub1; and M&sub2; are hydrogen ion or alkali metal ion.

It is very suitable to use a sulphonated melamine-formaldeyde resin or a sulphonated melamine-urea-formaldehyde resin as component A).

The flowability improving agent consists of 0.5-30, preferably 0.5-20% by weight of B) and 99.5-70, preferably 99.5-80% by weight of A) calculated on a dry product.

Of course, this composition can then be mixed with other components on condition that they do not have a bad influence on the properties of the flowability improving agent.

If Ar in the compound B) is substituted with an alkyl group this should preferably consist of short chains, such as CH&sub3;, C&sub2;H&sub5; or C&sub3;H&sub7;.

Polyoxyalkyl phosphoric acid esters do not give a good flowability improving ability in combination with the component A).

At one process for production of the flowability improving agent according to the invention, the compound B) above is added at the production of a sulphonated melamine-formaldehyde resin or a sulphonated melamine-urea-formaldehyde resin A).

Usually, an acid reaction step is included at the production of such resins. There, the low pH value is brought about by means of an acid catalyst, for example consisting of an inorganic acid such as sulphuric acid, an organic acid or another acid compound.

Advantageously, the component B) can be added at said step. If the compound B) has a phosphonate group, this can work as an acid catalyst and then wholly or partly replace the above catalysts, which are usual in this connection.

However, the component B) can also be added at another step of the production of the resin A). Especially, this is the case if the component B) has no phosphonate group.

Finally, the component B) can be added to a finished resin A).

An addition of the component B) in more than one step is also possible.

Even if the flowability improving agent according to the invention has been disclosure above as an additive to cement and/or gypsum containing compositions, it is useful for virtually all compositions containing one or more of the following products; cement, lime, gypsum, talc, chalk or titanium dioxide.

The invention will be further explained in connection with the embodiment examples below, of which examples 1-6 relate to production of different flowability improving agents according to the invention, while examples 7-10 show different technical experiments, where these agents were used.

Example 1

1114.0 g water and 753 g 37% formaldehyde were charged into a reaction bulb made of glass. 280 g melamine, 54.5 g urea and 291 g sodiummetabisulphite were added at stirring. The reaction mixture was heated to 75°C while stirring. When the melamine, the urea and the sodiummetabisulphite had been completely dissolved and the reaction mixture had cleared up, 15.0 g 46% sodium hydroxide was added to get a pH of 10.5-11.2. The reaction mixture was kept at 75°C until free sulphite could not be detected any longer (about 0.5-2 h).

Then the reaction mixture was cooled down to 50°C. Thereafter, 66.0 g of a compound B) as disclosed above, where Ar is phenol, R&sub1; is - CH&sub2;CH&sub2;O -, n is 4 and R&sub2; is

and 10.0 g 96% sulphuric acid were added, whereby a pH of 5.2 was obtained. The condensation reaction was then continued for about 4 hours until a viscosity of 170 cp (Emilia) was obtained. Then the reaction mixture was cooled to 35°C and the pH was adjusted to 10.8 with 41.0 g 46% sodium hydroxide to give the condensation product a satisfactory storage stability.

Example 2

970 g PERAMIN F® from Perstorp AB and 30 g of the component B disclosed in example 1 were mixed while stirring at a temperature of 35°C until a homogeneous mixture was obtained. Then the pH was adjusted by addition of sodium hydroxide.

Example 3

The process according to Example 2 was repeated with the difference that a compound B as defined above, where Ar is phenol

n&sub1; is 4 and

n&sub2; is 3 and

was used.

Example 4

970 g sulphonated naphtalene-formaldehyde resin, GALORYL® LH 1640 from Compagnie Francaise De Produits Industriels was mixed while stirring at 35°C with 30 g of a compound B as defined above, where

Ar is phenol

R&sub1; is - CH&sub2;CH&sub2;O -

n is 4 and

until a homogeneous mixture was obtained.

Example 5

The product produced according to Example 1 was spray dried to a dry powder.

Example 6

The product produced according to Example 2 was spray dried to a dry powder.

Example 7

A cement mortar with the following composition was mixed: 230 g sand (0-1 mm) 180 g cement (Slite Std P) 180 g limestone powder 13 g hydraulic lime 10 g alumina cement

375 g of the above mixture was removed and mixed with different dosages of flowability improving agent. The cement mortar was mixed with 69.2 g water during 2 minutes and then charged into a steel ring with an inner diameter of 80 mm and a height of 40 mm. The ring was placed on an even underlayer. The ring was then lifted when it had been filled and the flow of the cement mortar gives a measure of the flowability improving effect. Flow cm: Flowability improving agent Dosage 2 g 3 g 4 g 6 g 8 g 10 g 15 g 20 g PERAMIN F P (powder) 8.5 18.0 23.0 25.5 26.0 26.0 25.0 24.5 Product according to Example 6 18.0 24.0 26.0 27.0 27.5 27.0 - - Product according to Example 5 11.0 24.0 26.0 27.0 27.0 28.0 28.0 28.0

The above results show that a considerable flowability improvement is achieved at low dosages of the products according to the invention as compared to the known product PERAMIN F P.

Example 8

A cement mortar with the following composition was mixed: 230 g sand (0-1 mm) 180 g cement (Slite Std P) 10 g alumina cement 180 g limestone powder 13 g hydraulic lime

375 g of the above mixture was removed and mixed with 8 g flowability improving agent. The cement mortar was then mixed with 69.2 g water at 0% water reduction. The amount of water was then gradually reduced to test the water reducing ability of the flowability improving agent. Otherwise the test was made in the same way as according to Example 7. Spread cm Cement additive Water reduction % 0 5 10 15 17 20 21 PERAMIN F P 26.0 24.0 21.0 17.0 11.0 8.0 8.0 According to Example 6 27.5 25.5 23.5 22.0 21.0 20.5 19.0 According to Example 5 27.0 24.0 23.0 21.5 18.5 16.0 14.0

The above results show that a good workability of the cement mortar can be maintained also at a considerable water reduction by an addition of the flowability improving agent according to the invention.

Example 9

330 g Std Portland cement and 99 g water were mixed for two minutes to a homogeneous paste. Then 4.3 g (1.3% dosage calculated on the weight of the cement) of the 35% flowability improving agent was added. The flowability improving agent was then mixed with the cement paste for another 2 minutes. A steel ring with an inner diameter of 80 mm and a height of 40 mm was placed on an even underlayer and filled with the easily flowing cement paste. When the steel ring is lifted the spread of the cement paste gives a measure of the flowability improving effect of the additive used. Additive Spread (mm) Product according to Example 1 265 mm Product according to Example 2 270 mm Product according to Example 3 260 mm Product according to Example 4 270 mm PERAMIN F 200 mm Galoryl LH 1640 220 mm Component B according to Example 1 80 mm Component B + sodium/nitrite (9:1) 80 mm

The above results show that the flowability improving agent according to the invention gives a very good effect also in a cement paste. However, component B and a mixture of component B and sodium nitrite respectively did not give any flowability improving effect at all in the cement paste.

Example 10

A concrete with the following composition was produced:

The dosage of the additive was calculated on the weight of the cement. The dry content of the additive was 35.0%. Additive Dosage % on the content Slump SS137124 Water/cement ratio Strength SS137210 1 day MPa 7 days MPa 28 days MPa Without additive - 75 mm 0.638 10.7 26.5 34.9 PERAMIN F 1.3 85 mm 0.562 17.8 35.1 45.0 According to Ex 1 1.3 75 mm 0.543 12.5 39.1 50.0 According to Ex 2 1.3 85 mm 0.535 24.0 41.0 52.1

Compressive strength cubes were produced from the concrete mixtures according to SS 137210 (15x15x15 cm), whereupon the strength was measured at different points of time. The storage temperature was 20°C ± 2°C.

The above results show that a high strength of the contrete is obtained at the use of the agent according to the invention. This can be attributed to a decrease of the water/cement ratio.

The present invention is not limited to the embodiments shown, since these can be modified in different ways within the scope of the invention.


Anspruch[de]
  1. Plastifizierungsmittel, umfassend eine Kombination von
    • A) einem sulfonierten Melamin-Formaldehyd-Harz, einem sulfonierten Melamin-Harnstoff-Formaldehyd-Harz oder einem sulfonierten Naphthalin-Formaldehyd-Harz und
    • B) eine Verbindung mit der allgemeinen Formel
      worin Ar eine gegebenenfalls substituierte Benzolgruppe oder Naphthalingruppe ist, R&sub1; eine Oxyethylengruppe;

      -CH&sub2;CH&sub2;O- oder eine Oxypropylengruppe;
      eine Oxyethylenkette oder eine Oxypropylenkette mit bis zu 15 Oxyethylengruppen oder Oxypropylengruppen oder eine Kombination von Oxyethylengruppen und Oxypropylengruppen zu einer Kette, in der die Summe dieser Gruppen höchstens 15 beträgt, ist; der mittlere Wert n für n 1 - 15 ist, und R&sub2; Wasserstoff oder eine Phosphonatgruppe der Formel
      ist, worin M&sub1; und M&sub2; ein Wasserstoffion oder ein Alkalimetallion sind, oder worin R&sub2; eine Gruppe der Formel
      ist, worin M&sub2; die vorstehende Bedeutung hat, und M&sub3;
      ist, worin R&sub1;, n und Ar die vorstehend genannten Bedeutungen besitzt.
  2. Plastifizierungsmittel gemäß Anspruch 1, dadurch gekennzeichnet, daß R&sub1; in Verbindung B eine Oxyethylengruppe ist und n 1 - 6 ist.
  3. Fließbarkeitsmittel nach Anspruch 1, dadurch gekennzeichnet, daß R&sub1; in Verbindung B eine Oxypropylengruppe und n 3 - 8 ist.
  4. Plastifizierungsmittel nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß Ar in der Verbindung B ein Benzolrest ist, und R&sub2; eine Phosphonatgruppe mit der Formel
    ist, worin M&sub1; und M&sub2; Wasserstoffion oder Alkalimetallion sind.
  5. Plastifizierungsmittel nach einem der Ansprüche 2 bis 4, dadurch gekennzeichnet, daß A) ein sulfoniertes Melamin-Formaldehyd-Harz oder ein sulfoniertes Melamin-Harnstoff-Formaldehyd-Harz ist.
  6. Plastifizierungsmittel nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß es 0.5 bis 30, vorzugsweise 0.5 bis 20 Gew.-% B) und 99.5 bis 70, vorzugsweise 99.5 bis 80 Gew.-% A), bezogen auf ein trockenes Produkt, enthält.
  7. Plastifizierungsmittel nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß Ar in der Verbindung B) mit einer Alkylgruppe, vorzugsweise CH&sub3;, C&sub2;H&sub5; oder C&sub3;H&sub7;, substituiert ist.
  8. Verfahren zur Herstellung eines Plastifizierungsmittels, dadurch gekennzeichnet, daß eine Verbindung B) der allgemeinen Formel
    worin Ar eine gegebenenfalls substituierte Benzolgruppe oder Naphthalingruppe ist, R&sub1; eine Oxyethylengruppe;

    -CH&sub2;CH&sub2;O- oder eine Oxypropylengruppe,
    eine Oxyethylenkette oder eine Oxypropylenkette mit bis zu 15 Oxyethylengruppen oder Oxypropylengruppen oder eine Kombination von Oxyethylengruppen und Oxypropylengruppen für eine Kette, in der die Summe dieser Gruppen höchstens 15 beträgt, ist;

    der mittlere Wert n für n 1 - 15 ist, und R&sub2; Wasserstoff oder eine Phosphonatgruppe der Formel
    ist, worin M&sub1; und M&sub2; Wasserstoffion oder Alkalimetallion sind, oder worin R&sub2; eine Gruppe mit der Formel
    ist, worin M&sub2; die vorstehend angegebene Bedeutung besitzt, und M&sub3;
    worin R&sub1;, n und Ar die vorstehend angegebene Bedeutung besitzen,

    bei der Herstellung eines Harzes A), das aus einem sulfonierten MelaminFormaldehyd-Harz oder einem sulfonierten Melamin-Harnstoff-FormaldehydHarz besteht, zugegeben wird.
  9. Verwendung eines Plastifizierungsmittels, umfassend 99.5 - 70 Gew.-%, bezogen auf ein Trockenprodukt, von A) einem sulfonierten Melamin-Formaldehyd-Harz, einem sulfonierten Melamin-HarnstoffFormaldehyd-Harz oder einem sulfonierten Naphthalin-Formaldehyd-Harz und 0.5 - 30 Gew.-% einer Verbindung B) mit der allgemeinen Formel
    worin Ar eine gegebenenfalls substituierte Benzolgruppe oder Naphthalingruppe ist, R&sub1; eine Oxyethylengruppe,

    -CH&sub2;CH&sub2;O- oder eine Oxypropylengruppe,
    eine Oxyethylenkette oder eine Oxypropylenkette mit bis zu 15 Oxyethylengruppen oder Oxypropylengruppen oder eine Kombination von Oxyethylengruppen und Oxypropylengruppen für eine Kette, worin die Summe dieser Gruppen höchstens 15 beträgt ist;

    der mittlere Wert n für n 1 - 15 ist und R&sub2; Wasserstoff oder eine Phosphonatgruppe der Formel
    ist, worin M&sub1; und M&sub2; Wasserstoffion oder Alkalimetallion sind;

    als Additiv für eine Zusammensetzung, die ein oder mehrere der folgenden Produkte enthält: Zement, Kalk, Gips, Talk, Kalkstein oder Titandioxid.
Anspruch[en]
  1. Flowability improving agent, comprising a combination of
    • A) a sulphonated melamine-formaldehyde resin, a sulphonated melamine-urea-formaldehyde resin or a sulphonated naphtalene-formaldehyde resin and
    • B) a compound with the general formula
      where Ar is a possibly substituted benzene group or naphtalene group, R&sub1; is an oxyethylene group;

      - CH&sub2;CH&sub2;O - or an oxypropylene group;
      an oxyethylene chain or an oxypropylene chain with up to fifteen oxyethylene groups or oxypropylene groups or a combination of oxyethylene groups and oxypropylene groups to a chain where the sum of these groups is at most fifteen; the mean value n for n is 1-15 and R&sub2; is hydrogen or a phosphonate group with the formula
      where M&sub1; and M&sub2; are hydrogen ion or alkali metal ion or where R&sub2; is a group with the formula
      where M&sub2; has the above meaning and M&sub3; is
      where R&sub1;, n and Ar have the above meaning.
  2. Flowability improving agent according to claim 1, wherein R&sub1; in the compound B is an oxyethylene group and n is 1-6.
  3. Flowability improving agent according to claim 1, wherein R&sub1; in the compound B is an oxypropylene group and n is 3-8.
  4. Flowability improving agent according to any one of claims 1-3, wherein Ar in the compound B is a benzene rest and R&sub2; is a phosphonate group with the formula
    where M&sub1; and M&sub2; are hydrogen ion or alkali metal ion.
  5. Flowability improving agent according to any one of claims 2-4, wherein A) is a sulphonated melamine-formaldehyde resin or a sulphonated melamine-urea-formaldehyde resin.
  6. Flowability improving agent according to any one of claims 1-5, containing 0.5-30, preferably 0.5-20% by weight of B and 99.5-70, preferably 99.5-80% by weight of A) calculated on a dry product.
  7. Flowability improving agent according to any one of claims 1-6, wherein Ar in the compound B is substituted with an alkyl group, preferably CH&sub3;, C&sub2;H&sub5; or C&sub3;H&sub7;.
  8. Process for the production of a flowability improving agent, wherein a compound B) with the general formula
    where Ar is a possibly substituted benzene group or naphtalene group, R&sub1; is an oxyethylene group;

    - CH&sub2;CH&sub2;O - or an oxypropylene group
    an oxyethylene chain or an oxypropylene chain with up to fifteen oxyethylene groups or oxypropylene groups or a combination of oxyethylene groups and oxypropylene groups to a chain where the sum of these groups is at most fifteen; the mean value n for n is 1-15 and R&sub2; is hydrogen or a phosphonate group with the formula
    where M&sub1; and M&sub2; are hydrogen ion or alkali metal ion and where R&sub2; is a group with the formula
    where M&sub2; has the above meaning and M&sub3; is
    where R&sub1;, n and Ar have the above meaning,

    is added at the production of a resin A) consisting of a sulphonated melamine-formaldehyde resin or a sulphonated melamine-urea-formaldehyde resin.
  9. Use of a flowability improving agent comprising 99.5-70% by weight, calculated on a dry product of A) a sulphonated melamine-formaldehyde resin, a sulphonated melamine-urea-formaldehyde resin or a sulphonated naphtalene-formaldehyde resin and 0.5-30% by weight of a compound B) with the general formula
    where Ar is a possibly substituted benzene group or naphtalene group, R&sub1; is an oxyethylene group;

    - CH&sub2;CH&sub2;O - or an oxypropylene group;
    an oxyethylene chain or an oxypropylene chain with up to fifteen oxyethylene groups or oxypropylene groups or a combination of oxyethylene groups and oxypropylene groups to a chain where the sum of these groups is at most fifteen; the mean value n for n is 1-15 and R&sub2; is hydrogen or a phosphonate group with the formula
    where M&sub1; and M&sub2; are hydrogen ion or alkali metal ion; as an additive to a composition containing one or more of the following products; cement, lime, gypsum, talc, chalk or titanium dioxide.
Anspruch[fr]
  1. Agent pour améliorer l'aptitude à l'écoulement, comprenant une combinaison :
    • A) d'une résine mélamine-formaldéhyde sulfonée, d'une résine mélamine-urée-formaldéhyde sulfonée ou d'une résine naphtalène-formaldéhyde sulfonée, et
    • B) d'un composé répondant à la formule générale :
      dans laquelle Ar est un groupe benzène ou un groupe naphtalène éventuellement substitué,

      R&sub1; est un groupe oxyéthylène;

      -CH&sub2;CH&sub2;O - ou un groupe oxypropylène;
      une chaîne oxyéthylène ou une chaîne oxypropylène avec jusqu'à quinze groupes oxyéthylène ou groupes oxypropylène ou une combinaison de groupes oxyéthylène et de groupes oxypropylène dans une chaîne où la somme de ces groupes est au plus quinze; la valeur moyenne n pour n est 1-15 et R&sub2; est un atome d'hydrogène ou un groupe phosphonate répondant à la formule :
      dans laquelle M&sub1; et M&sub2; sont un ion hydrogène ou un ion métal alcalin, ou dans laquelle R&sub2; est un groupe répondant à la formule :
      dans laquelle M&sub2; a la signification précédente et M&sub3; est
      dans laquelle R&sub1;, n et Ar ont la signification précédente.
  2. Agent pour améliorer l'aptitude à l'écoulement selon la revendication 1, dans lequel R&sub1; dans le constituant B) est un groupe oxyéthylène et n est 1-6.
  3. Agent pour améliorer l'aptitude à l'écoulement selon la revendication 1, dans lequel R&sub1; dans le constituant B) est un groupe oxypropylène et n est 3-8.
  4. Agent pour améliorer l'aptitude à l'écoulement selon l'une quelconque des revendications 1-3, dans lequel Ar dans le constituant B est un reste benzène et R&sub2; est un groupe phosphonate répondant à la formule :
    dans laquelle M&sub1; et M&sub2; sont un ion hydrogène ou un ion métal alcalin.
  5. Agent pour améliorer l'aptitude à l'écoulement selon l'une quelconque des revendications 2-4, dans lequel A) est une résine mélamine-formaldéhyde sulfonée ou une résine mélamine-urée-formaldéhyde sulfonée.
  6. Agent pour améliorer l'aptitude à l'écoulement selon l'une quelconque des revendications 1-5, contenant 0,5-30 %, de préférence 0,5-20 % en poids, de B et 99,5-70 %, de préférence 99,5-80 % en poids, de A) calculé pour un produit à l'état sec.
  7. Agent pour améliorer l'aptitude à l'écoulement selon l'une quelconque des revendications 1-6, dans lequel Ar dans le composé B est substitué par un groupe alkyle, de préférence CH&sub3;, C&sub2;H&sub5; ou C&sub3;H&sub7;.
  8. Procédé pour la fabrication d'un agent améliorant l'aptitude à l'écoulement, dans lequel un composé B) répondant à la formule générale :
    dans laquelle Ar est un groupe benzène ou un groupe naphtalène éventuellement substitué,

    R&sub1; est un groupe oxyéthylène;

    - CH&sub2;CH&sub2;O - ou un groupe oxypropylène;
    une chaîne oxyéthylène ou une chaîne oxypropylène avec jusqu'à quinze groupes oxyéthylène ou groupes oxypropylène ou une combinaison de groupes oxyéthylène et de groupes oxypropylène dans une chaîne où la somme de ces groupes est au plus quinze; la valeur moyenne n pour n est 1-15 et R&sub2; est un atome d'hydrogène ou un groupe phosphonate répondant à la formule :
    dans laquelle M&sub1; et M&sub2; sont un ion hydrogène ou un ion métal alcalin, et où R&sub2; est un groupe répondant à la formule :
    dans laquelle M&sub2; a la signification précédente et M&sub3; est
    dans laquelle R&sub1;, n et Ar ont la signification précédente,

    est ajouté à la production d'une résine A) constituée d'une résine mélamine-formaldéhyde sulfonée ou d'une résine mélamine-urée-formaldéhyde sulfonée.
  9. Utilisation d'un agent pour améliorer l'aptitude à l'écoulement comprenant 99,5-70 % en poids, calculé par rapport au produit à sec de A) une résine mélamine-formaldéhyde sulfonée, une résine mélamine-urée-formaldéhyde sulfonée, ou une résine naphtalène-formaldéhyde sulfonée et 0,5-30 % en poids d'un composé B) répondant à la formule générale :
    dans laquelle Ar est un groupe benzène ou un groupe naphtalène éventuellement substitué,

    R&sub1; est un groupe oxyéthylène;

    - CH&sub2;CH&sub2;O - ou un groupe oxypropylène;
    une chaîne oxyéthylène ou une chaîne oxypropylène avec jusqu'à quinze groupes oxyéthylène ou groupes oxypropylène ou une combinaison de groupes oxyéthylène et de groupes oxypropylène dans une chaîne où la somme de ces groupes est au plus quinze; la valeur moyenne n pour n est 1-15 et R&sub2; est un atome d'hydrogène ou un groupe phosphonate répondant à la formule :
    dans laquelle M&sub1; et M&sub2; sont un ion hydrogène ou un ion métal alcalin; comme additif à une composition contenant un ou plusieurs des produits suivants : ciment, chaux, gypse, talc, craie ou dioxyde de titane.






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