WO1998049220A1

WO1998049220A1 - Method for preparing functionalised polyorganosiloxane by hydrosilylation and use of a composition containing at least a polyorganosiloxane for softening a textile material and making it hydrophile and discoloration-proof

Info

Publication number: WO1998049220A1
Application number: PCT/FR1998/000864
Authority: WO
Inventors: Gérard Mignani; Philippe Karrer
Original assignee: Rhodia Chimie
Priority date: 1997-04-30
Filing date: 1998-04-29
Publication date: 1998-11-05
Also published as: FR2762847B1; AU7537298A; FR2762847A1

Abstract

The invention concerns a method for preparing functionalised polyorganosiloxanes by carrying out successive hydrosilylation of two types of monomers (I and II) with a hydrogenosiloxane comprising identical or different structural units of the general formula (III): RaHbSiO 4-(a+b)/2 in which: (i) a = 0, 1 or 2, b = 0 or 1, a+b = ≤2; (ii) the symbols R represent monovalent hydrocarbon radicals. The first hydrosilylation is carried out with a first type of monomer of formula (I): CH2=CH-(CH2)n-(OCH2CH2)α(OCH2CHCH3)β-OR1. The second hydrosilylation is carried out with a second type of monomer (II) of the secondary or tertiary congested amine type, preferably a congested piperidinyl group. The invention also concerns the use of compositions containing at least one polyorganosiloxane obtained by the method of preparation, for conditioning textile materials providing a soft feel, good hydrophily and proof to discoloration.

Description

PROCESS FOR THE PREPARATION OF FUNCTIONALIZED POLYORGANOSILOXANE

BY HYDROSILYLATION AND USE OF A COMPOSITION COMPRISING

AT LEAST ONE POLYORGANOSILOXANE TO SOFTEN AND RENDER

NON-YELLOWING AND HYDROPHILIC A TEXTILE MATERIAL

The present invention relates to a new process for the preparation of polyorganosiloxanes by hydrosilylation and their use in compositions for the conditioning of textile materials providing the textile fiber with good hydrophilicity, an absence of yellowing and a pleasant hand feel, that is to say ie softness properties. The invention also relates to a clear, non-colored textile conditioning agent, and a textile conditioning composition providing the textile fiber treated with the properties mentioned above.

The literature describes compositions and methods for conditioning textile materials.

US-A-4409 267 describes the use of a mixed polyorganosiloxane carrying, on the one hand a primary or secondary amine function (s) substituted for example by residues containing a OH or O-alkyl group and, on the other hand, alkylene polyoxide function (s) as additive of a composition for the treatment of textile materials.

EP-546 231 describes the use of a polyorganosiloxane carrying unit (s) of formula: Si - (CH ₂ ) _y - (OCH ₂ ) _y '- CH (OH) CH ₂ - N (CH ₂ CH ₂ OH ) 2 where y is between 2 and 8 and y 'is equal to 0 or 1.

EP-A-0 459 822 describes homogeneous and transparent detergent compositions comprising a polyorganosiloxane with secondary or tertiary amine function (s) substituted for example by residues containing an OH group, the said group silicone being used in mixture with a softening agent based on a quaternary ammonium salt.

These compositions and methods of the prior art are not entirely satisfactory in providing the treated materials with non-yellowing, softness and hydrophilic properties. In addition, the processes used to prepare polyorganosiloxanes suitable for use in textile packaging lead to the production of polyorganosiloxanes having characteristics of clarity, coloring and turbidity which limit their field of use, in particular for the treatment of materials for which it is desired to preserve a very high whiteness index.

Now, the Applicant has developed a new process for the preparation of polyorganosiloxanes which does not have the drawbacks of the prior art.

An advantage of the process according to the present invention is that it makes it possible to obtain polyorganosiloxanes by hydrosilylation reactions based on inexpensive reagents or chemical molecules which are easy to handle.

A second advantage of the method according to the present invention comes from the fact that it can be implemented industrially without difficulty. It makes it possible, in particular, to prepare compositions based on polyorganosiloxane (s) according to the invention which are stable on storage.

In addition, another advantage of the preparation process according to the invention makes it possible to directly obtain limpid, transparent polyorganosiloxanes, of coloring less than 20 Hazen and of very low turbidity of the order of 5 NTU, without requiring bleaching steps. and / or purification which is not economically and industrially viable.

Another advantage of the process according to the present invention comes from the easy manufacture of a textile conditioning composition containing the polyorganosiloxane according to the invention for its application to the materials to be treated.

It has therefore now been found, and this is what is the subject of the present invention, a new process for the preparation of linear, cyclic or three-dimensional functionalized polyorganosiloxanes, carrying, among other things, substituted amine function (s) ( s), of coloring less than 20 Hazen and of turbidity less than 5 NTU and, of molecular mass of the order of 5,000 to 500,000 grams, preferably of the order of 10,000 to 300,000 grams, by 2 successive stages hydrosilylation, of a permutable order, of a first type of monomer (I), identical or different, and of a second type of monomer (II), identical or different, with a hydrogenosiloxane comprising identical or different units from general formula (III): R _a H _b If OTL (III) in which :

(i) a = 0, 1 or 2 b = 0 or 1 a + b ≤ 2 (ii) the symbols R are identical and / or different and represent a monovalent hydrocarbon radical chosen from linear or branched alkyl radicals having from 1 to 4 carbon atoms, linear or branched aikoxy radicals having from 1 to 4 carbon atoms, a phenyl radical,

(1) one of the two hydrosilylation steps being carried out with the first type of monomer of formula (I): CH ₂ = CH - (CH ₂ ) _n - (OCH2CH ₂ ) _α (OCH ₂ CHCH ₃ ) β - OR ² in which:

- 0 <n <8, preferably n = 0, - α and β are independent integer or fractional values such as α

> 1, β> 0 and, 100 x a I (α + β)> 50.

- R ² is a hydrogen atom, COR ³ or a linear alkyl radical and,

- R ³ is a hydrogen atom or a linear alkyl radical.

(2) the other hydrosilylation step being carried out with the second type of monomer

(II), having a hydrosilylable motif, of the hindered secondary or tertiary amine type;

(3) the two hydrosilylation stages taking place in the presence of an amount of 10 to 1000 ppm, preferably 50 to 200 ppm of hydrosilylation catalytic composition relative to the total mass of the polyorganosiloxane obtained;

(4) the reaction medium being heated to a temperature between 25 ° C and 200 ° C, and preferably between 60 ° C and 120 ° C; and

(5) optional, the polyorganosiloxane obtained containing substituted amino functions and polyether functions being finally devolatilized.

As regards devolatilization (5), this step is carried out when the reaction medium contains a solvent and / or when an excess of monomer is used for the second hydrosilylation step. This devolatilization does not affect the stability of the polyorganosiloxane. The monomers of type (I) are introduced over a period of between 0 and 24 hours, preferably between 0.5 and 2 hours. Similarly, the monomers of type (II) are introduced over a period of between 0 and 24 hours, preferably between 0.5 and 2 hours. For the first hydrosilylation, the best results, in terms of obtaining the final product, are observed when the hydrogenosiloxane is poured simultaneously with the hydrosilated monomer in the first step.

The process according to the invention can advantageously be carried out in bulk or in the presence of a volatile organic solvent. Many solvents can be used, such as isopropanol, toluene, xylene, octamethyltetrasiloxane, cyclohexane or hexane, etc. The reaction medium can also contain a buffering agent consisting in particular of an alkaline salt of 'a carboxylic acid such as for example sodium acetate.

Many types of homogeneous or heterogeneous catalytic compositions can be used in the process according to the invention. The most well-known catalytic compositions contain metals, such as platinum, rhodium, cobalt or palladium. Specific examples of such catalytic compositions are the platinum halides and rhodium halides, for example H2PtClg _ι CI2, (Rr.CI3.xH2O) platinum complexes with siloxanes having unsaturated groups, platinum complexes with olefins and cationic platinum complexes with nitriles as ligands.

In general, the catalytic compositions used in the process of the invention are homogeneous catalytic compositions, i.e., said compositions are dissolved in the reaction medium. One of the most used is the catalytic composition of Karstedt described in particular in US Patent 3,775,452.

However, the heterogeneous catalytic compositions are also suitable for the process of the invention. In this regard, reference will be made to the various heterogeneous catalytic compositions described in our patent application No. 9607272 filed on June 12, 1996 in France. In this case, the heterogeneous catalytic composition can be recovered then reused again, without requiring regeneration, with or without washing, and without there being any noticeable drop in activity of its performance.

According to an advantageous variant of the process according to the invention, the hydrosilylation steps are carried out in the following preferential and precise order: (1) the first hydrosilylation is carried out with the type (I) momomer, then (2) the second hydrosilylation is carried out with the type (II) monomer.

In this case, the molar quantity of monomer (I) is equal to the molar quantity (or number) of ≡SiH groups which it is desired to functionalize with the monomer (I); that is to say, it is not necessary to introduce the monomer (I) in molar excess. And, the molar quantity of monomer (II) is equal to the molar quantity (or number) of ≡SiH groups remaining after hydrosilylation of the type (I) monomer, optionally supplemented with 10 to 30% molar excess.

Preferably, the symbols R of the hydrogenosiloxane are alkyl, methoxy and / or hydroxy radicals, and more particularly methyl radicals. The hydrogenosiloxane used in the process is prepared, in a manner known per se, either by redistribution or redistribution-condensation reaction. For example, hydrogenosiloxane is prepared by redistribution between hexamethyldisiloxane, octamethylcyclotetrasiloxane and polymethylhydrogenosiloxane.

According to a first preferred embodiment of the invention, at least one of the monomers of type (I) is such that 1 <a≤ 80, 0 <β≤ 60 and 100 x α / (α + β)>80; and more particularly, at least one of the monomers of type (I) is such that α is between 8 and 25 and β is between 0 and 7. In addition, very favorable results are obtained when at least one or all of the monomers of type (I) are such that n is equal to 1.

According to a second preferred embodiment of the process of the invention, the monomers of type (II) used to prepare the polyorganosiloxanes are monomers having a hydrosilylable unit and at least one sterically hindered piperidinyl group chosen from:

or

For the remains of formula (IV)

* R is a radical chosen from linear or branched alkyl radicals having 1 to 3 carbon atoms and a hydrogen atom,

* R ⁴ is a divalent hydrocarbon radical chosen from:

* linear or branched alkylene radicals having 2 to 18 carbon atoms;

* alkylene-carbonyl radicals, the linear or branched alkylene part of which contains 2 to 20 carbon atoms;

* alkylene-cyclohexylene radicals, the linear or branched alkylene part of which comprises 2 to 12 carbon atoms and the cyclo-hexylene part comprises an OH group and optionally 1 or 2 alkyl radicals having 1 to 4 carbon atoms; * the radicals of formula -R ⁷ - O - R ⁷ in which the identical or different radicals R ⁷ represent alkylene radicals having 1 to 12 carbon atoms;

* the radicals of formula -R ⁷ - O - R ⁷ in which the radicals R ⁷ have the meanings indicated above and one of them or both are substituted by one or two group (s) -OH;

* the radicals of formula -R ⁷ - COO - R ⁷ in which the radicals R ⁷ have the meanings indicated above;

* the radicals of formula -R ⁸ -O -R ⁹ - O-CO-R ⁸ in which the radicals R ⁸ and R ^{9 which are} identical or different, represent alkylene radicals having 2 to 12 carbon atoms and the radical R ⁹ is optionally substituted with a hydroxyl radical;

* U represents -O- or -NR ¹⁰ -, R ¹⁰ being a radical chosen from a hydrogen atom, a linear or branched alkyl radical containing 1 to 6 carbon atoms and a divalent radical of formula:

in which R ⁴ has the meaning indicated above, R ⁵ and R ⁶ have the meanings indicated below and R ¹¹ represents a divalent alkylene radical, linear or branched, having from 1 to 12 carbon atoms, one of the valential bonds (that of R ¹¹ ) being linked to the atom of -NR ¹⁰ -, the other (that of

R ⁴ ) being linked to a silicon atom;

* the radicals R ⁵ are identical or different, chosen from linear or branched alkyl radicals having 1 to 3 carbon atoms and the phenyl radical; * the radical R ⁶ represents a hydrogen radical or the radical R ⁵ or Ov For the remains of formula (V):

* R ' ⁴ is chosen from a trivalent group of formula:

- (CH ₂ ) CH ^co where m represents a number from 2 to 20, and a trivalent group of formula:

where p represents a number from 2 to 20;

* U 'represents -O- or NR ¹² -, R ¹² being a radical chosen from a hydrogen atom, a linear or branched alkyl radical containing 1 to 6 carbon atoms;

* R ⁵ and R ⁶ have the same meanings as those given in connection with formula (IV).

According to a particularly preferred variant, the units of types (II) are vinyl or allylic units containing at least one hydrocarbon ring in which is included a nitrogen atom forming a hindered amine of HALS type, for example, of formula:

The polyorganosiloxanes obtained from the process of the invention constitute excellent textile conditioning agents. These polyorganosiloxanes are clear, of almost zero coloration, less than 20 Hazen and also of almost zero turbidity, less than 5 NTU and, as illustrated by the example and the tests below, have improved properties for textile packaging.

Generally, the levels of the units of the polyorganosiloxane (s) obtained and, specially adapted to constitute the textile conditioning agent, are as follows:

(1) the rate of Q and T units is less than or equal to 10% by mole;

(2) the level of units of formula (III) in which the silicon atom carries a functional residue resulting from the hydrosilylation of the monomer of type (I) is less than or equal to 20% by mole; and

(3) the level of units of formula (III) in which the silicon atom carries a functional residue resulting from the hydrosilylation of the type (II) monomer is less than or equal to 20% by mole.

This (s) polyorganosiloxane (s) adapted (s) is (are) of medium formula

-

in which :

(1 ') the symbols R are the same or different and have the meanings given in claim 1;

(2 ′) the symbols X are identical or different and correspond to functional residues resulting from the hydrosilylation of the monomer of type (I),

(3 ') the symbols V are identical or different and correspond to functional residues resulting from the hydrosilylation of the monomer of type (II),

(4 ') the symbols Z are identical or different and represent R, X and / or V,

(5 ') x, y, z and w are totally independent decimal values, chosen respecting the rates of the above reasons, given and such that: - 10.4 <x + y + z + w <3000, - 10 < x <2500, preferably 100 <x <2000,

- 0.2 <y <450, preferably 2 <y <20,

- 0.2 <z <450, preferably 0.8 <z <20 and

- 0 <w <300, preferably 0 <w <20 The textile conditioning composition containing the textile conditioning agent can be prepared in many forms: liquid, gaseous or solid. In the case of a liquid preparation of the composition, it will advantageously be aqueous, either in the form of a solution, dispersion or emulsion.

Preferably, the textile conditioning composition is prepared in the form of an aqueous emulsion. However, this composition can also be used in solution in an inert organic solvent. This solvent can be for example toluene or xylene.

The aqueous emulsions are generally based on a mixture of the polyorganosiloxane obtained (= oil) and water, and are prepared according to the conventional methods well known to those skilled in the art using surfactants. For example, the emulsions can be made by the so-called direct methods or by inversion. They are easy to make and do not require the use of high-speed agitation equipment. Apparatus at normal stirring speed may be used.

In general, the aqueous emulsions prepared in the context of the invention preferably contain between 20 and 90% by weight of water relative to the total mass of the constituents of the emulsion. For better application, the emulsions prepared are preferably diluted to contain between 95 and 99.5% by weight of water relative to the total weight of the emulsion. These emulsions, diluted or not, prove to be very stable at room temperature.

The application of the textile conditioning composition according to the invention to the materials to be treated can be carried out in very diverse forms. The applications can be carried out by immersion, coating, spraying, printing, "padding" (padding in English), coating with a doctor blade or by any other existing means. For example, when the fabric is treated with an aqueous textile conditioning composition according to the invention, said fabric is subjected to a heat treatment to rapidly expel water in the form of vapor.

The quantity of polyorganosiloxane deposited on the material to be treated varies according to the constitution and the manufacture of said material. The applications of the compositions and in particular aqueous emulsions on the treated materials are carried out so that the increase in weight of the treated material does not exceed 0.1 to 20% by weight relative to the weight of the material before treatment. In general, the best results were observed with an amount of polyorganosiloxane of between 0.1 and 2% by weight relative to the weight of the material to be treated.

Whatever the constitution chosen for the textile conditioning composition, the conditioning process can be carried out on any natural or synthetic material in woven, non-woven or knitted form.

The fibers of these materials can in particular consist entirely or based on keratin, cotton, linen, wool, viscose, rayon, hemp, silk, polypropylene, polyethylene, polyester, polyurethane, polyamide, cellulose acetate or a mixture of these. .

EXAMPLES

The example below illustrates the preparation of polyorganosiloxanes with sterically hindered pyperidinyl function (s) and with polyether function (s) for their use in the process according to the invention.

The example relates to the synthesis of a non-hydrolyzable polyorganosiloxane di-substituted with polyether and tetramethylpiperidine functions of formula:

a) Procedure

The following reagents are introduced into a reactor equipped with mechanical stirring, a temperature probe, a dropping funnel, a vertical cooler, a sample-taking opening:

• 50 g of isopropanol and, • 2 g of carbon black 2S supported on platinum at 2.5% by mass dried 17 h at

105 ° C under 40 mm Hg.

Stirring is started and the reaction medium is heated to 83 ° C. The headspace of the reactor is oxygenated by a circulation of nitrogen. A mixture is then poured over a period of 35 minutes consisting of: • 66.7 g (0.109 mol) of allylpolyether (product referenced 7164-82 from the company

Texaco) of structure:

^^ C CH ₂ C l, O), ₀ - (CHz CHCH ₃ 0) ₂ -H

• 500 g of polydimethyl siloxane oil with SiH units and with 0.456 mol of Si-H function per kg of oil (ie 0.228 mol of Si-H function), the structure of which is as follows:

Me ₃ SiO- (SiOMe ₂ ) ₂₀₀ - (SiOMe) ₇ -SiMe ₃

• and 250 g of isopropanol.

The conversion rate of the SiH functions is 47.8% after 2 hours and 45 minutes since the start of the casting, ie a total conversion of the allylpolyether functions.

We then introduce into the environment:

• 2 g of carbon black 2S supported on platinum at 2.5% by mass dried for 17 hours at 105 ° C under 40 mm Hg and

• 29.6 g (0.15 mol) of allyloxy 2,2,6,6-tetramethyipiperidinyl. The mixture is left stirring at the same temperature (83 ° C.) for approximately

12 hours ; the conversion of the Si-H functions is total.

The medium is then filtered to remove the carbon black, a first time on a cellulose cardboard membrane and a second time on a 0.5 μm Teflon membrane. The filtrate is then devolatilized (160 ° C., 5 mm Hg, 2 hours) to remove the solvent and the excess of allyloxytetramethylpiperidinyl and 540 g of di-substituted polyorganosiloxane of formula:

) - (CH ₂ CH ₂ O) ₁₀ - (CH ₂ CHCH _j 0) ₂ -H

b) Characteristics

The characteristics of the polyorganosiloxane obtained are - viscosity: 4075 mPa.s at 25.8 ° C.

- [amine] = 0.1864 mol / kg of oil.

- coloring: less than 20 Hazen.

- turbidity: less than 5 NTU. The coloration of the functionalized polyorganosiloxane obtained is measured using a "liquid tester LTMT" device from Dr. Lange using two rays for the measurement in transmission.

The turbidity of the functionalized polyorganosiloxane is measured using a Hack turbidimeter by light dispersion (measurement by ratio).

The structure of the polyorganosiloxane was confirmed by nuclear magnetic resonance analysis and size exclusion chromatography.

TESTS

The polyorganosiloxane prepared above and a silicone oil of the prior art

(C2) are tested in application in the form of an aqueous emulsion; the tests relate to hydrophilicity, white index and touch assessment measurements.

The properties of the fabrics treated with the oil emulsion in accordance with the present invention were compared, on the one hand to those of an untreated fabric C1, and on the other hand with those of fabrics treated respectively by the silicone compounds C2.

Compound C2 is a silicone oil marketed under the name Rhodorsil® 21650 by the company Rhône-Poulenc of general formula in which x = 1400 and y =:

The emulsions E1 and E2 were prepared using the "phase inversion technique".

The emulsion E1 is prepared with the polyorganosiloxane prepared in accordance with the invention and has the following composition (by weight): - 20% of silicone oil, - 10% of surfactant C13 EO 6, - 0.2% of acetic acid glacial, - 0.1% sodium sulfate,

- 2% of the monoglutyl ether of diethylene glycol, and

- 67.7% water.

The emulsion E2 prepared with the oil C2 has the following composition (by weight): - 69.75% of water,

- 6.45% of Rhodasurf BC-610 marketed by the company Rhône-Poulenc,

- 2.55% of Rhodasurf BC-420 marketed by the company Rhône-Poulenc,

- 0.05% sodium acetate, - 1.20% acetic acid, and - 20% silicone oil.

The properties of the emulsions E1 and E2 were evaluated on the basis of the following three measurements: measurement of non-yellowing, measurement of hydrophilicity and test of touch. These evaluations were carried out on textiles treated with 1% by weight of silicone oil.

° Non-yellowing measure: The fabric used is a white polyester / cotton (50/50) fabric. The heat treatment after application is 9 minutes at 150 ° C.

The evaluation of the yellowing is carried out by the measurement, well known in the textile industry, of the degree of white E313 carried out on the spectrophotocolorimeter ACS Sensor II marketed by the company Datacolor with the use of the illuminant D65 reproducing the daylight .

Measuring the percentage of reflectance shows that there is no yellowing (-) for the fabric treated with E1. On the other hand, yellowing is important for the untreated tissue (++) and for the tissue treated with E2 (+).

° Touch test: The fabric used is a polyester / cotton terry cloth (50/50). After application, the fabric is dried in ambient air for 24 hours. After a heat treatment at 150 ° C for 1 minute 30, the fabric is placed in conditioning for 24 hours (23 ± 2 ° C, 50% ± 5 relative humidity). The softness is evaluated by different testers who are asked to classify the samples from the roughest to the softest. The results are expressed either in soft pleasant touch (AD) or in non-pleasant touch, without softness (NAD).

The fabric treated with E1 is pleasantly soft to the touch. Hydrophilicity measurement:

The fabric used is a polyester / cotton fabric (50/50), taffeta weave.

The heat treatment after application is 5 minutes at 170 ° C. The tissue is left at room temperature for 24 hours. The hydrophilicity measurements are made by the Tegewa drop test which measures the absorption time of a drop of water on the surface of the textile.

For an untreated fabric: 10 seconds

For a fabric treated with E1 emulsion: 8 seconds.

For a fabric treated with E2 emulsion: more than 60 seconds.

Claims

REVENPIÇATIQNS

1. Process for the preparation of linear, cyclic or three-dimensional functionalized polyorganosiloxanes, carrying, inter alia, substituted amine function (s), coloring less than 20 Hazen and turbidity less than 5 NTU and, molecular weight of on the order of 5000 to 500,000 grams, preferably on the order of 10,000 to 300,000 grams, by 2 successive hydrosilylation stages, the order of which is permutable, of a first type of monomer (I), identical or different, then a second type of monomer D, identical or different, with a hydrogenosiloxane comprising identical or different units of general formula (III):

R _a H _b If O ^ (III) in which: (i) a = 0, 1 or 2 b = 0 or 1 a + b <2

(ii) the symbols R are identical and / or different and represent a monovalent hydrocarbon radical chosen from linear or branched alkyl radicals having from 1 to 4 carbon atoms, linear or branched aikoxy radicals having from 1 to 4 carbon atoms, a phenyl radical.

(1) one of the hydrosilylation stages being carried out with the first type of monomer (I) of formula (I): CH ₂ = CH - (CH ₂ ) _n - (OCH2CH2) _α (OCH ₂ CHCH ₃ ) β - OR ¹ in which:

- 0 <n <8, preferably n = 0,

- a and β are independent decimal values such as a ≥ 1, β> 0 and, 100 xa I (α + β)> 50. - R ¹ is a hydrogen atom, COR ² or a linear alkyl radical and,

- R ² is a hydrogen atom or a linear alkyl radical.

(2) the other hydrosilylation step being carried out with the second type of monomer (II), having a hydrosilylable unit, of hindered secondary or tertiary amine type; (3) the two hydrosilylation stages taking place in the presence of an amount of 10 to 1000 ppm, preferably 50 to 200 ppm of hydrosilylation catalytic composition relative to the total mass of the polyorganosiloxane obtained;

2. Preparation process according to claim 1, characterized in that the hydrogenosiloxane is poured simultaneously with the monomer to be hydrosiled in the first step.

3. Preparation process according to any one of claims 1 or 2, characterized in that the first hydrosilylation is carried out with the monomer of type (I) then the second hydrosilylation is carried out with the monomer of type (II).

4. Preparation process according to any one of claims 1 to 3, characterized in that the first hydrosilylation and the second hydrosilylation take place in the same reaction medium without an intermediate step to isolate the product resulting from the first hydrosilylation.

5. Preparation process according to any one of claims 1 and 4, characterized in that the monomers of type (I) are introduced over a period of between 0 and 24 hours, preferably between 0.5 and 2 hours.

6. Preparation process according to any one of claims 1 to 5, characterized in that the monomers of type (II) are introduced over a period of between 0 and 24 hours, preferably between 0.5 and 2 hours.

7. Preparation process according to any one of the preceding claims, characterized in that the symbols R of the hydrogenosiloxane are alkyl, methoxy and / or hydroxy radicals, and preferably methyl radicals.

8. Preparation process according to any one of the preceding claims, characterized in that at least one of the monomers of type (I) is such that: 1 <a≤ 80, 0 <β <60 and 100 x α / ( α + β) ≥ 80.

9. Preparation process according to the preceding claim, characterized in that at least one of the monomers of type (I) is such that α is between 8 and 25 and β is between 0 and 7.

10. Preparation process according to any one of the preceding claims, characterized in that at least one of the monomers of type (I) is such that n is equal to 1.

11. Preparation process according to one of the preceding claims, characterized in that the monomers of type (II) are monomers having a hydrosilylable unit and at least one sterically hindered piperidinyl group chosen from:

or

For the remains of formula (IV):

* R ^ is a radical chosen from linear or branched alkyl radicals having 1 to 3 carbon atoms and a hydrogen atom, * R ⁴ is a divalent hydrocarbon radical chosen from:

* linear or branched alkylene radicals having 2 to 18 carbon atoms;

»The radicals of formula -R ⁷ - COO - R ⁷ in which the radicals R ⁷ have the meanings indicated above;

in which R ⁴ has the meaning indicated above, R ⁵ and R ⁶ have the meanings indicated below and R ¹¹ represents a divalent alkylene radical, linear or branched, having from 1 to 12 carbon atoms, one of the valential bonds (that of R ¹ ) being connected to the atom of -NR ¹⁰ -, the other (that of R ⁴ ) being connected to a atom of silicon; * the radicals R ⁵ are identical or different, chosen from linear or branched alkyl radicals having 1 to 3 carbon atoms and the phenyl radical;

* the radical R ⁶ represents a hydrogen radical or the radical R ⁵ or Ov For the residues of formula (V):

* R ' ⁴ is chosen from a trivalent group of formula:

where p represents a number from 2 to 20;

12. Textile conditioning agent, clear, coloration less than 20 Hazen and turbidity less than 5 NTU consisting of at least one polyorganosiloxane capable of being obtained by the process according to one of the preceding claims.

13. Textile conditioning agent according to the preceding claim, characterized in that the levels of the polyorganosiloxane units are as follows:

(1) the rate of Q and T units is less than or equal to 10% by mole;

(2) the level of units of formula (III) in which the silicon atom carries a functional residue resulting from the hydrosilylation of the type monomer (0 is less than or equal to 20% by mole; and

(3) the level of units of formula (III) in which the silicon atom carries a functional residue resulting from the hydrosilylation of the type monomer (10 is less than or equal to 20% by mole;

14. Textile conditioning agent according to claim 12 or 13, characterized in that the pol

in watercolors:

(4 ') the symbols Z are identical or different and represent R, X and / or V,

(5 ') x, y, z and w are totally independent decimal values chosen while respecting the pattern rates of (1), (2) and (3) of claim 11 and such that:

- 10.4 <x + y + z + w <3000 - 10 <x <2500

- 0.2 <y <450

- 0.2 <z <450

- 0 <w <300

15. Textile conditioning composition comprising a textile conditioning agent according to any one of claims 12, 13 or 14, characterized in that said composition is in liquid form, preferably in the form of an aqueous emulsion.

16. Use of a composition containing at least one polyorganosiloxane capable of being obtained from the process according to one of claims 1 to 11 for conditioning textile materials providing a pleasant feel, good hydrophilicity and an absence of yellowing to the said textile materials, in which the textile materials are contacted with said composition.

17. Use according to the preceding claim, characterized in that the packaging is carried out on a woven, knitted or non-woven material, said material being based on cotton, polyester, polyamide, viscose, polyacrylate, wool, and / or acetate cellulose.

18. Use according to the preceding claim, characterized in that the amount of polyorganosiloxane deposited on the treated textile material corresponds to an amount between 0.1 and 2% by weight relative to the weight of the treated dry textile material.

19. Textile material with pleasant feel, high hydrophilicity and non-yellowing treated with a polyorganosiloxane capable of being obtained by the process according to any one of claims 1 to 11.