CA1166265A - Ester containing silylated polyethers - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

Novel silylated polyethers having the general formula are provided herein. At least one R is selected from the group consisting of in which R is linked to the polyether through an ester radical, the remain-ing R groups are selected from hydrocarbonoxy radicals having up to 18 carbon atoms, hydroxyl radicals or a radical of the formula wherein R1, when present is a divalent hydrocarbon radical selected from the group consisting of -(CH2)y, wherein y is a number from 1 to 8, -CH=CH-, or a cyclic hydrocarbon radical selected from the group consisting of C6H4, C6H8, C6H10 and C10H6. A is a silicon-containing radical selected from the group having the formulas wherein R which may be the same or different is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, R is a divalent hydrocarbon radical having from 1 to 18 carbon atoms, a is a number of from 0 to 4, b, c and d are each numbers of from 0 to 1, the sum of b, c and d must be 1 when A is a monovalent radical and when b, c or d arc 0, then R must be hydroxyl or a hydrocarbonoxy radical or a radical of the formula

Description

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The present invention relates to silylated polyethers. More particularly, this invention relates to a process ~or preparing silylated polyethers. Also, this invention relates to textile materials coated with silylated polyethers and to a process for coating the same.
Heretofore, textile materials have been treated with compositions containing a hydroxyl-terminated organopolysiloxane, a crosslinking agent and a catalyst to impart a soft, silky, durable hand thereto. (See United States Patents Nos. 3,876,459 to Burrill and 3,770,489 to Richardson.) Although treatment with these organopolysiloxanes has been very effective for the intended purpose, it has also imparted certain undes;rable properties to the treated materials. For example, textile materials treated with organopolysiloxanes tend to soil more readily. Moreover, organopolysiloxanes have a tendency to impart hydrophobic properties to textile materials treated therewith, which in turn decreases the comfort of the material. Furthermore, organopolysiloxanes are generally applied to textile materials in the form of emulsions and these emulsions have a tendency to separate during application, thereby resulting in a non-uniform coating. When these coated textile materials are subjected to further treatment, e.g., dyeing or printing, the uneven distribution of organopolysiloxanes on the surface of the textile materials interferes with the print and dye quality of the material. Another disadvantage of organopolysiloxanes is that they generally require more than one component, and once the components have been mixed, the resultant composition is of limited stabili~y.
Silicon-containing materials which have been used to impart soil-repellent and soil-release properties to textile materials are des-cribed in United States Patents Nos. 3,716,517 and 3,716,518 to Pittman et al. These silicon-containing materials are prepared by copolymeri~ing at least one monomer capable of imparting oleophobic properties with at least one monomer capable of imparting hydrophilic properties. The oleo-phobic monomer is a silane which contains a terminal perfluoroalkyl group oE from 3 to 1~ perfluorinated carbon atoms. The hydrophilic monomer ls a silane which contains two or more alkylene oxide groups in which th~
alkylene groups contain from 2 to 6 carbon atoms. These hydrophilic monomers are prepared by converting a monoetherified polyalkyleneoxy glycol to the corresponding allyl ether by reacting it with allyl bromide in the presence of a base and thereafter reacting the intermediate reaction pro-duct with a silane containing hydrogen in the presence of a platinum catalyst. Where it is desired to produce monomers containing an ester linkage, the monoetherified polyethyleneoxy glycol is esterified with acryloyl chloride and then a hydrogen-containing silane and platinum cata-lyst is added to the resultant intermediate.
In preparing the hydrophilic monomers described above, one essen-tial ingredient is terminally unsaturated polyethers which are not readily available in commercial quantities. These terminally unsatured polyethers may be prepared by reacting monoetherified polyalkyleneoxy glycols with allyl chloride. Furthermore, the si]icon compounds described by Pittman et al contain an ester group.
Therefore, it is an object of one aspect of this invention to provide silylated polyethers.
An object of another aspect of this invention is to provide silylated polyethers which may be applied to textile materials to impart a soft silky hand and resistance to soil redeposition.
An object of still another aspect of this invention is to pro-vide silylated polyethers which may be applied to textile materials to impart hydrophilic properties thereto.
An object of a further aspect of this invention i5 to provide silylated polyethers which are water soluble and will not separate before z~

and/or during application to textile materials.
An object of a still further i~speet of this invention is to pro-vide a single component, water soluble, stable silicon-containing composl-. . ~-tion for treating textile materials. ~~

In accordance with a broad aspeet of this invention, silylated polyethers are provided having the general formula

2 (Cn H2n1X R Ab 1' [CH (OCn~2~)x R Ac] a CH2 ( Cn EI2n J x R Ad wherein at least on R is selected from the group consisting of O O
~1 11 -Oc-Rl~ - o_ , _ in which the radicals are linked to the polyether through an ester and the remaining R groups are selected from hydrocarbonoxy radicals having up ~p 18 carbon a~oms, hydroxyl radicals~or a radical of the formula O O ' ' -OC-Rl - C-O-H wherein R , when present , .. . . . . . .
is a divalent hydroear~on radieal seleeted from the group eonsisting of ....~
-(CH2) , wherein y is a number from l to 8, -CH=CH-, or a eyelie radieal seleeted from the group eonsisting of C6H4, C6H8 and CloH6; A is a silieon-eontaining radieal seleeted from the group eonsisting of eationie or :.
anionie radieals of the formula .. ~ 3 . Re R3-si(oR )3-e ~2 Ie R Si 3 e wherein R2 which ~ay be the same or differen~, is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, R3 is a divalent hydrocarbon ..

~ 3 a -radical having from 1 to 18 carbon atoms, a is a number of from O to 4, b, c and d are each numbers of from O to 1, the sum of b, c and d must be at least l, and when b, c or d are 0, then R must be a hydroxyl or hydro-~ carbonoxy radical or a radical of the formula ---- O O
Il ..
- -O C Rl C OH
e is a number of from O to 2, n is 2, 3 or 4, and x is a number of at le~st l and up to 600, preferably from lO to 250.
-- These silylated polyethers may be applied to textile materials to form a 10: hydrophilic coating thereon.
The silylated polyethers of aspects of thls invention contain diester linkages.
Therefore, one of the advantages of aspects of this invention -is that the sil~lated polyethers of this invention use materials which are readily available, e.g., polyoxyalkylene glycols and haloalkyl silanes.~
Another advantage of the silylated polyethers of aspects of this invention is that these silylated polyethers will crosslink to form hydrophilic coatings on textile materials treated therewith. The hydrophilic property improves the comfort of textile mater-.als by wicking away body perspiration. Furthermore, the silylated polyethers of aspects of this invention impart softness to textile materials treated therewith which offset the harsh hand imparted to textile materials treated with amino-plast resins. Also, it has been found that the silylated polyethers of aspects of this invention will extend the aminoplast resins and in certain applications ~ay replace the aminoplast resins.
By a variant thereof, A is a radical of the ormula -C3H6Si(OCH3)3.
By another specific embodiment, the silylated polyether has the formula r~

3 b ~

o o - :
C~2--(0C3~ X(OC2H,~ ~ C(CH2)2 C oC3~6Si(oCH3)3 ' - l o :~ ,n CH - (OC H6) (OC2H4)X ~ C(CH2)2 . 3 6 . 3 3 ' I ; O O
- , ~ !
2 3 6 x( 2~4~x C(CH2~2 C oC3H6Si(oC~

in whlch x is a number of from 1 to 600.
lO , - By another aspect of this invention, a process is provided for preparing silylated polyethers.of the general formula CH2(OcnH2n)x R Ab [CH ~ CnH2n ) x R Ac ] a cl~2(0CnH2~)X R Ad .. . . . . .
in which at least one R is a radical of the formula O O
ll ll -OC-Rl_c_o in which the radlcal is linked to the polyether through an ester linkage and the remaining R groups are selected from the group consisting of hydroxyl, hydrocarbonoxy radicals llaving up to 18 carbon atoms and a radi-cal of the formula O O
l wherein R , when present O-C-R -C OH,

4 -' ~;

is a divalent hydrocarbon radical selected from the group consisting of (-CH2) , wherein y is a number from l to 8, -CH=CH- and a cyclic radical .
selected from the group consisting of C6H4, C6H8, C6Hlo and CloH6; A is a silicon-containing radical selected from the formulas .

-R3-si~oR2)3 e .. ._ . ' R2 -R3-Sio3_e _ 2 . -- . _ iD which R is a monovalent hydrocarbon radical havinc from i to 18 carbon atoms, R is a divalent hydrocarbon radical having from 1 to 18 carbon atomsl a is a number of from O to 4, b, c and d are each numbers of from O to 1 and the sum of b, c and d must be at least 1 and when b, c or d are 0, then R is selected fro~ the group consisting of a hydroxyl, a hydrocar-bonoxy radical and a radical of the formula O O
' -OC-R - C -OH, _.

e is a number of from O to 2, n is 2, 3 or 4, and-x is a number of at least 1 and up to 600, which process comprises: reacting an oxyalkylene glycol with a compound selected from the group consisting of a dicarboxylic acid and a cyclic anhydride thereof at a temperature of from 80 to 185C.; and thereafter reacting the resultant product with a haloalkylalkoxysilane having from 1 to 3 alkoxy groups linked to the silicon atom at a temperature of from 50 to 185C.

5 -s By a variant of such process, the oxyalkylene glycols are represented by the formula .
2 ( n 2n ) x [CH ( CnH 2n ) x OG l a CH2 1C~ 2n1x where G is a hydrogen or an alkyl group having from 1 to 18 carbon at s in which at least one G must be hydrogen, a is a number of from 0 to 4, . ~
n is 2, 3 or 4 and x is a number of from 1 to 600.
By a further variant, the haloalkylalkoxysilane is a chloro-propyltrimethoxysilane.
- - By a further aspect of this invention, a process is provided for treating a textile material wh;ch comprises: coating a textile materi.al - with a composition containing a silylated polyether of the general formula - ` I
2 ~ CnH2n 3 x R A~
- [CH ( OCnH2n ) x R Ac 1 a ', CH2(0CnH2n)x R Aa _ . . . . . . _._ .
in which at least one R is a radical of the formula . O O
ll ll -OC-Rl-C-O
in which the radical is linked.to the polyether through an ester linkage and the remaining R groups are selected from the group consisting of hydroxyl, hydrocarbonoxy radicals having up to 18-carbon atoms and a radical of the formula O O
., 11 , J
0-C-Rl -C-OH, wherein Rl, when present, is a divalent hydrocarbon radical selected from the group consisting of t-CH2) , wherein y is.a number from 1 to a, -CH=CH~ and a cyclic radical selected from the group consisting of C6H4, C6H8, c6Hlo ana CloH6; A is a silicon-containing radical selected from the formulas -R3-S (OR ) 3-e . . - ~ - 'I ' ' -R3-Sio3 e -- o 2 . , _,,~,,.
in which R is a monovalent hydrocarbon radical having from 1 to 18 carbon a,toms, R is a divalent hydrocarbon Ladical having from 1 to 18 carbon atoms, a is a number of from O to'4, b, c and d are each numbers of from - O to-l-and the sum of b, c, and,d must be at least 1 and when b, c or d are0, then R is selected from the. group consisting of a hydroxyl, a hydrocar--, bonoxy radical,and a radical of the formula O O
. .
-OC-Rl - C-OH, e is a number of from O to 2, n is 2, 3 or 4, and x is a number of at least 1 and up to 600; and thereafter curing-the coated material at a temperature of from 50 to 200C.
By a variant thereof, the silylated polyether is mixed with a diluent prior to coating the textile material~
By a variation thereof, the diluent is a solvent for the sily-lated ~olyether.

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,5 By another variation, the solution contains from 0.2~ to 99 per-cent by weight of silylated polyether based on the weight of silylated polvether and solvent.
By a further variation, the diluent is water.
By other variants9 the textile material is polyester, or a blend of polyester and cotton, or is cellulose.
The silylated polyethers of aspects of this invention may be prepared by reacting an oxyalkylene glycol or copolymers thereof with a dicarboxylic acid or a cyclic anhydride thereof at a temperature of from 80 to 185C., and thereafter reacting the resultant carboxylic acid polymer with a haloalkylalkoxysilane at a temperature of from 50 to 185C.
An acid acceptor, e.g., triethylamine, may be used, if desired.
The oxyalkylene glycols and copolymers thereof which are usedO
to make the compositions of aspects of this invention are well known in 7 a -the art. These glycol pol~mers and copolymers may be illustrated by the following formula:

~-~cn~2n)xG

[I ( n 2n)x ] a CR2~ ( 0CnH2n ) XOG, where G is hydrogen or an alkyl radical having from 1 to 18 carbon atoms, in which at least one G must be hydrogen and a is defined above, n is 2, 3 or 4, x is a number of at least 1 and up to 600, preferably from 10 to 250. Gene-ally, these polymers are made by the homopolymerization or copolymerization of ethylene oxide and propylene oxide using various alcohols as initiators. Examples of alcohols are glycerine, methanol, ethylene glycol, ethanol, t-butanol and the like.
Suitable examples of cyclic anh~drides that may be used to make the compositions of aspects of this invention are succinic anhydride, glutaconic anhydride, maleic anhydride, 1,2-cyclohexanedicarboxylic anhy-dride, l-cyclohexene-1,2-dicarboxylic anhydride, 3-cyclohexene-1,2-dicar-boxylic anhydride, 4-cyclohexene-172-dicarboxylic anhydride, 1,8-naphthalic acid anhydride and phthalic anhydride.
When dicarboxylic acids are used9 it may be advantageous to employ an esterification catalyst, e.g., titanates, alkali metal hydrox-ides, and mineral acids.
Suitable examples of dicarboxylic acids having up to 10 carbon atoms which may be used are oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid.
The haloalkylsilanes which may be used in the preparation of the silylated polyethers of aspects of this invention may be represented by the formula .

I e 2 XR Si (OR ~ 3-e wherein R and R3 and e are the same as above, and X is a halogen, e.g., chlorine, bromine and iodine.
More specifically, suitable examples oE haloalkylsilanes that may be used are chloropropyltrimethoxysilane, chloropropylmethyldimethoxy-silane, chloropropyldimethylethoxysilane, bromobutylethyldimethoxysilane and the like.
In the above reactions, the mole ratio of cyclic anhydride or dicarboxylic acid to hydroxyl groups linked to the polyether may be varied over a wide range. For example, the mole ratio of cyclic anhdride or dicarboxylic acid to hydroxyl groups may range from 0.17:1 to 1.25:1 with the preferred ratio of cyclic anhydride or dicarboxylic acid to hydroxyl groups being from 0.33:1 to 1.1:1, with the proviso that at least one hydroxyl group per molecule is reacted with the cyclic anhydride or dicar-boxylic acid.
In the subsequent silylation of the polyethers, the mole ratio of the carboxylic acid radical formed from the reaction of the cyclic anhydride with the above to the haloalkyl radicals linked to the silane may range from 0.17: to 1.25:1.
Suitable examples of silico~-co~taining radicals represented by A are -C3H6Si(OCH3)3, -C4H8Si(oC2H5)3, C1~3 ~ 3 (CH3~2 3 6 3)2' ~4H8si(0CH3)2~ -C3H6Si OC H
C3H65i 1.5~

-C101~2osi (oC2~f5 ) 2 The unsatisfied valences of the sillcon atoms in the above for-mulas are satisfied by silicon-oxygen-silicon linkages.
Suitable examples of hydrocarbonoxy radicals represented by R
having from 1 to 18 carbon atoms are methoxy7 ethoxy, propoxy, butoxy, octoxy, dodecoxy and octadecoxy radicals. Examples of suitable divalent hydrocarbon radicals represented by Rl which have from 1 to 10 carbon atoms are methylene, ethylene, trimethylene, tetramethylene, pentamethy-lene, hexamethylene, octamethylene and decamethylene radicals. Examples of divalent aryl radicals represented by Rl are phenylene, naphthenylene and cyclohexenylene radicals.
Suitable examples of monovalent hydrocarbon radicals represented by R are alkyl radicals, e.g., methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, dodecyl and octadecyl radicals; aryl radicals, e.g., the phenyl radical; alkaryl radicals, e.g., tolyl, xyxyl and ethylphenyl radicals;
cycloalkyl radicals, e.g., cyclobutyl, cyclohexyl, cyclodecyl radicals;
aralkyl radicals, e.g., benzyl, 2-phenylethyl, 2-phenylpropyl.
Suitable examples of divalent hydrocarbon radicals represented by R are ethylene, trimethylene, tetramethylene, hexamethylene, octa-methylene, dodecamethylene, hexadecamethylene and octadecamethylene radicals.
The silylated polyethers of aspects of this invention can be applied to textile materials in admixture with other substances which have heretofore been used to impart certain properties to textile materials.
Other substances which may be used in combination with the silylated poly-ethers are lubricating agents, agents which impart abrasion resistance to the treated fibers, materials which improve the fragrance of the treated materials, antistatic lubricants, fabric softeners, fire retardants, soil resistant materials and crease-proofing agents. Examples of crease-proofing agents are aminoplast resins, e.g., urea-formaldehyde resins, melamine-formaldehyde resins, and d~methylol dihydroxy ethylene ~rea which may contain magnesium chloride and zinc nitrate as catalysts. Other crease-proofing resins are phenol-formaldehyde and hydroxyethyl methacry-late resins.
The silylated polyethers of aspects of this invention may be applied in concentrated form or as an aqueous solution or as an aqueous dispersion, or dissolved in organic solventfi, e.g., di-n-butylether, aromatic hydrocarbons, and/or chlorinated hydrocarbons.
These silylated polyethers possess a variety of outstanding properties. By way of illustration, they can be prepared so that they are soluble in water. Also, they can be prepared so that they are water in-soluble, but are easily emulsified or dispersed in water without the aid of an emulsifying or dispersing agent.
The amount of silylated polyethers dissolved or dispersed in water may vary over a wide rangeO Generally, the amount of silylated poly-ether present in an aqueous solution or dispersion may range from 0.25 to 99 percent, preferably from 1 to 60 percent and more preferably from 2 to 50 percent by weight based on the weight of the silylated polyether and solvent.
The silylated polyethers of aspects of this invention, and if desired other substances, may be applied to all textile materials, prefer-ably organic textile materials on which organopolysiloxanes have been or could have been applied heretofore. Examples of such textile materials are wool, cotton, rayon, hemp, natural silk, polypropylene, polyethylene, polyester, polyurethane, polyamide, cellulose acetate, polyacrylonitrile fibers, and mixtures of such fibers. The textile materials may consist of staple fibers or monofilaments.
The silylated polyethers of aspects of this invention and other substances, if desired, may be applied to the textile materials by any

6~
means known in the art, e.g., by spraying, immersion7 coating, foaming, calendering or by gliding the fibers across a base which has been saturated with the silylated polyethers of aspects of this invention and other materials, if desired.
Generally, the solids add-on is in the range of from 0.025 to 20 percent and preferably from 0.05 to 10 percent, based on the weight of the original textile material.
After the textile material has been treated, it is dried at an elevated temperature, e.g., from 50 to 200C. for a brief period of time, e.g., from 3 to 15 minutes.
The treated textile material should contain from 0.025 to 10 percent by weight on a dry basis of the cured composition of aspects of this invention.
Textile materials treated with the silylated polyethers of as-pects of this invention possess all of the properties common to prior art textile materials, e.g., soft hand, with the additional property of being hydrophilic and soil resistant.
Specific embodiments of this invention are further illustrated in the following examples in which all parts are by weight unless other-wise specified.
_ample 1 (a) A mixture containing 106.1 parts of succinic anhydride and 2000 parts of oxyethylene-oxypropylene triol copolymer, having a molecular weight of 6360 and a weight ratio of oxyethylene to oxypropylene of 7 to 3 is heated at 175C. for eighteen hours in a reaction vessel. The resul-tant product is a yellow liquid having a viscosity of 4,168 cs. at 25C.
and an acid content of 0.58 milliequiva]ent per gram (theroetical 0.5).
(b) 258.6 parts of the above product are mixed with 29.8 parts of chloropropyltrimethoxysilane, 15.2 parts of triethylamine and 100 parts of toluene and refluxed for nine hours. A white solid by-product is removed by filtration which is identified as triethylamine hydrochloride.
The volatiles are then vacuum stripped off, yielding a brown liquid having a viscosity of 29,347 cs. at 25C. A portion of the resul-tant product is dissolved in water and the water evaporated off in an oven at 172C. A friable-rubber film is formed which shows that a sily-lated product is obtained.
Example 2 (a) A mixture containing 106.1 parts of succinic acid and 2000 parts of oxyethylene-oxypropylene triol copolymer, having a molecular weight of 6360 and a weight ratio of oxyethylene to oxypropylene of 7 to 3, 0.1 part of sulfuric acid and 500 parts of xylene are heated to reflux and the water by-product is collected in a Dean Stark head. The xylene is removed under vacuum (1 torr.) at a temperature up to 150C. The resultant carboxylic acid functional polyether is a yellow liquid having an acid content of 0.59 milliequivalent per gram (theoretical 0.5~.
(b) 258.6 parts of the product prepared in (a) above are mixed with 29.8 parts of chloropropyltrimethoxysilane, 15.2 parts of triethylamine and 100 parts of toluene and refluxed for nine hours. A liquid product containing a white solid precipitate is filtered. The white solid preci-pitate is identified as triethylamine hydrochloride.
The volatiles are then removed under vacuum (1 torr.),yielding a product similar to the silylated polyether formed in Example 1.
Example 3 The procedure of Example 1 is repeated except 155 parts of phthalic anhydride is substituted for the succinic anhydride. A portion of the resu~tant product is dissolved in water and the wa-er evaporated off in an oven at 172C. A friable--rubber film is formed.

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Example 4 The procedure of Example 1 is repeated except that 105 parts of maleic anhydride is substituted for the succinic anhydride. A portion of the resultant product is dissolved in water and the water evaporated off in an oven at 172C~ A friable-rubber film is obtained.
Comparative ~xample Vl 258.6 parts of oxyethylene~oxypropylene triol copolymer, having a molecular weight of 63~0 and a weight ra~io of oxyethylene to oxypropy-lene of 7 to 3 are mixed with 29.~ parts of chloropropyltrimethoxysilane for one hour at room temperature. The resultant mixture is combined with water and then the water is evaporated off in an oven at 172C~ A liquid film is formed which shows the absence of crosslinking.
Example 5 A textile fabric containing a mixture of synthetic polyester - known by the trade mark DACRON and cotton (65/35) is treated with the sily-lated polethers of aspects of this invention by dipping the fabric in aqueous solutions contain'ng 0.7 percent by weight of the various com-positions prepared in the Examples and 1.7 percent by weight of dimethyol dihydroxy ethylene urea in which the percent by weight is based on the total weight of the solution. The fabric is then dried for two minutes at 170C. in a forced air oven. The hydrophilic properties of the fabric are evaluated in accordance with the procedure described in the AATCC
Test Method 39-1977 "Wettability: Evaluation of". Each fabric is then laundered and the properties re-evaluated. Table I shows the results of these tests.
Comparison Example V2 A textile fabric containing a mixture of DACRON-cotton (65/35) is treated with an aqueous solution containing 1.7 percent of dimethyol dihydroxy ethylene urea in accordance with the procedure described in Example 5. The treated fabric has a harsh stiff hand. The results o~ the tests are shown in the Eollowing Table.
Table I
We~ting time, (sec.) Example No. Initial 1 Wash 2 Washes 3 Washes 4 Washes 5 Washes 2 4 7 8 8 1] 12 Compari-son Exam- 10 11 ~ - -ple V2 Fxample 6 - The procedure of Example 5 is repeated except tha~ a DACRON
fabric is treated with aqueous solutions containing 5 percent by weight based on the weight of the aqueous solutions of the compositions described in the Examples~ The dimethyol dihydroxy ethylene urea is omitted from the aqueous solutlons. The following table shows the results of these tests.

Initial Wetting Time Example ~ After 1 Wash None 10 min. 10 min.
l 3 sec. 20 sec.
2 4 sec. 22 sec.
3 S sec. 30 sec.
4 4 sec. - 25 sec.
The above table shows that each of the compositions imparts hydrophilic properties to the treated fabric and after one wash have a soft, silky hand.

Example 7 Fabrics, including cotton, wool, nylon, and rayon are treated with the composition of Example 1 in accordance with the procedure des-cribed in Example 5. The treated fabrics exhibit hydrophilic properties and have a soft, silky hand.

Claims (18)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. Silylated polyethers of the general formula in which at least one R is a radical of the formula in which the radical is linked to the polyether through an ester linkage and the remaining R groups are selected from the group consisting of hydroxyl, hydrocarbonoxy radicals having up to 18 carbon atoms and a radical of the formula wherein R , when present, is a divalent hydrocarbon radical selected from the group consisting of (-CH2)y, wherein y is a number from 1 to 8, -CH=CH- and a cyclic radical selected from the group consisting of C6H4, C6H8, C,H10 and C10H6; A is a silicon-containing radical selected from the formulas in which R2 is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, R3 is a divalent hydrocarbon radical having from 1 to 18 carbon atoms, a is a number of from 0 to 4, b, c and d are each numbers of from 0 to 1 and the sum of b, c and d must be at least 1 and when b, c or d are 0, then R is selected from the group consisting of a hydroxyl, a hydrocar-bonoxy radical and a radical of the formula e is a number of from 0 to 2, n is 2, 3 or 4, and x is a number of at least 1 and up to 600.

2. The silylated polyethers of claim 1, wherein A is a radical of the formula -C3H6Si(OCH3)3.

3. A silylated polyether of the formula in which x is a number of from 1 to 600.

4. A process for preparing silylated polyethers of the general formula in which at least one. R is a radical of the formula in which the radical is linked to the polyether through an ester linkage and the retaining R groups are selected from the group consisting of hydroxyl, hydrocarbonoxy radicals having up to 18 carbon atoms and a radi-cal of the formula wherein R1, when present is a divalent hydrocarbon radical selected from the group consisting of (-CH2)y, wherein y is a number from 1 to 8, -CH=CH- and a cyclic radical selected from the group consisting of C6H4, C6H8, C6H10 and C10H6; A is a silicon-containing radical selected from the formulas in which R is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, R is a divalent hydrocarbon radical having from 1 to 18 carbon atoms, a is a number of from 0 to 4, b, c and d are each a number of from 0 to 1 the the sum of b, c and d must be at least 1 and when b, c or d are 0, then R is selected from the group consisting of a hydroxyl, a hydrocar-bonoxy radical and a radical of the formula e is a number of from 0 to 2, n is 2, 3 or 4, and x is a number of at least 1 and up to 600, which process comprises: reacting an oxyalkylene glycol with a compound selected from the group consisting of a dicarboxylic acid and a cyclic anhydride thereof at a temperature of from 80 to 185°C.;
and thereafter reacting the resultant product with a haloalkylalkoxysilane having from 1 to 3 alkoxy groups linked to the silicon atom at a tempera-ture of from 50 to 185°C.

5. The process of claim 4, wherein the oxyalkylene glycols are represented by the formula where G is a hydrogen or an alkyl group having from 1 to 18 carbon atoms in which at least one G must be hydrogen, a is number of from 0 to 4, n is 2, 3 or 4 and x is a number of from 1 to 600.

6. The process of claim 4, wherein the haloalkylalkoxysilane is a chloropropyltrimethoxysilane.

7. A process for treating a textile material which comprises:
coating a textile material with a composition containing a silylated poly-ether of the general formula in which at least one R is a radical of the formula in which the radical is linked to the polyether through an ester linkage and the remaining R groups are selected from the group consisting of hydroxyl, hydrocarbonoxy radicals having up to 18 carbon atoms and a radical of the formula wherein R , when present is a divalent hydrocarbon radical selected from the group consisting of (-CH2)y, wherein y is a number from 1 to 8, -CH=CH- and a cyclic radical selected from the group consisting of C6H4, C6H8, C6H10 and C10H6; A is a silicon-containing radical selected from the formulas in which R2 is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, R3 is a divalent hydrocarbon radical having from 1 to 18 carbon atoms, a is a number of from 0 to 4, b, c and d are each numbers of from 0 to 1 and the sum of b, c and d must be at least 1 and when b, c or d are 0, then R is selected from the group consisting of a hydroxyl, a hydrocar-bonoxy radical and a radical of the formula e is a number of from 0 to 2, n is 2, 3 or 4, and x is a number of at least 1 and up to 600; and thereafter curing the coated material at a temperature of from 50 to 200°C.

8. The process of claim 7 wherein said silylated polyether is mixed with a diluent prior to coating the textile material.

9. The process of claim 8 wherein said diluent is a solvent for the silylated polyether.

10. The process of claim 9 wherein said solution contains from 0.25 to 99 percent by weight of silylated polyether based on the weight of silylated polyether and solvent.

11. The process of claim 8 wherein said diluent is water.

12. The process of claim 7 wherein said textile material is a polyester.

13. The process of claim 7 wherein said textile material is a blend of polyester and cotton.

14. The process of claim 7 wherein said textile material is cellulose.

15. The coated polyester textile material of claim 12.

16. The coated polyester textile material of claim 12, which contains from 0.025 to 10 percent by weight of the cured composition.

17. The coated polyester/cotton textile material of claim 13.

18. The coated cellulose textile material of claim 14.