GB1598845A - Method of treating synthetic fibres with organosiloxane compositions and the treated fibres obtained therefrom - Google Patents
Method of treating synthetic fibres with organosiloxane compositions and the treated fibres obtained therefrom Download PDFInfo
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- GB1598845A GB1598845A GB2781/78A GB278178A GB1598845A GB 1598845 A GB1598845 A GB 1598845A GB 2781/78 A GB2781/78 A GB 2781/78A GB 278178 A GB278178 A GB 278178A GB 1598845 A GB1598845 A GB 1598845A
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- polydiorganosiloxane
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- siloxane units
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Silicon Polymers (AREA)
Abstract
To the surface of the substrates is applied a polysiloxane which has triorganosiloxane end groups and which on average contains at least two nitrogen-containing siloxane units carrying a radical of the formula -R'(NHCH2CH2)aNHR'' where a is 0 or 1, R' is a bivalent hydrocarbon radical that is alkyl, cycloalkyl, aryl or aralkyl, and R'' is hydrogen or a univalent hydrocarbon radical that is alkyl, cycloalkyl, aryl or aralkyl. The amine functionality of the polydiorganosiloxane expressed as weight percentages of NH or NH2 groups, based on the total weight, must be less than 4 % and the remaining organic radicals of the polydiorganosiloxane must be univalent, optionally fluorinated alkyl or aryl hydrocarbon radicals. The polysiloxane is applied in the form of a liquid and cured by heating, advantageously without a curing agent. It improves the properties of these substrates, in particular the handle, without adversely affecting the flammability characteristics to any significant extent.
Description
(54) A METHOD OF TREATING SYNTHETIC FIBRES WITH
ORGANOSILOXANE COMPOSITIONS AND THE TREATED FIBRES
OBTAINED THEREFROM
(71) We, DOW CORNING CORPORATION of Midland, Michigan, United States of
America, a corporation organized under the laws of the State of Michigan, United States of
America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
This invention relates to a method of treating synthetic fibres with organosiloxane compositions and to the treated fibres obtained therefrom. In one aspect, this invention relates to a method of imparting improved properties such as improved "hand" to textiles consisting of synthetic fibres without diminishing the fire-retardancy rating of the textiles.
Organosilicon compositions are well known in the treatment of textiles to confer desirable properties thereon, such as "hand", antistatic behaviour; oil repellency and improved tear strength. For example, it has long been known to apply a curable organopolysiloxane composition to a fabric or fibre, and subsequently to cure the applied organopolysiloxane by the action of a curing component to produce a fibre or fabric that is surrounded by, i.e. encased in, a sheath of the cured organopolysiloxane composition.
However, a two-component curable composition has certain deficiencies. For example, the curable compositions must often be prepared, shipped and stored in two or more non-curing packages. which are mixed shortly before the intended time of use, in order to avoid premature curing of the composition. This requirement is costly, inconvenient and time-consuming. Further, relatively large amounts of a two-component curable composition must be added to a fabric or fibre in order to provide sufficient integrity for the cured composition to resist mechanical removal, such as by abrasion.
An increasingly important deficiency of two-component curable textile treatments is the tendency of the cured organosiloxane, which is highly cross-linked, to interfere with the flame-retardant properties of the textile. particularly the flame-retardant property due to the melt-drip action of a thermoplastic textile. While certain natural fibres such as wool have some inherent flame-retardancy, many synthetic textiles, for example thermoplastics such as polyethylene terephthalate and nylon, rely on a melting of the ignited textile and a dripping of flaming material to carry away fire and heat from the textile and thus to achieve reduced flammability. We have found that the presence of certain cured organosiloxanes on the surface of such textiles interferes with this melt-drip action and leads to a diminishing of the fire-retardancy rating of the textile.
It is an object of this invention to provide a process for durably treating synthetic fibres to improve the characteristics. such as water repellency, resiliency or "loft", and "hand", of a textile fibre or material consisting of said fibres without diminishing the fire-retardancy rating of the textile fibre or material.
It is a further object of this invention to provide a process for durably treating textiles comprising a synthetic fibre with a polydiorganosiloxane which does not require a curing component to cause crosslinking of the polydiorganosiloxane.
These and other objects are achieved by the process of this invention which comprises applying to a synthetic fibre a polydiorganosiloxane containing siliconbonded, aminocontaining radicals and heating the applied polydiorganosiloxane. The resulting treated fibre has durable affixed to its surface a crosslinked polydiorganosiloxane which is resistant to removal by washing. A fire-retardant fabric consisting of said treated fibres has improved properties such as "hand" without having its fire-retardancy rating diminished when the polydiorganosiloxane is lightly crosslinked. Textiles comprising synthetic fibres and other fibres such as cotton may also be treated by the process of this invention.
The present invention provides a method of treating a nylon or polyester fibre, comprising applying to the surface of said fibre a liquid composition comprising a triorganosiloxane-endblocked polydiorganosiloxane which has an average of at least 100 siloxane units and approximately two nitrogen-containing siloxane units per molecule of polydiorganosiloxane, the silicon atom of said nitrogen-containing siloxane units bearing an aliphatically saturated radical of the formula R'(NHCH2CH2)aNHR" wherein a isO or 1, R' denotes a divalent hydrocarbon radical and R" denotes a hydrogen
radical or a monovalent hydrocarbon radical, any remaining organic radicals in the
polydiorganosiloxane being monovalent radicals, free of aliphatic unsaturation, selected
from hydrocarbon radicals and fluorinated hydrocarbon radicals, and heating the applied triorganosiloxane-endblocked polydiorganosiloxane, thereby providing a treated synthetic fibre having durably affixed to the surface thereof a crosslinked polydiorganosiloxane.
By synthetic fibre is meant a fibre or filament consisting of a nylon or polyester polymer together with any other of the components commonly used in synthetic fibres such as delustrants, fire-control additives and colourants.
By synthetic fibre is further meant a single nylon or polyester fibre or filament, or a plurality of fibres comprising nylon or polyester fibres such as a bundle or tow of fibres of filaments, a yarn, a thread a fibrefill or a fabric such as a woven fabric, an agglomerated random fabric and a knitted fabric.
According to this invention nylon and polyester, e.g. polyethylene terephthalate, are used to prepare oriented and non-oriented fibres used to make filaments threads, yarns, fibrefill and fabrics such as woven fabrics knitted fabrics and random or non-woven fabrics.
The liquid composition that is applied to a surface of a fibre in accordance with this invention comprises a triorganosiloxane-endblocked polydiorganosiloxane. The liquid composition may consist solely of a liquid polydiorganosiloxane. Alternatively, in those cases where the polydiorganosiloxane is not a liquid under ambient conditions, a liquid composition may be prepared by any suitable method. For example, a liquid composition may be prepared by dissolving or dispersing or emulsifying a non-liquid polydiorganosiloxane in a suitable medium such as an organic liquid or water. Of course, it should be understood that a liquid polydiorganosiloxane may also be dissolved dispersed or emulsified instead of, or in addition to, a non-liquid polydiorganosiloxane in such suitable method for preparing a liquid composition.
By ambient conditions are meant the conditions of time. temperature and pressure which are used during the treating of the fibre according to the process of this invention. Thus, it is within the scope of this invention to apply to a fibre a composition which may be a non-liquid at room temperature but which will be a liquid at the higher temperatures that may be used in the method of this invention.
The liquid composition may also contain non-essential components such as pigments, emulsifying agents, fire-retardant additives, plasticizers, anti-static agents and perfumes when desired.
In many instances it is desirable to apply and durably to affix to the surface of a fibre a very small amount, for example less than 1 percent by weight, based on the weight of the fibre, of polydiorganosiloxane. To this end, it is often desirable to prepare a dilute solution of suspension or emulsion of the polydiorganosiloxane and to apply the resulting dilute liquid composition to the fibre.
The viscosity of the liquid composition is not critical. The liquid composition should be sufficiently fluid to permit its use in the method of this invention, i.e. it should be applicable to the desired surface of the fibre under ambient conditions. The volatility of the polydiorganosiloxane should be sufficiently low for at least a portion of it to remain in contact with the surface of the fibre under ambient conditions so that it becomes durably affixed to the surface of the fibre.
The triorganosiloxane-endblocked polydiorganosiloxane is preferably a liquid having a viscosity of less than 100 pascal-seconds (100,000 cp.) at 25"C. Desirable results with respect to the "hand" of a textile comprising the treated fibre are obtained when the viscosity of the polydiorganosiloxane at 250C. has a value of less than 10 pascal-seconds, most preferably from 0.1 to 5 pascal-seconds.
The triorganosiloxane-endblocked polydiorganosiloxane contains terminal triorganosiloxane units of the formula R3SiO1/2 and backbone diorganosiloxane units of the formula R2SiO2i2. Trace amounts of other siloxane units in the polydiorganosiloxane, such as SiO4/2 and RSiO3i2, which are normally present as impurities in commercial polydiorganosiloxanes, are within the scope of this invention. The R radicals of the above siloxane units are bonded to silicon by a silicon-carbon bond and are either nitrogen-containing radicals of the formula -R' (NHCH2CH2)aNHR" or monovalent hydrocarbon radicals or monovalent fluorine-containing hydrocarbon radicals, all of which are free of aliphatic unsaturation.
Suitable nitrogen-containing radicals of the above formula are bonded to silicon by one valence of a divalent R' radical, the other valence of said R' radical being bonded to nitrogen. Divalent hydrocarbon radicals R' may be saturated radicals such as alkylene radicals of the general formula CnH2n - such as -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH(CH3)CH2- and -(CH2)4- and cycloalkylene radicals of the general formula -CnH2n~2-, such as cyclohexylene-1,4; and aromatically unsaturated radicals such as p-phenylene, m-phenylene, -(CH2) C6H4-, -(CH2) C6H4(CH2)n - and ring-alkylated derivatives thereof. In the above formulae n may have a value of from 1 to 18, preferably 3 to 8, all inclusive.Polydiorganosiloxanes wherein the silicon-bonded, nitrogen-containing radicals have a ylene radical such as -CH2CH2CH2- or an alkylated propylene radical such as -CH2CH(CH3)CH2 - as the R' radical are preferred because of ease of synthesis and availability.
Suitable nitrogen-containing radicals of the above formula also bear a nitrogen-bonded monovalent radical R" which may be a hydrogen radical, which is preferred, or a monovalent hydrocarbon radical free of aliphatic unsaturation such as alkyl radicals of the general formula-CmH2m+1 such as methyl, ethyl, propyl, butyl and isobutyl and cycloalkyl radicals of the general formula -CmH2m 1 such as cyclohexyl; and aromatically unsaturated radicals such as phenyl, benzyl and tolyl. In the above formulae m may have a value of from 1 to 18, preferably 1 to 6, all inclusive.
Any R radicals of said siloxane units which are not nitrogen-containing radicals of the above formula are monovalent radicals, free of aliphatic unsaturation, selected from the group consisting of monovalent hydrocarbon radicals, hereinabove delineated as R", and monovalent fluorinated hydrocarbon radicals such as 3,3,3-trifluoropropyl, pentafluorobutyl, pentafluorophenyl and a ,a ,a-trifluorotolyl.
It is to be understood that trace amounts of other monovalent radicals may be present as
R radicals in the polydiorganosiloxane as impurity radicals such as radicals resulting from the particular method of preparation of said polydiorganosiloxanes, hereinafter recited. For example, a convenient method for preparing nitrogen-containing siloxanes is to react a suitable amine with a siloxane or silane which bears a chloropropyl radical. A large percentage of the chloropropyl radicals are thereby converted to amino-containing propyl radicals, any unconverted chloropropyl radicals remaining as said impurity radicals.
In accordance with the above, triorganosiloxane-endblocked polydiorganosiloxanes suitable for use in the process of this invention contain siloxane units bearing nitrogen-containing radicals such as R"NH(CH2CH2NH)aR'SiO"2 and R"NH(CH2CH2NH)a R'SiO2/2 and nitrogen-free siloxane units such as -SiO112 and -SiO212 wherein the undesignated silicon valences are satisfied by nitrogen-free R radicals.
Preferred nitrogen-free R radicals include methyl, phenyl and 3,3,3-trifluoropropyl, and the preferred nitrogen-containing R radical is -CH2CH2CH2NHCH2CH2NH2, thereby giving rise to preferred siloxane units of the formulae (CH3)3SiO, CF3CH2CH2 (CH3)2SiO, CH3(C6H5)2SiO, C6H5(CH3)2SiO, (CH3)2SiO2/2,
CF3CH2CH2(CH3)SiO2/2, CH3(C6H5)SiO2/2, (C6H5)2SiO2/2, Z(CH3)2SiO, Z(C6H5)2SiOij2, Z(C6H5) (CH3)SiO112, Z(CF3CH2CH2) (CH3)SiO112, Z(CF3CH2CH2)SiO2/2, Z(CH3)SiO2t2 and Z(C6H5)SiO, wherein Z denotes the preferred -CH2CH2CH2NHCH2CH2NH2 radical.Polydiorganosiloxanes wherein at least 50 percent of the R radicals are the methyl radical are preferred for modifying a synthetic fibre.
Polydiorganosiloxanes wherein a majority, preferably greater than 90 percent, of the siloxane units are dimethyl siloxane units are preferred for imparting improved "hand" to textiles comprising synthetic fibres treated therewlth.
The trioganosiloxane-endblocked polydiorganosiloxane bears at least two siloxane units which have a -R'(NHCH2CH2)aNHR" radical. Polydiorganosiloxane having greater amounts of the amino-containing siloxane units, such as 3, 4, 5, 10 and more, are also operable in the method of this invention, giving rise to more tightly crosslinked polydiorganosiloxanes durably affixed to the surface of the textile. As noted above, the amino-containing siloxane units of the triorganosiloxane-endblocked polydiorganosiloxane may be terminal triorganosiloxane units or backbone diorganosiloxane units or both terminal and backbone siloxane units.
It is possible to treat a synthetic fibre or a textile consisting of said synthetic fibres according to the method of this invention, without changing the fire-retardancy rating of the fibre or textile. The polydiorganosiloxane contains an average of approximately two amino-containing siloxane units, delineated above, per molecule. The polydiorganosiloxane has more than 100 siloxane units and approximately 2 amino-containing siloxane units per molecule to preserve said fire-retardancy rating.
The flammability of a textile is often determined by the U.S. Department of Commerce
Test No. FF 3-71, "Standard for the Flammability of Children's Sleepware." To pass the DOC FF 3-71 test, a specified textile sample must not burn its entire length of 254 mm. and the length of the char must not exceed 177.8 mm. Furthermore, any material falling from the burning sample must not burn (residual fire) for more than 10 seconds. For the purposes of this invention, the flame-retardancy rating of a textile is determined by the char length and the burning length requirements of DOC FF 3-71 as embodied in DOC FF 5-74, and the residual fire rating of the sample has not been considered.Thus, if none of five samples burns its entire length and the average length of the char of five samples does not exceed 177.8 mm., the sample has a "Pass" fire-retardancy rating. If a textile unmodified by the process of this invention has a Pass rating according to DOC FF 5-74, a textile which is originally identical but has been modified according to the method of this invention may also have a Pass rating according to DOC FF 5-74, depending on whether or not the number of amino-containing siloxane units in each molecule of the polydiorganosiloxane is greater than approximately two.By "identical" textile is meant that the test samples have been taken from the same textile and have been exposed to the same conditions, such as scouring, rinsing, drying, heating and the method of this invention except that the modified textile was in contact with a liquid composition comprising the polydiorganosiloxane polymer during at least a portion of the heating step whereas the unmodified textile was not in said contact during said heating step.
Methods for preparing the triorganosiloxane-endblocked polydiorganosiloxane polymers that are employed according to this invention are well known in the art. Thus, a triorganosiloxane-endblocked polydiorganosiloxane bearing a limited number of suitably reactive groups such as iiSiH or iiSiCH2CH2CH2Cl may be reacted with CH2=C(CH3)CH2NH2CH2NH2 or H2NCH2CH2NH2, respectively, to provide an analogous polydiorganosiloxane wherein the reactive groups have been converted to -CHCH(CH)CH2NHCH2CH,NH2 groups and CH2CH2CH2NHCH2CH2NH2 groups, respectively. Small amounts of unreacted =SiH or =SiCH?CH7CH,CI groups may remain as impurity groups, as hereinbefore discussed.Alternatively, a suitable triorganosiloxane endblocked polydiorganosiloxane may be prepared from amino-containing silanes or siloxanes using well-known methods or hydrolysis and equilibration. For example, Pike et al. U.S. Patent No. 3,033,815, Speier U.S. Patent No. 3,146,250 and Brown U.S. Patent
No. 3,355,424 contain teachings which may be adapted to prepare polydiorganosiloxanes which are suitable for use in the method of this invention.
In general, it is preferred to prepare suitable polydiorganosiloxanes by equilibration of the hydrolysate of a silane such as R"NH(CH2CH2NH)aR'Sj(R")Y2 with a cyclic siloxane of the formula (R,SiO), and a source of endblocking units such as R3SiY wherein Y is a hydrolysable group or atom, x has a value of three or more and R and R' are as hereinbefore defined.
A highly preferred trioganosiloxane-endblocked polydiorganosiloxane for the method of this invention may be prepared by hydrolysing H2NCH2CH2NHCH2CH2CH2Si(CH3) (OCH3)2 in excess water and equilibrating the resulting hydrolysate with dimethylcyclopolysiloxane and decamethyltetrasiloxane, using a base catalyst such as KOH, to provide a polydiorganosiloxane having about 100 siloxane units, 2 of which bear aminoethylaminopropyl radicals.
A highly preferred liquid composition for the method of this invention may be prepared by preparing a dilute aqueous emulsion of the above highly preferred polydiorganosilox- ane, using a suitable emulsifying agent such as a non-ionic emulsifying agent.
In the process of this invention, the liquid composition may be applied to a surface of the fibre in any suitable manner such as by brushing, rinsing, padding, dipping, spraying, dusting. thermal transfer processes or fluid-bed methods. The liquid composition may be applied to the entire surface of the fibre or to any portion of the surface as desired.
The applied liquid composition may be crosslinked by heating to a temperature of from above room temperature to less than the melting or decomposing temperature of the synthetic fibre. Any heating may be done at any convenient time providing the fibre is in contact with at least the polydiorganosiloxane for an effective length of time. An effective length of time means a span of time at the particular heating temperature that is sufficient to allow the polydiorganosiloxane to be crosslinked and durably affixed to the surface of the fibre. Thus, the liquid composition must be exposed to said temperature during or after the applying of the liquid composition to the surface of the fibre.
Heating the composition may be done by any suitable method or combination of methods such as with infrared radiation; a suitable hot fluid such as hot air or steam; electrical heating elements and microwave heating. Alternatively, the liquid may be applied to a hot fibre. The fibre or polydiorganosiloxane should not be heated to such a high temperature as to melt the fibre or adversely to affect, e.g. by decomposition, the fibre and/or the polydiorganosiloxane.
We have found that the preferred polydiorganosiloxanes described above will crosslink on the surface of synthetic fibres at temperatures as low as 50"C. For example, the method of this invention is useful as a fabric-softening method in a clothes washing procedure at from 50"C to 70"C. such as in the rinse and dry cycle of an automatic washer.
An article whose fibres may be modified by the process of this invention may consist solely of the synthetic fibres or said article may comprise other components which are not synthetic fibres. For example, it is within the scope of this invention to treat the surface of a textile which comprises components such as wool or cotton components. The surface of these other components may or may not be concurrently modified during the process of this invention.
After the fibre has been treated, i.e. having the liquid composition applied and having been heated to a suitable temperature as described above, the poly-diorganosiloxane is crosslinked and is durably affixed to the surface of the fibre.
By "durably affixed" is meant that the crosslinked polydiorganosiloxane cannot be washed from the surface of the fibre to a non-detectable level by 10 machine washings according to the AATCC 124-1973 test method.
By crosslinked polydiorganosiloxane is meant that the durably affixed polymer cannot be dissolved in toluene using one or more of the following methods: Thus, the polydiorganosiloxane is crosslinked: (i) if it cannot be dissolved from the surface of the fibre at a temperature below the melting temperature of the fibre; or (ii) if, when the fibre is dissolved, leaving a polydiorganosiloxane polymer, said polymer is insoluble in toluene, or (iii) if the combination of the fibre and the durably affixed polydiorganosiloxane cannot be dissolved in toluene, or (iv) if, when the fibre is melted, leaving a polydiorganosiloxane polymer, said polymer is insoluble in toluene. Solvents for synthetic fibres and polydiorganosiloxane polymers are well known to those skilled in the synthetic polymer art.
It should be understood that the method of this invention may be used to modify an end-product comprising a synthetic fibre or said fibre may be so modified and subsequently fabricated to an end-product. For example, it is within the scope of this method to modify a synthetic fibre or filament at any suitable point in its manufacturing process or thereafter, and subsequently to fabricate an article such as a yarn or a fabric from said modified fibre or filament. Alternatively. a fabric may be fashioned comprising a synthetic fibre or filament and, subsequently, at least the synthetic fibre portion of said fabric may be modified by said process.
The process of this invention is further illustrated by the following examples which teach the best mode for carrying out the invention; however, said examples should not be regarded as limiting the invention which is defined by the appended claims. All parts are parts by weight.
Example 1
A siloxane having the formula Me3SiO(Me2SiO)g,- (MeZSiO)2SiMe3, wherein Me denotes CH3 and Z denotes -CH2CH2CH2NHCH2CH2NH2 was emulsified using a blend of 66.9 parts water, 1.8 parts of Tergitol (trade mark) TMN-6 non-ionic surfactant and 1.3 parts Igepal (trade mark) CA-897 of non-ionic surfactant for every 30 parts of the siloxane.
The siloxane was mixed with the blend using mechanical mixing and the mixture was homogenized twice at 6000 psi. The resulting 30 weight percent siloxane emulsion was diluted with water as needed for the following examples. Weighed samples of prewashed and dried polyethylene terephthalate (PET) and nylon-knit fabrics were padded using the above emulsions of varying concentration. The padded samples were heated at 204"C. for 90 seconds. washed for 15 minutes at 77"C. with a 0.1 percent Triton (trade mark) X-100 solution. rinsed, air dried and reweighed to determine the percentage of siloxane add-on.
Table I below summarizes these data. All treated samples exhibited good "hand" and
AATCC spray ratings of 70 to 80.
Example 2
Nylon and PET samples of Example 1 having 4.5 weight percent add-on were tested for flame retardancy according to DOC FF 5-74. Although the melt-drip behaviour of these samples was reduced, as compared with the untreated fabrics, the samples were self-extinguishing by a combination of melt-drip behaviour and charring, thereby retaining a PASS fire-retardancy rating. The treated samples were extracted with an equal volume mixture of phenol and o-dichlorobenzene which dissolved the fibres and left a crosslinked, insoluble polydiorganosiloxane residue which could not be melted at temperatures as high as 3500C.
Example 3
Nylon 6 knitted and PET woven fabrics were washed in an automatic clothes washer wherein from 10 to 50 grams of the 30 percent siloxane emulsion of Example 1 were automatically added to the washer during the rinse cycle. The washed and treated samples have improved "hand" and were self-extinguishing in the DOC FF 5-74 flammability test.
Example 4
Several samples of a blue print, fire-retarded PET woven fabric treated as in Example 1 and having approximately 2.8 weight percent add-on were subjected to 10 machine washings according to the AATCC 124-1973 test method. Although the samples lost approximately 34 percent of the siloxane add-on, they experienced no loss of "hand", water repellency or self-extinguishing characteristics. Additional samples of the treated PET fabric were rinsed 10 times with perchloroethylene to determine dry cleaning durability.
The rinsed samples lost approximately 80 percent of the siloxane add-on and consequently lost "hand" and water repellency.
Example 5
PET fiberfill was treated as in Example 1 with siloxane bath concentrations of 0.5 and 2.0 percent siloxane producing add-on of less than 0.1 and 4.5 weight percent, respectively. The sample of fiberfill having less than 0.1 weight percent add-on possessed better "hand" than
Dacron (trade mark) II fiberfill. Flammability of the untreated fiberfill, the two treated fiberfill samples and Dacron (trade mark) II fiberfill was evaluated in two ways. In the Pan
Burn test, 0.3 g of a sample was placed in a 5.6 cm. diameter x 2.0 cm. deep aluminium cup and the sample was ignited with a 1" lazy yellow Bunsen flame for 3 seconds. The burn time of the sample after the burner was removed was noted. In the Vertical Burn test, 0.3 g. of a sample was fashioned into a 1" x 5" wad and suspended over an aluminium cup to collect burning fragments, and the sample was ignited at the bottom end with a 1" lazy, yellow
Bunsen flame for 3 seconds. The burn time for the sample and the fragments after the burner had been removed were noted. Table II below summarizes these data which show that fiberfill which has been treated by the method of this invention have flammability characteristics which are little different from the flammability of untreated fiberfill.
TABLE I
Bath Concentration Add-On (W% of Fabric)
(W% Siloxane) Nylon 6 PET
0.5 3.5 1
2.5 4.5 2.5
5 6.5 4.5
10.5 13 7 TABLE II
Burn time (seconds)
Sample Pan Burn Vertical Burn Fragment Burn
Untreated Fiberfill 15 3 7
Dacron II Fiberfill 26 11 26
Fiberfill ( < 0.1 weight percent Add-on) 3 7 7
Fiberfill (4.5 weight percent Add-on) 8.5 8 8
Claims (10)
1. A method of treating a nylon or polyester fibre, comprising applying to the surface of said fibre a liquid composition comprising a triorganosiloxane-endblocked polydiorganosiloxane which has an average of at least 100 siloxane units and approximately two nitrogen-containing siloxane units per molecule of polydiorganosiloxane, the silicon atom of said nitrogen-containing siloxane units bearing an aliphatically saturated radical of the formula
(I) -R' (NHCH,CH2)aNHR" wherein a is 0 or 1, R' denotes a divaient hydrocarbon radical and R" denotes a hydrogen
radical or a monovalent hydrocarbon radical, any remaining organic radicals in the
polydiorganosiloxane being monovalent radicals, free of aliphatic unsaturation, selected
from hydrocarbon radicals and fluorinated hydrocarbon radicals, and heating the applied triorganosiloxane-endblocked polydiorganosiloxane. thereby providing a treated synthetic fibre having durably affixed to the surface thereof a crosslinked polydiorganosiloxane.
2. A method according to claim 1, wherein the polydiorganosiloxane is heated to a temperature of from 50"C to 250"C. after it has been applied to the fibre.
3. A method according to claim 1 or 2, in which less than 1% of the polydiorganosiloxane, based on the weight of the fibre, is applied and durably affixed to the surface of the fibre.
4. A method according to any of claims 1 to 3, in which the viscosity of the polydiorganosiloxane at 25"C. has a value of less than 10 pascal-seconds.
5. A method as claimed in any of claims 1 to 4, in which the divalent hydrocarbon radicals R' are alkylene radicals of the general formula: CnH2n- ; cycloalkylene radicals of the general formula: CnH2n2 ; or aromatic rings, including alkyl substituted derivatives thereof, n having a value of from 1 to 18.
6. A method according to claim 5, in which n has a value of from 3 to 8.
7. A method as claimed in claim 6. in which the silicon-bonded nitrogen-containing radicals have a propylene or an alkylated propylene radical as the R' radical.
8. A method as claimed in any of claims 1 to 7 in which radical R" is an aromatic ring.
9. A method according to claim 1, substantially as herein described with reference to any of the specific examples.
10. Synthetic fibres treated by a method according to any of claims 1 to 9.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76467477A | 1977-02-02 | 1977-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1598845A true GB1598845A (en) | 1981-09-23 |
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ID=25071421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2781/78A Expired GB1598845A (en) | 1977-02-02 | 1978-01-24 | Method of treating synthetic fibres with organosiloxane compositions and the treated fibres obtained therefrom |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5398499A (en) |
| CA (1) | CA1118163A (en) |
| CH (1) | CH637800GA3 (en) |
| DE (1) | DE2754704B2 (en) |
| FR (1) | FR2379643A1 (en) |
| GB (1) | GB1598845A (en) |
| IT (1) | IT1087966B (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4459382A (en) * | 1981-08-06 | 1984-07-10 | Toray Silicone Company, Ltd. | Fiber-treating compositions comprising epoxyfunctional silicones and aminofunctional silicone copolymers or carboxyfunctional silicone copolymers |
| US4541936A (en) * | 1983-09-16 | 1985-09-17 | Toray Silicone Company, Ltd. | Method and siloxane composition for treating fibers |
| EP0575972A2 (en) * | 1992-06-25 | 1993-12-29 | Dow Corning Toray Silicone Company, Limited | Amino-containing organopolysiloxane and method for its preparation |
| USRE34584E (en) | 1984-11-09 | 1994-04-12 | The Procter & Gamble Company | Shampoo compositions |
| US5334653A (en) * | 1991-08-30 | 1994-08-02 | Dow Corning Toray Silicone Co., Ltd. | Polyester fiber coating compositions |
| US6001422A (en) * | 1997-04-11 | 1999-12-14 | Shin-Etsu Chemical Co., Ltd. | Method for finishing treatment of a fabric material |
| EP1081283A1 (en) * | 1999-08-31 | 2001-03-07 | Dow Corning Toray Silicone Co., Ltd. | Sizing agent composition for printing paper |
| US8211542B2 (en) | 2004-09-07 | 2012-07-03 | Kaneka Corporation | Artificial hair made of flame-retardant polyester |
| US10040891B2 (en) | 2014-04-10 | 2018-08-07 | Shin-Etsu Chemical Co., Ltd. | Silicone composition, silicone emulsion composition, and fiber treatment agent |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6094680A (en) * | 1983-10-28 | 1985-05-27 | 東レ・ダウコーニング・シリコーン株式会社 | Fiber treating agent |
| GB8401875D0 (en) * | 1984-01-25 | 1984-02-29 | Procter & Gamble | Liquid detergent compositions |
| JPS6461576A (en) * | 1987-08-27 | 1989-03-08 | Lion Corp | Gloss preventing composition |
| JP2649061B2 (en) * | 1988-05-26 | 1997-09-03 | 東レ・ダウコーニング・シリコーン株式会社 | Fiber treatment agent |
| JPH0825255B2 (en) * | 1991-08-09 | 1996-03-13 | 信越化学工業株式会社 | Water repellent paperboard |
| CN1063461C (en) * | 1995-06-22 | 2001-03-21 | 财团法人工业技术研究院 | Amido siloxanes polymer comb-like block-state alternant molecular structure and its prepn. |
| JP4036354B2 (en) * | 1998-10-12 | 2008-01-23 | 信越化学工業株式会社 | Waterproofing agent composition mainly composed of organopolysiloxane |
| TW538096B (en) | 1999-06-25 | 2003-06-21 | Shinetsu Chemical Co | Nitrogen atom-containing polysiloxanes, their preparation, and fiber and fabric finishing agent compositions |
| WO2001025382A1 (en) * | 1999-10-05 | 2001-04-12 | Ciba Speciality Chemicals Holding Inc. | Fabric softener compositions |
| JP6394493B2 (en) | 2015-05-18 | 2018-09-26 | 信越化学工業株式会社 | Block polyisocyanate-containing curable silicone composition and fiber treatment agent using the same |
| PL3594301T3 (en) | 2017-03-07 | 2022-06-27 | Kao Corporation | Film comprising hydrophobized cellulose fibers and oil |
| JP6921597B2 (en) * | 2017-04-13 | 2021-08-18 | 花王株式会社 | Gel membrane |
| JP7003707B2 (en) | 2018-02-07 | 2022-01-21 | 信越化学工業株式会社 | Fiber treatment agent and its manufacturing method |
| WO2020235522A1 (en) | 2019-05-22 | 2020-11-26 | 信越化学工業株式会社 | Aminoalkyl group-containing organopolysiloxane and fiber treatment agent |
| EP4008750A4 (en) | 2019-08-02 | 2023-08-09 | Kao Corporation | Emulsification composition containing hydrophobic-modified cellulose fibers |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL131978C (en) * | 1966-05-11 | |||
| US3766115A (en) * | 1971-05-21 | 1973-10-16 | Du Pont | Finish composition for application to a continuous filament polypropylene sheet |
| US3890269A (en) * | 1972-08-11 | 1975-06-17 | Stauffer Chemical Co | Process for preparing aminofunctional polysiloxane polymers |
| JPS5319718B2 (en) * | 1972-11-14 | 1978-06-22 | ||
| GB1485769A (en) * | 1973-12-18 | 1977-09-14 | Dow Corning Ltd | Process for treating fibres |
| JPS5830415B2 (en) * | 1975-03-07 | 1983-06-29 | 東レ株式会社 | Method for producing acrylic fiber with substantially modified texture |
-
1977
- 1977-09-16 CA CA000286932A patent/CA1118163A/en not_active Expired
- 1977-10-17 IT IT28671/77A patent/IT1087966B/en active
- 1977-11-18 JP JP13802777A patent/JPS5398499A/en active Granted
- 1977-12-08 DE DE2754704A patent/DE2754704B2/en not_active Ceased
-
1978
- 1978-01-24 GB GB2781/78A patent/GB1598845A/en not_active Expired
- 1978-02-01 CH CH111778A patent/CH637800GA3/en unknown
- 1978-02-01 FR FR7802753A patent/FR2379643A1/en active Granted
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4459382A (en) * | 1981-08-06 | 1984-07-10 | Toray Silicone Company, Ltd. | Fiber-treating compositions comprising epoxyfunctional silicones and aminofunctional silicone copolymers or carboxyfunctional silicone copolymers |
| US4541936A (en) * | 1983-09-16 | 1985-09-17 | Toray Silicone Company, Ltd. | Method and siloxane composition for treating fibers |
| USRE34584E (en) | 1984-11-09 | 1994-04-12 | The Procter & Gamble Company | Shampoo compositions |
| US5334653A (en) * | 1991-08-30 | 1994-08-02 | Dow Corning Toray Silicone Co., Ltd. | Polyester fiber coating compositions |
| EP0575972A2 (en) * | 1992-06-25 | 1993-12-29 | Dow Corning Toray Silicone Company, Limited | Amino-containing organopolysiloxane and method for its preparation |
| EP0575972A3 (en) * | 1992-06-25 | 1994-10-19 | Dow Corning Toray Silicone | Amino-containing organopolysiloxane and method for its preparation. |
| US6001422A (en) * | 1997-04-11 | 1999-12-14 | Shin-Etsu Chemical Co., Ltd. | Method for finishing treatment of a fabric material |
| EP1081283A1 (en) * | 1999-08-31 | 2001-03-07 | Dow Corning Toray Silicone Co., Ltd. | Sizing agent composition for printing paper |
| US8211542B2 (en) | 2004-09-07 | 2012-07-03 | Kaneka Corporation | Artificial hair made of flame-retardant polyester |
| US8545981B2 (en) | 2004-09-07 | 2013-10-01 | Kaneka Corporation | Artificial hair made of flame-retardant polyester |
| US10040891B2 (en) | 2014-04-10 | 2018-08-07 | Shin-Etsu Chemical Co., Ltd. | Silicone composition, silicone emulsion composition, and fiber treatment agent |
Also Published As
| Publication number | Publication date |
|---|---|
| CH637800GA3 (en) | 1983-08-31 |
| FR2379643A1 (en) | 1978-09-01 |
| FR2379643B1 (en) | 1980-04-25 |
| DE2754704B2 (en) | 1981-07-30 |
| JPS5398499A (en) | 1978-08-28 |
| CA1118163A (en) | 1982-02-16 |
| IT1087966B (en) | 1985-06-04 |
| JPS5743673B2 (en) | 1982-09-16 |
| DE2754704A1 (en) | 1978-08-03 |
| CH637800B (en) |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |