CA1041707A - Process for treating fibres - Google Patents
Process for treating fibresInfo
- Publication number
- CA1041707A CA1041707A CA216,120A CA216120A CA1041707A CA 1041707 A CA1041707 A CA 1041707A CA 216120 A CA216120 A CA 216120A CA 1041707 A CA1041707 A CA 1041707A
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Classifications
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
- Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics
Abstract
ABSTRACT OF THE DISCLOSURE
Method for imparting reslience and crease resistance to synthetic fibres, particularly knitted fabrics, by applying to the fibres a composition obtained by mixing a hydroxylated polydiorganosiloxane, an organosilane having amino and alkoxy or alkoxyalkoxy groups in the molecule and an organosilane having alkoxy or alkoxyalkoxy groups and hydrogen atoms, monovalent hydrocarbon or halogenated hydrocarbon groups in the molecule. Partial hydrolysates of the silanes may optionally be used. The applied composition is then cured at normal or elevated temperatures. The compositions preferably also contain a siloxane condensation catalyst and may further contain a hydroxylated organic compound.
Method for imparting reslience and crease resistance to synthetic fibres, particularly knitted fabrics, by applying to the fibres a composition obtained by mixing a hydroxylated polydiorganosiloxane, an organosilane having amino and alkoxy or alkoxyalkoxy groups in the molecule and an organosilane having alkoxy or alkoxyalkoxy groups and hydrogen atoms, monovalent hydrocarbon or halogenated hydrocarbon groups in the molecule. Partial hydrolysates of the silanes may optionally be used. The applied composition is then cured at normal or elevated temperatures. The compositions preferably also contain a siloxane condensation catalyst and may further contain a hydroxylated organic compound.
Description
4~q~J7 This invention relates to a proces~ ~or the treatment o~ textile ~ibre~.
It is known to treat textile fibre~ 9 particularly cotton and synthetics, with organopolysiloxanes and compositions containing organopolysiloxanes to impart thereto properties such as water repellency and lubricity.
Whil~t the achievement of such properties i3 now co~mercially well established there has been a continuing e~fort ~oward~
~; endowing synthetic fibres with other de~irable properties.
1~ For example, there has existed a de~ire to improve the resilience of synthetic ~ibres; this property being related to the ability of the ~ibres to return to their original appearance or dimensions a~ter crushin~ or stretching. Any improve~ent in resiliency is therefore to be de~ired as it increase~ the resistance o~ ~ynthetic ~abrics to wrinkling and also imparts springiness and bounce. Although known organopolysiloxane textile trea~tments ha~e resulted in an improvement in the resilience of synthe~ic ~abrics such improvement has generally been of a low order. In addition the e~ect has not been durable to laundering or dry cleaning.
We have now ~ound ~hat a si~nificant improvement in the resiliency of synthetic ~ibres can be obtained ~y ~reatment o~ the fibres, either ~ se or as blend~ with cellulosic fibresg with a certain type o~ organopolyæiloxane ', compo~ition. We have al~o ~ound that the improvement in resiliency obtained is retaine~ to a substantial extent even a~ter the treated ~ibres have been subjected to laundering or dry cleaning.
Accordin~ly this invention provides a process ~or the treatment of synthe~ic ~ibre~ which comprises applying : ::
' ' '''~' ' .
It is known to treat textile fibre~ 9 particularly cotton and synthetics, with organopolysiloxanes and compositions containing organopolysiloxanes to impart thereto properties such as water repellency and lubricity.
Whil~t the achievement of such properties i3 now co~mercially well established there has been a continuing e~fort ~oward~
~; endowing synthetic fibres with other de~irable properties.
1~ For example, there has existed a de~ire to improve the resilience of synthetic ~ibres; this property being related to the ability of the ~ibres to return to their original appearance or dimensions a~ter crushin~ or stretching. Any improve~ent in resiliency is therefore to be de~ired as it increase~ the resistance o~ ~ynthetic ~abrics to wrinkling and also imparts springiness and bounce. Although known organopolysiloxane textile trea~tments ha~e resulted in an improvement in the resilience of synthe~ic ~abrics such improvement has generally been of a low order. In addition the e~ect has not been durable to laundering or dry cleaning.
We have now ~ound ~hat a si~nificant improvement in the resiliency of synthetic ~ibres can be obtained ~y ~reatment o~ the fibres, either ~ se or as blend~ with cellulosic fibresg with a certain type o~ organopolyæiloxane ', compo~ition. We have al~o ~ound that the improvement in resiliency obtained is retaine~ to a substantial extent even a~ter the treated ~ibres have been subjected to laundering or dry cleaning.
Accordin~ly this invention provides a process ~or the treatment of synthe~ic ~ibre~ which comprises applying : ::
' ' '''~' ' .
2 - ~
.,, : ' ' ~4D417~7 thereto from 0.1 to 40~ based on the weight of the fibres of a composition comprising the product obtained by mixing (A) 100 parts by weight of a polydiorganosiloxane having terminal silicon-bonded hydroxyl radicals and a molecular weight of at least 750, at least 50 per cent of the organie substituents in the polydiorganosiloxane being methyl radicals, any other organic substituents present being monovalent hydrocarbon radicals having from 2 to 30 carbon atoms, (B) 0.5 to 25 parts by weight of an organosilicon compound selected from the group consisting of organosilanes having the general formula RSiR'aX3 a wherein R represents a monovalent radical composed of carhon, hydrogen, nitrogen and, optionally, oxygen which radical contains at least two amine groups and is attached to silicon through a silicon to carbon linkage, R' represents an alkyl ;
radical or an aryl radical, each X represents an alkoxy or alkoxyalkoxy radical having from 1 to 14 inclusive carbon atoms, and a is 0 or l, and partial hydrolysates of said organosilanes and (C) 1.0 to 25 parts by weight o~ an organo- `~
silicon compound selected from the group consisting of silanes having the general formula R"bSiZ4 b~ wherein R" is a hydrogen atom, a monovalent hydrocarbon radical or monovalent halogenated hydrocarbon radical, Z is an alkoxy or alkoxyalkoxy radical having from l to 4 inclusive carbon atoms and _ is 0 or 1 and partial hydrolysates of said silanes, and thereafter curing the applied composition.
The polydiorganosiloxanes (A) are linear or -substantially linear siloxane polymers having terminal silicon-bonded hydroxyl radicals. Such polydiorganosiloxanes have -about two, that is from about i.9 to 2, organic radicals per silicon atom and methods for their preparation are well known in the art. The polydiorganosiloxanes should have an average molecular weight of at least 750, preferably from 20,000 to 90, 000 . ~ . .
, o`:~
At least 50 per cent o~ the silicon-bonded organic substituents in the polydiorgano~iloxane are methyl, any `` other substituents being monovalent hydrocarbon radicals having from 2 to 30 carbon atomsg :~or exampleg alkyl and cycloalkyl radicals~ e.g. ethylg propyl9 butyl~ n-octyl3 tetradecyl 3 octadecyl and cyclohexylg alkenyl radicals e.~.
vinyl and allyl and aryl a aralkyl and alkaryl radicals e.g.
phenyl, tolyl and benzyl. A small proportion of hydroxyl radicals may be attached to non-terminal silicon atoms in the polydiorganosiloxane. Howeverg such non-terminal hydroxyl radicals should preferably not exceed about 5~ of - the total substituents in the polydiorganosiloxane. The pre~erred polydiorganosiloxanes are the polydimethylsiloxanes i.e. those represented by the ~ormula ;: _ ~ l .~ 15 I H3 n~_ -SiO- rH
^; . 3 x ; . .
~- in which x is an integer, preferab~y having a value such that the polydiorganosiloxane has a YiScosity of ~rom 100 ~o 20 509000 cS at 25C.
Component (B) o~ the compositions employed in the process o~ ~his invention is an organosilane o~ the general formula RSiR'aX3_a wherein R, R'g X and a are as defined ~ ...................................................................... . . .
- hereinabove~ and/or it may be a partial hydrolysate o~ said organosilane. Such organosilanes are known substances and ~hey may be prepared as describedg ~or example) in U.K. ;
Patents Nos. 858g445 and 1,017,257. In the general formula of the organo~ilanes the radical R is composed of carbon hydrogeng nitrogen andg optionallyg oxygen and contains at .
:
.:
_ 4 _ , 7~
least two amine (which term includes imine) groups. It is attached to silicon through a silicon to carbon linkage, there being preferably a bridge of at least 3 carbon atoms ; separating the silicon atom and the nearest nitrogen atom or atoms. Preferably also, R contains less than about 21 .~ carbon atoms and any oxygen is present in carbonyl and/or ether groups. Examples of the operative R substituents are -(CH2)3MHCH2CH2NH2~ - (CH2)4NHCH2 2 3 -CH .cH.cH3cH2NHcH2cH2NH2r ~ (CH2)3NHCH2 2 2 2 2 r_~ -(CH2)3NHCH2CH2CH(CH2)3NH2 and (CH2)3NH(CH2)2N~CH2CH2COOCH3.
- Each of the X substituents may be an alkoxy or alkoxyalkoxy ' radical having from 1 to 14 carbon atoms, preferably from 1 to 4 carbon atoms. Examples of X radicals are methoxy, iso-propoxy, hexoxy, decyloxy and methoxyethoxy. When present R' may be any alkyl or aryl radical, preferably having less than 19 carbon atoms, e.g. methyl, ethyl, propyl, octyl or phenyl. Preferred as component (B) are the organosilanes wherein R represents the -(CH2)3NHCH2CH2NH2 or the -CH2CHCH3CH2NHCH2CH2NH2 radicals, each X represents an alkoxy radical having from 1 to 4 inclusive carbon atoms and R', when present, represents the methyl radical.
As component (C) there are employed silanes of the general formula R"bSiZ4 b wherein R", Z and _ are as defined hereinabove, or partial hydrolysates of said silanes. In the general formula of the silanes (C) R" may be a!~hydrogen atom or a monovalent hydrocarbon radical or halogenated hydrocarbon radical, for example alkyl, e.g. methyl, ethyl, propyl, butyl, hexyl, decyl, octadecyl, alkenyl e.g. vinyl or allyl, aryl, aralkyl or alkaryl e.g. phenyl, tolyl or , -1091~07 benzyl, halogenoalkyl, e.g. chloromethyl, bromoethyl or
.,, : ' ' ~4D417~7 thereto from 0.1 to 40~ based on the weight of the fibres of a composition comprising the product obtained by mixing (A) 100 parts by weight of a polydiorganosiloxane having terminal silicon-bonded hydroxyl radicals and a molecular weight of at least 750, at least 50 per cent of the organie substituents in the polydiorganosiloxane being methyl radicals, any other organic substituents present being monovalent hydrocarbon radicals having from 2 to 30 carbon atoms, (B) 0.5 to 25 parts by weight of an organosilicon compound selected from the group consisting of organosilanes having the general formula RSiR'aX3 a wherein R represents a monovalent radical composed of carhon, hydrogen, nitrogen and, optionally, oxygen which radical contains at least two amine groups and is attached to silicon through a silicon to carbon linkage, R' represents an alkyl ;
radical or an aryl radical, each X represents an alkoxy or alkoxyalkoxy radical having from 1 to 14 inclusive carbon atoms, and a is 0 or l, and partial hydrolysates of said organosilanes and (C) 1.0 to 25 parts by weight o~ an organo- `~
silicon compound selected from the group consisting of silanes having the general formula R"bSiZ4 b~ wherein R" is a hydrogen atom, a monovalent hydrocarbon radical or monovalent halogenated hydrocarbon radical, Z is an alkoxy or alkoxyalkoxy radical having from l to 4 inclusive carbon atoms and _ is 0 or 1 and partial hydrolysates of said silanes, and thereafter curing the applied composition.
The polydiorganosiloxanes (A) are linear or -substantially linear siloxane polymers having terminal silicon-bonded hydroxyl radicals. Such polydiorganosiloxanes have -about two, that is from about i.9 to 2, organic radicals per silicon atom and methods for their preparation are well known in the art. The polydiorganosiloxanes should have an average molecular weight of at least 750, preferably from 20,000 to 90, 000 . ~ . .
, o`:~
At least 50 per cent o~ the silicon-bonded organic substituents in the polydiorgano~iloxane are methyl, any `` other substituents being monovalent hydrocarbon radicals having from 2 to 30 carbon atomsg :~or exampleg alkyl and cycloalkyl radicals~ e.g. ethylg propyl9 butyl~ n-octyl3 tetradecyl 3 octadecyl and cyclohexylg alkenyl radicals e.~.
vinyl and allyl and aryl a aralkyl and alkaryl radicals e.g.
phenyl, tolyl and benzyl. A small proportion of hydroxyl radicals may be attached to non-terminal silicon atoms in the polydiorganosiloxane. Howeverg such non-terminal hydroxyl radicals should preferably not exceed about 5~ of - the total substituents in the polydiorganosiloxane. The pre~erred polydiorganosiloxanes are the polydimethylsiloxanes i.e. those represented by the ~ormula ;: _ ~ l .~ 15 I H3 n~_ -SiO- rH
^; . 3 x ; . .
~- in which x is an integer, preferab~y having a value such that the polydiorganosiloxane has a YiScosity of ~rom 100 ~o 20 509000 cS at 25C.
Component (B) o~ the compositions employed in the process o~ ~his invention is an organosilane o~ the general formula RSiR'aX3_a wherein R, R'g X and a are as defined ~ ...................................................................... . . .
- hereinabove~ and/or it may be a partial hydrolysate o~ said organosilane. Such organosilanes are known substances and ~hey may be prepared as describedg ~or example) in U.K. ;
Patents Nos. 858g445 and 1,017,257. In the general formula of the organo~ilanes the radical R is composed of carbon hydrogeng nitrogen andg optionallyg oxygen and contains at .
:
.:
_ 4 _ , 7~
least two amine (which term includes imine) groups. It is attached to silicon through a silicon to carbon linkage, there being preferably a bridge of at least 3 carbon atoms ; separating the silicon atom and the nearest nitrogen atom or atoms. Preferably also, R contains less than about 21 .~ carbon atoms and any oxygen is present in carbonyl and/or ether groups. Examples of the operative R substituents are -(CH2)3MHCH2CH2NH2~ - (CH2)4NHCH2 2 3 -CH .cH.cH3cH2NHcH2cH2NH2r ~ (CH2)3NHCH2 2 2 2 2 r_~ -(CH2)3NHCH2CH2CH(CH2)3NH2 and (CH2)3NH(CH2)2N~CH2CH2COOCH3.
- Each of the X substituents may be an alkoxy or alkoxyalkoxy ' radical having from 1 to 14 carbon atoms, preferably from 1 to 4 carbon atoms. Examples of X radicals are methoxy, iso-propoxy, hexoxy, decyloxy and methoxyethoxy. When present R' may be any alkyl or aryl radical, preferably having less than 19 carbon atoms, e.g. methyl, ethyl, propyl, octyl or phenyl. Preferred as component (B) are the organosilanes wherein R represents the -(CH2)3NHCH2CH2NH2 or the -CH2CHCH3CH2NHCH2CH2NH2 radicals, each X represents an alkoxy radical having from 1 to 4 inclusive carbon atoms and R', when present, represents the methyl radical.
As component (C) there are employed silanes of the general formula R"bSiZ4 b wherein R", Z and _ are as defined hereinabove, or partial hydrolysates of said silanes. In the general formula of the silanes (C) R" may be a!~hydrogen atom or a monovalent hydrocarbon radical or halogenated hydrocarbon radical, for example alkyl, e.g. methyl, ethyl, propyl, butyl, hexyl, decyl, octadecyl, alkenyl e.g. vinyl or allyl, aryl, aralkyl or alkaryl e.g. phenyl, tolyl or , -1091~07 benzyl, halogenoalkyl, e.g. chloromethyl, bromoethyl or
3,3,3-trifluoropropyl and halogenoaryl e.g. chlorophenyl.
- The radical Z may be for example methoxy, ethoxy, propoxy or methoxyethoxy. Preferably Z is methoxy or ethoxy and R", when present, is methyl. Examples of the silanes (C) and their partial hydrolysis products are methyltrimethoxy~
silane, ethyltrimethoxysilane, n-propyltriethoxysilane, phenyltriethoxysilane, tetraethyl orthosilicate, n-butyl orthosilicate, ethyl polysilicate and siloxanes containing both silicon-bonded methyl radicals and methoxy radicals.
It will be understood by those skilled in the art that reference to partial hydrolysis products with regard to the `~ silane components (B) and (C) contemplates also those 7 products where condensation involving hydrolysed radicals ~ has taken place to yield siloxane linkages.
f ' According to a preferred embodiment of this invention the compositions employed to treat synthetic fibres also contain a siloxane condensation catalyst (D) which is a ;`
metal organic compound. We have found that the presence of said catalyst (D) can result in a further improvement in `
the resiliency and other desirable properties of the treated fibres.
A variety of organic metal compounds are known which ;;`
are capable of functioning as siloxane condensation ~ ;
catalysts (D). The best known and preferred for use in the ~ `
process of this invention are the metal carboxylates, for example lead 2-ethyl-hexoate, zinc octoate, cobalt ;
naphthenate, stannous octoate, stannous naphthenate, dibutyltin dilaurate, tin-octyl tin diacetate and dibutyltin diacetate. Particularly preferred are the tin carboxylates.
,,; ~, , . .
- 6 - ~
`'`` `
Other metal organic compoundswhich may be employed include the titaniumand zirconium esters and chelates e.g.
- tetrabutyl tit,anate9 tetra-isopropyl titanate and diisopropoxytitanlum di(ethylacetoacetate)~ diorganotin alkoxides e.g. dibutyltin diethoxide and dioctyltin ; dimethoxide and the diacylpolydlorganostannoxanes eOg.
diacetoxytetraalkyldistannoxane.
The compositions employed in the process of this ~ invention may be applied to the synthetic fibres using any ,, 10 suitable application techniqueg for example by padding or - spraying. The level of application of the composition to the fabric may be varied within wide limits. From about 0.1 to 7 per cent by weight of composition based on the - weight of the fibres represents the preferred application level. Higher proportions of applied composition9 ~or example up to 40% by weight based oll the weight of fibres~
- can be employed. However9 such high application levels are in most cases economically unattractive.
From considerations of bath stability and convenience of application the co~positions of the invention -are best applied in the form of a dispersion or solution in a liquid carrier~ for example as an aqueous emulsion or organic solvent solution. Preferably the compositions are applied from a solution or dispersion in an organic solvent.
Solvents which may be employed include the hydrocarbons and chlorinated hydrocarbonsg for example one or more of toluene, xylene~ benzene, white spirit~ perchloroethylene and trichloroethylene. Suitable solvents or combinations of solvents will be readily apparent to those skilled in the art.
"'f' ' ' 7~3~
; ~ If desired the bath lil`e of the compositions can be extended by incorporating with the composition a compound containing at least one hydroxyl radical attached to an aliphatic carbon atom. Suitabie hydroxylated compounds include organic compounds and polymers, for example~
alkanols e.g. n--hexyl alcohol, octyl alcohol and nonyl alcohol, glycols and poly~lycols and their monoethers e.g.
ethylene glycol, polyethylene glycol 3 ethylene glycol monobutyl etherS diethylene glycol monohexyl ether, mixed polyethylene-polypropylene glycols and condensation product~s of ethylene cxide with polyhydroxyl compounds such as glycerol. The hydroxy radical(s) may also be attached to an organic portion ~hich is in turn attached to an organosilicon portion, for example as in siloxane-oxyalkylene block copolymers. When present the hydroxylated compound is preferably employed in a proportion of from 1 to 15%9 most preferably from 2 to 8%, by weight based on the combined weight of (A)g (B) and (C).
Follo~ling application to ~he fibres the applied organopolysiloxane composition is cured. Cure o~ the -composition may be effected by mere~y exposing the treated ~ibres to the atmosphere at normal a~mospheric temperatures (about 15 - 25C). Although such a procedure may be acceptable in the case of batch processes, curing is preferably expedited (especially in continuous processes) by exposure to elevated temperatures e~g. from 110 - 180C.
Where appropriate, or desired, curing may be preceded by a drying step at a lower temperature.
The relative proportions of the components ~A), (B)g ~C) and (D) present in the compositions are not narrowly ~` --critical. Preferably Erom 0.5 to 15 parts by weight of (B), 1 to 20 parts by weight of (C) and 0.5 to 10 parts by weight ; of (D) are employed per 100 parts of (A). Higher proportions i of (B), for example up to 25 parts by weight can be present but increasing the proportion of (B) results in the treated fibres having a firmer, crisper handle. ~Iigher proportions of (C) and (D) may also be employed, for example up to 25 parts of (C) and up to 15 parts of (D).
The process of this invention can be employed in the treatment of synthetic fibres alone, for example, nylon, polyester and acrylic fibres, blends of synthetic fibres of different types or blends of synthetic fibres and cellulosic fibres. The fibres may be treated in any form where resilience is desired, for example as agglomerations or random fibres, as knitted fabrics or as woven fabrics. The process of this invention is particularly suitable for the treatment of knitted fabrics.
In addition to possessing increased resilience, fibres -treated according to this invention may also exhibit desirable improvements in other properties. Thus increased resiliency will normally be accompanied by an improvement in one or more of, for example, abrasion resistance, handle, tear strength, reduction of snagging in knitted ~abrics and resistance to melting by hot particles. ;
The following Examples illustrate the invention. In ~, the Examples the properties of the treated fibres were measured by the following methods:
Tear Resistance ._ j .
5 Samples 63.5 mm. x 100 mm. in size were cut in the length and in the width of the fabric. Each test ssmple was _ 9 l70 ~
' ` placed on an Elmendorf Tester, with a 20.5 mm. c-1t made with a sharp knife in the cen~re of the test piece at right angl~s to its longer side. I;~e sample was then .pulled lengthwise and the tension (gm.) observed at which tearing occurred~
Crease-recovery rat~
5 Samples 15 mm. x 40 mm. were cut in the length and in the width of the ~a~ric. Each test sample was ~olded into two so ~,hat the longer side is halved. The samples were then placed between two glass plates and allowed to stand for 5 minutes with a 500 g. load on the upper plate.
The weight and upper plate were removc-d and the opening angle a o~ the test piece measured with a crease recovery tester.
Crease recovery rate % ~ x 100 Resilience recovery rate : - .... , . :
Samples of treated fabric (20 cm. x 4 cm.) were ;~
subjected to 50% elongation along the leng~h and width of the fabric in turn. The elongating load was then relax~d and the length of the sample (L2) measured after 5 seconds.
m e resilience recovery rate was ca~culated as 2 L -,L x 100 L
wherein Ll is the original length of the sample.
Hand - The hand o~ the fabric was assessed by touch.
. ~ .
A composition was prepared by mixing by weight Polydimeth~lsiloxane having terminal _SiOH
groups and M.~lt.= 45000 (3000cS at 25C) 90 parts 30*Partial condensate o~ C~13Si(OCH3)3 10 parts : .
- 10 - .. , ;, ., ~, . ~ .
. ! ', 7~
-~~~ *Prepared by refluxing the silane with aqueous sodium hydroxide solution (0.25% by weight MaOII) for 3 hours.
Fifteen parts by weight of the composition was dissolved in 1000 parts of perchloroethylene and to this ' 5 solution were added with stirrin~ 2 parts of (CH30)3Si(CH?)3NHCH2CH2NH2 and 3 parts of a 50% by weight solution in xylene of dibutyltin dioctoate. The resulting solution was then employed to treat by padding samples of knitted fabricg the fibres consisting of a blend o~
polyester fibres (65%) and cotton fibres (35%). The impregnated fabrics were then dried at about 90C and heated for 3 minutes at 150C to cure the applied composition. The weight of cured composition on the fabric (add on) was 3.5% based on the weight of the untreated ~abric.
The properties of the treated samples and of control (untreated) samples were then measured by the methods described above. The results obtained were as follows :
Sample Crease Recovery Tear Resistance Hand Rat-e-r%) Wal~ Course ale Course Control (untreated) 29.3 36 670 520 No flexibility - ~;
rather hard Treated 88.5 92.0 901 782 Soft and springy.
Example ?
.
A composltion was prepared by dissolving the following in 1000 parts of perchloroethylene~
Hydroxylated-polydimethylsiloxane (as Example 1) 12 parts (CH30)3Si(CH2)3NHcH2cH2NH2 1 part Partial condensate of CH3Si(OCH3)3 0.2 '~
Dibutyltin dioctoate 0.6 ~i the parts being expressed by weight. `' The composition so obtained was employed to treat knitted polyester (100%) fabrlc by padding to give a composition pick-up of 220% by weight based on fabric -. weight. The treated fabric was then dried at 80C and heated for 5 minutes at 130C to cure the siloxane.
When the properties of the treated and untreated ~ -~
fabrics were measured as described above the following ;~
results were obtained.
Crease Recoverv Res~ience Recovery ,~ Rate (%~ Rate (%) Hand Wale Course Wale Course Untreated 43.0 87.5 62.5 78.4 Lifeless and rather hard.
Treated 93.9 91.6 lOO 98.9 Soft and springy Example 3 15 A composition was prepared by dissolving the following in 5000 parts of perchloroethylene;
Hydroxylated polydimethylsiloxane (As Example l) 68 parts (CH30~3Si(CH2)3NHCH2cH2NH2 4.8 Partial condensate of CH3Si(OCH3)3 1.2 i-the parts being expressed by weight.
The composition thus obtained was employed to treatsamples of blue nylon tricot knitt,ed fabric by padding to give a composition pick up of 220% by weight based on fabric weight. After drying at 80C for 3 minutes the fabrîc samples were heated at 130C for 3 minutes to cure the siloxane.
When the properties of the treated and untreated samples were measured as described above the following results were obtained.
~(~4~7~7 : Crease Recovery ~. Rate (%) Hand ~ _ .
Wale _o rse .. , . ., '.
Treated 76 95.5 Slippery~ soft and slightly springy.
Untreated 58 96 Very limp.
,' '~. " ~
. .
':
~`,~ '' .
' ' '' ' '"' .' ., ' ',',.
r .,' .
. ~ ' .
X
. ~
, i, .
. ' ~
~ ' .
,
- The radical Z may be for example methoxy, ethoxy, propoxy or methoxyethoxy. Preferably Z is methoxy or ethoxy and R", when present, is methyl. Examples of the silanes (C) and their partial hydrolysis products are methyltrimethoxy~
silane, ethyltrimethoxysilane, n-propyltriethoxysilane, phenyltriethoxysilane, tetraethyl orthosilicate, n-butyl orthosilicate, ethyl polysilicate and siloxanes containing both silicon-bonded methyl radicals and methoxy radicals.
It will be understood by those skilled in the art that reference to partial hydrolysis products with regard to the `~ silane components (B) and (C) contemplates also those 7 products where condensation involving hydrolysed radicals ~ has taken place to yield siloxane linkages.
f ' According to a preferred embodiment of this invention the compositions employed to treat synthetic fibres also contain a siloxane condensation catalyst (D) which is a ;`
metal organic compound. We have found that the presence of said catalyst (D) can result in a further improvement in `
the resiliency and other desirable properties of the treated fibres.
A variety of organic metal compounds are known which ;;`
are capable of functioning as siloxane condensation ~ ;
catalysts (D). The best known and preferred for use in the ~ `
process of this invention are the metal carboxylates, for example lead 2-ethyl-hexoate, zinc octoate, cobalt ;
naphthenate, stannous octoate, stannous naphthenate, dibutyltin dilaurate, tin-octyl tin diacetate and dibutyltin diacetate. Particularly preferred are the tin carboxylates.
,,; ~, , . .
- 6 - ~
`'`` `
Other metal organic compoundswhich may be employed include the titaniumand zirconium esters and chelates e.g.
- tetrabutyl tit,anate9 tetra-isopropyl titanate and diisopropoxytitanlum di(ethylacetoacetate)~ diorganotin alkoxides e.g. dibutyltin diethoxide and dioctyltin ; dimethoxide and the diacylpolydlorganostannoxanes eOg.
diacetoxytetraalkyldistannoxane.
The compositions employed in the process of this ~ invention may be applied to the synthetic fibres using any ,, 10 suitable application techniqueg for example by padding or - spraying. The level of application of the composition to the fabric may be varied within wide limits. From about 0.1 to 7 per cent by weight of composition based on the - weight of the fibres represents the preferred application level. Higher proportions of applied composition9 ~or example up to 40% by weight based oll the weight of fibres~
- can be employed. However9 such high application levels are in most cases economically unattractive.
From considerations of bath stability and convenience of application the co~positions of the invention -are best applied in the form of a dispersion or solution in a liquid carrier~ for example as an aqueous emulsion or organic solvent solution. Preferably the compositions are applied from a solution or dispersion in an organic solvent.
Solvents which may be employed include the hydrocarbons and chlorinated hydrocarbonsg for example one or more of toluene, xylene~ benzene, white spirit~ perchloroethylene and trichloroethylene. Suitable solvents or combinations of solvents will be readily apparent to those skilled in the art.
"'f' ' ' 7~3~
; ~ If desired the bath lil`e of the compositions can be extended by incorporating with the composition a compound containing at least one hydroxyl radical attached to an aliphatic carbon atom. Suitabie hydroxylated compounds include organic compounds and polymers, for example~
alkanols e.g. n--hexyl alcohol, octyl alcohol and nonyl alcohol, glycols and poly~lycols and their monoethers e.g.
ethylene glycol, polyethylene glycol 3 ethylene glycol monobutyl etherS diethylene glycol monohexyl ether, mixed polyethylene-polypropylene glycols and condensation product~s of ethylene cxide with polyhydroxyl compounds such as glycerol. The hydroxy radical(s) may also be attached to an organic portion ~hich is in turn attached to an organosilicon portion, for example as in siloxane-oxyalkylene block copolymers. When present the hydroxylated compound is preferably employed in a proportion of from 1 to 15%9 most preferably from 2 to 8%, by weight based on the combined weight of (A)g (B) and (C).
Follo~ling application to ~he fibres the applied organopolysiloxane composition is cured. Cure o~ the -composition may be effected by mere~y exposing the treated ~ibres to the atmosphere at normal a~mospheric temperatures (about 15 - 25C). Although such a procedure may be acceptable in the case of batch processes, curing is preferably expedited (especially in continuous processes) by exposure to elevated temperatures e~g. from 110 - 180C.
Where appropriate, or desired, curing may be preceded by a drying step at a lower temperature.
The relative proportions of the components ~A), (B)g ~C) and (D) present in the compositions are not narrowly ~` --critical. Preferably Erom 0.5 to 15 parts by weight of (B), 1 to 20 parts by weight of (C) and 0.5 to 10 parts by weight ; of (D) are employed per 100 parts of (A). Higher proportions i of (B), for example up to 25 parts by weight can be present but increasing the proportion of (B) results in the treated fibres having a firmer, crisper handle. ~Iigher proportions of (C) and (D) may also be employed, for example up to 25 parts of (C) and up to 15 parts of (D).
The process of this invention can be employed in the treatment of synthetic fibres alone, for example, nylon, polyester and acrylic fibres, blends of synthetic fibres of different types or blends of synthetic fibres and cellulosic fibres. The fibres may be treated in any form where resilience is desired, for example as agglomerations or random fibres, as knitted fabrics or as woven fabrics. The process of this invention is particularly suitable for the treatment of knitted fabrics.
In addition to possessing increased resilience, fibres -treated according to this invention may also exhibit desirable improvements in other properties. Thus increased resiliency will normally be accompanied by an improvement in one or more of, for example, abrasion resistance, handle, tear strength, reduction of snagging in knitted ~abrics and resistance to melting by hot particles. ;
The following Examples illustrate the invention. In ~, the Examples the properties of the treated fibres were measured by the following methods:
Tear Resistance ._ j .
5 Samples 63.5 mm. x 100 mm. in size were cut in the length and in the width of the fabric. Each test ssmple was _ 9 l70 ~
' ` placed on an Elmendorf Tester, with a 20.5 mm. c-1t made with a sharp knife in the cen~re of the test piece at right angl~s to its longer side. I;~e sample was then .pulled lengthwise and the tension (gm.) observed at which tearing occurred~
Crease-recovery rat~
5 Samples 15 mm. x 40 mm. were cut in the length and in the width of the ~a~ric. Each test sample was ~olded into two so ~,hat the longer side is halved. The samples were then placed between two glass plates and allowed to stand for 5 minutes with a 500 g. load on the upper plate.
The weight and upper plate were removc-d and the opening angle a o~ the test piece measured with a crease recovery tester.
Crease recovery rate % ~ x 100 Resilience recovery rate : - .... , . :
Samples of treated fabric (20 cm. x 4 cm.) were ;~
subjected to 50% elongation along the leng~h and width of the fabric in turn. The elongating load was then relax~d and the length of the sample (L2) measured after 5 seconds.
m e resilience recovery rate was ca~culated as 2 L -,L x 100 L
wherein Ll is the original length of the sample.
Hand - The hand o~ the fabric was assessed by touch.
. ~ .
A composition was prepared by mixing by weight Polydimeth~lsiloxane having terminal _SiOH
groups and M.~lt.= 45000 (3000cS at 25C) 90 parts 30*Partial condensate o~ C~13Si(OCH3)3 10 parts : .
- 10 - .. , ;, ., ~, . ~ .
. ! ', 7~
-~~~ *Prepared by refluxing the silane with aqueous sodium hydroxide solution (0.25% by weight MaOII) for 3 hours.
Fifteen parts by weight of the composition was dissolved in 1000 parts of perchloroethylene and to this ' 5 solution were added with stirrin~ 2 parts of (CH30)3Si(CH?)3NHCH2CH2NH2 and 3 parts of a 50% by weight solution in xylene of dibutyltin dioctoate. The resulting solution was then employed to treat by padding samples of knitted fabricg the fibres consisting of a blend o~
polyester fibres (65%) and cotton fibres (35%). The impregnated fabrics were then dried at about 90C and heated for 3 minutes at 150C to cure the applied composition. The weight of cured composition on the fabric (add on) was 3.5% based on the weight of the untreated ~abric.
The properties of the treated samples and of control (untreated) samples were then measured by the methods described above. The results obtained were as follows :
Sample Crease Recovery Tear Resistance Hand Rat-e-r%) Wal~ Course ale Course Control (untreated) 29.3 36 670 520 No flexibility - ~;
rather hard Treated 88.5 92.0 901 782 Soft and springy.
Example ?
.
A composltion was prepared by dissolving the following in 1000 parts of perchloroethylene~
Hydroxylated-polydimethylsiloxane (as Example 1) 12 parts (CH30)3Si(CH2)3NHcH2cH2NH2 1 part Partial condensate of CH3Si(OCH3)3 0.2 '~
Dibutyltin dioctoate 0.6 ~i the parts being expressed by weight. `' The composition so obtained was employed to treat knitted polyester (100%) fabrlc by padding to give a composition pick-up of 220% by weight based on fabric -. weight. The treated fabric was then dried at 80C and heated for 5 minutes at 130C to cure the siloxane.
When the properties of the treated and untreated ~ -~
fabrics were measured as described above the following ;~
results were obtained.
Crease Recoverv Res~ience Recovery ,~ Rate (%~ Rate (%) Hand Wale Course Wale Course Untreated 43.0 87.5 62.5 78.4 Lifeless and rather hard.
Treated 93.9 91.6 lOO 98.9 Soft and springy Example 3 15 A composition was prepared by dissolving the following in 5000 parts of perchloroethylene;
Hydroxylated polydimethylsiloxane (As Example l) 68 parts (CH30~3Si(CH2)3NHCH2cH2NH2 4.8 Partial condensate of CH3Si(OCH3)3 1.2 i-the parts being expressed by weight.
The composition thus obtained was employed to treatsamples of blue nylon tricot knitt,ed fabric by padding to give a composition pick up of 220% by weight based on fabric weight. After drying at 80C for 3 minutes the fabrîc samples were heated at 130C for 3 minutes to cure the siloxane.
When the properties of the treated and untreated samples were measured as described above the following results were obtained.
~(~4~7~7 : Crease Recovery ~. Rate (%) Hand ~ _ .
Wale _o rse .. , . ., '.
Treated 76 95.5 Slippery~ soft and slightly springy.
Untreated 58 96 Very limp.
,' '~. " ~
. .
':
~`,~ '' .
' ' '' ' '"' .' ., ' ',',.
r .,' .
. ~ ' .
X
. ~
, i, .
. ' ~
~ ' .
,
Claims (15)
1. A process for the treatment of synthetic fibres which comprises applying thereto from 0.1 to 40% based on the weight of the fibres of a composition comprising the product obtained by mixing (A) 100 parts by weight of a polydiorganosiloxane having terminal silicon-bonded hydroxyl radicals and a molecular weight of at least 750, at least 50 per cent of the organic substituents in the polydiorganosiloxane being methyl radicals, any other organic substituents present being monovalent hydro-carbon radicals having from 2 to 30 carbon atoms, (B) 0.5 to 25 parts by weight of an organosilicon compound selected from the group consisting of organosilanes having the general formula RSiR'aX3 a wherein R represents a monovalent radical composed of carbon, hydrogen, nitrogen and, optionally, oxygen which radical contains at least two amine groups and is attached to silicon through a silicon to carbon linkage, R' represents an alkyl radical or an aryl radical, each X represents an alkoxy or alkoxyalkoxy radical having from 1 to 14 inclusive carbon atoms, and a is O or 1, and partial hydrolysates of said organosilanes and (C.) 1 to 25 parts by weight of an organosilicon.
compound selected from the group consisting of silanes having the general formula R"bSiZ4-b, wherein R" is a hydrogen atom, a monovalent hydrocarbon radical or monovalent halogenated hydro-carbon radical, Z is an alkoxy or alkoxyalkoxy radical having from 1 to 4 inclusive carbon atoms and b is 0 or 1 and partial hydrolysates of said silanes, and thereafter curing the applied composition.
compound selected from the group consisting of silanes having the general formula R"bSiZ4-b, wherein R" is a hydrogen atom, a monovalent hydrocarbon radical or monovalent halogenated hydro-carbon radical, Z is an alkoxy or alkoxyalkoxy radical having from 1 to 4 inclusive carbon atoms and b is 0 or 1 and partial hydrolysates of said silanes, and thereafter curing the applied composition.
2. A process as claimed in claim 1 wherein the polydiorganosiloxane (A) is a polydimethylsiloxane having a viscosity at 25°C within the range from 100 to 50,000 cS.
3. A process as claimed in claim 1 wherein in the general formula of organosilane (B) R represents the -(CH2)3NHCH2CH2NH2 or -CH2CHCH3CH2MHCH2CH2NH2 radicals, each X represents an alkoxy radical having from 1 to 4 carbon atoms and R', when present, represents the methyl radical.
4. A process as claimed in claim 1 wherein in the general formula of (C) each Z represents a methoxy or ethoxy radical and R" when present represents the methyl radical.
5. A process as claimed in claim 1 wherein the composition is applied as a dispersion or solution in a volatile organic solvent.
6. A process as claimed in claim 1 wherein the composition comprises from 0.5 to 15 parts by weight of (B) and 1 to 20 parts by weight of (C) per 100 parts by weight of (A).
7. A process as claimed in claim 1 wherein the composition also contains a compound having at least one hydroxyl radical attached to an aliphatic carbon atom.
8. A process as claimed in claim 7 wherein the hydroxylated compound is present in a proportion of from 2 to 8% by weight based on the total weight of (A), (B) and (C).
9. A process for the treatment of synthetic fibres which comprises applying thereto 0.1 to 40% by weight based on the weight of the fibres of a composition comprising the product obtained by mixing (A) 100 parts by weight of a polydiorgano-siloxane having terminal silicon-bonded hydroxyl radicals and a molecular weight of at least 750, at least 50 per cent of the organic substituents in the polydiorganosiloxane being methyl radicals, any other organic substituents present being monovalent hydrocarbon radicals having from 2 to 30 carbon atoms, (B) 0.5 to 25 parts by weight of an organosilicon compound selected from the group consisting of organosilanes having the general formula RSiR'aX3 a wherein R represents a monovalent radical composed of carbon, hydrogen, nitrogen and, optionally, oxygen which radical contains at least two amine groups and is attached to silicon through a silicon to carbon linkage, R' represents an alkyl radical or an aryl radical, each X represents an alkoxy or alkoxyalkoxy radical having from 1 to 14 inclusive carbon atoms, and a is o or 1, and partial hydrolysates of said organosilanes, (C) 1 to 25 parts by weight of an organosilicon compound selected from the group consisting of silanes having the general formula R"bSiZ4-b, wherein R" is a hydrogen atom, a monovalent hydrocarbon radical or monovalent halogenated hydrocarbon radical, Z is an alkoxy or alkoxyalkoxy radical having from 1 to 4 inclusive carbon atoms and b is 0 or 1 and partial hydrolysates of said silanes and (D) up to 15 parts by weight of a siloxane condensation catalyst which is a metal organic compound, and thereafter curing the applied composition.
10. A process as claimed in claim 9 wherein the polydiorganosiloxane (A) is a polydimethylsiloxane having a viscosity at 25°C within the range from 100 to 50,000 cS.
11. A process as claimed in claim 9 wherein R represents the -(CH2)3rNHCH2CH2NH2 or -CH2CHCH3CH2NHCH2CH2NH2 radicals, each X represents an alkoxy radical having from 1 to 4 carbon atoms and R', when present, represents the methyl radical.
12. A process as claimed in claim 11 wherein the composition is applied as a dispersion or solution in a volatile organic solvent.
13. A process as claimed in claim 9 wherein the metal organic compound is a tin carboxylate.
14. A process as claimed in claim 9 wherein there is also incorporated into the composition a compound having at least one hydroxyl radical attached to an aliphatic carbon atom.
15. A proeess as claimed in claim 14 wherein the hydroxylated compound is present in a proportion of from 2 to 8% by weight based on the total weight of (A), (B) and (C).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5860473A GB1485769A (en) | 1973-12-18 | 1973-12-18 | Process for treating fibres |
| GB4572774 | 1974-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1041707A true CA1041707A (en) | 1978-11-07 |
Family
ID=26265652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA216,120A Expired CA1041707A (en) | 1973-12-18 | 1974-12-16 | Process for treating fibres |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3962500A (en) |
| JP (1) | JPS5243954B2 (en) |
| CA (1) | CA1041707A (en) |
| DE (1) | DE2459936C3 (en) |
| FR (1) | FR2254674B1 (en) |
| GB (1) | GB1485769A (en) |
| NL (1) | NL165802C (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2311137A1 (en) * | 1975-05-15 | 1976-12-10 | Rhone Poulenc Textile | FIRE-RESISTANT TEXTILE ARTICLES BASED ON HALOGENATED MODACRYLIC POLYMERS AND PROCEDURE FOR OBTAINING SUCH ARTICLES |
| GB1543157A (en) * | 1975-05-17 | 1979-03-28 | Dow Corning Ltd | Treatment of fibres |
| JPS5287454A (en) * | 1976-01-16 | 1977-07-21 | Toray Silicone Co Ltd | Organopolysiloxane resin composition |
| GB1570983A (en) * | 1976-06-26 | 1980-07-09 | Dow Corning Ltd | Process for treating fibres |
| CA1118163A (en) * | 1977-02-02 | 1982-02-16 | Robert E. Kalinowski | Method for treating synthetic fibers with aminoalkyl-containing polydiorganosiloxanes |
| US4247592A (en) * | 1980-03-12 | 1981-01-27 | Dow Corning Corporation | Method for treating synthetic textiles with aminoalkyl-containing polydiorganosiloxanes |
| DE3014675A1 (en) * | 1980-04-16 | 1981-10-29 | Chemische Fabrik Pfersee Gmbh, 8900 Augsburg | METHOD FOR THE DIMENSIONAL STABILIZATION OF AREA-SHAPED TEXTILE MATERIALS |
| US4311626A (en) * | 1980-09-25 | 1982-01-19 | Toray Silicone Company, Ltd. | Silicone compositions for the treatment of fibers |
| DE3272905D1 (en) * | 1981-10-03 | 1986-10-02 | Dow Corning | Treating textile fibres |
| US4579964A (en) * | 1983-03-31 | 1986-04-01 | Union Carbide Corporation | Alkoxysilyl functional silicones |
| US4721511A (en) * | 1984-10-05 | 1988-01-26 | W. R. Grace & Co. | Leach resistant antimicrobial fabric |
| US4710405A (en) * | 1986-08-25 | 1987-12-01 | Dow Corning Corporation | Adhesion of silicone elastomers obtained from aqueous emulsion |
| DE4117864A1 (en) * | 1991-05-31 | 1992-12-03 | Pfersee Chem Fab | WAITER DISPERSIONS OF POLYSILOXANES |
| DE4330967A1 (en) * | 1993-09-13 | 1995-03-16 | Pfersee Chem Fab | Compositions containing organic silicon compounds for the treatment of fiber materials |
| CA2161712A1 (en) * | 1994-11-03 | 1996-05-04 | Ketan N. Shah | Silane modified elastomeric compositions and articles made therefrom |
| US6239048B1 (en) | 1994-12-28 | 2001-05-29 | Fibermark, Inc. | Light-activated antimicrobial and antiviral materials |
| JP3456956B2 (en) * | 2000-08-10 | 2003-10-14 | 株式会社飾一 | Fiber coating material and coating liquid used for it |
| US6881715B2 (en) * | 2002-11-08 | 2005-04-19 | Optimer, Inc. | Compositions useful as rinse cycle fabric softeners |
| US8844229B1 (en) * | 2013-03-13 | 2014-09-30 | Columbia Insurance Company | Channel anchor with insulation holder and anchoring system using the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3418162A (en) * | 1963-12-07 | 1968-12-24 | Shinetsu Chem Ind Co | Composition of waterproof agent and process for manufacture of waterproof cloth using the same |
| GB1111156A (en) * | 1964-08-04 | 1968-04-24 | Midland Silicones Ltd | Siloxane-coated materials |
| US3436251A (en) * | 1964-08-04 | 1969-04-01 | Midland Silicones Ltd | Process for rendering paper abrasion resistant,adhesive and water-repellent employing siloxane composition |
| GB1174594A (en) * | 1966-10-07 | 1969-12-17 | Midland Silicones Ltd | Improvements in or relating to Siloxane-coated Materials |
| DE2119120B2 (en) * | 1971-04-20 | 1976-07-08 | Wacker-Chemie GmbH, 8000 München | PROCESS FOR PRODUCING STICKY FABRIC REPELLENT COATING |
| US3799919A (en) * | 1972-04-10 | 1974-03-26 | Ici Ltd | Surface treating compositions |
-
1973
- 1973-12-18 GB GB5860473A patent/GB1485769A/en not_active Expired
-
1974
- 1974-12-06 NL NL7415926A patent/NL165802C/en not_active IP Right Cessation
- 1974-12-12 US US05/531,943 patent/US3962500A/en not_active Expired - Lifetime
- 1974-12-16 CA CA216,120A patent/CA1041707A/en not_active Expired
- 1974-12-17 FR FR7441560A patent/FR2254674B1/fr not_active Expired
- 1974-12-17 JP JP14488674A patent/JPS5243954B2/ja not_active Expired
- 1974-12-18 DE DE2459936A patent/DE2459936C3/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7415926A (en) | 1975-06-20 |
| FR2254674B1 (en) | 1977-05-20 |
| NL165802B (en) | 1980-12-15 |
| GB1485769A (en) | 1977-09-14 |
| US3962500A (en) | 1976-06-08 |
| JPS5094295A (en) | 1975-07-26 |
| DE2459936C3 (en) | 1980-08-28 |
| NL165802C (en) | 1981-05-15 |
| DE2459936B2 (en) | 1980-01-03 |
| DE2459936A1 (en) | 1975-06-26 |
| JPS5243954B2 (en) | 1977-11-02 |
| FR2254674A1 (en) | 1975-07-11 |
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