EP0491760A4 - Textile treatment using triazine as binding agent and sulfonated aromatic hydroxy as barrier agent - Google Patents
Textile treatment using triazine as binding agent and sulfonated aromatic hydroxy as barrier agentInfo
- Publication number
- EP0491760A4 EP0491760A4 EP19900913377 EP90913377A EP0491760A4 EP 0491760 A4 EP0491760 A4 EP 0491760A4 EP 19900913377 EP19900913377 EP 19900913377 EP 90913377 A EP90913377 A EP 90913377A EP 0491760 A4 EP0491760 A4 EP 0491760A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- optionally substituted
- textile
- binding agent
- compound
- optionally
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
Definitions
- the present invention relates to a textile treatment composition, methods of treating textiles and to textiles which have been treated.
- Compositions and methods of the present invention are especially suitable to impart stain resist properties to textiles such as wool, cotton and nylon, but the invention is not limited thereto.
- fluorocarbons are used to provide oil and water repellancy to textiles such as fabrics, furnishings, carpets and clothing. The fluorocarbon prevents wetting of the textile thus minimizing contact between the textile and the foreign substance.
- European Patent Application 267681 discloses a method for providing fibrous polyamide materials with stain resistance comprising contacting the fibrous polyamide materials with aqueous solution comprising a normally solid, water-soluble, partially sulfonated resin, which comprises the condensation product of at least one phenolic compound and an aldehyde, and a water-soluble divalent metal salt.
- United States Patent 4592940 discloses a process for imparting stain resistance to a carpet having a pile made of nylon yarn comprising immersing the carpet in an aqueous solution of a selected phenol-formaldehyde condensation product.
- United States Patent 4,501,591 discloses an improvement in certain processes for continuously dyeing polyamide carpets whereby stain resistance is imparted to the carpets during the dyeing process.
- the improvement comprises adding an alkali metal silicate and a sulfonated phenol-formaldehyde condensation product to the dye liquor used in the dyeing process.
- European Patent Application 235 989 discloses an improvement in a process for applying sulfonated naphthol- or sulfonated phenol-formaldehyde condensation products to polyamide textile articles to render them stain resistant, the improvement comprising applying the condensation products at a pH of between 1.5 and 2.5.
- United States Patent 4,940,757 discloses a stain resistant composition which is prepared by polymerizing an a-substituted acrylic acid in the presence of a sulfonated aromatic formaldehyde condensation polymer. It is an object of the present invention to overcome, or at least alleviate, one or more of the difficulties related to the prior art.
- a textile treatment composition including an effective amount of: a textile binding agent which forms a chemical bond with the outer layer of the textile; and a barrier agent which forms a chemical bond with said binding agent and which increases the surface tension of the textile.
- the textile treatment composition may be a textile stain-resistance composition.
- the textile treatment composition is also preferably a composition which provides improved stain-resistant properties and/or improved twist retention and/or improved wearability.
- textile refers to both textiles which are comprised of natural fibres and/or synthetic fibres, for example wool, cotton and nylon and also blends of natural fibres and synthetic fibres.
- the reference to textiles herein includes all textiles to which the method and composition according to the invention is found suitable.
- the term "textile binding agent” refers to an agent which forms a chemical bond with the outer layer of the textile.
- the bond formed is preferably a covalent bond.
- the bond may be formed between the compound and amino groups in the textile.
- the textile binding agent may be a dye inhibitor agent.
- the textile binding agent may be an organic compound.
- the textile binding agent preferably has groups capable of forming a chemical bond to amino groups in the textile to form covalent bonds.
- the textile binding agent and barrier agent may be present in any effective relative amounts.
- the textile binding agent and barrier agent may be present in a weight ratio of from approximately 1:2 to 10:1, preferably approximately 2:1 to 7:1.
- the textile binding agent may be present in amounts of from approximately 35 to 90% by weight preferably approximately 50 to 90% by weight, based on the total weight of the textile treated composition.
- the barrier agent may be present in amounts of from approximately 10 to 65% by weight, preferably approximately 20 to 50% by weight, based on the total weight of the textile treatment composition.
- the textile binding agent is an aryl or alkyl amine.
- the amine may be a primary, secondary or tertiary.
- the binding agent is preferably an aromatic amine.
- binding agent is a substituted triazine.
- said substituted triazine is a monosubstituted dihalotriazine.
- the binding agent may be any compound having groups capable of linking to amino groups in the fibers to form covalent bonds include for example halopyrimidinyl, haloquinoxalyl, haloacrylamido, vinylsulfo or any other groups that can produce these groups.
- the binding agent may be a compound having anionic groups such as sulfonate, carboxylate, sulfate, phosphate.
- the textile binding agent is a substituted triazine which may take the form shown in formula I:
- R is a polar substituent, preferably hydrogen, halogen, hydroxy, or an organic polar substituent.
- R is preferably a substituted phenyl, benzyl or napthyl group. Suitable substituents on the phenyl, benzyl or napthyl group include hydrogen, hydroxy, halogen or any organic radical.
- R is R,X wherein R. may be any polar substituent. Suitable substituents include hydrogen, hydroxy, halogen or any organic radical. In a further preferred embodiment R, is a sulphophenyl or sulfonapthyl group;
- X may be oxygen or NR_ wherein R ⁇ is hydrogen or a lower alkyl group or any other suitable organic radical; Hal may be any suitable halogen. Hal is preferably Cl.
- the textile binding agent may include a compound having the general formula (la)
- Alkyl groups and the alkyl moiety or alkoxy groups may be in the form of straight or branched chains, and preferably contain 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms.
- the alkyl group may be selected from methyl, ethyl, propyl (n- and iso-propyl) and butyl (n-sec-, iso- and tert butyl). Cycloalkyl groups, which are preferably
- C__ g cycloalkyl groups include cyclohexyl and cycloalkylalkyl groups, which are preferably C ⁇ , — c cycloalkyl (C,_.)alkyl groups, include cyclopropylethyl.
- Alkenyl and alkynyl groups preferably contain 2 to 6, more preferably 2 to 4, carbon atoms in the form of straight or branched chains, for example ethenyl, allyl and propargyl.
- the aryl group is preferably phenyl.
- the aralkyl group may be benzyl, phenylethyl or phenyl-n-propyl.
- Optionally substituted alkyl groups include haloalkyl, hydroxyalkyl, alkoxyalkyl.
- the optionally substituted aryloxyalkyl group may be an optionally substituted phenoxyalkyl.
- the optionally substituted heteroaryloxalkyl groups include pyridinyl- and pyrimidinyloxyalkyl.
- the optionally substituted alkenyl group includes optionally substituted phenylalkenyl, preferably optionally substituted phenylethenyl.
- Optionally substituted arylalkoxy includes optionally substituted benzyloxy.
- Substituents which may be present in any optionally substituted aryl or heteroaryl moiety include one or more of the following: halogen preferably fluorine, chlorine and bromine; C, 4 alkyl, preferably methyl and ethyl; ( c ⁇ _ alkoxy, preferably methoxy; halo ( c ⁇ _ ) alkyl preferably trifluoromethyl; halo C,_ 4 alkoxy preferably trifluoromethoxy; C I- ⁇ alkylthio preferably methylthio; C - _ ⁇ alkoxy ( c ⁇ _ ) alkyl, C 3_ f i cycloalkyl; C 3 _ 6 cycloalkyl-(C._.) alkyl; aryl preferably phenyl; aryloxy preferably phenyloxy; aryl ( c ⁇ _4) alky
- Optionally substituted amino, acylamino and acyloxy groups include the groups -NR 1R2, -NHCOR1
- R1 and R2 are as defined above. It is preferred that at least one of A, B, D and
- E is an alkyl group, such as methyl, but it can be in any relationship (ortho, meta or para) to the sulfonic acid group W, which can also be in any position on the ring.
- the binding agent includes a compound of formula lb:
- X is NR, wherein R_ is hydrogen or
- binding agent (a) includes a compound selected from: cl
- the textile binding agent includes the compound or mixture of compounds sold under the trade designation "Paranyl B” which includes the above compounds, or "Sandospace R” which is the sodium salt of
- carrier agent refers to a compound which forms a chemical bond with the binding agent and which increases the surface tension of the textile.
- the compound preferably forms a covalent bond with the binding agent.
- the compound preferably has polar substituents in order to assist in the repulsion of compounds which may stain the textile.
- Barrier agent is preferably a substituted aromatic hydroxy compound.
- said substituted aromatic hydroxy compound is a sulfonated aromatic hydroxy compound.
- barrier agent (b) includes a compound of formula II;
- R,, R 4 and _ may be the same or different and are polar groups.
- Preferred substituents are any sulphoalkyl
- Alkyl groups and the alkyl moiety or alkoxy groups may be in the form of straight or branched chains, and preferably contain 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms.
- the alkyl group may be selected from methyl, ethyl, propyl (n- and iso-propyl) and butyl (n-sec-, iso- and tert butyl).
- Cycloalkyl groups which are preferably C 3 _ 6 cycloalkyl groups, include cyclohexyl and cycloalkylalkyl groups, which are preferably C 3 _ c cycloalkyl (C._ 4 )alkyl groups, include cyclopropylethyl.
- Alkenyl and alkynyl groups preferably contain 2 to 6, more preferably 2 to 4, carbon atoms in the form of straight or branched chains, for example ethenyl, allyl and propargyl.
- the aryl group is preferably phenyl.
- the aralkyl group may be benzyl, phenylethyl or phenyl-n-propyl.
- Optionally substituted alkyl groups include haloalkyl, hydroxyalkyl, alkoxyalkyl.
- the optionally substituted aryloxyalkyl group may be an optionally substituted phenoxyalkyl.
- the optionally substituted heteroaryloxalkyl groups include pyridinyl- and pyrimidinyloxyalkyl.
- the optionally substituted alkenyl group includes optionally substituted phenylalkenyl, preferably optionally substituted phenylethenyl.
- Optionally substituted arylalkoxy includes optionally substituted benzyloxy.
- Substituents which may be present in any optionally substituted aryl or heteroaryl moiety include one or more of the following: halogen preferably fluorine, chlorine and bromine; C,_ 4 alkyl, preferably methyl and ethyl; (C, 4 ) alkoxy, preferably methoxy; halo (C 1-4 alkyl preferably trifluoromethyl; halo C, 4 alkoxy preferably trifluoromethoxy; C I- ⁇ alkylthio preferably methylthio; C - > _ ⁇ alkoxy ( ( ⁇ - _- ⁇ alkyl, C 3 _ fi cycloalkyl; C 3 _ ⁇ cycloalkyl-(C, 4 ) alkyl; aryl preferably phenyl; aryloxy preferably phenyloxy; aryl ⁇ c ⁇ _ 4 ⁇ al
- R 1 and R2 may be independently hydrogen, C, 4 alkyl,
- Optionally substituted amino, acylamino and acyloxy groups include the groups -NR 1R2, -NHCOR1
- Z is an electron drawing group.
- Z is preferably R fi -0-Rrent wherein R fi and R_ may be the same or different and may be any organic radical.
- Z may be an ether group.
- Z is more preferably SO-.
- barrier agent includes the compound or compounds sold under the trade designation "Cibatex RN".
- barrier agent includes the condensation product of napthalene sulphonic acid, di-hydroxy-di-phenylsulphone and formaldehyde. During the condensation different chemical substances are formed so an exact formula cannot be given.
- the barrier agent may include the compound or mixture of compounds sold under the trade designation "Thiotan WPN Liquid” .
- barrier agent includes the compound or mixture of compounds sold under the trade designation "Nylofixan P” which is the condensation product of M-xylene sulphonic acid (ammonium salt), dihydroxy-diphenylsulphone and formaldehyde, "Mesitol NBS” which is the condensation product of dihydroxy-diphenyl sulphone and its sulphonated derivative with formaldehyde.
- “Nylofixan P” is the condensation product of M-xylene sulphonic acid (ammonium salt), dihydroxy-diphenylsulphone and formaldehyde
- Mesitol NBS which is the condensation product of dihydroxy-diphenyl sulphone and its sulphonated derivative with formaldehyde.
- the fibre treatment composition may further include a solvent for the textile binding agent and/or barrier agent.
- a textile treatment composition including: a textile binding agent which forms a chemical bond with the outer layer of the textile; a barrier agent which forms _ a chemical bond with said binding agent and which increases the surface tension of the textile; and a solvent.
- Suitable solvents include aqueous and organic solvents.
- an aqueous solvent is used.
- the solvent is water of similar quality to that normally used in textile dyeing.
- the solvent used is a common solvent to that used in any other processes which may be used to treat the textile, such as dyeing.
- the composition and for example a dye which may be used to treat the textile may both be placed in the same solution.
- the composition of the present invention further includes a salt.
- the salt may include an alkali metal salt, for example sodium chloride (common salt) . It has surprisingly been found that the treatment with common salt during or subsequent to treatment with the composition in accordance with the method of the present invention increases the stain resistance imparted to the textile. Accordingly in a further aspect of the present invention there is provided a textile treatment composition including an effective amount of: a textile binding agent which forms a chemical bond with the outer layer of the textile; a barrier agent which forms a chemical bond with said binding agent and which increases the surface tension of the textile; and a salt.
- composition of the invention may be buffered to a desired pH.
- composition is buffered in solution to have a pH less than
- composition is buffered such that it has a pH in solution of between 3.0 and 6.0.
- the present invention also provides a method of treatment of a textile to render it stain resistant comprising: providing a textile; and contacting the textile with a textile treatment composition including a textile binding agent which forms a chemical bond with the outer layer of the textile; a barrier agent which forms a chemical bond with said binding agent and which lowers the surface tension of the textile; for a time sufficient and at a temperature sufficient to permit reaction therebetween.
- This method is particularly useful in treating wool of all types including but not limited to knitting wool and wool carpet; and other textiles such as nylon and cotton.
- the compositon used in tfie method includes a ratio of textile binding agent to barrier agent of from 1:2 to 10:1.
- the preferred ratio will depend on the textile binding agent and barrier agent used and also the textile to be treated. The ratio may be established by the person skilled in the art.
- a ratio of 2:1 is suitable.
- a ratio of between 6:1 and 7:1 is suitable, and 6.66:1 is especially suitable.
- the term "wool/nylon blends" includes for example 80% wool to 20% polyamide and 70% wool to 30% polyamide which are commonly used in the carpet trade.
- composition When the composition is to be applied to nylon it has been found that when the compound or compounds sold under the trade designation "Paranyl B” is used as the textile binding agent that a ratio of 0.8:1 is suitable. It has been found that when the compound or compounds sold under the trade designation "Sandospace R” is used as the textile binding agent that a ratio of between 2:1 and 3:1 is suitable and 2.66:1 is especially suitable.
- composition is preferably applied to the textile in an amount of between about 2 to about 35%, preferably about 5 to about 10% of composition to weight of textile to be treated.
- kilograms of a wool or wool/nylon blend carpet may advantageously be treated using a solution containg 0.75 kilograms of the compound or compounds sold under the trade designation "Paranyl B” agent and 0.375 kilograms of barrier agent, or 2.5 kilograms of the compound or compounds sold under the trade designation "Sandospace R" and 0.375 kilograms of binding agent.
- the treatment solution which is used to treat the textile in accordance with the above method is heated.
- the treatment solution is preferably heated to and maintained at a temperature within a range of about 85°C to about 105°C. More preferably the treatment solution is heated to and maintained at a temperature of about 100°C. It will be appreciated that for textiles other than wool different temperatures may be used. It will also be appreciated that the temperature should not be so high as to damage the wool or other textile.
- the textile to be treated is placed in the treatment solution including the composition, for a time sufficient to allow the composition to act upon the textile. It will be appreciated that time will be dependant upon the nature of the textile and will also be temperature and pressure dependant.
- the treatment time may be established by a person skilled in the art according to the type of textile to be treated and the temperature and pressure used. By way of example, wool placed in the above referred to most preferred solution at 100°C will require about 3 to 6 minutes.
- the treatment solution is provided by mixing the composition including binding agent and barrier agent as described above, together with an already existing solution used in the manufacturing process. Preferably the existing treatment solution meets the above preferred temperature, pH, solvent, pressure and other relevant requirements.
- the treatment solution may be provided by placing the composition including textile binding agent and barrier agent together with the dye solution used to dye the textile.
- the textile may then be treated with the composition of the present invention and dyed at the same time.
- the textile treatment according to the present invention can be done during the dyeing either from an exhaust bath or in a continuous dyeing process.
- the composition of the present invention may be simply added to the dye liquor and the dyeing may be carried out as normal.
- the stain resist finish is preferably applied as a dyebath post treatment to avoid partial blocking of the dyes.
- the composition of the present invention may be added to the boiling dyebath at the end of the dyeing process and the dyebath may be kept boiling for a sufficient time to effect the treatment of the textile according to the present invention.
- the dyebath may be kept boiling for approximately a further 30 minutes.
- the method of the present invention could be carried out in a "closed" or at least “partially closed” system is which the solution including the composition is applied to the textile under pressure. It will be appreciated that the pressure should not be sufficient that damage would be caused to the textile. It will be further appreciated that the temperature and composition reaction time will vary in relationship with the pressure used.
- the textile treated in the manufacturing process is preferably treated with a common salt application liquor during or subsequent to dyeing.
- the treatment with the common salt application liquor may take place concurrent with or subsequent to treatment with the composition in accordance with the method of the present invention.
- Most preferably the common salt application liquor is applied at the same time as the treatment composition.
- the concentration of common salt may be about 4 to 30% to the weight of the textile to be treated, preferably 4 to 10% and most preferably 4 to 5%.
- the textile may be treated either by applying the textile binding agent or barrier agent to the textile at a time different to the time at which the other agent is applied to the textile.
- the textile will be treated in a solution including textile binding agent and at a later stage in the treatment process a solution including barrier agent is used to treat the textile; or vice versa.
- the textile is treated with a solution including textile binding agent concurrent with dyeing of the textile and barrier agent is included subsequent to the dyeing process.
- the textile is preferably treated with a common salt application liquor concurrent with or subsequent to treatment with the barrier agent. It has been found that the following are exemplary conditions in which the method of the present application may be performed;
- the textile treatment method of the present invention is performed concurrently with the dyeing process.
- An aqueous solution consisting of acid levelling dye stuffs, textile binding agent, preferably 7.5% "Paranyl B” or 25% “Sandospace R", barrier agent, preferably 3.75%, and common salt, preferably 5%, is buffered to a pH of between 3.0 and 6.0 depending on the required dyeing conditions.
- the solution is applied to the wool or wool/nylon blend by any commonly used technique such as padding, flooding, spraying or printing. The application rates mentioned above are based on the weight of textile treated.
- the textile is then steamed at between 95°C and 100°C for a sufficient time to fix the dye stuff and the textile treatment composition, usually about 3 to 6 minutes.
- the textile is then rinsed and dried.
- a batch wise exhaustion of the dye stuff and textile treatment composition may also be conducted concurrently.
- the textile binding agent preferably 7.5% "Paranyl B” or 25% “Sandospace R”
- barrier agent preferably 3.75%
- common salt preferably 5%
- the second chlorine is postulated, is displaced by another nucleophile, such as the phenolic constituents of the barrier agent.
- another nucleophile such as the phenolic constituents of the barrier agent.
- the textile binding agent is covalently and irreversably bound to the textile and the barrier agent is covalently and irreversably bound to the binding agent, the textile is effectively coated with an organic structure containing numerous highly polar acidic groups (i.e. SOgH
- Such groups would present electrostat c repuls on to incoming staining molecules and not allow them to bind strongly.
- wool the usual wool protein structures would be effectively protected by a veneer of polymer-like structures.
- the original dye molecules applied prior to or together with the composition of the present invention would remain fast and not be destabilised as they would be embedded in the above coating.
- the present invention also provides a textile having improved stain-resist properties, and/or improved twist retention and/or improved wearability.
- the textile according to the present invention comprises a textile which has been treated with the compostion of the present invention.
- the textile of the invention has been treated according to the method of the present invention as described above.
- the present invention also provides a textile treatment kit comprising: a first component textile binding agent which forms a chemical bond with the outer layer of the textile, in a suitable container; and a second component barrier agent which forms a chemical bond with said binding agent and which increases the surface tension of the textile, in a suitable container.
- Dye No 40 which is an artificial colorant commonly added to foods, beverages, medicines, cosmetics etc.
- Example 2 As can be seen above, the treated carpet showed a very good stain block effect on a wool carpet when tested with FD & C Red 40. To the best of the Applicants knowledge, there is no compound on the market which has the same effect.
- Example 2 To the best of the Applicants knowledge, there is no compound on the market which has the same effect.
- 3M carpet stain release test 1 was used. This test is designed to provide a simple standard method for measuring and rating the effectiveness of removing stains from carpet.
- Test pH of staining test solution It must be between 2.5-4.0. Record pH value. Water temperature should be 21 ⁇ 3°C.
- the 3M carpet stain release test 1 was also carried on a nylon carpet which had been treated with a composition comprising 1.8% "Paranyl B", 1.0% “Thiotan WPN” liquid, and 4% common salt. The carpet passed the 3M carpet stain release test 1.
- Example 5
- a rating of 4 is considered to be very good, only very slight colouration on the tips of yarn.
- This example illustrates the improved twist retention and wearability of a carpet sample which has been treated with the textile treated treatment composition of the present invention.
- a 100% wool cut pile carpet weighing 50 ounces per square yard was tufted on a 1/10 Guage Tufting machine. Half of this carpet was dyed using acid levelling dyes on an industry standard continuous dyeing line. The other half of the carpet was dyed under the same conditions but incorporating the textile treatment composition of the present invention in with the dyeing liquor. The two samples of carpet were then subjected to 8600 cycles on a hexapod wear testing machine and each sample was then rated for appearance retention using a grey scale rating system from 1 to 5 in which 5 indicates no change in appearance. The results are provided in
- the following example illustrates the superior stain resist properties of a wool carpet which has been treated with the textile treatment composition of the present invention.
- Table 7 illustrates the results of staining trials on a wool carpet. The results are expressed as total colour difference (WE) . A conversion to Grey Scale Ratings is also provided.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPJ629189 | 1989-09-11 | ||
AU6291/89 | 1989-09-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0491760A1 EP0491760A1 (en) | 1992-07-01 |
EP0491760A4 true EP0491760A4 (en) | 1992-07-08 |
Family
ID=3774182
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19900913377 Withdrawn EP0491760A4 (en) | 1989-09-11 | 1990-09-11 | Textile treatment using triazine as binding agent and sulfonated aromatic hydroxy as barrier agent |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0491760A4 (en) |
JP (1) | JPH05500395A (en) |
NZ (1) | NZ235253A (en) |
WO (1) | WO1991003593A1 (en) |
ZA (1) | ZA907220B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5516337A (en) * | 1992-09-02 | 1996-05-14 | Minnesota Mining And Manufacturing Company | Chemical system for providing fibrous materials with stain resistance |
JP2005281952A (en) * | 2004-03-05 | 2005-10-13 | Toray Ind Inc | Nylon fiber structure and method for producing the same |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4842188A (en) * | 1971-10-08 | 1973-06-19 | ||
CH556943A (en) * | 1972-10-23 | 1974-12-13 | ||
US4592940A (en) * | 1983-12-16 | 1986-06-03 | Monsanto Company | Stain-resistant nylon carpets impregnated with condensation product of formaldehyde with mixture of diphenolsulfone and phenolsulfonic acid |
US4501591A (en) * | 1983-12-27 | 1985-02-26 | Monsanto Company | Process for conveniently providing stain-resistant polyamide carpets |
CA1264505A (en) * | 1986-02-14 | 1990-01-23 | E.I. Du Pont De Nemours And Company | Method for producing stain resistant polyamide fibers |
CA1339878C (en) * | 1986-10-14 | 1998-05-26 | John Cheng-Chung Chang | Treating fibrous polyamide articles |
US4737155A (en) * | 1987-06-05 | 1988-04-12 | The Goodyear Tire & Rubber Company | Stabilizers for improving the ozone fastness of dyes with oxadiazine-4-thione or triazine-4-thione compounds |
EP0345212A1 (en) * | 1988-05-04 | 1989-12-06 | Ciba-Geigy Ag | Process to prevent yellowing of polyamide fibres finished with stain-proofing agents |
-
1990
- 1990-09-11 JP JP2512328A patent/JPH05500395A/en active Pending
- 1990-09-11 ZA ZA907220A patent/ZA907220B/en unknown
- 1990-09-11 EP EP19900913377 patent/EP0491760A4/en not_active Withdrawn
- 1990-09-11 NZ NZ235253A patent/NZ235253A/en unknown
- 1990-09-11 WO PCT/AU1990/000410 patent/WO1991003593A1/en not_active Application Discontinuation
Non-Patent Citations (2)
Title |
---|
No further relevant documents disclosed * |
See also references of WO9103593A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO1991003593A1 (en) | 1991-03-21 |
ZA907220B (en) | 1991-07-31 |
JPH05500395A (en) | 1993-01-28 |
NZ235253A (en) | 1993-02-25 |
EP0491760A1 (en) | 1992-07-01 |
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