US3637427A - Process for imparting high-elastic recovery to extensible knitted or woven fabrics and product obtained - Google Patents
Process for imparting high-elastic recovery to extensible knitted or woven fabrics and product obtained Download PDFInfo
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- US3637427A US3637427A US3637427DA US3637427A US 3637427 A US3637427 A US 3637427A US 3637427D A US3637427D A US 3637427DA US 3637427 A US3637427 A US 3637427A
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- Prior art keywords
- fabric
- naphthenate
- elastic recovery
- yarn
- zirconium
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- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000011084 recovery Methods 0.000 title abstract description 40
- 239000002759 woven fabric Substances 0.000 title abstract description 10
- 239000004744 fabric Substances 0.000 claims abstract description 58
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 39
- -1 polysiloxane Polymers 0.000 claims abstract description 38
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims abstract description 15
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 15
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003502 gasoline Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 2
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 claims description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- ZCGHEBMEQXMRQL-UHFFFAOYSA-N benzyl 2-carbamoylpyrrolidine-1-carboxylate Chemical compound NC(=O)C1CCCN1C(=O)OCC1=CC=CC=C1 ZCGHEBMEQXMRQL-UHFFFAOYSA-N 0.000 claims description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
- 239000003863 metallic catalyst Substances 0.000 claims description 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005609 naphthenate group Chemical group 0.000 claims description 2
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 claims description 2
- BPYXFMVJXTUYRV-UHFFFAOYSA-J octanoate;zirconium(4+) Chemical compound [Zr+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O BPYXFMVJXTUYRV-UHFFFAOYSA-J 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 2
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 claims description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 2
- OEERILNPOAIBKF-UHFFFAOYSA-J zirconium(4+);tetraformate Chemical compound [Zr+4].[O-]C=O.[O-]C=O.[O-]C=O.[O-]C=O OEERILNPOAIBKF-UHFFFAOYSA-J 0.000 claims description 2
- 238000005406 washing Methods 0.000 description 10
- 239000000835 fiber Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000972773 Aulopiformes Species 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
-
- 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
- Y10T442/2377—Improves elasticity
Definitions
- ABSTRACT The present invention relates to a process for imparting highelastic recovery to extensible knitted or woven fabrics by treating the fabric with an organic solution of low-viscosity containing a hydroxy-terminated dimethylpolysiloxane, a methylhydrogen polysiloxane and an organometallic catalyst.
- the fabric used should have a relatively low extensibility.
- An object of the present invention is therefore to provide a process for imparting extensible knitted or woven fabrics with high-elastic recovery in both dry and wet states.
- a process for imparting extensible knitted or woven fabrics with highelastic recovery which comprises treating the fabric with an organic solution having a viscosity of less than 400 c.p.s. and containing a hydroxy-terminated dimethylpolysiloxane, methylhydrogen polysiloxane and an organic metal catalyst so that said hydroxy-terminated dimethylpolysiloxane and methylhydrogen polysiloxane can be deposited in an amount of l to 5 percent (as solid) by weight of fabric in said fabric, and curing the same at a temperature of from 120 to 200 C.
- the knitted or woven fabrics which may be used for the purpose of the present invention have preferably an extensibility of more than 20 percent and include e.g., those composed of textured yarns made of synthetic fibers such as fibers of polyamide, polyester, polyacrylonitrile, polyolefin, polyvinylalcohol etc.
- textured yarns include crimped yarns such as twist-set-untwist yarns, false twist yarn, stuffer box-treated yarn, edge-crimped yarn, air-jetted yarn and mixtures thereof.
- extensibility denotes the percentage of elongation of a sample piece having a width of 5 cm. and a length of cm. when burdened with a load of 1.5 kg. based on the original length of the sample piece.
- the treating solution used for the process of the present invention may have the following composition:
- a hydroxy-terminated dimethylpolysiloxane having the following general formula:
- n is an integer from 15 to 50.
- An organometallic catalyst for example, zinc caprylate, tin caprylate, zirconium caprylate, dibutyl tin dilaurate, dibutyl tin dicaprylate, dibutyl tin diacetae, dibutyl tin oxide, alkyl titanate, zinc naphthenate, tin naphthenate, zirconium naphthenate, ferric naphthenate, cobalt naphthenate, zinc formate, zirconium formate, zinc acetate, zirconium acetate etc.
- organic solvents which may be used for the purpose of the present invention include hydrocarbons having carbon atoms of not more than 10 such as petroleum benzine,- gasoline, benzene, toluene, xylene, trichloroethylene, perchloroethylene and ethylacetate.
- additives such as e.g., sodium alcoholate, ester silane, polyalkyl silicate etc.
- additives serve to improve the elastic recovery and washability of the final products because they are capable of cross-linking with aforesaid polysiloxanes so as to increase the degree of the polymerization.
- Sodium alcoholates are represented by the general fonnula: RONa, in which R is an alkyl group having less than five carbon atoms.
- Polyalkyl silicate is a polymer obtained by partially hydrolyzing organosilicates represented by the general formula: (R0),Si, in which R is an alkyl group having less than five carbon atoms.
- Ester silanes are represented by the general formula:
- the treating solution of the present invention must be applied to the fibers uniformly, and for this purpose, the dimethylpolysiloxane of the present invention should be dissolved in the organic solvent so as to give a low viscosity. It is essential that the viscosity of the treating solution at 20 C. used in the present invention is less than 400 c.p.s. (as measured by using a conventional rotary viscometer [type BL available from Tokyo Keiki Seizo-sho. K.K., Japan]). If the viscosity is higher than that level, the liquid is liable to remain only the surface of the fabric, thus covering the interfiber voids so that it hardly is possible to obtain the desired elastic recovery.
- the preferred blending proportions of the components are for example as follows:
- methylhydrogen polysiloxane Five to 30 (preferably 10 to 25) weight parts of methylhydrogen polysiloxane and 0.1 to 5 weight parts of organometal catalyst per weight parts of dimethyl polysiloxane.
- the organic solvent should be used in sufficient amounts so that the liquid viscosity will stay below 400 c.p.s.
- the amount of deposition of the organopolysiloxanes should be 1.0 to 5.0 percent by weight of the fabric. If such amount is less than 1.0 percent, unsatisfactory elastic recovery may be obtained, while if it is more than 5.0 percent, the feel of and extensibility of the fabric may be deteriorated.
- the fabric After treating the fabric, it is dried e.g., at 50 to C. under lowest possible tension to remove the organic solvent.
- the fabric is then cured e.g., at 120 to 200 C. under lowest possible tension thereby effecting the cross-linkage of the organopolysiloxanes with the fibers and the reaction between each of the organopolysiloxanes. It is desirable to treat the fabric under minimum tension. Such lowtension treatment will permit the extensibility prior to the treatment to be carried over to the resultant article.
- the article thus obtained has a high-elastic recovery never seen in conventional bulky articles and its elasticity can be equal to that of elastomer fibers. It is thus possible to obtain articles having high-elastic recovery being equal to that of the elastomer fibers by subjecting extensible fabric to the treatment according to the present invention. Articles thus obtained are free from deterioration of color fastness and washability, and can minimize production costs.
- the extensibility was determined by using a tensile tester, Autograph P-loo (available from Shimazu Seisakusho, KK, Japan) under the following conditions:
- the elastic recovery rate is the percentage of the recovery of the elongation during the reluxed state and can be defined as follows:
- EXAMPLE 1 Two-stage interlock fabric (jersey) and twill-knitted fabric knitted by using nylon bulky yarn (70 deniers/Z filaments) were respectively immersed in a solution having the following composition (viscosity: 40 c.p.s.) and were squeezed to give polysiloxanes (as solid) amounting to 0.5%, 1.0%, 3.0%, 5.0%, and 7.0% by weight ofthe fabric respectively:
- composition of the solution part by weight Dimethyl polysiloxane 2.7 Mcthylhydrogcn polysiloxane 0.3 Phcnyllrielhoxysilune 0.03 Dibutyl tin tliluurute 0.03 'lrichlumclhylenc 96.94
- the trichloroethylene was removed off by heating at 80 C.
- the fabric was then cured by using a short-loop baking machine at l 55 C. for 3 min. under lowest possible tension.
- Amounts greater than 5 percent will decrease the extensibility sharply and the feeling of the treated fabrics will also largely deteriorate.
- the elastic recovery in dried state is likely to be almost independent on the changes of the deposited amounts of the polysiloxanes, while the elastic recovery in wet state significantly decreases when the deposited amount of polysiloxanes is less than 1 percent by weight of the fabric.
- the antipilling property shown in tables l and 2 was determined by means of the method according to Japanese Industrial Standard (JlS) L-l076-l967, which is similar to the so-called lCI method. The antipilling property will be advantageous when the deposited amount of the polysiloxanes is more than 1 percent by weight of the fabric.
- EXAMPLE 2 A similar process to that described in example 1 was performed with the exception of using the polysiloxanes in such amount that they would be deposited in the fabric in an amount of 2 percent by weight of the fabric (calculated as solid).
- the amount of trichloroethylene was changed stepwise so as to give the viscosities of the solution of IO, 40, I20, 250, 400, 500 and 1,000 c.p.s., respectively.
- the obtained results are shown in tables 3 and 4. The results obtained are likely to be substantially independent on the treating time.
- a three-stage interlock fabric of nylon bulky yarn (70 deniers/Z filaments; jersey) was immersed in a treating solution having the following composition, and was then dried at The washing test was performed by using a Hitachi SC-AT Model 3 Washing Machine (commercial product available from Hitachi Seisaku-sho l(.l(., Japan) and washed in a solution of l g./l. of Emal (an anionic washing agent available 800 C. to remove off the trichloroethylena from Kao Sekken K.l(., Japan) at 40 C. for minutes.
- Hitachi SC-AT Model 3 Washing Machine commercial product available from Hitachi Seisaku-sho l(.l(., Japan) and washed in a solution of l g./l. of Emal (an anionic washing agent available 800 C. to remove off the trichloroethylena from Kao Sekken K.l(., Japan) at 40 C. for minutes.
- the fabric obtained also had The fabflc was cured at 160 for under 3 lowest improved extensibility and elastic recovery as shown in table possible tension by using the conventlonal short-loop baking 7, machine to yield a fabric having an improved extensibility, and elastic recovery as shown in table 5.
- Table A Extensibility (percent)
- B Elastic recovery (percent) TABLE 5 2 5 TABLE 7 Extensi- Elastic Condition Sample bility Recovery C diti S l A 8 y Nontrealed -2 01 Dry Nontreated 48.2 70.2 Treated 92.6 91.2 Treated I293 92.3 Wet Nontreated 47.1 69.8 Wet Nontreated 47.1 69.8 Treated ll4.2 90.9 Treated I 30.1 91.7
- EXAMPLE 6 A similar treatment to that described in example 4 was carried out with the exception of substituting diethoxy pen- A f' 'reatmeht that dhschbed m exhmple 3 was h tasilane for the metallic sodium ethylate.
- the properties of the fhnhed using the y m s the except'oh of employ mg 40 fabric thus obtained are shown in table 8.
- No washing test was the following treatlng solutions: made Key to Table Composmon of the salmon (part by we1ght) A. Extens1b1l1ty (percent Dimethylpolysilowne B.
- a Extensibility b f washing (percent) 1. A process for imparting high-elastic recovery to extensi- Extensibmty ft washing five times (percent) ble bulky knitted or woven fabrics composed of textured yarns Elastic recovery before washing (Percent) made of synthetic fibers having an extensibility of more than D. Elastic recovery after washing five times (percent) 20 phmehh h h comphses apply 3 to the fhhhc ah orgamc solut1onconta1n1r1g l.
- n is an integer not less than 500
- a methylhydrogen polysiloxane having the general formuin which n is an integer from 15 to 50, the ratio of methylhydrogen polysiloxane to dimethylpolysiloxane is to 30 parts by weight of methylhydrogen polysiloxane based upon 100 parts by weight of dimethylpolysiloxane;
- an organic metallic catalyst dissolved in an organic solvent capable of dissolving said polysiloxanes and utilized in an amount to give a solution having a viscosity of not more than 400 c.p.s. so that L0 to 5.0 percent by weight of the fabric, of polysiloxanes are deposited as solid on said fabric, and then curing the polysiloxane treated fabric at an elevated temperature.
- said fabric is composed of textured yarn selected from the class consisting of polyamide, polyester, polyacrylonitrile, polyolefin, polyvinylalcohoi and mixtures thereof.
- treating solution further contains at least one member selected from the class consisting of sodium alcoholate, ester silane and polyalkyl silicate.
- said organometallic catalyst is at least one member selected from the class consisting of zinc caprylate, tin caprylate, zirconium caprylate, dibutyl tin dicaprylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, alkyl titanate, zinc naphthenate, tin naphthenate, zirconium naphthenate, ferric naphthenate, cobalt naphthenate, zinc formate, zirconium formate, zinc acetate and zirconium acetate.
- hydrocarbon is one member selected from the class consisting of petroleum benzine, gasoline, benzene, toluene, xylene, trichloroethylene, perchloroethylene and ethyl acetate.
Abstract
The present invention relates to a process for imparting highelastic recovery to extensible knitted or woven fabrics by treating the fabric with an organic solution of low-viscosity containing a hydroxy-terminated dimethylpolysiloxane, a methylhydrogen polysiloxane and an organometallic catalyst.
Description
United States Patent Tsuruta et al.
[54] PROCESS FOR IMPARTING HIGH- ELASTIC RECOVERY TO EXTENSIBLE KNITTED OR WOVEN FABRICS AND PRODUCT OBTAINED [72] Inventors: Motohiro Tsuruta, Kyoto-shi; Hiroshiro Kimura; Akio Koshimo; Hirohlsa Nara, all of Kyoto-fu; Tokuju Goto, Nara-shi; Kunio Amemiya; Hideki Matusaka, both of Kyoto-fu, all of Japan [73] Assignee: Nippon Rayon Kabushiki Kaisha (Nippon Rayon Co., Ltd.), Kyoto-fu, Japan [22] Filed: Sept. 20, 1968 21 Appl. No.: 761,336
[30] Foreign Application Priority Data Jan. 13, 1968 Japan ..43/1829 Sept. 20, 1967 Japan ..42/60336 [52] U.S.Cl. ..ll7/l38.8 A, 117/7, 117/1388 E,
117/l38.8 F, l17/l38.8 N, 117/1388 PV,
117/1388 UA, l17/139.5 A, 117/161 ZA [51] Int. Cl. ..D06m 15/66 [58] Field ofSearch ..1 17/161 ZA, 138.8 A, 138.8 E, 117/1388 F, 138.8 N, 138.8 PV, 139.5 A; 252/86;
Primary ExaminerWilliam D. Martin Assistant Examiner-Ralph Husack AttorneyMeyer A. Gross [5 7] ABSTRACT The present invention relates to a process for imparting highelastic recovery to extensible knitted or woven fabrics by treating the fabric with an organic solution of low-viscosity containing a hydroxy-terminated dimethylpolysiloxane, a methylhydrogen polysiloxane and an organometallic catalyst.
9 Claims, No Drawings PROCESS FOR IMI'ARTING HIGH-ELASTIC RECOVERY TO EXTENSIBLE KNITTED OR WOVEN FABRICS AND PRODUCT OBTAINED BACKGROUND OF THE INVENTION Conventional processes are known for producing waterproof fabrics by treating fabrics having relatively low extensibility with organopolysiloxanes. For example, British Pat. No. 1,077,190 describes a process for producing waterproof fabrics by treating a fabric with a highly viscous solution of organopolysiloxanes having a viscosity of from 1,000 to 100,000 c.p.s. ln this process, because of the high viscosity of the solution, the interfiber voids on the surface are filled up with the solution, which accordingly can not penetrate sufficiently deeply into the interior of the fabric. In addition, for the purpose of producing waterproof fabrics, the fabric used should have a relatively low extensibility.
SUMMARY OF THE INVENTION It has now unexpectedly been discovered that the elastic recovery of knitted or woven fabric having a relatively large extensibility can be enhanced without the deminution of extensibility while the elastic recovery of the fabric remains substantially unchanged in both dry and wet states by treating such fabric with a low-viscous solution of organopolysiloxanes such as hydroxy-tcrminatcd dimethylpolysiloxane and methylhydrogen polysiloxane dissolved in a suitable organic solvent, said solution uniformly penetrating in an amount of from 1 to 5 percent (as solid) by weight of fabric into the fabric.
An object of the present invention is therefore to provide a process for imparting extensible knitted or woven fabrics with high-elastic recovery in both dry and wet states.
Further object of the prese' invention is to provide such improved fabrics.
According to the present invention, we provide a process for imparting extensible knitted or woven fabrics with highelastic recovery, which comprises treating the fabric with an organic solution having a viscosity of less than 400 c.p.s. and containing a hydroxy-terminated dimethylpolysiloxane, methylhydrogen polysiloxane and an organic metal catalyst so that said hydroxy-terminated dimethylpolysiloxane and methylhydrogen polysiloxane can be deposited in an amount of l to 5 percent (as solid) by weight of fabric in said fabric, and curing the same at a temperature of from 120 to 200 C.
The knitted or woven fabrics which may be used for the purpose of the present invention have preferably an extensibility of more than 20 percent and include e.g., those composed of textured yarns made of synthetic fibers such as fibers of polyamide, polyester, polyacrylonitrile, polyolefin, polyvinylalcohol etc. Preferred examples of textured yarns" include crimped yarns such as twist-set-untwist yarns, false twist yarn, stuffer box-treated yarn, edge-crimped yarn, air-jetted yarn and mixtures thereof.
The term extensibility" used in this specification denotes the percentage of elongation of a sample piece having a width of 5 cm. and a length of cm. when burdened with a load of 1.5 kg. based on the original length of the sample piece.
The treating solution used for the process of the present invention may have the following composition:
1. A hydroxy-terminated dimethylpolysiloxane having the following general formula:
. Lie J11 in which n is an integer from 15 to 50.
3. An organometallic catalyst, for example, zinc caprylate, tin caprylate, zirconium caprylate, dibutyl tin dilaurate, dibutyl tin dicaprylate, dibutyl tin diacetae, dibutyl tin oxide, alkyl titanate, zinc naphthenate, tin naphthenate, zirconium naphthenate, ferric naphthenate, cobalt naphthenate, zinc formate, zirconium formate, zinc acetate, zirconium acetate etc.
The foregoing components are dissolved in an organic solvent in which the organopolysiloxanes are soluble and which does not deteriorate the texture of the fabric and is inactive to said substances. Preferred examples of organic solvents which may be used for the purpose of the present invention include hydrocarbons having carbon atoms of not more than 10 such as petroleum benzine,- gasoline, benzene, toluene, xylene, trichloroethylene, perchloroethylene and ethylacetate.
Further, better results may be obtained by adding suitable additives such as e.g., sodium alcoholate, ester silane, polyalkyl silicate etc. These additives serve to improve the elastic recovery and washability of the final products because they are capable of cross-linking with aforesaid polysiloxanes so as to increase the degree of the polymerization.
Sodium alcoholates are represented by the general fonnula: RONa, in which R is an alkyl group having less than five carbon atoms. Polyalkyl silicate is a polymer obtained by partially hydrolyzing organosilicates represented by the general formula: (R0),Si, in which R is an alkyl group having less than five carbon atoms. Ester silanes are represented by the general formula:
R,,Si(OR' in which R is an alkyl group having less than five carbon atoms and R' is an alkyl group having less than five carbon atoms, and n is an integer of from 1 to 3.
The treating solution of the present invention must be applied to the fibers uniformly, and for this purpose, the dimethylpolysiloxane of the present invention should be dissolved in the organic solvent so as to give a low viscosity. It is essential that the viscosity of the treating solution at 20 C. used in the present invention is less than 400 c.p.s. (as measured by using a conventional rotary viscometer [type BL available from Tokyo Keiki Seizo-sho. K.K., Japan]). If the viscosity is higher than that level, the liquid is liable to remain only the surface of the fabric, thus covering the interfiber voids so that it hardly is possible to obtain the desired elastic recovery. The preferred blending proportions of the components are for example as follows:
Five to 30 (preferably 10 to 25) weight parts of methylhydrogen polysiloxane and 0.1 to 5 weight parts of organometal catalyst per weight parts of dimethyl polysiloxane. The organic solvent should be used in sufficient amounts so that the liquid viscosity will stay below 400 c.p.s.
There are various methods for applying the treating solution to the fabric, but it is advantageously effected e.g., either by immersing the fabric in the treating solution and then squeezing it, or by coating or spraying the solution to the fabric. The amount of deposition of the organopolysiloxanes should be 1.0 to 5.0 percent by weight of the fabric. If such amount is less than 1.0 percent, unsatisfactory elastic recovery may be obtained, while if it is more than 5.0 percent, the feel of and extensibility of the fabric may be deteriorated.
After treating the fabric, it is dried e.g., at 50 to C. under lowest possible tension to remove the organic solvent. The fabric is then cured e.g., at 120 to 200 C. under lowest possible tension thereby effecting the cross-linkage of the organopolysiloxanes with the fibers and the reaction between each of the organopolysiloxanes. It is desirable to treat the fabric under minimum tension. Such lowtension treatment will permit the extensibility prior to the treatment to be carried over to the resultant article.
The article thus obtained has a high-elastic recovery never seen in conventional bulky articles and its elasticity can be equal to that of elastomer fibers. It is thus possible to obtain articles having high-elastic recovery being equal to that of the elastomer fibers by subjecting extensible fabric to the treatment according to the present invention. Articles thus obtained are free from deterioration of color fastness and washability, and can minimize production costs.
The following nonlimitative examples illustrate the invention.
EXAMPLES 1n the examples, the samples were cured by means of a conventional short-loop baking machine (available from Hirano Kinzoku Kogyo K.K., Japan). The extensibility and elastic recovery were determined in the following manner: I. Extensibility:
The extensibility was determined by using a tensile tester, Autograph P-loo (available from Shimazu Seisakusho, KK, Japan) under the following conditions:
Weight of Load l,500 g. Length ofsamplc cm. Width of sample cm. Tensile speed cm./min. Chart speed cm./min:
2. Elastic recovery:
A similar tester and samples to those described above were used for determining the elastic recovery. The sample was loaded with a suitable load so as to stretch the sample to a length of 80 percent of the elongation, which was obtained when loaded with a load of 1,500 grams. The sample was left for 1 minute. The sample was reluxed and left for 3 minutes in reluxed state, (without tension). The elastic recovery rate is the percentage of the recovery of the elongation during the reluxed state and can be defined as follows:
Elastic recovery rate (c/b) l00 in which b is the length by which the sample was stretched and c is the length by which the sample was recovered (and a+bc is the length of the sample after being stretched and then retained in relaxed state for 3 minutes without tension, where a is the length of the prestretched sample).
3. The extensibility and elastic recovery in wet state were determined in a similar manner to that described above after the removal of the water content of the sample, which has been immersed in water for 10 minutes by using a filter paper.
EXAMPLE 1 Two-stage interlock fabric (jersey) and twill-knitted fabric knitted by using nylon bulky yarn (70 deniers/Z filaments) were respectively immersed in a solution having the following composition (viscosity: 40 c.p.s.) and were squeezed to give polysiloxanes (as solid) amounting to 0.5%, 1.0%, 3.0%, 5.0%, and 7.0% by weight ofthe fabric respectively:
Composition of the solution: part by weight Dimethyl polysiloxane 2.7 Mcthylhydrogcn polysiloxane 0.3 Phcnyllrielhoxysilune 0.03 Dibutyl tin tliluurute 0.03 'lrichlumclhylenc 96.94
The trichloroethylene was removed off by heating at 80 C. The fabric was then cured by using a short-loop baking machine at l 55 C. for 3 min. under lowest possible tension.
The jersey and twill thus obtained had the extensibility and elastic recovery values shown in tables 1 and 2, respectively.
Key to Tables A. Amount of polysiloxane deposited as solid (percent by weight of the fabric) B. Extensibility C. Elastic recovery (in dry state) D. Elastic recovery (in wet state) E. Antipilling property (determined as class) TABLE 1 (2-stage interlock jersey) A 0 0.5 [.0 3.0 5.0 7.0 11 0|. 242.0 227.1 209.0 104.1 01.9 C 78.0 93.5 93.8 94.0 94.0 94.0 D 74.1 75.2 91.2 91.7 94.0 94.0 E l l 4 5 5 5 TABLE 2 (Twill knitted fabric) A 0 0.5 1.0 3.0 5.0 7.0 B 52.3 177.0 147.6 117.7 106.8 70.3 C 76.1 93.5 93.7 9309 94.0 94.0 D 73.2 80.1 92.8 93.0 93.4 93.7 E l 1 3 4 4 5 It is apparent from the tables that when the deposited amount of polysiloxanes is less than 5 percent (by weight of the fabric) substantial increase of extensibility can be obtained. Amounts greater than 5 percent will decrease the extensibility sharply and the feeling of the treated fabrics will also largely deteriorate. The elastic recovery in dried state is likely to be almost independent on the changes of the deposited amounts of the polysiloxanes, while the elastic recovery in wet state significantly decreases when the deposited amount of polysiloxanes is less than 1 percent by weight of the fabric. The antipilling property shown in tables l and 2 was determined by means of the method according to Japanese Industrial Standard (JlS) L-l076-l967, which is similar to the so-called lCI method. The antipilling property will be advantageous when the deposited amount of the polysiloxanes is more than 1 percent by weight of the fabric.
From the observation described above, it appears that the deposition of the polysiloxanes in an amount of from l to 5 percent by weight of the fabric is most favorable.
EXAMPLE 2 A similar process to that described in example 1 was performed with the exception of using the polysiloxanes in such amount that they would be deposited in the fabric in an amount of 2 percent by weight of the fabric (calculated as solid).
The amount of trichloroethylene was changed stepwise so as to give the viscosities of the solution of IO, 40, I20, 250, 400, 500 and 1,000 c.p.s., respectively. The obtained results are shown in tables 3 and 4. The results obtained are likely to be substantially independent on the treating time.
Key to Tables A. Viscosity ofthe solution (c.p.s.)
B. Extensibility (percent) C. Elastic recovery percent (in a dry state) D. Elastic recovery percent (in wet state) TABLE 3 (2-stage interlock jersey) From the tables, it is apparent that when the viscosity of the polysiloxanes-containing solution is not more than 400 c.p.s. good extensibility and elastic recovery rates both in dry and wet states can be obtained; while these values are lowered by using the polysiloxanes solution having a viscosity of more than 400 c.pts.
A three-stage interlock fabric of nylon bulky yarn (70 deniers/Z filaments; jersey) was immersed in a treating solution having the following composition, and was then dried at The washing test was performed by using a Hitachi SC-AT Model 3 Washing Machine (commercial product available from Hitachi Seisaku-sho l(.l(., Japan) and washed in a solution of l g./l. of Emal (an anionic washing agent available 800 C. to remove off the trichloroethylena from Kao Sekken K.l(., Japan) at 40 C. for minutes. Excel- 7 V lent elastic recovery in wet state, good extensibility and improved elastic recovery after washing for 5 minutes was par- Composition of the Solution (part by weight) hchlarly observed- Dimethylpolysiloxane 2.8 10 EXAMPLE 5 M 111 111 11 1 '1 0.7 oiiaut liin iizt ic mm A slmilar process to that described 1n example 4 was per- Trichloroethylene 96.48 formed with the exception that an ester silane [C ll'l Si(OC l-l substituted for the metallic sodium ethyiate. No washing u I 5 test was made in this example. The fabric obtained also had The fabflc was cured at 160 for under 3 lowest improved extensibility and elastic recovery as shown in table possible tension by using the conventlonal short-loop baking 7, machine to yield a fabric having an improved extensibility, and elastic recovery as shown in table 5. Key to Table A. Extensibility (percent) B. Elastic recovery (percent) TABLE 5 2 5 TABLE 7 Extensi- Elastic Condition Sample bility Recovery C diti S l A 8 y Nontrealed -2 01 Dry Nontreated 48.2 70.2 Treated 92.6 91.2 Treated I293 92.3 Wet Nontreated 47.1 69.8 Wet Nontreated 47.1 69.8 Treated ll4.2 90.9 Treated I 30.1 91.7
EXAMPLE 6 EXAMPLE 4 A similar treatment to that described in example 4 was carried out with the exception of substituting diethoxy pen- A f' 'reatmeht that dhschbed m exhmple 3 was h tasilane for the metallic sodium ethylate. The properties of the fhnhed using the y m s the except'oh of employ mg 40 fabric thus obtained are shown in table 8. No washing test was the following treatlng solutions: made Key to Table Composmon of the salmon (part by we1ght) A. Extens1b1l1ty (percent Dimethylpolysilowne B. Elastic recovery (percent) Methylhydrogcn polysiloxane 0.3 Metallic sodium ethylate 0.02 Dibutyl tin diacetate 0.02 Trichloroelhylene 96.66 Viscosity ofthe solution cps. TABLE 8 50 Condition Sample A B Organopolysiloxanes (3.5 percent calculated as solid) was Dry Nonuemd 4 70,; thus deposited on the fabric. The fabric was then dried at 80 Trealed 913 C. to remove off the solvent, and was cured at 160 to give a :glfi :32: 32:9, fabric having improved extensibility and elastic recovery as shown in table 6. The curing was performed in an analogous manner to that described in example 3.
Key to Table What is claimed is: A Extensibility b f washing (percent) 1. A process for imparting high-elastic recovery to extensi- Extensibmty ft washing five times (percent) ble bulky knitted or woven fabrics composed of textured yarns Elastic recovery before washing (Percent) made of synthetic fibers having an extensibility of more than D. Elastic recovery after washing five times (percent) 20 phmehh h h comphses apply 3 to the fhhhc ah orgamc solut1onconta1n1r1g l. a hydroxy-terminated dimethylpolysiloxane having the general formula: TABLE 6 Condition Sample A a c 1) CH1 1 II 0--s1-- 0-H Dry Nuntreuted 48.2 50.0 70.2 68.! LJJHJ J Treated 130.2 120.7 94.3 95.0 a 7 Wet Nontreutcd 47.l 49.0 69.0 66.6
Treated 133.1 130.0 was 91.5
in which n is an integer not less than 500;
2. a methylhydrogen polysiloxane having the general formuin which n is an integer from 15 to 50, the ratio of methylhydrogen polysiloxane to dimethylpolysiloxane is to 30 parts by weight of methylhydrogen polysiloxane based upon 100 parts by weight of dimethylpolysiloxane; and
3. an organic metallic catalyst, dissolved in an organic solvent capable of dissolving said polysiloxanes and utilized in an amount to give a solution having a viscosity of not more than 400 c.p.s. so that L0 to 5.0 percent by weight of the fabric, of polysiloxanes are deposited as solid on said fabric, and then curing the polysiloxane treated fabric at an elevated temperature.
2. The process of claim 1 in which said fabric is composed of textured yarn selected from the class consisting of polyamide, polyester, polyacrylonitrile, polyolefin, polyvinylalcohoi and mixtures thereof.
3. The process of claim 2 in which said textured yarn is twist-set-untwist yarn, false twist yarn, stuffer box-treated yarn or mixtures thereof.
4. The process of claim I in which the treating solution further contains at least one member selected from the class consisting of sodium alcoholate, ester silane and polyalkyl silicate.
5. The process of claim I in which said organometallic catalyst is at least one member selected from the class consisting of zinc caprylate, tin caprylate, zirconium caprylate, dibutyl tin dicaprylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, alkyl titanate, zinc naphthenate, tin naphthenate, zirconium naphthenate, ferric naphthenate, cobalt naphthenate, zinc formate, zirconium formate, zinc acetate and zirconium acetate.
6. The process of claim 1 in which said organic solvent is a hydrocarbon having carbon atoms of from one to 10.
7. The process of claim 6 in which said hydrocarbon is one member selected from the class consisting of petroleum benzine, gasoline, benzene, toluene, xylene, trichloroethylene, perchloroethylene and ethyl acetate.
8. The process of claim 1 in which said fabric is cured at a temperature of from l20 to 200 C.
9. The product of the process of claim 1.
Claims (10)
- 2. The process of claim 1 in which said fabric is composed of textured yarn selected from the class consisting of polyamide, polyester, polyacrylonitrile, polyolefin, polyvinylalcohol and mixtures thereof.
- 2. a methylhydrogen polysiloxane having the general formula: in which n is an integer from 15 to 50, the ratio of methylhydrogen polysiloxane to dimethylpolysiloxane is 5 to 30 parts by weight of methylhydrogen polysiloxane based upon 100 parts by weight of dimethylpolysiloxane; and
- 3. an organic metallic catalyst, dissolved in an organic solvent capable of dissolving said polysiloxanes and utilized in an amount to give a solution having a viscosity of not more than 400 c.p.s. so that 1.0 to 5.0 percent by weight of the fabric, of polysiloxanes are deposited as solid on said fabric, and then curing the polysiloxane treated fabric at an elevated temperature.
- 3. The process of claim 2 in which said textured yarn is twist-set-untwist yarn, false twist yarn, stuffer box-treated yarn or mixtures thereof.
- 4. The process of claim 1 in which the treating solution further contains at least one member selected from the class consisting of sodium alcoholate, ester silane and polyalkyl silicate.
- 5. The process of claim 1 in which said organometallic catalyst is at least one member selected from the class consisting of zinc caprylate, tin caprylate, zirconium caprylate, dibutyl tin dicaprylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, alkyl titanate, zinc naphthenate, tin naphthenate, zirconium naphthenate, ferric naphthenate, cobalt naphthenate, zinc formate, zirconium formate, zinc acetate and zirconium acetate.
- 6. The process of claim 1 in which said organic solvent is a hydrocarbon having carbon atoms of from one to 10.
- 7. The process of claim 6 in which said hydrocarbon is one member selected from the class consisting of petroleum benzine, gasoline, benzene, toluene, xylene, trichloroethylene, perchloroethylene and ethyl acetate.
- 8. The process of claim 1 in which said fabric is cured at a temperature of from 120* to 200* C.
- 9. The product of the process of claim 1.
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US3873338A (en) * | 1973-02-28 | 1975-03-25 | Us Air Force | Thermal stabilization of polyamide fibers |
US4211815A (en) * | 1973-12-01 | 1980-07-08 | Ciba-Geigy Corporation | Waterproofing of textiles |
US4223065A (en) * | 1977-11-08 | 1980-09-16 | Unitika Ltd | Anti-graying fabrics of synthetic polyester fibers and process for producing same |
US4303712A (en) * | 1979-01-22 | 1981-12-01 | Woodroof E Aubrey | Fabric silicone elastomer composite |
US4304814A (en) * | 1975-05-15 | 1981-12-08 | Rhone-Poulenc Textile | Flameproof textile articles based on halogen-containing modacrylic polymers |
US4306990A (en) * | 1980-07-18 | 1981-12-22 | Edward Goodman | Cleaning and protective composition and method |
US4311760A (en) * | 1976-10-04 | 1982-01-19 | Dow Corning Corporation | Method for applying mercaptoalkyl-containing polydiorganosiloxanes to textile fibers |
US4350725A (en) * | 1979-10-26 | 1982-09-21 | Norddeutsche Faserwerke Gmbh | Fabric and garment of circular weft-knit or circular warp-knit material |
US4501682A (en) * | 1982-12-17 | 1985-02-26 | Edward Goodman | Cleaning and protective composition and method |
US5004628A (en) * | 1987-05-22 | 1991-04-02 | Fuji Photo Film Co., Ltd. | Coating method and apparatus |
US5439677A (en) * | 1989-07-24 | 1995-08-08 | The Dial Corp. | Compositions and methods for treating hair using a mixture of polysiloxanes |
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US3873338A (en) * | 1973-02-28 | 1975-03-25 | Us Air Force | Thermal stabilization of polyamide fibers |
US4211815A (en) * | 1973-12-01 | 1980-07-08 | Ciba-Geigy Corporation | Waterproofing of textiles |
US4304814A (en) * | 1975-05-15 | 1981-12-08 | Rhone-Poulenc Textile | Flameproof textile articles based on halogen-containing modacrylic polymers |
US4311760A (en) * | 1976-10-04 | 1982-01-19 | Dow Corning Corporation | Method for applying mercaptoalkyl-containing polydiorganosiloxanes to textile fibers |
US4223065A (en) * | 1977-11-08 | 1980-09-16 | Unitika Ltd | Anti-graying fabrics of synthetic polyester fibers and process for producing same |
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EP2982356A1 (en) | 2014-08-06 | 2016-02-10 | The Procter and Gamble Company | Stretchable cuff connector material |
WO2016022625A1 (en) | 2014-08-06 | 2016-02-11 | The Procter & Gamble Company | Stretchable cuff connector material |
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EP3072487A1 (en) | 2015-03-25 | 2016-09-28 | The Procter and Gamble Company | Absorbent article with improved containment |
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WO2016154388A1 (en) | 2015-03-25 | 2016-09-29 | The Procter & Gamble Company | Absorbent article with improved containment |
WO2016154415A1 (en) | 2015-03-25 | 2016-09-29 | The Procter & Gamble Company | Absorbent article with improved fit |
WO2016154400A1 (en) | 2015-03-25 | 2016-09-29 | The Procter & Gamble Company | Absorbent article with improved design |
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