EP0107799A1 - Compositions résiniques à durée longue d'infroissabilité - Google Patents

Compositions résiniques à durée longue d'infroissabilité Download PDF

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Publication number
EP0107799A1
EP0107799A1 EP83109683A EP83109683A EP0107799A1 EP 0107799 A1 EP0107799 A1 EP 0107799A1 EP 83109683 A EP83109683 A EP 83109683A EP 83109683 A EP83109683 A EP 83109683A EP 0107799 A1 EP0107799 A1 EP 0107799A1
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Prior art keywords
weight
durable press
parts
composition
diluent
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EP83109683A
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German (de)
English (en)
Inventor
Eugene Ray Martin
David S. Ansel
Paul A. Manis
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Wacker Chemical Corp
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Wacker Chemical Corp
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Publication of EP0107799A1 publication Critical patent/EP0107799A1/fr
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins

Definitions

  • the present invention relates to compositions for treating textile materials and more particularly to durable press resin compositions for treating textile materials and to a process for treating textile materials to impart durable press finishes thereto.
  • Thermosetting durable press resins also known as aminoplast resins have been used to treat textile materials to impart durable press properties and dimensional stability characteristics to the treated textile materials.
  • These durable press resins such as methylolated ureas or methylolated urea based derivatives which are obtained from the reaction of formaldehyde and urea or urea based derivatives generally contain from 95.8 to 97.8 weight percent of aminoplast resin and from 4.17 to 2.2 weight percent of formaldehyde.
  • Textile materials finished with durable press resins generally release formaldehyde due to the hydrolysis of unreacted methylol groups.
  • the release of formaldehyde causes unpleasant odors and is a suspected health hazard. Therefore, it is preferred that textile materials finished with durable press resins be free of formaldehyde or at least have very low levels of formaldehyde.
  • Aminoplast resins have been developed which are free of formaldehyde and methylol groups; however, they do not impart satisfactory durable press properties to textile materials treated therewith.
  • textile materials treated with an aminoplast resin and an aldehyde provides a durable Dress resin finish at substantiallv lower add-on levels with desirable properties.
  • the resultant textile material releases low levels of formaldehyde, has satisfactory durable press properties and exhibits dimensional stability.
  • Another object of this invention is to provide durable press resin compositions for treating textile materials. Another object of this invention is to provide durable press finishes which impart softening and durable. press properties to textile materials. A further object of this invention is to provide a textile material having low formaldehyde levels, a soft hand, durable press properties and dimensional stability characteristics.
  • a- durable press resin cmposition containing (1) from 0.25 to 45 percent by weight of an aminoplast resin, (2) from 0.03 to 37 percent by weight of an aldehyde, and (3) from 18 to 99.72 percent by weight of a diluent based on the weight of the durable press resin composition.
  • the durable press resin composition is combined with an acid catalyst and applied to textile materials to impart durable press and dimensional stability properties thereto.
  • the treated textile materials have a low level of formaldehyde and a soft hand.
  • aminoplast resins which are used in the compositions of this invention are well known in the art. Suitable examples of aminoplast resins are the urea formaldehydes, e.g., propylene urea formaldehyde, and dimethylol urea formaldehyde; melamine formaldehyde, e.g., tetramethylol melamines, and pentamethylol melamines; ethylene ureas, e.g., dimethylol ethylene urea, dihydroxy dimethylol ethylene urea, ethylene urea formaldehyde, hydroxy ethylene urea formaldehyde; carbamates, e.g., alkyl carbamate formaldehydes; formaldehyde-acrolein condensation products; formaldehyde-acetone condensation products; alkylol amides, e.g., methylol formamide, methylol acetamide; acrylamides, e
  • aminoplast resins which may be used in the compositions of this invention may be represented by the formulas: wherein R 1 is hydrogen, a lower alkyl radical or a radical from a saturated or unsaturated aldehyde, R 2 is hydrogen, a lower alkyl radical or a radical represented by the formula R 3 is hydrogen or a methyl radical, R 4 is hydrogen or a lower alkyl radical, R 5 is hydrogen, a lower alkyl radical or C HR I O R 4 , with at least one R 5 being CHR 1 OR 4 , R 6 is a lower alkyl radical or hydroxy alkyl radical, R is hydrogen, hydroxy radical, or lower alkyl radical, R 8 is hydrogen, a lower alkyl radical, an alkylol radical, or an alkenol radical, X is oxygen or sulfur, and a is a number of from 1 to 6. Sulfur containing groups such as or sulfonium may be substituted for the group.
  • aldehydes which may be used in the compositions of this invention are saturated and unsaturated aliphatic aldehydes having from 1 to 20 carbon atoms, such as formaldehyde, ethanal, propanal, propenal, propynal; isomers of butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, tridecanal, tetradecanal, pentadecanal, hexadecanal, heptadecanal, octadecanal, nonadecanal, ecosanal, butenal, hexenal, undecenal, furfural and the like.
  • substituted saturated and unsaturated aldehydes having from 1 to 20 carbon atoms are haloalkanals, such as chloroethanal, dichloroethanal, bromal, chloral, 2-bromopropanal, 2-chloropropanal, 3-chloropropanal, 2-chloro-2-methylpropanal, 2,3-dibromopropanal, 2,3-dichloropropanal, 2,2,3-trichloropro- panal, 4-chlorobutanal, 2,3-dichlorobutanal, 2,2,3-trichloro- butanal and the like; hydroxyalkanals such as glycolaldehyde, 2,3-dihydroxypropanal, 3-hydroxybutanal, 4-hydroxypentanal, 3-hydroxy-2-methylpentanal and the like; alkylalkanals such as 2,2-dimethylpropanal, 2-ethylbutanal, 2-methylbutanal, 3-methylbutanal, 2-ethylhex
  • aromatic substituted or unsubstituted aldehydes examples include benzaldehyde, tolualdehydes, salicylaldehyde, 1-phenylpropynal, 2-benzylidenebutanal, 2-benzylidene- heptanal, hydroxybenzaldehydes, anisaldehyde, vanillin, piperanal, cinnamaldehyde, carboxybenzaldehydes and the like.
  • Diluents which are employed in the compositions of this invention are water and aliphatic alcohols having up to 8 carbon atoms.
  • a softening agent may be incorporated in the compositions of this invention to impart a soft hand to textile materials treated therewith.
  • the term softening agent includes any material which may be combined with the composition of this invention to impart a soft hand to treated textile materials.
  • Softening agents which may be added to the compositions of this invention are well known in the art.
  • suitable softeners are organopolysiloxanes which are capable of being crosslinked.
  • the crosslinkable organopolysiloxane compositions contain organopolysiloxanes having the general formula and a crosslinking agent such as a silane having the general formula or siloxanes having -Si-O-Si- linkages and the remaining valences of the silicon atoms are satisfied by R 10 and Y, in which R 10 , which may be the same or different, is as defined above, Y is an acyloxy, oximo, alkoxy, aryloxy, halogen, aminoxy, amido or phosphato group, d is a number of from 1 to 1000, and m is 0 or 1.
  • Catalysts such as those containing carboxylic acid salts of tin, zirconium, or titanium may be used with the organopolysi
  • softening agents which may be added to the compositions of this invention are non-crosslinkable polydiorganosiloxanes having the general formula in which R 10 and d are the same as above.
  • Organopolysiloxanes containing silicon-bonded hydrogen may be represented by the general formula in which R 10 is as defined above, e has a value of from 1.0 to 2.5, f has a value of from 0.005 to 2.0 and the sum of e + f is equal to from 1.005 to 3.0.
  • the organopolysiloxane containing silicon-bonded hydrogen may also be copolymers containing at least one unit per molecule of the formula with the remaining siloxane units of the organopolysiloxane having the average formula where R 10 and e are the same as above, e' has a value of from 0 to 2, f' has a value of from 1 to 2, and the sum of e' + f' is equal to from 1.0 to 3.0.
  • the copolymers contain from 0.5 to 99.5 mole percent of the siloxane units of the formula and from 0.5 to 99.5 mole percent of the siloxane units of the formula where R , e, e' and f' are the same as above.
  • the organopolysiloxanes containing silicon-bonded aliphatically unsaturated groups may be represented by the formula where R , e and f are the same as above and R 12 represents a silicon-bonded aliphatically unsaturated group such as a vinyl or allyl radical.
  • R 12 represents a silicon-bonded aliphatically unsaturated group such as a vinyl or allyl radical.
  • These organopolysiloxanes containing aliphatically unsaturated groups may also be copolymers having siloxane units of the formula where R 10 , R 12 , e', f' and the sum of e' + f' are the same as above.
  • the copolymers contain from 0.5 to 99.5 mole percent of units having the formula and from 0.5 to 99.5 mole percent of units having the formula where R , R , e, e' and f' are the same as above.
  • any catalyst capable of promoting the addition of silicon-bonded hydrogen to silicon-bonded aliphatically unsaturated groups may be used in preparing these softeners.
  • the catalyst is platinum or a. platinum compound or complex.
  • the silicone softeners may also contain organofunctional groups.
  • softeners which may be used are copolymers of ureidofunctional polydimethylsiloxanes having units of the formula and units of the formula where R 10 and R 13 are the same as above.
  • Softeners containing mercaptofunctional groups are polysiloxanes having units of the formula and units of the formula wherein R10, R 13 and e are the same as above and h is a number of from 1 to 3.
  • organofunctional silicone softeners which may be included in the compositions of this invention are the silylated polyethers described in U . S. Patents Nos. 4,312,993 and 4,331,797 to Martin which are incorporated herein by reference.
  • compositions containing silanol terminated polyorganosiloxanes and the silylated polyethers described in U. S. Patents Nos. 4,312,993 and 4,331,797 to Martin can be used as softeners in the compositions of this invention.
  • silicone softeners which may be included in the durable press compositions of this invention are those described in U. S. Patent No. 4,184,004 to Pines, which is incorporated herein by reference. These softeners consist of organosilicone terpolymers containing a plurality of reactive epoxy groups and a plurality of polyoxyalkylene groups. These organosilicone terpolymers may be prepared by the platinum catalyzed addition of an ethylenically unsaturated epoxy compound and an ethylenically unsaturated polyoxyalkylene organic radical free of olefinic unsaturation, preferably an alkyl compound, to hydrosiloxanes.
  • Organic softening agents may also be used in the durable press resin compositions of .this invention in the presence or absence of the above silicone softeners.
  • Suitable examples of organic softeners are fatty amides, fatty acid amines, and fatty acid amido amines; amido amines with mono- and diglycerides, quaternized ethoxylated fatty acid amines, hydroxyethyldiethyl- ammonium sulfate and stearic quaternary ammonium compounds; fatty acid esters such as stearates, glycerol stearates, diethylene glycol stearates, and sulfonated fatty acid esters of polyethylene glycols and diethylene glycols; oxyalkylene polymers such as oxyethylene polymers, oxypropylene polymers, and copolymers thereof, salts of long-chain alcohols and fatty alcohol/fatty acid amide blends; fatty acids such as lauric, myristic,
  • the softening agent When the softening agent is added to the durable press resin composition, i.e., an aminoplast resin, aldehyde and diluent, it is preferred that it be present in an amount such that the resultant finishing bath used for treating textile materials will contain up to about 8 parts by weight of softening agent.
  • the softening agent may be dissolved in aliphatic alcohols such as methanol, ethanol, butanol, hexanol and octanol.
  • the durable press resin compositions of this invention may be prepared by mixing the aminoplast resin, aldehyde and diluent in any order and at temperatures ranging from about 10°C to 90°C.
  • the durable press resin composition may be applied to any textile materials.
  • suitable textile materials are cotton, rayon, polyester, polypropylene, polyethylene, polyurethane, polyamide, wool, hemp, natural silk, cellulose acetate and polyacrylonitrile fibers as well as mixtures of these fibers.
  • the textile materials may consist of staple or monofilament fibers and fabrics made thereof.
  • the durable press resin compositions of this invention may be applied to the textile materials by any means known in the art, such as by spraying, immersion, foaming, padding, calendering or by gliding the fibers across a base which has been saturated with the compositions of this invention.
  • a preferred method for treating textile materials is to use a finishing bath containing a solution, dispersion or emulsion of the durable press resin compositions of this invention.
  • the finishing bath composition contains the durable press resin composition, acid catalyst and softener, if desired.
  • the finishing bath composition may be further diluted with a diluent. It is preferred that the diluent be the same diluent or at least a diluent which is compatible with the diluent used in the durable press resin composition.
  • the diluent is water or an aliphatic alcohol having from 1 to 8 carbon atoms.
  • the finishing bath preferably contains from 0.1 to about 99 parts by weight, and more preferably from about 5 to 50 parts by weight of durable press resin composition and from about 0.5 to 20 parts by weight, and more preferably from about 1 to 10 parts by weight of acid catalyst.
  • the amount of diluent added to the finishing bath may range from 0 to 99.4 parts by weight and more preferably from about 10 to 75 parts by weight and the amount of softening agent, when present, may range from about 0 to about 8 parts by weight and more preferably from about 1 to 5 parts by weight.
  • any of the known surfactants can be used as emulsifying agents, including the anionic, cationic, nonionic and amphoteric surfactants.
  • Suitable examples of acid catalysts which may be used in the compositions of this-invention are water soluble metal salts such as magnesium chloride, magnesium nitrate, magnesium sulfate, magnesium dihydrogenphosphate, zinc nitrate, zinc chloride, zinc tetrafluoroborate, aluminum chlorohydrate, aluminum chloride and mixtures of two of the above salts; water soluble ammonium and amine salts such as ammonium chloride, ammonium sulfate, aminomethylpropanol hydrochloride and aminomethylpropanol nitrate; ammonium and amine salts in combination with the metal salts described above; acids such as oxalic acid, gluconic acid, phosphoric acid, tartaric acid, maleic acid, p-toluenesulfonic acid and acetic. acid; and combinations of the above acids with the above described.metal salts.
  • water soluble metal salts such as magnesium chloride, magnesium nitrate, magnesium sulfate, magnesium
  • the aminoplast resin component and the water soluble acid catalyst component should be kept separate until ready for use due to the instability of the mixture.
  • the other components of this invention may be combined together in any order. It is, however, preferred that the other components be added to the aminoplast resin component.
  • the amount of the durable press resin composition of this invention which is applied to the textile material depends on the desired properties of the treated material. Generally, it is preferred that the textile material be treated with from 0.1 to 25 percent by weight of durable press resin composition, and more preferably from 0.2 to 20 percent by weight of the durable press resin composition, based on the weight of the textile material.
  • the textile material finished with the composition of this .invention is heated at an elevated temperature, e.g., from 80° to 200°C for a brief period of time; e.g., from 20 seconds to 15 minutes.
  • the-treated textile material can be dried below the above temperature range, e.g., from 50 to 95°C for a brief period of time, e.g., from 1 to 10 minutes, and then cured at an elevated temperature, e.g., from 125 to 200°C for an even briefer period of time, e.g., 15 to 60 seconds.
  • Textile materials treated with the durable press resin compositions of this invention exhibit all properties common to textile materials treated heretofore with aminoplast resins.
  • levels of aminoplast resin are reduced in conventional systems, in order to lower the formaldehyde levels on the fabric, poor durable press properties and dimensional stability characteristics are observed.
  • the addition of aldehydes permit a reduction of the aminoplast resin component of from 57 to 95 percent without adversely increasing the amount of formaldehyde present on the textile material after treatment, and without affecting the durable press properties and dimensional stability characteristics.
  • the addition of softener to the durable press resin compositions of this invention does not alter the durable press properties and dimensional stability characteristics of the fabric nor formaldehyde levels on the textile material.
  • Textile materials treated with the durable press resin/softener compositions of this invention have a softer hand than those treated with the durable press resin compositions alone or with other conventional aminoplast resins.
  • the durable press finish is significantly more economical.
  • compositions of this invention are agents which improve abrasion resistance of the treated fibers, materials which improve the fragrance of the treated textile materials, antistatic agents, lubricants, fire retardant agents, soil resistant materials, other hydrophilic, oleophilic, or hydrophobic agents and soil release materials such as those described in U. S. Patents Nos. 3,595,141 and 3,377,249 to Marco.
  • the compositions are padded onto samples of polyester/cotton (65/35) fabric at 50 percent wet pick-up.
  • the fabric is dried for 60 seconds at 120°C and cured for 20 seconds at 204°C.
  • the treated fabric is then evaluated for: (a) parts per million formaldehyde; (b) dimensional stability through five home launderings; (c) durable press properties through five home launderings.
  • compositions are prepared by dispersing the ingredients listed in Table II in water. These compositions are' padded onto polyester/cotton (65/35) fabric at 50 percent wet pick-up. The fabric is dried and cured in accordance with the procedure described in Example I. The treated fabric is then evaluated for (a) parts per million formaldehyde; (b) dimensional stability through five home launderings; and (c) durable press rating through five home launderin g s.
  • compositions are prepared by dispersing the ingredients listed in Table III in water. These compositions are padded onto polyester/cotton (65/35) fabric at 50 percent wet pick-up. The fabric is dried and cured in accordance with the procedure described in Example 1 . The treated fabric is then evaluated for (a) parts per million residual formaldehyde; (b) dimensional stability through five home launderings; and (c) durable press through five home launderings.
  • compositions are prepared by dispersing the ingredients listed in Table I V in a water-ethanol solvent. These formulations are padded onto polyester/cotton (65/35) fabric at a 30 percent wet pick-up. The fabric is dried and cured in accordance with the procedure described in Example 1. The treated fabric is then evaluated for (a) parts per million formaldehyde; (b) dimensional stability through five home launderings; and (c) durable press through five home laundering
  • compositions are prepared by dispersing the ingredients of Table V in water. These compositions are padded' onto 100 percent cotton at a 50 percent wet pick-up. The fabric is dried and cured in accordance with the procedure described in Example 1. The treated fabric is then evaluated for (a) parts per million formaldehyde; (b) dimensional stability through five home launderings; and (c) durable press through five home launderings.
  • compositions are prepared by dispersing the ingredients listed in Table VI in water. These compositions are padded onto polyester/cotton (65/35) .fabric at 50 percent wet pick-up. The fabric is dried and cured in accordance with the 5 procedure described in Example 1 . The treated fabric is then evaluated for (a) parts per million formaldehyde; (b) dimension stability through five home launderings; (c) durable press through five home launderings; and (d) fabric hand.
  • the softeners shown in Table VI are prepared in the following manner:
  • the resultant product is mixed with 238 parts by weight of aminopropyltriethoxysilane at 70°C for 3.0 hours.
  • This reaction product is a yellow liquid having a viscosity of about 30,000 cs. at 25°C.
  • the reaction product is mixed with 660 parts by weight of hydroxy terminated polydimethylsiloxane at 50°C for 6 hours.
  • the resultant product is a white, opaque fluid having a viscosity of 1,500,000 cs. at 25°C.
  • the product is then combined with 6,700 parts by weight of water. A white, opaque emulsion having a viscosity of 50 cs. at 25°C is obtaine
  • a 33 percent aqueous solution of a polymer is prepared by heating a mixture containing 150 parts of succinic anhydride and 2880 parts of oxyethylene-oxypropylene triol copolymer, having a molecular weight of 6360 and a weight ratio of oxyethylene to oxypropylene of 7 to 3, for eighteen hours at 120°C.
  • the product is a yellow liquid having a viscosity of 4,168 mPa.s at 25°C, and an acid content of 0.58 milliequivalents per gram (theoretical 0. 5 me q/g).
  • the resultant product is then mixed with 300 parts of aminopropyltriethoxysilane and heated at 70°C for 2 hours.
  • the product is a yellow liquid having a viscosity of about from 30,000 mPa.s at 25°C.
  • the resultant product is then mixed with 6670 parts of water to form a clear, straw-colored solution having a viscosity of 50 mPa.s at 25°C.
  • a 33 percent aqueous solution of a polymer is prepared by heating. a mixture containing 124 . parts of succinic anhydride, 930 parts of oxyethylene diol having a molecular weight of 1500 at 120°C for eighteen hours in a reaction vessel.
  • the resultant product is a yellow liquid having an acid content of 1.2 milliequivalents per gram.
  • the resultant product is mixed with 374 parts of aminopropyltriethoxysilane at 70°C for 3.0 hours.
  • the reaction product is mixed with 2702 parts of water. A clear straw-colored solution is obtained.
  • compositions are prepared by dispersing the ingredients shown in Table VII in water.
  • the softener is prepared in accordance with the procedure described in Example 6. These compositions are padded onto samples of polyester/cotton (65/35) fabric at a 50 percent wet pick-up.
  • the fabric is dried and cured in accordance with the procedure described in Example 1.
  • the treated fabric is then evaluated for (a) parts per million formaldehyde; (b) dimensional stability through five home launderings; (c) durable press through five home launderings; and (d) fabric hand.
  • compositions are prepared by dispersing the ingredients listed in Table VIII in water.
  • the softener is prepared in accordance with the procedure described in Example 6. These formulations are padded onto samples of polyester/cotton (65/35) fabric at 50 percent wet pick-up. The fabric is dried and cured in accordance with the procedure described in Example 1. The treated fabric is then evaluated for (a) parts per million formaldehyde; (b) dimensional stability through five home launderings; (c) durable press through five home launderings; and (d) fabric hand. The results of these evaluations show that the presence of an aldehyde in the formulation can enhance the durable press ratings and dimensional stability of the fabric through multiple home launderings while having formaldehyde levels which are acceptable by the textile industry. Furthermore, all fabrics treated with softeners have a soft, silky hand. The results are shown in Table VIII.
  • compositions are prepared by dispersing the ingredients listed in Table I X in water.
  • the softener is prepared in accordance with the procedure in Example 6. These formulations are padded onto polyester/cotton (65/35) fabric at 50 percent wet pick-up. The fabric is dried and cured according to the procedure in Example 1. The treated fabric is then evaluated for (a) parts per million formaldehyde; (b) dimensional stability through five home launderings; (c) durable press through five home launderings; and (d) fabric hand. The results of these evaluations show that the presence of formaldehyde in the formulation enhances the durable press ratings and dimensional stability of the fabric through multiple launderings while the fabric contains less than 250 parts per million of formaldehyde. In addition, all fabrics treated with softeners have a soft, silky hand. Furthermore, variation of the amount - of acid catalyst present in the formulation has no effect on either of the above results. The results are shown in Table IX.
  • compositions are prepared by dispersing the ingredients shown in Table X in water.
  • the softener is prepared in accordance with the procedure described in Example 6(a). These compositions are padded onto 100 percent cotton at 50 percent wet pick-up.
  • the fabric is dried and cured in accordance with the procedure described in Example 1.
  • the treated fabric is then evaluated for (a) parts per million formaldehyde; (b) dimensional stability through five home launderings; (c) durable press through five home launderings; and (d) fabric hand.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP83109683A 1982-09-30 1983-09-28 Compositions résiniques à durée longue d'infroissabilité Withdrawn EP0107799A1 (fr)

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US43018782A 1982-09-30 1982-09-30
US430187 1982-09-30

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JP (1) JPS5988979A (fr)
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CA (1) CA1216708A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0281919A3 (fr) * 1987-03-11 1991-03-13 BASF Aktiengesellschaft Liant pauvre en formaldéhyde

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB202000594D0 (en) * 2020-01-15 2020-02-26 Supercrease Ltd Resin for use in setting a crease in a garment

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1218696A (fr) * 1958-01-06 1960-05-11 Calico Printers Ass Ltd Procédé d'apprêtage des textiles
CH351938A (de) * 1957-09-16 1961-02-15 Raduner & Co Ag Verfahren zur Herstellung von hochnassfesten, mehrfarbig wie Papier bedruckbaren, aus Fasermaterialien hergestellten, versteiften Flächengebilden
DE2543978A1 (de) * 1971-06-04 1977-04-07 Pfersee Chem Fab Verfahren zum gleichzeitigen knitterfestmachen und hydrophobieren von cellulosehaltigen textilien
EP0052830A2 (fr) * 1980-11-24 1982-06-02 Bayer Ag Procédé de finissage de cordes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH351938A (de) * 1957-09-16 1961-02-15 Raduner & Co Ag Verfahren zur Herstellung von hochnassfesten, mehrfarbig wie Papier bedruckbaren, aus Fasermaterialien hergestellten, versteiften Flächengebilden
FR1218696A (fr) * 1958-01-06 1960-05-11 Calico Printers Ass Ltd Procédé d'apprêtage des textiles
DE2543978A1 (de) * 1971-06-04 1977-04-07 Pfersee Chem Fab Verfahren zum gleichzeitigen knitterfestmachen und hydrophobieren von cellulosehaltigen textilien
EP0052830A2 (fr) * 1980-11-24 1982-06-02 Bayer Ag Procédé de finissage de cordes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 85, no. 10, 6th September 1976, page 101, no. 64741e, Columbus, Ohio, US & JP-A-51 040 498 (TOYOBO CO., LTD.) 05-04-1976 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0281919A3 (fr) * 1987-03-11 1991-03-13 BASF Aktiengesellschaft Liant pauvre en formaldéhyde

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JPS5988979A (ja) 1984-05-23
CA1216708A (fr) 1987-01-20

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