US3664864A - Durably shaping keratinous fibrous materials - Google Patents
Durably shaping keratinous fibrous materials Download PDFInfo
- Publication number
- US3664864A US3664864A US845508A US3664864DA US3664864A US 3664864 A US3664864 A US 3664864A US 845508 A US845508 A US 845508A US 3664864D A US3664864D A US 3664864DA US 3664864 A US3664864 A US 3664864A
- Authority
- US
- United States
- Prior art keywords
- fibrous material
- hydrogen atom
- unsubstituted
- substituted hydrocarbon
- denotes
- 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.)
- Expired - Lifetime
Links
- 239000002657 fibrous material Substances 0.000 title claims abstract description 36
- 238000007493 shaping process Methods 0.000 title claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 23
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000006185 dispersion Substances 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- -1 betaine compound Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 10
- 150000003839 salts Chemical group 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 229960003237 betaine Drugs 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000005470 impregnation Methods 0.000 abstract description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 abstract 1
- 239000004744 fabric Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000006399 behavior Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010409 ironing Methods 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- 238000010026 decatizing Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/01—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof
- D06M11/05—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof with water, e.g. steam; with heavy water
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
- Y10T442/2385—Improves shrink resistance
-
- 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
- Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]
Definitions
- fibrous material containing or consisting of keratin can be durably shaped in the required manner by impregnating it with a mercaptocarboxylic acid and then oxidizing it, or treating it with steam, while shaping.
- This method has a number of disadvantages which complicate or limit its use. For example, it is difficult to produce consistent results; colored articles readily undergo color changes at the treated places, and intensely red discoloration occurs when iron ions are present; moreover, the treatment has to be carried out by garment manufactures rather than by weavers.
- Salts of monoethanolamine have also been proposed for durable shaping of keratinous fibrous material.
- the effects obtainable are not sufficiently durable to laundering.
- the method of the invention comprises impregnating fibrous material with an aqueous solution or dispersion of a compound-which in the betaine form has the general formula where R is an unsubstituted or substituted hydrocarbon radical, R and R are hydrogen atoms or lower alkyl radicals preferably having from one to five carbon atoms, and R and R are hydrogen atoms or unsubstituted or substituted hydrocarbon radicals preferably having from one to 20. carbon atoms, and heating the impregnated materials with steam at 100 to 150 C while shaping, if desired after drying, intermediate storage and/or making it into garments.
- the radicals R, R and R in Formula I may be for example alkyl, cycloalkyl, aryl or aralkyl radicals having from one to 20 carbon atoms which may bear substituents such as hydroxyl or alkoxyl groups.
- suitable radicals are methyl, ethyl, Z-hydroxyethyl, propyl, 2-hydroxypropyl, butyl, 2-ethylhexyl, octyl, dodecanyl, cyclohexyl, phenyl, tolyl, benzyl, methoxyethyl, ethoxyphenyl and 4-ethoxybutyl.
- radical R contains up to carbon atoms
- R and R are hydrogen or methyl and R and R are hydrogen or aliphatic radicals having up to two carbon atoms.
- the substances to be used for the purposes of the invention are shown in Formula I in the betaine form.
- the radicals R and/or R are not hydrocarbon radicals, the substances may also be present in the form of ordinary salts in which the nitrogen atom has lost its positive charge owing the elimination of a proton, and the negative charge of the resultant anion is compensated by a separate cation X
- the nature of the cation X has no appreciable effect on the suitability of the substances to be used according to the invention.
- an alkali metal, ammonium or substituted ammonium ion in particular one having the formula R-NH -R Whether the substances to be used according to the invention are present in the impregnating liquor in the betaine form or in the form of a salt 11 or II] depends on the pH of the liquor, also in generally the case with dipolar ions.
- the compounds of the general Formula I, II or II are used in the form of their aqueous solutions or dispersions, especially their aqueous solutions. They are applied to the fibrous material in the usual manner, for example by knife coating, sprying, dipping or preferably by padding. It has been found advantageous to apply the solutions or dispersions at such a rate that 0.01 to 0.2 mole, preferably 0.02 to 0.1 mole, of a compound of the general Formula I, II or III is applied per kilogram of material to be treated.
- wetting agents it is sometimes expedient to add wetting agents to the impregnating liquors in order to achieve rapid penetration and equal distribution of the ingredients.
- Non-ionic wetting agents are preferred.
- Wetting agents are dispensible if the material has already been wetted in an earlier treatment.
- the impregnating liquors may contain other ingredients conventionally used for treating keratinous fibers, for example water and oil repellents, such as silicones and compounds having perfluorinated carbon chains.
- the fibrous material can be immediately brought into the desired shape in the presence of steam, if desired after intermediate drying.
- the special advantages of the new process are however particularly apparent when shaping is carried out later, because after the said intermediate drying operation the impregnated material can be stored for very long periods without the sensitizing effect imparted by the impregnation being lost. Shaping can be carried out at any processing stage in the presence of steam, and the material will retain the shape imparted to it.
- the fibrous material can for example be calendered, embossed, goifered, and particularly pleated and creased.
- the effects obtained are highly durable, i.e., they are not lost in use or any cleaning operations.
- Fabrics containing or consisting of keratin fibers, or garments made of such material can therefore be given an easycare finish.
- the process of the invention furthermore results in a substantial improvement in the handle, and the presence in the fibrous material of unreacted compounds of the general Formula I, II or 111 makes the material easier to shape in garment fabrication.
- the new process can be applied with special advantage after a shrink-resist finishing operation, for example a treatment with oxidizing agents such as dichlorocyanuric acid or salts thereof.
- EXAMPLE 1 Made-up mens trousers of pure wool are sprayed with a percent aqueous solution of the compound of Formula VI at the places where they are to be creased, until the sprayed portions have increased 40 50 percent in weight. The trousers are then arranged in the press and treated for to seconds with steam at 100 to 120 C while pressing to give the desired creases. After the steam has been shut off, the trousers are left in the press for another 20 to seconds, suction being applied for 5 seconds to accelerate cooling.
- the trousers obtained exhibit extremely durable creases.
- EXAMPLE 2 Pure wool cloth (plain weave; 250 g/m is padded with a 5 aqueous solution of the substance of Formula VII and squeezed to a wet pickup of 50 percent. The material is then decatized by treating it for 5 minutes with saturated steam at 2 atm. gauge. Suction is applied for 3 to 5 seconds and the cloth dried on a stenter with 3 percent overfeed at 100 C. The cloth thus treated is distinguished by an improved hand, is smoother in appearance, and has improved crease behavior in the wet condition and a durable decatizing effect.
- EXAMPLE 3 Cloth of the type described in Example 2 is impregnated and dried as described in that example. It is then stored for 3 months and made into trousers. It is found that the trousers are easier to shape than trousers of the same material which has not been impregnated with the substance of Formula VII. The trousers are steamed in an ironing press in the way described in Example 1. They have sharp and very durable creases and improved crease behavior in the wet condition.
- EXAMPLE 4 Made-up men's trousers of pure wool are sprayed with a 5 percent aqueous solution of the compound of Formula [V at the places where they are to be creased, until the sprayed portions have increased 40 50 percent in Weight. The trousers are then arranged in the press and treated for 10 to 20 seconds with steam at to C while pressing to give the desired creases. After the steam has been shut off, the trousers are left in the press for another 20 to 30 seconds, suction being applied for 5 seconds to accelerate cooling.
- the trousers obtained exhibit extremely durable creases.
- EXAMPLE 5 Pure wool cloth (plain weave; 250 g/m) is padded with a 5 percent aqueous solution of the substance of formula V and squeezed to a wet pickup of 50 percent. The material is then decatized by treating it for 5 minutes with saturated steam at 2 atm. gauge. Suction is applied for 3 to 5 seconds and the cloth dried on a stenter with 3 percent overfeed at 100 C. The cloth thus treated is distinguished by an improved hand, is smoother in appearance, and has improved crease behavior in the wet condition and a durable decatizing effect.
- EXAMPLE 6 Cloth of the type described in Example 5 is impregnated and dried as described in that example. It is then stored for 3 months and made into trousers. It is found that the trousers are easier to shape and dress than trousers of the same material which has not been impregnated with the substance of F ormula V. The trousers are steamed in an ironing press in the way described in Example I. have sharp and very durable creases and improved crease behavior in the wet condition.
- EXAMPLE 7 Made-up men's trousers of pure wool are sprayed with a 5 percent aqueous solution of the compound of Formula Vlll at the places where they are to be creased, until the sprayed portions have increased 40 50 percent in weight. The trousers are then arranged in the press and treated for 10 to 20 seconds with steam at 100 to 120 C while pressing to give the desired creases. After the stem has been shut off, the trousers are left in the press for another 20 to 30 seconds, suction being applied for 5 seconds to accelerate cooling.
- the trousers obtained exhibit extremely durable creases.
- a method of durably shaping keratinous fibrous material which comprises impregnating said fibrous material with an aqueous solution or dispersion of a compound which in the betaine form has the general formula or salt thereof where R is an unsubstituted or substituted hydrocarbon radical, R and R denotes a hydrogen atom or an unsubstituted or substituted hydrocarbon radical, and heating the impregnated material with steam at 100 to C while shaping.
- betaine compound used is one where R is an unsubstituted or substituted hydrocarbon radical having up to 15 carbon atoms, and R and R each denotes a hydrogen atom or an alkyl radical having up to two carbon atoms.
- a method of durably shaping keratinous fibrous material which comprises impregnating said fibrous material with an aqueous solution or dispersion of a compound which in the salt form has the general formula or salt thereof, where R is an unsubstituted or substituted hydrocarbon radical with one to carbon atoms, R and R are hydrogen atoms or alkyl radicals having from one to 5 carbon atoms, R and R are hydrogen atoms or unsubstituted or substituted hydrocarbon radicals having from one to carbon atoms.
- Keratinous fibrous material as claimed in claim 4 wherein the betaine compound used is one where R and R each denotes a hydrogen atom or an alkyl radical having up to two carbon atoms.
- Keratinous fibrous material which has been impregnated with a betaine salt having the formula where R is an unsubstituted or substituted hydrocarbon radical, R and R each denotes a hydrogen atom or a lower alkyl radical, R denotes a hydrogen atom gr an unsubstituted or substituted hydrocarbon radical, and X is a cation.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19681769865 DE1769865A1 (de) | 1968-07-27 | 1968-07-27 | Verfahren zur dauernhaften Formgebung von Keratin enthaltendem oder aus Keratin bestehendem Fasergut |
Publications (1)
Publication Number | Publication Date |
---|---|
US3664864A true US3664864A (en) | 1972-05-23 |
Family
ID=5700308
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US845508A Expired - Lifetime US3664864A (en) | 1968-07-27 | 1969-07-28 | Durably shaping keratinous fibrous materials |
Country Status (7)
Country | Link |
---|---|
US (1) | US3664864A (en, 2012) |
BE (1) | BE736498A (en, 2012) |
CH (2) | CH1143169A4 (en, 2012) |
DE (1) | DE1769865A1 (en, 2012) |
FR (1) | FR2013857A7 (en, 2012) |
GB (1) | GB1266577A (en, 2012) |
NL (1) | NL6911320A (en, 2012) |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3055774A (en) * | 1960-09-01 | 1962-09-25 | Dow Corning | Method of rendering cellulose fabrics water-repellent and crease-resistant |
US3059990A (en) * | 1959-11-03 | 1962-10-23 | Nathan H Koenig | Method of setting wool textiles with ethanolamine |
US3198822A (en) * | 1961-10-13 | 1965-08-03 | Mannheimer | Quaternary ammonium sulfates and sulfonic acid salts |
US3225073A (en) * | 1960-11-08 | 1965-12-21 | Bayer Ag | Sulfuric acid semi-ester quaternary ammonium compounds |
US3239560A (en) * | 1962-03-05 | 1966-03-08 | Procter & Gamble | Method for preparation of halide hydroxysulfonate |
US3268564A (en) * | 1962-05-31 | 1966-08-23 | Nippon Oils & Fats Co Ltd | Quaternary ammonium perhalogenate salts |
US3268915A (en) * | 1963-04-08 | 1966-08-30 | Koratron Company Inc | Process of manufacturing press-free garment with retained creases |
US3280179A (en) * | 1961-03-16 | 1966-10-18 | Textilana Corp | Processes for producing acyclic surfactant sulfobetaines |
US3345195A (en) * | 1963-09-16 | 1967-10-03 | Dow Corning | Method for imparting a permanent crease to wool |
US3484185A (en) * | 1965-03-02 | 1969-12-16 | Iws Nominee Co Ltd | Method of presensitising fabric comprising kerationous fibers for subsequent setting |
US3491169A (en) * | 1966-07-22 | 1970-01-20 | Du Pont | Oil and water repellent |
US3516782A (en) * | 1967-06-30 | 1970-06-23 | Stevens & Co Inc J P | Permanent creasing of wool-containing fabrics |
-
1968
- 1968-07-27 DE DE19681769865 patent/DE1769865A1/de active Pending
-
1969
- 1969-07-18 FR FR6924585A patent/FR2013857A7/fr not_active Expired
- 1969-07-23 NL NL6911320A patent/NL6911320A/xx unknown
- 1969-07-24 BE BE736498D patent/BE736498A/xx unknown
- 1969-07-25 GB GB1266577D patent/GB1266577A/en not_active Expired
- 1969-07-25 CH CH1143169D patent/CH1143169A4/xx unknown
- 1969-07-25 CH CH1143169A patent/CH511320A/de unknown
- 1969-07-28 US US845508A patent/US3664864A/en not_active Expired - Lifetime
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3059990A (en) * | 1959-11-03 | 1962-10-23 | Nathan H Koenig | Method of setting wool textiles with ethanolamine |
US3055774A (en) * | 1960-09-01 | 1962-09-25 | Dow Corning | Method of rendering cellulose fabrics water-repellent and crease-resistant |
US3225073A (en) * | 1960-11-08 | 1965-12-21 | Bayer Ag | Sulfuric acid semi-ester quaternary ammonium compounds |
US3280179A (en) * | 1961-03-16 | 1966-10-18 | Textilana Corp | Processes for producing acyclic surfactant sulfobetaines |
US3198822A (en) * | 1961-10-13 | 1965-08-03 | Mannheimer | Quaternary ammonium sulfates and sulfonic acid salts |
US3239560A (en) * | 1962-03-05 | 1966-03-08 | Procter & Gamble | Method for preparation of halide hydroxysulfonate |
US3268564A (en) * | 1962-05-31 | 1966-08-23 | Nippon Oils & Fats Co Ltd | Quaternary ammonium perhalogenate salts |
US3268915A (en) * | 1963-04-08 | 1966-08-30 | Koratron Company Inc | Process of manufacturing press-free garment with retained creases |
US3345195A (en) * | 1963-09-16 | 1967-10-03 | Dow Corning | Method for imparting a permanent crease to wool |
US3484185A (en) * | 1965-03-02 | 1969-12-16 | Iws Nominee Co Ltd | Method of presensitising fabric comprising kerationous fibers for subsequent setting |
US3491169A (en) * | 1966-07-22 | 1970-01-20 | Du Pont | Oil and water repellent |
US3516782A (en) * | 1967-06-30 | 1970-06-23 | Stevens & Co Inc J P | Permanent creasing of wool-containing fabrics |
Also Published As
Publication number | Publication date |
---|---|
BE736498A (en, 2012) | 1970-01-26 |
CH511320A (de) | 1971-04-30 |
FR2013857A7 (en, 2012) | 1970-04-10 |
NL6911320A (en, 2012) | 1970-01-29 |
DE1769865A1 (de) | 1971-10-14 |
GB1266577A (en, 2012) | 1972-03-15 |
CH1143169A4 (en, 2012) | 1971-04-30 |
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