US3782898A - Temporary soil release resins applied to fabrics in laundering - Google Patents
Temporary soil release resins applied to fabrics in laundering Download PDFInfo
- Publication number
- US3782898A US3782898A US00171362A US3782898DA US3782898A US 3782898 A US3782898 A US 3782898A US 00171362 A US00171362 A US 00171362A US 3782898D A US3782898D A US 3782898DA US 3782898 A US3782898 A US 3782898A
- Authority
- US
- United States
- Prior art keywords
- resin
- fabrics
- laundering
- solution
- souring
- 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
- 239000004744 fabric Substances 0.000 title abstract description 92
- 238000004900 laundering Methods 0.000 title abstract description 51
- 239000002689 soil Substances 0.000 title abstract description 50
- 239000011347 resin Substances 0.000 title description 112
- 229920005989 resin Polymers 0.000 title description 112
- 238000000034 method Methods 0.000 abstract description 39
- 238000011282 treatment Methods 0.000 abstract description 37
- 229920000178 Acrylic resin Polymers 0.000 abstract description 29
- 239000004925 Acrylic resin Substances 0.000 abstract description 29
- 239000000203 mixture Substances 0.000 abstract description 29
- 239000000675 fabric finishing Substances 0.000 abstract description 18
- 238000009962 finishing (textile) Methods 0.000 abstract description 18
- 238000005470 impregnation Methods 0.000 abstract description 16
- 238000004513 sizing Methods 0.000 abstract description 13
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 238000005282 brightening Methods 0.000 abstract description 3
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 90
- 239000003921 oil Substances 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 229920001577 copolymer Polymers 0.000 description 35
- 239000004753 textile Substances 0.000 description 34
- 238000012360 testing method Methods 0.000 description 27
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 21
- 229920000742 Cotton Polymers 0.000 description 20
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 19
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 13
- 239000003599 detergent Substances 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- 229920001519 homopolymer Polymers 0.000 description 13
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 13
- 229920000728 polyester Polymers 0.000 description 13
- 229920002125 Sokalan® Polymers 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000004584 polyacrylic acid Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000010705 motor oil Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 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 7
- 238000013019 agitation Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 238000010409 ironing Methods 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 238000010186 staining Methods 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004519 grease Substances 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000005108 dry cleaning Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 229940100445 wheat starch Drugs 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- RCDOBYOZJPNJCS-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propan-2-yl prop-2-enoate Chemical compound CC(=C)C(O)=O.CC(C)OC(=O)C=C RCDOBYOZJPNJCS-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- 241001556567 Acanthamoeba polyphaga mimivirus Species 0.000 description 1
- 241000212384 Bifora Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- KVBCYCWRDBDGBG-UHFFFAOYSA-N azane;dihydrofluoride Chemical compound [NH4+].F.[F-] KVBCYCWRDBDGBG-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- YWDYRRUFQXZJBG-UHFFFAOYSA-N butyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCCCOC(=O)C=C YWDYRRUFQXZJBG-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- HTEAGOMAXMOFFS-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C HTEAGOMAXMOFFS-UHFFFAOYSA-N 0.000 description 1
- MYSWGNHLJGOCPT-UHFFFAOYSA-N methyl prop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C=C MYSWGNHLJGOCPT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- -1 silk Polymers 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- BFXAWOHHDUIALU-UHFFFAOYSA-M sodium;hydron;difluoride Chemical compound F.[F-].[Na+] BFXAWOHHDUIALU-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
- C11D3/3765—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions in liquid compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
-
- 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
- D06M11/07—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 halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—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 halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
-
- 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
- D06M11/07—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 halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—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 halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
- D06M11/13—Ammonium halides or halides of elements of Groups 1 or 11 of the Periodic Table
-
- 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
- D06M11/77—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 silicon or compounds thereof
- D06M11/78—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 silicon or compounds thereof with silicon; with halides or oxyhalides of silicon; with fluorosilicates
-
- 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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
Definitions
- the laundering compositions comprise water, acrylic resin, and laundry sour or other fabric finishing agent.
- the acrylic resins are added to the last stage of the laundering cycle which is usually the sour operation. Moreover, the resins could be added to other fabric finishing treatments such as blueing, sizing, brightening or softening provided it is the last operation.
- the concentration of the resin in the sour or other finishing solution will be an amount so that the quantity of resin left on the fabric after drying will provide an effectual means for removing soil and stains. This is known asan effective amount of acrylic resin.
- the concentration of the resin in the treating composition will be at least one-quarter part resin per 5,000 parts by weight of souring solution or other treating solution such as blueing, or sizing,
- a preferred concentration range is one-half to 1 part of resin per 5,000 parts of sour, or other treating solution while concentrations as high as 3 parts of resin per 5,000 parts of treating solution have been used for reclamation of deeply soiled garments.
- the acrylic resin is generally an aqueous solution although some resins may be in the form of aqueous emulsions.
- the pH of the resin treating solution must be within the range of 4 to 6.5, preferably within a range of 4.5 to 6.0.
- the temperature during the impregnation treatment is not critical but is usually within the range of 70 to 180 F., preferably within the range of 95 to 180 F. These conditions of temperature and pH apply to either souring liquids or other fabric finishing treatment solutions in which the acrylic resin is suspended or is in solution.
- the resin treating solutions are separated from the fabrics by conventional laundry practice leaving the fabrics wet and impregnated with resin.
- the fabrics are then dried by conventional laundry practice leaving the resin on the fabrics. Drying temperatures of to 350 F. are satisfactory.
- the amount of resin left on the fabric after drying is in the order of 0.005 to 0.05 percent by weight.
- a preferred amount of resin is 0.01 to 0.2% by weight on a dry basis.
- the retained resin acts as a parting layer or film for subsequently acquired stains permitting their easy removal in subsequent laundering operations.
- the removal of the resin itself in subsequent laundering operations further increases the removal of soil and stains.
- the impregnated resin attacks deeply seated stains and greases already present so that repeated treatments with the resin eventually restore a badly soiled fabric to a usable condition.
- about three launderings including a resin treatment in each cycle are required to restore a fabric.
- the acrylic resins used in my process are mixtures of one or more homopolymers and copolymers obtained from acrylic acid or methacrylic acid, and alkyl esters of acrylic acid and methacrylic acid.
- the resin treating process is thoroughly compatible with present day laundering, and normal laundering conditions of temperature and detergent concentration for washing and rinsing precede the resin treatment of the fabrics.
- compositions for treating fabrics during laundering comprise the acrylic resins discussed above in aqueous mixtures with laundry sours and/or fabric finishing agents such as blues, brighteners, sizing agents and softeners.
- a laundry souring solution sufficient souring chemical must be present to give a pH within the range of 4 to 6.5 preferably within the range of 4.5 to 6.0.
- the same conditions of pH and acrylic resin concentration apply to other fabric finishing compositions comprising water, resin and fabric finishing agent such as blueing, sizing, brightener, or softener.
- the acrylic soil release resin may be applied by spray to a textile fabric which has previously been dried.
- the spray propellant may be air, carbon dioxide, hydrocarbons or fiuorocarbons.
- the fabrics are dried after spraying to remove the spray liquid.
- the clothes may be dried on racks or by tumbling in an air-clothes dryer or by ironing. Drying temperatures may vary from room temperature to 350 F.
- Example 8 is illustrative of this aspect of my invention.
- polyester and other synthetic fibers with or without premanent press or other resin finish are usually difiicult to clean in a conventional laundering operation. More particularly, polyester-cottons are especially susceptible to oily stains that become deeply set and are not easily removed. The polyester fibers are relatively hydrophobic and the conventional water laundering systems cannot penetrate the fabric to reach the stain and effect its removal.
- Drycleaning is being used to remove these deeply set grease stains from treated or untreated mixed fiber blends, but drycleaning suffers from the disadvantage that it is relatively much more expensive than laundering and drycleaning does not readily remove the water soluble portion of the soil which is usually present in large quantities.
- the resin treatment which I have discovered assists in the removal of previously acquired deeply imbedded stains. I have observed that after two or three resin treatments as hereinafter described, that deeply imbedded stains are effectively removed. Many fabrics which have been soiled so badly and which could not be cleaned by conventional laundering have been restored to normal service as a result of the application of successive treatments in accordance with my invention. Generally about three cycles of my process are required to restore a badly soiled garment. An unexpected benefit of my treatment is that the textile fabric so treated has a distinctly improved hand, size and texture, rendering them easier to finish and more aesthetically appealing.
- the essence of my invention is the discovery that acrylic resins of the types hereinafter disclosed may be applied to textile fabrics as a part of a final stage of a laundering operation whereby there is achieved a very low level of resin impregnation in the fabric.
- the impregnation of the acrylic resins on the textile fabrics is on the order of 0.005 to 0.05% by weight on a dry basis.
- a preferred amount is 0.01 to 0.2% by weight. It was an unexpected discovery to learn that this low level of resin impregnation would assist in the removal of deeply imbedded stains and give a textile fabric the ability to resist subsequently acquired stains.
- the resins suitable for practicing this invention are all derived from homopolymers and copolymers of acrylic acid and methacrylic acid.
- the homopolymers which form suitable soil release resins are polyacrylic acid and polymethacrylic acid. Either homopolymer or mixtures of the homopolymers provide satisfactory soil release resins for textile fabrics in my process.
- various copolymers formed by copolymerizing acrylic or methacrylic acid with alkyl esters of acrylic acid or methacrylic acid are satisfactory soil release resins.
- the mole ratio of acrylic acid or methacrylic acid to the alkyl esters of acrylic acid or methacrylic acid must be at least 1 to 1 in order to provide water solubility or water dispersibility of the copolymer. Any ratio of acid to ester greater than 1 to 1 including the acid homopolymers provide suitable soil release resins.
- the alkyl substituents are C through C groups. Mixtures of these copolymers are also satisfactory temporary soil release resins.
- Esters suitable for copolymerizing with acrylic acid or methacrylic acid to provide satisfactory temporary soil release resins are methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate and isobutyl methacrylate.
- mixtures of the homopolymers with the various copolymers described above are particularly useful as temporary soil release resins.
- Any ratio of mixtures of the homopolymers or mixtures of homopolymers and copolymers described above provides suitable temporary soil release resins for practicing my invention.
- a preferred temporary soil release system comprises mixtures of the homopolymer of acrylic acid and copolymer formed from ethyl acrylate and methacrylic acid.
- the resin homopolymers and copolymers are conveniently added to the laundry machine in the form of water solutions, emulsions or dispersions.
- polyacrylic acid is commercially available as 25 percent by weight aqueous solution.
- the acrylic resins are usually added directly to the souring solution in the laundry machine although the resin could be added to any reserve supply of souring solution.
- the souring solutions are acid solutions generally made from one of the fluosilicates such as sodium fluosilicate.
- the concentration of the resin in the souring solution is not critical. However, there must be present sufi icient resin in the souring solution so that when the garment is dried there will remain on the fabric sufiicient soil release resin to provide a means for removing soil and stains.
- Such a concentration of resin in the souring solution is known as an effective amount.
- the concentration of resin in the souring solution will be at 1 part of resin by weight per 5,000 parts of souring solution. Good results have been obtained at /2 part resin per 5,000 parts of souring solution, while some improvement in soil release properties has been obtained at A part of resin per 5,000 parts of souring solution.
- the concentration and pH of the resin in the separate treating solution must be the same as in the souring solution.
- the souring operation in a commercial laundry is generally the last operation in the laundry process.
- the application of the soil release resin is combined with the souring operation in order to avoid a separate laundry operation.
- the resin treatment is the last operation in the laundry process.
- the resin impregnaion must be the last operation to prevent loss of the resins by any subsequent laundering involving immersion in or rinsing of the fabrics with water which would wash away most of the resin.
- the sour operation removes the alkalinity in the fabrics which is not removed by the water rinses. Generally from two to five water rinses are employed prior to souring. The first water rinse is usually at the wash temperature of 180 to 190 F. Subsequent rinses are at progressively lower temperatures down to room temperature. Failure to remove nearly all of the alkali can cause skin irritation from the fabric.
- the sour solutions are prepared from acid salts and other acidic materials.
- the silicofiuorides are the most common sours.
- the silicofluorides are obtained in the form of ammonium, sodium, magnesium or zinc fluosilicates.
- Other materials used in laundry sours are sodium and ammonium acid fluoride, ammonium ch oride and acetic acid.
- Liquid sources of sours are hydrofluoric acid and fiuosilicic acid.
- the souring operation is generally done within a pH range of 4 to 6.5 and the amount of sour added will depend on the residual alkalinity from the washing cycle, the alkalinity of the water being used and the desired pH. Generally from 1 oz. to 12 ozs. of sour are used per 100 lbs. of dry textile fabrics. Generally from 350 to 500 pounds of water are used in each laundry operation for each 100 pounds of dry fabrics.
- the combined souring operation and application of the acrylic soil release resin to the fabrics is undertaken at a temperature within the range of 70 to 180 F.
- the temperature will be within the range of 95 F. and 180 F.
- One or more of the following fabric finishing chemicals may be combined with the souring and resin application to the fabrics: Blueing is generally applied to white goods at the rate of oz. per 100 pounds of white goods; Fabric brighteners are applied at the rate of 1 oz. per 100 pounds of dry fabrics; Fabric softeners are applied to the sour solutions at the rate of 1 /2 to 2 ozs. per 100 pounds of dry fabrics.
- Sizing is also compatible with the laundry souring solution and soil release resin.
- Sizing is generally wheat or corn starch and is used at a concentration of from 8 oz. to 1 lb. per 100 pounds of fabrics. Starch is applied to the souring at the same concentration.
- the above concentrations will provide an effective amount of fabric finishing agent. It will be appreciated that the concentration of fabric finishing agents in the souring solution are well known in the art. These concentrations will vary depend ing on local water conditions and the effect desired by the individual laundry operation.
- souring operation combined with resin impregnation and/or other fabric finishing treatment takes place within about 3 to minutes, preferably within 5 to 8 minutes.
- souring solution containing the acrylic resin the textile fabrics are separated from the treating solution and are then dried. Separation of the resin-sour solution is usually accomplished by centrifugal extraction or by hydraulic pressing.
- the wet resin impregnated fabrics are dried at temperatures varying from room temperature to about 350 F. Drying is accomplished in conventional air dryers for clothes or by ironing or by pressing. Ironing temperatures are generally about 350 F. Somewhat lower temperatures are generally used in the air dryers and satisfactory drying can be accomplished with air temperatures as low as about 70 F. or room temperature. The water is more rapidly removed at higher temperatures and temperatures of 150 to 350 F. are preferred.
- Example 1 In a Milnor Washer, Model #600CWM5 of 35 pounds dry clothes capacity was placed 24 pounds of cotton rags and 1 pound of 10" square test swatches of white shirting, 65/35 polyester cotton finished with a durable press resin.
- the washer was filled with water to the 16 gal. level and 0.25 pounds of a commercial all-inone laundry detergent was added. The water temperature was 150 F. After 10 minutes of agitation, the system was drained, refilled, and 0.125 pounds of detergent was added. It was agitated 5 minutes; at 150 F. and then drained. There were four 30 gal. water rinses, one each at 150 F., 130 F., F., and 90 F. After the four rinses, water was added to the 16 gal.
- test swatches were soiled by placing on them at two separate spots, 5 drops of refined mineral oil and 5 drops of used motor oil. These spots were then blotted and allowed to age for a minium of one half hour.
- the staining and rating procedure was the standard method of the American Association of Textile Chemists and Colorists, Test -l969.
- Control swatches made from fabric identical to the test swatches were laundered in exactly the same manner as the foregoing procedure with the exception that no polymer and copolymer mixture was added to the souring step.
- test series was carried out with resin addition in each souring step, and the control series was carried out with no resin addition at any time.
- the stains on the treated fabric were seen to be slightly lighter than the stains on the untreated fabric. That is, the laundering stage following resin treatment was more effective in removing the stains. After four complete cycles the stains applied at the end of the first cycle were nearly completely gone in the case of the test fabrics treated with resin and were still distinctly visible in the case of the untreated control fabric.
- Example 2 In a Milnor Washer, Model #600-CWM-5 of 35 pounds capacity was placed 24 pounds of cotton rags and 1 pound of square swatches of white shirting, 65/35 polyester cotton finished with a durable press resin. The washer was filled with water to the appropriate level and 0.25 pounds of a commercial all-in-one laundry detergent was added. The water temperature was 150 F. After 10 minutes of agitation, the system was drained, refilled, and 0.125 pounds of detergent was added. It was agitated 5 minutes at 150 F. and then drained. There were four high level rinses, one each at 150 F., 130 F., 110 F., and 90 F. The water was raised to the low level (16 gal.) at 120 F.
- Example 2 Three pints of the aqueous resin solution of Example 1 were added to the water. The resultant pH was 6.1. The system was agitated for 5 minutes, drained and centrifugely extracted for 1 minute. The cotton rags and test swatches were then air dried at 73 F. for 2 /2 hours.
- test swatches were soiled by placing on them at two separate spots, 5 drops of refined mineral oil and 5 drops of used motor oil. These spots were then blotted and allowed to age for a minimum of one half hour.
- Control swatches were prepared in exactly the same manner except that no resin mixture was added in the last step.
- the results after one wash, then application of soil release resin, then staining, then one additional wash showed control values of 3.5+ and 2.5 for mineral oil and motor oil respectively, and test value of 3.5+ and 3.0 for the respective stains on the resin treated fabric.
- Example 3 The test and control experiments of Example 1 were carried out varying the temperature of the solution in which the soil release polymer was applied to the textile. These experiments are recorded in Table II.
- Example 4 The test and control experiments of Example 1 were carried out, except that the damp test swatches, after centrifugal extraction, were tumbled in a hot air dryer at 150 F. Following are the results after 4 cycles of resin impregnation treatments with comparative controls.
- Example 5 In a Milnor Washer, Model #600-CWM-5 of 35 pounds capacity was placed 24 pounds of cotton rags and 1 pound of 10" square swatches of white shirting, /35 polyester cotton finished with a durable press resin. The washer was filled with water to the appropriate level and 0.25 pounds of a commercial all-in-one laundry detergent was added. The water temperature was 150 F. After 10 minutes of agitation, the system was drained, refilled, and 0.125 pound of detergent was added. It was agitated 5 minutes at 150 F. and then drained. There were four high level rinses, one each at 150 F., 130 F., 110 F., and 90 P. Then water was raised to the low level (16 gal.) at 120 F.
- the pH was adjusted to 4.1 by addition of ammonium fluosilicate sour and then 5 oz. of wheat starch were added to the souring solution. After one minute of agitation, there was added 1 pint of the resin solution described in Example 1. The system was agitated 8 more minutes, then centrifugely extracted for 1 minute. The textile fabrics were then tumble dried in a hot air drier at 200 F. air temperature.
- test swatches were soiled by placing on them at two separate spots, 5 drops of refined mineral oil and 5 drops of used motor oil. These spots were then blotted and allowed to age for a minimum of one-half hour.
- Control swatches were prepared in exactly the same manner as the foregoing procedure with the exception that no polymer and copolymer mixture was added to the souring step.
- test swatches were then subjected to three additional cycles of laundering, treatment with polymer and copolymer solution, drying, and staining, the subsequent stains being placed at different locations on the test swatches.
- the test series was carried out with polymer addition in each souring step, and the control [Grading at the completion of four cycles of spots applied at the end 01 1st cycle then subjected to three full cycles of treatment] Temperature of souring and application solution F. F. F. F. F. F. F. F. F.
- Example 1 0+ 5.0 weight increase was approximately 3% of the dry weight, equivalent to a polymer add-on of about 0.09% of the E l 6 10 dry textile.
- the textile swatch was subsequently dried by The experiment of Example 1 was carried out in which ggg i :2 3 2 t i fg g m g f $2 g varying amounts of sodium fluosilicate souring agent h an ere a were used to achieve various pH of the system in which si wflth a conventlonal home launqry the soil release polymers were applied to the textile.
- the eteggent i d A i removal .from the washuig results are tabulated in Table v.
- Example 1 oil oil oil oil oil oil oil oil oil 011 Oil 011 oil oil oil The procedure of Example 1 was carried out with a variety of textiles. These included 65/35 polyester cotton with crease resistant finish, rayon, pure cotton, silk, nylon,
- the swatches sprayed with polymer solution showed a motor oil stain rating of 3.5+ compared with 3.0+ for the control, and a mineral oil stain rating of 5.0 compared with 3.0+ for the control.
- Example 9 The procedure of Example 1 was carried out in which the ratio of the mixture of polymer solutions added to the souring solution was varied. The results of the experiments are reported in Table VI. Percentages are by weight.
- Example 8 An aqueous solution containing approximatel 3.9% by weight based on the solution of a 25% by weight aqueous It is observed that improved stain removal versus the control is obtained at all ratios.
- Example 10 The procedure of Example 1 was carried out except that the amount of soil release polymer added to the souring solution was varied. Results are reported in Table VII.
- Example 1 The experiment of Example 1 was carried out, except that cotton and 65/35 unfinished polyester/cotton were Example 14 used as fabrics, and a commercially available sizing con- The unacceptable heavily soiled garments left from the taimng starch was added at the rate of 4 ounces per 25 control part of Example 13 were laundered in exactly pounds of textlle to the souring solution together with the the same manner as in Example 13 except that 12 quarts polymer solution.
- Example 13 by weight aqueous solution of polyacrylic acid together Blue industrial work uniforms from an automotive repair shop, both shirts and pants, were loaded into a stainless steel washer 42" in diameter by 84" long. This washer was loaded with 200 pounds of permanent press finished 65/35 polyester content blend garments. Hot water was added to the washer to the level of 6 (170 gallons) at a temperature of 190 F. The garments were agitated by rotation of the washer for 6 minutes to remove loose grease and soil, and the water was removed from the washer.
- Example 15 The following copolymer compositions can be prepared by standard aqueous polymerization technique:
- copolymers are useful as temporary soil release resins in the practice of my invention.
- Example 16 The comparative test and control swatches are shown in Table IX.
- the improvement to impart temporary soil release to the textile fabrics comprising contacting the textile fabrics in the final stage of the laundering process prior to drying with a laundry souring solution having a pH within the range of about 4 to about 6.5 and containing from A at about 3 parts by weight of resin per 5,000 parts b weight of souring solution of one or more acrylic resins selected from the group consisting of polyacrylic acid, polymethacrylic acid and copolymers of acrylic acid and methacrylic acid with alkyl esters of acrylic acid and methacrylic acid, said alkyl substituents having one to four carbon atoms and said copolymers having a mole ratio of acid to ester of at least 1 to 1.
- souring solution contains an effective amount of one or more fabric finishing chemicals selected from the group consisting of blueing, sizing, brightener and softener in addition to the acrylic resin.
- the acrylic resin consists essentially of polyacrylic acid in admixture with a coplymer of methacrylic acid and ethylacrylate said copolymer having a mole ratio of methacrylic acid to ethylacrylate of at least 1 to 1.
- laundry souring solution is prepared by adding to water an effective amount of one or more compounds selected from the group consisting of ammonium fluosilicate, magnesium fiuosilicate, sodium fluosilicate, zinc fluosilicate, sodium bifluoride, ammonium bifiuoride, ammonium chloride, acetic acid, fluosilic acid and hydrofluoric acid.
- one or more compounds selected from the group consisting of ammonium fluosilicate, magnesium fiuosilicate, sodium fluosilicate, zinc fluosilicate, sodium bifluoride, ammonium bifiuoride, ammonium chloride, acetic acid, fluosilic acid and hydrofluoric acid.
- the improvement to impart temporary soil release to the textile fabrics comprising contacting the textile fabrics in the final stage of the laundering process prior to drying with an aqueous solution of one or more fabric finishing chemicals selected from the group consisting of blueing, sizing, brightener and softener at a pH within the range of about 4 to about 6.5 and containing from A to about 3 parts by weight of resin per 5,000 parts by weight of solution of fabric finishing chemical of one or more acrylic resins selected from the group consisting of poly: acrylic acid, polymethacrylic acid and copolymers of acrylic acid and methacrylic acid with alkyl esters of acrylic acid and methacrylic acid said alkyl substituents having one to four carbon atoms and said
- the improvement to impart temporary soil release to the textile fabrics comprising contacting the rinsed textile fabrics immediately prior to drying with an aqueous solution containing from A to about 3 parts by weight of resin per 5,000 parts by weight of solution of an acrylic resin selected from the group consisting of polyacrylic acid, polymethacrylic acid and copolymers of acrylic acid and methacrylic acid with alkyl esters of acrylic acid and methacrylic acid said alkyl substituents hav-.
- copolymers having a mole ratio of acid to ester of at least 1 to 1 and at a pH of about 4.0 to about 6.5.
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17136271A | 1971-08-12 | 1971-08-12 | |
US405996A US3909476A (en) | 1971-08-12 | 1973-10-12 | Temporary soil release resins applied to fabrics in laundering |
US407115A US3900606A (en) | 1971-08-12 | 1973-10-17 | Temporary soil release resins applied to fabrics by spraying |
Publications (1)
Publication Number | Publication Date |
---|---|
US3782898A true US3782898A (en) | 1974-01-01 |
Family
ID=27389966
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00171362A Expired - Lifetime US3782898A (en) | 1971-08-12 | 1971-08-12 | Temporary soil release resins applied to fabrics in laundering |
US405996A Expired - Lifetime US3909476A (en) | 1971-08-12 | 1973-10-12 | Temporary soil release resins applied to fabrics in laundering |
US407115A Expired - Lifetime US3900606A (en) | 1971-08-12 | 1973-10-17 | Temporary soil release resins applied to fabrics by spraying |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US405996A Expired - Lifetime US3909476A (en) | 1971-08-12 | 1973-10-12 | Temporary soil release resins applied to fabrics in laundering |
US407115A Expired - Lifetime US3900606A (en) | 1971-08-12 | 1973-10-17 | Temporary soil release resins applied to fabrics by spraying |
Country Status (11)
Cited By (26)
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US3909476A (en) * | 1971-08-12 | 1975-09-30 | Pennwalt Corp | Temporary soil release resins applied to fabrics in laundering |
US3912681A (en) * | 1972-05-01 | 1975-10-14 | Colgate Palmolive Co | Composition for imparting non-permanent soil-release characteristics comprising an aqueous acidic solution of polycarboxylate polymer |
US3920389A (en) * | 1973-01-31 | 1975-11-18 | Du Pont | Textile cleaning process |
US3948838A (en) * | 1968-07-25 | 1976-04-06 | Burlington Industries, Inc. | Soil release composition |
US3993830A (en) * | 1972-04-28 | 1976-11-23 | Colgate-Palmolive Company | Soil-release finish |
US4007305A (en) * | 1974-12-23 | 1977-02-08 | Basf Wyandotte Corporation | Method of imparting nondurable soil release and soil repellency properties to textile materials |
US4057503A (en) * | 1975-10-20 | 1977-11-08 | Pennwalt Corporation | Concentrates for imparting temporary soil release resins in fabrics during laundering |
US4108780A (en) * | 1977-07-19 | 1978-08-22 | Pennwalt Corporation | Dustless soil release-souring compositions for use in laundering |
US4170557A (en) * | 1978-04-11 | 1979-10-09 | Milliken Research Corporation | Process and composition for imparting anti-soil redeposition and soil release properties to polyester textile materials |
US4214997A (en) * | 1977-10-26 | 1980-07-29 | Lever Brothers Company | Soil-release compositions |
US4770666A (en) * | 1986-12-12 | 1988-09-13 | The Procter & Gamble Company | Laundry composition containing peroxyacid bleach and soil release agent |
US4925588A (en) * | 1986-12-24 | 1990-05-15 | Rhone-Poulenc Chimie | Antisoiling and anti-redeposition latices for the aqueous washing of textile articles |
US5004557A (en) * | 1985-08-16 | 1991-04-02 | The B. F. Goodrich Company | Aqueous laundry detergent compositions containing acrylic acid polymers |
US5076957A (en) * | 1987-05-06 | 1991-12-31 | Degussa Aktiengesellschaft | Phosphate-free detergent builders |
US5143729A (en) * | 1986-07-29 | 1992-09-01 | Fadeguard, Inc. | Fade resistant water and soil repellent composition for fabric |
US5409629A (en) * | 1991-07-19 | 1995-04-25 | Rohm And Haas Company | Use of acrylic acid/ethyl acrylate copolymers for enhanced clay soil removal in liquid laundry detergents |
WO1997035061A1 (en) * | 1996-03-18 | 1997-09-25 | R.R. Street & Co. Inc. | Method for removing contaminants from textiles |
US20040171515A1 (en) * | 2001-06-15 | 2004-09-02 | Christoph Hamers | Treatment method, which promotes the removal of dirt, for the surfaces of textiles and non-textiles |
US20040250354A1 (en) * | 2001-06-15 | 2004-12-16 | Christoph Hamers | Method for treating surfaces of textiles and non-textiles, in such a way as to stimulate the detachment of dirt |
WO2006079427A1 (de) * | 2005-01-26 | 2006-08-03 | BSH Bosch und Siemens Hausgeräte GmbH | Verfahren zum reinigen und imprägnieren von textilien |
US9279097B1 (en) | 2014-08-14 | 2016-03-08 | Ecolab USA, Inc. | Polymers for industrial laundry detergents |
US10533147B2 (en) | 2014-05-09 | 2020-01-14 | Ecolab Usa Inc. | Soil release polymer in a solid sour |
US10822578B2 (en) | 2018-06-01 | 2020-11-03 | Amtex Innovations Llc | Methods of washing stitchbonded nonwoven towels using a soil release polymer |
CN113736329A (zh) * | 2021-09-23 | 2021-12-03 | 海宁德易遮阳科技有限公司 | 一种感温变色涂料的制备及窗帘多层涂层的制备方法 |
US11220086B2 (en) | 2018-04-13 | 2022-01-11 | Amtex Innovations Llc | Stitchbonded, washable nonwoven towels and method for making |
US11884899B2 (en) | 2018-06-01 | 2024-01-30 | Amtex Innovations Llc | Methods of laundering stitchbonded nonwoven towels using a soil release polymer |
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US4043965A (en) * | 1972-05-01 | 1977-08-23 | Colgate-Palmolive Company | Copolymer of acrylic acid and 1,1-dihydroperfluorooctyl methacrylate useful for applying non-permanent soil release finish |
GB1517276A (en) * | 1974-08-21 | 1978-07-12 | Ici Ltd | Preparation of polymer film |
US4178256A (en) * | 1975-01-30 | 1979-12-11 | Basf Wyandotte Corporation | Compositions for souring and softening laundered textile materials, method of preparing the same, and stock solutions prepared therefrom |
GB1540722A (en) * | 1975-04-15 | 1979-02-14 | Unilever Ltd | Fabric treatment compositions |
FR2405905A1 (fr) * | 1977-10-11 | 1979-05-11 | Saint Gobain | Vitrage pare-feu a gel aqueux |
US4337186A (en) | 1978-01-17 | 1982-06-29 | National Research Development Corporation | Hardenable compositions |
GR67665B (enrdf_load_stackoverflow) | 1979-05-21 | 1981-09-02 | Unilever Nv | |
DE3206883A1 (de) * | 1982-02-26 | 1983-09-15 | Basf Ag, 6700 Ludwigshafen | Verwendung von copolymerisaten, die basische gruppen enthalten, als vergrauungsinhibitoren beim waschen und nachbehandeln von synthesefasern enthaltendem textilgut |
US4569772A (en) * | 1984-09-04 | 1986-02-11 | Colgate-Palmolive | Stabilization of polyethylene terephthalate-polyoxyethylene terephthalate soil release promoting polymers |
US4571303A (en) * | 1985-01-23 | 1986-02-18 | Colgate-Palmolive Company | Built nonionic detergent composition containing stabilized polyethylene terephthalate-polyoxyethylene terephthalate soil release promoting polymer |
FR2609065B1 (fr) * | 1986-12-24 | 1989-04-14 | Rhone Poulenc Chimie | Nouveaux agents de lavage et compositions les contenant |
AU627711B2 (en) * | 1988-03-11 | 1992-09-03 | Minnesota Mining And Manufacturing Company | Process for providing polyamide materials with stain resistance |
US4822373A (en) * | 1988-03-11 | 1989-04-18 | Minnesota Mining And Manufacturing Company | Process for providing polyamide materials with stain resistance with sulfonated novolak resin and polymethacrylic acd |
US5032102A (en) * | 1990-03-14 | 1991-07-16 | Mattel, Inc. | Toy figure having water dissolvable clothes and facial elements |
CA2047928A1 (en) * | 1990-07-27 | 1992-01-28 | Munehiro Nogi | Method and apparatus for washing dishes, sticking inhibitor and rinsing assistant |
US6190419B1 (en) * | 1997-07-07 | 2001-02-20 | Ales M. Kapral | Method of washing garments utilizing fluoric acid |
US5968664A (en) * | 1997-11-11 | 1999-10-19 | Mitsubishi Polyester Film, Llc | Polymeric coated substrates for producing optically variable products |
DE69832531T2 (de) * | 1998-04-27 | 2006-08-10 | The Procter & Gamble Company, Cincinnati | Kleidungskonditionierungszusammensetzung |
US6384005B1 (en) * | 1998-04-27 | 2002-05-07 | Procter & Gamble Company | Garment conditioning composition |
DE112009002580T5 (de) * | 2008-10-29 | 2012-06-21 | Mitsubishi Gas Chemical Co., Inc. | Textur entwickelnde Flüssigkeit für hauptsächlich aus Zinkoxid zusammengesetzten transparenten leitfähigen Film und Verfahren zur Herstellung von transparentem leitfähigem Film mit Aussparungen und Vorsprüngen |
UA108951C2 (uk) | 2011-08-31 | 2015-06-25 | Акцо Нобель Кемікалз Інтернешнл Б.В. | Пральні мийні композиції, які містять брудовідштовхувальну речовину |
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US2805205A (en) * | 1957-09-03 | Detergent compositions for laundering | ||
US2241580A (en) * | 1937-06-25 | 1941-05-13 | Pennsylvania Salt Mfg Co | Art of laundering and cleaning |
US2692182A (en) * | 1951-04-14 | 1954-10-19 | Rohm & Haas | Durable, stiff finish for nylon and method for producing same |
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US3236685A (en) * | 1962-06-20 | 1966-02-22 | Eastman Kodak Co | Process for treating textile fibers and other shaped products with coatings |
US3284364A (en) * | 1963-01-25 | 1966-11-08 | American Cyanamid Co | Soil anti-redeposition agents |
US3448462A (en) * | 1964-09-14 | 1969-06-10 | Deering Milliken Res Corp | Collar and cuff-like garment member and method of making it |
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US3575899A (en) * | 1969-07-28 | 1971-04-20 | Minnesota Mining & Mfg | Launderably removeable,soil and stain resistant fabric treatment |
GB1259888A (en) * | 1969-08-19 | 1972-01-12 | Allied Colloids Mfg Company Ltd | Improvements in and relating to textile size |
US3706672A (en) * | 1970-12-08 | 1972-12-19 | Celanese Corp | Detergent polyelectrolyte builders |
US3782898A (en) * | 1971-08-12 | 1974-01-01 | Pennwalt Corp | Temporary soil release resins applied to fabrics in laundering |
-
1971
- 1971-08-12 US US00171362A patent/US3782898A/en not_active Expired - Lifetime
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1972
- 1972-07-07 AU AU44346/72A patent/AU472029B2/en not_active Expired
- 1972-07-18 CA CA147,390A patent/CA990461A/en not_active Expired
- 1972-08-02 GB GB3604872A patent/GB1407012A/en not_active Expired
- 1972-08-02 GB GB5471274A patent/GB1407013A/en not_active Expired
- 1972-08-10 CH CH1186272A patent/CH579172A5/xx not_active IP Right Cessation
- 1972-08-11 FR FR7229022A patent/FR2148617B1/fr not_active Expired
- 1972-08-11 DE DE2239710A patent/DE2239710C2/de not_active Expired
- 1972-08-11 SE SE7210488A patent/SE410320B/sv unknown
- 1972-08-11 BE BE787453A patent/BE787453A/xx not_active IP Right Cessation
- 1972-08-11 NL NLAANVRAGE7211043,A patent/NL169897C/xx not_active IP Right Cessation
- 1972-08-14 AT AT701472A patent/AT332349B/de not_active IP Right Cessation
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1973
- 1973-10-12 US US405996A patent/US3909476A/en not_active Expired - Lifetime
- 1973-10-17 US US407115A patent/US3900606A/en not_active Expired - Lifetime
-
1975
- 1975-08-13 SE SE7509088A patent/SE413198B/xx not_active IP Right Cessation
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3948838A (en) * | 1968-07-25 | 1976-04-06 | Burlington Industries, Inc. | Soil release composition |
US3909476A (en) * | 1971-08-12 | 1975-09-30 | Pennwalt Corp | Temporary soil release resins applied to fabrics in laundering |
US3993830A (en) * | 1972-04-28 | 1976-11-23 | Colgate-Palmolive Company | Soil-release finish |
US3912681A (en) * | 1972-05-01 | 1975-10-14 | Colgate Palmolive Co | Composition for imparting non-permanent soil-release characteristics comprising an aqueous acidic solution of polycarboxylate polymer |
US3920389A (en) * | 1973-01-31 | 1975-11-18 | Du Pont | Textile cleaning process |
US4007305A (en) * | 1974-12-23 | 1977-02-08 | Basf Wyandotte Corporation | Method of imparting nondurable soil release and soil repellency properties to textile materials |
US4057503A (en) * | 1975-10-20 | 1977-11-08 | Pennwalt Corporation | Concentrates for imparting temporary soil release resins in fabrics during laundering |
US4108780A (en) * | 1977-07-19 | 1978-08-22 | Pennwalt Corporation | Dustless soil release-souring compositions for use in laundering |
US4214997A (en) * | 1977-10-26 | 1980-07-29 | Lever Brothers Company | Soil-release compositions |
US4170557A (en) * | 1978-04-11 | 1979-10-09 | Milliken Research Corporation | Process and composition for imparting anti-soil redeposition and soil release properties to polyester textile materials |
US5004557A (en) * | 1985-08-16 | 1991-04-02 | The B. F. Goodrich Company | Aqueous laundry detergent compositions containing acrylic acid polymers |
US5143729A (en) * | 1986-07-29 | 1992-09-01 | Fadeguard, Inc. | Fade resistant water and soil repellent composition for fabric |
US4770666A (en) * | 1986-12-12 | 1988-09-13 | The Procter & Gamble Company | Laundry composition containing peroxyacid bleach and soil release agent |
US4925588A (en) * | 1986-12-24 | 1990-05-15 | Rhone-Poulenc Chimie | Antisoiling and anti-redeposition latices for the aqueous washing of textile articles |
US5076957A (en) * | 1987-05-06 | 1991-12-31 | Degussa Aktiengesellschaft | Phosphate-free detergent builders |
US5409629A (en) * | 1991-07-19 | 1995-04-25 | Rohm And Haas Company | Use of acrylic acid/ethyl acrylate copolymers for enhanced clay soil removal in liquid laundry detergents |
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Also Published As
Publication number | Publication date |
---|---|
CH579172A5 (enrdf_load_stackoverflow) | 1976-08-31 |
AU4434672A (en) | 1974-01-10 |
CA990461A (en) | 1976-06-08 |
BE787453A (fr) | 1972-12-01 |
NL7211043A (enrdf_load_stackoverflow) | 1973-02-14 |
GB1407012A (en) | 1975-09-24 |
SE413198B (sv) | 1980-04-28 |
FR2148617B1 (enrdf_load_stackoverflow) | 1976-08-13 |
GB1407013A (en) | 1975-09-24 |
US3900606A (en) | 1975-08-19 |
FR2148617A1 (enrdf_load_stackoverflow) | 1973-03-23 |
AT332349B (de) | 1976-09-27 |
US3909476A (en) | 1975-09-30 |
DE2239710A1 (de) | 1973-02-15 |
SE410320B (sv) | 1979-10-08 |
NL169897C (nl) | 1982-09-01 |
ATA701472A (de) | 1976-01-15 |
SE7509088L (sv) | 1975-08-13 |
DE2239710C2 (de) | 1983-04-28 |
AU472029B2 (en) | 1976-05-13 |
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AS | Assignment |
Owner name: ATOCHEM NORTH AMERICA, INC., A PA CORP. Free format text: MERGER AND CHANGE OF NAME EFFECTIVE ON DECEMBER 31, 1989, IN PENNSYLVANIA;ASSIGNORS:ATOCHEM INC., ADE CORP. (MERGED INTO);M&T CHEMICALS INC., A DE CORP. (MERGED INTO);PENNWALT CORPORATION, A PA CORP. (CHANGED TO);REEL/FRAME:005496/0003 Effective date: 19891231 |