US3658575A - Method and compositions for treating flexible substrates - Google Patents
Method and compositions for treating flexible substrates Download PDFInfo
- Publication number
- US3658575A US3658575A US862031A US3658575DA US3658575A US 3658575 A US3658575 A US 3658575A US 862031 A US862031 A US 862031A US 3658575D A US3658575D A US 3658575DA US 3658575 A US3658575 A US 3658575A
- Authority
- US
- United States
- Prior art keywords
- substrate
- solvent
- percent
- resin
- water
- 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
- 239000000758 substrate Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 239000000126 substance Substances 0.000 claims abstract description 20
- -1 e.g. Substances 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 9
- 239000004753 textile Substances 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 25
- 239000004744 fabric Substances 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 claims description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 150000005215 alkyl ethers Chemical class 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- 239000000839 emulsion Substances 0.000 abstract description 13
- 238000009472 formulation Methods 0.000 abstract description 11
- 238000009835 boiling Methods 0.000 abstract description 10
- 239000000835 fiber Substances 0.000 abstract description 7
- 239000004094 surface-active agent Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 238000005507 spraying Methods 0.000 abstract description 3
- 238000007598 dipping method Methods 0.000 abstract description 2
- 229920000742 Cotton Polymers 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 230000002940 repellent Effects 0.000 description 4
- 239000005871 repellent Substances 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SLGOCMATMKJJCE-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,2-difluoroethane Chemical compound FC(F)(Cl)C(Cl)(Cl)Cl SLGOCMATMKJJCE-UHFFFAOYSA-N 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- GGMQZPIDPNAGFP-UHFFFAOYSA-N 1,1-dibromo-1,2,2,2-tetrachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Br)Br GGMQZPIDPNAGFP-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- LHZGEGQZBPULEQ-UHFFFAOYSA-N 3,5-bis(methoxymethyl)-1,3,5-oxadiazinan-4-one Chemical compound COCN1COCN(COC)C1=O LHZGEGQZBPULEQ-UHFFFAOYSA-N 0.000 description 1
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
Definitions
- ABSTRACT A process for applying water-soluble chemicals to flexible substrates, e.g., textile fibers, yarns, non-woven, loomed, tufted woven and knit materials, paper and the like, which employs a readily removable carrier formulation at lower temperatures under ambient pressures consisting of preparing an aqueousoil emulsion of the chemical and its attendant assistants, catalysts or reactive or non-reactive co-chemicals, surface active agent(s) in 1 to 35 percent by weight water and 98 to 40 percent by weight of a halogenated hydrocarbon solvent boiling between about 40 to about 165 C., applying the emulsion to a flexible substrate by dipping, immersing, flooding, doctoring, spraying or the like, introducing the so-wetted substrate into a zone filled with the vapors of the halogenated
- the nature of the substrate is not critical and may be derived from natural or synthetic fibers and may be in the form of yarns, threads, films, sheets, woven, unwoven,;
- the commonly employed fibers are or derived from flax, cotton, wood, jute, polyamide, polyester, polyacrylate and polyarylonitrile and mixtures thereof. These fibers may be chemically treated as in the case of cellulose to enable their reforming as fibers, strands, threads or films Mixtures of two or more fibers from each class may becombined.
- halogenated hydrocarbon solvents useful in accordance with the present invention are those having a boiling point and resins, fire retardants and the like.
- Representativeof such chemicals are the methylol or alkyl ethers of methylol compounds (dimethylol dihydroxyethylene ureas), the silicones, the fluorocarbon stain and water repellents, fluorocarbon stabilization and wrinkle resistant resins, polyethylenes, polyglycols and the inorganic salts used for five retardance.
- the fabric was after-cured for 5 minutes at 150 C. and the I wrinkle recovery angle measured according to AATCC 66- 1968 Monsanto Wrinkle Recovery Test. Durable press was measured by AATCC 124-1967. Tensile change and elongation change were both measured on an Instron Tensile Instrument, five samples run each direction and averaged. AATCC 88C 1 964 was employed to obtain crease retention values.
- control runs using only water as the formulation carrier were made in the same equipment but without the vapor zone.
- the tensile change in percent and elongation change in percent are set forth in thejollowing table V 7 between about 40 and 165 C., single species of halogen or TABLE 1(a) mixtures of halogen, saturated or ethylenically unsaturated. 5O Tensile change, Elongation change, Thus, the chlorinated methanes, chlorinated ethanes, the Percent percent fluorinated ethanes, the mixed fluorochloro and fluorobromo warp Fm warp Fm ethanes and the like.
- halogenated hydrocarbons falling within these classes are methylene chloride, chloroform, carbon tetrachloride, 1,1,1- 5 :g- :g fig :22 trichloroethane, trichloroethylene, perchloroethylene; dibromotetrachloroethane, tetrachlorodifluoroethane, dichlorotetrafluoroethane, trichlorotrifluoroethane and the EXAMPLE 2
- a /35 polyester cotton broadcloth shirting fabric was treated in the same manner as set forth in Example 1 using the formulations set forth in Table II. The durable press rating and crease resistance were measured and are set forth in the Table.
- a durable press resin dimethylol dihydroxyethylene urea
- a silicone water repellent resin or a fluorocarbon water and stain repellent resin were applied from a formulation within the teaching of the present invention to a 50/50 polyester-cotton poplin fabric.
- the fabric was wetted with formulation to about 50% wet pick-up in a Butterworth 15 inch Laboratory Padder, 1 dip l nip. The results of these operations are set forth below.
- polyester-cotton batiste The washing was conducted for 20 minutes in 1,1 ,l,-trichloroethane containing 0.0045 percent by weight dioctylsodiumsulfosuecinate, rinsed twice for 10 minutes in 1,1, l-trichloroethane and air dried. The amount of resin lost is recorded below:
- said flexible substrate is a textile fabric
- said chemicals are a durable press resin of the class methylol and alkyl ethers of methylol compounds
- a catalyst for said resin and said halogenated hydrocarbon is the same solvent as that employed to fill the vapor zone.
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86203169A | 1969-09-29 | 1969-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3658575A true US3658575A (en) | 1972-04-25 |
Family
ID=25337450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US862031A Expired - Lifetime US3658575A (en) | 1969-09-29 | 1969-09-29 | Method and compositions for treating flexible substrates |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3658575A (enrdf_load_stackoverflow) |
| JP (1) | JPS4932753B1 (enrdf_load_stackoverflow) |
| BE (1) | BE756805A (enrdf_load_stackoverflow) |
| CA (1) | CA932910A (enrdf_load_stackoverflow) |
| DE (1) | DE2047508A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2100584B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1322245A (enrdf_load_stackoverflow) |
| NL (1) | NL7014292A (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3859124A (en) * | 1972-09-25 | 1975-01-07 | Proctor Chemical Company Inc | Durable fire retardant textile materials by anhydrous solvent finishing process |
| US3995078A (en) * | 1974-04-17 | 1976-11-30 | The Dow Chemical Company | Removal of surface accumulations of treating agents and wood resins |
| US20040266643A1 (en) * | 2003-06-27 | 2004-12-30 | The Procter & Gamble Company | Fabric article treatment composition for use in a lipophilic fluid system |
| US20050000028A1 (en) * | 2003-06-27 | 2005-01-06 | Baker Keith Homer | Method for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| US20050000030A1 (en) * | 2003-06-27 | 2005-01-06 | Dupont Jeffrey Scott | Fabric care compositions for lipophilic fluid systems |
| US20050003981A1 (en) * | 2003-06-27 | 2005-01-06 | The Procter & Gamble Company | Fabric care composition and method for using same |
| US20050009723A1 (en) * | 2003-06-27 | 2005-01-13 | The Procter & Gamble Company | Surfactant system for use in a lipophilic fluid |
| US20050129478A1 (en) * | 2003-08-08 | 2005-06-16 | Toles Orville L. | Storage apparatus |
| US20070056119A1 (en) * | 2003-06-27 | 2007-03-15 | Gardner Robb R | Method for treating hydrophilic stains in a lipophlic fluid system |
| US11339331B2 (en) * | 2017-01-24 | 2022-05-24 | Neste Oyj | Biogenic low viscosity insulating oil |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2373135A (en) * | 1942-04-14 | 1945-04-10 | Du Pont | Treatment of hydroxylated polymers |
| US2731364A (en) * | 1951-08-18 | 1956-01-17 | Basf Ag | Process for improving cellulose textile materials and product thereof |
| US3023129A (en) * | 1957-11-08 | 1962-02-27 | Union Carbide Corp | Crease proofing of cellulosic textile materials |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH1471568D (enrdf_load_stackoverflow) * | 1967-10-02 | |||
| CH1702468D (enrdf_load_stackoverflow) * | 1967-12-02 |
-
0
- BE BE756805D patent/BE756805A/xx unknown
-
1969
- 1969-09-29 US US862031A patent/US3658575A/en not_active Expired - Lifetime
-
1970
- 1970-09-18 CA CA093547A patent/CA932910A/en not_active Expired
- 1970-09-26 DE DE19702047508 patent/DE2047508A1/de active Pending
- 1970-09-28 FR FR7035043A patent/FR2100584B1/fr not_active Expired
- 1970-09-28 GB GB4610970A patent/GB1322245A/en not_active Expired
- 1970-09-29 JP JP45084752A patent/JPS4932753B1/ja active Pending
- 1970-09-29 NL NL7014292A patent/NL7014292A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2373135A (en) * | 1942-04-14 | 1945-04-10 | Du Pont | Treatment of hydroxylated polymers |
| US2731364A (en) * | 1951-08-18 | 1956-01-17 | Basf Ag | Process for improving cellulose textile materials and product thereof |
| US3023129A (en) * | 1957-11-08 | 1962-02-27 | Union Carbide Corp | Crease proofing of cellulosic textile materials |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3859124A (en) * | 1972-09-25 | 1975-01-07 | Proctor Chemical Company Inc | Durable fire retardant textile materials by anhydrous solvent finishing process |
| US3995078A (en) * | 1974-04-17 | 1976-11-30 | The Dow Chemical Company | Removal of surface accumulations of treating agents and wood resins |
| WO2005003281A1 (en) * | 2003-06-27 | 2005-01-13 | The Procter & Gamble Company | Delivery system for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| US20070056119A1 (en) * | 2003-06-27 | 2007-03-15 | Gardner Robb R | Method for treating hydrophilic stains in a lipophlic fluid system |
| US20050000027A1 (en) * | 2003-06-27 | 2005-01-06 | Baker Keith Homer | Delivery system for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| US20050000030A1 (en) * | 2003-06-27 | 2005-01-06 | Dupont Jeffrey Scott | Fabric care compositions for lipophilic fluid systems |
| US20050003981A1 (en) * | 2003-06-27 | 2005-01-06 | The Procter & Gamble Company | Fabric care composition and method for using same |
| US20050009723A1 (en) * | 2003-06-27 | 2005-01-13 | The Procter & Gamble Company | Surfactant system for use in a lipophilic fluid |
| US20040266643A1 (en) * | 2003-06-27 | 2004-12-30 | The Procter & Gamble Company | Fabric article treatment composition for use in a lipophilic fluid system |
| WO2005003282A1 (en) * | 2003-06-27 | 2005-01-13 | The Procter & Gamble Company | Method for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| US8148315B2 (en) | 2003-06-27 | 2012-04-03 | The Procter & Gamble Company | Method for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| US20050000028A1 (en) * | 2003-06-27 | 2005-01-06 | Baker Keith Homer | Method for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| US7202202B2 (en) | 2003-06-27 | 2007-04-10 | The Procter & Gamble Company | Consumable detergent composition for use in a lipophilic fluid |
| US7318843B2 (en) | 2003-06-27 | 2008-01-15 | The Procter & Gamble Company | Fabric care composition and method for using same |
| AU2004253930B2 (en) * | 2003-06-27 | 2008-04-03 | The Procter & Gamble Company | Delivery system for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| AU2004253933B2 (en) * | 2003-06-27 | 2008-04-03 | The Procter & Gamble Company | Method for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| US7462589B2 (en) | 2003-06-27 | 2008-12-09 | The Procter & Gamble Company | Delivery system for uniform deposition of fabric care actives in a non-aqueous fabric treatment system |
| US20050129478A1 (en) * | 2003-08-08 | 2005-06-16 | Toles Orville L. | Storage apparatus |
| US11339331B2 (en) * | 2017-01-24 | 2022-05-24 | Neste Oyj | Biogenic low viscosity insulating oil |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7014292A (enrdf_load_stackoverflow) | 1971-03-31 |
| BE756805A (fr) | 1971-03-29 |
| FR2100584B1 (enrdf_load_stackoverflow) | 1973-11-30 |
| FR2100584A1 (enrdf_load_stackoverflow) | 1972-03-24 |
| JPS4932753B1 (enrdf_load_stackoverflow) | 1974-09-02 |
| GB1322245A (en) | 1973-07-04 |
| DE2047508A1 (de) | 1971-04-29 |
| CA932910A (en) | 1973-09-04 |
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