US3850818A - Antistatic softening composition containing a quaternary ammonium salt and a ethenoxy quaternary ammonium salt - Google Patents
Antistatic softening composition containing a quaternary ammonium salt and a ethenoxy quaternary ammonium salt Download PDFInfo
- Publication number
- US3850818A US3850818A US00290345A US29034572A US3850818A US 3850818 A US3850818 A US 3850818A US 00290345 A US00290345 A US 00290345A US 29034572 A US29034572 A US 29034572A US 3850818 A US3850818 A US 3850818A
- Authority
- US
- United States
- Prior art keywords
- quaternary ammonium
- ammonium salt
- percent
- softening composition
- antistatic
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- -1 ethenoxy quaternary ammonium salt Chemical class 0.000 title claims abstract description 23
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000000654 additive Substances 0.000 claims abstract description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 8
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims description 3
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 claims description 3
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 8
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract description 5
- 239000004202 carbamide Substances 0.000 abstract description 5
- 239000000600 sorbitol Substances 0.000 abstract description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract description 4
- 150000001298 alcohols Chemical class 0.000 abstract description 4
- 150000002334 glycols Chemical class 0.000 abstract description 4
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 239000004753 textile Substances 0.000 description 8
- 239000004902 Softening Agent Substances 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000003839 salts Chemical group 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 230000003068 static effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920002972 Acrylic fiber Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010016322 Feeling abnormal Diseases 0.000 description 2
- QGGDXDGBZVPEEG-UHFFFAOYSA-N [NH4+].[Cl-].[Cl-].[NH3+]C Chemical compound [NH4+].[Cl-].[Cl-].[NH3+]C QGGDXDGBZVPEEG-UHFFFAOYSA-N 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- FLNKWZNWHZDGRT-UHFFFAOYSA-N azane;dihydrochloride Chemical compound [NH4+].[NH4+].[Cl-].[Cl-] FLNKWZNWHZDGRT-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GUQGYHBUINQTSV-UHFFFAOYSA-N azane;methanamine Chemical compound N.NC GUQGYHBUINQTSV-UHFFFAOYSA-N 0.000 description 1
- 239000004106 carminic acid Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- 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
- D06M13/10—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 oxygen
- D06M13/144—Alcohols; Metal alcoholates
-
- 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
- D06M13/10—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 oxygen
- D06M13/144—Alcohols; Metal alcoholates
- D06M13/148—Polyalcohols, e.g. glycerol or glucose
-
- 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
- D06M13/322—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 nitrogen
- D06M13/372—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 nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
- D06M13/322—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 nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- 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
- D06M13/322—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 nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
Definitions
- R represents an alkyl group of C, ,-C R, represents an alkyl group of C -C or benzyl group
- X represents Cl, Br or C H SO
- m and n each represent an integer of more than 1 inclusive, with the proviso that m n is 20-100, and 05-15 percent by weight of one or more additives selected from the group consisting of alcohols of lower than C inclusive, glycols, glycerol, sorbitol and urea.
- the present invention relates to a softening composition which is stable even at a high concentration and which imparts an excellent antistatic property to the treated textile products.
- Softening agents have been used frequently as finishing agents for textile products. They are used mainly for finishing of washed underwear and diapers to impart a soft feeling to the textile products. Important properties required of softening agents are as follows:
- compositions of softening agents have. been known, but most of them contain quaternary ammonium salts having two long chain alkyl groups as their main ingredients.
- some of the known compositions contain, in addition to said main ingredient, a nonionic surfactant such as an alkylphenol ethylene oxide adduct and a solvent such as an alcohol or glycol to improve the stability of the solution.
- a nonionic surfactant such as an alkylphenol ethylene oxide adduct
- a solvent such as an alcohol or glycol
- the softening agents do not freeze at a low temperature around the freezing point, or even if they are frozen, their viscosities are recovered when the temperature is elevated again to room temperature.
- an antistatic agent for obtaining a composition having an antistatic property.
- a conventionally known antistatic agent such as stearyl trimethylammonium chloride
- a softening agent composition containing a quaternary ammonium salt having two long chain alkyl SUMMARY OF THE INVENTION The present invention relates to a softening composi tion having an excellent softening effect, particularly a sufficientstability even at a high concentration, and an excellent antistatic effect upon treated textile products.
- the present invention relates to an antistatic softeningcomposition characterized by containing 4-10 percent by weight of a quaternary ammonium salt represented by the following general formula (1):
- R and R each represent an alkyl group of C -C R and R each represent an alkyl group of C -C benzyl group or (C H O),,H (n 1 3) and X represents Cl, Br or C I-I SO. 0.1-5 percent by weight of ethenoxy quaternary ammonium salt represented'by the following general formula (II):
- R represents an alkyl group of C -C
- R represents an alkyl group of C,-C or benzyl group
- X represents Cl, Br or C I-I SO
- m and n each represent an integer of more than 1 inclusive, with the priviso than "1+" is 20-100 and 0.5-15 percent by weight of one or more additives selected from the group consisting of alcohols of lower than C inclusive, glycols, glycerol, sorbitol and urea.
- Preferred R and R are C -C alkyl groups and preferred R and R are C -C alkyl groups and benzyl group.
- Preferred R are those of C -C and the sum of m and n is preferably 30-70.
- the preferred amount of the ethenoxy quaternary ammonium salt of the above general formula (II) is 1.0-5.0 percent by weight and the preferredamount of the additives is 3-8 percent by weight;
- the most preferred quaternary ammonium salts of the above general formula (I) are distearyl dimethylammonium chloride and dihydrogenated tallowalkyl dimethylammonium chloride.
- EXAMPLE 1 (This example is to demonstate the effects based on the constituents of the compositions.)
- compositions A through G are those of the present invention and the compositions H through K are comparative ones. Percentages in the table are shown in weight and the remainder is the amount of water.
- Viscosity, antistatic property and softening property shown in Table l are measured according to the methods which will be described below. The results of the measurements are shown by four grades of G, O, A and X,@ being the most excellent (the lowest in viscosity).
- Quaternary ammonium salts in the table are compounds of the general formula (I) and the ethenoxy quaternary salts are ethenoxy quaternary ammonium salts of the general formula (ll).
- the symbol E indicates ethylene oxide.
- composition directly after blending was allowed to stand at room temperature for 6 months and then at 50 C for 3 months, frozen at 30 C, thawed at room temperature and then frozen again. This procedure was repeated 5 times. Four samples of each composition were measured at 30 C with Brookfield type viscometer. The unit of numerals in the table is centi-poises.
- Pieces of cotton towel, cotton plain fabric for diaper and blanket made from polyacrylonitrile fiber were washed in a usual manner, treated with 0.1 percent and 0.3 percent solutions of each softening composition and finally dried.
- the samples were tested by 5 men and 5 women according to handling (tactile impression) and their feelings were evaluated by the points compared with the standard criteria.
- the numerals in Table 2 are the sums of the points. The larger the nu meral, th softer the textile.
- Viscosity The composition immediately after the blending was allowed to stand at room temperature for one month ter.
- the unit of numerals in the table is centi-poises.
- An antistatic softening composition consisting essentially of 4-10 percent by weight of a quaternary ammonium salt of the formula (1):
- R represents an alkyl group of C -C
- R represents an alkyl group of C -C or benzyl group
- X represents Cl, Br or C H SO
- m and n each represent an integer of more than 1 inclusive, with the privisio that m n is 20-100, 0.5 percent by weight of one or more additives selected from the group consist ing of alcohols of lower than C inclusive, glycols, glycerol, sorbitol and urea, the balance of said composition being water.
- R and R each represents an alkyl group of C -C
- R and R each represents an alkyl group of C -C or benzyl group
- R represents an alkyl group of C -C and the sum of m and n is 30-70.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46074276A JPS5124638B2 (pt) | 1971-09-23 | 1971-09-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3850818A true US3850818A (en) | 1974-11-26 |
Family
ID=13542413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00290345A Expired - Lifetime US3850818A (en) | 1971-09-23 | 1972-09-19 | Antistatic softening composition containing a quaternary ammonium salt and a ethenoxy quaternary ammonium salt |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3850818A (pt) |
| JP (1) | JPS5124638B2 (pt) |
| AU (1) | AU468515B2 (pt) |
| CH (1) | CH544181A (pt) |
| DE (1) | DE2246866C3 (pt) |
| ES (1) | ES406891A1 (pt) |
| FR (1) | FR2153434B1 (pt) |
| GB (1) | GB1404494A (pt) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3958059A (en) * | 1973-10-01 | 1976-05-18 | The Procter & Gamble Company | Fabric treatment composition |
| US3959155A (en) * | 1973-10-01 | 1976-05-25 | The Procter & Gamble Company | Detergent composition |
| US3974076A (en) * | 1974-01-11 | 1976-08-10 | The Procter & Gamble Company | Fabric softener |
| US4038196A (en) * | 1975-03-12 | 1977-07-26 | Kao Soap Co., Ltd. | Softening agent for woven fabrics |
| US4076632A (en) * | 1977-02-22 | 1978-02-28 | The Procter & Gamble Company | Fabric softener |
| US4084034A (en) * | 1976-08-23 | 1978-04-11 | Nalco Chemical Company | Sodium chloride and polydiallyl dimethyl ammonium chloride as an electroconductive additive |
| US4102825A (en) * | 1976-10-01 | 1978-07-25 | Kao Soap Co., Ltd. | Liquid light-duty detergent composition |
| US4157307A (en) * | 1978-08-07 | 1979-06-05 | The Procter & Gamble Company | Liquid fabric softener |
| US4174304A (en) * | 1975-08-01 | 1979-11-13 | Bullen Chemical Company Midwest, Inc. | Surfactant system |
| US4330526A (en) * | 1976-03-22 | 1982-05-18 | Kao Soap Co., Ltd. | Shampoo composition |
| US4399045A (en) * | 1980-11-18 | 1983-08-16 | The Procter & Gamble Company | Concentrated fabric softening compositions |
| DE3324056A1 (de) * | 1982-07-05 | 1984-01-19 | Lion Corp., Tokyo | Zusatz fuer koernige wasch- und reinigungsmittel |
| US4439335A (en) * | 1981-11-17 | 1984-03-27 | The Procter & Gamble Company | Concentrated fabric softening compositions |
| US4485048A (en) * | 1982-08-09 | 1984-11-27 | Akzona Incorporated | Ethoxylated quaternary benzyl compounds |
| US4844822A (en) * | 1987-07-06 | 1989-07-04 | The Dial Corporation | Softener/antistat compositions |
| US6369159B1 (en) | 1987-05-13 | 2002-04-09 | Pdm Holdings Corp. | Antistatic plastic materials containing epihalohydrin polymers |
| WO2023239891A1 (en) | 2022-06-10 | 2023-12-14 | Lubrizol Advanced Materials, Inc. | Thermoplastic polyurethanes with high temperature stability and uses thereof |
| WO2024102687A1 (en) | 2022-11-08 | 2024-05-16 | Lubrizol Advanced Materials, Inc. | High resilient thermoplastic polyurethanes and uses thereof |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5126373A (en) * | 1974-08-26 | 1976-03-04 | Kasuga Electric Co | Chojakusokotaino soko hisokokenchisochi |
| JPS5126372A (en) * | 1974-08-26 | 1976-03-04 | Kasuga Electric Co | Chojakusokotaino soko hisokokenchisochi |
| DE2459354C2 (de) * | 1974-12-16 | 1986-03-27 | Hoechst Ag, 6230 Frankfurt | Waescheweichspuelmittelkonzentrat mit desinfizierenden eigenschaften |
| DE2525610C2 (de) * | 1975-06-09 | 1985-04-11 | Henkel KGaA, 4000 Düsseldorf | Kationische Avivagemittel mit verbesserter Kaltwasserlöslichkeit |
| GR67665B (pt) | 1979-05-21 | 1981-09-02 | Unilever Nv | |
| JPS5713958U (pt) * | 1980-06-24 | 1982-01-25 | ||
| US4401577A (en) * | 1980-09-25 | 1983-08-30 | Akzona Incorporated | Quaternary ammonium dihydroborates in fabric softener formulations |
| DE3263800D1 (en) * | 1981-01-16 | 1985-07-04 | Procter & Gamble | Textile treatment compositions |
| GB2115847B (en) * | 1982-03-02 | 1984-04-04 | Derek James Frost | Antistatic composition for synthetic textile materials |
| SE464139B (sv) * | 1983-05-11 | 1991-03-11 | Colgate Palmolive Co | Koncentrerad textilmjukgoerande komposition och foerfaranden foer tillverkning av densamma |
| JPS60263384A (ja) * | 1984-06-11 | 1985-12-26 | Mitsubishi Plastics Ind Ltd | 記録デイスク収納カバ− |
| GB8500958D0 (en) * | 1985-01-15 | 1985-02-20 | Unilever Plc | Fabric conditioning composition |
| GB8500959D0 (en) * | 1985-01-15 | 1985-02-20 | Unilever Plc | Fabric conditioning method |
| JPH0533493Y2 (pt) * | 1988-08-24 | 1993-08-25 | ||
| EP0890671A3 (de) * | 1997-07-10 | 2000-02-23 | Ciba SC Holding AG | Verwendung von modifizierten Fettaminen zur Verhinderung von Ablagerungen von niedermolekularen Nebenprodukten auf textilen Materialien |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3154489A (en) * | 1960-07-18 | 1964-10-27 | Armour & Co | Surface active compositions |
| US3178366A (en) * | 1962-05-28 | 1965-04-13 | Armour & Co | Treating compositions for softening fibers |
| US3546115A (en) * | 1967-02-28 | 1970-12-08 | Cargill Inc | Fabric softener |
| US3573091A (en) * | 1967-11-13 | 1971-03-30 | Armour & Co | Method of preparing water-dispersible softener compositions and products thereby |
-
1971
- 1971-09-23 JP JP46074276A patent/JPS5124638B2/ja not_active Expired
-
1972
- 1972-09-19 US US00290345A patent/US3850818A/en not_active Expired - Lifetime
- 1972-09-20 GB GB4354972A patent/GB1404494A/en not_active Expired
- 1972-09-21 CH CH1377972A patent/CH544181A/fr not_active IP Right Cessation
- 1972-09-21 AU AU46960/72A patent/AU468515B2/en not_active Expired
- 1972-09-21 ES ES406891A patent/ES406891A1/es not_active Expired
- 1972-09-22 FR FR7233715A patent/FR2153434B1/fr not_active Expired
- 1972-09-23 DE DE2246866A patent/DE2246866C3/de not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3154489A (en) * | 1960-07-18 | 1964-10-27 | Armour & Co | Surface active compositions |
| US3178366A (en) * | 1962-05-28 | 1965-04-13 | Armour & Co | Treating compositions for softening fibers |
| US3546115A (en) * | 1967-02-28 | 1970-12-08 | Cargill Inc | Fabric softener |
| US3573091A (en) * | 1967-11-13 | 1971-03-30 | Armour & Co | Method of preparing water-dispersible softener compositions and products thereby |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959155A (en) * | 1973-10-01 | 1976-05-25 | The Procter & Gamble Company | Detergent composition |
| US3958059A (en) * | 1973-10-01 | 1976-05-18 | The Procter & Gamble Company | Fabric treatment composition |
| US3974076A (en) * | 1974-01-11 | 1976-08-10 | The Procter & Gamble Company | Fabric softener |
| US4038196A (en) * | 1975-03-12 | 1977-07-26 | Kao Soap Co., Ltd. | Softening agent for woven fabrics |
| US4174304A (en) * | 1975-08-01 | 1979-11-13 | Bullen Chemical Company Midwest, Inc. | Surfactant system |
| US4330526A (en) * | 1976-03-22 | 1982-05-18 | Kao Soap Co., Ltd. | Shampoo composition |
| US4084034A (en) * | 1976-08-23 | 1978-04-11 | Nalco Chemical Company | Sodium chloride and polydiallyl dimethyl ammonium chloride as an electroconductive additive |
| US4102825A (en) * | 1976-10-01 | 1978-07-25 | Kao Soap Co., Ltd. | Liquid light-duty detergent composition |
| US4076632A (en) * | 1977-02-22 | 1978-02-28 | The Procter & Gamble Company | Fabric softener |
| US4157307A (en) * | 1978-08-07 | 1979-06-05 | The Procter & Gamble Company | Liquid fabric softener |
| US4399045A (en) * | 1980-11-18 | 1983-08-16 | The Procter & Gamble Company | Concentrated fabric softening compositions |
| US4439335A (en) * | 1981-11-17 | 1984-03-27 | The Procter & Gamble Company | Concentrated fabric softening compositions |
| DE3324056A1 (de) * | 1982-07-05 | 1984-01-19 | Lion Corp., Tokyo | Zusatz fuer koernige wasch- und reinigungsmittel |
| US4485048A (en) * | 1982-08-09 | 1984-11-27 | Akzona Incorporated | Ethoxylated quaternary benzyl compounds |
| US6369159B1 (en) | 1987-05-13 | 2002-04-09 | Pdm Holdings Corp. | Antistatic plastic materials containing epihalohydrin polymers |
| US4844822A (en) * | 1987-07-06 | 1989-07-04 | The Dial Corporation | Softener/antistat compositions |
| WO2023239891A1 (en) | 2022-06-10 | 2023-12-14 | Lubrizol Advanced Materials, Inc. | Thermoplastic polyurethanes with high temperature stability and uses thereof |
| WO2024102687A1 (en) | 2022-11-08 | 2024-05-16 | Lubrizol Advanced Materials, Inc. | High resilient thermoplastic polyurethanes and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2246866A1 (de) | 1973-03-29 |
| GB1404494A (en) | 1975-08-28 |
| JPS5124638B2 (pt) | 1976-07-26 |
| FR2153434B1 (pt) | 1976-05-21 |
| ES406891A1 (es) | 1975-10-01 |
| FR2153434A1 (pt) | 1973-05-04 |
| AU4696072A (en) | 1974-03-28 |
| CH544181A (fr) | 1973-11-15 |
| DE2246866B2 (de) | 1978-08-17 |
| DE2246866C3 (de) | 1979-04-12 |
| AU468515B2 (en) | 1976-01-15 |
| JPS4841095A (pt) | 1973-06-16 |
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