GB766273A - Improvements in or relating to the curing of polyepoxides - Google Patents
Improvements in or relating to the curing of polyepoxidesInfo
- Publication number
- GB766273A GB766273A GB20967/54A GB2096754A GB766273A GB 766273 A GB766273 A GB 766273A GB 20967/54 A GB20967/54 A GB 20967/54A GB 2096754 A GB2096754 A GB 2096754A GB 766273 A GB766273 A GB 766273A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyether
- fluoborate
- agents
- glycidyl
- curing
- 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
Links
- 229920000647 polyepoxide Polymers 0.000 title 1
- 229920000570 polyether Polymers 0.000 abstract 11
- 239000004744 fabric Substances 0.000 abstract 10
- 239000000203 mixture Substances 0.000 abstract 10
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 9
- 239000004753 textile Substances 0.000 abstract 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- 239000003795 chemical substances by application Substances 0.000 abstract 6
- 229920000742 Cotton Polymers 0.000 abstract 5
- -1 fatty acid esters Chemical class 0.000 abstract 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 5
- 229910052751 metal Inorganic materials 0.000 abstract 5
- 239000002184 metal Substances 0.000 abstract 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 4
- 239000004902 Softening Agent Substances 0.000 abstract 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 4
- 239000000194 fatty acid Substances 0.000 abstract 4
- 229930195729 fatty acid Natural products 0.000 abstract 4
- 239000000463 material Substances 0.000 abstract 4
- 229920000151 polyglycol Polymers 0.000 abstract 4
- 239000010695 polyglycol Substances 0.000 abstract 4
- BIOOACNPATUQFW-UHFFFAOYSA-N calcium;dioxido(dioxo)molybdenum Chemical compound [Ca+2].[O-][Mo]([O-])(=O)=O BIOOACNPATUQFW-UHFFFAOYSA-N 0.000 abstract 3
- 150000002739 metals Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- RGDDVTHQUAQTIE-UHFFFAOYSA-N 2-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC=C1O RGDDVTHQUAQTIE-UHFFFAOYSA-N 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 2
- 229920000609 methyl cellulose Polymers 0.000 abstract 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 abstract 2
- 239000001923 methylcellulose Substances 0.000 abstract 2
- 235000010981 methylcellulose Nutrition 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- 238000011084 recovery Methods 0.000 abstract 2
- 239000001993 wax Substances 0.000 abstract 2
- 230000037303 wrinkles Effects 0.000 abstract 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 abstract 1
- LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical compound CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 abstract 1
- XACKAZKMZQZZDT-MDZDMXLPSA-N 2-[(e)-octadec-9-enyl]butanedioic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCC(C(O)=O)CC(O)=O XACKAZKMZQZZDT-MDZDMXLPSA-N 0.000 abstract 1
- ZPJDFKVKOFGAFV-UHFFFAOYSA-N 2-octadecylbutanedioic acid Chemical compound CCCCCCCCCCCCCCCCCCC(C(O)=O)CC(O)=O ZPJDFKVKOFGAFV-UHFFFAOYSA-N 0.000 abstract 1
- JBNOVHJXQSHGRL-UHFFFAOYSA-N 7-amino-4-(trifluoromethyl)coumarin Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N)=CC=C21 JBNOVHJXQSHGRL-UHFFFAOYSA-N 0.000 abstract 1
- 229920002955 Art silk Polymers 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 240000000491 Corchorus aestuans Species 0.000 abstract 1
- 235000011777 Corchorus aestuans Nutrition 0.000 abstract 1
- 235000010862 Corchorus capsularis Nutrition 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052793 cadmium Inorganic materials 0.000 abstract 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 1
- 125000005456 glyceride group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 238000004900 laundering Methods 0.000 abstract 1
- 150000004668 long chain fatty acids Chemical class 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052755 nonmetal Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 239000002964 rayon Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052712 strontium Inorganic materials 0.000 abstract 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/55—Epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A glycidyl polyether from epichlorhydrin and a polyhydric phenol or alcohol is cured by a salt of a metal of atomic weight between 24 and 210 with an inorganic acid of the formula Ha[XwFy], wherein X is a non-metal of atomic weight above 2, w and y are integers and a is the valency of the acid. Preferred salts are fluoborates or fluosilicates of metals of Groups 1 to IV and VIII, e.g. copper, zinc, iron, cadmium, nickel, cobaltous, magnesium and strontium fluoborate and cobaltous, copper and magnesium fluosilicate. The process is particularly applicable for hardening glycidyl ethers which have been used for treating textiles (see Group IV (c)). The polyethers and curing agents may be mixed in solvents to which diluents may be added or the polyethers may be used in emulsion form. Lists of suitable solvents and diluents and emulsifying agents are given. Pigments, plasticisers and other resins may also be added. Textile softening-agents, e.g. epoxidized oils, glycidyl-D -decyl ether, pentadecyl phenol, octadecyl succinic acid, sulphonated waxes or alcohols, dimerized long-chain acids, or polyglycol fatty acid esters may be added to textile treating compositions. In Example I zinc fluoborate was used as curing agent for a glycidyl polyether from glycerol in an aqueous textile treating composition containing also methyl cellulose, a copolymer of vinyl methyl ether and maleic anhydride, and a polyglycol fatty acid ester. II. Fluoborates of a number of different metals are compared as curing agents in textile treating compositions. III. Zinc fluoborate is used as curing agent in a number of textile treating compositions containing different softening agents. IV. Films are prepared from a mixture of lead fluoborate with a glycidyl polyether prepared from epichlorhydrin and 2 - hydroxy - ethoxy methyl - 2,4 - dimethyl pentanediol-1,5. V. Films are prepared from a mixture of cadmium fluoborate with a polyether from bisphenol and epichlorohydrin. VI is similar to V but uses copper fluoborate.ALSO:Textile materials are impregnated with compositions containing a glycidyl polyether of a polyhydric phenol or alcohol and a metal fluoborate or fluosilicate and the polyether is cured. The treated materials have improved resistance to shrinkage, good wrinkle recovery, resistance to scorch and laundering properties and no chlorine retention. The polyether may be applied first and a solution of the curing salt sprayed on to the material. The compositions may be aqueous solutions or emulsions or organic solvents may be used. Solvents and emulsifying agents are listed in the Specification. Curing is effected by heating. Plasticizers or softening agents, e.g. epoxidized glyceride, epoxidized soya bean oil, glycidyl delta decyl ether, pentadecyl phenol, octadecyl or octadecenyl succinic acid, sulphonated waxes or alcohols, dimerized long chain fatty acids or nonionic fatty acid esters of higher polyglycols may be included in the compositions. The solutions may be applied to one surface only e.g. of a fabric with a silk face and cotton back. They may also be applied locally to fabrics. Repeated applications may be made, the amount of polyether added to the fabric depending on the purpose for which the fabric is required. The fabric may be for example of cotton, linen, natural or artificial silk, jute, rayon, or wool and may be woven, knitted or netted. Threads, fibres or filaments may also be treated. In examples I cotton cloth was impregnated with an aqueous solution containing a polyether from glycerol and epichlorohydrin, methyl cellulose, a copolymer of vinyl methyl ether and maleic anhydride, a polyglycol fatty acid ester and zinc fluoborate as curing agent, dried and cured at 160 DEG C. for 5 mins. The properties of the treated cloth are compared with those of cloth treated with other materials. II Fluoborates of a number of different metals were employed as curing agents in textile-treating compositions of the kind described in Example I and the wrinkle recovery values of the treated cotton sheets were compared. III A series of impregnating solutions as described in Example I but with different softening agents were used on cotton cloth and the properties of the treated cloth were compared.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US344561XA | 1953-07-21 | 1953-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB766273A true GB766273A (en) | 1957-01-16 |
Family
ID=21876535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20967/54A Expired GB766273A (en) | 1953-07-21 | 1954-07-19 | Improvements in or relating to the curing of polyepoxides |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE530494A (en) |
| CH (1) | CH344561A (en) |
| DE (1) | DE1105376B (en) |
| FR (1) | FR1109462A (en) |
| GB (1) | GB766273A (en) |
| NL (2) | NL189324B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242130A (en) * | 1961-11-09 | 1966-03-22 | Lubrizol Corp | Phosphorodithioic zinc salt based corrosion inhibiting composition comprising an epoxy resin, acylated polyamine and filler |
| US3432440A (en) * | 1965-02-11 | 1969-03-11 | Celanese Coatings Co | Epoxy curing agents comprising a fluoborate salt and a hydrolyzable ester |
| US4092296A (en) * | 1973-08-13 | 1978-05-30 | Skiff Russell A | Epoxy resin compositions |
| US10617617B1 (en) | 2018-12-04 | 2020-04-14 | Momentive Performance Materials Inc. | Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
| US11090255B2 (en) | 2018-12-04 | 2021-08-17 | Momentive Performance Materials Inc. | Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
| US11179312B2 (en) | 2017-06-05 | 2021-11-23 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1200349A (en) * | 1981-12-14 | 1986-02-04 | Thomas F. Brownscombe | Curable epoxy compositions, their preparation and formed articles therefrom |
| US4751143A (en) * | 1984-09-20 | 1988-06-14 | Celanese Corporation | Process for treating chemically stabilized, adhesive activated polyester material, polyester material treated by the process and an improved finish composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL73161C (en) * | 1945-07-13 | 1900-01-01 | ||
| AT172353B (en) * | 1948-10-01 | 1952-09-10 | Hoechst Ag | Process for the production of compounds with high chemical resistance that harden quickly in the cold |
-
0
- BE BE530494D patent/BE530494A/xx unknown
- NL NL95049D patent/NL95049C/xx active
- NL NLAANVRAGE8300781,A patent/NL189324B/en unknown
-
1954
- 1954-07-19 DE DEN9216A patent/DE1105376B/en active Pending
- 1954-07-19 GB GB20967/54A patent/GB766273A/en not_active Expired
- 1954-07-19 FR FR1109462D patent/FR1109462A/en not_active Expired
- 1954-07-19 CH CH344561D patent/CH344561A/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242130A (en) * | 1961-11-09 | 1966-03-22 | Lubrizol Corp | Phosphorodithioic zinc salt based corrosion inhibiting composition comprising an epoxy resin, acylated polyamine and filler |
| US3432440A (en) * | 1965-02-11 | 1969-03-11 | Celanese Coatings Co | Epoxy curing agents comprising a fluoborate salt and a hydrolyzable ester |
| US4092296A (en) * | 1973-08-13 | 1978-05-30 | Skiff Russell A | Epoxy resin compositions |
| US11179312B2 (en) | 2017-06-05 | 2021-11-23 | Momentive Performance Materials Inc. | Aqueous compositions for the treatment of hair |
| US10617617B1 (en) | 2018-12-04 | 2020-04-14 | Momentive Performance Materials Inc. | Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
| WO2020117509A1 (en) | 2018-12-04 | 2020-06-11 | Momentive Performance Materials Inc. | Polycarboxylic acid compounds for the treatment of fibrous amino acid based substrates, especially hair |
| US11090255B2 (en) | 2018-12-04 | 2021-08-17 | Momentive Performance Materials Inc. | Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1105376B (en) | 1961-04-27 |
| NL95049C (en) | |
| FR1109462A (en) | 1956-01-30 |
| NL189324B (en) | |
| BE530494A (en) | |
| CH344561A (en) | 1960-02-15 |
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