GB933512A - Textile treating agents - Google Patents
Textile treating agentsInfo
- Publication number
- GB933512A GB933512A GB3715361A GB3715361A GB933512A GB 933512 A GB933512 A GB 933512A GB 3715361 A GB3715361 A GB 3715361A GB 3715361 A GB3715361 A GB 3715361A GB 933512 A GB933512 A GB 933512A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acrylate
- methylol acrylamide
- interpolymers
- acrylates
- methacrylate
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
-
- 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
- D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Interpolymers of N-methylol acrylamide compounds of formula Q-NH-CH2OH where Q is the acyl radical of acrylic or methacrylic acid, with at least one fluoroalkyl ester of formula Q-OCH2(CF2-CF2)mH where m is 1 to 6, or Q-OCH2(CF2)nF or Q-OCH2CH2(CF2)nF where n is 2 to 12, said N-methylol acrylamide constituting not less than 0,25% and not more than 5% by weight of the interpolymer, may be prepared by copolymerizing the monomers in aqueous emulsion in the presence of free radical generating catalysts. Suitable catalysts are hydrogen peroxide, benzoyl peroxide, potassium persulphate, 2,21-azodiisobutyramidine dihydrochloride and redox systems comprising potassium persulphate and sodium bisulphite. Emulsifiers, e.g. sodium lauryl sulphate, ammonium di1H,1H,7H-dodecafluoroheptyl) phosphate and octadecyltrimethyl ammonium chloride or bromide, and buffers, e.g. sodium borate, may be present. Many suitable fluoralkyl esters are listed and examples describe the preparation of interpolymers of N-methylol acrylamide or methacrylamide with (2) 1H,1H-pentadecafluorooctyl acrylate, (3) 1H,1H-nonadecafluorodecyl acrylate, (4, 6 and 8) 1H,1H,11H-eicosafluorohendecyl and 1H,1H,7H-dodecafluoroheptyl acrylates, (5 and 9) 1H,1H,11H-eicosafluorohendecyl and 1H,1H,5H-octafluoropentyl acrylates or methacrylates, (7) 1H,1H,9H-hexadecafluorononyl acrylate or methacrylate, (10) 1H,1H-pentafluoropropyl acrylate or methacrylate, (11) 1H,1H,9H-hexadecafluorononyl and 1H,1H-pentafluoropropyl acrylates, and (12) 1H,1H,2H,2H-tridecafluorooctyl methacrylate; and (13) interpolymers of N-methylol acrylamide with a mixture of methacrylates of formula F(CF2)nCH2CH2O.CO.C(CH3)=CH2 where n is 6, 8 and 10. Aqueous dispersions of the polymers may be applied to textile fabrics, paper and regenerated cellulose sheets, dried and cured by heating to impart water- and oil-repellency thereto. In Example 14 strips of regenerated cellulose film are padded with aqueous dispersions of copolymers of 1H,1H,9H-hexadecafluorononyl acrylate, 1H,1H-pentafluoropropyl acrylate and N-methylol acrylamide. Specifications 703,434 and 703,435 are referred to.ALSO:1H,2H,2H-iodopolyfluoroalkyl acetates may be prepared by reacting vinyl acetate with 1-iodopolyfluoroalkanes in the presence of azodiisobutyronitrile. 1H,1H,2H,2H-polyfluoro-1-alkanols may be prepared by reducing the above product with an alcoholic slurry of zinc dust and concentrated hydrochloric acid, and hydrolysing the product with an alcoholic solution of potassium hydroxide. In example (1) vinyl acetate is reacted with 1-iodopentadecafluoroheptane to give 1H,2H, 2H-iodopentadecafluorononyl acetate, which is reduced and hydrolysed to give 1H,1H, 2H,2H-pentadecafluoro-1-nonanol. Specifications 703,434 and 703,435 are referred to.ALSO:Textile fabrics, e.g. of cotton, wool, nylon or polyester, are rendered oil and water repellent by impregnating with aqueous dispersions of interpolymers of N-methylol acrylamide or methacrylamide with at least one fluoroalkyl ester of formula Q-OCH2(CF2-CF2)mH where m is 1 t 6, or Q-OCH2(CF2)nF or Q-OCH2CH2(CF2)nF where n is 2 to 12 and Q is acrylyl or methacrylyl, said N-methylol compound constituting 0,25 to 5 weight per cent of the interpolymer, drying the fabric and heating, preferably at 100 DEG to 150 DEG C. The treated fabrics may be washed and dry cleaned, but after washing should be ironed to restore maximum repellent effect. Examples describe the treating of fabrics of (2) cotton and wool, (3 to 9) cotton, (10, 12 and 13) cotton poplin and (11) cotton, wool gabardine, wool worsted, nylon and polyester with aqueous dispersions of interpolymers of N-methylol acrylamide or methacrylamide with (2) 1H,1Hpentadecafluorooctyl acrylate, (3) 1H,1H-nonadecafluorodecyl acrylate, (4, 6 and 8) 1H,1H,11Heicosafluorobendecyl and 1H,1H,7H-dodecafluoroheptyl acrylates, (5 and 9) 1H,1H,11Heicosafluorobendecyl and 1H,1H,5H-octafluoropentyl acrylates or methacrylates, (7) 1H,1H,9Hhexadecafluorononyl acrylate or methacrylate, (10) 1H,1H-pentafluoropropyl acrylate or methacrylate, (11) 1H,1H,9H-hexadecafluorononyl and 1H,1H-pentafluoropropyl acrylates and (12) 1H,1H,2H,2H-tridecafluorooctyl methacrylate; and interpolymers of N-methylol acrylamide with a mixture of methacrylates of formula F(CF2)nCH2CH2O.CO.C(CH3)=CH2 where n is 6, 8 and 10. Specifications 703,434 and 703,435 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP0028014 | 1961-10-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB933512A true GB933512A (en) | 1963-08-08 |
Family
ID=7371077
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3715361A Expired GB933512A (en) | 1961-10-11 | 1961-10-17 | Textile treating agents |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH381640A (en) |
DE (1) | DE1419505A1 (en) |
GB (1) | GB933512A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5372731A (en) * | 1992-03-12 | 1994-12-13 | Bayer Aktiengesellschaft | Composition and process for the finishing of textiles |
WO1999024655A1 (en) * | 1997-11-10 | 1999-05-20 | W.L. Gore & Associates, Inc. | Water repellent restorative and process of use |
WO2004035708A1 (en) * | 2002-10-15 | 2004-04-29 | Asahi Glass Company, Limited | Water-and-oil repellant composition |
US6774176B1 (en) * | 1998-11-13 | 2004-08-10 | E. I. Du Pont De Nemours And Company | Polymers fluorinated by polymerization in mini-emulsion |
CN115850562A (en) * | 2021-09-27 | 2023-03-28 | 中国科学院上海有机化学研究所 | Fluorine-containing acrylate polymer, preparation method and application thereof, and finishing agent |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5508370A (en) * | 1991-10-17 | 1996-04-16 | Bayer Aktiengesellschaft | Water-dispersible blocked isocyanates, method of manufacture, and use thereof |
US20140165263A1 (en) | 2012-12-18 | 2014-06-19 | Ansell Limited | Fluid repellent elastomeric barrier |
CN108348020A (en) | 2015-10-30 | 2018-07-31 | 安塞尔有限公司 | Anti-leak product |
-
1961
- 1961-10-11 DE DE19611419505 patent/DE1419505A1/en active Pending
- 1961-10-17 GB GB3715361A patent/GB933512A/en not_active Expired
- 1961-10-25 CH CH1235361A patent/CH381640A/en unknown
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5372731A (en) * | 1992-03-12 | 1994-12-13 | Bayer Aktiengesellschaft | Composition and process for the finishing of textiles |
WO1999024655A1 (en) * | 1997-11-10 | 1999-05-20 | W.L. Gore & Associates, Inc. | Water repellent restorative and process of use |
US6774176B1 (en) * | 1998-11-13 | 2004-08-10 | E. I. Du Pont De Nemours And Company | Polymers fluorinated by polymerization in mini-emulsion |
WO2004035708A1 (en) * | 2002-10-15 | 2004-04-29 | Asahi Glass Company, Limited | Water-and-oil repellant composition |
US8609795B2 (en) | 2002-10-15 | 2013-12-17 | Asahi Glass Company, Limited | Water and oil repellent composition |
CN115850562A (en) * | 2021-09-27 | 2023-03-28 | 中国科学院上海有机化学研究所 | Fluorine-containing acrylate polymer, preparation method and application thereof, and finishing agent |
Also Published As
Publication number | Publication date |
---|---|
CH381640A (en) | 1964-09-15 |
DE1419505A1 (en) | 1969-01-09 |
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