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
  • 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
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
  • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
  • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
  • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
  • D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
• • 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
• • 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
  • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
  • D06M15/3568—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing silicon
• • 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
  • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
• • 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
  • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
  • D06M2200/10—Repellency against liquids
  • D06M2200/11—Oleophobic properties
• • 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
  • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
  • D06M2200/10—Repellency against liquids
  • D06M2200/12—Hydrophobic properties

Definitions

• the present invention relates to a soil release agent for dry cleaning.
• a soil release agent also called SR processing agent
• SR processing agent in order to remove oily dirt as described above, it is sufficient to treat the surface of the garment so as to exhibit oil repellency and at the same time, to treat the garment also so as to exhibit hydrophilicity. It is obtained by copolymerizing a hydrophilic polymerizable monomer with a polymerizable monomer having a hydroxyl group.
• oily stains can be easily removed by washing the clothes in water at home.
• improvements are being made to further improve the initial soil release property and to improve the durability.
• An object of the present invention is to provide a soil release agent which is suitable for dry cleaning and has good performance.
• the present invention provides (A) a repeating unit derived from a polymerizable monomer containing fluorine, and
• a soil release agent comprising a copolymer having the formula:
• FIG. 1 is a graph showing the relationship between the ratio of the monomer (a) to the monomer (b) and the soil release property (DCSR), water repellency, and oil repellency for dry cleaning.
• DCSR soil release property
• the fluorine-containing polymerizable monomer (A) is not particularly limited, but is preferably a fluoroalkyl group-containing (methyl) acrylate having a fluoroalkyl group having 3 to 21 carbon atoms.
• Preferred specific examples of the polymerizable monomer (A) are as follows.
• polymerizable monomer (B) containing a siloxane bond is as follows.
• R is a hydrogen atom or a methyl group
• RR 2 and R 3 are the same or different from each other, and are lower (for example, carbon number 1-4) alkyl groups
• m is a number of 0-200
• n is! ⁇ 4 is the number.
• Examples of the polymerizable monomer (B) containing no siloxane bond and having a solubility parameter value of 6 to 15 include alkyl (meth) acrylates such as stearyl (meth) acrylate, vinyl chloride, butadiene, styrene, and acetic acid. Vinyl and vinyl stearate.
• solubility parameter (SP) is a value calculated according to the definition described in Small literature (Small, Journal of Applied Chemistry 3, 71-80. Feb (195 3)).
• the solubility parameter value is 6 to 15, particularly preferably 7 to 12.
• a crosslinkable monomer is used as a part of the monomer (B).
• the crosslinkable monomer is, for example, a hydroxyalkyl (meth) acrylate such as 3-chloro-2-hydroxypropyl (meth) acrylate or a (meth) acrylamide such as N-methylol (meth) acrylamide.
• the amount of the crosslinkable monomer is preferably 0 to 10% by weight, more preferably 0.5 to 5% by weight of the monomer (B).
• the copolymer is composed of 10 to 90% by weight of the monomer (A) and 90 to 10% by weight of the monomer (B), preferably 10 to 60% by weight of the monomer (A). And 90 to 40% by weight of the monomer (B), and more preferably 10 to 50% by weight of the monomer (A) and 90 to 50% by weight of the monomer (B). .
• the copolymer having a monomer (A) ratio of 10 to 50% by weight has the most remarkable effect of removing dirt (hereinafter referred to as DCSR property) by dry cleaning, which is the object of the present invention.
• DCSR property dirt
• Copolymers having a monomer (A) ratio of 10 to 60% by weight have good oil repellency in this range, although the range in which the DCSR property is slightly reduced is included.
• the ratio of the monomer (A) is in the range of 50 to 60% by weight, the DCSR property is slightly lowered, but instead the oil repellency is excellent.
• the molecular weight of the copolymer is usually from 100 to 100,000, preferably from 500 to 500,000.
• the copolymerization reaction is performed by an emulsion polymerization method, a solution polymerization method, or the like.
• the surfactant and the polymerization initiator used are not particularly limited. Almost any of the various anionic, cationic or nonionic emulsifiers can be used as surfactants.
• the amount of the surfactant used in the emulsion polymerization is usually 0.5 to 20 parts by weight per 100 parts by weight of the copolymer.
• various polymerization initiators such as organic peroxides, azo compounds, and persulfates, and ionizing radiation such as 7 rays can be used.
• the soil release agent comprises a copolymer and a medium.
• the medium can be any solvent, including water, organic solvents such as alcohols, esters, It may be ketone or the like.
• the soil release agent for dry cleaning of the present invention can be applied by any method depending on the type of the object to be treated. For example, a method of adhering to the surface of the object to be treated and drying it by a known method of coating such as immersion or coating can be adopted. If necessary, curing may be performed by applying together with a suitable crosslinking agent. Furthermore, the soil remover for dry cleaning of the present invention may be mixed with other polymer blenders, and other water repellents, oil repellents, insect repellents, flame retardants, antistatic agents, softeners, and stainproofers. Of course, it is also possible to add additives such as agents appropriately and use them together. In the case of immersion, the copolymer concentration in the immersion liquid is usually from 0.5 to 10% by weight. In the case of coating, the copolymer concentration in the coating solution is usually 0.1 to 5% by weight.
• the fiber product that can be treated with the soil release agent for dry cleaning of the present invention is not particularly limited, and various examples can be given.
• animal and plant natural fibers such as cotton, hemp, wool, and silk
• various synthetic fibers such as polyamide, polyester, polyvinyl alcohol, polyacrylonitrile, polyvinyl chloride, and polypropylene
• semi-synthetic fibers such as rayon and acetate.
• Inorganic fibers such as glass fibers, carbon fibers, and asbestos fibers; or mixtures of these fibers.
• the textile product may be in any form of fiber, yarn, cloth and the like.
• Specific examples of clothes treated with the dry cleaning soil release agent of the present invention include sportswear such as ski wear, tennis wear, golf wear, and rider wear.
• the water repellency and oil repellency shown in the following examples are shown on the following scale. It is. That is, the water repellency is represented by the water repellency No. by the spray method of JI SL-1092 (see Table 1 below).
• the oil repellency is determined by placing a few drops (approximately 4 places in diameter) of the test solution shown in Table 2 below on a sample cloth at a nick, and measuring the permeation state after 30 seconds (AATCC—TM118—1966). Test showing no penetration The highest value of the oil repellency provided by the solution is defined as the oil repellency.
• a test of the soil release property (DCS R property) in dry cleaning was performed as follows. That is, spread the test cloth on blotting paper spread horizontally, drop 5 drops of dirty motor oil (SAE 20W-40, which was put into the engine of a small passenger car and discharged after running 400 OKm), and the polyethylene was dropped on it. After applying a weight of 2 kg, place a weight of 2 kg, remove the weight and polyethylene sheet after 60 seconds, wipe off excess oil, leave it at room temperature for 24 hours, and make it 45 g with test cloth and ballast cloth with a dry cleaning tester. Dry-clean with 3.78 liters of Parken for 5 minutes at room temperature and air dry. The dried test cloth shall be compared with the standard photographic plate for the residual stain condition, and shall be indicated with the relevant judgment grade (see Table 3).
• the standard photographic plate used was AAT CC Test Method 130- 1970.
• the soil release property (HLSR property) test in a home laundry was performed as follows. That is, similar to the DCSR test, after a dirty motor oil is applied, the weight of the test cloth and ballast cloth is reduced to 1 kg with a fully automatic washing machine for home use, 30 liters of water, and a detergent (trade name: High Top, Wash with 25 g for 5 minutes. After that, rinse with water for 3 minutes, air-dry after 3 minutes of dehydration, The state of the residual stain was determined in the same manner as in the DCSR test.
• 50 g, stearyl Akurireto 25.5 g, N- 1.5 g of methylol acrylamide, 320 g of pure water, 30 g of acetone, 0.3 g of acetic acid, 6 g of polyoxyethylene alkylfurnyl ether, and 10 g of alkyltrimethylammonium chloride are added, and the mixture is stirred. It was emulsified and dispersed by ultrasonic waves for minutes. 0.75 g of azobisisobutylamidine monohydrochloride was added and reacted for 5 hours. The resulting emulsion contained a copolymer concentration of 20% by weight.
• the copolymer had the composition shown in Table 4.
• the emulsion was diluted with pure water to a copolymer concentration of 1.0% by weight, and a cotton cloth was immersed in the diluted solution and squeezed with a mangle to obtain a pickup of 60%.
• the mixture was dried for 3 minutes and heat-treated at 150 ° C for 3 minutes. This cotton cloth was evaluated for water repellency, oil repellency, and stain release property. Table 4 shows the results.
• Example 4 The same procedure as in Example 1 was repeated using various monomers.
• the c result of polymerized using autoclave instead flask shown in Table 4 show DCS R resistance and water repellent, the relationship between the oil repellency in Figure 1 on the basis of these results .
• Table 4
• NMA N-methylol atarylamide
• the dirt-removing agent for dry cleaning of the present invention has an effect (dirt-removing property) for the first time by dry cleaning. That is, no effect can be expected from washing in water. In this respect, it is completely different from the conventionally known soil release agent (SR processing agent).
• SR processing agent soil release agent
• the soil release property by dry cleaning is good.
• the dry-cleaning soil release agent of the present invention When the dry-cleaning soil release agent of the present invention is used for clothes, when the clothes are dry-cleaned, the stains are surprisingly easily removed so as to be incomparable to washing in water.

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• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Detergent Compositions (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Paper (AREA)

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Cited By (7)

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Citations (4)

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• 1993
  • 1993-07-02 EP EP93914946A patent/EP0609456B1/en not_active Expired - Lifetime
  • 1993-07-02 WO PCT/JP1993/000911 patent/WO1994001510A1/ja active IP Right Grant
  • 1993-07-02 DE DE69331184T patent/DE69331184T2/de not_active Expired - Fee Related
  • 1993-07-07 TW TW082105418A patent/TW301671B/zh active
• 1996
  • 1996-09-27 US US08/722,519 patent/US5883067A/en not_active Expired - Fee Related

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