MX2007013405A - Water-soluble polymer, production method thereof, and application thereof. - Google Patents

Abstract

To provide: a water-soluble polymer having excellent adsorptivity, dispersibility, and safety as well as excellent hydrophilicity, and capable of preventing coloring sufficiently and being preferably used in a detergent additive application, for example; an application thereof; a production method of the water-soluble polymer, the production method being capable of producing such a water-soluble polymer efficiently. A water-soluble polymer produced by a polymerization of a polyether compound (A) with a monomer component containing an N-vinylpyrrolidone (B), wherein the N-vinylpyrrolidone (B) is 0.01 to 0.3 parts by weight to 1 part by weight of the polyether compound (A).

Description

POLYMER SOLUBLE IN WATER, METHOD OF PRODUCTION OF THIS, AND APPLICATIONS OF THE SAME FIELD OF THE INVENTION The present invention relates to a water soluble polymer, a method of producing it, and an application thereof. More preferably, the present invention relates to: a water soluble polymer used in different applications such as detergent additive, scale inhibitor, dispersant for different inorganic or organic substances, thickener, cohesive agent, adhesive agent, surface coating agent, crosslinking agent, humectant; a method of producing this; a detergent additive using the water soluble polymer; and a detergent that uses the detergent additive.

BACKGROUND OF THE INVENTION Water-soluble polymers have been widely used in different applications such as detergent additive, scale inhibitor, dispersant for different inorganic or organic substances, thickener, cohesive agent, adhesive agent, surface coating agent, crosslinking agent. , moisturizer. As such water-soluble polymers, the polymers produced by polymerizing an unsaturated carboxylic acid monomer such as an acrylic acid or Ref .: 186782 copolymers of an unsaturated carboxylic acid monomer with another monomer, and grafted polymers produced by a graft polymerization of a polyether compound with an unsaturated carboxylic acid monomer such as acrylic acid, vinyl acetate, or (meth) acrylic acid ester , it has been widely used conventionally. In addition, this grafted polymer is improved and it has recently been proved that N-vinylpyrrolidone is used. As conventional water-soluble polymers, a grafted polymer obtained by a graft polymerization of a polyether compound with a graft component containing N-vinylpyrrolidone is disclosed as an essential compound such that 1 part by weight of the polyether compound is copolymerizes with 0.1 to 1.2 parts by weight of the graft compound (for example, referring to Japanese Publication of Kokai No. 2001-106743, pages 2, 8 and 9). And the Example discloses a grafted polymer obtained by reacting a polyethylene glycol with a number average molecular weight of 10,000 with an N-pyrrolidone (polyethylene oxide / N-vinylpyrrolidone (weight ratio) = 1 / 0.07 to 0.05) at a temperature of polymerization from 140 to 150 ° C. This grafted polymer has excellent adsorption and dispersion as well as excellent hydrophilicity. This grafted polymer is also preferably used as an inhibitor of scale or additives for detergents. However, this Grafted polymer itself is highly colored. Therefore, this grafted polymer has the opportunity to be improved so that it is preferably used in much more applications by providing it with an excellent capacity for color control and by improving the ability to prevent coloring. Also disclosed is a grafted polymer obtained by a graft polymerization of a polyalkylene oxide with a number average molecular weight of 300 to 100000 with an N-vinylpyrrolidone and at least one species of the vinyl ester derived from an unsaturated monocarboxylic acid containing from 1 to 6 carbon atoms and / or a methyl ester or an ethyl ester of an acrylic acid or a methacrylic acid with a weight ratio of polyalkylene oxide: N-vinylpyrrolidone: the vinyl ester and / or the methyl ester or ethyl ester = 1: 0.3: 1 to 1: 5: 30 (for example, referring to Japanese Patent No. 2541617, pages 1, 4 and 5). And the Example discloses a grafted polymer obtained by reacting a polyethylene oxide with a number average molecular weight of 6000 to 35000 with an N-vinylpyrrolidone (polyethylene oxide / N-vinylpyrrolidone (weight ratio = 1 / 0.5 to 4) using benzoyl peroxide as an initiator, at a polymerization temperature of 105 ° C. However, this grafted polymer has the following problems: Benzoyl peroxide is in a solid state at ordinary temperatures, and therefore the polymerization method is limited to, for example, if the peroxide Benzoyl is dissolved in a solvent and then dropwise, or the benzoyl peroxide is added in one step. In addition, the residual amount of N-vinylpyrrolidone having high toxicity tends to be higher. Therefore, this grafted polymer has the opportunity to improve in the following points. The graft polymerization is carried out simply and efficiently, and the grafted polymer is efficiently provided with a new dirt deposition capability satisfactorily to prevent the new deposition caused by hydrophobic soils, and therefore this grafted polymer is preferably used, for example , as an additive for detergents. A grafted polymer is disclosed which contains: a graft base of a polymer that does not have monoethylenically unsaturated units; and a side chain of a polymer of an N-vinylpyrrolidone or a copolymer of an N-vinylpyrrolidone and N-vinylimidazole, the ratio of the side chain in the total polymer is specified in 35% by weight or more (eg, the patent Japanese Kohyo No. 2005-509063, pages 2, 18 and 19, Japanese Patent Kohyo No. 2005-509064, pages 2, 14 and 15, and Japanese Patent Kohyo No. 2005-509065, pages 2, 18 to 21) . And the Example discloses a technique wherein a polyethylene glycol is reacted with an N-vinylpyrrolidone or an N-vinylimidazole using t-butylpivalate or t-butyl hydroperoxide as an initiator in the presence of an aqueous solvent with a polymerization temperature of 80 to 110 ° C. However, in this technique, the efficiency of the grafting of the monomer component is insufficient, and the N-vinylpyrrolidone decomposes to generate a greater amount of 2-pyrrolidone. Also, a greater amount of N-vinylpyrrolidone tends to remain readily after the polymerization because a greater amount of the N-vinylpyrrolidone is grafted. Therefore, a post-treatment step is needed for the treatment of the residual N-vinylpyrrolidone which has high toxicity and therefore the reaction may take a greater part of time. Therefore, this grafted polymer has the option to improve at these points.

BRIEF DESCRIPTION OF THE INVENTION The present invention has been made in view of the state of the art mentioned above. The present invention has the aim of providing: a water soluble polymer having excellent adsorption, dispersion, and safety as well as excellent hydrophilicity and is capable of sufficiently preventing coloring and which is preferably used in an application as an additive for detergents, for example; an application of this; A production method of the water soluble polymer, the production method is capable of producing a water soluble polymer efficiently in a short time. The current inventors have made different Investigations about water-soluble polymers. They have noted that if a water-soluble polymer is produced by polymerizing a polyether compound with a monomer compound containing an N-vinylpyrrolidone, this water-soluble polymer has excellent adsorption or dispersion due to the presence of the pyrrolidone group in the polymer. They have found that if the amount of N-vinylpyrrolidone used is specified in a certain amount, the polymer obtained is excellent in safety and less colored. They have also found that if a water-soluble polymer is used in, for example, an application as a detergent additive, this detergent additive can prevent re-deposition caused by hydrophobic soils and therefore exhibit high detergency. Therefore, they have solved the problems mentioned above. As mentioned above, the polymer referred to above is produced using a small amount of N-vinylpyrrolidone. This water-soluble polymer can be used particularly and preferably as an application as an additive for detergents because a water-soluble polymer can dramatically exhibit excellent detergency even in small amounts. It has been found that if a water-soluble polymer is produced by polymerizing a polyether compound with a monomer compound containing an N-vinylpyrrolidone using an initiator containing an aliphatic organic peroxide at 120 to 140 ° C, the polymerization can be develop efficiently in a short time, and the residual amount of N-vinylpyrrolidone in the polymer obtained can be sufficiently reduced and a polymer with excellent ability to prevent staining or the ability of a new deposition of dirt to prevent the new deposition caused by the hydrophobic dirt. Therefore, the present invention has been completed. Conventional polymers are not economically preferred because a large amount of N-vinylpyrrolidone, which is high in price, is polymerized. However, the present invention provides a water soluble polymer capable of exhibiting developments as an additive for detergents and the like, even in small amounts of a high-priced N-vinylpyrrolidone. That is, the present invention is a water soluble polymer produced by a polymerization of a polyether compound (A) with a monomer compound containing an N-vinylpyrrolidone (B), wherein the N-vinylpyrrolidone (B) is 0.01. to 0.3 parts by weight to 1 part by weight of the polyether compound (A). The present invention is also a detergent additive containing the water soluble polymer. The present invention is also a detergent that contains a detergent additive.

DETAILED DESCRIPTION OF THE INVENTION The present invention is described in more detail below. The water-soluble polymer of the present invention is produced by polymerizing one or more species of polyester compound (s) (A) (A) with a monomer compound containing an N-vinylpyrrolidone (B). A graft polymerization of a polyether compound (A) with a monomer compound containing an N-vinylpyrrolidone (B) is particularly preferred as a polymerization form, as mentioned below. The preferred embodiment of the present invention includes an embodiment wherein the water-soluble polymer mentioned previously is a water-soluble grafted polymer. The polyether compound (A) in the water-soluble polymer is preferably produced by polymerizing an alkylene oxide containing ethylene oxide. Therefore, the water soluble polymer can retain excellent hydrophilicity and exhibit sufficient dispersibility. Therefore, if a water-soluble polymer is used in an additive application for detergents, the deposition of dirt on clothing and the like is prevented sufficiently, resulting in improvement in detergency. The aforementioned polyether compound (A) is preferably produced by further polymerizing an alkylene oxide with a primary alcohol and / or a secondary alcohol.

Therefore, if a water-soluble polymer is used in, for example, an application as a detergent additive, the detergency can be further improved. The additionally polymerized alkylene oxide preferably contains an ethylene oxide, as already mentioned. The content of the ethylene oxide in the alkylene oxide used to produce the aforementioned polyether compound (A) is preferably at least 50 mol%, relative to 100 mol% of all the alkylene oxides. This is preferably that the aforementioned polyether compound (A) is produced by polymerizing an alkylene oxide containing at least 50 mol% ethylene oxide. If the content of the ethylene oxide is less than 50 mol%, the water soluble polymer obtained can exhibit sufficient hydrophilicity and dispersion. The content thereof is more preferably 70 mol% or more, and even more preferably 80 mol% or greater. The alkylene oxide mentioned above contains an alkylene oxide instead of ethylene oxide, if necessary. Such alkylene oxide is not particularly limited as long as it is copolymerizable with the ethylene oxide. Examples of an alkylene oxide include propylene oxide, n-butylene oxide, isobutylene oxide, styrene oxide, epichlorohydrin, allyl glycidyl ether, and phenyl glycidyl ether. One or two or more species of these can be used. It is also preferred that the polyether compound (A) mentioned above has a number average molecular weight of 400 to 5000. By this, the polymerization can be efficiently and easily developed, and the obtained water-soluble polymer can exhibit sufficient dispersion. If the number average molecular weight is less than 400, the water soluble polymer obtained has an insufficient molecular weight, possibly fails to exhibit excellent dispersion. If the number average molecular weight is greater than 5000, sufficient uniform stirring during the polymerization can not be developed when the polymerization proceeds without a solvent. More preferably, the lower limit of the number average molecular weight is 600 and the upper limit of this is 4000. Even more preferably, the lower limit of this is 800 and the upper limit thereof is 3500. The number average molecular weight mentioned above, for example, gel permeation chromatography (GPC) can be determined under the following conditions, on an equivalent basis of polyethylene glycol. < Measurement conditions of the average molecular weight in number of GPC analysis) > Device: L-7000 series, produced by Hitachi, Ltd. Detection element: Rl Column: produced by Showa Denko K.K. SHODEX Asahipak GF-310-HQ, GF-710-HQ, GF-1G 7B Column temperature: 40 ° C Flow rate: 0.5 ml / min Calibration curve: product of GL Science Inc., polyethylene oxide Eluent: 0.1 sodium acetate / acetonitrile = 3/1 (weight ratio). A more preferred embodiment of the aforementioned polyether compound (A) is an embodiment wherein the polyether compound (A) is produced by polymerizing an alkylene oxide containing at least 50 mol% ethylene oxide and the compound (A) of polyether has a number average molecular weight of 400 to 5000. A method for producing the aforementioned polyether compound (A) is not spatially limited. For example, the polyether compound (A) can be produced by polymerizing the aforementioned alkylene oxide compound in the presence of a reacted compound that serves as the raw material of the polymerization using a conventional method. The aforementioned reacting compound is not especially limited so long as it is a compound that serves as a polymerization raw material of the cyclic ether. The water, alcohols, hydrogen halides, ammonia, amines, hydroxyamines, and carboxylic acids may be mentioned as the aforementioned reacted compound, for example.

Among these, water, alcohols, amines are preferably. For example, alcohols preferably include primary aliphatic alcohols containing from 1 to 22 carbon atoms such as methanol, ethanol, n-propanol, and n-butane; aromatic alcohols such as phenol, isopropylphenol, octylphenol, tert-butylphenol, nonylphenol, and naphthol; secondary alcohols containing from 3 to 18 carbon atoms such as alcohols obtained by oxidizing isopropyl alcohol or n-paraffin; tertiary alcohols such as tert-butanol; diols such as ethylene glycol, diethylene glycol, propanediol, butanediol, and propylene glycol; triols such as glycerin and trimethylol propane; and polyols such as sorbitol. Ethylenediamine, polyethyleneimine can be mentioned as amines, for example. These can be solar or in combination of two or more species of these. The polymerization method mentioned above is not particularly limited. For example, the following methods can be appropriately selected: (1) an anionic polymerization method using an alkali metal hydroxide, a strong alkali such as alcoholate, an alkylamine, or the like as a base catalyst; (2) a cationic polymerization method using a halide of a metal or a metalloid, a mineral acid, an acetic acid, or the like as a catalyst; and (3) a coordination polymerization method using a combination of an alkoxide of a metal such as aluminum, iron, zinc, or the like, an alkaline earth compound, a Lewis acid or the like. The polyether compound thus obtained can be used as the polyether compound (A) of the present invention, and can be used in a form derived from the polyether compound. This derivative can be, for example, a crosslinked compound obtained by reaction of a crosslinking agent having a plurality of groups such as the carboxylic group, isocyanate group, amino group, and the halogen group with the polyether compound obtained above. The monomer compound polymerized with the aforementioned polyether compound (A), in the water soluble polymer mentioned above, preferably contains an N-vinylpyrrolidone (B) essentially. By means of this, the obtained water-soluble polymer can be provided with excellent dispersion and adsorption capacity due to the presence of the pyrrolidone group in the obtained water-soluble polymer. If the water-soluble polymer obtained in a detergent additive is used, for example, a detergent additive adsorbs to elute the dye in water from a fiber, and then disperse it, and thereby prevent transfer to other fibers. The amount of the N-vinylpyrrolidone mentioned above (B) used is preferably 0.01 to 0.3 parts by weight, based on 1 part by weight of the polyether compound (A) previously mentioned. If the amount of N-vinylpyrrolidone (B) used above is less than 0.01 parts by weight, the water-soluble polymer obtained can insufficiently inhibit the dispersion and adsorption capacity attributed to the pyrrolidone group. If the amount used thereof is greater than 0.3 parts by weight, a greater amount of N-vinylpyrrolidone can remain or the polymer can be colored easily, and not economically preferable because the N-vinylpyrrolidone is higher in price. More preferably, the lower limit of the amount used is 0.03 parts by weight and the upper limit thereof is 0.27 parts by weight. Even more preferably, the lower limit of this is 0.05 parts by weight and the upper limit thereof is 0.25 parts by weight. The content of N-vinylpyrrolidone (B) in 100% by weight (% mass,% by mass) of all the monomer compounds is preferably 15% by weight or greater, for example. The content thereof is more preferably 25% by weight or greater, and even more preferably 50% by weight or greater. The monomer compound mentioned above may contain another monomer in place of the N-vinylpyrrolidone (B), if necessary. For example, a monoethylenically unsaturated monomer can be mentioned as the other monomer. If this monomer is used in the polymerization, an excellent dispersion capacity can be provided with the soluble polymer in water obtained. The above-mentioned monoethylenically unsaturated monomer can be, for example, an unsaturated carboxylic acid monomer (C) or another monomer mentioned above. One or two or more species of these can be used. More preferably, at least one carboxylic acid monomer (C) is used. The unsaturated carboxylic acid monomer (C) can have a structure which can be the (salt) of the carboxylic acid by hydrolysis. Examples of the unsaturated carboxylic acid monomer mentioned above (C) include (meth) acrylic acid, (meth) methyl acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, alkyl-2-hydroxymethyl acrylate, maleic acid, dimethyl maleate, diethyl maleate, dibutyl maleate, maleic anhydride, fumaric acid, dimethyl fumarate, diethyl fumarate, and dibutyl fumarate. Among these, acrylic acid or ester thereof, maleic acid, and maleic anhydride are preferred. The amount used of the aforementioned unsaturated carboxylic acid monomer (c) is preferably 5 parts by weight or less, relative to 1 part by weight of the N-vinylpyrrolidone (B). If the used amount of the unsaturated carboxylic acid monomer (C) is greater than 5 parts by weight, the amount of the pyrrolidone group present in the water-soluble polymer is insufficient, and by this the water-soluble polymer obtained can exhibit insufficiently the capacity of adsorption or dispersion. The amount used is more preferably 3 parts by weight or less. As already mentioned above, preferred embodiments of the present invention include an embodiment wherein the monomer compound further contains an unsaturated carboxylic acid monomer (C), and the unsaturated carboxylic acid monomer (C) is 5 parts by weight or smaller, relative to 1 part by weight of the N-vinylpyrrolidone (B). If the unsaturated carboxylic acid monomer (C) is used as the monomer compound polymerized with the polyether compound (A), the polyether compound (A) is preferably produced by further polymerizing an alkylene oxide with a primary alcohol and / or a secondary alcohol, as mentioned above. By this, an esterification reaction of the end of the polyether compound (A) with the unsaturated carboxylic acid monomer (C) can be removed during the polymerization. Therefore, the formation of gel during the polymerization or hydrolysis of the ester bond can be prevented when the water-soluble polymer is used as an additive for detergent, which makes it possible to improve the detergency. The other monomer mentioned above is not particularly limited and may be N-vinylacetamides, N-vinylformamides, N-vinylcaprolactams, N-vinylimidazoles, vinylpyridines, alkyl vinyl ethers, and olefins. Also, they can be one or two or more species of the following monomers used as the other monomer mentioned above: monomers containing functional group, for example, monomers containing amide group such as (meth) arylamide and (meth) acryl acetylamide; vinyl esters such as vinyl acetate, vinyl propionate, vinyl propionate, vinyl pivalate, vinyl benzoate, and vinyl cinnamic acid; alkene monomers such as ethylene and propylene; aromatic vinyl monomers such as styrene and styrene sulfonic acid; vinyl monomers containing trialkyloxysilyl such as vinyltrimethoxysilane and vinylethoxysilane; silicon-containing vinyl monomers such as y- (methacryloyloxypropyl) trimethoxysilane; maleimide derivatives such as maleimide, methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, phenylmaleimide, and cyclohexylmaleimide, vinyl monomers containing nitrile group such as (meth) acrylonitrile; vinyl monomers containing aldehyde group such as (meth) acrolein; vinyl monomers containing sulfuric acid group such as (salt) of 2-acrylamide-2-methylpropane sulfonic acid, (salt) of (meth) allylsulfonic acid, (salt) of vinyl sulfonic acid, (salt) of styrene sulfonic acid , (salt) of 2-hydroxy-3-butenesulfonic acid, and sulfoethyl (meth) acrylate compounds; (meth) hydroxyalkyl acrylate such as hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate; alkyl vinyl ethers such as methyl vinyl ether and ethyl vinyl ether; vinyl chloride, vinylidene chloride, allyl chloride, and aryl alcohol; 3-methyl-3-buten-1-ol; 3-methyl-2-buten-l-ol; polyalkylene oxide adducts of 2-methyl-3-buten-2-ol; and alcohols of these; 3- (meth) acryloxy-1,2-dihydroxypropane; 3- (meth) acryloxy-1,2-di (poly) oxyethylene ether propane; 3- (meth) acryloxy-1,2-dihydroxypropane; 3- (meth) acryloxy-1,2-di (poly) oxypropylene ether propane; 3- (meth) acryloxy-1,2-dihydroxypropane phosphate; and monovalent metallic salts thereof, bivalent metal salts thereof, ammonium salts thereof, organic amine salts thereof, or monoesters or diesters of an alkyl group containing from 1 to 4 carbon atoms; 3- (meth) acryloxy-2-hydroxypropanesulfonic sulphonic acid and monovalent metal salts thereof, divalent metal salts thereof, ammonium salts thereof, organic amine salts thereof, or esters of an alkyl group containing to 4 carbon atoms; 3- (meth) acryloxy-2- (poly) oxyethylene propane sulphonic acid and monovalent metal salts thereof, divalent metal salts thereof, ammonium salts thereof, organic amine salts thereof, or esters of an alkyl group which contains from 1 to 4 carbon atoms; 3- (meth) acryloyl-i-2- (poly) oxyethylene propane sulphonic acid and monovalent metal salts thereof, divalent metal salts thereof, ammonium salts thereof, organic amine salts thereof, or esters of a group rent that contains from 1 to 4 carbon atoms; 3-allyloxypropan-1,2-diol phosphate; 3-allyloxypropane-l, 2-diol sulfonate; 3-allyloxypropane-l, 2-diol sulfate; 3-allyloxy-1, 2-di- (poly) oxyethylene ether propane; 3-allyloxy-l, 2-di- (poly) oxyethylene ether propane phosphate; 3-allyloxy-1,2-di- (poly) oxyethylene ether propane propanesulfonate; 3-allyloxy-l, 2-di- (poly) oxypropylene ether propane; 3-allyloxy-l, 2-di- (poly) oxypropylene ether propanphosphate; 3-allyloxy-1,2-di- (poly) oxypropylene ether propanesulfonate; 6-allyloxyhexane-1, 2, 3, 4, 5-pentaol; 6-allyloxyhexan-1, 2, 3, 4, 5-pentaol phosphate; 6-allyloxyhexan-1, 2, 3, 4, 5-pentaol sulfonate; 6-allyloxyhexan-1, 2, 3, 4, 5-penta (poly) oxyethylene ether hexane; 6-allyloxyhexan-1, 2, 3, 5-penta (poly) oxypropylene ether hexane; 3-allyloxy-2-hydroxypropanesulfonic acid and monovalent salts thereof, divalent metal salts thereof, ammonium salts thereof, or organic amine salts thereof, or, phosphate esters or sulfuric esters or these compounds and monovalent metal salts of these, bivalent metallic salts thereof, ammonium salts thereof, or organic amine salts thereof; 3-allyloxy-2- (poly) oxyethylene propane sulphonic acid and monovalent metal salts thereof, divalent metal salts thereof, ammonium salts thereof, or organic amine salts thereof, or, phosphate esters or sulfuric esters or these compounds and monovalent metal salts thereof, divalent metal salts thereof, ammonium salts thereof, or organic amine salts of these; 3-allyloxy-2- (poly) oxypropylene propane sulfonic acid and monovalent metal salts thereof, divalent metal salts thereof, ammonium salts thereof, or organic amine salts thereof, or, phosphate esters or sulfuric esters or these compounds and monovalent metal salts thereof, divalent metal salts thereof, ammonium salts thereof, or organic amine salts thereof. The amount used of the other monomer mentioned above can be appropriately determined depending on the applications or the necessary developments and the like of the obtained water-soluble polymer. It is preferable that the water-soluble polymer of the present invention have a residual amount of N-vinylpyrrolidone of 4000 ppm or less. If the residual amount of N-vinylpyrrolidone is greater than 4000 ppm, the water-soluble polymer obtained may not be excellent in safety, possibly upon failure to be used in different applications. The residual amount is more preferably 2000 ppm or less, and even more preferably 1000 ppm or less, and particularly preferably 500 ppm or less. The above-mentioned residual amount of N-vinylpyrrolidone is a value in the equivalent base of the solid content and can be determined by liquid chromatography under the following conditions. < Method of measuring the residual amount of N-vinylpyrrolidone > Using liquid chromatography Column: produced by Shiseido Co., Ltd. CAPCELL PAC C18 TYPE UG120 5 μm, 1.5 mmF x 250 mm Eluent: Methanol / water = 1/24 (containing 0.4% by weight of the sodium salt of acid 1- heptanesulfonic) Flow rate: 100 μL / min. Column oven: 20 ° C Injection volume: 10 μL UV detection element: 235 nm It is also preferable that the water-soluble polymer has a value ab (degree of yellowing) of 15.0 or less in an aqueous solution with a solids content of 50% by weight.

If the value of b is greater than 15.0, the polymer can be colored easily, possibly fails to be useful in different applications, particularly in an application as a detergent additive. The value b is more preferably 10.0 or less and even more preferably 8.0 or less. The value of b mentioned above can be determined as follows, for example. < Method of measuring the value b > A polymer (or an aqueous polymer solution) is prepared by diluting or concentrating with pure water such that the polymer concentration is 50% by weight. The prepared aqueous solution is subjected to transmission measurement using a SE-2000 calorimetric difference meter produced by Nippon Denshoku Industries Co., Ltd., to determine the value b. The greater the positive number of the b value is displayed, the stronger the yellowing shown by the aqueous solution. The particularly preferable embodiment of the water-soluble polymer mentioned above is one embodiment in which the water-soluble polymer has a residual amount of N-vinylpyrrolidone of 4000 ppm or less, and the water-soluble polymer has a value of b (degree of yellowing) ) of 15.0 or less in an aqueous solution with a solids content of 50% by weight. It is also preferred that the water soluble polymer have a new anti-dirt deposition ratio (capacity of the new anti-dirt deposition) of 73.0% or more. By this, the water soluble polymer may exhibit greater detergency when used in an application as a detergent additive. The ratio of a new anti-dirt deposition is more preferably 75.0% by weight or more, and even more preferably 76.0% by weight or more. The new anti-dirt deposition ratio is an indicator of the performance of preventing the new deposition caused by solid carbon black, and can be determined by the following method, for example. < Method of measuring the ratio of new anti-dirt deposition > (1) 10 sheets of cotton fabric were prepared in 4 cm x 4 cm, product of Testfabrics, Inc., (unbleached cotton 460U, interlaced). Whiteness (z-value) of each clothes was measured as the reflectance used a calorimetric difference meter (produced by Nippon Denshoku Industries Co., Ltd., SE 2000). The average value of the reflectance is defined as AO. When the whiteness was measured, a clothing that will be measured is covered with the remaining 9 sheets of cotton clothing (on the side opposite the measurement side), and on this, 10 sheets of cotton were placed with the clothes (product of the Clearing Science Association Foundation). (2) Pure water was added to 2.21 g of calcium chloride dihydrate to prepare 15 kg of hard water. Then, this hard water was loaded in an incubator at 25 ° C. (3) A targo meter was set at 25 ° C, and the water lasted 500 ml, a detergent having the following composition 1.25 g, and 0. 32% by weight of the aqueous solution of a polymer sample (polymer) on the equivalent basis of 5 g solid content, carbon black (product of the Clearing Science Association Foundation) 0.5 g was placed in a container and stirred. stirred at 70 rpm for 1 minute. To this was placed 1 sheet of Cotton clothes and stirred at 70 rpm for 10 minutes. (4) The cotton clothes were extracted with tweezers and the container was washed. The hard water was then kept at 25 ° C and the cotton clothes were put into the container and stirred at 70 rpm for 2 minutes. This operation was performed twice. (5) The cotton clothes are each pressed with a loaded fabric to dry later while wrinkling is smoothed. The whiteness (z-value) of each of the cotton clothes was measured as a reflectance again using the calorimetric difference meter mentioned above. The average of reflectances was defined as Al. (6) The ratio of the new anti-dirt deposition was determined by applying the AO and Al calculated previously by the following formula: Speed of the new anti-dirt deposition (ability of the new anti-dirt deposition) (%) = ( Al) / (A0) x 100. The higher the value is obtained, the ratio of the new anti-dirt deposition is excellent. Table 1 shows the composition of the detergent used mentioned above (3).

[Table 1] The water-soluble polymer of the present invention can be produced by polymerizing the polyether compound (A) with the monomer compound containing the N-vinylpyrrolidone (B) in the presence of a polymerization initiator. A graft polymerization of the polyether compound (A) with the monomer compound containing the N-vinylpyrrolidone (B) is particularly preferred as a form of polymerization. By this, the obtained water-soluble polymer can be further improved the ability of the new anti-dirt deposition. In the polymerization step mentioned above, the method of the polymerization reaction is not necessarily limited. For example, the polymerization reaction can be carried out by conventional polymerization methods such as solution polymerization, emulsion polymerization, suspension polymerization, and precipitation polymerization.

The polyether compound (A) can be charged in one step initially or added sequentially, and preferably charged in an initial step in view of the shortening of the reaction time, improvement in productivity, and the like. The monomer compound such as N-vinylpyrrolidone (B) is preferably added sequentially in view of the reaction control, and the like, but the shape of the addition is not limited thereto, and can be charged in an initial step. The monomer compound such as N-vinylpyrrolidone (B) can be previously diluted with a solvent mentioned above and then added. The polymerization initiator is not particularly limited in the aforementioned polymerization step. The organic peroxide is preferable as the polymerization initiator. Examples of this organic peroxide include ketone peroxides such as methyl ethyl ketone peroxide, cyclohexane peroxide, 3,3,5-trimethylcyclohexanone peroxide, methylcyclohexanone peroxide, methyl acetoacetate peroxide, and acetylacetone peroxide.; hydroperoxides such as tert-butyl hydroperoxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide and 2- (4-methylcyclohexyl) hydroperoxide; dialkyl peroxides such as di-tert-butyl peroxide, tert-butyl cumyl peroxide, dicumyl peroxide, a, a'-bis (ter- butylperoxy) -p-diisopropylbenzene, a, a'-bis (tert-butylperoxy) -p-isopropylhexino, 2,5-dimethyl-2, 5-di- (tert-butylperoxy) hexane) and 2,5-dimethyl-2 , 5-di- (tert-butylperoxy) hexane-3); peroxyesters such as tert-butylperoxyacetate, tert-butyl peroxylaurate, tert-butylperoxybenzoate, di-tert-butylperoxyisophthalate, 2,5-dimethyl-2,5-di (benzoylperoxy) hexane, tert-butylperoxyisopropyl carbonate, tert-butylperoxyisobutyrate, tert-butylperoxypivalate, tert-butylperoxineodecanoate, cumyl peroxydecanoate, tert-butylperoxy-2-ethylhexanoate, tert-butylperoxy-3,5,5-trimethylcyclohexanoate, tert-butylperoxymaleic acid, cumyl peroxyoctoate, tert-hexylperoxypivalate, tert-hexylperoxineohexanoate, and cumyl peroxineohexanoate , peroxycetales such as n-butyl-4,4-bis (tert-butylperoxy) valerate, 2,2-bis (tert-butylperoxy) butane, 1,1-bis (tert-butylperoxy) -3,3,5-trimethylcyclohexane, tibisi-tert-butylperoxy) cydohexane, and 2,2-bis (tert-butylperoxy) octane; diacyl peroxides such as acetyl peroxide, isobutyryl peroxide, octanoyl peroxide, decanoyl peroxide, lauroyl peroxide, 3,3,5-trimethylcyclohexanoyl peroxide, succinic acid peroxide, benzoyl peroxide, 2-4 peroxide dichlorobenzoyl, and m-tolyl peroxide; peroxydicarbonates such as diisopropyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-n-propyl peroxydicarbonate, bis- (4-tert-butylcyclohexyl) peroxydicarbonate, dimyristyl peroxydicarbonate, peroxydicarbonate di-methoxyisopropyl, di (3-methyl-3-methoxybutyl) peroxydicarbonate, and di-allyl peroxydicarbonate; and other organic peroxides such as acetyl cyclohexyl sulfanyl peroxide and tert-butyl peroxyalylcarbonate. These can be simple or in combination of two or more species of these. It is preferred that, among these polymerization initiators, an organic peroxide containing at least one aliphatic group is used in the present invention. By this, the grafting efficiency is sufficiently improved and by means of this the water-soluble polymer mentioned above can be efficiently produced. Among others, di-tert-butyl peroxide, tert-butylperoxy-iso-propyl monocarbonate and / or tert-butyl peroxide benzoate is used particularly preferably in view of the reaction temperature in the polymerization step or in the temperature control during storage. Another polymerization initiator (eg, an organic peroxide containing an aromatic group), a chain transfer agent, or a reducing agent can be used in combination with the aforementioned organic peroxide containing at least one aliphatic group. In this case, the amount used of the other polymerization initiator, the chain transfer agent, or the reducing agent is preferably 300 parts by weight or less, relative to 100. parts by weight of the aforementioned organic peroxide containing at least one aliphatic group. More preferably, the amount used thereof is 100 parts by weight or less. The amount used of the polymerization initiator mentioned above is not particularly limited. For example, 0.1 to 30 parts by weight of the polymerization initiator is preferably used relative to 100 parts by weight of all monomer compounds used in the polymerization. If the amount used is less than 0.1 parts by weight, the degree of polymerization of the polyether compound (A) may be insufficient. If the amount used is greater than 30 parts by weight, such as a production method can be economically inefficient, for example, if an organic peroxide is used as the polymerization initiator. The amount used of the polymerization initiator is more preferably 0.5 to 20 parts by weight. The form of addition of the polymerization initiator mentioned above is not particularly limited. The polymerization initiator can be charged in an initial step, or added drop by drop, or sequentially, for example, in portions. A polymerization initiator is preferred in the liquid state at ordinary temperatures because it can be added dropwise without a solvent and therefore the form of addition is poorly limited. The polymerization initiator can be introduced in a simple manner into a container of reaction, or may be premixed with the polyether compound (A), the monomer compound, the solvent, and the like. A solvent can be used in the polymerization mentioned above. However, water is not preferred because water dissolves N-vinylpyrrolidone to generate 2-pyrrolidone. Like other solvents, a solvent having a constant chain transfer as small as possible is preferable to a solvent of a monomer used as a raw material. Examples of a solvent include alcohols such as isobutyl alcohol, n-butyl alcohol, tert-butyl alcohol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, ethylene glycol monoalkyl ether, and propylene glycol monoalkyl ether; diateles such as ethylene glycol dialkyl ether and propylene glycol dialkyl ether; and acetic acid compounds such as ethyl acetate, propyl acetate, butyl acetate, ethyl acetate of ethylene glycol monoalkyl ether, and acetic ester of propylene glycol monoalkyl ether. These can be used alone or in combination of two or more species of these. The alkyl group in the alcohols mentioned above and dietenes are not especially limited, and may be methyl group, ethyl group, propyl group, and butyl group, for example. The amount of solvent used mentioned above is not particularly limited and preferably 20 parts by weight or less, based on 100 parts by weight of the entire system reaction. If the amount used of this is more than 20 parts by weight, the grafting efficiency of the aforementioned monomer compound may be insufficient. The amount used thereof is more preferably 0 parts by weight. That is, it is more preferably that the polymerization is carried out substantially without solvents. By this, the efficiency of the graft can be dramatically improved, which makes it possible to produce an excellent polymer in different developments. Preferred embodiments of the present invention include a mode wherein the polymerization step proceeds without solvents. The solvent mentioned above can be charged in an initial step or added sequentially. The reaction temperature during the polymerization mentioned above is not particularly limited, and is preferably 120 to 140 ° C. If the reaction temperature is less than 120 ° C, the residual amount of the N-vinylpyrrolidone in the water-soluble polymer obtained can not be reduced more than enough, and therefore an excellent polymer can not be produced in safety. If the reaction temperature is more than 140 ° C, the coloring of the polymer can not be prevented and by means of this a polymer can not preferably be used in an application as a detergent additive. And thermal decomposition of the polyether compound (A) or the water soluble polymer obtained can be generated. The temperature of The reaction is more preferably 125 to 140 ° C, and even more preferably 130 to 140 ° C. The reaction pressure during the polymerization mentioned above is not particularly limited, and the reaction can be carried out under ordinary pressure (atmospheric pressure), reduced pressure, or pressurization. The polymerization preferably takes place under ordinary pressure (atmospheric pressure) because the polymerization can be carried out simply and cheaply. The polymerization mentioned above preferably takes place under an inert gas atmosphere such as nitrogen gas, argon gas, CO 2 gas. However, the condition is not particularly limited to the foregoing. The present invention is also a method of producing a water-soluble polymer produced by a polymerization of a polyether compound (A) with a monomer compound containing an N-vinylpyrrolidone (B), wherein the production method comprises a step of developing the polymerization using, as an initiator, an organic peroxide containing at least one aliphatic group, at 120 to 140 ° C. The polymerization develops at 120 to 140 ° C in a production method. By this, the residual amount of N-vinylpyrrolidone in the obtained water soluble polymer can be reduced sufficiently in a short time. By means of this, an excellent safety polymer can be produced and therefore Both are preferably used in different applications. The use of the organic peroxide containing at least one aliphatic group as an initiator (polymerization initiator) makes it possible to improve the efficiency of the graft sufficiently, for example. In the production method mentioned above, the temperature and the polymerization initiator is specified, as mentioned above. By this, each functional effect attributed to this temperature specification and the polymerization initiator is bonded and by means of this an excellent water soluble polymer can be efficiently produced. Therefore, this production method can be a very useful industrial production method. Preferred embodiments and different conditions in the polymerization step mentioned above are as indicated above. Particularly preferred embodiments include, as mentioned above, an embodiment wherein the di-tert-butyl peroxide, tert-butylperoxy-iso-propyl monocarbonate and / or tert-butylperoxybenzoate is / are useful (as) polymerization initiator and a mode wherein the aforementioned polymerization step is carried out without solvent. One or two or more species of polyether compounds conventionally used can be used as the polyether compound (A) used in the production method mentioned above. The preferred form of these polyether compounds as mentioned before The amount of N-vinylpyrrolidone (B) used in the monomer compound mentioned above is preferably fixed as mentioned above. The monomer compound mentioned above may contain another monomer in place of the N-vinylpyrrolidone (B). Preferred embodiments of the other monomer, the amount used, and the like as mentioned above. As described above, the production method mentioned above is preferred as a production method of the water-soluble polymer mentioned before the present invention. This is the preferred embodiments of the present invention include a production method of the water-soluble polymer mentioned before the present invention, wherein the production method comprises a step of developing the polymerization using, as an initiator, an organic peroxide which contains at least one aliphatic group, at 120 to 140 ° C. The water-soluble polymer of the present invention and the water-soluble polymer produced by the production method of the present invention have excellent adsorption, dispersion, and safety as well as excellent hydrophilicity. And it can be prevented that the water-soluble polymers are colored sufficiently and is excellent in different developments. Therefore, these water soluble polymers can be used in different applications such as additive detergent, scale inhibitor, dispersant of different inorganic or organic substances, thickener, cohesive agent, adhesive agent, surface coating agent, crosslinking agent, and humectant. More specifically, these water soluble polymers can be used in anti-redeposition agents for detergents, dye transfer inhibitor for detergents, detergent former, silica scale inhibitor, dyeing aid, dye fixative agent, foam stabilizer , emulsion stabilizer, ink dispersing agent, water-based ink stabilizer, pigment dispersant for coating materials, thickener for coating materials, thickener for cosmetics, dispersant for cosmetics, binder for cosmetics, moisturizer for cosmetics, dispersant additive of cosmetics, hardening aid, hair spray additive, rinse additive, sun block composition additive, resin filler dispersant, coating agent for gravel paper, surface treatment agent for printing papers by inkjet, dispersant for photosensitic resins is, antistatic agent, humectant, raw material for water-absorbing resins, binder for fertilizers, polymer cross-linking agent, resin compatibility agent, photographic additive, pressure sensitive adhesive, paper adhesive, adhesive for use medical, adhesive for patches, adhesive paste, mud dispersant, heavy metal sweeper, and agent for metal surface treatment. Among these, such as water-soluble polymers are preferably used in a detergent additive. Such as a detergent additive containing the water soluble polymer mentioned above also for the present invention. The aforementioned detergent additive contains the water soluble polymer mentioned before the present invention. The pyrrolidone group and preferably the oxyethylene chain of the water soluble polymer adsorb to flow the dye into the water from a fiber during washing and then disperse it. Therefore, this detergent additive containing the water-soluble polymer can effectively prevent transfer to other fibers and also prevent re-deposition due to sufficient hydrophobic or colored dirt, as mentioned above, and by this exhibit sufficiently high detergency In this detergent additive, the content ratio of the water-soluble polymer of the present invention is preferably from 1 to 100% by weight and more preferably from 20 to 100% by weight in 100% by weight of the solids content of the detergent additive. The detergent additive of the present invention can be mixed in for use in, for example, detergents in household dust, liquid detergents, softening agents, industrial cleaning agents, and fiber treatments. The mixed amount of the detergent additive is such case is not particularly limited. For example, the mixed amount of the detergent additive is preferably set at 0.05 to 20% by weight, and more preferably 0.1 to 10% by weight on 100% by weight of the household powder detergents, liquid detergents, softening agents, cleaning agents industrial, and treatments for fibers. Different mixed substrates such as household powder detergents, liquid detergents, softening agents, industrial cleaning agents, and fiber treatments may contain acrylic acid polymers or acrylic acid / maleic acid copolymers conventionally used as a detergent additive. The aforementioned detergent additive is mixed with a detergent and then used, particularly as a preferable embodiment of the aforementioned detergent additive. By this, the functional effects of the present invention are sufficiently exhibited, that is, a detergent additive can sufficiently prevent transfer, re-deposition due to hydrophobic soil, and coloration, and by means of this exhibits high detergency. As mentioned above, a detergent (detergent composition) contains the detergent additive mentioned above is also part of the present invention. With regard to the ratio of the content of the detergent additive of the present invention to the aforementioned detergent, for example, the content ratio of the water-soluble polymer mentioned above is preferably set at 0.1 to 40% by weight in 100% by weight of the Detergent. If the content ratio of the water-soluble polymer mentioned above is less than 0.1% by weight, the detergent may insufficiently exhibit the development of the detergent. If the content ratio of this is more than 40% by weight, the detergent composition can be economically inefficient. The content ratio is more preferably 0.2 to 30% by weight. The detergent form mentioned above is not particularly limited, and may be in powder or liquid form. The aforementioned detergent contains a surfactant in addition to the aforementioned detergent additive. Examples of this surfactant include anionic surfactants, nonionic surfactants, cationic surfactants, and amphoteric surfactants. One or two or more species of these can be used. Examples of the anionic surfactants mentioned above include alkyl benzene sulphonates, alkyl alkenyl ether sulphates, alkyl or alkenyl sulfates, sulfonates of α-olefins, α-sulfonyl fatty acids or ester salts thereof, alkane sulfonates, salts of saturated or unsaturated fatty acids, alkyl alkenyl ether carboxylates, amino acid surfactants, N-acylamino acid surfactants, and phosphate alkyl or alkenyl or salts thereof. The alkyl group or the alkenyl group of these anionic surfactants may have a branched structure of the alkyl group such as a methyl group. Examples of nonionic surfactants mentioned above include polyoxyalkylene alkyl or alkenyl ethers, polyoxyethylene alkyl phenyl ethers, higher alkanol fatty acid amides or alkylene oxide adducts thereof, sucrose grade acid esters, alkyl glycosides, fatty acid monostearate glycerin, and alkylamine oxides. The alkyl group or the alkenyl group of nonionic surfactant may have a branched structure of the alkyl group such as the methyl group. The quaternary ammonium salts and the like can be mentioned as the cationic surfactants mentioned above. The amphoteric surfactants of the carboxylic or sulfobetaine type can be mentioned as the amphoteric surfactants mentioned above. The ratio of the surfactant content in the aforementioned detergent is preferably from 1 to 70% by weight in 100% by weight for the detergent. If the content relationship is less than 1% by weight, the detergent may exhibit insufficiently developments of the detergent. If the content ratio is more than 60% by weight, the detergent can be economically inefficient. The content ratio is more preferably 15 to 60% by weight. The aforementioned detergent preferably contains a detergent former. The content ratio of the detergent former in this case is preferably 0.1 to 60% by weight in 100% by weight of the detergent, for example, more preferably, the content ratio is 1 to 10% by weight if the detergent of the present invention is supplied in the liquid state, and the content ratio is from 1 to 50% by weight if the detergent of the present invention is supplied in the powder state. The detergent former mentioned above is not particularly limited. Examples of the detergent builder include organic formers such as alkali metal salts, ammonium salts, sutured ammonium polyacetates, carboxylates, polycarboxylates, and polyhydroxy sulfonates; inorganic formers such as silicates, aluminosilicates, borates, and carbonates. One or two or more species of these can be used. Examples of polyacetates or polycarboxylates in the organic formers mentioned above include sodium salts, potassium salts, ammonium salts, substituted ammonium salts of ethylenediaminetetraacetic acids, acids nitrilotriacetic, oxidisuccinic acids, mellitic acids, glycolic acids, benzene polycarboxylic acids and citric acids. Preferred examples of the aforementioned inorganic builder include: sodium salts or potassium salts of carbonic acids, bicarbonic acids, and silicic acids; and aluminosilicates such as zeolites. The aforementioned detergent can conventionally further contain the additives or solvents used such as the dye transformer inhibitor, fluorescent whitening agent, foaming agent, foam inhibitor, anti-corrosive, anti-fouling, dirt suspension, soil release agent, adjuster of pH, fungicide, chelating agents, viscosity modifier, enzyme stabilizer, perfume, fiber softener, peroxide, peroxide stabilizer, fluorescent agent, coloring agent, foam stabilizer, polishing agent, bleaching agent and dye. One or two or more species of these may be contained. The content can be determined appropriately depending on the need for development and the like. The water-soluble polymer of the present invention has the aforesaid configuration, and therefore has excellent absorption, dispersion and safety capacity as well as excellent hydrophilicity. Also, the water-soluble polymer can sufficiently prevent coloration.

Therefore, the water soluble polymer can be preferably used in different applications as well as in detergent additives; dispersants of different inorganic or organic substances; inhibitors of incrustation. Particularly if the water-soluble polymer is used in a detergent additive application, the detergent additive can sufficiently prevent transfer, re-deposition due to hydrophobic dirt, coloration and the like and by this exhibit high detergency.

BEST METHODS FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be written in more detail with reference to the Examples, but the present invention is not limited to these examples. Example 1 In a polymerization vessel equipped with a condenser, a nitrogen inlet line, and a thermometer were added 400 parts by weight of polyethylene glycol (product of Wako Pure Chemical Industries, Ltd.) with a number average molecular weight of 1000. The interior of the polymerization vessel was prepared to be a nitrogen atmosphere with the introduction of nitrogen. The polymerization vessel was heated in an oil bath until the temperature inside the polymerization vessel reached 135 ° C. Under agitation, 100 parts by weight of N-vinylpyrrolidone and 5 parts by weight of di-t-butyl peroxide (product of Kayaku Akuzo Corp., registered name "Kayabutil D") each was added dropwise continuously for 1 hour. Then, the stirring was maintained for another hour under heating at 135 ° C to obtain a polymer 1. The residual amount of the n-vinylpyrrolidone of the obtained polymer, value b, and the ratio of the new deposition were measured by the methods mentioned above. . Table 2 shows the results.

Example 2 A polymer 2 was obtained in the same manner as in Example 1, except that polyethylene glycol (product of Wako Pure Chemical Industries, Ltd.) with a number average molecular weight of 1000. In the obtained polymer 2, its residual amount of N-vinylpyrrolidone, the value b, and the ratio of new anti-dirt deposition by means of the methods described above. Table 2 shows the results.

Example 3 A polymer 3 was obtained in the same manner as in Example 1, except that the secondary dodecanol to which the ethylene oxide was added was used in place of the polyethylene glycol (product of Wako Pure Chemical Industries, Ltd.) with a number-average molecular weight of 1000. In the polymer obtained 3 their residual amount of N-vinylpyrrolidone, the value b, and the ratio of new anti-dirt deposition were measured by means of the methods described above. Table 2 shows the results.

Example 4 In a polymerization vessel equipped with a condenser, a line for nitrogen inlet, and a thermometer were added 400 parts by weight of polyethylene glycol (product of Wako Puré Chemical Industries, Ltd.) with a number-average molecular weight of 3000 and 100 parts by weight of N-vinylpyrrolidone). The interior of the polymerization vessel was made to be a nitrogen atmosphere with the introduction of nitrogen. The polymerization vessel heated in an oil bath until the temperature inside the polymerization vessel reached 135 ° C. Under stirring, 2.25 parts by weight of di-t-butyl peroxide (product of Kayaku Akuzo Corp., registered trademark "Kayabutyl D") were added. The stirring was then maintained for another hour under heating at 1352C to obtain a polymer 4. In the polymer 4 obtained its residual amount of the N-vinylpyrrolidone, the value b, and the ratio of new anti-dirt deposition were measured by means of the methods described previously. Table 2 shows the results.

Example 5 In a polymerization vessel equipped with a condenser, a line for nitrogen inlet, and a thermometer was added 315 parts by weight of secondary dodecanol to which 50 moles of ethylene oxide were added. The interior of the polymerization vessel was made to be a nitrogen atmosphere with the introduction of nitrogen. The polymerization vessel was heated in an oil bath until the temperature inside the polymerization vessel reached 135 ° C. Under stirring, 35 parts by weight of N-vinylpyrrolidone and 1.75 parts by weight of di-t-butyl peroxide (product of Kayaku Akuzo Corp., registered trademark "Kayabutyl D") were added, which were added dropwise continuously during 1 hour. The stirring was then maintained for another hour under heating at 135 aC to obtain a polymer 5. In the polymer 5 obtained, its residual amount of N-vinylpyrrolidone, the value b, and the ratio of new anti-dirt deposition were measured by means of of the methods described above. Table 2 shows the results. Comparative Example 1 In a polymerization vessel equipped with a condenser, a line for nitrogen inlet, and a In the thermometer, 400 parts by weight of secondary dodecanol were added to which 50 moles of ethylene oxide were added. The interior of the polymerization vessel was made to be a nitrogen atmosphere with the introduction of nitrogen. The polymerization vessel was heated in an oil bath until the temperature inside the polymerization vessel reached 1052C. Under stirring, 100 parts by weight of N-vinylpyrrolidone and 5 parts by weight of di-t-butyl peroxide (product of Kayaku Akuzo Corp., registered trademark "Kayabutyl D") were added, which were added dropwise continuously during 1 hour. The stirring was then maintained for another hour under heating at 105 ° C to obtain a polymer 6. In the obtained polymer 6, the residual amount of the N-vinylpyrrolidone, the value b, and the new anti-dirt deposition ratio were measured by means of the methods described above. Table 3 shows the results.

Comparative Example 2 A polymer 7 was obtained in the same way as in the Comparative Example 1, except that the reaction temperature was 1502C. In the polymer 7 obtained, its residual amount of N-vinylpyrrolidone, the value b, and the ratio of new anti-dirt deposition were measured by means of the methods described. previously. Table 3 shows the results.

Comparative Example 3 In a polymerization vessel equipped with a condenser, a line for nitrogen inlet, and a thermometer were added 400 parts by weight of polyethylene glycol (product of Wako Puré Chemical Industries, Ltd.) with an average number-average molecular weight. of 3000, 100 parts by weight of N-vinylpyrrolidone, 2.25 parts by weight of benzoyl peroxide (product of Wako Puré Chemical Industries, Ltd.). The interior of the polymerization vessel was made to be a nitrogen atmosphere with the introduction of nitrogen. The polymerization vessel was heated in an oil bath until the temperature inside the polymerization vessel reached 105 aC. The stirring was then maintained for another hour to obtain a polymer 8. In the obtained polymer 8, the residual amount of the N-vinylpyrrolidone, the value b, and the new anti-dirt deposition ratio were measured by the methods described above. . Table 3 shows the results.

Table 2 Table 3 The descriptions in Tables 2 and 3 are as follows. "PEG1000 (or 3000)": polyethylene glycol with a number average molecular weight of 1000 (or 3000) secondary dodecanol adduct EO 50 mol "secondary dodecanol where 50 moles of ethylene oxide" N-VP "are added: N- vinylpyrrolidone "DTBP": di-t-butyl peroxide "BPO": dibenzoyl peroxide Industrial Application The water soluble polymer of the present invention has the aforementioned configuration, and therefore has excellent absorption, dispersion and safety capacity as well as excellent hydrophobicity. Also, the water-soluble polymer can sufficiently prevent coloration. Therefore, the water soluble polymer can be preferably used in different applications as well as as detergent additives; dispersants for different inorganic or organic substances; scale inhibitors. Particularly, if the water-soluble polymer is used in an additive application for detergent the detergent additive can sufficiently prevent transfer, re-deposition due to hydrophobic soil staining and the like, and by this exhibit high detergency.

The present application claims priority to Japanese Patent Application No. 2005-165997 filed in Japan on June 6, 2005, entitled "WATER-SOLUBLE POLYMER, PRODUCTION METHOD THEREOF AND APPLICATION THEREOF", all the contents of which are incorporated in the present as a reference. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (9)

CLAIMS Having described the invention as above, the content of the following claims is claimed as property:

1. Water-soluble polymer produced by a polymerization of a polyether compound with a monomer compound containing an N-vinylpyrrolidone, characterized in that the N-vinylpyrrolidone is from 0.01 to 0.3 parts by weight of the polyether compound.

2. A water-soluble polymer according to claim 1, characterized in that it has a residual amount of N-vinylpyrrolidone of 4000 ppm or less, and the water-soluble polymer has a value b (degree of yellowing) of 15.0 or less in an aqueous solution with a solids content of 50% by weight. Water-soluble polymer according to claim 1 or 2, characterized in that the polyether compound is produced by polymerizing an alkylene oxide containing at least 50 mol% of ethylene oxide, and the polyether compound has a molecular weight number average of 400 to 5000. 4. Water-soluble polymer according to any of claims 1 to 3, characterized in that the monomer compound further contains an unsaturated carboxylic acid monomer, and the unsaturated carboxylic acid monomer is parts by weight or less, in relation to 1 part by weight of N-vinylpyrrolidone. 5. Water-soluble polymer according to any of claims 1 to 4, characterized in that the polyether compound is produced by further polymerizing an alkylene oxide with a primary alcohol and / or an alcohol. 6. Water-soluble polymer according to any of claims 1 to 5, characterized in that it has a new anti-dirt deposition ratio of 73.0% or more. 7. Method of producing a water-soluble polymer produced by a polymerization of a polyether compound with a monomer compound containing an N-vinylpyrrolidone, characterized in that it comprises a step of developing the polymerization using, as an initiator, an organic peroxide which contains at least one aliphatic group at 120aC at 140aC. 8. Additive for detergent, characterized in that it contains the water-soluble polymer according to claim 1 to 6. 9. Detergent, characterized in that it contains the detergent additive according to claim 8.