WO1993021237A1 - Crosslinked hydrophilic resins and method of preparation - Google Patents
Crosslinked hydrophilic resins and method of preparation Download PDFInfo
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- WO1993021237A1 WO1993021237A1 PCT/US1993/003489 US9303489W WO9321237A1 WO 1993021237 A1 WO1993021237 A1 WO 1993021237A1 US 9303489 W US9303489 W US 9303489W WO 9321237 A1 WO9321237 A1 WO 9321237A1
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- hydrophilic resin
- crosslinked
- crosslinked hydrophilic
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
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- 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
- C08F20/00—Homopolymers and 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
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
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- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
Definitions
- This invention relates to crosslinked hydrophilic resins, methods for preparing crosslinked hydrophilic resins and absorbent structures incorporating the crosslinked hydrophilic resins.
- Hydrophilic resins are primarily used in personal care products which absorb body fluids, for example baby diapers, adult incontinence products and feminine hygiene products.
- hydrophilic resin particles are incorporated into absorbent structures which contain for example, synthetic and natural fiber or paper based woven and non-woven structures, and toughened masses of fibers, such as fluff pads.
- the materials used in such structures can instantaneously absorb aqueous fluids and distribute them over the whole absorbent structure.
- the structures in the absence of hydrophilic resin particles, have limited absorption capacity, and are bulky due to the large amount of material needed to provide acceptable absorption capacity and do not retain fluid under pressure.
- a means for improving the absorbency and fluid retention characteristics of such absorbent structures is to incorporate hydrophilic resin particles which imbibe fluids to form a swollen hydrogel material, see U.S. Patent 4,610,678.
- the hydrophilic resin particles quickly absorb fluids and retain such fluids to prevent leakage and give the absorbent structure a "dry feel" even when wetted.
- the fraction of water-soluble polymer present in the resin is generally increased.
- the gel strength of the swollen gel its absorption capacity under pressure and absorption speed are reduced.
- the water absorbent resin tends to agglomerate upon wetting which results in a reduction of its absorption capacity and in gel blockage which prevents transport of fluids within the absorbent structure. This is a particular problem when a large fraction of the absorbent structure is replaced with hydrophilic resin particles to prepare a thin absorbent device.
- One method of improving the absorption characteristics is to incorporate a compound which crosslinks the final product into the monomer mixture used to prepare the hydrophilic resin.
- Brandt U.S. Patent 4,654,039 discloses the preparation of hydrophilic resins and known crosslinking agents for such resins, Column 6 line 34 to Column 7, line 16.
- Parks U.S. Patent 4,295,987 discloses the use of ethylene glycol diacrylate, tetraethyleneglycol diacrylate and methylene-bis- acrylamide as crosslinking agents for polyacrylate based hydrophilic resins.
- Japanese patent 55-82104 discloses the use of ethylene glycol di(meth)acrylate, trimethylol propane tri(meth)acrylate and propylene glycol di(meth)acrylate as crosslinking agents for polyacrylate based hydrophilic resins.
- Masuda et al. U.S. Patent 4,076,663 discloses a water absorbent resin is produced by polymerizing (A) starch or cellulose, (B) at least one monomer having a polymerizable double bond which is water-soluble or becomes water-soluble by hydrolysis and (C) a crosslinking agent, and subjecting, if necessary, the resulting product to hydrolysis.
- di- or poly-esters of unsaturated mono- or poly-carboxylic acids with polyols such as di- or tri-(meth) crylic acid esters of polyols (such as ethylene glycol, trimethylol propane, glycerine, polyoxyethylene glycols and polyoxypropylene glycols.
- Extractable materials are water-soluble oligomers or non-crossiinked polymers which can be extracted from the hydrophilic resins when exposed to aqueous fluids. The presence of extractable materials reduces the efficacy of the water absorbent particles.
- crosslinkers are not water- -soluble and require the presence of surfactants or dispersants to solubilize or disperse them so they can be present in the reaction medium to crosslink the hydrophilic resins.
- the presence of such dispersants and surfactants often adversely af ect the absorbent properties of the hydrophilic resins.
- hydrophilic resins which have high absorption capacity, low extractable materials and high toughness or gel modulus. What is further needed is a process for the preparation of such resins. What are needed are crosslinking agents which are water- -soluble.
- the properties desired in hydrophilic resin vary depending upon the application and the desired effect of the resins. Thus, what are needed are processes which are flexible in preparing hydrophilic resins with varied properties such as absorption capacity and absorption under load.
- the invention comprises a carboxyl containing hydrophilic resin crosslinked by one or more compounds corresponding to Formula 1 c R 1 -(0(CH(R3)CH(R3)0) -C(0)-R 2 ) Y Formula 1
- R is independently in each occurrence a polyvalent
- R is independently in each occurrence a C2_IQ straight- or branched-
- R is independently in each occurrence a hydrogen or methyl; x is independently in each occurrence a number of 2 or greater; where x is 2, y is independently in each occurrence a number of 3 to 8; and where x is 3 or greater, y is independently a number of 2 to 7.
- the invention is a process for the preparation of crosslinked hydrophilic resins which comprises A) contacting i) one or more ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acid anhydrides or salts thereof and optionally ii) one or more comonomers of an acrylamide, a vinyl
- the properties of the crosslinked hydrophilic resin may be further enhanced or improved by heating the crosslinked hydrophilic resin under conditions such that the crosslinked hydrophilic resin exhibits a Centrifuge Capacity (CC) of 25 g/g or
- the invention is a water-absorbent
- Figure 1 is a plot of the ratio of the percentage of extractable materials to centrifuge capacity against the centrifuge capacity of crosslinked resins having varied amounts of ethylene oxide in the backbone of the crosslinker.
- Figure 2 plots both the ratio of centrifuge capacity after postheating (CC(T)) to centrifuge capacity before heating (CC(o)) and absorption under load after postheating against the number of moles of ethylene oxide in the backbone of the crosslinker.
- Figure 3 is a plot of the ratio of centrifuge capacity after postheating to centrifuge capacity before postheating versus postheat temperature.
- Figure 4 shows a plot of the ratio of absorption under load after postheating to absorption under load before postheating against post heat temperature.
- Figure 5 plots the absorption under load against centrifuge capacity at various post heat temperatures.
- Figure 6 plots the ratio of absorption under load to centrifuge capacity against centrifuge capacity at each post heat temperature.
- Figure 7 plots the level of extractable materials present at each post heat temperature against centrifuge capacity.
- Figure 8 plots the ratio of extractables to centrifuge capacity against centrifuge capacity at each post heat temperature.
- Figure 9 plots the absorption under load against time for a resin of the invention and a comparative resin.
- Figure 10 plots the ratio of the absorption under load at various times to final absorption under load (60 minutes) against time for two resins, one of the invention and one comparative.
- Figure 11 is the plot of absorption under load versus time for two resins, one of the invention and one comparative resin.
- Figure 12 plots the ratio of absorption under load at various times over absorption under load at a final time of 60 minutes against time.
- Figure 13 plots absorption under load at varying load levels of 0 to 1.0 psi (70.31 gm/cm2) for a resin of the invention and a comparative resin.
- the hydrophilic resins of this invention demonstrate high absorption capacities while having low extractable material fractions and a high absorbent gel particle toughness.
- the crosslinkers corresponding to Formula 1 are water-soluble or self-dispersible in water and thus no additional surfactants or dispersants are required.
- the optional postheating step in the process for the preparation of the water-absorbent resin particles allows variation of the process to achieve a desired mix of properties, that is absorption under load, absorption capacity and percent of extractable materials.
- the crosslinked hydrophilic resins of this invention are polymers derived from one or more ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acid anhydrides or salts thereof. Additionally the polymers may include comonomers commonly known in the art for use in absorbent resins or for grafting onto absorbent resins such as an acrylamide, an acrylonitrile, a vinyl pyrrolidone, a vinyl sulphonic acid, a cellulosic monomer, a modified cellulosic monomer, a polyvinyl alcohol or a starch hydrolyzate.
- Olefinically unsaturated carboxylic acid and carboxylic acid anhydride monomers include the acrylic acids typified by acrylic acid, methacrylic acid, ethacrylic acid, alpha-chloroacrylic acid, alpha-cyano acrylic acid, beta-methyl-acrylic acid (crotonic acid), alpha phenyl acrylic acid, beta-acryloxy propionic acid, sorbic acid, alpha-chloro sorbic acid, angelic acid, cinnamic acid, p-chloro cinnamic acid, beta-styrl acrylic acid (l-carboxy-4-phenyl butadiene-1,3), itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, aconitic acid, maleic acid, fumaric acid and maleic acid anhydride.
- the starting monomer is acrylic acid, methacrylic acid, or a salt thereof, with acrylic acid or a salt thereof being more preferred.
- the compounds corresponding to Formula 1 generally are C2 _ 10 polyhydric hydrocarbons which have been alkoxylated with between two and eight alkylene oxide units per hydroxyl moiety wherein the terminal hydroxyl moiety of each alkyleneoxide chain is esterified with a C2 ⁇ 10 unsaturated carboxylic acid or ester thereof.
- the starting alcohol is a C3-6 carbon polyhydric compound having from 2 to 4 hydroxyl moieties.
- the starting material is trimethylol propane, glycerol, pentaerythritol, 1,3- ⁇ ropanediol, propylene glycol, 1,4-butanediol, or butylene glycol.
- the starting alcohol is trimethylol propane, glycerol or pentaerythritol with trimethylol propane being most preferred.
- the alkylene oxide chain may be composed of ethylene oxide, propylene oxide or butylene oxide moieties. Such a chain may comprise a single species of an alkylene oxide or a mixture of the alkylene oxide species. If a mixture is used, various alkylene oxides may be arranged in a random pattern or in blocks of each species.
- the alkylene oxide chain is based on ethylene oxide, propylene oxide or a mixture thereof; more preferably it is an ethylene oxide or propylene oxide chain and most preferably an ethylene oxide chain.
- each alkylene oxide chain attached to the hydroxyl moieties of the starting alcohol have from three to seven alkylene oxide units, and most preferably four to six alkylene oxide units.
- the preferred number of alkylene oxide units in each chain is dependent upon the number of chains. As the number of chains (x) increases, the number of alkylene oxide units per chain required for good properties is lower.
- the esterifying agent is a C2 ⁇ 10 straight- or branched-chain ethylenically unsaturated carboxylic acid or ester thereof, preferably a C2 ⁇ ethylenically unsaturated carboxylic acid or ester thereof, even more preferably a C2-3 ethylenically unsaturated carboxylic acid or ester thereof, and most preferably acrylic acid, methacrylic acid or an ester thereof.
- the crosslinkers of this invention are prepared by processes well-known in the art.
- the polyhydric alcohol is reacted with from 2 to 8 alkylene oxide units per hydroxyl moiety so as to prepare a compound with 2 or more chains of hydroxy-terminated polyalkylene oxides.
- the reaction product is reacted with sufficient C2 ⁇ 10 straight- or branched-chained ethylenically unsaturated carboxylic acids, or an ester thereof, to provide a terminal ester containing ethylenically unsaturated moiety for each hydroxyl moiety on the alkylene chain attached to the starting alcohol.
- Such preparation procedures are well known in the art, see March, Advanced Organic Chemistry, 2nd Edition, pp. 361-365.
- crosslinkers described by Formula 1 are found as a mixture of materials described by the formula and by-products resulting from the preparation process.
- Crosslinkers corresponding to Formula 1 are available from Craynor under the trademark Craynor and from Sartomer under the trademark Sartomer.
- Polyvalent as used herein means the moiety has two or more valences by which the moiety is bonded to other moieties.
- R2 is preferably a C2- straight- or branched-chain alkenyl moiety, and most preferably a C2-3 straight- or branched-chain alkenyl moiety.
- each (CH(R3)CH(R3)0)- unit one R3 is methyl and the other is hydrogen. Most preferably each R3 is hydrogen.
- x is from 2 to 4, and even more preferably from 3 to 4.
- y is from 3 to 7 and more preferably 4 to 6.
- the crosslinker is present in sufficient amounts to significantly improve the absorption under load and reduce the percentage of extractable materials contained in the hydrophilic resin while preferably maintaining or increasing the centrifuge capacity.
- the crosslinker is present in an amount of 1,000 parts per million or greater by weight based on the amount of the polymerizable monomer present, more preferably 2,000 parts per million or greater and most preferably 3,500 parts per million or greater.
- the crosslinker is present in an amount of 50,000 parts per million or less by weight based upon the amount of the polymerizable monomer present, more preferably 5,000 parts per million or less and most preferably 8,000 parts per million or less.
- additives which are well-known in the art, such as surfactants, may be incorporated into the monomer mixture.
- the crosslinked hydrophilic resins are prepared by contacting i) one or more of an ethylenically unsaturated carboxylic acid, an ethylenically unsaturated carboxylic acid anhydride or a salt thereof, ii) optionally one or more of an acrylamide, a vinyl pyrrolidone, a vinyl sulphonic acid, an acrylonitrile, a cellulosic monomer, a modified cellulosic monomer, a polyvinyl alcohol monomer, or a starch hydrolyzate monomer with iii) a crosslinking compound which corresponds to Formula 1 in an aqueous medium, optionally in the presence of a free radical or oxidation reduction (redox) catalyst system under conditions such that a crosslinked hydrophilic resin is prepared.
- aqueous medium means water, or water in admixture with a water miscible solvent.
- Preferred water miscible solvents include lower alcohols and alkylene glycols.
- the monomers and crosslinkers are preferably dissolved, dispersed or suspended in the aqueous medium at a concentration level of 15 percent by weight or greater, more preferably 25 percent or greater, and most preferably 29 percent or greater.
- the monomers and crosslinkers are preferably dissolved, dispersed or suspended in the aqueous medium at a concentration level of 50 percent by weight or less and more preferably 40 percent or less.
- An optional component in the aqueous medium is a conventional water-soluble polymerization initiator material including peroxygen compounds such as sodium, potassium and ammonium persulfates, caprylyl peroxide, benzoyl peroxide, hydrogen peroxide, cumene hydroperoxides, tertiary butyl diperphthalate, tertiary butyl perbenzoate, sodium peracetate and sodium percarbonate.
- peroxygen compounds such as sodium, potassium and ammonium persulfates, caprylyl peroxide, benzoyl peroxide, hydrogen peroxide, cumene hydroperoxides, tertiary butyl diperphthalate, tertiary butyl perbenzoate, sodium peracetate and sodium percarbonate.
- the initiator material can comprise up to 5 mole percent based on the polymerizable monomer present. More preferably the initiator comprises from 0.001 to 0.5 mole percent based on the polymerizable monomer.
- the process of the invention may be performed in a batch manner wherein all of the reaction materials are contacted and the reaction proceeds, or it may take place with the continuous addition of one or more of the components over the reaction period.
- the aqueous medium is subjected to polymerization conditions which are sufficient to produce the crosslinked hydrophilic resin of the invention.
- the reaction is performed under an inert gas atmosphere, for example under nitrogen or argon.
- the reaction may be performed at any temperature at which polymerization occurs, preferably 0°C or greater, more preferably 25°C or greater and most preferably 50°C or greater.
- the temperature is 100°C or less, more preferably 80°C or less and most preferably 70°C or less.
- the reaction is exothermic and it may be desirable to provide a means for cooling the reactor so as to maintain a desired temperature.
- the reaction mixture may be reacted for a time sufficient to result in the desired conversion of polymerizable monomer to crosslinked hydrophilic resins.
- the conversion is 95 percent or greater, more preferably 98 percent or greater and most preferably 99 percent or greater.
- the reaction time is 20 minutes or greater, more preferably 1 hour or greater and most preferably 2 hours or greater.
- the reaction time is 6 hours or less, more preferably 4 hours or less and most preferably 3 hours or less.
- 25 mole percent or greater of the carboxylic acid units of the hydrophilic resin are neutralized with base, even more preferably 50 percent or greater and most preferably 65 percent or greater. This neutralization may be performed after completion of the polymerization.
- the starting monomer mix has carboxylic acid moieties which are neutralized to the desired level prior to polymerization.
- the final polymer or the starting monomers may be neutralized by contacting them with a salt forming cation.
- salt forming cations include alkaline metal, ammonium, substituted ammonium and amine based cations.
- the polymer is neutralized with an alkaline metal hydroxide such as sodium hydroxide.
- aqueous reaction mixture as hereinbefore described is suspended in the form of tiny droplets in a matrix of a water-immiscible, inert organic solvent such as cyclohexane.
- hydrogel-forming polymer material recovered from such processes be treated to remove substantially all of the excess organic solvent. It is highly preferred for example, that the hydrogel-forming polymers herein contain no more than 0.5 percent by weight of residual organic solvent.
- the crosslinked hydrophilic resins of the invention generally absorb all of the aqueous reaction medium to form a hydrogel.
- the crosslinked hydrophilic resin is recovered from the reactor in the form of an aqueous hydrogel.
- Hydrogel refers to water swollen crosslinked hydrophilic resin particles. In preferred embodiments such hydrogels comprise 15 percent by weight or greater crosslinked hydrophilic resin, with the remainder comprising water and more preferably comprise 25 percent by weight or greater crosslinked hydrophilic resin.
- the hydrogel comprises 50 percent by weight or less of crosslinked hydrophilic resin, and more typically 45 percent by weight crosslinked hydrophlic resin or less.
- the crosslinked hydrophilic resin hydrogel particles may be recovered from the reaction medium by azeotropic distillation and/or filtration followed by drying. If recovered by filtration then some means of removing the solvents present in the hydrogel must be used. Such means are commonly known in the art.
- the crosslinked hydrophilic resin hydrogel particles may be optionally subjected to an initial mechanical particle size reduction.
- the size of the gel particles after mechanical particle size reduction should be such that homogeneous drying of the particles can occur, with particle sizes of 2 cm or less being preferred.
- This particle size reduction can be performed by any means known in the art which gives the desired result.
- the particle size reduction is performed by chopping the hydrogel.
- the crosslinked hydrophilic resin hydrogel particles are subjected to conditions to remove substantially all of the water nd optional solvent, such that the water-absorbent resin particles can be further processed, packaged, and incorporated into absorbent structures.
- the temperature at which the drying takes place is a temperature high enough such that the water and optional solvent, is removed in a reasonable time period, yet not so high so as to cause degradation of the crosslinked hydrophilic resin, such as by breaking of the crosslink bonds in the resin.
- the temperature of the water absorbent resin particles during drying is 170°C or less.
- the temperature during drying is 100°C or above, and more preferably 150°C or above.
- the drying time should be sufficient to remove substantially all of the water and optional solvent. Substantially all means all water and optional solvent is removed except minor amounts which do not adversely affect the processing of the particles or their function.
- a minimum time for drying is 10 minutes or greater, with 15 minutes or greater being typical.
- the drying time is 60 minutes or less, with 20 minutes or less being more preferred.
- drying is performed under conditions such that water, and optional solvent, volatilizing away from the absorbent resin particles is removed. This can be achieved by the use of vacuum techniques or by passing inert gases or air over or through the layers of crosslinked hydrophilic resin particles.
- the drying occurs in dryers in which heated air is blown through or over layers of the crosslinked hydrophilic resin particles.
- Preferred dryers are fluidized beds or belt dryers.
- a drum dryer may be used.
- the water may be removed by azeotropic distillation, by techniques well- known in the art.
- the crosslinked hydrophilic resin particles may fuse together to form sheets or agglomerates which sheets or agglomerates may then be subjected to mechanical breaking means part-way through the drying process.
- the crosslinked hydrophilic resin particles are then subjected to further mechanical particle reduction means.
- Such means can include chopping, cutting and/or grinding.
- the object is to reduce the particle size of the water-absorbent resin particles to a particle size acceptable in the ultimate end use.
- the absorbent resin particles are chopped and then ground.
- the particle size is preferably 2 mm or less, more preferably 0.8 mm or less.
- the particles have a size of 0.02 mm or greater, more preferably 0.05 mm or greater.
- the crosslinked hydrophilic resin particles may be subjected to surface crosslinking techniques to further strengthen the particles. Such techniques are well-known in the art; see for example GB 2,119,384.
- the crosslinked hydrophilic resins are postheated at temperatures at which the crosslinked hydrophilic resins absorption properties are improved. The time period for exposure to such temperatures is chosen such that the absorption properties of the resin are improved.
- the crosslinked hydrophilic resins are preferably heated to a temperature 170°C or above, most preferably 190°C or above, and most preferably to 210°C or above. Below 170°C no improvement in the absorption properties is seen.
- the temperature should not be so high as to cause the crosslinked hydrophilic resin polymer to degrade.
- the temperature is 250°C or below and most preferably 230°C or below.
- the crosslinked hydrophilic resin is heated to the desired post heat temperature and preferably maintained at such temperature for at least 1 minute heating time and most preferably at least 5 minutes. Below 1 minute no improvement in properties occurs. If the heating time is too long it becomes uneconomical and risk is run that the crosslinked hydrophilic resin may be damaged.
- Preferably crosslinked hydrophilic resin is maintained at the desired temperature for 60 minutes or less, preferably 30 minutes or less. Above 60 minutes no significant improvement in properties is noticed.
- the properties of the crosslinked hydrophilic resin can be adjusted and tailored by adjustment of the temperature and the time of the postheating step.
- the crosslinked hydrophilic resins may be difficult to handle due to the static electricity. It may be desirable to rehumidify the crosslinked hydrophilic resins to reduce or eliminate the effect of the static electricity.
- the surface of the resin particles may be treated with an antistatic agent such as polyethylene glycol or glycerin.
- the dry crosslinked hydrophilic resin is contacted with a sufficient amount of water vapor to reduce or eliminate the effects of the static electricity, yet not so much so as to cause the crosslinked hydrophilic resin to agglomerate.
- the dry crosslinked hydrophilic resin is humidified with 1 percent or more by weight of water and more preferably 5 percent or more by weight of water.
- the dry crosslinked resin is humidified with 10 percent or less by weight of water and more preferably 6 percent or less by weight of water.
- agglomeration prevention or rehydration additives may be added to the crosslinked hydrophilic resin.
- Such additives include surfactants and inert inorganic particles such as silica, see for example U.S. Patent Nos. 4,286,082, 4,734,478 and DE 2706135.
- crosslinked hydrophilic resins with a better balance of properties than previously known crosslinked hydrophilic resins.
- the extractable material level is lower and the absorption under load is higher for the crosslinked hydrophilic resins of the invention when compared to conventional resins.
- the centrifuge capacity is higher than in conventional resins.
- the crosslinked hydrophilic resins of this invention are more efficient than prior art resins. As there is balance between the centrifuge capacity and the amount of extractable materials as against the toughness and absorption under load, it is the objective of this invention to maximize the absorption under load and centrifuge capacity.
- the resins have an absorption under load of 20 g/g or greater, more preferably 25 g/g or greater and most preferably 30 g/g or greater. It is further preferable that the resins have a percent extractable materials level of 17 percent by weight of the particle or less, more preferably 12 percent or less, and most preferably 8 percent or less. It is also preferred that the resins have a centrifuge capacity of 25 g/g or more and more preferably 28 g/g or more.
- the crosslinked hydrophilic resins demonstrate a dry feel when swollen with water, excellent rehydration behavior, that is the ability of a swollen resin to accept additional fluid, distribute it throughout the gel volume and finally absorb it.
- the crosslinked hydrophilic resins also demonstrate low incidence of gel blocking as evidenced by formation of fish eyes and unswollen lumps.
- the crosslinked hydrophilic resins of the invention are used in absorbent structures they provide better performance in terms of dry feel when swollen, fluid retention under pressure and minimization of leaks.
- the load on a hydrophilic resin is increased the absorption capacity decreases.
- the crosslinked hydrophilic resins of the invention demonstrate a lower rate of decrease in absorption capacity as the load on the resin increases.
- the crosslinked hydrophilic resins of this invention can be used in any use wherein absorption and binding of aqueous based fluids is desired.
- the absorbent structure comprises an absorbent support structure and crosslinked hydrophilic resin particles according to the invention.
- the crosslinked hydrophilic resins of this invention are mixed into or attached to a structure of absorbent material such as synthetic or natural fibers or paper based woven or non-woven fibers etc. to form a structure.
- the woven or non-woven structure functions as a mechanism for wicking and transporting via capillary action the fluid to the water-absorbent resin particles which bind and retain such fluids.
- the absorbent structure comprises one or more layer of the crosslinked hydrophilic resins sandwiched between water permeable support layers.
- the crosslinked hydrophilic resins are adhesivized and attached to a support structure as disclosed in Ball WO 91/18092. Examples of such structures are diapers, adult incontinence structures and sanitary napkins. The following examples are included to illustrate the invention, and do not limit the scope of the claims. Unless otherwise stated all parts and percentages are by weight.
- the crosslinked hydrophilic resins are prepared in an apparatus having four 300 mL glass reactors equipped with thermometers. A waterbath with a heater which is capable of holding all four reactors simultaneously is used. The use of four reactors allows four simultaneous runs of different crosslinkers or crosslinker levels.
- the aqueous polymer gel is granulated to particles having a size of between approximately 1 and 5 mm with the aid of a meat mincer (disc holes 5 mm) and a part of it is dried in a hot air stream of 160°C for approximately 20 min.
- the polymer is ground in a knife cutter and sieved.
- the particle size fraction between 0.6 and 0.3 mm (30 to 50 mesh) is used for performance and quality analysis.
- For gel strength measurement the fraction 0.2 mm to 0.3 mm (50 to 80 mesh) is used.
- the 30 to 50 mesh fraction is collected and analyzed for 30 minutes centrifuge capacity (CC), g/g absorption under load (AUL), g/g and 16 hour extractables fraction (EXT %).
- Performance and quality of the crosslinked hydrophilic resins prepared are measured by the following methods. Centrifuged Capacity
- Selected crosslinked water absorbent resins having each of the different crosslinkers tested herein are post heated according to the following procedure. Each post heated resin is tested for centrifuge capacity, absorption under load and extractables. The results are compiled in Table 1.
- Postheat Procedure T e postheating is performed by preheating a zone with a hot air gun. Once the target temperature is reached and stabilized, the sample is placed in the zone, a contact thermometer is placed in contact with the sample. The temperature of the sample is monitored until it stabilizes at the target temperature. The sample is maintained at the target temperature for 20 minutes.
- Table 1 demonstrates the use of CRAYNOR CN 435 (a trimethylol propane polyoxyethylene) triacrylate having 5 ethyleneoxy units per polyethyleneoxy chain is advantageous as regards minimization of extractables at a given absorption capacity. This effect is more apparent for high values of centrifuge capacity, i.e., 40 g/g and over.
- Figure 1 is a plot of the ratio of extractables (percent) to the centrifuge capacity (g/g) vs the centrifuge capacity (g/g) for each of the experiments performed with crosslinked hydrophilic resins, wherein the crosslinkers contain 0, 3 and 15 moles of ethylene oxide residue per mole.
- Figure 1 demonstrates that hydrophilic resins prepared using a crosslinker having 15 moles of ethylene oxide incorporated into each mole of crosslinker demonstrates lower extractable levels at a given centrifuge capacity level than hydrophilic resins using crosslinkers without ethylene oxide or with three moles of ethylene oxide per mole. This demonstrates that the invention allows the preparation of hydrophilic resins with lower extractables without reducing the absorption capacity of the resin.
- Figure 2 is the plot of the ratio of Centrifuge Capacity after postheating (CC(T)) to Centrifuge Capacity before heating (CC(o)) against the number of moles of ethylene oxide in the backbone of the crosslinker.
- Figure 2 demonstrates that with postheating, the balance of properties improves with an increasing number of moles of ethylene oxide and with postheating.
- Examples 21-34 Two sets of samples of crosslinked hydrophilic resin prepared according to the procedure described hereinbefore are subjected to postheating conditions. For one set of samples, the crosslinker is trimethylolpropane triacrylate (no ethylene oxide units) at a level of 2150 ppm, (Resin A).
- the crosslinker is trimethylolpropane polyethyleneoxy triacrylate (5 moles of ethylene oxide units per polyoxyethylene chain) used at a level of 3050 ppm (Resin B).
- a sample of each set is heated for 20 minutes at temperatures ranging from 180°C to 250°C.
- the centrifuge capacity, absorption under load and extractable levels are determined as described previously and compiled in Table 2.
- Ratio of Centrifuge capacity after post heat to centrifuge capacity before post heating CC(o)
- ⁇ Ratio of absorption under load after post heating to absorption under load before post heating AUL(o)
- ⁇ Ratio of extractables after post heating to extractables before post heating EXT(o)
- Figure 3 is a plot of the ratio of CC(T)/CC( ⁇ ) versus temperature from 180°C to 230°C, for Resin A and Resin B.
- CC(T) is the centrifuge capacity after postheating and CC( ⁇ ) is the centrifuge capacity prior to postheating.
- Figure 3 demonstrates that a hydrophilic resin crosslinked with a crosslinker of the invention (15 moles ethylene oxide unit) is less heat sensitive than the resins crosslinked with a prior art crosslinker (0 moles ethylene oxide), because with increasing post heat temperature the CC(T)/CC(o) ratio decreases at a faster rate for prior art resins than for resins crosslinked with crosslinkers of the invention.
- Figure 4 shows a plot of the ratio AUL (T)/A ⁇ L(0) for Resin A and Resin B at temperatures from 180°C to 230°C.
- AUL (T) is the absorption under load after postheating at the designated temperature and AUL (0) is the absorption under load before postheating.
- Figure 4 demonstrates that the absorption under load for Resin B is higher at each temperature than that of Resin A. The increase in absorption under load is greater for Resin B than Resin A as the temperature of postheating increases.
- Figure 5 plots the absorption under load against the centrifuge capacity for both Resin A and Resin B at each postheat temperature. The curve demonstrates that Resin B has a significantly better balance of properties than Resin A. At a selected AUL Resin B demonstrates higher centrifuge capacity (absorption capacity) than Resin A. Alternatively at a selected centrifuge capacity Resin B demonstrates a higher AUL than Resin A.
- Figure 6 plots the ratio of absorption under Load (AUL) to centrifuge capacity (CC) against the centrifuge capacity of Resin A and B at each post heat temperature.
- Figure 6 demonstrates at a selected centrifuge capacity the ratio of absorption under load to centrifuge capacity is higher for Resin B than for Resin A.
- Figures 3 to 6 collectively demonstrate that the use of the crosslinkers of the invention allows a significant improvement in absorption under load by postheating the resin with a smaller reduction in centrifuge capacity (absorption capacity) than demonstrated by resins crosslinked with a prior art crosslinker (Resin A).
- Figure 7 plots the level of extractables of Resins A and B at each post heat temperature against centrifuge capacity.
- Figure 8 plots the ratio of extractables to centrifuge capacity against centrifuge capacity for Resin A and Resin B at each post heat temperature.
- Figures 7 and 8 demonstrate that the use of the crosslinker of this invention (Resin B) allows higher centrifuge capacity at a given extractable level than a resin which uses a prior art crosslinker (Resin A).
- Example 35
- a sample of hydrophilic resin crosslinked with 3050 ppm of trimethylol propane polyoxyethylene triacrylate (15 moles of ethylene oxide units per mole of crosslinker) is post heated for 20 minutes at 230°C as previously described, (Resin C).
- a hydrophilic resin crosslinked with 2150 ppm of trimethylol propane triacrylate (no ethylene oxide) is post heated for 20 minutes at 190°C (Resin D).
- the absorption under load after 60 minutes for Resin C is 31.3 g/g.
- the absorption under load for Resin D after 60 minutes is 21.9 g/g.
- the absorption under load (AUL) after various absorption times are measured for both samples. The results are plotted in Figure 9.
- Figure 10 plots the ratio of AUL (t) after 60 minutes against the time for Resins C and D « Figures 9 and 10 demonstrate that the rate of absorption of Resin C is faster than that of Resin D.
- the crosslinked hydrophilic resins of the invention (Resin C) absorb fluids faster and retain fluids better under load than resins crosslinked with a prior art crosslinker (Resin D).
- Example 36
- a hydrophilic resin crosslinked with 8000 ppm trimethylolpropane polyoxyethylene triacrylate (15 moles of ethylene oxide units per mole crosslinker) is heated for 10 minutes at 215°C as previously described (Resin E).
- Resin E has an initial centrifuge capacity before postheating of 35 g/g and a final postheat treated centrifuge capacity of 29 g/g.
- a second hydrophilic resin crosslinked with trimethylolpropane triacrylate 6500 ppm (0 moles of ethylene oxide) which is not post heated and has centrifuge capacity of 29.4 g/g is also used (Resin F). Both resins are tested for absorption under load (AUL) at several times during a 1 hour period.
- AUL absorption under load
- Resin E shows on AUL of 29.6 g/g after 1 hour and Resin F shows on AUL of 22.3 g/g after 1 hour.
- the results are plotted in Figure 11.
- Figure 12 plots the ratio of AUL at various times to the AUL after 1 hour against the time for both Resin E and F.
- Figure 12 demonstrates that resins of the invention show faster absorption and better fluid retention than prior art resins (Resin F).
- the AUL of Resins E and F are measured under varying loads of from 0 to 1.0 psi (70.31 gm/cm3).
- Figure 13 demonstrates the results in graph form.
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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JP51857693A JP3474567B2 (en) | 1992-04-16 | 1993-04-14 | Crosslinked hydrophilic resin and preparation method |
EP93910596A EP0636149B2 (en) | 1992-04-16 | 1993-04-14 | Crosslinked hydrophilic resins and method of preparation |
DE69302686T DE69302686T3 (en) | 1992-04-16 | 1993-04-14 | CROSSLINKED HYDROPHILE RESINS AND METHOD FOR THE PRODUCTION THEREOF |
KR1019940703650A KR100257493B1 (en) | 1992-04-16 | 1993-04-14 | Crosslinked hydrophilic resins and method of preparation |
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GB9208449.0 | 1992-04-16 | ||
GB929208449A GB9208449D0 (en) | 1992-04-16 | 1992-04-16 | Crosslinked hydrophilic resins and method of preparation |
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WO1993021237A1 true WO1993021237A1 (en) | 1993-10-28 |
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PCT/US1993/003489 WO1993021237A1 (en) | 1992-04-16 | 1993-04-14 | Crosslinked hydrophilic resins and method of preparation |
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US (1) | US5506324A (en) |
EP (1) | EP0636149B2 (en) |
JP (1) | JP3474567B2 (en) |
KR (1) | KR100257493B1 (en) |
AU (1) | AU4103093A (en) |
DE (1) | DE69302686T3 (en) |
GB (1) | GB9208449D0 (en) |
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Also Published As
Publication number | Publication date |
---|---|
EP0636149B2 (en) | 2003-11-05 |
JP3474567B2 (en) | 2003-12-08 |
KR100257493B1 (en) | 2000-06-01 |
DE69302686T3 (en) | 2004-07-22 |
JPH07505913A (en) | 1995-06-29 |
IL105384A0 (en) | 1993-08-18 |
EP0636149A1 (en) | 1995-02-01 |
GB9208449D0 (en) | 1992-06-03 |
DE69302686D1 (en) | 1996-06-20 |
KR950700943A (en) | 1995-02-20 |
US5506324A (en) | 1996-04-09 |
EP0636149B1 (en) | 1996-05-15 |
AU4103093A (en) | 1993-11-18 |
DE69302686T2 (en) | 1996-11-28 |
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