US20080302497A1 - Paper Product with Increased Relative Wet Tensile Strength and Softness, Method for Production and Use Thereof - Google Patents
Paper Product with Increased Relative Wet Tensile Strength and Softness, Method for Production and Use Thereof Download PDFInfo
- Publication number
- US20080302497A1 US20080302497A1 US11/659,523 US65952305A US2008302497A1 US 20080302497 A1 US20080302497 A1 US 20080302497A1 US 65952305 A US65952305 A US 65952305A US 2008302497 A1 US2008302497 A1 US 2008302497A1
- Authority
- US
- United States
- Prior art keywords
- segment
- paper product
- polyethyleneimine
- polyalkyleneglycol
- polyalkyleneoxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- OAVAMXHUKYHNIV-UHFFFAOYSA-N C.C.C.C.C.C.CCNCN(C)CNCN Chemical compound C.C.C.C.C.C.CCNCN(C)CNCN OAVAMXHUKYHNIV-UHFFFAOYSA-N 0.000 description 4
- 0 C.C.[H]O[1*]O[2*]O Chemical compound C.C.[H]O[1*]O[2*]O 0.000 description 4
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/53—Polyethers; Polyesters
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
- D21H17/56—Polyamines; Polyimines; Polyester-imides
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/18—Reinforcing agents
- D21H21/20—Wet strength agents
Definitions
- the present invention relates to flat paper products having increased relative wet strength and softness, a method for the production of the same and the use of paper products of this type in the form of tissue products. This is achieved by cross-linkage of the cellulose fibres contained in the paper product with a cationic graft copolymer which is constructed on the basis of polyethyleneoxide- or polyethyleneglycol segments and polyethyleneimine segments.
- the aqueous pulp stock is then passed during the industrial process to the machine wire(s), is formed there and partly drained and passes subsequently into the dry part of the tissue machine.
- the dry part there is the so-called steam-heated yankee cylinder which has a surface temperature of 80 to 140° C.
- one or more gas-heated hoods can be situated thereabove through which hoods hot air is blown onto the tissue web. The air is heated for this purpose to temperatures of 200 to 750° C.
- the hardening process of the wet strength agents begins which is concluded during the subsequent storage of the finished tissue web, the so-called subsequent ripening.
- a potential wet strength agent can be absorbed onto the cellulose fibre during application on the pulp stock, said agent is advantageously water-soluble or water-dispersible and cationic since the cellulose fibres used during paper production are negatively charged. Therefore the use of cationic polymers as wet strength agents in the paper or tissue industry, which are based in part on very different chemical structurings such as polyamides or polyacrylamides, is regarded as current state of the art. These wet strength agents are normally added in quantities of 8 to 10 kg/tonne for household tissues. The cellulose fibres of the paper or tissues hold together in the dry state in the network of a sheet by means of fibre-fibre contact points which are based on van der Waals or hydrogen bonds.
- wet strength papers such as e.g. kitchen or household towel or toilet tissue
- wet strength agents are added which have the task of forming bonds which are at least temporarily resistant to water.
- various chemically based polymer wet strength agents are available in paper or tissue production which are described in the relevant literature, e.g. in “Papermaking Chemistry”, Book 4, Ed. Leo Neimo, pp. 288-301.
- MF melamine-formaldehyde resins
- a disadvantage with the above-mentioned wet strength agents is, on the one hand, that the treated tissue does in fact have increased wet strength but has reduced softness. The sought softness must then be achieved by an additional mechanical treatment of the tissue.
- a further disadvantage of the PAEs is the production-caused content of organic halogen compounds.
- WO 00/40639 describes a PAE-based wet strength agent with a low content of organically bonded chlorine.
- water-dispersible wet strength agents based on polyisocyanate are described in DE 196 40 205 A1, which are obtained by conversion of the initial components polyisocyanate, polyalkyleneoxide polyether alcohol, of a quaternised aminopolyalkyleneoxide polyether alcohol and also possibly further auxiliary materials and additives.
- DE 698 14 359 T2 teaches that e.g. polyethyleneimine belongs to the temporary wet strength agents.
- the wet strength should thereby be increased without having negative effects on the softness.
- the absorption of the paper should also not be negatively affected.
- the application of chemicals should be effected in as simple a manner as possible directly in the pulp or during production of the paper product. Multistage methods, such as e.g. mixing of treated pulp with untreated pulp as described for example in DE 689 16 860 T2, should however be avoided.
- the use of organically bonded halogens in the treatment chemicals should be avoided.
- a paper product with increased relative wet strength and softness which contains cellulose fibres which are cross-linked with a graft copolymer comprising a polyethyleneimine segment of the general formula I,
- x, y and z being chosen such that the molar mass of the polyethyleneimine segment is in the range of 1000 to 2000000 dalton, and also at least one polyalkyleneoxide- and/or at least one polyalkyleneglycol segment of the general formula II,
- R 1 and R 2 independently of each other C 1 to C 12 -alkyl, n being chosen such that the molar mass of the polyalkyleneoxide- or polyalkyleneglycol segment is in the range of 350 to 2000000 dalton.
- the backbone of the graft copolymer comprises polyethyleneimine, there being bonded to the latter grafts comprising at least one polyalkyleneoxide and/or at least one polyalkyleneglycol.
- the graft copolymer has a backbone comprising at least one polyalkyleneoxide and/or at least one polyalkyleneglycol, grafts comprising polyethyleneimine then being present.
- the graft copolymer comprises polyethyleneimine with a molar mass in the range of 20000 to 1000000 dalton.
- polyethyleneglycol is used as polyalkyleneglycol or preferably polyethyleneoxide as polyalkyleneoxide. These thereby have preferably a molar mass in the range of 350 to 1000000 dalton, particularly preferred of 350 to 80000 dalton.
- a terminal hydroxyl group of the polyalkyleneoxide and/or polyalkyleneglycol is preferably blocked.
- the terminal hydroxy group is thereby blocked with a methoxy, ethoxy, propyloxy, butyloxy and/or benzyloxy group.
- the free terminal hydroxyl group of the polyalkyleneglycol or polyalkyleneoxide is converted into a chemical-reactive group, i.e. by reaction with epihalogenhydrin by forming a polyethyleneglycolglycidyl ether.
- Polyalkyleneglycols modified in this manner then form, by chemical reaction with the primary and secondary amine groups of the polyethyleneimine, the graft copolymers which are desired for the paper products according to the invention.
- a method for the production of flat paper products with increased relative wet strength and softness is provided from a pulp stock, in which there is added to the pulp stock a graft copolymer comprising a polyethyleneimine segment of the general formula I
- x, y, z being chosen such that the molar mass is in the range of 1000 to 2000000 dalton, and also at least one polyalkyleneoxide- and/or at least one polyalkyleneglycol segment of the general formula II
- R 1 and R 2 independently of each other C 1 to C 12 -alkyl and n being chosen such that the molar mass thereof is in the range of 350 to 2000000 dalton, and/or the paper product is treated during production thereof or subsequently with the graft copolymer.
- Polyalkyleneglycols can be coupled with polyethyleneimine by various methods in order thus to obtain the desired graft copolymers.
- Sung et al. describe the synthesis of polyalkyleneglycols grafted on PEI. They begin thereby in the synthesis of a polyethyleneglycol (MPEG) which is terminated on one side with a methyl group and is converted with epichlorohydrin with base effect into an epoxy-terminated MPEG.
- MPEG polyethyleneglycol
- This epoxy-terminated MPEG is grafted onto the PEI in a further synthesis step so that a graft copolymer is obtained.
- a further method of synthesising graft copolymers based on polyalkyleneglycol-polyethyleneimine resides in bonding a polyalkyleneglycol carboxylic acid, by the coupling methods currently known from peptide chemistry, to the primary or secondary amine groups of the PEI by linkage of peptide bonds.
- the current coupling methods e.g. with the help of carbodiimides are described for example in “Amino acids, Peptides, Proteins”, H. Jakubke, H. Jeschkeit, Licensed Edition for the Chemistry Press, Weinheim, 1982, ISBN 3-527-25892-2.
- More recent coupling methods with water-soluble coupling reagents such as e.g.
- N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride are described for example in Sheehan et al. (J. Am. Chem. Soc. 95, 875 (1973)), Nozaki et al. (Bull. Chem. Soc. Jpn. 55, 2165 (1982)) and Schmidt et al. (J. Chem. Soc. Chem. Commun. 1687 (1992)).
- polyethyleneglycols It is also possible with the above-mentioned methods to graft polyethyleneimines onto polyethyleneglycols. This is possible for example by using bifunctional polyethyleneglycols, such as e.g. polyethyleneglycol diacids or polyethyleneglycolbisglycidyl ether.
- bifunctional polyethyleneglycols such as e.g. polyethyleneglycol diacids or polyethyleneglycolbisglycidyl ether.
- coupling methods with activators which permit coupling under aqueous conditions such as e.g. N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride.
- activators which permit coupling under aqueous conditions
- the coupling can be implemented in principle also with organic water-free solvents by means of carbodiimides and carbonyl diimidazoles.
- the above-mentioned graft copolymer is added as an additive to a paper product, in particular to a so-called tissue product.
- Further paper products, to which the described graft copolymer can be added as additive are inter alia graph paper, newspaper, cardboard, copy paper and special papers, such as for example banknotes or even filter papers.
- a so-called tissue paper, which tissue products comprise, differs from normal papers in particular by its very low basis weight of normally less than 40 g/m 2 .
- tissue papers or better as raw tissue papers the single-layer intermediate products, which come from the paper machine, comprising light papers, i.e. produced with a low basis weight, which were dry-creped as a rule on a so-called yankee cylinder with the help of a crepe scraper.
- the single-layer raw tissue comprising respectively one or more layers can thereby be constructed.
- tissue products all the single or multilayer end products which are produced from raw tissue and orientated to the requirements of the end user, i.e. are manufactured with the most varied of requirement profiles.
- tissue papers are the good capacity to absorb strength energy, their drapability, good textile-like flexibility, properties which are often termed as crumple-softness, high surface softness, a high specific volume with a tactile thickness, as high a liquid absorption capacity as possible and, according to the application, a suitable wet and dry strength and also an interesting optical appearance of the outer product surface. Because of these properties, tissue papers are processed into tissue products (tissue paper products) and are then available to the end user in the most varied of forms and assemblies, for example as wipes, handkerchiefs, household towels, in particular as kitchen towels, as sanitary products, (e.g. toilet papers), as paper tissues, cosmetic tissues or serviettes.
- Tissue papers are produced nowadays as a rule by three different methods. These methods are:
- the methods differ as a result of the construction of the tissue machine.
- the press for mechanical draining of the tissue web is therefore replaced by throughflow cylinders through which hot air is blown (energetic drying).
- the construction of the so-called wire part, in which the web is formed and partially drained, can be different.
- the sheet formation can be formed on only one wire (breast roller former) between two wires (C-wrap or S-wrap former) or between one wire and a felt (crescent former).
- the constant part of a tissue machine begins with the pulper in which dried pulp is dissolved or with a stacked tower in which up to several hundred cubic meters of pulp stock can be stored and ends at the material inlet. Since in a plurality of circulations material-water suspensions are returned from the machine to different points in the constant part, these circulations also fall in the constant part region (e.g. wire water or machine rejects). Pulpers are used if dried pulp is to be broken up. This pulp is delivered as a rule from an external pulp factory. Stacked towers are used if pulp is produced in the same works (integrated factory) or waste paper is processed. These two raw materials are then not dried before use on the tissue but only drained up to a material density of maximum 25% (250 g fibres in 1 l water) in order to separate the circulations of the tissue machine and the pulp factory or waste paper processing.
- a material density of maximum 25% 250 g fibres in 1 l water
- pulps or types of waste paper can be used as fibre material. Both sulphate and sulphite pulps are used.
- the bleaching can be implemented without chlorine or with chlorine-containing chemicals, such as e.g. hypochlorite.
- the pulp is generally produced from different woods (deciduous and coniferous woods).
- Other fibrous materials such as e.g. CTMP (Chemical Thermo Mechanical Pulp—chemical-mechanical wood material), can likewise be used.
- CTMP Chemical Thermo Mechanical Pulp—chemical-mechanical wood material
- the fibrous materials can be used individually or mixed. If a multilayer material inlet is used, generally different fibrous material is used in all the different layers. Hence in the different legs of the constant part, different units can be used.
- the fibrous material has both an influence on the units used in the constant part of the tissue machine and on the metering point for the chemicals which are used.
- Dependent upon the type of fibre e.g. more or fewer cleaning units must be used (thick material cleaner, cleaner, pressure sorter etc.). Also refiners are used differently according to the type of fibre.
- the tissue production is assisted, improved or controlled by the use of chemicals. Normally a difference is thereby made between process chemicals, functional chemicals, coating chemicals for the yankee cylinder and chemicals for cleaning.
- Process chemicals are inter alia pH regulators, defoamers, retention and flocculation aids for improving the fibre retention during the sheet formation or for coagulating fibres in a disc filter or a microflotation, disruptive material fixers for binding undesired particles in the system and also biocides for attacking bacteria and for avoiding the formation of slime.
- Functional chemicals serve inter alia as wet strength agents for increasing the strength of the wet tissue paper, as dry strength agents for increasing the strength of the dry tissue paper, as so-called softener/debonders for improving the surface softness and for reducing the stiffness of the tissue paper and also as colourants and optical brighteners for increasing the degree of whiteness.
- Coating chemicals for the yankee cylinder are used inter alia for controlling the adhesion of the tissue paper on the yankee cylinder, the number of chemicals used being able to vary normally between one and for instance five.
- Suitable chemicals for cleaning are inter alia organic and inorganic acids and caustic sodas. These are normally used for cleaning the wires and felts in the tissue machine.
- treatment chemicals can be effected also on the Pope roller with production of a treatment agent film which is subsequently transferred to the tissue web during the rolling process.
- Treatment chemicals can be added, also within doubling machines or within processing machines, onto the outer layers of the tissue paper or of the tissue product.
- the metering point is not only dependent upon the units contained in the constant part but also upon the fibrous material which is used, the process water quality (pH value, water hardness, conductivity etc.) and also upon the use of different chemicals on the same tissue machine. If for example wet strength agents are used together with dry strength agents and/or softeners, it must be ensured that both or all three chemicals can be absorbed onto the fibre and the metering points must be chosen such that the chemicals cannot react with each other before they are fixed on the fibres.
- reaction time with the fibrous material can be of different lengths.
- the metering point can be nearer and further removed from the material inlet according to the fibrous material which is used.
- FIG. 1 shows the basis weight of the graft copolymers produced according to the examples, in comparison with a wet strength agent of the of the art.
- FIG. 2 shows the breaking length in the dry state of the graft copolymers according to examples 2 to 9 in comparison with a wet strength agent of the state of the art.
- FIG. 3 shows the breaking length in the wet state of the graft copolymers according to examples 2 to 9 in comparison with a wet strength agent of the state of the art.
- FIG. 4 shows the relative wet moisture of the graft copolymers according to examples 2 to 9 in comparison with a wet strength agent of the state of the art.
- water 0.5 ml
- the reaction mixture was dissolved in 150 ml chloroform and mixed with 100 ml water.
- sodium dihydrogen phosphate NaH 2 PO 4
- the aqueous phase was adjusted to a pH value of 7.
- the precipitated solid material was filtered off and discarded.
- the organic phase was washed twice with 50 ml water and subsequently dried with sodium sulphate. Subsequently, the chloroform was distilled off in the vacuum. Epichlorohydrin residue remaining in the product was removed in the high vacuum at 10 ⁇ 2 -10 ⁇ 3 mbar.
- the laboratory sheet formation was effected according to the rapid Köthen method.
- the production of the laboratory sheets was effected according to DIN EN ISO 5269-2: 1998.
- the rapid Köthen laboratory sheet former comprises a sheet forming device, the transition elements and a plurality of vacuum dryers. In principle a circular laboratory sheet is formed from a fibre suspension on a wire cloth by suction effect. The sheet is subsequently dried under defined conditions.
- the basis weight of the formed sheet is 75 ⁇ 2 g/m 2 otro (oven dried), i.e. one sheet has a mass of 2.36 g ⁇ 0.06 g.
- the pulp used for the tests was non-predried spruce sulphite pulp (Pulp Factory Mannheim) with a degree of beating of 15 SR.
- a pulp suspension with a material density of 0.236% was used to produce the laboratory sheets.
- the chemicals to be tested were added in a 2.5% solution to a litre of the pulp stock until concentrations of 3.6 and 9 kg/t were set.
- the reaction time with constant agitation was always 2 min, thereafter the laboratory sheet formation was effected according to the mentioned method.
- the laboratory sheets were conditioned to normal conditions (23° C., 50% relative humidity) (DIN EN 20187 1993).
- breaking force The strength (breaking force) of paper is the force measured during the test at the moment of breakage of the sample.
- the samples used had a width of 15 mm, the free gripped length was 100 mm.
- the testing was effected following DIN EN ISO 1924-2 1994-04. Wet breaking loads were tested on papers which were immersed in advance in distilled water for 30 s (DIN ISO 3781 1994-10).
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Cleaning Implements For Floors, Carpets, Furniture, Walls, And The Like (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004038132.1 | 2004-08-05 | ||
DE102004038132A DE102004038132B3 (de) | 2004-08-05 | 2004-08-05 | Papiererzeugnis mit erhöhter relativer Nassreißfestigkeit und Weichheit, Verfahren zu dessen Herstellung sowie dessen Verwendung |
PCT/EP2005/007962 WO2006015698A1 (de) | 2004-08-05 | 2005-07-21 | Papiererzeugnis mit erhöhter relativer nassreissfestigkeit und weichheit, verfahren zu dessen herstellung sowie dessen verwendung |
Publications (1)
Publication Number | Publication Date |
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US20080302497A1 true US20080302497A1 (en) | 2008-12-11 |
Family
ID=34981292
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/659,523 Abandoned US20080302497A1 (en) | 2004-08-05 | 2005-07-21 | Paper Product with Increased Relative Wet Tensile Strength and Softness, Method for Production and Use Thereof |
Country Status (10)
Country | Link |
---|---|
US (1) | US20080302497A1 (de) |
EP (1) | EP1774099B1 (de) |
CN (1) | CN1993520A (de) |
AT (1) | ATE383468T1 (de) |
AU (1) | AU2005270516B2 (de) |
DE (2) | DE102004038132B3 (de) |
ES (1) | ES2299058T3 (de) |
MX (1) | MX2007001277A (de) |
PL (1) | PL1774099T3 (de) |
WO (1) | WO2006015698A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100000694A1 (en) * | 2006-08-31 | 2010-01-07 | Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. | Paper product and method for production thereof and use thereof |
US20130126113A1 (en) * | 2011-11-22 | 2013-05-23 | Buckman Laboratories International, Inc. | Control Of Wet Strength Resin Fouling Of Paper-Making Felt |
US20140262091A1 (en) * | 2013-03-14 | 2014-09-18 | Kemira Oyj | Compositions and methods of making paper products |
US20150167248A1 (en) * | 2012-06-25 | 2015-06-18 | Katayama Chemical, Inc. | Process for manufacturing paperboard |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009044228B4 (de) | 2009-10-09 | 2012-08-16 | Weiser Chemie + Technik UG (haftungsbeschränkt) | Verfahren zur Erzeugung nassverfestigter Papiere |
DE102013205585A1 (de) * | 2013-03-28 | 2014-10-16 | Siemens Aktiengesellschaft | Cellulosematerial mit Imprägnierung und Verwendung dieses Cellulosematerials |
Citations (12)
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US2926116A (en) * | 1957-09-05 | 1960-02-23 | Hercules Powder Co Ltd | Wet-strength paper and method of making same |
US2926154A (en) * | 1957-09-05 | 1960-02-23 | Hercules Powder Co Ltd | Cationic thermosetting polyamide-epichlorohydrin resins and process of making same |
US3733290A (en) * | 1970-10-12 | 1973-05-15 | American Cyanamid Co | Polyamidepolyamine-epichlorohydrin wet strength resin |
US4461858A (en) * | 1980-05-16 | 1984-07-24 | E. I. Du Pont De Nemours And Company | Polyvinylalcohol/melamine-formaldehyde interaction products |
US4566943A (en) * | 1983-03-18 | 1986-01-28 | W. R. Grace & Co. | Wet strength material |
US4605702A (en) * | 1984-06-27 | 1986-08-12 | American Cyanamid Company | Temporary wet strength resin |
US5200037A (en) * | 1988-05-23 | 1993-04-06 | The Procter & Gamble Company | Absorbent structures from mixed furnishes |
US6201060B1 (en) * | 1996-09-30 | 2001-03-13 | Bayer Aktiengesellschaft | Water dispersable, isocyanates with enhanced absorbing capacity as paper auxiliary agents |
US6429253B1 (en) * | 1997-02-14 | 2002-08-06 | Bayer Corporation | Papermaking methods and compositions |
US6576687B1 (en) * | 1997-07-05 | 2003-06-10 | Bayer Aktiengesellschaft | Wet-strength agent with low DCP content |
US20040149411A1 (en) * | 2001-06-11 | 2004-08-05 | Krueger Ellen | Wet-strength finishing agents for paper |
US20050013992A1 (en) * | 2001-11-21 | 2005-01-20 | Azad Michael M | Crosslinked polyamine coating on superabsorbent hydrogels |
Family Cites Families (2)
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DE19909835A1 (de) * | 1999-03-05 | 2000-09-07 | Sca Hygiene Prod Gmbh | Mehrschichtige Tissuebahn, Tissueprodukt sowie deren Herstellung |
DE10346750A1 (de) * | 2003-10-06 | 2005-04-21 | Basf Ag | Verfahren zur Herstellung von Papier, Pappe und Karton |
-
2004
- 2004-08-05 DE DE102004038132A patent/DE102004038132B3/de not_active Expired - Fee Related
-
2005
- 2005-07-21 CN CNA2005800260436A patent/CN1993520A/zh active Pending
- 2005-07-21 PL PL05764217T patent/PL1774099T3/pl unknown
- 2005-07-21 EP EP05764217A patent/EP1774099B1/de not_active Not-in-force
- 2005-07-21 WO PCT/EP2005/007962 patent/WO2006015698A1/de active IP Right Grant
- 2005-07-21 AT AT05764217T patent/ATE383468T1/de not_active IP Right Cessation
- 2005-07-21 US US11/659,523 patent/US20080302497A1/en not_active Abandoned
- 2005-07-21 DE DE502005002520T patent/DE502005002520D1/de active Active
- 2005-07-21 ES ES05764217T patent/ES2299058T3/es active Active
- 2005-07-21 MX MX2007001277A patent/MX2007001277A/es active IP Right Grant
- 2005-07-21 AU AU2005270516A patent/AU2005270516B2/en not_active Ceased
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2926116A (en) * | 1957-09-05 | 1960-02-23 | Hercules Powder Co Ltd | Wet-strength paper and method of making same |
US2926154A (en) * | 1957-09-05 | 1960-02-23 | Hercules Powder Co Ltd | Cationic thermosetting polyamide-epichlorohydrin resins and process of making same |
US3733290A (en) * | 1970-10-12 | 1973-05-15 | American Cyanamid Co | Polyamidepolyamine-epichlorohydrin wet strength resin |
US4461858A (en) * | 1980-05-16 | 1984-07-24 | E. I. Du Pont De Nemours And Company | Polyvinylalcohol/melamine-formaldehyde interaction products |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US20100000694A1 (en) * | 2006-08-31 | 2010-01-07 | Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. | Paper product and method for production thereof and use thereof |
US20130126113A1 (en) * | 2011-11-22 | 2013-05-23 | Buckman Laboratories International, Inc. | Control Of Wet Strength Resin Fouling Of Paper-Making Felt |
US20150167248A1 (en) * | 2012-06-25 | 2015-06-18 | Katayama Chemical, Inc. | Process for manufacturing paperboard |
US9546452B2 (en) * | 2012-06-25 | 2017-01-17 | Katayama Chemical, Inc. | Process for manufacturing paperboard |
US20140262091A1 (en) * | 2013-03-14 | 2014-09-18 | Kemira Oyj | Compositions and methods of making paper products |
US9562326B2 (en) * | 2013-03-14 | 2017-02-07 | Kemira Oyj | Compositions and methods of making paper products |
Also Published As
Publication number | Publication date |
---|---|
AU2005270516B2 (en) | 2010-06-24 |
ATE383468T1 (de) | 2008-01-15 |
EP1774099A1 (de) | 2007-04-18 |
AU2005270516A1 (en) | 2006-02-16 |
DE102004038132B3 (de) | 2006-04-13 |
EP1774099B1 (de) | 2008-01-09 |
PL1774099T3 (pl) | 2008-08-29 |
CN1993520A (zh) | 2007-07-04 |
ES2299058T3 (es) | 2008-05-16 |
WO2006015698A1 (de) | 2006-02-16 |
DE502005002520D1 (de) | 2008-02-21 |
MX2007001277A (es) | 2007-07-19 |
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