WO2017157658A1 - Use of dipa-esterquat debonder for tissue and fluff pulp manufacturing - Google Patents
Use of dipa-esterquat debonder for tissue and fluff pulp manufacturing Download PDFInfo
- Publication number
- WO2017157658A1 WO2017157658A1 PCT/EP2017/054712 EP2017054712W WO2017157658A1 WO 2017157658 A1 WO2017157658 A1 WO 2017157658A1 EP 2017054712 W EP2017054712 W EP 2017054712W WO 2017157658 A1 WO2017157658 A1 WO 2017157658A1
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- WIPO (PCT)
- Prior art keywords
- acid
- formula
- weight
- fiber materials
- cellulose fiber
- Prior art date
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Classifications
-
- 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
- D21H21/22—Agents rendering paper porous, absorbent or bulky
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/001—Modification of pulp properties
- D21C9/002—Modification of pulp properties by chemical means; preparation of dewatered pulp, e.g. in sheet or bulk form, containing special additives
-
- 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
- D21H11/00—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only
- D21H11/16—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only modified by a particular after-treatment
-
- 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
- D21H11/00—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only
- D21H11/16—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only modified by a particular after-treatment
- D21H11/18—Highly hydrated, swollen or fibrillatable fibres
-
- 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
- D21H11/00—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only
- D21H11/16—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only modified by a particular after-treatment
- D21H11/20—Chemically or biochemically modified fibres
- D21H11/22—Chemically or biochemically modified fibres cationised
-
- 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
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/07—Nitrogen-containing compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
-
- 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
- D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
- D21H27/002—Tissue paper; Absorbent paper
- D21H27/004—Tissue paper; Absorbent paper characterised by specific parameters
- D21H27/005—Tissue paper; Absorbent paper characterised by specific parameters relating to physical or mechanical properties, e.g. tensile strength, stretch, softness
- D21H27/007—Tissue paper; Absorbent paper characterised by specific parameters relating to physical or mechanical properties, e.g. tensile strength, stretch, softness relating to absorbency, e.g. amount or rate of water absorption, optionally in combination with other parameters relating to physical or mechanical properties
Definitions
- the present invention relates to cellulose fiber materials containing 0.01 to 0.5 % by weight of ammonia compound comprising oxyalkyl radicals consisting of at least 3 carbon atoms which are biodegradable at a degree of at least 60% according the OECD 301 F method and a process for producing debonded cellulose fibers.
- Debonders are used in the manufacture of fluff pulp, tissue paper and other forms of paper.
- tissue paper paper toweling and other forms of paper
- debonders can be used to decrease density of the fiber sheet. Decreasing the density of the sheet can among other things change the absorption properties and printability of different types of paper and tissue. This allows the paper manufacturer to achieve desired end use properties.
- the first group of materials are di-alkyl dimethyl ammonium chloride where the alkyl groups are from 8 to 20 carbons long.
- the second type are materials based on quaternized imidazolines-
- US 3,821 ,068 also disclose that chembal debonders can be used to reduce the stiffness, and thus enhance the softness, of a tissue paper web.
- These materials include quaternary ammonium salts such as trimethylcocoammonium chloride, trimethyloleylammonium chloride, di(hydrogenated) tallow dimethyl ammonium chloride and trimethylstearyl ammonium chloride.
- US 4,144,122 disclose the use of complex quaternary ammonium compounds such as bis(alkoxy(2- hydroxy )propylene) quaternary ammonium chlorides to soften webs. The authors also attempt to overcome any decrease in absorbency caused by the debonders through the use of nonionic surfactants such as ethylene oxide and propylene oxide adducts of fatty alcohols.
- nonionic surfactants such as ethylene oxide and propylene oxide adducts of fatty alcohols.
- WO 1993/021382 disclose that the use of dimethyl di(hydrogenated) tallow ammonium chloride in combination with fatty acid esters of polyoxyethylene glycols may impart both softness and absorbency to tissue paper webs.
- quaternary ammonium compounds such as the well known dialkyl dimethyl ammonium salts (e.g. ditallow dimethyl ammonium chloride, ditallow dimethyl ammonium methyl sulfate, di(hydrogenated) tallow dimethyl ammonium chloride etc.) are effective chemical debonding agents. Unfortunately, these quaternary ammonium compounds are not biodegradable.
- dialkyl dimethyl ammonium salts e.g. ditallow dimethyl ammonium chloride, ditallow dimethyl ammonium methyl sulfate, di(hydrogenated) tallow dimethyl ammonium chloride etc.
- the quaternary ammonia compounds of the invention solve at least one problem of the prior art.
- the present invention accordingly provides cellulose fiber materials containing 0.01 to 0.5 % by weight of ammonia compounds of formula (I) based on the dry weight of cellulose fiber material
- R independently an alkyl group consisting of 1 to 6 carbon atoms
- R 2 independently an unsaturated or saturated acyl group
- radicals R 2 consist of 60% to 99% (w/w) of unsaturated acyl groups
- B is an anion selected from consisting of chloride, acetate, methyl sulfate, and mixtures thereof;
- the invention further provides an absorbent material consisting of the debonded cellulose fibers according the invention.
- the invention further provides a process for producing the debonded cellulose fibers according the invention.
- the invention further provides a method of debonding cellulose fibers using ammonia compounds of the formula (I).
- the invention further provides a method of lubricating cellulose fibers using liquid ammonia compounds of the formula (I).
- inventive compounds of the formula (I) are biodegradable. Another advantage is that the inventive compounds are liquid at room temperature.
- the compounds of the invention allow a dose dependent change of properties, particularly the absorbance and the burst index.
- Absorbency is the measure of the ability of a product, and its constituent webs, to absorb quantities of liquid, particularly aqueous solutions or dispersions.
- Overall absorbency as perceived by the human consumer is generally considered to be a combination of the total quantity of liquid a given mass of tissue paper will absorb at saturation as well as the rate at which the mass absorbs the liquid.
- Debonding is the masking of hydrogen bonds between the individual cellulosic fibers.
- the tissue formed has finally enhanced flexibility and lubrication between the individual fibers and is not stiff and rough.
- quaternary ammonia compounds of formula (I) which are liquid at ambient temperature, preferable have a melting point of melting range between - 20°C to +20°C, more preferable between -10 to + 15°C, particularly preferable between 0 to 10°C.
- liquid quaternary ammonia compounds of formula (I) are able to penetrate deeper into the cellulose fibers, that they remain liquid even on dry products made of the cellulose fibers thus making these products more flexible and soft.
- a further advantage is that the energy upload of a hammer mill used for subsequent fiberizing a raw cellulose fiber containing product in order to get a fluff pulp is lowered, thus the temperature of the product within the hammering process is lowered.
- Prefered fatty acids include 4 up to 40 carbon atoms, more preferably, the fatty acids are unsaturated selected from among palmitoleic acid ((Z)-9-hexadecenoic acid), oleic acid ((Z)-9-hexadecenoic acid), elaidic acid ((E)-9-octadecenoic acid), cis-vaccenic acid ((Z)-1 1- octadecenoic acid), linoleic acid ((9Z.12Z)- 9,12- octadecadienoic acid), alpha-linolenic acid ((9Z,12Z,15Z)-9,12,15-octadecatrienoic acid), gammalinolenic acid ((6Z,9Z,12Z)-6,9,12-octadecatrienoic acid), di-homo-gamma-linolenic acid ((8Z,1 1Z.14Z)- 8,11
- radicals of oleic acid More especially preferred are the quaternary ammonia compounds of formula (I) which are liquid, and where the acyl radicals are of fatty acid mixtures comprising oleic acid, stearic acid, palmitic acid and gamma- linolenic acid, where these abovementioned fatty acids preferably amount to at least 85% by weight in the fatty acid mixture.
- the quaternary ammonia compounds according to the invention which are liquid where the acyl radicals of fatty acid mixtures comprise oleic acid at least 70% by weight, preferably at least 75% by weight, more preferably at least 80% by weight, even more preferably at least 85% by weight, particularly preferably at least 90% by weight and especially preferably at least 95% by weight, the sum total of all fatty acids being 100% by weight.
- R is independently selected from the group of hexyl, pentyl, n-butyl, i-butyl, n-propyl, i-propyl, ethyl and methyl, especially preferably methyl;
- a further advantage of the quaternary ammonia compounds according to the invention is their biodegradability.
- the biodegradability is preferably determined by the OECD 301 F method. More preferably, the biodegradability is determined as specified in 28 d of OECD 301 F.
- the quaternary ammonia compounds according to the invention preferably have a biodegradability of at least 60%, even more preferably of at least 70% and especially preferably of at least 75%, the maximum biodegradability value being 100%.
- quaternary ammonia compounds of formula (I) which are miscible with organic solvents, preferably without miscibility gap at ambient temperature, preferable between 0 to 20°C.
- Sovents are any non-toxic, non-ecotoxic organic compounds having at least one hydroxyl group, preferably mono hydroxyl aliphatic compounds, di hydroxyl aliphatic compounds, oligo hydroxyl aliphatic compounds which can be oligomeric or polymeric. More preferably the solvents are selected from alcohols, glycols, oligo or poly oxyalkylene compounds, more preferably selected from or poly oxypropylen compounds, further more preferably selected from poly oxyethylene or poly oxypropylen compounds with Mw 200 to 1000 g/mol, particularly those poly oxyalkoxylenes which are terminated on one end with an unsaturated fatty acid as defined above.
- the solvents according the invention are biodegradable wherein biodegradable is understood as before mentioned.
- Miscibility in the context of the invention is understood to mean the quaternary ammonia compounds of formula (I) having a solubility of at least 10 g/l, preferably at least 20 g/l, 50 g/l, 100 g/l and especially preferably of at least 150 g/l solvent at a temperature of 20°C.
- the upper solubility limit is preferably up to and including 900 g/l, more preferably 800 g/l, 700 g/l and especially preferably up to and including 600 g/l solvent at 20°C. Determining the -solubility is comprehensible to the skilled person, who determines it preferably according to Regulation EC 440/2008 Part A.6, more preferably by the flask method of Regulation EC 440/2008 Part A.6.
- quaternary ammonia compounds of formula (I) where the fatty acid or fatty acid mixture has iodine number between 105 and 130, preferably between 1 10 and 125.
- Iodine numbers [g of iodine/100 g of sample] are determined by the method of Hanus, known as method DGF C-V 1 1 a (53) of the German Society for Fats, and arithmetically converted into the molar masses MWIN for the respective fatty acid or fatty acid mixture.
- R is independently selected from the group of hexyl, pentyl, n-butyl, i-butyl, n-propyl, i-propyl, ethyl and methyl,, especially preferably methyl;
- R 2 independently an unsaturated or saturated acyl group where the radicals R 2 consist of 60% to 99% (w/w) of unsaturated acyl group and where the unsaturated acyl group consist of at least in 70% of oleic acid; a is 1 ;
- A is independently - CH 2 CH(CH 3 ) - O - or - CH(CH 3 ) CH 2 - O -;
- B is MeOSOs-.
- cellulose fiber materials containing 0.02 to 0.3 % by weight of quaternary ammonia compounds of formula (I) based on the dry weight of cellulose fiber material, wherein
- R is methyl
- R 2 independently an unsaturated or saturated acyl group with a iodine number between 105 and 130, preferably between 1 10 and 125;
- a 1 ;
- A is independently - CH 2 CH(CH 3 ) - O - or - CH(CH 3 ) CH 2 - O -;
- B is MeOSOs " .
- cellulose fiber materials containing 0.03 to 0.2 % of liquid ammonia compounds of formula (I) based on the dry weight of cellulose fiber material, wherein R is Methyl, R 2 is oleic acid, a is 1 , A is - CH 2 CH(CH 3 ) - O - or - CH(CH 3 ) CH 2 - O -, B is MeOSOs " ; where the iodine number of R 2 is between 1 10 and 130; and where the biodegradability is at least 60% according the OECD 301 F method.
- R Methyl
- R 2 is oleic acid
- a 1
- A is - CH 2 CH(CH 3 ) - O - or - CH(CH 3 ) CH 2 - O -
- B is MeOSOs " ; where the iodine number of R 2 is between 1 10 and 130; and where the biodegradability is at least 60% according the OECD 301 F method.
- ammonia compounds of formula (I) is the low surface tension watery solutions, this causes a good penetration into the cellulose fibers.
- the quaternary debonder helps to manufacture in a high speed industrial process generating a tissue weight of ⁇ 50 g/m 2 , that is mainly used for paper towels or even tissue sheets with a weight of 12-20 g/m 2 that is typically used as toilet tissue. Examples
- REWOQUAT V 10036 ZW is the active ingredient of Varisoft 3690.
- Untreated fluff pulp from a Scandinavian mill was obtained from the high density chest. This fluff pulp was used to form hand sheets with a Rapid Kothen hand sheet former as supplied by Frank PTI using ISO 5269- 2. Four hand sheets were made for each experimental condition, including four sheets that were not treated with any debonder. The sheets were then tested for burst index, absorbency, density and softness. The data reported represents the average of each condition.
- the method for preparing the debonder samples and subsequently treating the fiber used to make hand sheets is as follows.
- the pulp received was 7.29% (w/w) consistency in water.
- the consistency needed for preparation of sheets should be 0.18% by weight.
- the water to pulp ratio was using pulp as supplied in amount of 2.467% and water 97.533% by weight based on the sum of 100% by weight. This was mixed for one hour at 400 rpm with an overhead mixer resulting in a fluff pulp slurry.
- Adogen 442 dialkyldimethyl ammonium chloride
- debonder solutions were dispersed in city water using 0.625 g of the above debonder solution in propylene glycol and 99.375 g of city water by mixing this for 90 minutes at 400 rpm resulting in sample A consisting of Adogen 442, sample B consisting of REWOQUAT V 10036 ZW and sample C consisting of the compound according the invention REWOQUAT CR 3099.
- the resulting mixtures were stirred for 5 minutes at 500 rpm at room temperature.
- the preparation of the hand sheets was performed with a Rapid Kothen Sheet Machine (FRANK-PTI) according to the product sheet number 95854 of company FRANK-PTI with some amendments.
- FRANK-PTI Rapid Kothen Sheet Machine
- a carrier board was placed with its smooth side downwards centrally on the wet sheet. Then a couch roll was rolled back and forth over the sheet for a 2-second period without additional pressure, once in each of two directions at right angles to each other. The couch roll had been placed on the edge of the screen but not on the wet sheet. After removing the sheet-forming screen together with the wet sheet and the carrier board from the supporting screen it was hit with the edge slightly inclined to the horizontal against the silicon rubber underlay releasing the board to which the wet sheet was attached on the underlay.
- the sheet was peeled from the carrier board and air dried.
- the hand sheets were further prepared for the tests by storing under controlled climate (72°F, 50% relative humidity) until constant weight.
- Burst testing is performed on the Vantage Tensile Tester (Thwing-Albert Instrument Company, USA) utilizing the Tissue Burst attachment. The lower the burst index, the weaker the test sample, which equates to better debonding.
- the sheets were test for water absorbency on a M/K Systems model 251 GATS (Gravimetric Absorption Testing System) instrument which tests Horizontal wicking.
- GATS Grammetric Absorption Testing System
- This instrument determines rate of absorption and capacity of the test substrate by placing a sample of known weight on a porous plate attached to an instrument and analytical balance.
- the porous plate is attached to a water reservoir placed on an analytical balance.
- the instrument measures the rate of absorption and capacity by measuring the quantity and speed of water leaving the reservoir that supplies the porous plate.
- the density of the sheets were measured with a Messmer micrometer Model 172M.
- tissue softness values are expressed as "hand feel". A two point increase in hand feel is considered significant and can be perceived by the average human.
- the results show the advantage of the compounds of the invention.
- the burst index is effectively lowered and not only better than the blank but at higher concentrations also better than the compounds of the art.
- the density is comparable to those of the art but clearly effectively lowered at high concentrations.
- the absorption rate is being modified in a wide range.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA3013675A CA3013675A1 (en) | 2016-03-15 | 2017-03-01 | Use of dipa-esterquat debonder for tissue and fluff pulp manufacturing |
SG11201806666YA SG11201806666YA (en) | 2016-03-15 | 2017-03-01 | Use of dipa-esterquat debonder for tissue and fluff pulp manufacturing |
CONC2018/0009198A CO2018009198A2 (en) | 2016-03-15 | 2017-03-01 | Use of dipa-esterquat disunion agent for the manufacture of fabrics and spongy pulp |
BR112018068406A BR112018068406A2 (en) | 2016-03-15 | 2017-03-01 | cellulose fiber materials, absorbent material, method of deagglomerating cellulose fibers, method of lubricating fibers and process for producing deagglutinated cellulose fibers |
EP17707885.4A EP3430196A1 (en) | 2016-03-15 | 2017-03-01 | Use of dipa-esterquat debonder for tissue and fluff pulp manufacturing |
CN201780017480.4A CN108779605A (en) | 2016-03-15 | 2017-03-01 | The purposes that DIPA-Esterquat debonding agents are produced for thin paper and Time of Fluff Slurry |
MX2018010671A MX2018010671A (en) | 2016-03-15 | 2017-03-01 | Use of dipa-esterquat debonder for tissue and fluff pulp manufacturing. |
US16/076,456 US20190040584A1 (en) | 2016-03-15 | 2017-03-01 | Use of DIPA-Esterquat Debonder For Tissue And Fluff Pulp Manufacturing |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662308532P | 2016-03-15 | 2016-03-15 | |
US62/308,532 | 2016-03-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2017157658A1 true WO2017157658A1 (en) | 2017-09-21 |
Family
ID=58191471
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2017/054712 WO2017157658A1 (en) | 2016-03-15 | 2017-03-01 | Use of dipa-esterquat debonder for tissue and fluff pulp manufacturing |
Country Status (10)
Country | Link |
---|---|
US (1) | US20190040584A1 (en) |
EP (1) | EP3430196A1 (en) |
CN (1) | CN108779605A (en) |
BR (1) | BR112018068406A2 (en) |
CA (1) | CA3013675A1 (en) |
CL (1) | CL2018002594A1 (en) |
CO (1) | CO2018009198A2 (en) |
MX (1) | MX2018010671A (en) |
SG (1) | SG11201806666YA (en) |
WO (1) | WO2017157658A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113789680B (en) * | 2021-09-16 | 2023-04-28 | 浙江理工大学 | Bamboo fiber fluff pulp and preparation method and application thereof |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3554862A (en) | 1968-06-25 | 1971-01-12 | Riegel Textile Corp | Method for producing a fiber pulp sheet by impregnation with a long chain cationic debonding agent |
US3755220A (en) | 1971-10-13 | 1973-08-28 | Scott Paper Co | Cellulosic sheet material having a thermosetting resin bonder and a surfactant debonder and method for producing same |
US3821068A (en) | 1972-10-17 | 1974-06-28 | Scott Paper Co | Soft,absorbent,fibrous,sheet material formed by avoiding mechanical compression of the fiber furnish until the sheet is at least 80% dry |
US4144122A (en) | 1976-10-22 | 1979-03-13 | Berol Kemi Ab | Quaternary ammonium compounds and treatment of cellulose pulp and paper therewith |
WO1993021382A1 (en) | 1992-04-09 | 1993-10-28 | The Procter & Gamble Company | Soft absorbent tissue paper containing a biodegradable quaternized amine-ester softening compound and a permanent wet strength resin |
US5415737A (en) * | 1994-09-20 | 1995-05-16 | The Procter & Gamble Company | Paper products containing a biodegradable vegetable oil based chemical softening composition |
US5981044A (en) * | 1993-06-30 | 1999-11-09 | The Procter & Gamble Company | Multi-layered tissue paper web comprising biodegradable chemical softening compositions and binder materials and process for making the same |
WO2000077303A1 (en) * | 1999-06-16 | 2000-12-21 | The Procter & Gamble Company | Soft tissue product exhibiting improved lint resistance and process for making |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1103124A (en) * | 1994-06-17 | 1995-05-31 | 重庆西泉造纸厂 | Bamboo material fibre fluff pulp and making method |
MXPA01009705A (en) * | 1999-04-16 | 2002-03-14 | Kimberly Clark Co | Methods of making fiber bundles and fibrous structures. |
US6547928B2 (en) * | 2000-12-15 | 2003-04-15 | The Procter & Gamble Company | Soft tissue paper having a softening composition containing an extensional viscosity modifier deposited thereon |
US7311853B2 (en) * | 2002-09-20 | 2007-12-25 | The Procter & Gamble Company | Paper softening compositions containing quaternary ammonium compound and high levels of free amine and soft tissue paper products comprising said compositions |
CA2461629C (en) * | 2003-03-24 | 2012-05-08 | Nof Corporation | Paper additive composition and method for producing paper using the same |
RU2007113818A (en) * | 2004-10-13 | 2008-10-20 | Клариант Файненс (Бви) Лимитед (Vg) | COMPLEX ETHERS OF FATTY ACIDS AND ALKANOLAMINES AND THEIR APPLICATION AS SOFTENING AGENTS |
WO2014017073A1 (en) * | 2012-07-25 | 2014-01-30 | 星光Pmc株式会社 | Softening agent for paper, paper, and method for producing sanitary paper |
-
2017
- 2017-03-01 BR BR112018068406A patent/BR112018068406A2/en not_active Application Discontinuation
- 2017-03-01 SG SG11201806666YA patent/SG11201806666YA/en unknown
- 2017-03-01 CO CONC2018/0009198A patent/CO2018009198A2/en unknown
- 2017-03-01 US US16/076,456 patent/US20190040584A1/en not_active Abandoned
- 2017-03-01 EP EP17707885.4A patent/EP3430196A1/en not_active Withdrawn
- 2017-03-01 MX MX2018010671A patent/MX2018010671A/en unknown
- 2017-03-01 WO PCT/EP2017/054712 patent/WO2017157658A1/en active Application Filing
- 2017-03-01 CA CA3013675A patent/CA3013675A1/en not_active Abandoned
- 2017-03-01 CN CN201780017480.4A patent/CN108779605A/en active Pending
-
2018
- 2018-09-11 CL CL2018002594A patent/CL2018002594A1/en unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3554862A (en) | 1968-06-25 | 1971-01-12 | Riegel Textile Corp | Method for producing a fiber pulp sheet by impregnation with a long chain cationic debonding agent |
US3755220A (en) | 1971-10-13 | 1973-08-28 | Scott Paper Co | Cellulosic sheet material having a thermosetting resin bonder and a surfactant debonder and method for producing same |
US3821068A (en) | 1972-10-17 | 1974-06-28 | Scott Paper Co | Soft,absorbent,fibrous,sheet material formed by avoiding mechanical compression of the fiber furnish until the sheet is at least 80% dry |
US4144122A (en) | 1976-10-22 | 1979-03-13 | Berol Kemi Ab | Quaternary ammonium compounds and treatment of cellulose pulp and paper therewith |
WO1993021382A1 (en) | 1992-04-09 | 1993-10-28 | The Procter & Gamble Company | Soft absorbent tissue paper containing a biodegradable quaternized amine-ester softening compound and a permanent wet strength resin |
US5981044A (en) * | 1993-06-30 | 1999-11-09 | The Procter & Gamble Company | Multi-layered tissue paper web comprising biodegradable chemical softening compositions and binder materials and process for making the same |
US5415737A (en) * | 1994-09-20 | 1995-05-16 | The Procter & Gamble Company | Paper products containing a biodegradable vegetable oil based chemical softening composition |
WO2000077303A1 (en) * | 1999-06-16 | 2000-12-21 | The Procter & Gamble Company | Soft tissue product exhibiting improved lint resistance and process for making |
Also Published As
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CL2018002594A1 (en) | 2018-11-05 |
BR112018068406A2 (en) | 2019-01-15 |
SG11201806666YA (en) | 2018-09-27 |
EP3430196A1 (en) | 2019-01-23 |
CA3013675A1 (en) | 2017-09-21 |
US20190040584A1 (en) | 2019-02-07 |
CN108779605A (en) | 2018-11-09 |
CO2018009198A2 (en) | 2018-09-20 |
MX2018010671A (en) | 2018-11-09 |
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