US3887427A - Process for sizing cellulose fibers - Google Patents

Process for sizing cellulose fibers Download PDF

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Publication number
US3887427A
US3887427A US271858A US27185872A US3887427A US 3887427 A US3887427 A US 3887427A US 271858 A US271858 A US 271858A US 27185872 A US27185872 A US 27185872A US 3887427 A US3887427 A US 3887427A
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United States
Prior art keywords
cellulose fibers
fibers
carbamoyl chloride
weight
material containing
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.)
Expired - Lifetime
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US271858A
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English (en)
Inventor
Karin Ulla Elisabet Helmer
Alf Ragnar Reuterhall
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Kemanord AB
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Kemanord AB
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Publication date
Priority claimed from SE12622/71A external-priority patent/SE356088B/xx
Application filed by Kemanord AB filed Critical Kemanord AB
Priority to US05/561,562 priority Critical patent/US3966484A/en
Application granted granted Critical
Publication of US3887427A publication Critical patent/US3887427A/en
Anticipated expiration legal-status Critical
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/402Amides imides, sulfamic acids
    • D06M13/425Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/224Esters of carboxylic acids; Esters of carbonic acid
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/325Amines
    • D06M13/342Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/402Amides imides, sulfamic acids
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H17/00Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03Non-macromolecular organic compounds
    • D21H17/05Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/07Nitrogen-containing compounds
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H17/00Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03Non-macromolecular organic compounds
    • D21H17/05Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/14Carboxylic acids; Derivatives thereof

Definitions

  • the present invention relates to a process for the sizing of materials containing cellulosic fibers (e.g. paper) by the use of carbamoyl chlorides.
  • No Drawings PROCESS #FOR SIZING CELLULOSE FIBERS BACKGROUND Sizing refers to the treatment of either cellulosic pulp fibers or an already formed cellulosic material with chemicals which control the wettability and surface properties of the final cellulosic product.
  • Paper frequently is sized with resinates which are fixed to the cellulose fibers by means of aluminum sulphate (alum).
  • alum aluminum sulphate
  • Another well known sizing agent which is fixed by means of reacting with the hydroxyl groups of the cellulose is based on alkyl ketene dimers. This agent is usually added to the stock dispersed in a cationic emulsifier.
  • Alkylketene dimers have certain advantages over resinates.
  • One advantage is that the pH of the stock is kept within the range of 7 8 compared to a pH range of 4.5 6.5 which is used when the resinates are used as sizes which among other things imparts improved aging properties to the paper and makes it possible to use alkaline fillers, such as calcium carbonate.
  • alkaline fillers such as calcium carbonate.
  • considerably lesser amounts of ketene dimers are required to obtain a certain degree of hydrophobicity and the sizing thus obtained is permanent.
  • the paper will have improved resistance to lactic acid,
  • a disadvantage when employing alkylketene dimers that no complete sizing effect is achieved until curing of the material for example, by storing at room temperature for about 48 hours or by heating to a temperature of 100C for minutes.
  • Another disadvantage is that the sizing with alkylketene dimers is sensitive to alum present in the stock.
  • anhydrides of carboxylic acids as sizing agents, such as anhydrides of stearic acid or alkyl succinic acid.
  • Said 'anhydrides do not have any of the above mentioned disadvantages that are encountered when employing resinates and ketene dimers, but greater amounts of the anhydride additives are required in order to achieve the same sizing effect as with the ketene dimers.
  • catalysts In order to enhance the sizing effect it is common to add catalysts to the anhydrides so these catalysts are called siz- ,ing promoters and are used in relatively large amounts in combination with the anhydrides.
  • R is an organic, hydrophobic hydrocarbon group comprising 8 40 carbon-,iatq ms and R is hydrogen, lower alkyl or has thesiam ejaning as R THE MATERIALS CONTAII I NCi.
  • CELLULOSIC FIBERS The cellulosic fibers can be present in the form of a water suspension or in a more concentrated form, such as paperboard, fiberboard, 'or particle board, or they canbe included or admixed with other materials such as semi-synthetic paper containing plastics in addition to the cellulosic fibers.
  • the carbamoyl chloride has the general formula R o l N (3 where R is an organic, hydrophobic hydrocarbon group comprising 8 40 carbon atoms and R is hydro gen, lower alkyl or has the same meaning as R
  • suitable hydrophobic groups are (a) a higher alkyl having between 8 and 40 carbon atoms (such as decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, tetracosy], and pentacosyl although those having about 12 30 carbon atoms are generally preferred, (b) the corresponding alkenyl groups having between 8 and 40 carbon atoms (such as decenyl, tridencenyl, heptadecenyl, octadecenyl, eicosenyl, tricoseny
  • inert substituents may be mentioned ether, carboalkoxy, alkyloxy, aryloxy, arylalkyloxy, keto(carbonyl)-tert. amide groups etc.
  • radicals which should not be present to any great extent in the hydrophobic group may be mentioned e.g. hydroxyl groups, primary and secondary amino groups, unstable halogenes, and carboxyl groups or other acidic groups.
  • R preferably is an alkyl group comprising 12 30 carbon atoms and R is hydrogen; lower alkyl or has the same meaning as R
  • the carbamoyl chlorides can be prepared according to known methods for instance by phosgenisation of the corresponding amines.
  • an aqueous suspension of cellulose fibers can be brought into contact with the carbamoyl chloride, which optionally can be dispersed in a suitable way.
  • a solution or dispersion of the carbamoyl chloride chloroformate also can be brought into contact with a material containing cellulose fibers, such as paper.
  • the carbamoyl chlorides which are employed in the process of the present invention show a certain cationic activity and consequently retention to the cellulose fibers.
  • some additional retention agent may be omitted, e.g. for surface sizing or dipping concentrated cellulose fibcrs such as paper board,
  • carbamoyl chloride when added to an aqueous suspension of cellulose fibers it is frequently desirable to employ a dispersion of the carbamoyl chlorides, and thus use an emulsifier in combination with the carbamoyl chloride compounds.
  • an emulsifier having anionic, cationic or nonionic properties or a mixture of these may be used.
  • Especially preferred emulsifiers are the cationics, e.g. polyethylene imines,
  • emulsion agent showing a good reten- EXAMPLE 2 tion to the fibers are quertones or aminohydrochlorides containing at least one alkyl group having 8 22 carbon atoms, such as dimethyldistearyl aminochloride or dimethylstearyl aminohydrochloride.
  • the amount of the emulsifier should exceed 0.05% by weight based on the dry fibers, and preferably 0.1 10% by weight based on the dry fibers.
  • the carbamoyl chlorides according to the invention are employed in an amount exceeding 0.001 percent by weight based on the dry fibers by addition to the stock of fibers or by surface sizing of paper.
  • the upper limit is not critical and is only limited by economical considerations.
  • the amount of the carbamoyl chloride should fall within the range of from 0.001 to 5 percent by weight, most preferably 0.005 to 0.5 percent by weight based on the dry fibers.
  • the fiber suspension or the concentrated fibers may also contain other additives commonly used in the manufacturing of paper, paperboard, fiberboard, particle board, etc. such as alum, fillers, pigments, retention agents, foam quentching agents, etc.
  • Unsized paper sheets having a surface weight of about 70 g/m were formed from a bleached sulphate pulp beaten to about SR at a pH of 8.0 in a laboratory sheet machine.
  • the sheets were dried and condi- 10 g of a carbamoyl chloride R R C ,,H were melted at 60C and then g distilled water (60 C) were added during homogenization for 5 minutes.
  • the emulsion was thereupon rapidly cooled to 25C to give a stable dispersion.
  • EXAMPLE 3 10 g of a carbamoyl chloride R R C H and 0.5 g of a stearylamine hydrochloride were melted together at 60C, then 89.5 g of distilled water (60C) were added during homogenization for 5 minutes. The emulsion was rapidly cooled to 25C to give a stable dispersion.
  • EXAMPLE 4 10 g of carbamoyl chloride R R C l-l were melted and then 90.0 g of distilled water (60C) containing 0.5 g ofa water-soluble cationic polyacrylamide -were added during the homogenization for 5 minutes.
  • the emulsion then was rapidly cooled to 25C to give a stable dispersion.
  • the obtained dispersions thereafter were used as sizing agents for paper in the same manner as described in Example 1. The results are shown in the following table: (The Cobb number for unsized paper is 100).
  • a dispersion as defined in example 2 was added to a suspension of cellulose fibers in water together with a cationic polyacrylamide having a molecular weight of more than one million.
  • EXAMPLE 7 A dispersion as defined in example 2 was added to a suspension of cellulose fibers in water together with an anionic polyacrylamide having a molecular weight of more than one million.
  • EXAMPLE 9 In manufacturing of a porous fiberboard 0.20% of methylstearyl carbamoyl chloride were added to the stock based on the dry fiber weight. The board panels were dried for 2 hours at 20C 160C at a continuously elevating temperature. v
  • a process for sizing cellulose fibers or material containing cellulosic fibers wherein the cellulose fibers are brought into contact with at least 0.001% by weight based upon the weight of the dry cellulose fibers of a carbamoyl chloride having a general formula N C R2 Cl wherein R is an organic, hydrophobic hydrocarbon group containing 8-40 carbon atoms and R is selected from the group consisting of hydrogen, lower alkyl and organic, hydrophobic hydrocarbon group containing 8-40 carbon atoms.
  • R is an alkyl group comprising 12-30 carbon atoms and R is selected from the group consisting of hydrogen, lower alkyl, and organic, hydrophobic hydrocarbon group containing 53-40 carbon atoms.
  • R and/or R contain an inert substituent selected from the group of ether, carboalkoxy, alkyloxy, aryloxy, arylalkyloxy, and keto(carbonyl)-tert.amide groups.
  • both R and R are 1a 31- 7.
  • both R and R are 12 2s- 8.
  • said fibers are brought into contact with an aqueous dispersion of said carbamoyl chloride and an emulsifier in an effective emulsifying amount.
  • R2 Cl wherein R is an organic, hydrophobic hydrocarbon group containing 8-40 carbon atoms and R is selected from the group consisting of hydrogen, lower alkyl and organic, hydrophobic hydrocarbon group containing 8-40 carbon atoms, and wherein the amount of said 8 0.5% by weight based upon the weight of dry cellulose fibers.
  • the cellulose fiber or material containing cellulosic fibers of claim 10 which further includes an emulsifier.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Paper (AREA)
US271858A 1971-07-15 1972-07-14 Process for sizing cellulose fibers Expired - Lifetime US3887427A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US05/561,562 US3966484A (en) 1971-07-15 1975-03-24 Composition for sizing cellulose fibers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE09173/71A SE355204B (da) 1971-07-15 1971-07-15
SE12622/71A SE356088B (da) 1971-11-16 1971-11-16

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Application Number Title Priority Date Filing Date
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US (1) US3887427A (da)
JP (1) JPS523006B1 (da)
AT (1) AT319740B (da)
CA (1) CA985462A (da)
CH (1) CH553845A (da)
DE (1) DE2234716C3 (da)
FR (1) FR2145617B1 (da)
GB (1) GB1392746A (da)
IT (1) IT961341B (da)
SE (1) SE355204B (da)
SU (1) SU439998A3 (da)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966484A (en) * 1971-07-15 1976-06-29 Kemanord Aktiebolag Composition for sizing cellulose fibers
US5163931A (en) * 1991-01-02 1992-11-17 Pablo Aldrett Substantially hydrophobic and biodegradable laminar cellulose material, its manufacturing method, and substantially biodegradable disposable diapers made of said material
US5263982A (en) * 1990-03-14 1993-11-23 Ube Industries, Ltd. Hollow fiber membrane type artificial lung
EP0693589A1 (en) 1994-07-20 1996-01-24 Eka Nobel Ab Method of sizing and aqueous sizing dispersion
US5876562A (en) * 1994-12-02 1999-03-02 Eka Chemicals Ab Sizing dispersions
US6093217A (en) * 1997-02-05 2000-07-25 Akzo Nobel N.V. Sizing of paper
US6165259A (en) * 1997-02-05 2000-12-26 Akzo Nobel N.V. Aqueous dispersions of hydrophobic material
US20020096275A1 (en) * 2000-08-07 2002-07-25 Erik Lindgren Sizing dispersion
US20020096290A1 (en) * 2000-08-07 2002-07-25 Erik Lindgren Process for sizing paper
EP1256655A1 (en) * 2001-05-09 2002-11-13 Akzo Nobel N.V. Sizing dispersion
US6485555B1 (en) 1999-04-15 2002-11-26 Akzo Nobel N.V. Sizing composition
US20030127205A1 (en) * 2001-11-19 2003-07-10 Lars Odberg Process for sizing paper and sizing composition
US20090250063A1 (en) * 2006-08-04 2009-10-08 Claude Gaumond Hyperbaric/hypoxic chamber system

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3301670A1 (de) * 1983-01-20 1984-07-26 Bayer Ag, 5090 Leverkusen Leimungsmittel

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1996707A (en) * 1929-06-08 1935-04-02 Alexander Nathansohn Dr Manufacture of paper and the like
US2099363A (en) * 1934-06-21 1937-11-16 Du Pont Textile
US2270658A (en) * 1937-11-15 1942-01-20 North American Rayon Corp Treatment of textile materials
US3238010A (en) * 1959-06-02 1966-03-01 Grace W R & Co Method of reacting cellulose paper and specific non-ionic latices containing hydrogen and hydroxy groups in the polymer chain with polyisocyanate adducts
US3501523A (en) * 1963-06-04 1970-03-17 Upjohn Co Secondary carbamyl chlorides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1996707A (en) * 1929-06-08 1935-04-02 Alexander Nathansohn Dr Manufacture of paper and the like
US2099363A (en) * 1934-06-21 1937-11-16 Du Pont Textile
US2270658A (en) * 1937-11-15 1942-01-20 North American Rayon Corp Treatment of textile materials
US3238010A (en) * 1959-06-02 1966-03-01 Grace W R & Co Method of reacting cellulose paper and specific non-ionic latices containing hydrogen and hydroxy groups in the polymer chain with polyisocyanate adducts
US3501523A (en) * 1963-06-04 1970-03-17 Upjohn Co Secondary carbamyl chlorides

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966484A (en) * 1971-07-15 1976-06-29 Kemanord Aktiebolag Composition for sizing cellulose fibers
US5263982A (en) * 1990-03-14 1993-11-23 Ube Industries, Ltd. Hollow fiber membrane type artificial lung
US5163931A (en) * 1991-01-02 1992-11-17 Pablo Aldrett Substantially hydrophobic and biodegradable laminar cellulose material, its manufacturing method, and substantially biodegradable disposable diapers made of said material
EP0693589A1 (en) 1994-07-20 1996-01-24 Eka Nobel Ab Method of sizing and aqueous sizing dispersion
US5510003A (en) * 1994-07-20 1996-04-23 Eka Nobel Ab Method of sizing and aqueous sizing dispersion
US5876562A (en) * 1994-12-02 1999-03-02 Eka Chemicals Ab Sizing dispersions
US6093217A (en) * 1997-02-05 2000-07-25 Akzo Nobel N.V. Sizing of paper
US6165259A (en) * 1997-02-05 2000-12-26 Akzo Nobel N.V. Aqueous dispersions of hydrophobic material
US6306255B1 (en) 1997-02-05 2001-10-23 Akzo Nobel Nv Sizing of paper
US6485555B1 (en) 1999-04-15 2002-11-26 Akzo Nobel N.V. Sizing composition
US20020096290A1 (en) * 2000-08-07 2002-07-25 Erik Lindgren Process for sizing paper
US20020096275A1 (en) * 2000-08-07 2002-07-25 Erik Lindgren Sizing dispersion
US20040206467A1 (en) * 2000-08-07 2004-10-21 Erik Lindgren Process for sizing paper
US6818100B2 (en) 2000-08-07 2004-11-16 Akzo Nobel N.V. Process for sizing paper
US6846384B2 (en) 2000-08-07 2005-01-25 Akzo Nobel N.V. Process for sizing paper
US7318881B2 (en) 2000-08-07 2008-01-15 Akzo Nobel N.V. Process for sizing paper
US6692560B2 (en) 2001-05-08 2004-02-17 Akzo Nobel N.V. Sizing composition
EP1256655A1 (en) * 2001-05-09 2002-11-13 Akzo Nobel N.V. Sizing dispersion
US20030127205A1 (en) * 2001-11-19 2003-07-10 Lars Odberg Process for sizing paper and sizing composition
US6869471B2 (en) 2001-11-19 2005-03-22 Akzo Nobel N.V. Process for sizing paper and sizing composition
US20090250063A1 (en) * 2006-08-04 2009-10-08 Claude Gaumond Hyperbaric/hypoxic chamber system

Also Published As

Publication number Publication date
AT319740B (de) 1975-01-10
SE355204B (da) 1973-04-09
FR2145617A1 (da) 1973-02-23
DE2234716C3 (de) 1975-05-07
JPS523006B1 (da) 1977-01-25
IT961341B (it) 1973-12-10
CA985462A (en) 1976-03-16
GB1392746A (en) 1975-04-30
SU439998A3 (ru) 1974-08-15
DE2234716A1 (de) 1973-02-01
CH553845A (de) 1974-09-13
DE2234716B2 (de) 1974-09-19
FR2145617B1 (da) 1977-01-14

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