US20110073265A1 - Process chemical for use in the production of paper or board - Google Patents

Process chemical for use in the production of paper or board Download PDF

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Publication number
US20110073265A1
US20110073265A1 US12/599,709 US59970908A US2011073265A1 US 20110073265 A1 US20110073265 A1 US 20110073265A1 US 59970908 A US59970908 A US 59970908A US 2011073265 A1 US2011073265 A1 US 2011073265A1
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process according
paper
fibre suspension
radical polymerization
aqueous fibre
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US12/599,709
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English (en)
Inventor
Rosa Carceller
Ari Juppo
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Kemira Oyj
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Kemira Oyj
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Assigned to KEMIRA OYJ reassignment KEMIRA OYJ ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JUPPO, ARI, CARCELLER, ROSA
Publication of US20110073265A1 publication Critical patent/US20110073265A1/en
Abandoned legal-status Critical Current

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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
    • 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
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • D21H21/06—Paper forming aids
    • D21H21/10—Retention agents or drainage improvers
    • 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
    • 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
    • D21H21/06—Paper forming aids

Definitions

  • the present invention relates process chemicals obtained by controlled radical polymerization technique or by controlled photopolymerization technique. These polymers can be used in the wet end of a paper or board machine in the production of paper or board for improving the runnability and productivity of the paper or board machine. These polymers are especially useful as coagulants or fixatives for the binding of disturbing substances to the fibres in the production of paper or board.
  • U.S. Pat. No. 5,676,796 disclose a process for producing paper comprising forming a thick stock cellulosic suspension, flocculating the thick stock by adding a synthetic water soluble polymeric material, then diluting the flocculated thick stock to form a thin stock, and subsequently adding a coagulant to the thin stock followed by draining to form a sheet.
  • a preferred flocculant polymer is a copolymer of acrylamide and dimethylaminoethyl acrylate quaternised with methyl chloride, and a preferred coagulant polymer is poly diallyl dimethyl ammonium chloride (polyDADMAC).
  • U.S. Pat. No. 5,194,120 discloses a process for producing paper comprising adding a cationic polymer and an amorphous metal silicate material to a furnish followed by introducing the furnish to the headbox of a paper machine.
  • a preferred cationic polymer is a tertiary or quaternary amine derivative of polyacrylamide.
  • U.S. Pat. No. 4,980,025 discloses a process for producing paper comprising adding separately to an aqueous paper pulp a cationic polyacrylamide and a sol comprising anionic colloidal particles, followed by forming and drying the aqueous paper pulp. The process is claimed to improve drainage and retention.
  • EP Patent Publication 1 266 092 B1 discloses a process for producing paper comprising adding retention aids to the stock passing to the paper machine headbox, the stock is directed to the wire, the stock is dewatered to form a paper web, and the paper web is dried.
  • the retention aids comprise a solution of a water-soluble cationic polymer which is a copolymer of acrylamide or methacrylamide and a cationic monomer, and in the form of a suspension, a microparticle mixture containing a swellable clay and a colloidal synthetic metal silicate.
  • the present invention is focussed on a different type of polymers being obtained by controlled radical polymerization or by controlled photopolymerization.
  • a control radical process has characteristics of a living polymerization system in that it is capable of controlling the molecular weight and the molecular weight distribution of the resultant polymer.
  • Free radical polymerization is the most widespread method of polymerization of vinylic monomers. Free radical polymerizations are chain reactions in which every polymer chain grows by addition of a monomer to the terminal free radical reactive site called “active center”. The addition of the monomer to this site induces the transfer of the active center to the newly created chain end. Free radical polymerization is characterized by many attractive features, such as applicability for a wide range of polymerizable groups, as well as tolerance to many solvents, small amount of impurities and many functional groups present in the monomers. However, classical free radical polymerization has some limitations, inherent to its mechanism.
  • NMRP nitroxide-mediated radical polymerization
  • ATRP Atom Transfer Radical Polymerization
  • MADIX Macromolecular Design via Interchange of Xanthates
  • WO 98/58974, WO 00/75207 and WO 01/42312 discloses processes for radical polymerization controlled by control agents of xanthate type.
  • WO 98/01478 discloses a process for radical polymerization controlled by control agents of dithioester type.
  • the produced polymers can be used in the fields of coatings, imaging, electronics, plastics, adhesives and sealants.
  • WO 99/03894 discloses a polymerization in the presence of nitroxide precursors.
  • WO 99/31144 discloses a process for radical polymerization controlled by control agents of dithiocarbamate type.
  • WO 02/26836 discloses a process for radical polymerization controlled by control agents of dithiocarbazate type.
  • WO 02/10223 discloses a process for radical polymerization controlled by control agents of dithiophosphoro ester type.
  • WO 96/30421 disclosed a polymerization process based on atom transfer radical polymerization (ATRP).
  • U.S. Pat. No. 6,812,291 discloses a process for the preparation of block polymers by controlled radical polymerization from dithiocarbamate compounds by thermal initiation.
  • RAFT chain transfer agents Although there are a number of RAFT chain transfer agents, only few of them are water soluble.
  • the present invention preferably uses water soluble chain transfer agents having a specific composition resulting in a polymer having desired properties, such as narrow molecular weight distribution.
  • An object of the invention is to improve the process for producing paper or board by providing an improved process chemical of the above type.
  • polymers obtained by controlled radical polymerization technique from an ethylenically unsaturated monomer, a chain transfer agent, and an initiator in a liquid medium preferably using heat to make radicals or by controlled photopolymerization technique from an ethylenically unsaturated monomer and a photoiniferter in a liquid medium preferably using UV light to make radicals are useful as process chemicals in the wet end of a paper or board machine in the production of paper or board for improving the runnability and productivity of the paper or board machine.
  • the present invention provides a process for producing paper or board from an aqueous fibre suspension, which process comprises adding a process chemical to the aqueous fibre suspension, feeding the obtained aqueous fibre suspension to the headbox of a paper or board machine, feeding the aqueous fibre suspension from the headbox to a wire, dewatering the aqueous fibre suspension on the wire to form a paper or board web, and drying the paper or board web, said process chemical being a polymer obtained by controlled radical polymerization technique from an ethylenically unsaturated monomer, a chain transfer agent, and an initiator in a liquid medium or by controlled photopolymerization technique from an ethylenically unsaturated monomer and a photoiniferter in a liquid medium.
  • Typical ethylenically unsaturated monomers include ⁇ , ⁇ -ethylenically unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, crotonic acid, fumaric acid, citraconic acid, etc.; styrenesulfonic acid, vinylsulfonic acid and the like; salts of these (alkali metal salts, ammonium salts, amine salts, etc.); acid anhydrides such as maleic anhydride, and half esters thereof with straight or branched alcohols; amino group-containing (meth)acrylate such as dimethylaminoethyl meth(acrylate), dimethylaminopropyl (meth)acrylate, diethylaminoethyl (meth)acrylate, ⁇ 2-[(meth)acryloyloxy]ethyl ⁇ trimethylammonium chloride, diallyldimethylammoni
  • Preferred monomers are acrylamide, acrylic acid, dimethyl acrylamide, 2-(dimethylamino)ethyl methacrylate, [2-(acryloyloxy)ethyl]trimethylammonium chloride, 2-(methacryloyloxy)ethyl]trimethylammonium chloride and diallyldimethyl-ammonium chloride.
  • chain transfer agents are compounds having a segment having the formula
  • X is C, O, N or S.
  • Such chain transfer agents are for example S,S′-bis( ⁇ , ⁇ ′-dimethyl- ⁇ ′′-acetic acid) trithiocarbonate, 4-cyanopentanoic acid dithiobenzoate (CPA) and 2-(2-methyl-2-thiobenzoylsulfanylpropionylimino)ethanesulfonate.
  • CPA 4-cyanopentanoic acid dithiobenzoate
  • 2-(2-methyl-2-thiobenzoylsulfanylpropionylimino)ethanesulfonate In order to increase the solubility of the CPA its salts can be used, for example sodium salt.
  • the compounds can thus be utilized to control free radical polymerization to give narrow molecular weight distributions and to control the molecular weight of the polymer.
  • the control means also that block polymers can be made from the previously synthesized homopolymers that have been made according to invention. These homopolymers can be used as chain transfer agent.
  • the molar ratio of the chain transfer agent to monomer is preferably from 0.0005 to 0.025, more preferably from 0.001 to 0.01, and still more preferably from 0.001 to 0.005.
  • the polydispersity index is a measure of the distribution of molecular weights in a polymer and is the weight average molecular weight (M w ) divided by the number average molecular weight (M n ).
  • the PDI is preferably less than 2, more preferably less than 1.7 for the polymers prepared according to the invention.
  • the polymerization of monomers can be made in any suitable solvent of solvent mixture.
  • suitable solvents include water, alcohol (e.g. methanol, ethanol, n-propanol, isopropanol or butanol), ether (e.g. diethyl ether, anisole or tetrahydrofuran), dimethyl sulphoxide, dimethyl formamide, acetone, acetonitrile, hexamethyl-phosphoramide, acetic acid, formic acid, hydrocarbon (e.g. hexane, cyclohexane, benzene or toluene), methylene chloride, chloroform and ethyl acetate.
  • the liquid medium wherein the polymerization is carried out comprises water.
  • the source of free radicals can be any suitable method of generating free radicals such as thermally induced method, redox initiating method, photochemical initiating method or high energy radiation such as electron beam, X— or gamma ray radiation.
  • the initiating system is chosen such that under the reaction conditions, there is no substantial adverse interaction of the initiator, the initiating conditions or the initiating radicals with the transfer agent under the conditions of the procedure.
  • the preferred method of generating free radicals is thermally induced method.
  • thermal initiators are azo compound, peroxides or peroxyesters.
  • the polymerization initiators are not limited to any particular species but may be any of the conventional initiators, inclusive redox initiators, azo initiators and peroxides.
  • the azo initiators are preferred and, as specific examples thereof, there may be mentioned, among others, azonitrile compounds such as 2,2′-azobis(2-methylpropionitrile) (AIBN), azobisdimethyl-valero-nitrile and azobisdimethylmethoxyvaleronitrile; azoamidine compounds such as 2,2′-azobis(methylpropionamidine)dihydrochloride (V-50), VA-041, VA-044 and VA-061 (V-50, VA-041, VA-044 and VA-061 are products of Wako Pure Chemical Industries, Ltd.); azoamide compounds such as VA-080, VA-086 and VA-088 (products of Wako Pure Chemical Industries, Ltd.); azoalkyl compounds such as azodi-tert-octane and azoditert-butane; cyanopropylazo-formamide, 4,4′-azobis(cyanovaleric acid), 4,4′-azobis(cyanopentanoic acid
  • One of these radical polymerization initiators for use in the present invention may be used alone, or two or more thereof may be used as a mixture.
  • the molar ratio of the radical polymerization initiator to the monomer is preferably from 0.0001 to 0.1, more preferably from 0.0005 to 0.05, still more preferably from 0.0005 to 0.01.
  • the polymerization process according to the present invention is performed under the conditions typical of conventional free-radical polymerization. Polymerizations are suitably carried out at temperatures in the range of 0-150° C., preferably 20-120° C., more preferably 60-90° C.
  • the pH can vary from 1 to 9, preferably from 4 to 7. Buffer solutions can also be used, especially in the polymerization of acrylamide.
  • preferred photoiniferters are compounds having a segment having the formula
  • Such photoiniferters are for example 2-(N,N-diethyldithiocarbamyl)isobutyric acid (DTCA) and 2-(N,N-dimethyldithiocarbamyl)isobutyric acid.
  • DTCA 2-(N,N-diethyldithiocarbamyl)isobutyric acid
  • 2-(N,N-dimethyldithiocarbamyl)isobutyric acid In order to increase the solubility of the photoiniferter its salts cand be used, for example sodium salt.
  • the compounds can thus be utilized to control photo polymerization to give narrow molecular weight distributions and to control the molecular weight of the polymer.
  • the control means also that block polymers can be made from the previously synthesized homopolymers that have been made according to invention. These homopolymers can be used as chain transfer agent. These compounds can be used as initiators and chain transfer agent.
  • the molar ratio of the photoiniferter to the monomer is preferably from 0.0001 to 0.1, more preferably from 0.0005 to 0.05, still more preferably from 0.001 to 0.01.
  • the polymerization process according to the present invention is performed under the conditions typical of conventional photopolymerization.
  • the radicals are preferably generated by UV irradiation.
  • the UV intensities and radiation distances are the same as for conventional photopolymerization, for example 1000-4000 ⁇ W/cm 2 and 10-20 cm.
  • Polymerizations are suitably carried out at temperatures in the range of 5-90° C., preferably 20-70° C., more preferably 20-50° C.
  • the polymers of the invention can be homopolymers or copolymers.
  • the copolymers can be block copolymers or multiblock copolymers, e.g. diblock, triblock copolymers.
  • the polymers of the invention to be used as process chemicals in the production of paper or board are cationic. It should, however, be understood that monomers or homopolymers used for building up cationic block copolymers can be anionic.
  • Block copolymer can be made from a homopolymer that has been made according this invention.
  • the homopolymer works as a chain transfer agent and is called here macro-CTA (macro-chain transfer agent).
  • macro-CTA macro-chain transfer agent
  • the homopolymer works as a macro-photoiniferter.
  • the block copolymers can be made in similar process conditions as making homopolymers.
  • the polymers typically have a molecular weight (M w ) in the range of about 1000 to about 1 000 000. More preferably in the range of about 10 000 to about 400 000 still more preferably in the range of about 10 000 to 100 000.
  • the polymer is preferably added to the aqueous fibre suspension in an amount of about 25 to 10 000 g/ton, more preferably about 50 to 1 000 g/ton of dry matter of the aqueous fibre suspension.
  • the process chemical can function as a coagulant or fixative for the binding of disturbing substances to the fibres.
  • chemicals conventionally used in paper and board manufacture such as fillers and/or functional additives, can be added to the aqueous fibre suspension prior to the headbox.
  • Such chemicals and the adequate amounts thereof are well-known to the man skilled in the art.
  • the aqueous fibre suspension to be treated by the invention can comprise a chemical pulp, mechanical pulp, chemo-mechanical pulp, recycled fibres or a mixture thereof.
  • the invention also relates to the use of a polymer obtained by controlled radical polymerization technique from an ethylenically unsaturated monomer, a chain transfer agent, and an initiator in a liquid medium, as a process chemical in the wet end of a paper or board machine in the production of paper or board for improving the runnability and productivity of the paper or board machine.
  • the polymers are as described above.
  • the invention relates to the use of a polymer obtained by controlled photopolymerization technique from an ethylenically unsaturated monomer and a photoiniferter in a liquid medium, as a process chemical in the wet end of a paper or board machine in the production of paper or board for improving the runnability and productivity of the paper or board machine.
  • the polymers are as described above.
  • the reaction was stopped after 24 h by injecting inhibitor to the reaction solution, and cooling the reaction solution to the room temperature.
  • the poly[2-(methacryloxy)ethyl]trimethylammonium chloride]homopolymer was precipitated in acetone-ethanol (1:1) solution, dissolved in water and then dialyzed against water for 24 hours, and then freeze dried.
  • Mw by GPC was 16 500 g/mol and the PDI was 1.52.
  • the reaction was stopped by injecting inhibitor (hydroquinone) to the reaction solution, opening the flask and cooling the reaction solution to the room temperature.
  • inhibitor hydroquinone
  • the product was precipitated in acetone, dissolved in water and then dialyzed against water for 24 hours, and then freeze dried.
  • the product was yellow.
  • the weight average molecular weight determined by GPC-measurement was 57 000 g/mol.
  • the crude product was purified by silica column chromatography, eluting with 3:1 dichloromethane/hexane to yield 2-(N,N-diethyldithiocarbamyl)isobutyric acid as a white powder.
  • the yield was 95%.
  • Photopolymerization of 8 g of 75% solution of [2-(methacryloyloxy)ethyl]trimethyl-ammonium chloride was carried out in 18 g of water initiated by 0.06 g of 2-(N,N-diethyldithiocarbamyl)isobutyric acid that was dissolved in 1 ml of methanol and neutralized with an equivalent molar amount of NaOH, at 35° C. with UV irradiation time of 2 hours. After polymerization the polymer was recovered by precipitation with acetone.
  • Photopolymerization of 12 g of 50% water solution of acrylamide was carried out in 14 g water initiated by 0.06 g 2-(N,N-diethyldithiocarbamyl)isobutyric acid dissolved in 1 ml methanol neutralized with an equivalent molar amount of NaOH, and one drop diethylenetriaminepentaacetic acid, at 35° C. water bath with UV irradiation time of 2 hours. After polymerization the homopolymer was recovered by precipitation.
  • Photopolymerization of 2.7 g of 75% solution of [2-(methacryloyloxy)ethyl]-trimethylammonium chloride was carried out in 9.3 g water, initiated by 0.2 g of homopolymer from the previous step (macrophotoiniferter) at 35° C. and under UV irradiation for 2 h. After polymerization the ⁇ poly(acrylamide) ⁇ - ⁇ poly[2-(methacryloyloxy)ethyl]trimethylammonium chloride ⁇ was recovered by precipitation with acetone.
  • the purpose of the tests was to investigate the action of the polymers of the present invention as fixatives for TMP pulp.
  • the polymers of examples 1, 2 and 5 were used.
  • the pulp was a mixture comprising 80% of thermo mechanical pulp (TMP) and 20% of chemical softwood pulp.
  • each fixative polymer was 0, 50, 100, 200 and 400 g per ton of dry matter of the aqueous fibre suspension.
  • the test results are shown in following Table 1.
  • Example 13 A second test was made as described in Example 13. The polymer of Example 5 was tested. The dose of the fixative polymers as dry substance was 100 g per ton of dry matter of the aqueous fibre suspension. The test results are shown in following Table 2.
  • Example 13 A third test was made as described in Example 13.
  • the polymer of Example 6 was tested.
  • the dose of the fixative polymers as dry substance was 800 g per ton of dry matter of the aqueous fibre suspension.
  • the test results are shown in following Table 3.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
US12/599,709 2007-05-21 2008-05-21 Process chemical for use in the production of paper or board Abandoned US20110073265A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FI20070392 2007-05-21
FI20070392A FI122734B (fi) 2007-05-21 2007-05-21 Prosessikemikaali käytettäväksi paperin tai kartongin valmistuksessa
PCT/FI2008/050293 WO2008142209A1 (en) 2007-05-21 2008-05-21 Process chemical for use in the production of paper or board

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US (1) US20110073265A1 (pl)
EP (1) EP2147152B1 (pl)
FI (1) FI122734B (pl)
PL (1) PL2147152T3 (pl)
WO (1) WO2008142209A1 (pl)

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JP5937549B2 (ja) * 2012-08-31 2016-06-22 ダウ グローバル テクノロジーズ エルエルシー 光酸発生剤化合物、光酸発生剤化合物を含有する末端基を含むポリマー、および製造方法

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EP2147152A1 (en) 2010-01-27
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FI20070392A0 (fi) 2007-05-21
WO2008142209A1 (en) 2008-11-27
PL2147152T3 (pl) 2013-12-31
FI20070392A (fi) 2008-11-22

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