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US20020069989A1 - Bonding of paper using latex-dispersions of copolymers made of hydrophobic monomers/polymers of styrene/maleic anhydride type of low molecular mass - Google Patents

Bonding of paper using latex-dispersions of copolymers made of hydrophobic monomers/polymers of styrene/maleic anhydride type of low molecular mass Download PDF

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Publication number
US20020069989A1
US20020069989A1 US08/867,418 US86741897A US2002069989A1 US 20020069989 A1 US20020069989 A1 US 20020069989A1 US 86741897 A US86741897 A US 86741897A US 2002069989 A1 US2002069989 A1 US 2002069989A1
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US
United States
Prior art keywords
latex
dispersions
paper
styrene
meth
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
Application number
US08/867,418
Inventor
Bruno Feret
Isabelle Betremieux
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Original Assignee
Elf Atochem SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Elf Atochem SA filed Critical Elf Atochem SA
Assigned to ELF ATOCHEM S.A. reassignment ELF ATOCHEM S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BETREMIEUX, ISABELLE, FERET, BRUNO
Publication of US20020069989A1 publication Critical patent/US20020069989A1/en
Abandoned legal-status Critical Current

Links

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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon 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
    • D21H21/14—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
    • D21H21/16—Sizing or water-repelling agents
    • 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
    • D21H11/14—Secondary 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
    • 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
    • D21H17/35—Polyalkenes, e.g. polystyrene
    • 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
    • D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates

Definitions

  • the present invention relates to the surface treatment of printing and writing papers or wrapping papers.
  • the invention is thus the application of latex-dispersions, such as those resulting from the polymerization of a mixture of hydrophobic monomers composed of styrene and of (meth)acrylic esters in emulsion in an aqueous solution of a water-soluble or water-dispersible amphiphilic copolymer consisting of a combination of hydrophobic monomers and hydrophilic monomers bearing carboxylic acid functions, in the presence of a radical initiator, in which the said amphiphilic copolymer has a molecular mass of between 500 and 5,000, to the bonding of printing and writing papers and wrapping papers, and more particularly to such papers obtained from recycled pulps.
  • latex-dispersions such as those resulting from the polymerization of a mixture of hydrophobic monomers composed of styrene and of (meth)acrylic esters in emulsion in an aqueous solution of a water-soluble or water-dispersible amphiphilic copolymer consisting of a combination
  • the copolymer with a molecular mass of between 500 and 5,000 is preferably a copolymer of one or more hydrophobic monomers taken from the group consisting of styrene or derivatives thereof, isobutylene or derivatives thereof and (meth)acrylic esters and of one or more hydrophilic monomers taken from the group consisting of (meth)acrylic acid and maleic anhydride, it being possible for the latter to be partially modified with an alcohol or an amine while at the same time remaining water-soluble or water-dispersible in aqueous medium, in particular a copolymer of styrene and of maleic anhydride in which the anhydride part may or may not be modified with an alcohol or an amine and in which the acid number is between 150 and 500.
  • the polymerized hydrophobic monomers in emulsion in the aqueous solution of the amphiphilic copolymer are monomers of the group consisting of styrene and derivatives thereof, (meth)acrylic esters, including fluoro(meth)acrylic esters resulting from the esterification of (meth)acrylic acid with a perfluoro alcohol, or a mixture of these monomers.
  • latex-dispersions according to the invention may also be appreciated in the treatment of packaging cartons made from recycled pulps, for which a certain level of water-resistance is sought.
  • 1,269 g of an oligomer with a molecular mass equal to 1,900, consisting of 74.3% by mass of styrene and 25.7% by mass of maleic anhydride, 6,825 g of demineralized water and 500 g of 28% aqueous ammonia are introduced in order into a 20 liter three-necked glass reactor fitted with a mechanical stirrer.
  • the reaction mixture is heated to 60° C. and kept stirring until the oligomer has dissolved.
  • the solution is brought to 85° C.
  • This example shows the advantage of the bonding agents according to the invention for the surface treatment of printing and writing papers as regards their water-resistance.
  • the quality of the final bonding is evaluated by the COBB test which is well known to those skilled in the art, and is carried out according to NF standard EN 20535-ISO 535.
  • the COBB test is performed here with a contact time of 60 seconds.
  • the treatment is carried out using a laboratory size press on two types of paper, one of them having a weight per unit area of 70 g/m 2 , without internal bonding, and the other of 90 g/m 2 , which may or may not have undergone internal bonding with alkylketene dimer (Aquapel® 315 from Hercules, referred to herein below as AKD).
  • the two papers are manufactured from a fresh chemical pulp.
  • composition being made up to 100% by adding the required remainder of deionized water for this purpose.
  • the latex-dispersion according to the invention is that which has been described in Example 1.
  • the comparative product according to the prior art is the dispersion of Example 7 of U.S. Pat. No. DE 2,548,393.
  • the paper is manufactured with no internal bonding agent, either from a de-inked mechanical pulp or with a recycled pulp.
  • the treatment was carried out on a pilot paper machine with three rates of introduction equivalent to a deposition of surface bonding agents—those of the above example—of 9, 12 and 15 kg/tonne of paper for the first support and of 3, 6 and 12 kg/t. for the second.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
  • Polymerisation Methods In General (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Such latex-dispersions used in paper bonding formulations make it possible to obtain acceptable COBB values, even with printing and writing papers or wrapping papers obtained from recycled or de-inked mechanical pulps.

Description

  • The present invention relates to the surface treatment of printing and writing papers or wrapping papers. [0001]
  • It is known to use, for surface bonding of paper, printing agents consisting of latex dispersions made by polymerization or copolymerization of hydrophobic monomers in an aqueous solution of water-soluble or water-dispersible anionic polymers, in particular styrene/maleic anhydride copolymers, as taught by German patent DE 25 48393. These products were satisfactory, at least when the papers were made from fresh pulps. With mechanical pulps or pulps which are 100% recycled or simply partially recycled, it becomes very difficult, or even impossible, to obtain papers with satisfactory wet strength. This phenomenon, which can already be seen for “printing and writing” papers, becomes a major problem for wrapping papers. [0002]
  • It has just been found that bonding compositions based on latexes which are based on low-molecular-weight styrene/maleic anhydride copolymers provide an unexpected solution to the problem. [0003]
  • The invention is thus the application of latex-dispersions, such as those resulting from the polymerization of a mixture of hydrophobic monomers composed of styrene and of (meth)acrylic esters in emulsion in an aqueous solution of a water-soluble or water-dispersible amphiphilic copolymer consisting of a combination of hydrophobic monomers and hydrophilic monomers bearing carboxylic acid functions, in the presence of a radical initiator, in which the said amphiphilic copolymer has a molecular mass of between 500 and 5,000, to the bonding of printing and writing papers and wrapping papers, and more particularly to such papers obtained from recycled pulps. In the latex-dispersion, the copolymer with a molecular mass of between 500 and 5,000 is preferably a copolymer of one or more hydrophobic monomers taken from the group consisting of styrene or derivatives thereof, isobutylene or derivatives thereof and (meth)acrylic esters and of one or more hydrophilic monomers taken from the group consisting of (meth)acrylic acid and maleic anhydride, it being possible for the latter to be partially modified with an alcohol or an amine while at the same time remaining water-soluble or water-dispersible in aqueous medium, in particular a copolymer of styrene and of maleic anhydride in which the anhydride part may or may not be modified with an alcohol or an amine and in which the acid number is between 150 and 500. The polymerized hydrophobic monomers in emulsion in the aqueous solution of the amphiphilic copolymer are monomers of the group consisting of styrene and derivatives thereof, (meth)acrylic esters, including fluoro(meth)acrylic esters resulting from the esterification of (meth)acrylic acid with a perfluoro alcohol, or a mixture of these monomers. [0004]
  • The use of the latex-dispersions according to the invention may also be appreciated in the treatment of packaging cartons made from recycled pulps, for which a certain level of water-resistance is sought.[0005]
    • EXAMPLES Example 1
  • Preparation of a Latex According to the Invention. [0006]
  • 1,269 g of an oligomer with a molecular mass equal to 1,900, consisting of 74.3% by mass of styrene and 25.7% by mass of maleic anhydride, 6,825 g of demineralized water and 500 g of 28% aqueous ammonia are introduced in order into a 20 liter three-necked glass reactor fitted with a mechanical stirrer. The reaction mixture is heated to 60° C. and kept stirring until the oligomer has dissolved. The solution is brought to 85° C. and a mixture of 1,374 g of styrene and 1,587 g of butyl acrylate is then added under nitrogen with stirring, along with a solution of 52.9 g of (NH[0007] 4)2S2O8 in 1,057 g of water, this being carried out continuously for two hours using pumps for metering out the oligomer solution prepared above, at 85° C. The reaction medium is maintained at 85° C. for a further 2 hours and is then cooled with gentle stirring.
  • A latex whose characteristics are as below is obtained: [0008]
  • Solids=23.5% [0009]
  • Brookfield viscosity at 23° C.=20 mpa.s [0010]
  • pH=8.85 [0011]
  • Average particle diameter=55 nm [0012]
    • Example 2
  • This example shows the advantage of the bonding agents according to the invention for the surface treatment of printing and writing papers as regards their water-resistance. [0013]
  • The quality of the final bonding is evaluated by the COBB test which is well known to those skilled in the art, and is carried out according to NF standard EN 20535-ISO 535. The COBB test is performed here with a contact time of 60 seconds. [0014]
  • The treatment is carried out using a laboratory size press on two types of paper, one of them having a weight per unit area of 70 g/m[0015] 2, without internal bonding, and the other of 90 g/m2, which may or may not have undergone internal bonding with alkylketene dimer (Aquapel® 315 from Hercules, referred to herein below as AKD). The two papers are manufactured from a fresh chemical pulp.
  • The test reports the results of the bonding obtained with aqueous compositions containing: [0016]
  • 5% by weight of AMYLIS® 100 P (Roquette) anionic starch, [0017]
  • 2.5%, 5% or 10%, by weight of active material, of latex-dispersion, [0018]
  • the composition being made up to 100% by adding the required remainder of deionized water for this purpose. [0019]
  • The latex-dispersion according to the invention is that which has been described in Example 1. The comparative product according to the prior art is the dispersion of Example 7 of U.S. Pat. No. DE 2,548,393. [0020]
  • The following were obtained on a paper which was not internally bonded: [0021]
    COBB 60 COBB 60 COBB 60
    Product at 2.5% at 5% at 10%
    According to the >100    90 35
    invention
    According to the >100 >100 55
    prior art
  • The following were obtained on a paper which was internally bonded with AKD [0022]
    COBB 60 COBB 60 COBB 60
    Product at 2.5% at 5% at 10%
    According to the 36 35 28
    invention
    According to the 49 40 33
    prior art
  • It is estimated that an acceptable printing and writing paper should have a COBB 60 of less than 30-40. On this basis, it is easy to see the undeniable advantage of the latex-dispersions of the invention over those of the prior art. [0023]
    • Example 3
  • In this example, the paper is manufactured with no internal bonding agent, either from a de-inked mechanical pulp or with a recycled pulp. The treatment was carried out on a pilot paper machine with three rates of introduction equivalent to a deposition of surface bonding agents—those of the above example—of 9, 12 and 15 kg/tonne of paper for the first support and of 3, 6 and 12 kg/t. for the second. [0024]
  • The following were obtained on a de-inked mechanical pulp [0025]
    COBB 60 COBB 60 COBB 60
    Product at 9 kg/t. at 12 kg/t. at 15 kg/t.
    According to  81 46 28
    the invention
    According to 123 98 78
    the prior art
  • The following were obtained on a 100% recycled pulp [0026]
    COBB 60 COBB 60 COBB 60
    Product at 3 kg/t. at 6 kg/t. at 12 kg/t.
    According to 140 120  25
    the invention
    According to 145 120 100
    the prior art
  • These results show that the bonding agent of the invention gives a sufficient bonding for deposition rates of 12 to 15 kg/t. whereas the comparative product does not make it possible to approach a satisfactory level of bonding at this rate of use. [0027]

Claims (7)

1. Application of latex-dispersions, such as those resulting from the polymerization of a mixture of hydrophobic monomers composed of styrene and of (meth)acrylic esters in emulsion in an aqueous solution of a water-soluble or water-dispersible amphiphilic copolymer consisting of a combination of hydrophobic monomers and hydrophilic monomers bearing carboxylic acid functions, in the presence of a radical initiator, in which the said amphiphilic copolymer has a molecular mass of between 500 and 5,000, to the bonding of papers.
2. Application of latex-dispersions according to claim 1, characterized in that, in the latex-dispersions, the copolymer with a molecular mass of between 500 and 5,000 is a copolymer of one or more hydrophobic monomers taken from the group consisting of styrene or derivatives thereof, isobutylene or derivatives thereof and (meth)acrylic esters and of one or more hydrophilic monomers taken from the group consisting of (meth)acrylic acid and maleic anhydride, it being possible for the latter to be partially modified with an alcohol or an amine while at the same time remaining water-soluble or water-dispersible in aqueous medium.
3. Application of latex-dispersions according to claim 1, characterized in that, in the latex-dispersions, the copolymer with a molecular mass of between 500 and 5,000 is a copolymer of styrene and of maleic anhydride in which the anhydride part may or may not be modified with an alcohol or an amine and in which the acid number is between 150 and 500.
4. Application of latex-dispersions according to claim 1, characterized in that, in the latex-dispersions, the hydrophobic monomers are taken from the group consisting of styrene and derivatives thereof, (meth)acrylic esters, including fluoro(meth)acrylic esters resulting from the esterification of (meth)acrylic acid with a perfluoro alcohol, or a mixture of these monomers.
5. Application according to any one of claims 1 to 4, in which the paper is a printing and writing paper.
6. Application according to any one of claims 1 to 4, in which the paper is a wrapping paper.
7. Application according to any one of claims 1 to 4, in which the paper is a wrapping paper made from a de-inked mechanical pulp or from a recycled pulp.
US08/867,418 1996-05-31 1997-06-02 Bonding of paper using latex-dispersions of copolymers made of hydrophobic monomers/polymers of styrene/maleic anhydride type of low molecular mass Abandoned US20020069989A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR96-06737 1996-05-31
FR9606737A FR2749328B1 (en) 1996-05-31 1996-05-31 ADHESIVE PAPER USING LATEX DISPERSIONS OF HYDROPHOBIC MONOMERIC COPOLYMERS / LOW MOLECULAR MASS STYRENE-MALE ANHYDRIDE POLYMERS

Publications (1)

Publication Number Publication Date
US20020069989A1 true US20020069989A1 (en) 2002-06-13

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Country Status (11)

Country Link
US (1) US20020069989A1 (en)
EP (1) EP0810323B1 (en)
JP (1) JP3484044B2 (en)
KR (1) KR100235071B1 (en)
AR (1) AR007347A1 (en)
AT (1) ATE253141T1 (en)
BR (1) BR9703416A (en)
CA (1) CA2208042C (en)
DE (1) DE69725779T2 (en)
FR (1) FR2749328B1 (en)
NO (1) NO321703B1 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040065425A1 (en) * 2002-10-07 2004-04-08 Kemira Chemicals, Inc. Latex paper sizing composition
WO2005061796A3 (en) * 2003-12-23 2005-09-09 Ciba Sc Holding Ag Chemical improvement in paper making
US20090255641A1 (en) * 2005-12-01 2009-10-15 Helsinki University Of Technology Method of Modifying the Printing Surface of Paper or Board
US20100249281A1 (en) * 2007-07-02 2010-09-30 Manuel Hidalgo Use of grafted sma copolymers in liquid compositions
US20100273965A1 (en) * 2007-12-24 2010-10-28 Arkema France Polymeric additives obtained by salification of copolymers
US20120050392A1 (en) * 2009-05-11 2012-03-01 Sami Puttonen Use of composition for improving inkjet printing properties and an inkjet recording sheet
US8242207B2 (en) 2007-02-07 2012-08-14 Arkema France Styrene/anhydride polymeric material and graft having enhanced properties
AU2008272104B2 (en) * 2007-07-03 2013-05-30 Unicharm Corporation Individual package of absorbent article, wrapping sheet, and method of manufacturing wrapping sheet
WO2013154414A1 (en) 2012-04-13 2013-10-17 Sigma Alimentos, S. A. De C. V. Hydrophobic paper or cardboard with self-assembled nanoparticles and method for the production thereof
WO2016144799A1 (en) * 2015-03-06 2016-09-15 Basf Se Barrier compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2795076B1 (en) 1999-06-21 2001-08-10 Atofina HYDROPHOBIC CATIONIC DISPERSIONS STABILIZED BY MALEIMIDE COPOLYMERS OF LOW MOLECULAR MASS FOR PAPER SIZING
KR102416255B1 (en) * 2022-04-28 2022-07-05 주식회사 영인테크놀로지 Method for manufacturing pulp molded products with high cohesive strength and pulp molded products manufactured thereby

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DE3939034A1 (en) * 1989-11-25 1991-05-29 Henkel Kgaa PRODUCTION OF STABLE POLYMER DISPERSIONS BY MEANS OF AMPHOTER POLYMERS AS STABILIZERS
US5002982A (en) * 1990-02-26 1991-03-26 Gencorp Inc. Paper felts or mats
BR9104402A (en) * 1991-10-10 1993-04-20 Glasurit Do Brasil Limitada WATER DILUTABLE EMULSION POLYMER, PROCESS FOR THE PREPARATION OF A WATER DILUTABLE EMULSION POLYMER, WATER COATING COMPOSITION AND POLYMER USE
MX9306802A (en) * 1992-11-04 1994-05-31 Henkel Corp LATEX FOR HEAT RESISTANT INKS.
JP2670953B2 (en) * 1992-12-07 1997-10-29 昭和高分子株式会社 Method for producing emulsion having super water resistance
GB9408725D0 (en) * 1994-05-03 1994-06-22 Zeneca Resins Bv Production of aqueous polymer compositions

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040065425A1 (en) * 2002-10-07 2004-04-08 Kemira Chemicals, Inc. Latex paper sizing composition
WO2004033791A1 (en) * 2002-10-07 2004-04-22 Kemira Chemicals, Inc. Latex paper sizing composition
US20060076117A1 (en) * 2002-10-07 2006-04-13 Boardman Delos E Latex paper sizing composition
WO2005061796A3 (en) * 2003-12-23 2005-09-09 Ciba Sc Holding Ag Chemical improvement in paper making
US20070107865A1 (en) * 2003-12-23 2007-05-17 Anna-Liisa Tammi Chemical improvement in paper making
US20090255641A1 (en) * 2005-12-01 2009-10-15 Helsinki University Of Technology Method of Modifying the Printing Surface of Paper or Board
US8613830B2 (en) * 2005-12-01 2013-12-24 Helsinki University Of Technology Method of modifying the printing surface of paper or board
US8242207B2 (en) 2007-02-07 2012-08-14 Arkema France Styrene/anhydride polymeric material and graft having enhanced properties
US8609765B2 (en) 2007-02-07 2013-12-17 Arkema France Styrene/anhydride polymeric material and graft having enhanced properties
US20100249281A1 (en) * 2007-07-02 2010-09-30 Manuel Hidalgo Use of grafted sma copolymers in liquid compositions
US8133944B2 (en) 2007-07-02 2012-03-13 Arkema France Use of grafted SMA copolymers in liquid compositions
AU2008272104B2 (en) * 2007-07-03 2013-05-30 Unicharm Corporation Individual package of absorbent article, wrapping sheet, and method of manufacturing wrapping sheet
AU2008272104B9 (en) * 2007-07-03 2013-06-20 Unicharm Corporation Individual package of absorbent article, wrapping sheet, and method of manufacturing wrapping sheet
US20100273965A1 (en) * 2007-12-24 2010-10-28 Arkema France Polymeric additives obtained by salification of copolymers
US8492495B2 (en) 2007-12-24 2013-07-23 Arkema France Polymeric additives obtained by salification of copolymers
US20120050392A1 (en) * 2009-05-11 2012-03-01 Sami Puttonen Use of composition for improving inkjet printing properties and an inkjet recording sheet
WO2013154414A1 (en) 2012-04-13 2013-10-17 Sigma Alimentos, S. A. De C. V. Hydrophobic paper or cardboard with self-assembled nanoparticles and method for the production thereof
US9783930B2 (en) * 2012-04-13 2017-10-10 Sigmaq Alimentos, S.A. De C.V. Hydrophobic paper or cardboard with self-assembled nanoparticles and method for the production thereof
WO2016144799A1 (en) * 2015-03-06 2016-09-15 Basf Se Barrier compositions
CN107567485A (en) * 2015-03-06 2018-01-09 巴斯夫欧洲公司 Barrier compositions
US10422081B2 (en) 2015-03-06 2019-09-24 Basf Se Barrier compositions

Also Published As

Publication number Publication date
NO972474D0 (en) 1997-05-30
EP0810323A3 (en) 1997-12-10
EP0810323B1 (en) 2003-10-29
CA2208042A1 (en) 1997-11-30
JPH1053995A (en) 1998-02-24
KR100235071B1 (en) 1999-12-15
NO321703B1 (en) 2006-06-26
FR2749328A1 (en) 1997-12-05
FR2749328B1 (en) 1998-07-17
NO972474L (en) 1997-12-01
DE69725779T2 (en) 2004-08-05
AR007347A1 (en) 1999-10-27
CA2208042C (en) 2001-07-10
DE69725779D1 (en) 2003-12-04
ATE253141T1 (en) 2003-11-15
KR970075103A (en) 1997-12-10
EP0810323A2 (en) 1997-12-03
BR9703416A (en) 1998-09-15
JP3484044B2 (en) 2004-01-06

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