WO2022080464A1 - 耐油剤および耐油組成物 - Google Patents
耐油剤および耐油組成物 Download PDFInfo
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- WO2022080464A1 WO2022080464A1 PCT/JP2021/038108 JP2021038108W WO2022080464A1 WO 2022080464 A1 WO2022080464 A1 WO 2022080464A1 JP 2021038108 W JP2021038108 W JP 2021038108W WO 2022080464 A1 WO2022080464 A1 WO 2022080464A1
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- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
- D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
- D21H17/24—Polysaccharides
-
- 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
- D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
- D21H17/24—Polysaccharides
- D21H17/28—Starch
-
- 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
- D21H17/36—Polyalkenyalcohols; Polyalkenylethers; Polyalkenylesters
-
- 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
- D21H17/71—Mixtures of material ; Pulp or paper comprising several different materials not incorporated by special processes
- D21H17/72—Mixtures of material ; Pulp or paper comprising several different materials not incorporated by special processes of organic material
-
- 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
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/12—Coatings without pigments applied as a solution using water as the only solvent, e.g. in the presence of acid or alkaline 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
- D21H21/14—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
-
- 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
- D21H27/10—Packing paper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
- B65D65/38—Packaging materials of special type or form
- B65D65/42—Applications of coated or impregnated materials
Definitions
- This disclosure relates to an oil resistant agent and an oil resistant composition.
- Food packaging materials and food containers made of paper are required to prevent the moisture and oil content of food from seeping out. Therefore, the oil resistant agent is applied to the paper either internally or externally.
- Patent Document 1 Japanese Unexamined Patent Publication No. 2004-238518 discloses that a paint containing starch having a total solid content of 12.5 to 100% by weight is applied to a paper substrate to produce starch-processed paper. ing.
- An object of the present disclosure is to provide an oil resistant agent and an oil resistant composition capable of imparting excellent oil resistance to paper.
- the present disclosure relates to an oil resistant agent for paper containing a polysaccharide (preferably a combination of two or more kinds of polysaccharides). Further, the present disclosure also relates to a treatment liquid having a viscosity of 200 cps or less, which is a mixture of an oil resistant agent for paper and water.
- the viscosity is a viscosity at a temperature of 50 ° C., preferably 150 cps or less, 100 cps or less, or 80 cps or less. The lower limit of the viscosity may be 1 cps.
- the present disclosure relates to oil resistant compositions comprising polysaccharides and oil resistant polymers.
- the oil-resistant agent and oil-resistant composition for paper may also contain water and / or an organic solvent, preferably a liquid medium which is water or a mixture of water and an organic solvent (aqueous medium).
- the present disclosure provides oil resistant paper treated with an oil resistant agent or composition for paper. Paper processing is external or internal.
- the oil-resistant paper has an oil-resistant layer containing an oil-resistant agent for paper or an oil-resistant composition depending on the external addition treatment method.
- the oil-resistant paper contains an oil-resistant agent for paper or an oil-resistant composition inside the paper depending on the internal addition treatment method.
- Aspect 1 An oil-resistant composition comprising (1) a polysaccharide and (2) an oil-resistant polymer.
- Aspect 2 The oil resistant polymer (2) Non-fluorine having (a) a repeating unit formed of an acrylic monomer having a long-chain hydrocarbon group having 7 to 40 carbon atoms and (b) a repeating unit formed of an acrylic monomer having a hydrophilic group. It is a copolymer and The oil-resistant composition according to embodiment 1, wherein the weight ratio of the polysaccharide to the oil-resistant polymer is 10: 90 to 98: 2.
- R 1 is a hydrocarbon group having 7 to 40 carbon atoms independently.
- X 1 is a hydrogen atom, a monovalent organic group or a halogen atom.
- k is 1 to 3.
- the oil-resistant composition according to Aspect 2 which is a monomer represented by.
- X 2 is a hydrogen atom, a monovalent organic group or a halogen atom.
- Y 2 is -O- or -NH-.
- R 3 are each independently a hydrocarbon group having 7 to 40 carbon atoms.
- X 3 is a hydrogen atom, a monovalent organic group or a halogen atom.
- n 1 or 2.
- n is an integer from 1 to 90.
- Aspect 5 The oil-resistant composition according to any one of aspects 1 to 4, further comprising water or a liquid medium which is a mixture of water and an organic solvent.
- Aspect 6 An oil resistant agent for paper containing a combination of two or more kinds of polysaccharides.
- At least one polysaccharide is a modified starch or at least one selected from the group consisting of hydroxyalkylated starch, oxidized starch, alkenyl succinate esterified starch, dextrin, cationized starch and pregelatinized starch.
- Aspect 8 A treatment liquid formed from the oil-resistant composition according to any one of aspects 1 to 5 or the oil-resistant agent for paper according to aspects 6 or 7 and water, and having a viscosity of 200 cps or less.
- Aspect 9 The treatment liquid according to embodiment 8, which is used to form an oil resistant layer.
- Aspect 10 The treatment liquid according to Aspect 8 or 9, wherein the amount of the polysaccharide in the treatment liquid is 5% by weight or more.
- Aspect 11 The treatment liquid according to any one of aspects 8 to 10, which also contains an additive.
- Aspect 12 The treatment liquid according to embodiment 11, wherein the additive is at least one selected from polyvinyl alcohol and glucose.
- Aspect 13 An oil-resistant paper having an oil-resistant layer formed from the oil-resistant composition according to any one of aspects 1 to 5 or the oil-resistant agent for paper according to aspects 6 or 7 on the surface of the paper.
- Aspect 14 The oil-resistant paper according to aspect 13, which is a food packaging material or a food container.
- Aspect 15 A method for treating paper by treating the paper with the oil-resistant composition according to any one of aspects 1 to 5 or the oil-resistant agent for paper according to aspects 6 or 7 by an external addition treatment or an internal addition treatment.
- the oil resistant agent for paper imparts high oil resistance to paper.
- the oil resistant composition exhibits high oil resistance even with a small amount of coating.
- the oil resistant agent for paper contains (1) polysaccharides.
- the oil resistant composition comprises (1) a polysaccharide and (2) an oil resistant polymer.
- Polysaccharides are compounds in which a plurality of (3 or more, for example, 3 to 2000) monosaccharides such as glucose, galactose, and fructose are bound.
- the polysaccharide may be an oligosaccharide in which 3 to 10 monosaccharides are bound.
- the polysaccharide may be an acidic polysaccharide, a neutral saccharide and / or a basic saccharide.
- the acidic polysaccharide is generally a polysaccharide having a carboxyl group (-COOH) or the like.
- Specific examples of acidic polysaccharides are carrageenan, pectin, gum arabic, xanthan gum, gellan gum, agar and tragant gum.
- Neutral polysaccharides are polysaccharides that are electrically neutral.
- neutral polysaccharides are tamarind seed gum, guar gum, locust bean gum, starch and pullulan.
- the basic polysaccharide is a polysaccharide having an amino group (-NH 2 ) or the like.
- a specific example of a basic polysaccharide is chitosan.
- polysaccharides include xanthan gum, karaya gum, welan gum, guar gum, pectin, tamarind gum, carrageenan, chitosan, arabic gum, locust bean gum, cellulose, alginic acid, starch, agar, dextran, and pullulan.
- the polysaccharide may be a substituted polysaccharide, in particular a polysaccharide having a hydroxyl group substituted.
- starch As the polysaccharide, starch is preferable.
- the starch may be unmodified starch or modified starch.
- modified starch subjected to at least one modification such as esterification modification, etherification modification, oxidation modification, alkali modification, enzyme modification and bleaching modification is preferable.
- the starch may be pregelatinized starch.
- Pregelatinized starch refers to starch in a state in which hydrogen bonds between sugar chains in the starch are broken and the sugar chains are freed. As used herein, pregelatinized starch is included in modified starch.
- modified starch examples include acetylated adipic acid cross-linked starch, acetylated oxidized starch, acetylated phosphoric acid cross-linked starch, alkenyl succinate-esterified starch, acetate starch, oxidized starch, and hydroxyalkylated starch (alkyl group having 2 carbon atoms).
- examples thereof include acid monoesterified phosphoric acid cross-linked starch, acid-modified starch, alkali-treated starch, enzyme-treated starch, bleached starch, and cationized starch (quaternary ammonium starch). Dextrins obtained by reducing the molecular weight of starch by chemical or enzymatic methods can also be mentioned.
- the starch is a hydrophobized modified starch.
- the hydrophobized modified starch is starch that has been modified (hydrophobicized) so as to have a hydrophobic group (for example, a hydrocarbon group having 1 to 40 carbon atoms, 2 to 40, 3 to 30 or 4 to 20 carbon atoms).
- hydrophobic modified starches are alkenyl succinate esterified starch, acetate esterified starch, polyacrylonitrile grafted starch, (meth) acrylic acid or (meth) acrylic acid ester grafted starch, cross-linked starch.
- Examples of (meth) acrylate esters are methyl (meth) acrylate, ethyl (meth) acrylate, and butyl (meth) acrylate.
- a polyfunctional (2-5-valent) agent is used, and examples of the polyfunctional agent are phosphorus oxychloride, epichlorohydrin and the like.
- hydrophobic modification methods are alkenyl succinic acid (eg, alkenyl groups having 3 to 40 carbon atoms, such as 5 to 30 or 6 to 24) derivatives (eg, octenyl succinic anhydride and dodecenyl succinic anhydride) alkenyl succinate.
- a method for grafting an acrylic monomer (such as ⁇ 30) to the raw material starch a method for reacting the raw material starch with organosilane, and a hydrophobic group containing a hydrocarbon group (for example, 1 to 30 carbon atoms) by etherification or esterification. Is imparted to starch, and the like.
- raw material starch are natural starches such as rice starch, wheat starch, corn starch, potato starch, tapioca starch, and sweet potato starch.
- Alkenyl succinate esterified starch (eg, octenyl succinate esterified starch) is preferred.
- the alkenyl group may have 3 to 40 carbon atoms, for example, 5 to 30 or 6 to 24 carbon atoms.
- Specific examples of the alkenyl succinate esterified starch include octenyl succinate esterified starch, decenyl succinic acid esterified starch, dodecenyl succinic acid esterified starch, tetradecenyl succinic acid esterified starch, and hexadecenyl succinate esterified starch.
- Examples thereof include octadecenyl succinate esterified starch and the like.
- Octenyl succinate esterified starch is preferred.
- the degree of esterification of the esterified starch is expressed as the degree of substitution (DS mol of substituents per mol of anhydrous glucose residue), and the DS may be 0.005 to 0.3 or 0.01 to 0.2.
- the hydrophobized modified starch has a hydrophobic group (for example, a hydrocarbon group having 1 to 40 carbon atoms, 2 to 40 or 3 to 30 carbon atoms), but is hydrophilic (for example, a hydroxyl group, an amino group, a carboxyl group, or an oxyalkylene group (for example). It is preferable that the alkylene also has 1 to 3 carbon atoms, particularly 1 or 2)).
- a hydrophobic group for example, a hydrocarbon group having 1 to 40 carbon atoms, 2 to 40 or 3 to 30 carbon atoms
- hydrophilic for example, a hydroxyl group, an amino group, a carboxyl group, or an oxyalkylene group (for example). It is preferable that the alkylene also has 1 to 3 carbon atoms, particularly 1 or 2)).
- hydrophobic and hydrophilic groups enhances oil resistance.
- preferred starches include hydroxyalkylated starch (eg, hydroxyethylated starch), oxidized starch, alkenyl succinate esterified starch (eg, octenyl succinate esterified starch), dextrin (eg, cyclodextrin), cationization.
- examples include starch and pregelatinized starch.
- the starch may be one type, but is preferably a combination of two or more types of starch.
- the two or more starches are (i) a combination of at least two types of hydrophobized modified starch (eg, starch modified to have a hydrocarbon group having 2 to 40 or 3 to 30 carbon atoms), or (ii).
- a combination of the hydrophobically modified starch and other starches starch other than the hydrophobically modified starch, particularly modified starch other than the hydrophobically modified starch is preferable.
- examples of other starches to be combined are, but are not limited to, for example, etherified starch, oxidized starch, dextrin.
- a preferred combination of two or more starches is a combination comprising an alkenyl succinate esterified starch, a hydroxyalkylated starch or an oxidized starch.
- alkenyl succinate esterified starch and at least one starch selected from the group consisting of hydroxyalkylated starch, oxidized starch, dextrin, cationized starch and pregelatinized starch. It may be a combination of.
- Preferred specific examples of the combination of the hydrophobically modified starch and other starches are alkenyl succinate esterified starch (eg, octenyl succinate esterified starch) and hydroxyalkylated starch (eg, octenyl succinate esterified starch). , Hydroxyethylated starch).
- the weight ratio of the hydrophobized modified starch to the other starches is 10: 90 to 99: 1, 20: 80 to 95: 5 or 30: 70 to 90:10. Alternatively, it may be 40:60 to 85:15.
- the weight ratio of alkenyl succinate esterified starch to other hydrophobic modified starch is 10: 90 to 99: 1, 20: 80 to 95: 5 or 30: 70 to 90 :. It may be 10 or 40:60 to 85:15.
- the oil resistant agent generally also contains a liquid medium, specifically water and / or an organic solvent, preferably an aqueous medium, ie water or a mixture of water and an organic solvent.
- the oil resistant composition comprises (2) an oil resistant polymer in addition to (1) a polysaccharide.
- Oil-resistant polymer (2) is generally a non-fluorine polymer.
- Non-fluorine polymer is (A) A compound having a repeating unit formed from an acrylic monomer having a long-chain hydrocarbon group having 7 to 40 carbon atoms.
- Non-fluorine polymer is Non-fluorine having (a) a repeating unit formed of an acrylic monomer having a long-chain hydrocarbon group having 7 to 40 carbon atoms and (b) a repeating unit formed of an acrylic monomer having a hydrophilic group. It is preferably a copolymer. Further, the non-fluorine copolymer is added to the monomers (a) and (b). (C) It is preferable to have a repeating unit formed of a monomer having an ion donor group. The non-fluorine copolymer can be added to the monomers (a), (b) and (c). (D) It may have a repeating unit formed from another monomer.
- the acrylic monomer (a) having a long-chain hydrocarbon group has a long-chain hydrocarbon group having 7 to 40 carbon atoms.
- the long-chain hydrocarbon group having 7 to 40 carbon atoms is preferably a linear or branched hydrocarbon group having 7 to 40 carbon atoms.
- the number of carbon atoms of the long-chain hydrocarbon group is preferably 10 to 40, for example, 12 to 30, particularly 15 to 30.
- the long-chain hydrocarbon group may have 18 to 40 carbon atoms.
- R 1 is a hydrocarbon group having 7 to 40 carbon atoms independently.
- X 1 is a hydrogen atom, a monovalent organic group or a halogen atom.
- k is 1 to 3.
- It is preferably a monomer represented by.
- X 1 may be a hydrogen atom, a methyl group, a halogen other than a fluorine atom, a substituted or unsubstituted benzyl group, or a substituted or unsubstituted phenyl group.
- Examples of X 1 are a hydrogen atom, a methyl group, a chlorine atom, a bromine atom, an iodine atom, and a cyano group.
- X 1 is preferably a hydrogen atom, a methyl group, or a chlorine atom. It is particularly preferable that X 1 is a hydrogen atom.
- Y 1 is a divalent to tetravalent group.
- Y 1 is preferably a divalent group.
- R 1 is preferably a linear or branched hydrocarbon group.
- the hydrocarbon group may be a linear hydrocarbon group in particular.
- the hydrocarbon group is preferably an aliphatic hydrocarbon group, particularly a saturated aliphatic hydrocarbon group, particularly an alkyl group.
- the hydrocarbon group preferably has 12 to 30, for example 16 to 26 or 15 to 26, particularly 18 to 22 or 17 to 22.
- X 2 is a hydrogen atom, a monovalent organic group or a halogen atom.
- Y 2 is -O- or -NH-.
- X 3 is a hydrogen atom, a monovalent organic group or a halogen atom.
- It is a constituent group Z is a divalent or trivalent hydrocarbon group having 1 to 5 carbon atoms.
- n is 1 or 2.
- (A1) Acrylic monomer
- X 2 is a hydrogen atom, a monovalent organic group or a halogen atom.
- Y 2 is -O- or -NH-. ] It is a compound indicated by.
- the acrylic monomer (a1) is a long-chain acrylate ester monomer in which Y 2 is -O-, or a long-chain acrylamide monomer in which Y 2 is -NH-.
- R2 is preferably an aliphatic hydrocarbon group, particularly a saturated aliphatic hydrocarbon group, particularly an alkyl group. In R2 , the number of carbon atoms of the hydrocarbon group is preferably 12 to 30, for example, 16 to 26, particularly preferably 18 to 22.
- X 2 may be a hydrogen atom, a methyl group, a halogen other than a fluorine atom, a substituted or unsubstituted benzyl group, or a substituted or unsubstituted phenyl group. It is preferably a hydrogen atom, a methyl group or a chlorine atom.
- Preferred specific examples of the long-chain acrylate ester monomer are lauryl (meth) acrylate, stearyl (meth) acrylate, icosyl (meth) acrylate, behenyl (meth) acrylate, stearyl ⁇ -chloroacrylate, icosyl ⁇ -chloroacrylate, and behenyl ⁇ -chloro. It is an acrylate.
- Preferred specific examples of the long-chain acrylamide monomer are stearyl (meth) acrylamide, icosyl (meth) acrylamide, and behenyl (meth) acrylamide.
- the acrylic monomer (a2) is a monomer different from the acrylic monomer (a1).
- X 3 is a hydrogen atom, a monovalent organic group or a halogen atom.
- It is a constituent group Z is a directly bonded or divalent or trivalent hydrocarbon group having 1 to 5 carbon atoms.
- n is 1 or 2.
- R3 is preferably an aliphatic hydrocarbon group , particularly a saturated aliphatic hydrocarbon group, particularly an alkyl group.
- the hydrocarbon group preferably has 12 to 30, for example 16 to 26 or 15 to 26, particularly 18 to 22 or 17 to 22.
- X3 may be a hydrogen atom , a methyl group, a halogen other than a fluorine atom, a substituted or unsubstituted benzyl group, or a substituted or unsubstituted phenyl group. It is preferably a hydrogen atom, a methyl group or a chlorine atom.
- R' is- (CH 2 ) m- (m is an integer of 1 to 5), a linear hydrocarbon group having an unsaturated bond having 1 to 5 carbon atoms, and a branched structure having 1 to 5 carbon atoms.
- Z is a directly bonded or divalent or trivalent hydrocarbon group having 1 to 5 carbon atoms, and may have a linear structure or a branched structure.
- the carbon number of Z is preferably 2 to 4, particularly 2.
- the acrylic monomer (a2) can be produced by reacting hydroxyalkyl (meth) acrylate or hydroxyalkyl (meth) acrylamide with a long-chain alkyl isocyanate.
- the long-chain alkyl isocyanate include lauryl isocyanate, myristyl isocyanate, cetyl isocyanate, stearyl isocyanate, oleyl isocyanate, and behenyl isocyanate.
- the acrylic monomer (a2) can also be produced by reacting a (meth) acrylate having an isocyanate group in the side chain, for example, 2-methacryloyloxyethyl methacrylate with a long-chain alkylamine or a long-chain alkylalcohol.
- a long-chain alkylamine include laurylamine, myristylamine, cetylamine, stearylamine, oleylamine, and behenylamine.
- the long-chain alkyl alcohol include lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, and behenyl alcohol.
- Preferred examples of the long-chain hydrocarbon group-containing acrylic monomer are as follows. Stearyl (meth) acrylate, behenyl (meth) acrylate, stearyl ⁇ -chloroacrylate, behenyl ⁇ -chloroacrylate; Stearyl (meth) acrylamide, behenyl (meth) acrylamide;
- n is a number of 7 to 40 and m is a number of 1 to 5.
- the compound having the above chemical formula is an acrylic compound in which the ⁇ -position is a hydrogen atom, and specific examples may be a metalcle compound in which the ⁇ -position is a methyl group and an ⁇ -chloroacrylic compound in which the ⁇ -position is a chlorine atom.
- the melting point of the acrylic monomer (a) having a long-chain hydrocarbon group is preferably 10 ° C. or higher, more preferably 25 ° C. or higher.
- the acrylic monomer (a) having a long-chain hydrocarbon group is preferably an acrylate in which X 1 , X 2 and X 3 are hydrogen atoms.
- Reference numeral 14 includes a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- R 11 may have various organic groups other than the ethylenically unsaturated polymerizable group, and examples thereof include organic groups such as chain hydrocarbons, cyclic hydrocarbons, polyoxyalkylene groups and polysiloxane groups. These organic groups may be substituted with various substituents.
- R 12 is a hydrocarbon group having 7 to 40 carbon atoms, preferably an alkyl group, and examples thereof include a chain hydrocarbon group and a cyclic hydrocarbon group. Among them, a chain hydrocarbon group is preferable, and a linear saturated hydrocarbon group is particularly preferable.
- the carbon number of R 12 is 7 to 40, preferably 11 to 27, and particularly preferably 15 to 23.
- R 13 is a hydrocarbon group having 1 to 5 carbon atoms, preferably an alkyl group.
- the hydrocarbon group having 1 to 5 carbon atoms may be linear or branched, and may have an unsaturated bond, but a linear group is preferable.
- the carbon number of R 13 is preferably 2 to 4, and particularly preferably 2.
- R 13 is preferably an alkylene group.
- the amide group-containing monomer has one type of R 12 (for example, only a compound in which R 12 has 17 carbon atoms) or a combination of multiple R 12s (for example, R 12 has 17 carbon atoms). It may be a mixture of a compound having 17 carbon atoms and a compound having R 12 having 15 carbon atoms).
- an amide group-containing monomer is a carboxylic acid amide alkyl (meth) acrylate.
- Specific examples of the amide group-containing monomer include amide ethyl palmitate (meth) acrylate, amide ethyl stearate (meth) acrylate, amide ethyl behenate (meth) acrylate, amide ethyl myristate (meth) acrylate, and amide ethyl laurate (meth).
- the amide group-containing monomer is preferably amide ethyl stearate (meth) acrylate.
- the amide group-containing monomer may be a mixture containing an amide ethyl stearate (meth) acrylate.
- the amount of amide ethyl stearate (meth) acrylate is, for example, 55 to 99% by weight, preferably 60 to 85% by weight, based on the total weight of the amide group-containing monomer. More preferably, it may be 65 to 80% by weight, and the remaining monomer may be, for example, amide ethyl palmitate (meth) acrylate.
- the acrylic monomer (b) having a hydrophilic group is a monomer other than the monomer (a) and is a hydrophilic monomer.
- the hydrophilic group is preferably an oxyalkylene group (the alkylene group has 2 to 6 carbon atoms).
- the acrylic monomer (b) having a hydrophilic group is an oxyalkylene (meth) acrylate, for example, a polyalkylene (or monoalkylene) glycol mono (meth) acrylate and / or a polyalkylene (or monoalkylene) glycol di. It is preferably (meth) acrylate, polyalkylene (or monoalkylene) glycol mono (meth) acrylamide.
- X 11 is a hydrogen atom or a methyl group and Y 11 is -O- or -NH- R is an alkylene group having 2 to 6 carbon atoms
- A is a hydrogen atom, an unsaturated or saturated hydrocarbon group having 1 to 22 carbon atoms
- n is an integer from 1 to 90.
- X 12 is an independently hydrogen atom or an unsaturated or saturated hydrocarbon group having 1 to 22 carbon atoms.
- R is an alkylene group having 2 to 6 carbon atoms, n is an integer from 1 to 90.
- n may be, for example, 1 to 50, particularly 1 to 30, specifically 1 to 15 or 2 to 15.
- R may be a linear or branched alkylene group, eg, formula-(CH 2 ) x -or-(CH 2 ) x1- (CH (CH 3 )) x2- [in the formula, x1 and x2 are It is 0 to 6, for example 2 to 5, and the sum of x1 and x2 is 1 to 6.
- -(CH 2 ) x1 -and-(CH (CH 3 )) x2 The order is not limited to the described formula and may be random.
- R may be of 2 or more types (for example, 2 to 4 types, particularly 2 types), and ⁇ (RO) n ⁇ is, for example, ⁇ (R 1 O) n 1 ⁇ and ⁇ .
- (R 2 O) n2- [In the formula, R 1 and R 2 are different from each other and are alkylene groups having 2 to 6 carbon atoms, and n1 and n2 are numbers of 1 or more, and of n1 and n2. The total is 2 to 90. ] May be a combination.
- R in the formulas (b1), (b2) and (b3) is an ethylene group, a propylene group or a butylene group.
- R in the formulas (b1), (b2) and (b3) may be a combination of two or more kinds of alkylene groups. In that case, at least one of R is preferably an ethylene group, a propylene group or a butylene group.
- the R combination include an ethylene group / propylene group combination, an ethylene group / butylene group combination, and a propylene group / butylene group combination.
- the monomer (b) may be a mixture of two or more kinds.
- the monomers (b) is an ethylene group, a propylene group or a butylene group in R in the formula (b1) or (b2) and (b3).
- the polyalkylene glycol di (meth) acrylate represented by the formula (b2) it is not preferable to use it alone as the monomer (b), but it is preferable to use it in combination with the monomer (b1). .. Even in this case, it is preferable that the compound represented by the formula (b2) is kept in an amount of less than 30% by weight in the monomer (b) used.
- acrylic monomer (b) having a hydrophilic group examples include, but are not limited to, the following.
- CH 2 CHCOO-CH 2 CH 2 OH
- CH 2 CHCOO-CH 2 CH 2 CH 2 OH
- CH 2 CHCOO-CH 2 CH (CH 3 )
- OH CH 2 CHCOO-CH (CH 3 ) CH 2 OH
- CH 2 CHCOO-CH 2 CH 2 CH 2 CH (CH 3 )
- the monomer (b) is preferably acrylate or acrylamide in which X 11 is a hydrogen atom.
- X 11 is a hydrogen atom.
- hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, or hydroxyethyl acrylamide is preferable.
- the monomer (c) having an ion donor group is a monomer other than the monomer (a) and the monomer (b).
- the monomer (c) is preferably a monomer having an olefinic carbon-carbon double bond and an ion donating group.
- Ion donors are anion donors and / or cation donors.
- Examples of the monomer having an anion donating group include a monomer having a carboxyl group, a sulfonic acid group or a phosphoric acid group.
- Specific examples of the monomer having an anion donating group include (meth) acrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, vinyl sulfonic acid, (meth) allyl sulfonic acid, styrene sulfonic acid, and phosphorus.
- anion donating group salt examples include alkali metal salts, alkaline earth metal salts, and ammonium salts such as methyl ammonium salt, ethanol ammonium salt, and triethanol ammonium salt.
- an example of the cation donor group is an amino group, preferably a tertiary amino group and a quaternary amino group.
- the two groups bonded to the nitrogen atom are the same or different, an aliphatic group having 1 to 5 carbon atoms (particularly an alkyl group) and an aromatic group having 6 to 20 carbon atoms (aryl group).
- it is preferably an aromatic aliphatic group having 7 to 25 carbon atoms (particularly, an aralkyl group, for example, a benzyl group (C 6 H 5 -CH 2- )).
- the three groups bonded to the nitrogen atom are the same or different, an aliphatic group having 1 to 5 carbon atoms (particularly an alkyl group) and an aromatic group having 6 to 20 carbon atoms (aryl group). Alternatively, it is preferably an aromatic aliphatic group having 7 to 25 carbon atoms (particularly, an aralkyl group, for example, a benzyl group (C 6 H 5 -CH 2- )).
- the remaining one group bonded to the nitrogen atom may have a carbon-carbon double bond.
- the cation donor group may be in the form of a salt.
- the cation donor group which is a salt, is a salt with an acid (organic acid or inorganic acid).
- Organic acids such as carboxylic acids having 1 to 20 carbon atoms (particularly monocarboxylic acids such as acetic acid, propionic acid, butyric acid and stearic acid) are preferred.
- Dimethylaminoethyl (meth) acrylates and diethylaminoethyl (meth) acrylates and salts thereof are preferred.
- CH 2 CHCOO-CH 2 CH 2 -N (CH 3 ) 2 and its salts (eg acetate)
- CH 2 CHCOO-CH 2 CH 2 -N (CH 2 CH 3 ) 2 and its salts (eg acetate)
- CH 2 C (CH 3 ) COO-CH 2 CH 2 -N (CH 3 ) 2 and its salts (eg acetate)
- CH 2 C (CH 3 ) COO-CH 2 CH 2 -N (CH 2 CH 3 ) 2 and its salts (eg acetate)
- CH 2 C (CH 3 ) COO-CH 2 CH 2 -N (CH 2 CH 3 ) 2 and its salts (eg acetate)
- CH 2 CHC (O) N (H) -CH 2 CH 2 CH 2 -N (CH 3 ) 2 and its salts (eg acetate)
- CH 2 CHCOO-CH 2 CH 2 -N (-CH 3 ) (-CH 2 -C 6 H 5 ) and
- the monomer (c) having an ion donor group methacrylic acid, acrylic acid and dimethylaminoethyl methacrylate are preferable, and methacrylic acid and dimethylaminoethyl methacrylate are more preferable.
- the other monomer (d) is a monomer other than the monomers (a), (b) and (c).
- Such other monomers include ethylene, vinyl acetate, vinyl chloride, vinyl fluoride, vinyl halide stin, ⁇ -methylstyrene, p-methylstyrene, polyoxyalkylene mono (meth) acrylate, (meth) acrylamide.
- the amount of the repeating unit (repeating unit (a)) formed from the monomer (a) is relative to the non-fluoropolymer (or relative to the sum of the repeating unit (a) and the repeating unit (b)). , 30-95% by weight or 30-90% by weight, preferably 40-88% by weight (or 45-95% by weight), more preferably 50-85% by weight.
- the amount of the repeating unit (repeating unit (b)) formed from the monomer (b) is relative to the non-fluoropolymer (or relative to the sum of the repeating unit (a) and the repeating unit (b)). It may be 5 to 70% by weight or 10 to 70% by weight, preferably 8 to 50% by weight, and more preferably 10 to 40% by weight.
- the amount of the repeating unit formed from the monomer (c) is 0.1 to 30% by weight, preferably 0.5 to 20% by weight, more preferably 1 to 15% by weight, based on the non-fluorine copolymer. May be%.
- the amount of the repeating unit formed from the monomer (d) may be 0 to 20% by weight, for example 1 to 15% by weight, particularly 2 to 10% by weight, based on the non-fluorine copolymer.
- the weight average molecular weight of the non-fluorine copolymer may be 1000-1000000 or 10000000, preferably 5000-800000 or 8000000, more preferably 10000-4000000 or 4000000.
- the weight average molecular weight is a value obtained in terms of polystyrene by gel permeation chromatography.
- (meth) acrylic means acrylic or methacrylic.
- (meth) acrylate means acrylate or methacrylate.
- the non-fluorine copolymer is preferably a random copolymer rather than a block copolymer.
- the melting point or glass transition point of the non-fluorine copolymer is preferably 20 ° C. or higher, more preferably 30 ° C. or higher, particularly preferably 35 ° C. or higher, for example 40 ° C. or higher.
- the polymerization of the non-fluoropolymer is not particularly limited, and various polymerization methods such as bulk polymerization, solution polymerization, emulsion polymerization and radiation polymerization can be selected.
- solution polymerization using an organic solvent or emulsion polymerization using water or an organic solvent and water in combination is selected. After polymerization, it is diluted with water and emulsified in water to prepare a treatment liquid.
- water is added and then the solvent is removed to disperse the polymer in water.
- Self-dispersive products can be produced without the need to add emulsifiers.
- organic solvent examples include ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate and methyl acetate, propylene glycol, dipropylene glycol monomethyl ether, N-methyl-2-pyrrolidone (NMP), dipropylene glycol and tripropylene glycol.
- ketones such as acetone and methyl ethyl ketone
- esters such as ethyl acetate and methyl acetate
- propylene glycol dipropylene glycol monomethyl ether
- NMP N-methyl-2-pyrrolidone
- dipropylene glycol and tripropylene glycol examples include N-methyl-2-pyrrolidone (NMP), dipropylene glycol and tripropylene glycol.
- Glycols such as low molecular weight polyethylene glycol, alcohols such as ethyl alcohol and isopropanol, and the like.
- the polymerization initiator for example, a peroxide, an azo compound or a persulfuric acid-based compound can be used.
- the polymerization initiator is generally water-soluble and / or oil-soluble.
- Specific examples of the oil-soluble polymerization initiator include 2,2'-azobis (2-methylpropionitrile), 2,2'-azobis (2-methylbutyronitrile), and 2,2'-azobis (2, 4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethyl4-methoxyvaleronitrile), 1,1'-azobis (cyclohexane-1-carbonitrile), dimethyl 2,2'-azobis (2) -Methylpropionate), 2,2'-azobis (2-isobutyronitrile), benzoylperoxide, di-tertiary-butyl peroxide, lauryl peroxide, cumenehydroperoxide, t-butylperoxy Pivalate, diisopropylper
- water-soluble polymerization initiator examples include 2,2'-azobisisobutyramidine dihydrogenate, 2,2'-azobis (2-methylpropionamidin) hydrochloride, and 2,2'-azobis [. 2- (2-imidazolin-2-yl) propane] hydrochloride, 2,2'-azobis [2- (2-imidazolin-2-yl) propane] sulfate hydrate, 2,2'-azobis [2- (5-Methyl-2-imidazolin-2-yl) Propane] Hydrochloride, potassium persulfate, barium persulfate, ammonium persulfate, hydrogen peroxide and the like are preferable.
- the polymerization initiator is used in the range of 0.01 to 5 parts by weight with respect to 100 parts by weight of the monomer.
- a chain transfer agent for example, a mercapto group-containing compound may be used for the purpose of adjusting the molecular weight, and specific examples thereof include 2-mercaptoethanol, thiopropionic acid, and alkyl mercaptan.
- the mercapto group-containing compound is used in the range of 10 parts by weight or less and 0.01 to 5 parts by weight with respect to 100 parts by weight of the monomer.
- the non-fluorine copolymer can be produced as follows.
- solution polymerization a method is adopted in which the monomer is dissolved in an organic solvent, substituted with nitrogen, a polymerization initiator is added, and the mixture is heated and stirred in the range of 40 to 120 ° C. for 1 to 10 hours, for example.
- the polymerization initiator may generally be an oil-soluble polymerization initiator.
- the organic solvent is inert to the monomer and dissolves them.
- Ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate and methyl acetate, propylene glycol, dipropylene glycol monomethyl ether and N-methyl.
- -Glycols such as 2-pyrrolidone (NMP), dipropylene glycol, tripropylene glycol, low molecular weight polyethylene glycol, alcohols such as ethyl alcohol and isopropanol, n-heptane, n-hexane, n-octane, cyclohexane, methyl Hydrocarbon solvents such as cyclohexane, cyclopentane, methylcyclopentane, methylpentane, 2-ethylpentane, isoparaffin hydrocarbons, liquid paraffin, decane, undecane, dodecane, mineral spirit, mineral tarpen, and naphtha.
- NMP 2-pyrrolidone
- dipropylene glycol tripropylene glycol
- low molecular weight polyethylene glycol alcohols such as ethyl alcohol and isopropanol
- alcohols such as ethyl alcohol and isopropanol
- Preferred examples of the solvent include, for example, acetone, chloroform, HCHC225, isopropyl alcohol, pentane, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, petroleum ether, tetrahydrofuran, 1,4-dioxane, methyl ethyl ketone, methyl isobutyl ketone, Ethyl acetate, butyl acetate, 1,1,2,2-tetrachloroethane, 1,1,1-trichloroethane, trichlorethylene, perchloroethylene, tetrachlorodifluoroethane, trichlorotrifluoroethane, N-methyl-2-pyrrolidone (NMP) , Dipropylene glycol monomethyl ether (DPM) and the like.
- the organic solvent is used in the range of 50 to 2000
- emulsion polymerization a method is adopted in which a monomer is emulsified in water in the presence of an emulsifier, nitrogen substitution is performed, a polymerization initiator is added, and the mixture is stirred and polymerized in the range of 40 to 80 ° C. for 1 to 10 hours. Will be done.
- the polymerization initiator is a water-soluble polymerization initiator, for example, 2,2'-azobisisobutyramidine dihydrochloride, 2,2'-azobis (2-methylpropionamidin) hydrochloride, 2,2'-azobis [ 2- (2-imidazolin-2-yl) propane] hydrochloride, 2,2'-azobis [2- (2-imidazolin-2-yl) propane] sulfate hydrate, 2,2'-azobis [2- (5-Methyl-2-imidazolin-2-yl) Propane] Hydrochloride, potassium persulfate, barium persulfate, ammonium persulfate, hydrogen peroxide, Also, oil-soluble polymerization initiators such as 2,2'-azobis (2-methylpropionitrile), 2,2'-azobis (2-methylbutyronitrile), 2,2'-azobis (2,4-).
- 2,2'-azobisisobutyramidine dihydrochloride 2,2'-
- Dimethylvaleronitrile 2,2'-azobis (2,4-dimethyl4-methoxyvaleronitrile), 1,1'-azobis (cyclohexane-1-carbonitrile), dimethyl 2,2'-azobis (2-methyl) Propionate), 2,2'-azobis (2-isobutyronitrile), benzoyl peroxide, di-tertiary-butyl peroxide, lauryl peroxide, cumene hydroperoxide, t-butyl peroxypivalate. , Diisopropylperoxydicarbonate, t-butyl hyperpivalate is used.
- the polymerization initiator is used in the range of 0.01 to 10 parts by weight with respect to 100 parts by weight of the monomer.
- a monomer is atomized into water using an emulsifying device such as a high-pressure homogenizer or an ultrasonic homogenizer that can impart strong crushing energy, and is oil-soluble. It is desirable to polymerize using a polymerization initiator.
- an emulsifier various anionic, cationic or nonionic emulsifiers can be used, and they are used in the range of 0.5 to 20 parts by weight with respect to 100 parts by weight of the monomer. It is preferred to use anionic and / or nonionic and / or cationic emulsifiers.
- compatibilizer that is sufficiently compatible with these monomers, for example, a water-soluble organic solvent or a low molecular weight monomer. It is possible to improve emulsifying property and copolymerizability by adding a compatibilizer.
- Water-soluble organic solvents include acetone, propylene glycol, dipropylene glycol monomethyl ether (DPM), dipropylene glycol, tripropylene glycol, ethanol, N-methyl-2-pyrrolidone (NMP), 3-methoxy-3-methyl-.
- Examples thereof include 1-butanol or isopylene glycol, which may be used in the range of 1 to 50 parts by weight, for example, 10 to 40 parts by weight with respect to 100 parts by weight of water.
- the composition by adding NMP or DPM or 3-methoxy-3-methyl-1-butanol or isoprene glycol (preferably an amount of 1 to 20% by weight, particularly 3 to 10% by weight) based on the composition. The stability of (especially emulsion) is improved.
- low molecular weight monomer examples include methyl methacrylate, glycidyl methacrylate, 2,2,2-trifluoroethyl methacrylate and the like, and 1 to 50 parts by weight, based on 100 parts by weight of the total amount of the monomer. For example, it may be used in the range of 10 to 40 parts by weight.
- oil resistant agent or composition (in the present specification, the oil resistant agent and the oil resistant composition may be referred to as "oil resistant agent”) is preferably in the form of a solution, an emulsion or an aerosol.
- the oil resistant agent comprises a polysaccharide and a medium (eg, an organic solvent and a liquid medium such as water).
- the amount of the polysaccharide may be 1% by weight or more, 5% by weight or more or 30% by weight or more, for example, 1 to 70% by weight or 5 to 60% by weight, based on the oil resistant agent or the oil resistant composition.
- the amount of the oil resistant polymer may be, for example, 0 to 50% by weight, 0.1 to 40% by weight or 1 to 30% by weight based on the oil resistant composition.
- the oil resistant agent preferably does not contain an emulsifier.
- the weight ratio of the polysaccharide to the oil resistant polymer is 10: 90 to 98: 2, for example 40: 60 to 95: 5 or 55: 45 to 90:10, especially 70: 30 to 95: 5, 80: 20 to.
- the treatment liquid for processing paper preferably has a viscosity of 200 cps or less, for example, 150 cps or less, 100 cps or less, or 80 cps or less at 50 ° C.
- the lower limit of the viscosity may be 1 cps.
- the removal of the organic solvent in the polymer solution can be performed by heating the polymer solution (preferably under reduced pressure) (for example, to 30 ° C. or higher, for example, 50 to 120 ° C.).
- the oil resistant agent can be used to treat (eg, surface treat) the paper substrate.
- surface treatment external addition
- the oil resistant agent can be applied to the object to be treated by a conventionally known method.
- an oil resistant agent is dispersed in an organic solvent or water, diluted, and adhered to the surface of the object to be treated by a known method such as dip coating, spray coating, foam coating, etc., and dried (the method is adopted).
- surface treatment examples of the paper base material of the object to be treated include paper, a container made of paper, and a molded product made of paper (for example, pulp mold). Food packaging materials and food containers are preferred. Polysaccharides and oil resistant polymers adhere well to paper substrates.
- Paper can be manufactured by a conventionally known papermaking method.
- An internal addition treatment method in which an oil resistant agent is added to the pulp slurry before papermaking, or an external addition treatment method in which an oil resistant agent is applied to the paper after papermaking can be used.
- an external addition treatment method is preferable.
- the size press of the external addition treatment method can also be divided as follows depending on the coating method.
- a coating liquid size liquid
- a coating liquid size liquid
- a pound-type two-roll size press that applies a size liquid to the paper.
- Other coating methods are a gate roll type in which a size liquid is applied by a surface transfer type, and a rod metering size press.
- the size liquid easily penetrates into the inside of the paper, and in the surface transfer type, the size liquid component tends to stay on the surface of the paper.
- the coating layer tends to stay on the surface of the paper as compared with the pound type two-roll size press, and the oil-resistant layer formed on the surface is larger than that of the pound type two-roll size press.
- oil resistance can be imparted to paper even when the former pound type two-roll size press is used.
- the paper thus treated can optionally take a temperature range of up to 300 ° C., for example up to 200 ° C., in particular 80 ° C. to 180 ° C., depending on the nature of the paper, after simple drying at room temperature or high temperature. With heat treatment, it exhibits excellent oil resistance and water resistance.
- This disclosure can be used for gypsum board base paper, coated base paper, medium quality paper, general liner and core, neutral pure white roll paper, neutral liner, rustproof liner and metal interleaving paper, kraft paper, etc. It can also be used in neutral printing writing paper, neutral coated base paper, neutral PPC paper, neutral heat sensitive paper, neutral pressure sensitive base paper, neutral inkjet paper, and neutral information paper.
- pulp raw material bleached or unbleached chemical pulp such as kraft pulp or sulfide pulp, crushed wood pulp, bleached or unbleached high-yield pulp such as mechanical pulp or thermomechanical pulp, used newspaper, used magazine, used cardboard or removed. Any of used paper pulp such as ink used paper can be used. Further, a mixture of the above pulp raw material and synthetic fibers such as asbestos, polyamide, polyimide, polyester, polyolefin and polyvinyl alcohol can also be used.
- a sizing agent can be added to improve the water resistance of the paper.
- sizing agents are cationic sizing agents, anionic sizing agents, rosin-based sizing agents (eg, acidic rosin-based sizing agents, neutral rosin-based sizing agents).
- the amount of sizing agent may be 0.01-5% by weight with respect to the pulp.
- Paper strength enhancers such as carboxymethyl cellulose, polyamide polyamine-epichlorohydrin resin, flocculants, fixing agents, yield improvers, dyes, fluorescent dyes, slimes, as necessary, as paper-making agents that are usually used for paper.
- Additives used in the production of paper such as control agents and antifoaming agents can be used.
- the oil resistant agent can be applied to the paper by a size press, a gate roll coater, a bill blade coater, a calender, or the like using polyvinyl alcohol, glucose, a dye, a coating color, an antislip agent, or the like. It is preferable to use polyvinyl alcohol or glucose as an additive.
- High oil resistance can be obtained by using polyvinyl alcohol or glucose together with polysaccharides.
- the amount of polyvinyl alcohol may be 1 to 1000 parts by weight, 2 to 200 parts by weight, 3 to 100 parts by weight or 5 to 50 parts by weight, particularly 10 to 40 parts by weight, based on 100 parts by weight of the polysaccharide.
- the oil resistant layer is preferably formed of a polysaccharide (and an oil resistant polymer).
- the amount of polysaccharides contained in the oil resistant layer is 0.01 to 5.0 g / m 2 , especially 0.1 to 3.0 g / m 2 , 0.1 to 2.0 g / m 2 or 0.1 to 1. It is preferably 0 g / m 2 .
- the amount of the oil-resistant polymer contained in the oil-resistant layer is preferably 0.01 to 2.0 g / m 2 , particularly preferably 0.1 to 1.0 g / m 2 .
- the solid content of the oil-resistant agent for paper in the oil-resistant layer is preferably 2 g / m 2 or less.
- the solid content of the additive including polyvinyl alcohol contained in the oil resistant layer may be 0.01 to 1.0 g / m 2 or 0.1 to 0.5 g / m 2 .
- the amount of the oil resistant agent is 0.01 to 50 parts by weight or 0.01 to 30 parts by weight, for example, 0.01 to 10 parts by weight, particularly 0. It is preferable to mix the oil resistant agent with the pulp so as to be 2 to 5.0 parts by weight.
- the weight ratio of the polysaccharide to the non-fluorine copolymer may be 10:90 to 98: 2, for example 40:60 to 95: 5 or 55:45 to 90:10.
- the weight ratio of the polysaccharide to the additive may be 70:30 to 99: 1, 80:20 to 95: 5 or 85:15 to 90:10.
- the treatment liquid is stored between the rolls, and the base paper is passed through the treatment liquid between the rolls at an arbitrary roll speed and nip pressure. Can be given.
- the oil resistant polymer may be nonionic, cationic, anionic or amphoteric.
- the paper substrate may contain additives such as sizing agents, paper strength enhancers, flocculants, yields or coagulants.
- Additives may be nonionic, cationic, anionic or amphoteric.
- the ionic charge density of the additive may be ⁇ 10000 to 10000 ⁇ eq / g, preferably ⁇ 4000 to 8000 ⁇ eq / g, and more preferably ⁇ 1000 to 7000 ⁇ eq / g.
- Additives such as sizing agents, paper strength enhancers, flocculants, yields or coagulants are generally 0.1-10% by weight (eg 0.2- It can be used in an amount of 5.0% by weight).
- the oil resistant agent is preferably anionic.
- a pulp slurry having a pulp concentration of 0.5 to 5.0% by weight for example, 2.5 to 4.0% by weight.
- additives examples include polyvinyl alcohol, alkyl ketene dimer, alkenyl succinic anhydride, styrene-based polymers (styrene / maleic acid-based heavy weight).
- styrene / acrylic acid polymer urea-formaldehyde polymer, polyethyleneimine, melamine-formaldehyde polymer, polyamideamine-epicchlorohydrin polymer, polyacrylamide polymer, polyamine polymer, polydiallyldimethylammonium chloride, Alkylamine / epichlorohydrin condensate, alkylene dichloride and polyalkylene polyamine condensate, dicyandiamide / formarin condensate, dimethyldiallylammonium chloride polymer, olefin / maleic anhydride polymer.
- the article to be treated is treated with an oil resistant agent.
- “Treatment” means applying an oil resistant agent to an object to be treated by dipping, spraying, coating or the like.
- polysaccharides and non-fluorine copolymers which are the active ingredients of the oil resistant agent, permeate the inside of the object to be treated and / or adhere to the surface of the object to be treated.
- Viscosity of the treatment liquid The viscosity (cps) was measured using a rotary viscometer (B type) that reads the resistance (viscosity resistance) received from the fluid by the rotating body from the rotational torque and the like.
- KIT Oil resistance
- KIT method Oil resistance (KIT method) was measured according to TAPPI T-559 cm-02.
- the KIT test solution is a test solution in which castor oil, toluene, and heptane are mixed at the ratios shown in Table 1.
- One drop of the test solution shown in Table 1 was placed on paper, and the oil penetration state was observed after 15 seconds.
- the highest point of oil resistance given by the KIT test solution showing no penetration was defined as oil resistance.
- Synthesis example 1 A reactor having a volume of 500 ml equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, a nitrogen inlet and a heating device was prepared, and 100 parts of methyl ethyl ketone (MEK) as a solvent was added. Subsequently, under stirring, a monomer (monomer) consisting of 78 parts of stearate amide ethyl acrylate (C18AmEA, melting point: 70 ° C.), 16 parts of hydroxyethyl acrylate (HEA), and 6 parts of dimethylaminoethyl methacrylate (DM).
- MK methyl ethyl ketone
- a total of 100 parts) and 1.2 parts of perbutyl PV (PV) as an initiator were added in this order, and the mixture was mixed and stirred for 12 hours under a nitrogen atmosphere at 65-75 ° C. to carry out copolymerization.
- the solid content concentration of the obtained copolymer-containing solution was 50% by weight.
- 142 g of a 0.4% aqueous acetic acid solution was added to 50 g of the obtained copolymer solution and dispersed, and then MEK was distilled off under reduced pressure while heating with an evaporator to obtain a milky white copolymer.
- a polymerized water dispersion content of volatile organic solvent is 1% by weight or less
- LBKP broadleaf bleached kraft pulp
- NBKP coniferous bleached kraft pulp
- the filtrate content of the pulp is 400 ml (Canadian Standard Freeens).
- a wet paper strength agent was added to the pulp slurry in a solid content concentration of 0.5% by weight with respect to the dried pulp, and a paper density of 0.58 g / cm3 was added to the basis weight of 45 g / by a Naganet paper making machine.
- the m2 paper was used as the base paper for the external addition treatment (size press treatment).
- the oil resistance (KIT value) of this base paper was 0, and the water resistance (Cobb value) was 52 g / m 2 .
- the aqueous dispersion of the copolymer obtained in Synthesis Example 1 was used as an oil resistant agent, and an oil resistant paper (processed paper) was obtained by the following formulation.
- the treatment liquid was adjusted by adjusting the aqueous dispersion of the copolymer obtained in Synthesis Example 1 so that the solid content concentration was 1.5% by weight and the solid content concentration of starch was 7%, and using a size press machine. After the treatment, it was dried with a drum dryer to obtain an oil resistant paper (processed paper).
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 0.8 g / m 2 (the coating amount of the copolymer was 0.14 g / m 2 ).
- the obtained base paper was used as a test paper, and a kit test was performed. The evaluation results are shown in Table 2.
- As the starch described here hydroxyethylated modified starch (10 wt% viscosity at 50 ° C. of 11 cps) was used.
- the size press process described here (using a size press machine manufactured by Mathis) is to store the processing liquid between rolls, and pass the base paper through the processing liquid between rolls at an arbitrary roll speed and nip pressure. This is the so-called pound-type two-roll size press process.
- Example 2 The same treatment as in Example 1 was carried out except that the starch concentration in the treatment liquid was 10% by weight.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 1.2 g / m 2 (the coating amount of the copolymer was 0.16 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 3 The same treatment as in Example 1 was carried out except that the starch concentration in the treatment liquid was 14% by weight.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 1.8 / m 2 (the coating amount of the copolymer was 0.17 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 4 The same treatment as in Example 1 was carried out except that oxidized starch (10% by weight, viscosity at 50 ° C. was 26 cps) was used instead of the hydroxyethylated modified starch of Example 1.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 0.8 / m 2 (the coating amount of the copolymer was 0.14 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 5 The same treatment as in Example 1 was carried out except that octenyl succinic acid-modified starch (10 wt% viscosity at 50 ° C. was 7 cps) was used instead of the hydroxyethylated modified starch of Example 1.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 0.8 / m 2 (the coating amount of the copolymer was 0.14 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 6 The same treatment as in Example 5 was carried out except that the starch concentration in the treatment liquid was 14% by weight.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 1.8 g / m 2 (the coating amount of the copolymer was 0.17 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 7 The same treatment as in Example 1 was carried out except that 30% by weight of dextrin (10% by weight, viscosity at 50 ° C. was 3 cps) was used instead of the hydroxyethylated modified starch of Example 1.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 4.0 / m 2 (the coating amount of the copolymer was 0.19 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 8 The same treatment as in Example 1 was carried out except that 5% by weight of cationized modified starch (10% by weight at 50 ° C. viscosity of 80 cps) was used instead of the hydroxyethylated modified starch of Example 1.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 0.6 / m 2 (the coating amount of the copolymer was 0.15 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 9 The same treatment as in Example 1 was carried out except that 2% by weight of polyvinyl alcohol was added to Example 1.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 1.2 / m 2 (the coating amount of the copolymer was 0.17 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 10 The same treatment as in Example 1 was carried out except that 7% by weight of octenyl succinic acid-modified starch was added to Example 1.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 1.9 g / m 2 (the coating amount of the copolymer was 0.18 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 11 The same treatment as in Example 10 was carried out except that the copolymer was not used.
- the coating amount of the solid content of the obtained oil-resistant paper was 1.8 g / m 2 .
- the results of the kit test are shown in Table 2.
- Example 12 The same treatment as in Example 1 was carried out except that 25% by weight of pregelatinized starch A (25% by weight of viscosity at 50 ° C. was 41 cps) was used instead of the hydroxyethylated modified starch of Example 1.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 1.9 / m 2 (the coating amount of the copolymer was 0.11 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 13 The same treatment as in Example 1 was carried out except that 30% by weight of pregelatinized starch B (30% by weight of viscosity at 50 ° C. was 22 cps) was used instead of the hydroxyethylated modified starch of Example 1.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 2.1 / m 2 (the coating amount of the copolymer was 0.10 g / m 2 ).
- the results of the kit test are shown in Table 2.
- Example 14 The same treatment as in Example 3 was carried out except that 10% by weight of glucose was added to Example 3.
- the coating amount of the starch of the obtained oil-resistant paper and the solid content of the copolymer was 1.9 / m 2 (the coating amount of the copolymer was 0.14 g / m 2 ).
- the results of the kit test are shown in Table 2.
- the oil-resistant agent and oil-resistant composition of the present disclosure can be applied to paper used for food containers and food packaging materials.
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Abstract
Description
さらに、本開示は、紙用耐油剤と水との混合物である粘度200cps以下の処理液にも関する。粘度は、50℃の温度での粘度であり、好ましくは150cps以下、100cps以下または80cps以下である。粘度の下限は1cpsであってよい。
加えて、本開示は、多糖類および耐油性ポリマーを含んでなる耐油組成物に関する。
紙用耐油剤および耐油組成物は、水および/または有機溶媒、好ましくは水または水と有機溶媒の混合物(水性媒体)である液状媒体をも含有してよい。
本開示は、紙用耐油剤または耐油組成物で処理されている耐油紙を提供する。紙の処理は、外添または内添である。耐油紙は、外添処理方法により、紙用耐油剤または耐油組成物を含む耐油層を有する。あるいは耐油紙は、内添処理方法により、紙用耐油剤または耐油組成物を紙の内部に含む。
態様1:
(1)多糖類および(2)耐油性ポリマーを含んでなる耐油組成物。
態様2:
耐油性ポリマー(2)が、
(a)炭素数7~40の長鎖炭化水素基を有するアクリル単量体から形成された繰り返し単位、および
(b)親水性基を有するアクリル単量体から形成された繰り返し単位
を有する非フッ素共重合体であり、
多糖類と耐油性ポリマーとの重量比が、10:90~98:2である態様1に記載の耐油組成物。
態様3:
長鎖炭化水素基を有するアクリル単量体(a)が、式:
CH2=C(-X1)-C(=O)-Y1(R1)k
[式中、R1は、それぞれ独立的に、炭素数7~40の炭化水素基であり、
X1は、水素原子、一価の有機基またはハロゲン原子であり、
Y1は、2価~4価の炭素数1の炭化水素基、-C6H4-、-O-、-C(=O)-、-S(=O)2-または-NH-から選ばれる少なくとも1つ以上で構成される基(但し、炭化水素基を除く)であり、
kは1~3である。]
で示される単量体である態様2に記載の耐油組成物。
態様4:
長鎖炭化水素基を有するアクリル単量体(a)が、
(a1)式:
CH2=C(-X2)-C(=O)-Y2-R2
[式中、R2は、炭素数7~40の炭化水素基であり、
X2は、水素原子、一価の有機基またはハロゲン原子であり、
Y2は、-O-または-NH-である。]
で示されるアクリル単量体、および/または
(a2)式:
CH2=C(-X3)-C(=O)-Y3-Z(-Y4-R3)n
[式中、R3は、それぞれ独立的に、炭素数7~40の炭化水素基であり、
X3は、水素原子、一価の有機基またはハロゲン原子であり、
Y3は、-O-または-NH-であり、
Y4は、それぞれ独立的に、直接結合、あるいは-O-、-C(=O)-、-S(=O)2-、-NH-または-CH2-から選ばれる少なくとも1つ以上で構成される基であり、
Zは、直接結合、あるいは2価または3価の炭素数1~5の炭化水素基であり、
nは、1または2である。]
で示されるアクリル単量体であり、
親水性基を有するアクリル単量体(b)が、式:
CH2=CX11C(=O)-Y11-(RO)n-A
[式中、
X11は、水素原子またはメチル基であり、
Y11は、-O-または-NH-であり、
Rは、炭素数2~6のアルキレン基、
Aは、水素原子、炭素数1~22の不飽和または飽和の炭化水素基、またはCH2=CX12C(=O)-(ただし、X12は、水素原子またはメチル基である。)であり、
nは、1~90の整数である。]
で示されるオキシアルキレン(メタ)アクリレートである、態様2~3のいずれかに記載の耐油組成物。
態様5:
水または水と有機溶媒の混合物である液状媒体をさらに含んでなる態様1~4のいずれかに記載の耐油組成物。
態様6:
2種以上の多糖類の組み合わせを含んでなる紙用耐油剤。
態様7:
少なくとも1種の多糖類が、変性澱粉であるか、またはヒドロキシアルキル化澱粉、酸化澱粉、アルケニルコハク酸エステル化澱粉、デキストリン、カチオン化澱粉およびアルファ化澱粉からなる群から選択された少なくとも1種の澱粉であり、紙の外添に用いる態様6に記載の紙用耐油剤。
態様8:
態様1~5のいずれかに記載の耐油組成物または態様6または7に記載の紙用耐油剤と水から形成されており、粘度が200cps以下である処理液。
態様9:
耐油層を形成させるために用いる態様8記載の処理液。
態様10:
処理液における多糖類の量が、5重量%以上である態様8または9記載の処理液。
態様11:
添加剤をも含む態様8~10のいずれかに記載の処理液。
態様12:
添加剤がポリビニルアルコールおよびグルコースから選択された少なくとも1種である態様11に記載の処理液。
態様13:
態様1~5のいずれかに記載の耐油組成物または態様6または7に記載の紙用耐油剤から形成された耐油層を紙の表面に有する耐油紙。
態様14:
食品包装材または食品容器である態様13に記載の耐油紙。
態様15:
態様1~5のいずれかに記載の耐油組成物または態様6または7に記載の紙用耐油剤で紙を外添処理または内添処理により処理する紙の処理方法。
耐油組成物は、塗工量が少なくても、高い耐油性を示す。
耐油組成物は、(1)多糖類、および(2)耐油ポリマーを含んでなる。
多糖類は、グルコース、ガラクトース、フルクトース等の単糖類が複数(3以上、例えば3~2000)で結合した化合物である。多糖類は、単糖類が3~10個結合したオリゴ糖類であってもよい。
酸性多糖類は、一般的に、カルボキシル基(-COOH)等を有する多糖類である。 酸性多糖類の具体例は、カラギナン、ペクチン、アラビアガム、キサンタンガム、ジェランガム、寒天、トラガントガムである。
中性多糖類は、電気的に中性である多糖類である。中性多糖類の具体例は、タマリンドシードガム、グァーガム、ローカストビーンガム、澱粉、プルランである。
塩基性多糖類は、アミノ基(-NH2)等を有する多糖類である。塩基性多糖類の具体例は、キトサンである。
変性澱粉としては、例えば、アセチル化アジピン酸架橋澱粉、アセチル化酸化澱粉、アセチル化リン酸架橋澱粉、アルケニルコハク酸エステル化澱粉、酢酸澱粉、酸化澱粉、ヒドロキシアルキル化澱粉(アルキル基の炭素数2~40または2~10、特に2または3)、ヒドロキシアルキル化リン酸架橋澱粉(アルキル基の炭素数2~40または2~10、特に2または3)、リン酸架橋澱粉、リン酸化澱粉、リン酸モノエステル化リン酸架橋澱粉、酸変性澱粉、アルカリ処理澱粉、酵素処理澱粉、漂白処理澱粉、カチオン化澱粉(四級アンモニウム化澱粉)を挙げることができる。澱粉を化学的あるいは酵素的な方法により低分子化したデキストリンも挙げることができる。
エステル化澱粉のエステル化度は置換度として表し(無水グルコース残基1モル当りの置換基DSモル)、DSが0.005~0.3または0.01~0.2であってよい。
好ましい澱粉の具体例としては、ヒドロキシアルキル化澱粉(例えば、ヒドロキシエチル化澱粉)、酸化澱粉、アルケニルコハク酸エステル化澱粉(例えば、オクテニルコハク酸エステル化澱粉)、デキストリン(例えば、シクロデキストリン)、カチオン化澱粉およびアルファ化澱粉が挙げられる。
2種以上の澱粉の好ましい組み合わせは、アルケニルコハク酸エステル化澱粉、ヒドロキシアルキル化澱粉または酸化澱粉を含む組み合わせである。2種以上の澱粉の好ましい組み合わせの例は、アルケニルコハク酸エステル化澱粉と、ヒドロキシアルキル化澱粉、酸化澱粉、デキストリン、カチオン化澱粉およびアルファ化澱粉からなる群から選択された少なくとも1種の澱粉との組み合わせであってよい。
疎水化変性澱粉と、他の澱粉(疎水化変性澱粉以外の澱粉)との組み合わせの好ましい具体例としては、アルケニルコハク酸エステル化澱粉(例えば、オクテニルコハク酸エステル化澱粉)とヒドロキシアルキル化澱粉(例えば、ヒドロキシエチル化澱粉)との組み合わせが挙げられる。
耐油ポリマー(2)は、一般に、非フッ素重合体である。
非フッ素重合体は、
(a)炭素数7~40の長鎖炭化水素基を有するアクリル単量体から形成される繰り返し単位
を有する化合物である。
(a)炭素数7~40の長鎖炭化水素基を有するアクリル単量体から形成される繰り返し単位、および
(b)親水性基を有するアクリル単量体から形成される繰り返し単位を有する非フッ素共重合体であることが好ましい。
さらに、非フッ素共重合体は、単量体(a)および(b)に加えて、
(c)イオン供与基を有する単量体
によって形成されている繰り返し単位を有することが好ましい。
非フッ素共重合体は、単量体(a)、(b)および(c)に加えて、
(d)他の単量体
から形成される繰り返し単位を有していてもよい。
長鎖炭化水素基を有するアクリル単量体(a)は、炭素数7~40の長鎖炭化水素基を有する。炭素数7~40の長鎖炭化水素基は、炭素数7~40の直鎖状または分岐状の炭化水素基であることが好ましい。長鎖炭化水素基の炭素数は、10~40、例えば、12~30、特に15~30であることが好ましい。あるいは、長鎖炭化水素基の炭素数は、18~40であってよい。
CH2=C(-X1)-C(=O)-Y1(R1)k
[式中、R1は、それぞれ独立的に、炭素数7~40の炭化水素基であり、
X1は、水素原子、一価の有機基またはハロゲン原子であり、
Y1は、2価~4価の炭素数1の炭化水素基(特に、-CH2-、-CH=)、-C6H4-、-O-、-C(=O)-、-S(=O)2-または-NH-から選ばれる少なくとも1つ以上で構成される基(但し、炭化水素基を除く)であり、
kは1~3である。]
で示される単量体であることが好ましい。
Y1は、炭素数1の炭化水素基、-C6H4-、-O-、-C(=O)-、-S(=O)2-または-NH-から選ばれる少なくとも1つ以上によって構成される基(但し、炭化水素基を除く)であることが好ましい。炭素数1の炭化水素基の例として、-CH2-、枝分かれ構造を有する-CH=または枝分かれ構造を有する-C≡が挙げられる。
[式中、Y’は、直接結合、-O-、-NH-または-S(=O)2-であり、
R’は-(CH2)m-(mは1~5の整数である)または-C6H4-(フェニレン基)である。]
であってよい。
[式中、mは1~5の整数、特に2または4である。]
であることが好ましい。Y1は、-O-または-O-(CH2)m-NH-C(=O)-、特に-O-(CH2)m-NH-C(=O)-であることがより好ましい。
(a1)式:
CH2=C(-X2-C(=O)-Y2-R2
[式中、R2は、炭素数7~40の炭化水素基であり、
X2は、水素原子、一価の有機基またはハロゲン原子であり、
Y2は、-O-または-NH-である。]
で示されるアクリル単量体、および
(a2)式:
CH2=C(-X3)-C(=O)-Y3-Z(-Y4-R3)n
[式中、R3は、それぞれ独立的に、炭素数7~40の炭化水素基であり、
X3は、水素原子、一価の有機基またはハロゲン原子であり、
Y3は、-O-または-NH-であり、
Y4は、それぞれ独立的に、直接結合、あるいは-O-、-C(=O)-、-S(=O)2-、-NH-または-CH2-から選ばれる少なくとも1つ以上で構成される基であり、
Zは、2価または3価の炭素数1~5の炭化水素基であり、
nは、1または2である。]
で示されるアクリル単量体である。
アクリル単量体(a1)は、式:
CH2=C(-X2)-C(=O)-Y2-R2
[式中、R2は、炭素数7~40の炭化水素基であり、
X2は、水素原子、一価の有機基またはハロゲン原子であり、
Y2は、-O-または-NH-である。]
で示される化合物である。
R2は、脂肪族炭化水素基、特に飽和の脂肪族炭化水素基、特別にアルキル基であることが好ましい。R2において、炭化水素基の炭素数は、12~30、例えば16~26、特に18~22であることが好ましい。
X2は、水素原子、メチル基、フッ素原子を除くハロゲン、置換または非置換のベンジル基、置換または非置換のフェニル基であってよい。水素原子、メチル基または塩素原子であることが好ましい。
長鎖アクリルアミド単量体の好ましい具体例は、ステアリル(メタ)アクリルアミド、イコシル(メタ)アクリルアミド、ベヘニル(メタ)アクリルアミドである。
アクリル単量体(a2)は、アクリル単量体(a1)とは異なる単量体である。アクリル単量体(a2)は、-O-、-C(=O)-、-S(=O)2-、-NH-または-CH2-から選ばれる少なくとも1つ以上で構成される基を有する(メタ)アクリレートまたは(メタ)アクリルアミドである。
アクリル単量体(a2)は、式:
CH2=C(-X3)-C(=O)-Y3-Z(-Y4-R3)n
[式中、R3は、それぞれ独立的に、炭素数7~40の炭化水素基であり、
X3は、水素原子、一価の有機基またはハロゲン原子であり、
Y3は、-O-または-NH-であり、
Y4は、それぞれ独立的に、直接結合、あるいは-O-、-C(=O)-、-S(=O)2-、-NH-または-CH2-から選ばれる少なくとも1つ以上で構成される基であり、
Zは、直接結合、あるいは2価または3価の炭素数1~5の炭化水素基であり、
nは、1または2である。]
で示される化合物であってよい。
[式中、Y’はそれぞれ独立して、直接結合、-O-、-NH-または-S(=O)2-であり、
R’は-(CH2)m-(mは1~5の整数である)、炭素数1~5の不飽和結合を有する直鎖状の炭化水素基、炭素数1~5の枝分かれ構造を有する炭化水素基、または-(CH2)l-C6H4-(CH2)l-(lはそれぞれ独立して0~5の整数であり-C6H4-はフェニレン基である)である。]
であってよい。
[式中、mは1~5の整数である。]
である。
Zは直接結合でないことが好ましく、Y4およびZは同時に直接結合であることはない。
アクリル単量体(a2)は、CH2=C(-X3)-C(=O)-O-(CH2)m-NH-C(=O)-R3であることが特に好ましい。
あるいは、アクリル単量体(a2)は、側鎖にイソシアネート基を有する(メタ)アクリレート、例えば、2-メタクリロイルオキシエチルメタクリレートと長鎖アルキルアミンまたは長鎖アルキルアルコールを反応させることでも製造できる。長鎖アルキルアミンとしては例えば、ラウリルアミン、ミリスチルアミン、セチルアミン、ステアリルアミン、オレイルアミン、ベヘニルアミンなどがある。長鎖アルキルアルコールとしては例えば、ラウリルアルコール、ミリスチルアルコール、セチルアルコール、ステアリルアルコール、オレイルアルコール、ベヘニルアルコールなどがある。
ステアリル(メタ)アクリレート、ベヘニル(メタ)アクリレート、ステアリルαクロロアクリレート、ベヘニルαクロロアクリレート;
ステアリル(メタ)アクリルアミド、ベヘニル(メタ)アクリルアミド;
[上記式中、nは7~40の数であり、mは1~5の数である。]
上記の化学式の化合物は、α位が水素原子であるアクリル化合物であるが、具体例は、α位がメチル基であるメタクル化合物およびα位が塩素原子であるαクロロアクリル化合物であってよい。
R12-C(=O)-NH-R13-O-R11
[式中、R11は、エチレン性不飽和重合性基を有する有機残基、
R12は、炭素数7~40の炭化水素基、
R13は、炭素数1~5の炭化水素基である。]
で示されるアミド基含有単量体であることが好ましい。
アミド基含有単量体の具体例としては、パルミチン酸アミドエチル(メタ)アクリレート、ステアリン酸アミドエチル(メタ)アクリレート、ベヘニン酸アミドエチル(メタ)アクリレート、ミリスチン酸アミドエチル(メタ)アクリレート、ラウリン酸アミドエチル(メタ)アクリレート、イソステアリン酸エチルアミド(メタ)アクリレート、オレイン酸エチルアミド(メタ)アクリレート、ターシャリーブチルシクロヘキシルカプロン酸アミドエチル(メタ)アクリレート、アダマンタンカルボン酸エチルアミド(メタ)アクリレート、ナフタレンカルボン酸アミドエチル(メタ)アクリレート、アントラセンカルボン酸アミドエチル(メタ)アクリレート、パルミチン酸アミドプロピル(メタ)アクリレート、ステアリン酸アミドプロピル(メタ)アクリレート、パルミチン酸アミドエチルビニルエーテル、ステアリン酸アミドエチルビニルエーテル、パルミチン酸アミドエチルアリルエーテル、ステアリン酸アミドエチルアリルエーテル、またはこれらの混合物が挙げられる。
親水性基を有するアクリル単量体(b)は、単量体(a)以外の単量体であって、親水性単量体である。親水性基は、オキシアルキレン基(アルキレン基の炭素数は2~6である。)であることが好ましい。特に、親水性基を有するアクリル単量体(b)は、オキシアルキレン(メタ)アクリレート、例えば、ポリアルキレン(またはモノアルキレン)グリコールモノ(メタ)アクリレートおよび/またはポリアルキレン(またはモノアルキレン)グリコールジ(メタ)アクリレート、ポリアルキレン(またはモノアルキレン)グリコールモノ(メタ)アクリルアミドであることが好ましい。
CH2=CX11C(=O)-Y11-(RO)n-A
[式中、
X11は、水素原子またはメチル基であり、
Y11は、-O-または-NH-であり、
Rは、炭素数2~6のアルキレン基、
Aは、水素原子、炭素数1~22の不飽和または飽和の炭化水素基、またはCH2=CX11C(=O)-(ただし、X11は、水素原子またはメチル基である。)であり、
nは、1~90の整数である。]
で示されるオキシアルキレン(メタ)アクリレートであることが好ましい。
CH2=CX11C(=O)-O-(RO)n-X12 (b1)
および
CH2=CX11C(=O)-O-(RO)n-C(=O)CX11=CH2 (b2)、
CH2=CX11C(=O)-NH-(RO)n-X12 (b3)
[式中、
X11は、各々独立に水素原子またはメチル基、
X12は、各々独立に水素原子または炭素数1~22の不飽和または飽和の炭化水素基、
Rは、炭素数2~6のアルキレン基、
nは、1~90の整数
である。]
で示されるオキシアルキレン(メタ)アクリレートであることが好ましい。nは、例えば1~50、特に1~30、特別に1~15あるいは2~15であってよい。あるいは、nは、例えば1であってよい。
Rは、直鎖または分岐のアルキレン基であってよく、例えば、式-(CH2)x-または-(CH2)x1-(CH(CH3))x2-[式中、x1およびx2は0~6、例えば2~5であり、x1およびx2の合計は1~6である。-(CH2)x1-と-(CH(CH3))x2-の順序は、記載の式に限定されず、ランダムであってもよい。]で示される基であってよい。
-(RO)n-において、Rは2種類以上(例えば、2~4種類、特に2種類)であってよく、-(RO)n-は、例えば、-(R1O)n1-と-(R2O)n2-[式中、R1とR2は、相互に異なって、炭素数2~6のアルキレン基であり、n1およびn2は、1以上の数であり、n1とn2の合計は2~90である。]の組み合わせであってよい。
CH2=CHCOO-CH2CH2O-H
CH2=CHCOO-CH2CH2CH2O-H
CH2=CHCOO-CH2CH(CH3)O-H
CH2=CHCOO-CH(CH3)CH2O-H
CH2=CHCOO-CH2CH2CH2CH2O-H
CH2=CHCOO-CH2CH2CH(CH3)O-H
CH2=CHCOO-CH2CH(CH3)CH2O-H
CH2=CHCOO-CH(CH3)CH2CH2O-H
CH2=CHCOO-CH2CH(CH2CH3)O-H
CH2=CHCOO-CH2C(CH3)2O-H
CH2=CHCOO-CH(CH2CH3)CH2O-H
CH2=CHCOO-C(CH3)2CH2O-H
CH2=CHCOO-CH(CH3)CH(CH3)O-H
CH2=CHCOO-C(CH3)(CH2CH3)O-H
CH2=CHCOO-(CH2CH2O)2-H
CH2=CHCOO-(CH2CH2O)4-H
CH2=CHCOO-(CH2CH2O)5-H
CH2=CHCOO-(CH2CH2O)6-H
CH2=CHCOO-(CH2CH2O)5-CH3
CH2=CHCOO-(CH2CH2O)9-CH3
CH2=CHCOO-(CH2CH2O)23-CH3
CH2=CHCOO-(CH2CH2O)90-CH3
CH2=CHCOO-(CH2CH(CH3)O)9-CH3
CH2=CHCOO-(CH2CH(CH3)O)12-CH3
CH2=CHCOO-(CH2CH2O)5-(CH2CH(CH3)O)2-H
CH2=CHCOO-(CH2CH2O)5-(CH2CH(CH3)O)3-CH3
CH2=CHCOO-(CH2CH2O)8-(CH2CH(CH3)O)6-CH2CH(C2H5)C4H9
CH2=CHCOO-(CH2CH2O)23-OOC(CH3)C=CH2
CH2=CHCOO-(CH2CH2O)20-(CH2CH(CH3)O)5-CH2-CH=CH2
CH2=C(CH3)COO-CH2CH2O-H
CH2=C(CH3)COO-CH2CH2CH2O-H
CH2=C(CH3)COO-CH2CH(CH3)O-H
CH2=C(CH3)COO-CH(CH3)CH2O-H
CH2=C(CH3)COO-CH2CH2CH2CH2O-H
CH2=C(CH3)COO-CH2CH2CH(CH3)O-H
CH2=C(CH3)COO-CH2CH(CH3)CH2O-H
CH2=C(CH3)COO-CH(CH3)CH2CH2O-H
CH2=C(CH3)COO-CH2CH(CH2CH3)O-H
CH2=C(CH3)COO-CH2C(CH3)2O-H
CH2=C(CH3)COO-CH(CH2CH3)CH2O-H
CH2=C(CH3)COO-C(CH3)2CH2O-H
CH2=C(CH3)COO-CH(CH3)CH(CH3)O-H
CH2=C(CH3)COO-C(CH3)(CH2CH3)O-H
CH2=C(CH3)COO-(CH2CH2O)2-H
CH2=C(CH3)COO-(CH2CH2O)4-H
CH2=C(CH3)COO-(CH2CH2O)5-H
CH2=C(CH3)COO-(CH2CH2O)6-H
CH2=C(CH3)COO-(CH2CH2O)9-H
CH2=C(CH3)COO-(CH2CH2O)5-CH3
CH2=C(CH3)COO-(CH2CH2O)9-CH3
CH2=C(CH3)COO-(CH2CH2O)23-CH3
CH2=C(CH3)COO-(CH2CH2O)90-CH3
CH2=C(CH3)COO-(CH2CH(CH3)O)9-H
CH2=C(CH3)COO-(CH2CH(CH3)O)12-CH3
CH2=C(CH3)COO-(CH2CH2O)5-(CH2CH(CH3)O)2-H
CH2=C(CH3)COO-(CH2CH2O)5-(CH2CH(CH3)O)3-CH3
CH2=C(CH3)COO-(CH2CH2O)8-(CH2CH(CH3)O)6-CH2CH(C2H5)C4H9
CH2=C(CH3)COO-(CH2CH2O)23-OOC(CH3)C=CH2
CH2=C(CH3)COO-(CH2CH2O)20-(CH2CH(CH3)O)5-CH2-CH=CH2
CH2=CH-C(=O)-NH-CH2CH2CH2O-H
CH2=CH-C(=O)-NH-CH2CH(CH3)O-H
CH2=CH-C(=O)-NH-CH(CH3)CH2O-H
CH2=CH-C(=O)-NH-CH2CH2CH2CH2O-H
CH2=CH-C(=O)-NH-CH2CH2CH(CH3)O-H
CH2=CH-C(=O)-NH-CH2CH(CH3)CH2O-H
CH2=CH-C(=O)-NH-CH(CH3)CH2CH2O-H
CH2=CH-C(=O)-NH-CH2CH(CH2CH3)O-H
CH2=CH-C(=O)-NH-CH2C(CH3)2O-H
CH2=CH-C(=O)-NH-CH(CH2CH3)CH2O-H
CH2=CH-C(=O)-NH-C(CH3)2CH2O-H
CH2=CH-C(=O)-NH-CH(CH3)CH(CH3)O-H
CH2=CH-C(=O)-NH-C(CH3)(CH2CH3)O-H
CH2=CH-C(=O)-NH-(CH2CH2O)2-H
CH2=CH-C(=O)-NH-(CH2CH2O)4-H
CH2=CH-C(=O)-NH-(CH2CH2O)5-H
CH2=CH-C(=O)-NH-(CH2CH2O)6-H
CH2=CH-C(=O)-NH-(CH2CH2O)9-H
CH2=CH-C(=O)-NH-(CH2CH2O)5-CH3
CH2=CH-C(=O)-NH-(CH2CH2O)9-CH3
CH2=CH-C(=O)-NH-(CH2CH2O)23-CH3
CH2=CH-C(=O)-NH-(CH2CH2O)90-CH3
CH2=CH-C(=O)-NH-(CH2CH(CH3)O)9-CH3
CH2=CH-C(=O)-NH-(CH2CH(CH3)O)12-CH3
CH2=CH-C(=O)-NH-(CH2CH2O)5-(CH2CH(CH3)O)2-H
CH2=CH-C(=O)-NH-(CH2CH2O)5-(CH2CH(CH3)O)3-CH3
CH2=CH-C(=O)-NH-(CH2CH2O)8-(CH2CH(CH3)O)6-CH2CH(C2H5)C4H9
CH2=C(CH3)-C(=O)-NH-CH2CH2CH2O-H
CH2=C(CH3)-C(=O)-NH-CH2CH(CH3)O-H
CH2=C(CH3)-C(=O)-NH-CH(CH3)CH2O-H
CH2=C(CH3)-C(=O)-NH-CH2CH2CH2CH2O-H
CH2=C(CH3)-C(=O)-NH-CH2CH2CH(CH3)O-H
CH2=C(CH3)-C(=O)-NH-CH2CH(CH3)CH2O-H
CH2=C(CH3)-C(=O)-NH-CH(CH3)CH2CH2O-H
CH2=C(CH3)-C(=O)-NH-CH2CH(CH2CH3)O-H
CH2=C(CH3)-C(=O)-NH-CH2C(CH3)2O-H
CH2=C(CH3)-C(=O)-NH-CH(CH2CH3)CH2O-H
CH2=C(CH3)-C(=O)-NH-C(CH3)2CH2O-H
CH2=C(CH3)-C(=O)-NH-CH(CH3)CH(CH3)O-H
CH2=C(CH3)-C(=O)-NH-C(CH3)(CH2CH3)O-H
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)2-H
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)4-H
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)5-H
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)6-H
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)9-H
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)5-CH3
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)9-CH3
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)23-CH3
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)90-CH3
CH2=C(CH3)-C(=O)-NH-(CH2CH(CH3)O)9-CH3
CH2=C(CH3)-C(=O)-NH-(CH2CH(CH3)O)12-CH3
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)5-(CH2CH(CH3)O)2-H
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)5-(CH2CH(CH3)O)3-CH3
CH2=C(CH3)-C(=O)-NH-(CH2CH2O)8-(CH2CH(CH3)O)6-CH2CH(C2H5)C4H9
イオン供与基を有する単量体(c)は、単量体(a)および単量体(b)以外の単量体である。単量体(c)は、オレフィン性炭素―炭素二重結合およびイオン供与基を有する単量体であることが好ましい。イオン供与基は、アニオン供与基および/またはカチオン供与基である。
CH2=CHCOO-CH2CH2-N(CH3)2 およびその塩(例えば酢酸塩)
CH2=CHCOO-CH2CH2-N(CH2CH3)2 およびその塩(例えば酢酸塩)
CH2=C(CH3)COO-CH2CH2-N(CH3)2 およびその塩(例えば酢酸塩)
CH2=C(CH3)COO-CH2CH2-N(CH2CH3)2 およびその塩(例えば酢酸塩)
CH2=CHC(O)N(H)-CH2CH2CH2-N(CH3)2 およびその塩(例えば酢酸塩)
CH2=CHCOO-CH2CH2-N(-CH3)(-CH2-C6H5) およびその塩(例えば酢酸塩)
CH2=C(CH3)COO-CH2CH2-N(-CH2CH3)(-CH2-C6H5)およびその塩(例えば酢酸塩)
CH2=CHCOO-CH2CH2-N+(CH3)3Cl-
CH2=CHCOO-CH2CH2-N+(-CH3)2(-CH2-C6H5)Cl-
CH2=C(CH3)COO-CH2CH2-N+(CH3)3Cl-
CH2=CHCOO-CH2CH(OH)CH2-N+(CH3)3Cl-
CH2=C(CH3)COO-CH2CH(OH)CH2-N+(CH3)3Cl-
CH2=C(CH3)COO-CH2CH(OH)CH2-N+(-CH2CH3)2(-CH2-C6H5)Cl-
CH2=C(CH3)COO-CH2CH2-N+(CH3)3Br-
CH2=C(CH3)COO-CH2CH2-N+(CH3)3I-
CH2=C(CH3)COO-CH2CH2-N+(CH3)3O-SO3CH3
CH2=C(CH3)COO-CH2CH2-N+(CH3)(-CH2-C6H5)2Br-
他の単量体(d)は、単量体(a)、(b)および(c)以外の単量体である。そのような他の単量体としては、エチレン、酢酸ビニル、塩化ビニル、フッ化ビニル、ハロゲン化ビニルスチン、α-メチルスチレン、p-メチルスチレン、ポリオキシアルキレンモノ(メタ)アクリレート、(メタ)アクリルアミド、ジアセトン(メタ)アクリルアミド、メチロール化(メタ)アクリルアミド、N-メチロール(メタ)アクリルアミド、アルキルビニルエーテル、ハロゲン化アルキルビニルエーテル、アルキルビニルケトン、ブタジエン、イソプレン、クロロプレン、グリシジル(メタ)アクリレート、アジリジニル(メタ)アクリレート、ベンジル(メタ)アクリレート、イソシアネートエチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、短鎖アルキル(メタ)アクリレート、無水マレイン酸、ポリジメチルシロキサン基を有する(メタ)アクリレート、N-ビニルカルバゾールが挙げられる。
単量体(b)から形成される繰り返し単位(繰り返し単位(b))の量は、非フッ素共重合体に対して(または繰り返し単位(a)と繰り返し単位(b)の合計に対して)、5~70重量%または10~70重量%、好ましくは8~50重量%、より好ましくは10~40重量%であってよい。
単量体(c)から形成される繰り返し単位の量は、非フッ素共重合体に対して、0.1~30重量%、好ましくは0.5~20重量%、より好ましくは1~15重量%であってよい。
単量体(d)から形成される繰り返し単位の量は、非フッ素共重合体に対して、0~20重量%、例えば1~15重量%、特に2~10重量%であってよい。
本明細書において、「(メタ)アクリル」とは、アクリルまたはメタクリルを意味する。例えば、「(メタ)アクリレート」とは、アクリレートまたはメタクリレートを意味する。
非フッ素共重合体の融点またはガラス転移点は、好ましくは20℃以上、より好ましくは30℃以上、特に好ましくは35℃以上、例えば40℃以上である。
本開示においては、重合(例えば、溶液重合または乳化重合、好ましくは溶液重合)後、水を加えてから脱溶剤して、重合体を水に分散させることが好ましい。乳化剤を加える必要なく、自己分散型の製品を製造することができる。
油溶性重合開始剤の具体例としては、2,2’-アゾビス(2-メチルプロピオニトリル)、2,2’-アゾビス(2-メチルブチロニトリル)、2,2’-アゾビス(2、4-ジメチルバレロニトリル)、2,2’-アゾビス(2、4-ジメチル4-メトキシバレロニトリル)、1,1’-アゾビス(シクロヘキサン-1-カルボニトリル)、ジメチル2,2’-アゾビス(2-メチルプロピオネート)、2,2’-アゾビス(2-イソブチロニトリル)、ベンゾイルパーオキシド、ジ-第三級-ブチルパーオキシド、ラウリルパーオキシド、クメンヒドロパーオキシド、t-ブチルパーオキシピバレート、ジイソプロピルパーオキシジカーボネート、過ピバル酸t-ブチル等が好ましく挙げられる。
重合開始剤は単量体100重量部に対して、0.01~5重量部の範囲で用いられる。
溶液重合では、単量体を有機溶剤に溶解させ、窒素置換後、重合開始剤を添加して、例えば40~120℃の範囲で1~10時間、加熱撹拌する方法が採用される。重合開始剤は、一般に、油溶性重合開始剤であってよい。
ならびに
油溶性重合開始剤、例えば、2,2’-アゾビス(2-メチルプロピオニトリル)、2,2’-アゾビス(2-メチルブチロニトリル)、2,2’-アゾビス(2、4-ジメチルバレロニトリル)、2,2’-アゾビス(2、4-ジメチル4-メトキシバレロニトリル)、1,1’-アゾビス(シクロヘキサン-1-カルボニトリル)、ジメチル2,2’-アゾビス(2-メチルプロピオネート)、2,2’-アゾビス(2-イソブチロニトリル)、ベンゾイルパーオキシド、ジ-第三級-ブチルパーオキシド、ラウリルパーオキシド、クメンヒドロパーオキシド、t-ブチルパーオキシピバレート、ジイソプロピルパーオキシジカーボネート、過ピバル酸t-ブチル
が用いられる。重合開始剤は単量体100重量部に対して、0.01~10重量部の範囲で用いられる。
多糖類と耐油性ポリマーとの重量比は、10:90~98:2、例えば40:60~95:5または55:45~90:10、特に70:30~95:5、80:20~93:7、特別に82:18~93:7または88:12~92:8であってよい。
紙を加工するための処理液は、50℃において、200cps以下、例えば150cps以下、100cps以下または80cps以下の粘度を有することが好ましい。粘度の下限は1cpsであってよい。
耐油剤は、従来既知の方法により被処理物に適用することができる。通常、耐油剤を有機溶剤または水に分散して希釈して、浸漬塗布、スプレー塗布、泡塗布などのような既知の方法により、被処理物の表面に付着させ、乾燥する方法が採られる(表面処理)。
被処理物の紙基材としては、紙、紙でできた容器、紙でできた成形体(例えばパルプモールド)などが挙げられる。食品包装材および食品容器が好ましい。
多糖類および耐油性ポリマーは、紙基材に良好に付着する。
1つの塗布方式は、2本のゴムロールの間に紙を通して形成されるニップ部に塗布液(サイズ液)を供給し、ポンドと呼ばれる塗液溜りを作り、この塗液溜りに紙を通して紙の両面にサイズ液を塗布する、いわゆるポンド式ツーロールサイズプレスである。他の塗布方式は、サイズ液を表面転写型により塗布するゲートロール型、及び、ロッドメタリングサイズプレスである。ポンド式ツーロールサイズプレスにおいてサイズ液は紙の内部まで浸透しやすく、表面転写型においてサイズ液成分は紙の表面に留まりやすい。表面転写型は、ポンド式ツーロールサイズプレスと比べて、塗布層が紙の表面に留まりやすく、表面に形成される耐油層がポンド式ツーロールサイズプレスより多い。
本開示では、前者のポンド式2ロールサイズプレスを用いた場合でも紙に耐油性能を付与できる。
このように処理された紙は、室温または高温での簡単な乾燥後に、任意に、紙の性質に依存して300℃まで、例えば200℃まで、特に80℃~180℃の温度範囲をとり得る熱処理を伴うことで、優れた耐油性および耐水性を示す。
晒あるいは未晒高収率パルプ、新聞古紙、雑誌古紙、段ボール古紙あるいは脱墨古紙等の古紙パルプのいずれも使用することができる。また、上記パルプ原料と石綿、ポリアミド、ポリイミド、ポリエステル、ポリオレフィン、ポリビニルアルコール等の合成繊維との混合物も使用することができる。
必要により、ポリビニルアルコール、グルコース、染料、コーティングカラー、防滑剤等を用いて、サイズプレス、ゲートロールコーター、ビルブレードコーター、キャレンダー等によって、耐油剤を紙に塗布することができる。
添加剤として、ポリビニルアルコールまたはグルコースを使用することが好ましい。ポリビニルアルコールまたはグルコースを多糖類とともに用いることにより、高い耐油性が得られる。ポリビニルアルコールの量は、多糖類100重量部に対して、1~1000重量部、2~200重量部、3~100重量部または5~50重量部、特に10~40重量部であってよい。
内添においては、紙を形成するパルプ100重量部に対して、耐油剤の量が0.01~50重量部または0.01~30重量部、例えば0.01~10重量部、特に0.2~5.0重量部となるように、耐油剤をパルプと混合することが好ましい。
外添および内添において、多糖類と非フッ素共重合体との重量比は、10:90~98:2、例えば40:60~95:5または55:45~90:10であってよい。多糖類と添加剤との重量比は、70:30~99:1、80:20~95:5または85:15~90:10であってよい。
以下において、部、%または比は、特記しない限り、重量部、重量%または重量比を表す。
回転体が流体から受ける抵抗(粘性抵抗)を回転トルクなどから読み取る回転式粘度計(B型)を使用して、粘度(cps)を測定した。
耐油性(KIT法)は、TAPPI T-559cm-02に従って測定した。KIT試験液はひまし油、トルエン、ヘプタンを表1の比率で混合した試験液である。表1に示す試験液1滴を紙の上におき、15秒後に油の浸透状態を観察した。浸透を示さないKIT試験液が与える耐油度の最高点を耐油性とした。KIT試験液の番号が高いほど耐油性が高い。
撹拌装置、温度計、還流冷却器、滴下漏斗、窒素流入口および加熱装置を備えた容積500mlの反応器を用意し、溶媒のメチルエチルケトン(MEK)を100部添加した。続いて、撹拌下、ステアリン酸アミドエチルアクリレート(C18AmEA、融点:70℃)78部、ヒドロキシエチルアクリレート(HEA)16部、およびジメチルアミノエチルメタクリレート(DM)6部からなる単量体(単量体計100部)、および開始剤のパーブチルPV(PV)1.2部をこの順に添加し、この混合物を65-75℃の窒素雰囲気下で12時間混合撹拌して共重合を行った。得られた共重合体含有溶液の固形分濃度は50重量%であった。
後処理として、得られた共重合体溶液の50gに0.4%の酢酸水溶液142gを添加し、分散させた後、エバポレーターを用いて加熱しながら減圧下でMEKを留去し、乳白色の共重合水分散液(揮発性有機溶媒の含有量は1重量%以下)を得た。この水分散液にさらにイオン交換水を加えて固形分濃度15重量%である水分散液を得た。
この共重合体の融点は、64℃であった。
得られた共重合体の分子量をゲルパーミエーションクロマトグラフィーで分析したところ、ポリスチレン換算の質量平均分子量は900,000であった。
木材パルプとして、LBKP(=広葉樹さらしクラフトパルプ)とNBKP(針葉樹さらしクラフトパルプ)の重量比率が、60重量%と40重量%で、かつ、パルプのろ水度が400ml(Canadian Standard Freeness)のパルプスラリーを調整し、このパルプスラリーに湿潤紙力剤を乾燥パルプに対して固形分濃度で0.5重量%添加して長網抄紙機により、紙密度が0.58g/cm3の坪量45g/m2の紙を外添処理(サイズプレス処理)の原紙として使用した。またこの原紙の耐油性(KIT値)は0、耐水性(Cobb値)は52g/m2であった。
合成例1で得られた共重合体の水分散液を耐油剤として用い、以下の処方により、耐油紙(加工紙)を得た。
処理液は、合成例1で得られた共重合体の水分散液を固形分濃度が1.5重量%、かつ、澱粉の固形分濃度が7%となるように調整し、サイズプレス機で処理した後、ドラムドライヤーで乾燥し、耐油紙(加工紙)を得た。得られた耐油紙の澱粉と共重合体の固形分の塗工量は0.8g/m2(共重合体の塗工量は0.14g/m2)であった。得られた原紙を試験紙として用い、キット試験(Kit Test)を行った。評価結果を表2に示す。
ここで記載した澱粉は、ヒドロキシエチル化変性澱粉(10重量%の50℃での粘度が11cps)を使用した。ここで記載したサイズプレス処理(Mathis社製のサイズプレス機を使用)とは、ロールとロールの間に処理液をため、任意のロールスピードとニップ圧で、ロール間の処理液に原紙を通す、いわゆるポンド式2ロールサイズプレス処理のことである。
処理液中の澱粉濃度を10重量%用いる他は、実施例1と同様の処理を行った。
得られた耐油紙の澱粉と共重合体の固形分の塗工量は1.2g/m2(共重合体の塗工量は0.16g/m2)であった。キット試験の結果を表2に示す。
処理液中の澱粉濃度を14重量%用いる他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は1.8/m2(共重合体の塗工量は0.17g/m2)であった。キット試験の結果を表2に示す。
実施例1のヒドロキシエチル化変性澱粉に代えて、酸化澱粉(10重量%の50℃での粘度が26cps)を用いる他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は0.8/m2(共重合体の塗工量は0.14g/m2)であった。キット試験の結果を表2に示す。
実施例1のヒドロキシエチル化変性澱粉に代えて、オクテニルコハク酸変性澱粉(10重量%の50℃での粘度が7cps)を用いる他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は0.8/m2(共重合体の塗工量は0.14g/m2)であった。キット試験の結果を表2に示す。
処理液中の澱粉濃度を14重量%用いる他は、実施例5と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は1.8g/m2(共重合体の塗工量は0.17g/m2)であった。キット試験の結果を表2に示す。
実施例1のヒドロキシエチル化変性澱粉に代えて、デキストリン(10重量%の50℃での粘度が3cps)を30重量%用いる他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は4.0/m2(共重合体の塗工量は0.19g/m2)であった。キット試験の結果を表2に示す。
実施例1のヒドロキシエチル化変性澱粉に代えて、カチオン化変性澱粉(10重量%の50℃での粘度が80cps)を5重量%用いる他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は0.6/m2(共重合体の塗工量は0.15g/m2)であった。キット試験の結果を表2に示す。
実施例1にポリビニルアルコール2重量%を加える他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は1.2/m2(共重合体の塗工量は0.17g/m2)であった。キット試験の結果を表2に示す。
実施例1にオクテニルコハク酸変性澱粉7重量%を加える他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は1.9g/m2(共重合体の塗工量は0.18g/m2)であった。キット試験の結果を表2に示す。
共重合体を用いない他は、実施例10と同様の処理を行った。得られた耐油紙の固形分の塗工量は1.8g/m2であった。キット試験の結果を表2に示す。
実施例1のヒドロキシエチル化変性澱粉に代えて、アルファ化澱粉A(25重量%の50℃での粘度が41cps)を25重量%用いる他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は1.9/m2(共重合体の塗工量は0.11g/m2)であった。キット試験の結果を表2に示す。
実施例1のヒドロキシエチル化変性澱粉に代えて、アルファ化澱粉B(30重量%の50℃での粘度が22cps)を30重量%用いる他は、実施例1と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は2.1/m2(共重合体の塗工量は0.10g/m2)であった。キット試験の結果を表2に示す。
実施例3にグルコース10重量%を加える他は、実施例3と同様の処理を行った。得られた耐油紙の澱粉と共重合体の固形分の塗工量は1.9/m2(共重合体の塗工量は0.14g/m2)であった。キット試験の結果を表2に示す。
Claims (15)
- (1)多糖類および(2)耐油性ポリマーを含んでなる耐油組成物。
- 耐油性ポリマー(2)が、
(a)炭素数7~40の長鎖炭化水素基を有するアクリル単量体から形成された繰り返し単位、および
(b)親水性基を有するアクリル単量体から形成された繰り返し単位
を有する非フッ素共重合体であり、
多糖類と耐油性ポリマーとの重量比が、10:90~98:2である請求項1に記載の耐油組成物。 - 長鎖炭化水素基を有するアクリル単量体(a)が、式:
CH2=C(-X1)-C(=O)-Y1(R1)k
[式中、R1は、それぞれ独立的に、炭素数7~40の炭化水素基であり、
X1は、水素原子、一価の有機基またはハロゲン原子であり、
Y1は、2価~4価の炭素数1の炭化水素基、-C6H4-、-O-、-C(=O)-、-S(=O)2-または-NH-から選ばれる少なくとも1つ以上で構成される基(但し、炭化水素基を除く)であり、
kは1~3である。]
で示される単量体である請求項2に記載の耐油組成物。 - 長鎖炭化水素基を有するアクリル単量体(a)が、
(a1)式:
CH2=C(-X2)-C(=O)-Y2-R2
[式中、R2は、炭素数7~40の炭化水素基であり、
X2は、水素原子、一価の有機基またはハロゲン原子であり、
Y2は、-O-または-NH-である。]
で示されるアクリル単量体、および/または
(a2)式:
CH2=C(-X3)-C(=O)-Y3-Z(-Y4-R3)n
[式中、R3は、それぞれ独立的に、炭素数7~40の炭化水素基であり、
X3は、水素原子、一価の有機基またはハロゲン原子であり、
Y3は、-O-または-NH-であり、
Y4は、それぞれ独立的に、直接結合、-O-、-C(=O)-、-S(=O)2-、-NH-または-CH2-から選ばれる少なくとも1つ以上で構成される基であり、
Zは、直接結合、あるいは2価または3価の炭素数1~5の炭化水素基であり、
nは、1または2である。]
で示されるアクリル単量体であり、
親水性基を有するアクリル単量体(b)が、式:
CH2=CX11C(=O)-Y11-(RO)n-A
[式中、
X11は、水素原子またはメチル基であり、
Y11は、-O-または-NH-であり、
Rは、炭素数2~6のアルキレン基、
Aは、水素原子、炭素数1~22の不飽和または飽和の炭化水素基、またはCH2=CX11C(=O)-(ただし、X11は、水素原子またはメチル基である。)であり、
nは、1~90の整数である。]
で示されるオキシアルキレン(メタ)アクリレートである、請求項2または3に記載の耐油組成物。 - 水または水と有機溶媒の混合物である液状媒体をさらに含んでなる請求項1~4のいずれかに記載の耐油組成物。
- 2種以上の多糖類の組み合わせを含んでなる紙用耐油剤。
- 少なくとも1種の多糖類が、疎水化変性澱粉であるか、またはヒドロキシアルキル化澱粉、酸化澱粉、アルケニルコハク酸エステル化澱粉、デキストリン、カチオン化澱粉およびアルファ化澱粉からなる群から選択された少なくとも1種の澱粉であり、紙の外添に用いる請求項6に記載の紙用耐油剤。
- 請求項1~5のいずれかに記載の耐油組成物または請求項6または7に記載の紙用耐油剤と水から形成されており、粘度が200cps以下である処理液。
- 耐油層を形成させるために用いる請求項8記載の処理液。
- 処理液における多糖類の量が、5重量%以上である請求項8または9記載の処理液。
- 添加剤をも含む請求項8~10のいずれかに記載の処理液。
- 添加剤が、ポリビニルアルコールおよびグルコースから選択された少なくとも1種である請求項11に記載の処理液。
- 請求項1~5のいずれかに記載の耐油組成物または請求項6または7に記載の紙用耐油剤から形成された耐油層を紙の表面に有する耐油紙。
- 食品包装材または食品容器である請求項13に記載の耐油紙。
- 請求項1~5のいずれかに記載の耐油組成物または請求項6または7に記載の紙用耐油剤で紙を外添処理または内添処理により処理する紙の処理方法。
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WO2020241709A1 (ja) * | 2019-05-28 | 2020-12-03 | ダイキン工業株式会社 | 紙用耐油剤 |
JP2021046522A (ja) * | 2019-09-20 | 2021-03-25 | Dicグラフィックス株式会社 | 水性ニス組成物及び塗工物 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2024080310A1 (ja) | 2022-10-12 | 2024-04-18 | ダイキン工業株式会社 | 撥水撥油剤 |
WO2024080309A1 (ja) | 2022-10-12 | 2024-04-18 | ダイキン工業株式会社 | 撥水撥油剤 |
JP7553834B2 (ja) | 2022-10-12 | 2024-09-19 | ダイキン工業株式会社 | 撥水撥油剤 |
JP7553835B2 (ja) | 2022-10-12 | 2024-09-19 | ダイキン工業株式会社 | 撥水撥油剤 |
WO2024172158A1 (ja) * | 2023-02-17 | 2024-08-22 | ダイキン工業株式会社 | 耐油剤 |
Also Published As
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TW202223007A (zh) | 2022-06-16 |
JP2022065650A (ja) | 2022-04-27 |
JP7502668B2 (ja) | 2024-06-19 |
EP4230667A1 (en) | 2023-08-23 |
CN116323710A (zh) | 2023-06-23 |
US20230250589A1 (en) | 2023-08-10 |
JP7397365B2 (ja) | 2023-12-13 |
KR20230068416A (ko) | 2023-05-17 |
JP2022103183A (ja) | 2022-07-07 |
EP4230667A8 (en) | 2023-10-11 |
JP2022103182A (ja) | 2022-07-07 |
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