JP7475758B1 - 耐油剤組成物及び耐油製品 - Google Patents
耐油剤組成物及び耐油製品 Download PDFInfo
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- JP7475758B1 JP7475758B1 JP2023564081A JP2023564081A JP7475758B1 JP 7475758 B1 JP7475758 B1 JP 7475758B1 JP 2023564081 A JP2023564081 A JP 2023564081A JP 2023564081 A JP2023564081 A JP 2023564081A JP 7475758 B1 JP7475758 B1 JP 7475758B1
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- unsaturated monomer
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- oil
- resistant
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- 239000000178 monomer Substances 0.000 claims abstract description 165
- 125000000524 functional group Chemical group 0.000 claims abstract description 96
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- 230000002378 acidificating effect Effects 0.000 claims abstract description 54
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 46
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- 239000011737 fluorine Substances 0.000 claims abstract description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 239000000758 substrate Substances 0.000 claims abstract description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 6
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- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
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- 125000005843 halogen group Chemical group 0.000 claims description 3
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- 239000004147 Sorbitan trioleate Substances 0.000 claims description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 claims description 2
- DPNIJLHSBNLPNW-UHFFFAOYSA-N ethyl carbamate;styrene Chemical compound CCOC(N)=O.C=CC1=CC=CC=C1 DPNIJLHSBNLPNW-UHFFFAOYSA-N 0.000 claims description 2
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- -1 polyethylene Polymers 0.000 description 60
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 10
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- 150000003839 salts Chemical class 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
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- VGIBGUSAECPPNB-UHFFFAOYSA-L nonaaluminum;magnesium;tripotassium;1,3-dioxido-2,4,5-trioxa-1,3-disilabicyclo[1.1.1]pentane;iron(2+);oxygen(2-);fluoride;hydroxide Chemical compound [OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[F-].[Mg+2].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[K+].[K+].[K+].[Fe+2].O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2.O1[Si]2([O-])O[Si]1([O-])O2 VGIBGUSAECPPNB-UHFFFAOYSA-L 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000013054 paper strength agent Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- FURYAADUZGZUGQ-UHFFFAOYSA-N phenoxybenzene;sulfuric acid Chemical class OS(O)(=O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 FURYAADUZGZUGQ-UHFFFAOYSA-N 0.000 description 1
- ORUWSEKEVGOAQR-UHFFFAOYSA-N phenyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OC1=CC=CC=C1 ORUWSEKEVGOAQR-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005646 polycarboxylate Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 235000013324 preserved food Nutrition 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XEZVDURJDFGERA-UHFFFAOYSA-N tricosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(O)=O XEZVDURJDFGERA-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- PLCFYBDYBCOLSP-UHFFFAOYSA-N tris(prop-2-enyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=CCOC(=O)CC(O)(CC(=O)OCC=C)C(=O)OCC=C PLCFYBDYBCOLSP-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- 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
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
- D21H19/20—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
Abstract
Description
項1. 炭素数1~60の炭化水素基と、中和された酸性官能基とを、少なくとも構成単位中に有する非フッ素系化合物を含み、かつ、
非フッ素系化合物は、前記中和された酸性官能基の占める割合が0.4~21質量%であり、
前記非フッ素系化合物が、炭素数1~60の炭化水素基を有する不飽和単量体、酸性官能基を有する不飽和単量体及びノニオン性官能基を有する不飽和単量体に由来する構成単位を含む共重合体であって、前記ノニオン性官能基を有する不飽和単量体が、ノニオン性官能基としての水酸基を有する不飽和単量体である場合には、前記酸性官能基を有する不飽和単量体に対する前記水酸基を有する不飽和単量体の質量比(水酸基を有する不飽和単量体/酸性官能基を有する不飽和単量体)が、2.6以下である、非フッ素系耐油剤組成物。
項2. 前記非フッ素系化合物が、前記炭素数1~60の炭化水素基を有する不飽和単量体及び前記酸性官能基を有する不飽和単量体に由来する構造を含む、項1に記載の非フッ素系耐油剤組成物。
項3. 前記非フッ素系化合物が、さらに、前記ノニオン性官能基を有する不飽和単量体に由来する構造を含む、項1又は2に記載の非フッ素系耐油剤組成物。
項4. 前記ノニオン性官能基が、水酸基、フェノール性水酸基、ニトリル基、アミド基、(チオ)ウレタン基、(チオ)ウレア基、(チオ)カーボネート基、及びエステル基からなる群より選択される少なくとも1種である、項1~3のいずれか1項に記載の非フッ素系耐油剤組成物。
項5. 紙用途で使用される、項1~4のいずれか1項に記載の非フッ素系耐油剤組成物。
項6. 食品接触用途で使用される、項1~5のいずれか1項に記載の非フッ素系耐油剤組成物。
項7. 項1~6のいずれか1項に記載の非フッ素系化合物が、基材の表面及び内部の少なくとも一方に存在する、耐油製品。
項8. 項1~6のいずれか1項に記載の非フッ素系化合物を含む耐油紙であって、
TAPPI UM-557の規定に準じて測定された前記耐油紙の平面部のキット値が、1~6である耐油紙。
項9. JIS P 8117:2009の規定に準じて測定された前記耐油紙のガーレー透気度が1000秒以下である、項8に記載の耐油紙。
本発明の非フッ素系耐油剤組成物に含まれる非フッ素系化合物は、少なくとも、炭素数1~60の炭化水素基と、中和された酸性官能基とを構成中に有する。さらに、非フッ素系化合物は、該中和された酸性官能基の占める割合(中和剤の質量は含まない)が、0.4~21質量%である。したがって、非フッ素系化合物は、低分子化合物であっても、高分子化合物であってもよい。
CH2=C(-X)-C(=O)-Y-R ・・・(1)
[式中、Xは、水素原子、1価の有機基(例えば、メチル基、エチル基など)、ハロゲン原子(フッ素原子を除く)、シアノ基または基-CH2-C(=O)-Y-Rであり、Yは、-O-及び-NH-から選択された少なくとも1つの基を有する2価~4価の連結基または-NR-であり、Rは、炭素数1~60の炭化水素基である。なお、YおよびRが、それぞれ分子中に複数存在する場合、それぞれは同一でも異なっていてもよい。]
CH2=CA1-C(=O)-O-R1-A2-R2 ・・・(2)
[式中、
A1は、水素原子、メチル基、塩素原子、臭素原子またはヨウ素原子であり、
A2は、-NH-SO2-または-SO2-NH-であり、
R1は炭素数1~5の炭化水素基であり、
R2は炭素数1~60の炭化水素基である。]
例えば、下記一般式(3)で表される化合物が好ましく使用できる。
CH2=CHC(=O)OC2H4NHSO2C18H37 ・・・(3)
(紙基材)
本発明の耐油紙に用いられる紙基材としては、特に制限されず、公知の耐油紙に用いられる紙基材を用いることができる。該紙基材としては、非塗工紙、塗工紙が挙げられる。
1≦D×(C/100)≦120 ・・・(I)
3≦D×(C/100)≦60 ・・・(II)
ただし、Dは、カチオン性高分子のカチオン電荷密度(μeq/g)であり、Cは、紙基材を構成するパルプ(100質量%)に対するカチオン性高分子の含有割合(質量%)である。
本発明の非フッ素系耐油剤組成物を紙基材に処理する方法としては、コーティングやサイズプレス、パルプスラリーに内添するなどの公知の方法が採用でき、コーティングやサイズプレスに類する方法が特に好ましい。
<TAPPI KIT法>
TAPPI UM-557の規定に従い、ひまし油、トルエン、n-ヘプタンの混合比が異なる試験液(下記表1のキット番号の混合比)の1滴を、耐油紙の表面に滴下し、15秒後に、試験液の浸透による耐油紙の表面の色の変化を目視にて評価した。試験の結果は、表面の色が濃くならない試験液のうち、数字が最も大きい試験液の番号(キット値)で表す。数字が大きい方が、耐油性に優れることを意味する。
耐油紙の耐水性は、JIS P 8122:2004の規定に準じてステキヒトサイズ度を評価した。
以下の紙基材に耐油剤組成物を処理し、実施例1~37及び比較例1~14の耐油紙を製造した。その後、各耐油紙について、前述の耐油性試験を行った。
・原紙A(薬剤の添加無し)
原料パルプとして、LBKP(広葉樹晒クラフトパルプ)およびNBKP(針葉樹晒クラフトパルプ)を用いた。LBKPとNBKPとを70:30(質量比)で混合し、叩解機によってCSFが440mLとなるように叩解し、パルプスラリーを得た後、坪量が40g/m2となるように抄紙し、坪量が40g/m2の紙基材を得た。得られた紙基材のステキヒトサイズは0秒であった。また、透気度は2秒だった。
・原紙B(湿潤紙力増強剤の添加あり)
原料パルプとして、LBKP(広葉樹晒クラフトパルプ)およびNBKP(針葉樹晒クラフトパルプ)を用いた。LBKPとNBKPとを70:30(質量比)で混合し、叩解機によってCSFが440mLとなるように叩解し、パルプスラリーを得た。当該パルプスラリーに、湿潤紙力増強剤(商品名:「FW-7281」星光PMC社製、ポリアミンエピクロルヒドリン樹脂の水溶液;固形分濃度25%)を対パルプ(固形分量)で0.4質量%添加した後、坪量が40g/m2となるように抄紙し、坪量が40g/m2の紙基材を得た。得られた紙基材のステキヒトサイズは0秒であった。また、透気度は2秒だった。
・原紙C(湿潤紙力増強剤及びサイズ剤の添加あり)
原料パルプとして、LBKP(広葉樹晒クラフトパルプ)およびNBKP(針葉樹晒クラフトパルプ)を用いた。LBKPとNBKPとを70:30(質量比)で混合し、叩解機によってCSFが440mLとなるように叩解し、パルプスラリーを得た。当該パルプスラリーに、ロジンサイズ剤を対パルプで1.0質量%添加し、硫酸バンドでパルプスラリーpHを5.0に調整し、さらに湿潤紙力増強剤(商品名:「FW-7281」星光PMC社製、ポリアミンエピクロルヒドリン樹脂の水溶液;固形分濃度25%)を対パルプ(固形分量)で0.4質量%添加した後、坪量が40g/m2となるように抄紙し、坪量が40g/m2の紙基材を得た。得られた紙基材のステキヒトサイズは10秒であった。また、透気度は2秒だった。
・サイズプレス
塗工機として、ツーロールサイズプレス機を使用し、紙基材に耐油剤組成物を付着させ、回転型乾燥機を用いて105℃で1分間乾燥させた。なお、表中に記載の「dry処理量」は、紙基材の耐油剤組成物の付着前後の質量変化量(wetピックアップ)と組成物中の非フッ素系化合物含有率を用いて算出した。
・バーコート
メイヤーバーを用いて、紙基材に耐油剤組成物を塗布し、熱風乾燥機にて110℃で5分間乾燥させた。また、必要に応じて同様の処理を繰り返し、表中記載の「dry処理量」になるように処理を行った。なお、表中に記載の「dry処理量」は、紙基材の耐油剤組成物の付着前後の質量変化量(wetピックアップ)と組成物中の非フッ素系化合物含有率を用いて算出した。
製造例1~23、比較製造例1~2について、表中記載の条件において、下記いずれかの方法にて耐油剤組成物を製造した。
反応容器に、各単量体及び重合開始剤、連鎖移動剤、界面活性剤、重合媒体を加え、窒素雰囲気下にて撹拌および昇温しラジカル重合を行った。その後、イオン交換水を用いて表中記載の重合体含有率になるように濃度調製を行い、水系耐油剤組成物を得た。
反応容器に、各単量体及び界面活性剤、重合媒体を混合し、得られた混合液を高圧ホモジナイザー(400bar)にて処理を行った。その後、重合開始剤、連鎖移動剤を添加し、窒素雰囲気下にて、撹拌および昇温しラジカル重合を行った。その後、イオン交換水を用いて表中記載の重合体含有率になるように濃度調製を行い、水系耐油剤組成物を得た。
反応容器に、各単量体及び重合開始剤、連鎖移動剤、重合媒体を加え、窒素雰囲気下にて撹拌および昇温しラジカル重合を行った。その後、内温を維持しながら、4.8%水酸化ナトリウム水溶液を表中記載の中和度になるように添加し、その後、イオン交換水を適宜添加して粘度調節し、有機溶剤を留去した。その後、イオン交換水を用いて表中記載の重合体含有率になるように濃度調製を行い、水系耐油剤組成物を得た。
反応容器に、各単量体及び重合開始剤、重合媒体、トリエタノールアミン(10.8部)を加え、窒素雰囲気下にて撹拌および昇温しラジカル重合を行った。その後、イオン交換水を適宜添加して粘度調節し、有機溶剤を留去した。その後、イオン交換水を用いて表中記載の重合体含有率になるように濃度調製を行い、水系耐油剤組成物を得た。
MMA:メチルメタクリレート
EA:エチルアクリレート
BA:ブチルアクリレート
BI-HEA:2-[(ブチルカルバモイル)オキシ]エチル=アクリラート
※ブチルイソシアネートと2-ヒドロキシエチルアクリレートの反応物
EHA:2-エチルヘキシルアクリレート
LA:ラウリルアクリレート
SA:ステアリルアクリレート
SMA:ステアリルメタクリレート
AA:アクリル酸
MAA:メタクリル酸
AAMPS:2-アクリルアミド-2-メチルプロパンスルホン酸
AN:アクリロニトリル
HEMA:2-ヒドロキシエチルメタクリレート
VP:N-ビニル-2-ピロリドン
APS:過硫酸アンモニウム
V-601:2,2’-アゾビス(イソ酪酸ジメチル)(富士フィルム和光純薬社製)
LSH:ラウリルメルカプタン
ABS:ドデシルベンゼンスルホン酸ナトリウム(ソフト型)
(ネオぺレックスG-15、花王社製、固形分濃度16%)
AES:ポリオキシアルキレンアルキルエーテル硫酸エステルアンモニウム
(エレミノールCLS-20、三洋化成工業社製、固形分濃度100%)
MEK:メチルエチルケトン
IPA:イソプロピルアルコール
TEA:トリエタノールアミン
必要に応じて中和剤を耐油剤組成物に追加し、表中記載の中和度に調製し、サイズプレスにて処理を行った。
<製造例24>
反応容器に、ステアリン酸(1.0部)及び48%水酸化ナトリウム水溶液(0.3部)、エタノール(50.0部)、イオン交換水(48.7部)を加え、固体が目視確認できなくなるまで加熱還流し、40℃まで冷却して分散液を得た。
Phoslex A-18(1.0部、SC有機化学社製、ステアリルアシッドホスフェイト:Mw437(平均値))及び4.8%水酸化ナトリウム水溶液(3.2部)、イオン交換水(75.8部)を加え、固体が目視確認できなくなるまで加熱還流した。その後、40℃まで冷却し、エタノール(20部)を加えて分散液を得た。なお、ステアリルアシッドホスフェイトはモノエステル体(Mw350.47)とジエステル体(Mw602.95)の混合物であり、ジエステル体が本発明の規定の範囲に該当する。
低分子化合物を含む耐油剤組成物として製造例24及び25を紙基材にバーコートして得られた結果を表9に示した。
本発明の耐油紙は、食品包装容器、食品包装紙、食品用敷紙等として有用である。
Claims (6)
- 炭素数1~60の炭化水素基と、中和された酸性官能基とを、少なくとも構成単位中に有する非フッ素系化合物を含み、かつ、
非フッ素系化合物は、前記中和された酸性官能基の占める割合が0.4~21質量%であり、
前記非フッ素系化合物が、下記高分子化合物1、高分子化合物2、高分子化合物3及び高分子化合物4から選択される少なくとも1種である高分子化合物を含有し、
前記高分子化合物1、前記高分子化合物2、前記高分子化合物3及び前記高分子化合物4から選択される少なくとも1種の前記高分子化合物が、ノニオン性官能基を有する不飽和単量体に由来する構成単位を含む共重合体であって、前記ノニオン性官能基を有する不飽和単量体が、ノニオン性官能基としての水酸基を有する不飽和単量体である場合には、前記酸性官能基を有する不飽和単量体に対する前記水酸基を有する不飽和単量体の質量比(水酸基を有する不飽和単量体/酸性官能基を有する不飽和単量体)が、2.6以下であり、
食品接触用途かつ紙用途で使用される、非フッ素系耐油剤組成物。
高分子化合物1:
下記一般式(1-1)で表される(メタ)アクリル酸エステル単量体、及び酸性官能基を有する不飽和単量体に由来する構成単位を含む共重合体であって、
CH2=C(-X)-C(=O)-Y-RA ・・・(1-1)
[式中、Xは、水素原子、メチル基及びエチル基から選ばれる1価の有機基、ハロゲン原子(フッ素原子を除く)、シアノ基または基-CH2-C(=O)-Y-RAであり、Yは、-O-及び-NH-から選択された少なくとも1つの基を有する2価~4価の連結基または-NRA-であり、RAは、不飽和結合を1つ以上有してもよい炭素数4~50の脂肪族炭化水素基である。なお、YおよびRAが、それぞれ分子中に複数存在する場合、それぞれは同一でも異なっていてもよい。]
前記共重合体を構成する単量体成分の全量(中和剤の質量は含まない)を基準として、前記一般式(1-1)で表される(メタ)アクリル酸エステル単量体の含有割合が、30~99.5質量%である。
高分子化合物2:
下記一般式(1-2)で表される(メタ)アクリル酸エステル単量体、及び酸性官能基を有する不飽和単量体及びノニオン性官能基を有する不飽和単量体に由来する構成単位を含む共重合体である。
CH2=C(-X)-C(=O)-Y-RB ・・・(1-2)
[式中、Xは、水素原子、メチル基及びエチル基から選ばれる1価の有機基、ハロゲン原子(フッ素原子を除く)、シアノ基または基-CH2-C(=O)-Y-RBであり、Yは、-O-及び-NH-から選択された少なくとも1つの基を有する2価~4価の連結基または-NRB-であり、RBは、炭素数1~60の炭化水素基である。なお、YおよびRBが、それぞれ分子中に複数存在する場合、それぞれは同一でも異なっていてもよい。]
高分子化合物3:
ソルビタントリステアレートメタクリレート、ソルビタントリステアレートウレタンメタクリレート、ソルビタントリステアレートウレタンスチレンモノマー及びソルビタントリオレエートメタクリレートから選択される単量体、及び酸性官能基を有する不飽和単量体に由来する構成単位を含む共重合体である。
高分子化合物4:
下記一般式(2)で表されるスルホンアミド基含有単量体、及び酸性官能基を有する不飽和単量体に由来する構成単位を含む共重合体である。
CH2=CA1-C(=O)-O-R1-A2-R2 ・・・(2)
[式中、A1は、水素原子、メチル基、塩素原子、臭素原子またはヨウ素原子であり、A2は、-NH-SO2-または-SO2-NH-であり、R1は炭素数1~5の炭化水素基であり、R2は炭素数1~60の炭化水素基である。] - 前記非フッ素系化合物が、前記ノニオン性官能基を有する不飽和単量体に由来する構造を含む、請求項1に記載の非フッ素系耐油剤組成物。
- 前記ノニオン性官能基が、水酸基、フェノール性水酸基、ニトリル基、アミド基、(チオ)ウレタン基、(チオ)ウレア基、(チオ)カーボネート基、及びエステル基からなる群より選択される少なくとも1種である、請求項2に記載の非フッ素系耐油剤組成物。
- 請求項1又は2に記載の非フッ素系化合物が、基材の表面及び内部の少なくとも一方に存在する、耐油製品。
- 請求項1又は2に記載の非フッ素系化合物を含む耐油紙であって、
TAPPI UM-557の規定に準じて測定された前記耐油紙の平面部のキット値が、1~6である耐油紙。 - JIS P 8117:2009の規定に準じて測定された前記耐油紙のガーレー透気度が1000秒以下である、請求項5に記載の耐油紙。
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