JP2018165327A - アミンオキシド基含有樹脂の製造方法 - Google Patents
アミンオキシド基含有樹脂の製造方法 Download PDFInfo
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- JP2018165327A JP2018165327A JP2017063523A JP2017063523A JP2018165327A JP 2018165327 A JP2018165327 A JP 2018165327A JP 2017063523 A JP2017063523 A JP 2017063523A JP 2017063523 A JP2017063523 A JP 2017063523A JP 2018165327 A JP2018165327 A JP 2018165327A
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- Prior art keywords
- containing resin
- solution
- amine oxide
- peroxide
- group
- Prior art date
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- 239000011347 resin Substances 0.000 title claims abstract description 113
- 229920005989 resin Polymers 0.000 title claims abstract description 113
- 150000001412 amines Chemical class 0.000 title claims abstract description 45
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 125000003277 amino group Chemical group 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- 150000002978 peroxides Chemical class 0.000 claims abstract description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 26
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 84
- 239000000178 monomer Substances 0.000 description 43
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 238000007254 oxidation reaction Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 18
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- 230000000052 comparative effect Effects 0.000 description 7
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- 230000035484 reaction time Effects 0.000 description 3
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
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- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- IEQWWMKDFZUMMU-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)CCOC(=O)C=C IEQWWMKDFZUMMU-UHFFFAOYSA-N 0.000 description 1
- YDRQKFSCVSLQKI-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethyl)cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1(CCOC(=O)C=C)C(O)=O YDRQKFSCVSLQKI-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
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- 125000001117 oleyl 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])/C([H])=C([H])\C([H])([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
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl 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])C([H])([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
- 125000002958 pentadecyl 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])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
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 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
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 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
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 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
Landscapes
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
(1−1)比較例1〜6
反応容器として、還流冷却器、温度計、窒素吹込管、滴下漏斗、及び攪拌機が取り付けられた容量1リットルの4つ口フラスコを用い、この反応容器中にエタノール100部、及び表1に示す配合組成で予め調製しておいたエチレン性不飽和単量体成分100部を仕込み、窒素気流下で昇温した。この反応容器中のエタノールが還流状態(約80℃)になったところで、このエタノール中に重合開始剤として2,2’−アゾビスイソブチロニトリルを0.5部添加し、4時間重合を行い、アミノ基含有樹脂を含む溶液を得た。
反応容器として、蒸気吹込管、還流冷却器、温度計、窒素吹込管、滴下漏斗、及び攪拌機が取り付けられた容量1リットルの4つ口フラスコを用い、この反応容器中にエタノール100部、及び表1に示す配合組成で予め調製しておいたエチレン性不飽和単量体成分100部を仕込み、窒素気流下で昇温した。この反応容器中のエタノールが還流状態(約80℃)になったところで、このエタノール中に重合開始剤として2,2’−アゾビスイソブチロニトリルを0.5部添加し、4時間重合を行い、アミノ基含有樹脂を含む溶液を得た。
・DMMA:ジメチルアミノエチルメタクリレート
・DEMA:ジエチルアミノエチルメタクリレート
・DMAPAA:ジメチルアミノプロピルアクリルアミド
[エチレン性不飽和単量体(B)]
・MMA:メチルメタクリレート
・EA:エチルアクリレート
・BA:n−ブチルアクリレート
・BMA:n−ブチルメタクリレート
・M−90G:メトキシポリエチレングリコール(n=9)メタクリレート(新中村化学工業株式会社製)
・M−230G:メトキシポリエチレングリコール(n=23)メタクリレート(新中村化学工業株式会社製)
・HEMA:ヒドロキシエチルメタクリレート
・HEAA:ヒドロキシエチルアクリルアミド
・DMAA:N,N−ジメチルアクリルアミド
・AE−400:ポリエチレングリコール(n≒10)モノアクリレート(日油株式会社製))
・AP−400:ポリプロピレングリコール(n=6)アクリレート(日油株式会社製)
(2)安定性評価
樹脂溶液を容器に投入してから、容器を密閉し、室温(約25℃)で1か月の間静置した。その後、別の容器に、静置後の樹脂溶液の一部を加え、固形分濃度が2.5%となるように、水を加えて希釈することで水溶液を調製し、その水溶液のpHを測定した。その結果を表2に示す。
樹脂溶液5gに、希硫酸5g、エタノール20g、及び10%ヨウ化カリウム水溶液15gを加えて溶液を調製し、この溶液を室温で均一に攪拌して30分間静置した。続いて、溶液に1%のデンプン水溶液を数滴加えた後、0.1mol/Lのチオ硫酸ナトリウム水溶液を滴下し過酸化水素の定量を行った。滴下の終点は、溶液が黄色から無色に変化した点とした。その結果を表2に示す。
(4−1)ジェル組成物の調製
[実施例1〜6]
商品名カーボポール940(The Lubrizol Corporation製)0.3質量部と水29.7質量部を容器に投入し、カーボポールを溶解させた後、トリエタノールアミン1.0質量部、及び(1−2)で調整した樹脂溶液16質量部を配合し、攪拌した。続いて、エタノール5質量部を配合した後、合計が100質量部となるように水を加え、混合することで頭髪用ジェル組成物を作製した。
樹脂溶液の種類を(1−1)で調整した樹脂溶液に、及びエタノールの配合量を1質量部に、変更した以外は、上述の[実施例1〜6]の場合と同様にして、頭髪用ジェル組成物を作製した。
(4−1)で調整した各頭髪用ジェル組成物を、10人の被験者が頭髪に塗布することで、塗布前後の硬さを次の基準で評価した。
(4−1)で調整した各頭髪用ジェル組成物を、10人の被験者が頭髪に塗布することで、塗布前後の弾力を次の基準で評価した。
Claims (6)
- アミノ基含有樹脂と過酸化物とを含む溶液中で、前記アミノ基含有樹脂と前記過酸化物とを反応させアミンオキシド基含有樹脂を生成する工程を含み、
前記工程において、前記溶液中に水蒸気を通気する、
アミンオキシド基含有樹脂の製造方法。 - 前記過酸化物は、過酸化水素を含む、
請求項1に記載のアミンオキシド基含有樹脂の製造方法。 - 前記溶液中の前記過酸化物の含有量が、前記アミンオキシド基含有樹脂に対し、1,000ppm以下となるまで反応させる、
請求項1又は2に記載のアミンオキシド基含有樹脂の製造方法。 - 前記溶液は、水、メタノール、エタノール、及び2−プロパノールからなる群から選択される少なくとも一種の溶媒を含む、
請求項1〜3のいずれか一項に記載のアミンオキシド基含有樹脂の製造方法。 - 前記アミノ基含有樹脂は、第3級アミノ基を有する、
請求項1〜4のいずれか一項に記載のアミンオキシド基含有樹脂の製造方法。
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Citations (3)
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JPH08507318A (ja) * | 1993-03-03 | 1996-08-06 | ビーエーエスエフ アクチエンゲゼルシャフト | ポリビニルピリジンn−オキシドの製造 |
JP2000336018A (ja) * | 1999-03-19 | 2000-12-05 | Mitsubishi Chemicals Corp | 毛髪化粧料 |
JP2007319234A (ja) * | 2006-05-30 | 2007-12-13 | Ozonikku:Kk | 蒸気噴霧装置 |
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JPH08507318A (ja) * | 1993-03-03 | 1996-08-06 | ビーエーエスエフ アクチエンゲゼルシャフト | ポリビニルピリジンn−オキシドの製造 |
JP2000336018A (ja) * | 1999-03-19 | 2000-12-05 | Mitsubishi Chemicals Corp | 毛髪化粧料 |
JP2007319234A (ja) * | 2006-05-30 | 2007-12-13 | Ozonikku:Kk | 蒸気噴霧装置 |
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