Page 166 - 《精细化工》2023年第4期

す 40 ࢤす 4 ᱌ ㇫ ㏳ ࡃ ጒ Vol.40, No.4
20 23 Ꭱ 4 ᰵ FINE CHEMICALS Apr. 2023

㶕䲏≨ᕔݯ
ധλᲫ⇦☜⮱㶕䲏≨ᕔݯ⮱व᜽ࣷᕔ㘪

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⢸㢐㜨喑҆ ь喑ᑍͦͦ喑↗䛾㤺喑䓈ᕊ᳄喑ܮᐭⰈ
喍Ꭼ㺬ℾ᫼๔႓ ࡃ႓ࡃጒ႓䮏 ᳄ϔࡃ႓̻ጒ⼸పუℾ༁䛺◦჋侹ბ Ꭼ㺬᳄ϔࡃ႓̻ጒ⼸䛺◦჋侹ბ Ꭼ
㺬᳄ϔࡃ႓̻ጒ⼸ࡼह݈᫝͚ᓰ喑Ꭼ㺬 ࢄႮ 530006喎

ᦅ㺮喟В Į-Ძ⇦☜ͧ࣌᫆喑䕇䓴 Diels-Alder ࣺᏁݣᓄ 1-⩟ധ-4-ᐯ͆ധࣹ⣜[2.2.2]-5-䓈☜-2-⩟䚥ι⩟⅕ധΆ䚜喍ँ
㘧喑TA喎喑ںݖ⩕ϔ➖ TA ݣᓄ 1-⩟ധ-4-ᐯ͆ധࣹ⣜[2.2.2]-5-䓈☜-2-⩟䚥Ά䚜-2ƍ-(N,N-ι⩟ധ)⅔ࡃ㘧喍⅔ࡃँ
㘧喑TAO喎Ƞ1-⩟ധ-4-ᐯ͆ധࣹ⣜[2.2.2]-5-䓈☜-2-⩟䚥Ά䚜-2ƍ-(N,N-ι⩟ധ-N-㟱ധ)⅜ࡃ䨢喍㟱⅜႐䨢⯽喑TABC喎
হ 1-⩟ധ-4-ᐯ͆ധࣹ⣜[2.2.2]-5-䓈☜-2-⩟䚥Ά䚜-2ƍ-(N,N,N-̶⩟ധ)ⷅࡃ䨢喍ⷅ⩟ധ႐䨢⯽喑TAMI喎3 ⻺㶕䲏≨
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ᕔݯ喠䛴⩕ FTIR ࣷ HNMR ᄦϔ➖䔈㵹γ㐀Ჱ㶕ᒮ喑Ꭳ㔰ᄌγ 3 ⻺㶕䲏≨ᕔݯ⮱㶕䲏ᕔ㘪হើ㣹ᕔ㘪ȡ㐀᳉ࣾ
–3
–3
–3
⣝喑TAOȠTABC হ TAMI ⮱͡⩹㘣᲌⊀Ꮣ喍CMC喎ܳݘͧ 3.39×10 Ƞ2.46×10 হ 2.37×10 mol/L喑͡⩹㘣᲌
⊀Ꮣ̸⮱㶕䲏ᑍ߈喍Ȗ CMC 喎ܳݘͧ 33.0Ƞ25.2 হ 26.4 mN/m喑℁ੳ৮ࡃ㶕䲏≨ᕔݯ࡮ι☤ധι⩟ധ㟱ധ⅜ࡃ䨢⮱
CMC হ Ȗ CMC ᰡѻ喠TAOȠTABC হ TAMI ڤᰶ㞜ສ⮱Πࡃ㘪߈喑Πࡃᬣ䬡ܳݘͧ 581.0Ƞ341.7 হ 271.0 sȡTABC
হ TAMI ⮱ 0 min 䊤∎倅Ꮣज䓫 76.62 হ 82.77 mm喑Ꭳ́ι㔲⽠∎ᕔ㘪ज䓫ݝ 0.85 হ 0.87喠ₑใ喑TABC হ TAMI
ڤᰶᒵສ⮱䧆⶙Ⅱ⽠Ⴧᕔ喑㔹 TAO ⮱䧆⶙Ⅱ⽠Ⴧᕔ䒰ጛȡTABC ᄦ䛾叱㞟㦎㤱⤰㣹⮱ើ㣹≨ᕔᰭສ喑ើ㣹వⰡ
ᒱͧ 21 mm喑ើ㣹⢴ज䓫 99.99%ȡ
ڠ䩛䃺喟Į-Ძ⇦☜喠⅔ࡃ㘧喠႐䨢⯽喠㶕䲏≨ᕔݯ喠㶕䲏ᕔ㘪喠ើ㣹ᕔ
͚ఫܳㆨत喟TQ423 ᪴⡛ᴴ䃳⴮喟A ᪴」㑃त喟1003-5214 (2023) 04-0852-09

Synthesis and properties of terpinene-based surfactants

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WANG Rongzhen, YU Wei, ZHANG Dandan, WANG Jinping, XIN Silin, DIAO Kaisheng
喍School of Chemistry and Chemical Engineering, Guangxi Minzu University, Key Laboratory of Chemistry and
Engineering of Forest Products, State Ethnic Affairs Commission, Guangxi Key Laboratory of Chemistry and
Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest
Products, Nanning 530006, Guangxi, China喎

Abstract: Three surfactants of 4-isopropyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid ethyl ester-
2'-(N,N-dimethyl)amine oxide (tertiary amine N-oxide, TAO), 4-isopropyl-1-methyl-bicyclo[2.2.2]oct-5-
ene-2-carboxylic acid ethyl ester-2'-(N, N-dimethyl-N-benzyl)ammonium chloride (tertiary amine N-benzyl
chloride, TABC), and 4-isopropyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid ethyl ester-2'-(N,N,
N-trimethyl)ammonium iodide (tertiary amine N-methyl iodide, TAMI) were derived from 2-
(dimethylamino)ethyl 4-isopropyl-1-methylbicyclo[2.2.2]oct-5-ene-2-carboxylate (tertiary amine, TA) which
was synthesized from Į-terpinene by Diels-Alder reaction. The three surfactants were then characterized by
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FTIR and HNMR, followed by investigation on their surface properties and bacteriostatic abilities. The
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results showed that the critical micelle concentration (CMC) of TAO, TABC and TAMI was 3.39×10 ,
–3
–3
2.46×10 and 2.37×10 mol/L, and the corresponding surface tension (Ȗ CMC ) was 33.0, 25.2 and 26.4 mN/m,
respectively, lower than those of commercial analogue dodecyl dimethyl benzyl ammonium chloride
(DDBAC). Moreover, TAO, TABC and TAMI exhibited good emulsification property with emulsifying
time of 581.0, 341.7 and 271.0 s, respectively, as well as good foaming performance and foam stability with
a foaming height of 76.62 and 82.77 mm, and the foaming stability of 0.85 and 0.87, respectively. In
addition, TABC and TAMI perform well in calcium hard water stability test, while TAO in calcium hard

ᩣ⽬ᬒ᱌喟2022-06-28; Ⴧ⩕ᬒ᱌喟2022-11-03; DOI: 10.13550/j.jxhg.20220604
ധ䛾䶦Ⱋ喟పუ㜗♣⻾႓ധ䛾喍22166007喎
҉㔲キϸ喟⢸㢐㜨喍1996ÿ喎喑⩤喑ⶂธ⩌ȡ㖁㈨ϧ喟ܮᐭⰈ喍1967ÿ喎喑⩤喑᪆ᢵ喑E-mail喟dksphd@163.comȡ