JPH053871B2 - - Google Patents

Info

Publication number: JPH053871B2
Authority: JP; Japan
Prior art keywords: mmol; alcohol; vinyl; aryl; hydrolysis
Prior art date: 1985-02-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP3746785A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61197552A (ja

Inventor

Hiromi Kamogawa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

NOF Corp

Original Assignee

Nippon Oil and Fats Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-02-28

Filing date

1985-02-28

Publication date

1993-01-18

1985-02-28 Application filed by Nippon Oil and Fats Co Ltd filed Critical Nippon Oil and Fats Co Ltd

1985-02-28 Priority to JP3746785A priority Critical patent/JPS61197552A/ja

1986-09-01 Publication of JPS61197552A publication Critical patent/JPS61197552A/ja

1993-01-18 Publication of JPH053871B2 publication Critical patent/JPH053871B2/ja

Status Granted legal-status Critical Current

Links

MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 claims description 14
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 14
QMVPMAAFGQKVCJ-UHFFFAOYSA-N Citronellol Natural products OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 10
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical group CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 10
OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical group OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims description 8
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical group COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 8
QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 6
PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical group CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 claims description 6
JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 6
235000000484 citronellol Nutrition 0.000 claims description 6
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 4
NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical group CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims description 4
REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Chemical group C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 claims description 4
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical group OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 4
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical group COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims description 4
NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Chemical group COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 4
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Chemical group CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 4
239000005770 Eugenol Chemical group 0.000 claims description 4
239000005792 Geraniol Chemical group 0.000 claims description 4
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Chemical group CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 4
BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Chemical group COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims description 4
UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Chemical group COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 4
OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Chemical group OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 claims description 4
CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Chemical group C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 claims description 4
229940116229 borneol Drugs 0.000 claims description 4
BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical group COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 claims description 4
DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Chemical group C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 claims description 4
229960002217 eugenol Drugs 0.000 claims description 4
229940113087 geraniol Drugs 0.000 claims description 4
BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Chemical group COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 claims description 4
125000000300 citronellol group Chemical group 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
125000003118 aryl group Chemical group 0.000 description 16
239000007788 liquid Substances 0.000 description 16
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
125000000217 alkyl group Chemical group 0.000 description 14
230000007062 hydrolysis Effects 0.000 description 14
238000006460 hydrolysis reaction Methods 0.000 description 14
229920002554 vinyl polymer Polymers 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
238000005160 1H NMR spectroscopy Methods 0.000 description 11
229920001577 copolymer Polymers 0.000 description 11
VHEKFTULOYIMSU-UHFFFAOYSA-N 4-ethenylbenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C=C)C=C1 VHEKFTULOYIMSU-UHFFFAOYSA-N 0.000 description 10
238000000921 elemental analysis Methods 0.000 description 10
-1 aromatic alcohols Chemical class 0.000 description 9
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
238000004949 mass spectrometry Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 7
239000000178 monomer Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000011259 mixed solution Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
150000003459 sulfonic acid esters Chemical class 0.000 description 4
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003205 fragrance Substances 0.000 description 3
230000002209 hydrophobic effect Effects 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000000243 solution Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000005923 long-lasting effect Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229950000688 phenothiazine Drugs 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-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
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
KLJQGIMMJZEAAX-UHFFFAOYSA-N 2-phenylethyl 4-ethenylbenzenesulfonate Chemical compound C1=CC(C=C)=CC=C1S(=O)(=O)OCCC1=CC=CC=C1 KLJQGIMMJZEAAX-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
FGIGPKRIJUAUOI-UHFFFAOYSA-N C1=CC(OC)=CC=C1COS(=O)(=O)C1=CC=C(C=C)C=C1 Chemical compound C1=CC(OC)=CC=C1COS(=O)(=O)C1=CC=C(C=C)C=C1 FGIGPKRIJUAUOI-UHFFFAOYSA-N 0.000 description 1
NXJYKHQUKAGJHZ-UHFFFAOYSA-N C=CC1=CC=C(C=C1)S(=O)(=O)OCC=CC1=CC=CC=C1 Chemical compound C=CC1=CC=C(C=C1)S(=O)(=O)OCC=CC1=CC=CC=C1 NXJYKHQUKAGJHZ-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
125000003438 dodecyl group Chemical group [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])* 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229920001480 hydrophilic copolymer Polymers 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000012690 ionic polymerization Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 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
239000002304 perfume Substances 0.000 description 1
230000002688 persistence Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP3746785A 1985-02-28 1985-02-28 芳香アルコ−ル　ｐ−スチレンスルホン酸エステル Granted JPS61197552A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP3746785A JPS61197552A (ja)	1985-02-28	1985-02-28	芳香アルコ−ル　ｐ−スチレンスルホン酸エステル

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3746785A JPS61197552A (ja)	1985-02-28	1985-02-28	芳香アルコ−ル　ｐ−スチレンスルホン酸エステル

Publications (2)

Publication Number	Publication Date
JPS61197552A JPS61197552A (ja)	1986-09-01
JPH053871B2 true JPH053871B2 (fr)	1993-01-18

Family

ID=12498327

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3746785A Granted JPS61197552A (ja)	1985-02-28	1985-02-28	芳香アルコ−ル　ｐ−スチレンスルホン酸エステル

Country Status (1)

Country	Link
JP (1)	JPS61197552A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5670466A (en) *	1995-12-20	1997-09-23	The Procter & Gamble Company	Sulfonate perfumes for laundry and cleaning compositions
JP4791634B2 (ja)	1999-03-26	2011-10-12	フイルメニツヒソシエテアノニム	環式化合物およびその芳香性アルコール前駆体としての使用
US6939835B2 (en)	1999-03-26	2005-09-06	Firmenich Sa	Cyclic compounds and their use as precursors of fragrant alcohols
JP5159087B2 (ja) *	2005-11-11	2013-03-06	キヤノン株式会社	荷電制御剤、及び静電荷像現像トナー

1985
- 1985-02-28 JP JP3746785A patent/JPS61197552A/ja active Granted

Also Published As

Publication number	Publication date
JPS61197552A (ja)	1986-09-01

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