JP2008106047A - (メタ)アクリロイル基含有ロジン誘導体およびその製造方法 - Google Patents
(メタ)アクリロイル基含有ロジン誘導体およびその製造方法 Download PDFInfo
- Publication number
- JP2008106047A JP2008106047A JP2007244690A JP2007244690A JP2008106047A JP 2008106047 A JP2008106047 A JP 2008106047A JP 2007244690 A JP2007244690 A JP 2007244690A JP 2007244690 A JP2007244690 A JP 2007244690A JP 2008106047 A JP2008106047 A JP 2008106047A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- group
- rosin
- acryloyl group
- acid
- Prior art date
- 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.)
- Granted
Links
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 94
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 83
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 title claims abstract description 50
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- -1 monovinyl ether compound Chemical class 0.000 claims description 53
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 9
- UZZYXZWSOWQPIS-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC(C=O)=CC(C(F)(F)F)=C1 UZZYXZWSOWQPIS-UHFFFAOYSA-N 0.000 claims description 7
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 claims description 7
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 claims description 7
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 claims description 7
- 229940118781 dehydroabietic acid Drugs 0.000 claims description 7
- YPGLTKHJEQHKSS-ASZLNGMRSA-N (1r,4ar,4bs,7r,8as,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@H](C(C)C)C[C@@H]2CC1 YPGLTKHJEQHKSS-ASZLNGMRSA-N 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- 150000002373 hemiacetals Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000004678 hydrides Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
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- 229950000688 phenothiazine Drugs 0.000 description 5
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- MHVJRKBZMUDEEV-UHFFFAOYSA-N (-)-ent-pimara-8(14),15-dien-19-oic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)C=C1CC2 MHVJRKBZMUDEEV-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 239000000539 dimer Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MHVJRKBZMUDEEV-APQLOABGSA-N (+)-Pimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@](C=C)(C)C=C2CC1 MHVJRKBZMUDEEV-APQLOABGSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- MXYATHGRPJZBNA-UHFFFAOYSA-N 4-epi-isopimaric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)CC1=CC2 MXYATHGRPJZBNA-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- CUQHFBYOCPIUGZ-UHFFFAOYSA-N C(C)C=C(C(=O)O)OCCOC=C Chemical compound C(C)C=C(C(=O)O)OCCOC=C CUQHFBYOCPIUGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- PXYRCOIAFZBLBN-HQJFNQTASA-N fumaropimaric acid Chemical compound C([C@]12C=C([C@H](C[C@@H]11)[C@H]([C@@H]2C(O)=O)C(O)=O)C(C)C)C[C@@H]2[C@]1(C)CCC[C@@]2(C)C(O)=O PXYRCOIAFZBLBN-HQJFNQTASA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- MXYATHGRPJZBNA-KRFUXDQASA-N isopimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)CC2=CC1 MXYATHGRPJZBNA-KRFUXDQASA-N 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
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- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
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- 229920003051 synthetic elastomer Polymers 0.000 description 2
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- DRFYZAIGLPMIOS-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC=C1 DRFYZAIGLPMIOS-UHFFFAOYSA-N 0.000 description 1
- YEYCMBWKTZNPDH-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)C1=CC=CC=C1 YEYCMBWKTZNPDH-UHFFFAOYSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
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- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 1
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- 239000004135 Bone phosphate Substances 0.000 description 1
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- IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 description 1
- OBBCYCYCTJQCCK-UHFFFAOYSA-L copper;n,n-diethylcarbamodithioate Chemical compound [Cu+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S OBBCYCYCTJQCCK-UHFFFAOYSA-L 0.000 description 1
- ZOUQIAGHKFLHIA-UHFFFAOYSA-L copper;n,n-dimethylcarbamodithioate Chemical compound [Cu+2].CN(C)C([S-])=S.CN(C)C([S-])=S ZOUQIAGHKFLHIA-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
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Abstract
【解決手段】一般式(1):Ro[−COO−CH(CH3)−O−R−A]X(式(1)中、Roはロジン類に由来する環式炭化水素残基を、またRは炭素数2〜20のアルキレン基、炭素数2〜20のオキシアルキレン基および炭素数6〜11の芳香族基からなる群より選ばれる1種を、またAは(メタ)アクリロイル基を、またXは1〜3の整数を表す)で表される(メタ)アクリロイル基含有ロジン誘導体。
【選択図】
なし
Description
分水管を備えた300mlのフラスコに、荒川化学工業(株)製の水添ロジン(樹脂酸として、主にデヒドロアビエチン酸、ジヒドロアビエチン酸、テトラヒドロアビエチン酸を含む)150g、メトキノン0.23g、フェノチアジン0.23gを仕込み、攪拌下に反応系を120℃に昇温して、これらを溶融させた。次いで、アクリル酸2−(ビニロキシエトキシ)エチル82.9gを滴下ロートから15分を要して反応系に滴下し、次いでリン酸2−エチルヘキシル(商品名「AP−8」(大八化学工業(株)製))0.15gを仕込み、100℃で1時間保温し、アクリロイル基含有ロジン誘導体を得た。
分水管を備えた300mlのフラスコに、荒川化学工業(株)製のアクリル酸変性ロジンの水素化物(樹脂酸として主にアクリロピマル酸、アクリロピマル酸の水素化物、デヒドロアビエチン酸、ジヒドロアビエチン酸、テトラヒドロアビエチン酸を含む)130g、メトキノン0.23g、フェノチアジン0.23gを仕込み、攪拌下反応系しながら、140℃に昇温して溶融させた。次いで、アクリル酸(2−ビニロキシエトキシ)エチル102.4gを滴下ロートから15分を要して反応系に滴下した後、リン酸2−エチルヘキシル(商品名「AP−8」(大八化学工業(株)製))0.15gを仕込み、100℃で1時間保温し、アクリロイル基含有ロジン誘導体を得た。
分水管を備えた300mlのフラスコに、荒川化学工業(株)製の重合ロジン(樹脂酸として主に一塩基樹脂酸の二量体を含む)120g、メトキノン0.19g、フェノチアジン0.19gを仕込み、攪拌下反応系しながら、160℃に昇温して溶融させた。次いで、アクリル酸(2−ビニロキシエトキシ)エチル55.8gを滴下ロートから15分を要して反応系に滴下した後、リン酸2−エチルヘキシル(商品名「AP−8」(大八化学工業(株)製))0.12gを仕込み、100℃で1時間保温し、アクリロイル基含有ロジン誘導体を得た。
分水管を備えた300mlのフラスコに、荒川化学工業(株)製の水添ロジン(樹脂酸として、主にデヒドロアビエチン酸、ジヒドロアビエチン酸、テトラヒドロアビエチン酸を含む)150g、メトキノン0.23g、フェノチアジン0.23gを仕込み、攪拌下に反応系を120℃に昇温して、これらを溶融させた。次いで、メタクリル酸2−(ビニロキシエトキシ)エチル89.1gを滴下ロートから15分を要して反応系に滴下し、次いでリン酸2−エチルヘキシル(商品名「AP−8」(大八化学工業(株)製))0.15gを仕込み、100℃で1時間保温し、メタクリロイル基含有ロジン誘導体を得た。
Claims (9)
- 一般式(1):Ro[−COO−CH(CH3)−O−R−A]X(式(1)中、Roはロジン類に由来する環式炭化水素残基を、またRは炭素数2〜20のアルキレン基、炭素数2〜20のオキシアルキレン基および炭素数6〜11の芳香族基からなる群より選ばれる1種を、またAは(メタ)アクリロイル基を、またXは1〜3の整数を表す)で表される(メタ)アクリロイル基含有ロジン誘導体。
- 前記一般式(1)中のRoが、テトラヒドロアビエチン酸、デヒドロアビエチン酸、ジヒドロアビエチン酸、アクリロピマル酸およびアクリロピマル酸の水素化物からなる群より選ばれる1種の樹脂酸の環式炭化水素残基である、請求項1の(メタ)アクリロイル基含有ロジン誘導体。
- 前記一般式(1)が、Ro[−COO−CH(CH3)−O−(C2H4O)−A]Xである、請求項1または2の(メタ)アクリロイル基含有ロジン誘導体。
- ロジン類と、一般式(2):CH2=CH−O−R−A(式(2)中、Rは炭素数2〜20のアルキレン基、炭素数2〜20のオキシアルキレン基および炭素数6〜11の芳香族基からなる群より選ばれる1種を、またAは(メタ)アクリロイル基を表す)で表される(メタ)アクリロイル基含有モノビニルエーテル化合物とを、ヘミアセタールエステル化反応させて得られる(メタ)アクリロイル基含有ロジン誘導体。
- 前記ロジン類が、水添ロジンまたはα,β不飽和カルボン酸変性ロジンである、請求項4の(メタ)アクリロイル基含有ロジン誘導体。
- 前記一般式(2)で表される(メタ)アクリロイル基含有ビニルエーテル化合物が、(メタ)アクリル酸2−(ビニロキシエトキシ)エチルである、請求項4または5の(メタ)アクリロイル基含有ロジン誘導体。
- ロジン類と、一般式(2):CH2=CH−O−R−A(式(2)中、Rは炭素数2〜20のアルキレン基、炭素数2〜20のオキシアルキレン基、炭素数6〜11の芳香族基から選ばれる1種を、またAは(メタ)アクリロイル基を表す)で表される(メタ)アクリロイル基含有モノビニルエーテル化合物とを、ヘミアセタールエステル化反応させることを特徴とする、(メタ)アクリロイル基含有ロジン誘導体の製造方法。
- 前記ロジン類が、水添ロジンまたはα,β不飽和カルボン酸変性ロジンである、請求項7の製造方法。
- 前記一般式(2)で表される(メタ)アクリロイル基含有ビニルエーテル化合物が、(メタ)アクリル酸2−(ビニロキシエトキシ)エチルである、請求項7または8の製造方法。
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JP2010100821A (ja) * | 2008-09-29 | 2010-05-06 | Arakawa Chem Ind Co Ltd | ロジン系共重合体、活性エネルギー線硬化型樹脂組成物、および硬化物 |
WO2010087316A1 (ja) * | 2009-01-27 | 2010-08-05 | 荒川化学工業株式会社 | 鉛フリーはんだ用フラックス組成物、鉛フリーはんだ組成物およびやに入りはんだ |
JP2010235766A (ja) * | 2009-03-31 | 2010-10-21 | Arakawa Chem Ind Co Ltd | ロジン系エマルジョン |
CN103232349A (zh) * | 2013-03-28 | 2013-08-07 | 中国林业科学研究院林产化学工业研究所 | 一种松香或松香衍生物长链柔性单体的制备方法 |
WO2019230675A1 (ja) * | 2018-06-01 | 2019-12-05 | 三菱ケミカル株式会社 | 防汚塗料組成物 |
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JP2010100821A (ja) * | 2008-09-29 | 2010-05-06 | Arakawa Chem Ind Co Ltd | ロジン系共重合体、活性エネルギー線硬化型樹脂組成物、および硬化物 |
WO2010087316A1 (ja) * | 2009-01-27 | 2010-08-05 | 荒川化学工業株式会社 | 鉛フリーはんだ用フラックス組成物、鉛フリーはんだ組成物およびやに入りはんだ |
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JP5423688B2 (ja) * | 2009-01-27 | 2014-02-19 | 荒川化学工業株式会社 | 鉛フリーはんだ用フラックス組成物、鉛フリーはんだ組成物およびやに入りはんだ |
JP2010235766A (ja) * | 2009-03-31 | 2010-10-21 | Arakawa Chem Ind Co Ltd | ロジン系エマルジョン |
CN103232349A (zh) * | 2013-03-28 | 2013-08-07 | 中国林业科学研究院林产化学工业研究所 | 一种松香或松香衍生物长链柔性单体的制备方法 |
WO2019230675A1 (ja) * | 2018-06-01 | 2019-12-05 | 三菱ケミカル株式会社 | 防汚塗料組成物 |
JPWO2019230675A1 (ja) * | 2018-06-01 | 2021-06-03 | 三菱ケミカル株式会社 | 防汚塗料組成物 |
JP7413781B2 (ja) | 2018-06-01 | 2024-01-16 | 三菱ケミカル株式会社 | 防汚塗料組成物 |
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