JP5347427B2 - Asphalt adhesion inhibitor - Google Patents
Asphalt adhesion inhibitor Download PDFInfo
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- JP5347427B2 JP5347427B2 JP2008273356A JP2008273356A JP5347427B2 JP 5347427 B2 JP5347427 B2 JP 5347427B2 JP 2008273356 A JP2008273356 A JP 2008273356A JP 2008273356 A JP2008273356 A JP 2008273356A JP 5347427 B2 JP5347427 B2 JP 5347427B2
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- 239000010426 asphalt Substances 0.000 title abstract description 47
- 239000003112 inhibitor Substances 0.000 title description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 230000003405 preventing effect Effects 0.000 abstract description 19
- 239000003795 chemical substances by application Substances 0.000 abstract description 14
- 229910052751 metal Inorganic materials 0.000 abstract description 14
- 239000002184 metal Substances 0.000 abstract description 14
- 230000003449 preventive effect Effects 0.000 abstract 2
- 238000011156 evaluation Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 229940105990 diglycerin Drugs 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- -1 ethylene, propylene, 1-butene Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- NHLUYCJZUXOUBX-UHFFFAOYSA-N nonadec-1-ene Chemical compound CCCCCCCCCCCCCCCCCC=C NHLUYCJZUXOUBX-UHFFFAOYSA-N 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229940106006 1-eicosene Drugs 0.000 description 1
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 229940069096 dodecene Drugs 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
- 239000010696 ester oil Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009661 fatigue test Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- JTOGFHAZQVDOAO-UHFFFAOYSA-N henicos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCC=C JTOGFHAZQVDOAO-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl 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])[H] 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
- 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000013112 stability test Methods 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
- 239000011550 stock solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 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
Landscapes
- Road Paving Machines (AREA)
Abstract
Description
本発明は、保存安定性に優れ、金属へのアスファルトの付着防止能が高く、付着防止効果が持続するアスファルト付着防止剤に関する。 The present invention relates to an asphalt adhesion preventing agent that has excellent storage stability, has a high ability to prevent adhesion of asphalt to a metal, and maintains an adhesion preventing effect.
道路の舗装に使用するアスファルトは、アスファルトと骨材を混ぜて使用する。アスファルトは、工場からトラックの荷台に乗せて道路施工現場まで運ばれる。しかし、金属製の荷台とアスファルトが付着してしまい、舗装現場でアスファルトを下ろす時間が長くなる、アスファルトの一部が施工に使用できないという問題が発生する。 Asphalt used for road paving is a mixture of asphalt and aggregate. Asphalt is transported from the factory onto the truck bed to the road construction site. However, the metal carrier and the asphalt adhere to each other, so that it takes a long time to lower the asphalt at the pavement site, and a part of the asphalt cannot be used for the construction.
そこで従来は軽油をトラックの荷台に撒き、アスファルトの付着を防止する方法が行われていた。しかしながらこの方法では軽油がアスファルトをカットバックさせるため、アスファルトの品質が劣化するという問題点があった。これらの問題を解決するために特許文献１では、アスファルトと混和しにくいエステル油や非イオン性界面活性剤をエマルション化して使用するアスファルト付着防止剤が開示されている。しかしながらエマルションであることから経時で分離したり、冬季に低温で固まったりするため屋外で使用するアスファルト付着防止剤としては使用性に問題がある。また特許文献２では、多価アルコールからなるアスファルト付着防止剤が開示されている。しかしながら多価アルコールのみでは金属表面へのなじみが悪く、アスファルト付着防止性能を満足するものには至っていない。また、特許文献３では、多価アルコールとポリビニルアルコール、ポリアルキレングリコールを使用するアスファルト付着防止剤が開示されている。しかし、ポリビニルアルコール、ポリアルキレングリコールを組み合わせても金属表面へのなじみは良くならず、アスファルト付着防止性能を満足するものには至っていない。
本発明は、上記従来の課題を解決するものであり、その目的は、保存安定性に優れ、金属へのアスファルトの付着防止能が高く、付着防止効果が持続するアスファルト付着防止剤を提供することである。 The present invention solves the above-mentioned conventional problems, and its object is to provide an asphalt adhesion preventing agent that has excellent storage stability, has a high ability to prevent adhesion of asphalt to a metal, and maintains the adhesion preventing effect. It is.
本発明者らは、上記課題を解決するために鋭意検討を行った結果、特定の共重合体と水溶性多価アルコールと水とを配合したアスファルト付着防止剤が、保存安定性が優れ、金属へのアスファルトの付着を防止する能力が高く、付着防止効果が持続することを見出した。
すなわち、本発明は、
式（１）で表される化合物と無水マレイン酸とをモル比４：６〜８：２で重合させた重量平均分子量が２０００〜１０００００の共重合体、または、その加水分解物もしくは塩（Ａ）を０．５〜１０質量％、水溶性多価アルコール（Ｂ）を７０〜９５質量％、水（Ｃ）を４．５〜２９．５質量％含有するアスファルト付着防止剤、
As a result of intensive studies to solve the above problems, the present inventors have found that an asphalt adhesion inhibitor containing a specific copolymer, a water-soluble polyhydric alcohol, and water has excellent storage stability, metal It has been found that it has a high ability to prevent asphalt from adhering to the surface, and the anti-adhesion effect lasts.
That is, the present invention
A copolymer having a weight average molecular weight of 2000 to 100000 obtained by polymerizing a compound represented by formula (1) and maleic anhydride in a molar ratio of 4: 6 to 8: 2, or a hydrolyzate or salt thereof (A ) 0.5 to 10% by weight, water-soluble polyhydric alcohol (B) 70 to 95% by weight, water (C) 4.5 to 29.5% by weight, an asphalt adhesion inhibitor,
（式中Ｒ１、Ｒ２、Ｒ３およびＲ４は、それぞれ単独に、水素原子または炭素数１〜２２の炭化水素基を表す。）
である。
(Wherein R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms.)
It is.
本発明のアスファルト付着防止剤は、保存安定性に優れ、金属へのアスファルトの付着防止能が高く、付着防止効果が持続する。 The asphalt adhesion preventing agent of the present invention is excellent in storage stability, has a high ability to prevent asphalt adhesion to a metal, and maintains the adhesion preventing effect.
以下、本発明をさらに詳細に説明する。
本発明に用いる（Ａ）成分は、式（１）で示される化合物と無水マレイン酸とを共重合した共重合体、または、その加水分解物もしくは塩である。
Hereinafter, the present invention will be described in more detail.
The component (A) used in the present invention is a copolymer obtained by copolymerizing a compound represented by the formula (1) and maleic anhydride, or a hydrolyzate or salt thereof.
（式中Ｒ１、Ｒ２、Ｒ３およびＲ４は、それぞれ単独に、水素原子または炭素数１〜２２の炭化水素基を表す。） (Wherein R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms.)
式（１）において、Ｒ１、Ｒ２、Ｒ３およびＲ４は、水素原子または炭素数１〜２２の炭化水素基である。炭素数１〜２２の炭化水素基としては、具体的には、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、エイコシル基、ヘンイコシル基、ドコシル基、シクロヘキシル基、フェニル基等が挙げられる。Ｒ１、Ｒ２、Ｒ３およびＲ４は、それぞれ同一でも、異なっていても良い。式（１）で示される化合物として、具体的には、エチレン、プロピレン、１−ブテン、１−ペンテン、１−ヘキセン、１−ヘプテン、１−オクテン、１−ノネン、１−デセン、１−ウンデセン、１−ドデセン、１−トリデセン、１−テトラデセン、１−ペンタデセン、１−ヘキサデセン、１−ヘプタデセン、１−オクタデセン、１−ノナデセン、１−エイコセン、１−ヘンエイコセン、１−ドコセン、イソブテン、ジイソブチレン、スチレン、α−メチルスチレン等が挙げられる。 In the formula (1), R 1 , R 2 , R 3 and R 4 are a hydrogen atom or a hydrocarbon group having 1 to 22 carbon atoms. Specific examples of the hydrocarbon group having 1 to 22 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, Examples include dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, heicosyl group, docosyl group, cyclohexyl group, and phenyl group. R 1 , R 2 , R 3 and R 4 may be the same or different. Specific examples of the compound represented by the formula (1) include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene and 1-undecene. 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 1-heneicosene, 1-docosene, isobutene, diisobutylene, Examples thereof include styrene and α-methylstyrene.
本発明に用いる（Ａ）成分は、式（１）で示される化合物と無水マレイン酸とを公知の方法、例えば、有機溶媒中で、重合開始剤を用いて共重合することにより得られる。共重合する際の、式（１）で示される化合物と無水マレイン酸のモル比は、４：６〜８：２であり、好ましくは５：５〜８：２である。モル比が８：２より大きくなると（Ａ）成分の水溶性が低くなり、またモル比が４：６より小さくなると付着防止効果が悪くなる。 The component (A) used in the present invention is obtained by copolymerizing the compound represented by the formula (1) and maleic anhydride in a known method, for example, in an organic solvent using a polymerization initiator. The molar ratio of the compound represented by formula (1) to maleic anhydride when copolymerizing is 4: 6 to 8: 2, preferably 5: 5 to 8: 2. When the molar ratio is larger than 8: 2, the water solubility of the component (A) is lowered, and when the molar ratio is smaller than 4: 6, the adhesion preventing effect is deteriorated.
（Ａ）成分の重量平均分子量は、２０００〜１０００００であり、好ましくは４０００〜７００００である。重量平均分子量が２０００より低い場合は十分な持続する付着防止効果を得ることができず、重量平均分子量が１０００００を超える場合には保存安定性が悪くなる。 (A) The weight average molecular weight of a component is 2000-100000, Preferably it is 4000-70000. When the weight average molecular weight is lower than 2000, a sufficiently long adhesion preventing effect cannot be obtained, and when the weight average molecular weight exceeds 100,000, the storage stability is deteriorated.
式（１）で示される化合物と無水マレイン酸の共重合体は、加水分解を行い加水分解物としても、加水分解物を塩基性化合物で中和した塩として使用することもできる。中和に使用する塩基性化合物としては、アルカリ金属の水酸化物、アルカリ土類金属の水酸化物、アンモニアまたは有機アミンが挙げられる。アルカリ金属の水酸化物としては水酸化リチウム、水酸化ナトリウム、水酸化カリウム等が挙げられ、好ましくは、水酸化ナトリウム、水酸化カリウムである。アルカリ土類金属の水酸化物としては、水酸化マグネシウム、水酸化カルシウムが挙げられる。有機アミンとしては、例えばモノエタノールアミン、ジエタノールアミン、トリエタノールアミンなどのアルカノールアミン、メチルアミン、ジメチルアミン、トリメチルアミン、エチルアミン、ジエチルアミン、トリエチルアミンなどのアルキルアミンが挙げられ、好ましくはモノエタノールアミン、ジエタノールアミン、メチルアミン、エチルアミン、ジエチルアミンである。 The copolymer of the compound represented by the formula (1) and maleic anhydride can be used as a hydrolyzate by hydrolysis and a salt obtained by neutralizing the hydrolyzate with a basic compound. Examples of the basic compound used for neutralization include alkali metal hydroxides, alkaline earth metal hydroxides, ammonia, and organic amines. Examples of the alkali metal hydroxide include lithium hydroxide, sodium hydroxide and potassium hydroxide, and sodium hydroxide and potassium hydroxide are preferable. Examples of the alkaline earth metal hydroxide include magnesium hydroxide and calcium hydroxide. Examples of the organic amine include alkanolamines such as monoethanolamine, diethanolamine and triethanolamine, and alkylamines such as methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine and triethylamine, preferably monoethanolamine, diethanolamine and methyl. Amine, ethylamine and diethylamine.
アスファルト付着防止剤中の、（Ａ）成分は０．５〜１０重量％の範囲であり、好ましくは１．０〜８重量％の範囲である。（Ａ）成分が０．５重量％未満では持続する付着防止効果を得ることができず、１０重量％を越えても添加量にみあった効果が得られず経済的でない。 The component (A) in the asphalt adhesion preventing agent is in the range of 0.5 to 10% by weight, preferably in the range of 1.0 to 8% by weight. If the component (A) is less than 0.5% by weight, a continuous adhesion preventing effect cannot be obtained, and if it exceeds 10% by weight, the effect corresponding to the amount added cannot be obtained and it is not economical.
本発明に用いる（Ｂ）成分は水溶性多価アルコールである。具体的には、エチレングリコール、ジエチレングリコール、プロピレングリコール、ブチレングリコール、グリセリン、ジグリセリン、ポリグリセリン、ペンタエリスリトールなどが挙げられ、好ましくはエチレングリコール、ジエチレングリコール、プロピレングリコール、ブチレングリコール、グリセリン、ジグリセリンが挙げられる。これらは単独で、あるいは複数を組み合わせて使用することができる。
アスファルト付着防止剤中の（Ｂ）成分は７０〜９５重量％の範囲であり、好ましくは７５〜９０重量％の範囲である。（Ｂ）成分が７０重量％未満では保存安定性が悪く、９５重量％を越えると持続する付着防止効果が悪くなる。
The component (B) used in the present invention is a water-soluble polyhydric alcohol. Specific examples include ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, glycerin, diglycerin, polyglycerin, pentaerythritol, and the like, preferably ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, glycerin, and diglycerin. It is done. These can be used alone or in combination.
The component (B) in the asphalt adhesion preventing agent is in the range of 70 to 95% by weight, preferably in the range of 75 to 90% by weight. When the component (B) is less than 70% by weight, the storage stability is poor, and when it exceeds 95% by weight, the sustained adhesion preventing effect is deteriorated.
（Ｃ）成分である水は、具体的には、イオン交換水、水道水等が挙げられる。（Ｃ）成分は、４．５〜２９．５重量％の範囲であり、好ましくは７〜２５重量％の範囲である。（Ｃ）成分が４．５重量％未満では保存安定性が悪く、２９．５重量％を越えると輸送時のコストが上がり好ましくない。 Specific examples of the water (C) include ion exchange water and tap water. Component (C) is in the range of 4.5 to 29.5% by weight, preferably 7 to 25% by weight. If the component (C) is less than 4.5% by weight, the storage stability is poor, and if it exceeds 29.5% by weight, the cost during transportation increases.
本発明のアスファルト付着防止剤は原液でも、水で３〜３０倍に希釈して使用することもできる。 The asphalt adhesion inhibitor of the present invention can be used as a stock solution or diluted 3 to 30 times with water.
本発明のアスファルト付着防止剤には、本発明の性能を損なわない程度に、界面活性剤、色素、酸化防止剤、防錆剤、防腐剤を添加してもよい。 To the asphalt adhesion preventing agent of the present invention, a surfactant, a pigment, an antioxidant, a rust inhibitor, and an antiseptic may be added to the extent that the performance of the present invention is not impaired.
以下、実施例を挙げて本発明を更に具体的に説明する。 Hereinafter, the present invention will be described more specifically with reference to examples.
実施例および比較例に供した共重合体については、表１に示す式（１）の化合物と無水マレイン酸との共重合体を用いた。重量平均分子量については、ゲルパーミエーションクロマトグラフィーにより求めた。 About the copolymer used for the Example and the comparative example, the copolymer of the compound of Formula (1) shown in Table 1 and maleic anhydride was used. The weight average molecular weight was determined by gel permeation chromatography.
表２、表３に示す割合で、アスファルト付着防止剤を調製し、以下の試験に供した。尚、表中の％は、質量％を表す。結果を表２、表３に示す。
Asphalt adhesion inhibitors were prepared at the ratios shown in Tables 2 and 3 and subjected to the following tests. In addition,% in a table | surface represents the mass%. The results are shown in Tables 2 and 3.
＜アスファルト付着防止剤試験＞
（１）希釈液の金属表面へのなじみテスト
各付着防止剤を水で１０倍に希釈した液を、エタノールで洗浄した１０ｃｍ×１０ｃｍのＳＳ４００鋼材に１ｇ塗布し、金属表面へのなじみ具合を目視にて確認した。評価基準は、下記の評価基準に従い判定した。
評価基準
○：金属表面に均一に広がる。
△：金属表面に塗布したときにムラが生じる。
×：金属表面上で水滴状になり、なじまない。
<Asphalt adhesion inhibitor test>
(1) Fatigue test of diluted solution on metal surface 1 g of a solution obtained by diluting each anti-adhesion agent 10 times with water was applied to a 10 cm x 10 cm SS400 steel material washed with ethanol, and the conformity to the metal surface was visually observed. Confirmed. Evaluation criteria were determined according to the following evaluation criteria.
Evaluation criteria ○: Spread uniformly on the metal surface.
Δ: Unevenness occurs when applied to a metal surface.
X: Water droplets are formed on the metal surface and do not fit.
（２）希釈液の金属表面への残留テスト
各付着防止剤を水で１０倍に希釈した液を、エタノールで洗浄した１０ｃｍ×１０ｃｍのＳＳ４００鋼材に１ｇ塗布後、鉄板を４５度の角度に傾斜させ、１０分後の希釈液の残留量を測定した。残存率（％）を以下の計算式で求め、残存率から以下のように判定した。
残存率（％）＝｛（塗布量−１０分後の残存量）／塗布量｝×１００で計算した。
判定基準
○：残存率が９５％以上。
△：残存率が９５％未満〜６０％以上。
×：残存率が６０％未満。
(2) Residual test on the metal surface of the diluted solution After applying 1 g of a solution obtained by diluting each anti-adhesion agent 10 times with water to 10 cm x 10 cm SS400 steel washed with ethanol, the steel plate is inclined at an angle of 45 degrees. The residual amount of the diluted solution after 10 minutes was measured. The residual rate (%) was determined by the following calculation formula, and judged from the residual rate as follows.
Residual rate (%) = {(application amount−remaining amount after 10 minutes) / application amount} × 100.
Judgment criteria ○: The residual rate is 95% or more.
Δ: Residual rate is less than 95% to 60% or more.
X: Residual rate is less than 60%.
（３）付着防止テスト
各付着防止剤を水で１０倍に希釈した液を、エタノールで洗浄した１０ｃｍ×１０ｃｍのＳＳ４００鋼材に１ｇ塗布した鉄板に２００℃に加熱したアスファルトを乗せ、３．０ｋｇ加重した状態で３０分間常温で放置しアスファルトの付着性を目視にて確認した。評価基準は、下記の評価基準に従い判定した。
(3) Adhesion prevention test A solution obtained by diluting each anti-adhesion agent 10 times with water on an iron plate coated with 1 g of 10 cm x 10 cm SS400 steel washed with ethanol was placed on an asphalt heated to 200 ° C and loaded with 3.0 kg In this state, it was left at room temperature for 30 minutes, and the adhesion of asphalt was visually confirmed. Evaluation criteria were determined according to the following evaluation criteria.
評価基準
◎：アスファルトの付着がほとんどない。
○：アスファルトの付着がわずかにある。
△：アスファルトの付着がある。
×：アスファルト及び骨材の付着がある。
Evaluation criteria A: There is almost no asphalt adhesion.
○: Slightly attached asphalt.
Δ: Asphalt adheres.
X: There is adhesion of asphalt and aggregate.
（４）付着防止効果持続テスト
各付着防止剤を水で１０倍に希釈した液を、エタノールで洗浄した１０ｃｍ×１０ｃｍのＳＳ４００鋼材に１ｇ塗布した鉄板に２００℃に加熱したアスファルトを乗せ、３．０ｋｇ加重した状態で、３０分間常温で放置しアスファルトの付着性を目視にて確認した。この試験を合計４回繰り返し、そのときのアスファルトの付着性を目視にて確認した。評価基準は、下記の評価基準に従い判定した。
評価基準
○：４回繰り返してもアスファルトの付着がわずかにある程度である。
△：３〜４回目でアスファルトの付着がある。
×：２回目でアスファルト及び骨材の付着がある。
(4) Adhesion prevention effect continuity test A solution obtained by diluting each adhesion inhibitor 10 times with water was placed on an iron plate coated with 1 g of a 10 cm × 10 cm SS400 steel material washed with ethanol, and asphalt heated to 200 ° C. was placed thereon. With 0 kg applied, it was allowed to stand at room temperature for 30 minutes, and asphalt adhesion was visually confirmed. This test was repeated a total of 4 times, and asphalt adhesion at that time was visually confirmed. Evaluation criteria were determined according to the following evaluation criteria.
Evaluation criteria ○: Asphalt adherence is slight to some extent even after repeating 4 times.
(Triangle | delta): Asphalt adheres in the 3rd-4th time.
X: Asphalt and aggregate adhere in the second time.
（５）保存安定性テスト
各付着防止剤を水で１０倍に希釈し、４０℃、２５℃、−５℃で１週間保存し、外観を確認した。評価基準は、下記の評価基準に従い判定した。
評価基準
○：変化なし
△：一部分離または固化している。
×：分離または固化している。
(5) Storage stability test Each adhesion inhibitor was diluted 10 times with water and stored at 40 ° C, 25 ° C and -5 ° C for 1 week, and the appearance was confirmed. Evaluation criteria were determined according to the following evaluation criteria.
Evaluation criteria ○: No change △: Partially separated or solidified.
X: Separated or solidified.
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |