CN1167731C - 用作沥青的乳化剂的液态胺组合物 - Google Patents
用作沥青的乳化剂的液态胺组合物 Download PDFInfo
- Publication number
- CN1167731C CN1167731C CNB98118863XA CN98118863A CN1167731C CN 1167731 C CN1167731 C CN 1167731C CN B98118863X A CNB98118863X A CN B98118863XA CN 98118863 A CN98118863 A CN 98118863A CN 1167731 C CN1167731 C CN 1167731C
- Authority
- CN
- China
- Prior art keywords
- amine
- acid
- aminopropyl
- dipropylenetriamine
- tallow
- 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.)
- Expired - Lifetime
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 239000007788 liquid Substances 0.000 title claims abstract description 31
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 11
- 239000010426 asphalt Substances 0.000 title abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 33
- 229920000768 polyamine Polymers 0.000 claims abstract description 31
- 150000007524 organic acids Chemical class 0.000 claims abstract description 19
- -1 propylidene tetramine Chemical compound 0.000 claims description 42
- 239000003760 tallow Substances 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 5
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 claims description 4
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical group CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 4
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 claims description 4
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 4
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 claims description 2
- UKNVXIMLHBKVAE-UHFFFAOYSA-N n'-hexadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCNCCCN UKNVXIMLHBKVAE-UHFFFAOYSA-N 0.000 claims description 2
- DXYUWQFEDOQSQY-UHFFFAOYSA-N n'-octadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCCN DXYUWQFEDOQSQY-UHFFFAOYSA-N 0.000 claims description 2
- SSSZZOVUXFLWCQ-UHFFFAOYSA-N n'-tetradecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCNCCCN SSSZZOVUXFLWCQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 230000001804 emulsifying effect Effects 0.000 abstract description 17
- 239000000839 emulsion Substances 0.000 abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 239000011295 pitch Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 15
- 150000004985 diamines Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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- 230000000694 effects Effects 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000007711 solidification Methods 0.000 description 5
- 230000008023 solidification Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IGIDLTISMCAULB-UHFFFAOYSA-N 3-methylvaleric acid Chemical compound CCC(C)CC(O)=O IGIDLTISMCAULB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical group CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 2
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
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- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供了一种用作沥青的乳化剂的液态胺组合物,它能够使得沥青具有优于常规产品的乳化稳定性和与聚集料的粘附性。本发明用作沥青的乳化剂的液态胺组合物包含(1)按重量计,5%至70%具有8至22个碳原子的脂族烃基的单胺,(2)按重量计,20%至80%具有8至22个碳原子的脂族烃基的聚胺,(3)按重量计,10%至75%具有4至18个碳原子的有机酸。
Description
本发明涉及用作沥青的乳化剂的胺组合物,它易于处理并在常温下呈液态。更具体地说,本发明涉及一种液态胺组合物,它是乳化沥青之类沥青类材料的乳化剂的前体,具有优良的加工性能,并可使得最终被乳化的沥青类材料具有优于常规产品的乳化稳定性以及与聚集料的粘附性。
具有至少8个碳原子的烃基的胺化合物具有广泛的工业用途,因为由胺化合物衍生得到的阳离子表面活性剂具有优良的性能。例如,这类胺化合物被用作沥青类材料的水相乳化剂,沥青类材料即用在路面材料、岸堤的防水材料和屋顶材料等用途中的被称为石油沥青、沥青等的各种固体样油状物。而且,还已知,这类胺化合物还被用作矿物质的浮选分离剂(floating seperation agent),聚合物和纤维等的抗静电剂,金属的防蚀剂和化肥的抗凝剂。
为了在所述的用途中发挥胺化合物的优良性能,需要具有与对象的高吸附性,所以优选具有长链烃基的胺化合物。但是,大多数此类胺化合物在室温下是固态的,因而加工困难。所以,为了将所述的胺化合物液化,迄今已进行了多方面的研究。所述的加工问题在冬天和低温地区尤其突出。
例如,在US-A4496474和US-A5098604中,为了降低熔点,提出了使用结晶性能较差的烷基醚胺,支链烷基胺或烷氧基化的胺。但是,此时的缺点之一在于阳离子表面活性降低,而且即使增加胺的量也无法获得固体胺所具有的优良特性。
此外,在JP-A59-123523中公开了一种含有脂族胺和特殊的羧酸的液态胺组合物。该液态胺组合物即使在低温下仍是液态的,而且当所述的液态胺组合物被用作阳离子表面活性剂时,可加入盐酸之类的强酸以形成盐酸胺,以致可能获得与原来固态胺几乎相同的性能。
在现有技术中尚不清楚的是胺组合物、沥青类材料的乳化稳定性和沥青类材料的粘附性之间的关系。随着近年来汽车重量的增加和速度的提高,人们迫切需与聚集料具有更高的粘附性。这就是为什么针入度很小的硬沥青被广泛地使用的缘故。但是,所述的常规产品并不总能满足性能要求。
在这种情况下,本发明旨在进一步提高乳化稳定性和加工性能,所以,本发明的目的是提供一种胺组合物,它在常温下是液态并能够形成具有更高性能的乳液。本发明者为阐明最佳胺组合物,将乳液降解之后深入研究了胺组合物和乳化稳定性之间的关系以及胺组合物与沥青类材料粘附性之间的关系。结果发现了使沥青类材料具有前所未有的高乳化稳定性和粘附性的、用作沥青类材料乳化剂的液态胺组合物。而且,在这些新的胺组合物中还发现了一种具有低粘度因而具有更好的加工性能的组合物。
换言之,本发明的目的是提供用作沥青类材料的乳化剂的液体胺组合物,它包含(1)按重量计5%至70%具有8至22个碳原子的脂族烃基的单胺,(2)按重量计20%至80%具有8至22个碳原子的脂族烃基的聚胺,和(3)按重量计10%至75%的具有4至18个碳原子的有机酸。
可用于本发明的具有8至22个碳原子的脂族烃基的单胺(1)是以结构式R1R2R3N表示的脂族胺化合物,其中的R1是具有8至22个碳原子的直链烃基,R2和R3各自为氢原子或具有8至22个碳原子的直链烃基。单胺的典型例子包括例如癸胺、十二烷基胺、十四烷基胺、十六烷基胺、十八烷基胺、二十二烷基胺、牛脂胺(tallowamine)和氢化牛脂胺。
可用于本发明的具有8至22个碳原子的脂族烃基的聚胺(2)是以结构式R1R2N(ANH)PH表示的脂族胺化合物,其中的R1、R2和R3如前所述,A是亚乙基基团或亚丙基基团,P是1至4。
聚胺的典型例子包括上述单胺(1)与丙烯腈反应,然后将反应产物加氢而得的二胺,这类二胺的例子包括N-氨基丙基烷基胺,例如N-氨基丙基癸基胺、N-氨基丙基十二烷基胺、N-氨基丙基十四烷基胺、N-氨基丙基十六烷基胺、N-氨基丙基十八烷基胺、N-氨基丙基二十二烷基胺、N-氨基丙基牛脂胺和N-氨基丙基氢化牛脂胺。
此外,聚胺的其它例子包括重复上述过程得到的三胺和四胺。三胺的例子包括N-烷基二亚丙基三胺,例如N-癸基二亚丙基三胺、N-十二烷基二亚丙基三胺、N-十四烷基二亚丙基三胺、N-十六烷基二亚丙基三胺、N-十八烷基二亚丙基三胺、N-二十二烷基二亚丙基三胺、N-牛脂基二亚丙基三胺和氢化N-牛脂基二亚丙基三胺;四胺的实例包括N-烷基三亚丙基四胺,例如N-癸基三亚丙基四胺、N-十二烷基三亚丙基四胺、N-十四烷基三亚丙基四胺、N-十六烷基三亚丙基四胺、N-十八烷基三亚丙基四胺、N-二十二烷基三亚丙基四胺、N-牛脂基三亚丙基四胺和氢化N-牛脂基三亚丙基四胺。此外,四胺的例子包括卤代烃与各种亚乙基二胺和二亚乙基三胺反应得到的二胺和三胺。
在本发明中,液态胺组合物可以相对100重量份单胺(1)和聚胺(2)总量包含10至300重量份,以40至150重量份为宜的上述具有8至22个碳原子的脂族烃基的单胺或聚胺的烯化氧加合物,例如它们的环氧乙烷加合物或环氧丙烷加合物。考虑到液体性能和乳化性能的改进,上述范围是较好的。在一起使用时,为得到液态胺组合物而需加入的具有4至18个碳原子的有机酸的混合量可以减少。即,同时使用环氧乙烷加合物可以改善液体特性。
有关上述单胺和聚胺,较好的实施方式是,具有8至22个碳原子的脂族烃基来自牛脂或氢化牛脂。
可用于本发明的具有4至18个碳原子的有机酸的例子包括具有4至18个碳原子的羧酸,具有4至18个碳原子的酸性磷酸酯和具有4至18个碳原子的含硫酸化合物。
具有4至18个碳原子的羧酸的例子包括脂肪酸和环烷酸,脂族羧酸的例子包括例如丁酸、戊酸、己酸、庚酸、辛酸和癸酸的直链饱和脂肪酸,例如异丁酸、2-甲基丁酸、3-甲基丁酸、2-甲基戊酸、3-甲基戊酸、4-甲基戊酸、2-乙基己酸、异壬酸、异癸酸、异十三烷酸、异十四烷酸、异十六烷酸和异硬脂酸的支链饱和脂肪酸,和例如癸烯酸、十一碳烯酸、十二碳烯酸、十四碳烯酸、十六碳烯酸、油酸、亚油酸和亚麻酸的不饱和脂肪酸。烯烃与一氧化碳的Koch反应得到的叔羧酸也可以使用。作为环烷酸,可以使用从原油中经碱萃取得到的环烷酸。总之,优选的是具有4至10个碳原子的支链脂族羧酸。
此外,具有4至18个碳原子的酸性磷酸酯的例子包括磷酸丁酯、磷酸戊酯、磷酸己酯、磷酸辛酯、磷酸2-乙基己酯、磷酸壬酯、磷酸癸酯、磷酸十一烷酯、磷酸十二烷酯、磷酸异十三烷酯。具有4至18个碳原子的含硫酸化合物的例子包括磺酸化合物,例如具有4至18个碳原子的α烯烃的磺酸化合物、具有4至12个碳原子的烃基的烷基苯的磺酸化合物和具有4至12个碳原子的烃基的烷基酚的磺酸化合物,和具有4至18个碳原子的醇的酸式硫酸酯。
根据本发明,具有8至22个碳原子的脂族烃基的单胺(1)的含量按重量计为5%至70%,具有8至22个碳原子的脂族烃基的聚胺(2)的含量按重量计为20%至80%,具有4至18个碳原子的有机酸的含量按重量计为10%至75%。更好的是,组份(1)的含量按重量计为10%至40%,组份(2)的含量按重量计为20%至50%,组份(3)的含量按重量计为20%至50%。以上含量可根据所用的单胺和聚胺作适当调整,但是为了获得与聚集料的优良粘附性和乳化稳定性,单胺(1)与聚胺(2)的重量含量比最好在5/95至30/70之间,更好的是在5/95至50/50之间。
根据本发明,液态胺组合物可以含水(4),其含量应不致使系统发生分离。在含水时,液态胺组合物的粘度降低,加工性由此进一步改善.水含量应以使组合物的粘度在4000mPa·s或以下为宜,更好的是2000mPa·s或以下。这种粘度下降效应取决于所用原料胺和脂肪酸的种类,在使用支链脂肪酸,例如使用具有4至10个碳原子的支链脂族羧酸时,粘度下降效应尤其大。在使用直链脂肪酸时,因为组成会形成液晶,所以会形成较大的结构,因而有时无法充分获得粘度下降效应。加入过量的水时,有时会出现浑浊,在长期保存期间,有时会形成沉淀。所述的沉淀是否容易发生受到所用原料胺的种类和脂肪酸的种类和用量所影响。所以,需要调整加入的水量,以使系统不因形成沉淀而分离。更具体的说,加入的水量为每100重量份总量的单胺(1)、聚胺(2)和有机酸(3)中加2至50重量份。即使少量的水也具有粘度降低效应,但是如果水量少于2重量份,效果不充分,而即使如果水量超过50重量份,粘度降低效果难有进一步的提高,但是会形成沉淀,使得系统倾向于分离。
根据本发明,每100重量份总量的单胺(1)、聚胺(2)和有机酸(3)中还可以含至少一元醇或多元醇之一(5)。醇对于降低液态胺组合物的粘度也有作用,其实例包括一元醇,例如甲醇、乙醇、异丙醇、丁醇、戊醇、己醇、甲基戊醇、辛醇、2-乙基己醇、异辛醇、异十三烷醇和油醇;多元醇,例如乙二醇、丙二醇、甘油、聚甘油、二乙二醇、聚乙二醇和聚丙二醇。有时,可以在与液态胺组合物混合的水或醇中溶入水溶性聚合物或酚。根据本发明,液态胺组合物还含有至少选自无机酸、乙酸和丙酸之一的酸(6),其含量为每100重量份总量的单胺(1)、聚胺(2)和有机酸(3)含0.05至10重量份。无机酸的例子包括盐酸、硫酸、硝酸和磷酸,它们可以相互混合使用。当所述的酸被加入为了降低粘度和改善加工性而加入了水的液态胺组合物中时,最大限度地减少了出现浑浊和长期保存期间形成沉淀的问题。此时,如果酸量低于0.05重量份,改善浑浊的效果不充分,另一方面,如果超过10重量份,液态胺组合物的粘度会再度上升。更好的是,酸(6)的含量在0.5至5重量份之间。
对于使用本发明的液态胺组合物作为沥青类材料的乳化剂来制备沥青等的沥青类乳液的方法没有特殊的限制。但是,实例之一包含:制备pH约1至5的本发明液态胺组合物的水溶液,将水溶液的温度升高至约30至50℃,将它与加热至120至180℃的熔融沥青混合,然后视需要加以搅拌使得化合物成为乳液。按乳化后沥青计,本发明液态胺组合物的含量在按重量计0.05至10%之间,0.1至3%更好,乳液中沥青类物质的含量在按重量计50至80%之间,60至75%更好。可用的一元酸的例子包括盐酸、硝酸、甲酸、乙酸和一氯乙酸,其含量大于所用液态胺组合物的中和当量,更为通常的是,其含量在中和当量的约1.2至1.8倍之间。
实施例
以下实施例将进一步说明本发明,但不限定本发明的范围。
制备沥青乳液并评价其性能
将表1至表4所示的胺组合物转化成盐酸胺形式的水溶液。调节盐酸的量使得水溶液的pH约为2。将415克所述水溶液加热至45℃,将其与600克加热至145℃熔化、针入度为80至100的直镏沥青一起通过harrel型均质器。由此获得沥青乳液。此例中,加入的盐酸胺被调节为占沥青乳液总重量的0.15%。对于此沥青乳液来说,乳化稳定性和与聚集料的粘附性是利用下述方法测定的。结果列于表1至4,所用胺的化学结构显示在表5中。表中所示组成的值是重量百分比,除非另作说明。而且,胺组合物的固化温度是根据JIS K2269通过进行每1℃的流度评价来测定的,粘度是利用Tokyo Keiki Co.,Ltd.制造的B型旋转粘度计测定的。
[乳化稳定性测试]
将约250毫升制备好的沥青乳液转移到ASTM D244-86所述的筒状容器内,然后在约20℃的室温下静置一天。从筒的上部和下部各取样50克乳液,测定蒸发残留百分比。上部和下部的蒸发残留百分比差异说明了乳化稳定性。可以这样认为,差异越小,乳化稳定性越好。蒸发残留百分比是如下测定的。即,取出的沥青乳液样品在ASTM D244-86规定的容器中称重,然后利用电加热器边搅拌边加热30分钟。在观察认为没有水存在后,再在160℃继续加热1分钟。然后,样品在室温下静置,然后测定生成的残留物的重量(克)。以残留物与样品之比作为蒸发残留百分比。
[与聚集料的粘附性测试]
10至15毫米大小的碎石灰石在水中浸泡1分钟,取出后立即在沥青乳液中浸泡1分钟。然后,取出这些碎石并列放置在14号筛(1.4毫米)上,然后在室温下静置5小时。然后,将其在80℃的热水中浸泡1小时,然后观察沥青的剥落情况。目测石头表面被沥青膜覆盖的面积的比例,然后计算粘附面积(%)。以此表示与聚集料的粘附性(%)。该值越大,粘附性越强,这正是人们所希望的。但是,一次测试使用的碎石数为10,以10颗碎石的平均值作为与聚集料的粘附性。
表1
实施例 | 比较例 | |||||||||||||||||
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 1 | 2 | 3 | 4 | |
(单胺/聚胺)牛脂单胺 | 7 | 15 | 15 | 15 | 26 | 24 | 24 | 17 | 14 | 31 | 37 | 2 | 55 | 72 | ||||
十八烷基单胺 | 7 | 37 | ||||||||||||||||
氢化牛脂单胺 | 7 | |||||||||||||||||
牛脂二胺 | 36 | 36 | 36 | 32 | 32 | 32 | 25 | 26 | 23 | 30 | 18 | 21 | 18 | 18 | 72 | 70 | 17 | |
牛脂三胺 | 29 | 29 | 29 | 25 | 20 | 17 | ||||||||||||
牛脂二胺EO加合物 | 25 | 35 | 30 | 25 | 20 | 13 | 17 | |||||||||||
牛脂二胺PO加合物 | 25 | |||||||||||||||||
单胺/聚胺的重量比 | 10/90 | 10/90 | 10/90 | 21/79 | 21/79 | 21/79 | 30/70 | 30/70 | 33/67 | 25/75 | 31/69 | 43/57 | 51/49 | 51/49 | 0/100 | 3/97 | 76/24 | 100/0 |
胺总量 | 72 | 72 | 72 | 72 | 72 | 72 | 86 | 80 | 72 | 58 | 45 | 72 | 72 | 72 | 72 | 72 | 72 | 72 |
(有机酸)2-乙基己酸 | 28 | 28 | 28 | 28 | 28 | 28 | 14 | 20 | 28 | 42 | 55 | 28 | 28 | 28 | 28 | 28 | 28 | 28 |
固化温度(℃) | 10 | 12 | 12 | 11 | 0 | -2 | 10 | 7 | 3 | -5 | -4 | 13 | 12 | 9 | 20 | 21 | 19 | 23 |
粘度(cP,25℃) | 1100 | 1500 | 1500 | 1600 | 740 | 520 | 1300 | 1050 | 1100 | 850 | 1000 | 2600 | 2200 | 1500 | 5200 | 5400 | 4700 | 5700 |
乳化稳定性(%) | 0.8 | 0.4 | 0.5 | 0.6 | 0.7 | 0.6 | 0.7 | 0.6 | 0.6 | 0.6 | 0.4 | 0.4 | 0.5 | 0.8 | 2.5 | 2 | 3.2 | 7.6 |
与聚集料的粘附性(%) | 95 | 100 | 100 | 100 | 95 | 100 | 100 | 95 | 100 | 95 | 100 | 100 | 95 | 100 | 80 | 85 | 80 | 70 |
表2
实施例 | 比较例 | ||||||||||||||
15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 5 | 6 | 7 | 8 | 9 | |
(单胺/聚胺)*1胺总量 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 |
单胺/聚胺的重量比 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 |
(有机酸)36%盐酸 | 31 | ||||||||||||||
乙酸 | 31 | ||||||||||||||
二十二碳烷酸 | 31 | ||||||||||||||
异丙醇 | 31 | ||||||||||||||
2-乙基己醇 | 31 | ||||||||||||||
丁酸 | 31 | ||||||||||||||
异丁酸 | 31 | ||||||||||||||
己酸 | 31 | ||||||||||||||
3-甲基戊酸 | 31 | ||||||||||||||
2-乙基己酸 | 31 | ||||||||||||||
异十三烷酸 | 31 | ||||||||||||||
异硬脂酸 | 31 | ||||||||||||||
2-乙基己基磷酸 | 31 | ||||||||||||||
十二烷基苯磺酸 | 31 | ||||||||||||||
十二碳烯磺酸 | 31 | ||||||||||||||
固化温度(℃) | 15 | 12 | 12 | 11 | 0 | -2 | 11 | 10 | 8 | 12 | 60 | 51 | 78 | 28 | 30 |
粘度(cP,25℃) | 1100 | 1500 | 1500 | 1600 | 740 | 520 | 1700 | 1300 | 1050 | 2200 | - | - | - | - | - |
乳化稳定性(%) | 0.3 | 0.4 | 0.5 | 0.6 | 0.4 | 0.6 | 0.5 | 0.5 | 0.6 | 0.5 | 0.5 | 0.5 | 0.6 | 0.4 | 0.6 |
与聚集料的粘附性(%) | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
*1:重量比为30/40/30的牛脂单胺/牛脂二胺/牛脂三胺混合物
表3
实施例 | ||||||||||||||||
25 | 26 | 27 | 28 | 29 | 30 | 31 | 32 | 33 | 34 | 35 | 36 | 37 | 38 | 39 | 40 | |
(单胺/聚胺)牛脂单胺 | 8 | 8 | 8 | 8 | 8 | 8 | 21 | 21 | 21 | |||||||
氢化牛脂单胺 | 19 | 19 | 19 | 19 | 19 | 12 | 12 | |||||||||
牛脂二胺 | 38 | 38 | 38 | 38 | 38 | 38 | 35 | 35 | 35 | |||||||
氢化牛脂二胺 | 32 | 32 | 32 | 32 | 32 | 28 | 28 | |||||||||
牛脂三胺 | 13 | 13 | 13 | |||||||||||||
氢化牛脂三胺 | 13 | 13 | 13 | 13 | 13 | 23 | 23 | |||||||||
牛脂二胺EO加合物 | 30 | 30 | 30 | 30 | 30 | |||||||||||
牛脂二胺PO加合物 | 30 | |||||||||||||||
单胺/聚胺的重量比 | 10/90 | 10/90 | 10/90 | 10/90 | 10/90 | 10/90 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 19/81 | 19/81 |
胺总量 | 76 | 76 | 76 | 76 | 76 | 76 | 69 | 69 | 69 | 64 | 64 | 64 | 64 | 64 | 63 | 63 |
(有机酸)2-乙基己酸 | 24 | 24 | 24 | 24 | 24 | 24 | 31 | 31 | 36 | 36 | 36 | 36 | 36 | 36 | 36 | 36 |
水*1乙醇*1丙二醇*1聚乙二醇(MW400)*1 | - | 3 | 6 | 10 | 55 | 15 | - | 2 | 5 | - | 5 | 18 | 35 | 45 | 3515 | 1817 |
固化温度(℃) | 4 | 4 | 4 | 3 | 2 | 3 | 7 | 7 | 6 | 12 | 12 | 10 | 10 | 10 | 8 | 8 |
粘度(cP,25℃) | 980 | 680 | 420 | 310 | 200 | 230 | 1700 | 1000 | 530 | 5800 | 1900 | 620 | 370 | 250 | 220 | 480 |
乳化稳定性(%) | 0.7 | 0.7 | 0.5 | 0.6 | 0.6 | 0.6 | 0.5 | 0.6 | 0.4 | 0.3 | 0.3 | 0.5 | 0.6 | 0.5 | 0.4 | 0.5 |
与聚集料的粘附性(%) | 95 | 95 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 1 00 | 100 | 100 | 100 | 100 | 100 | 100 |
*1:相对于100重量份单胺、聚胺和有机酸总量的重量份数
表4
实施例 | ||||||||
41 | 42 | 43 | 44 | 45 | 46 | 47 | 48 | |
(单胺/聚胺)牛脂单胺 | 21 | 21 | 21 | 21 | 21 | 21 | 21 | 21 |
牛脂二胺 | 35 | 35 | 35 | 35 | 35 | 35 | 35 | 35 |
牛脂三胺 | 13 | 13 | 13 | 13 | 13 | 13 | 13 | |
牛脂二胺PO加合物 | 13 | |||||||
单胺/聚胺的重量比 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 | 30/70 |
胺总量 | 69 | 69 | 69 | 69 | 69 | 69 | 69 | 69 |
2-乙基己酸 | 31 | 31 | 31 | 31 | 31 | 31 | 31 | 31 |
水*1 | 20 | 20 | 20 | 20 | 20 | 20 | 20 | 20 |
硫酸*1 | 0.5 | 1.9 | 3.8 | |||||
乙酸*1 | 2.3 | 4.6 | 2.3 | |||||
丙酸*1 | 5.8 | |||||||
固化温度(℃) | 7 | 5 | 2 | 3 | 3 | 5 | 5 | 0 |
粘度(cP,25℃) | 260 | 200 | 180 | 160 | 170 | 170 | 170 | 150 |
外观(25℃) | 完全混浊 | 基本透明 | 基本透明 | 透明 | 透明 | 透明 | 透明 | 透明 |
乳化稳定性(%) | 0.5 | 0.6 | 0.7 | 0.6 | 0.5 | 0.5 | 0.8 | 0.6 |
与聚集料的粘附性(%) | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
*1:相对于100重量份单胺、聚胺和有机酸总量的重量份数
表5
实施例中所用的胺的化学结构
从表格中的结果可以清楚地看出,本发明的液态胺组合物能够使得沥青乳液之类的沥青类乳液具有优于常规产品的乳化稳定性和与聚集料的粘附性。此外,本发明液态胺组合物还具有优良的加工性能。
Claims (7)
1.一种用作沥青的乳化剂的液态胺组合物,它包含
(1)按重量计,5%至70%具有8至22个碳原子的脂族烃基的单胺,所述单胺选自癸胺、十二烷基胺、十四烷基胺、十六烷基胺、十八烷基胺、二十二烷基胺、牛脂胺或氢化牛脂胺,
(2)按重量计,20%至80%具有8至22个碳原子的脂族烃基的聚胺,所述聚胺选自N-氨基丙基烷基胺,N-烷基二亚丙基三胺或N-烷基三亚丙基四胺。
(3)按重量计,10%至75%具有4至18个碳原子的有机酸,
所述单胺与聚胺的重量比在5/95至33/67,
所述有机酸选自羧酸,酸性磷酸酯或硫酸化合物。
2.根据权利要求1所述的胺组合物,所述N-氨基丙基烷基胺选自N-氨基丙基癸基胺、N-氨基丙基十二烷基胺、N-氨基丙基十四烷基胺、N-氨基丙基十六烷基胺、N-氨基丙基十八烷基胺、N-氨基丙基二十二烷基胺、N-氨基丙基牛脂胺或N-氨基丙基氢化牛脂胺,所述N-烷基二亚丙基三胺选自N-癸基二亚丙基三胺、N-十二烷基二亚丙基三胺、N-十四烷基二亚丙基三胺、N-十六烷基二亚丙基三胺、N-十八烷基二亚丙基三胺、N-二十二烷基二亚丙基三胺、N-牛脂基二亚丙基三胺或氢化N-牛脂基二亚丙基三胺,所述N-烷基三亚丙基四胺选自N-癸基三亚丙基四胺、N-十二烷基三亚丙基四胺、N-十四烷基三亚丙基四胺、N-十六烷基三亚丙基四胺、N-十八烷基三亚丙基四胺、N-二十二烷基三亚丙基四胺、N-牛脂基三亚丙基四胺或氢化N-牛脂基三亚丙基四胺。
3.根据权利要求1所述的胺组合物,其中所述的羧酸是具有4至18个碳原子的脂族羧酸或环烷酸。
4.根据权利要求1所述的胺组合物,其中所述的聚胺是N-氨基丙基烷基胺。
5.根据权利要求1所述的胺组合物,其中含有相对于100重量份单胺和聚胺总量之10至300重量份的所述单胺或聚胺的烯化氧加合物。
6.根据权利要求1所述的胺组合物,其中单胺、聚胺和/或其烯化氧加合物中的脂族烃基选自自牛脂,氢化牛脂或十八烷基。
7.根据权利要求1所述的胺组合物,其中所述的羧酸是具有4至10个碳原子的支链脂族羧酸。
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DE19959314A1 (de) * | 1999-12-09 | 2001-06-13 | Cognis Deutschland Gmbh | Verwendung von Emulgatoren |
MXJL01000012A (es) * | 2001-05-18 | 2002-11-27 | Quimikao S A De C V | Composicion emulsificante para preparar emulsiones de asfalto en agua. |
ES2192469B1 (es) * | 2002-01-14 | 2004-06-16 | Kao Corporation, S.A. | Poliaminas ramificadas para emulsiones de betun. |
US7213446B2 (en) * | 2004-08-27 | 2007-05-08 | Semmaterials, L.P. | Method of selecting a bituminous emulsion based on its coalescence |
ES2358334T3 (es) * | 2005-01-19 | 2011-05-09 | Akzo Nobel N.V. | Procedimiento para la fabricación de una mezcla de betún-agregado adecuada para la pavimentación de carreteras y un compuesto poliamina y su uso. |
IES20080233A2 (en) * | 2008-03-31 | 2009-09-30 | Lagan Technology Ltd | A method for the emulsification of bitumen |
CN101745340B (zh) * | 2008-12-08 | 2012-01-11 | 中国石油天然气股份有限公司 | 一种阳离子沥青乳化剂及其制备方法和应用 |
CN101845228B (zh) * | 2010-05-20 | 2011-11-16 | 北京万博汇佳科贸有限公司 | 一种阳离子沥青乳化剂的组成、制备方法及其应用 |
MX339501B (es) * | 2010-11-04 | 2016-05-20 | Quimikao S A De C V | Aditivo modificador de las propiedads reologicas del asfalto, para su uso en mezclas asfalticas tibias. |
US9534146B2 (en) | 2011-06-24 | 2017-01-03 | Akzo Nobel Chemicals International B.V. | Additives for bitumen containing compositions |
FR2992966B1 (fr) * | 2012-07-06 | 2015-06-19 | Ceca Sa | Emulsifiants pour emulsions de bitume |
US9637868B2 (en) | 2012-10-31 | 2017-05-02 | Akzo Nobel Chemicals International B.V. | Phosphated compounds as adhesion promoters |
CN103289104B (zh) * | 2013-03-21 | 2015-01-21 | 镇江金阳道路材料科技发展有限公司 | 一种可乳化sbs改性沥青的阳离子沥青乳化剂及其制备方法 |
US11447637B2 (en) * | 2019-03-15 | 2022-09-20 | Ecolab Usa Inc. | Asphalt emulsion composition and method of treating a pavement surface |
US20230407094A1 (en) * | 2022-06-21 | 2023-12-21 | Ascend Performance Materials Operations Llc | Asphalt additives with multiple amines |
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US2690978A (en) * | 1950-10-04 | 1954-10-05 | Atlas Powder Co | Bituminous emulsion |
DE1072915B (de) * | 1956-05-25 | 1960-01-07 | Societe Chimique Et Routiere De La Gironde, Paris | Herstellung einer kalt einbaufähigen, kationischen, wäßrigen Emulsion auf Basis von Verschnittbitumen |
US3518101A (en) * | 1967-05-23 | 1970-06-30 | Atlantic Richfield Co | Cationic asphalt emulsions |
US3975295A (en) * | 1972-05-23 | 1976-08-17 | Ashland Oil, Inc. | Liquid amine compositions |
JPS53117014A (en) * | 1977-03-24 | 1978-10-13 | Kao Corp | Emulsifier for asphalt emulsions |
US4430127A (en) * | 1981-10-21 | 1984-02-07 | Carstab Corporation | Epoxylated amine asphalt anti-stripping agent |
JPS59123523A (ja) * | 1982-12-28 | 1984-07-17 | Kao Corp | アスフアルト乳剤用の液状乳化剤 |
FR2629364B1 (fr) * | 1988-03-30 | 1990-11-30 | Ceca Sa | Nouvelles compositions amines cationactives a proprietes physiques ameliorees : leur application, par exemple a la realisation d'emulsions bitumineuses |
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