CN1005265B - 新型铝体系偶联剂 - Google Patents
新型铝体系偶联剂 Download PDFInfo
- Publication number
- CN1005265B CN1005265B CN85102942.6A CN85102942A CN1005265B CN 1005265 B CN1005265 B CN 1005265B CN 85102942 A CN85102942 A CN 85102942A CN 1005265 B CN1005265 B CN 1005265B
- Authority
- CN
- China
- Prior art keywords
- coupling agent
- acid
- aluminium
- tri
- reaction
- 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
Links
- 229910052782 aluminium Inorganic materials 0.000 title claims abstract description 71
- 239000007822 coupling agent Substances 0.000 title claims abstract description 60
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 235000010210 aluminium Nutrition 0.000 claims description 69
- 239000004411 aluminium Substances 0.000 claims description 37
- -1 aluminum alkoxide Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 230000000630 rising effect Effects 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 4
- 125000004185 ester group Chemical group 0.000 claims 4
- 230000004913 activation Effects 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical group [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 claims 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 238000005829 trimerization reaction Methods 0.000 claims 1
- 150000004645 aluminates Chemical class 0.000 abstract description 12
- 238000012545 processing Methods 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 8
- 239000004033 plastic Substances 0.000 abstract description 7
- 229920003023 plastic Polymers 0.000 abstract description 7
- 239000011152 fibreglass Substances 0.000 abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 6
- 239000011248 coating agent Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 239000005060 rubber Substances 0.000 abstract description 5
- 239000011230 binding agent Substances 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 238000012986 modification Methods 0.000 abstract description 2
- 230000004048 modification Effects 0.000 abstract description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- 235000010216 calcium carbonate Nutrition 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000013459 approach Methods 0.000 description 10
- 229910000019 calcium carbonate Inorganic materials 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 3
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 2
- UNYKBGSYYHWZCB-UHFFFAOYSA-N 2-tetradecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O UNYKBGSYYHWZCB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
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- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
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- 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 2
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/418—Preparation of metal complexes containing carboxylic acid moieties
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
本发明系新型铝体系偶联剂的合成方法和应用的发明。目的是提供一个易合成、成本低而性能好的新偶联剂体系。为此发明了合成具有当水解稳定性和较小缔合性的可作偶联剂的铝酸酯、低聚铝酸酯及其衍生物的方法，并将合成的新型铝体系偶联剂应用于含无机物和有机物的复合体系的制品如塑料、橡胶、涂料、粘结剂、玻璃钢、层压制品、油墨和鞋油等的加工以及各种材料的表面改性等方面，达到改善加工性能、减少能耗、提高质量、降低成本、发展新产品和开拓新用途等目的。
Description
本发明系新型铝体系偶联剂的合成方法和应用的发明。
偶联剂（Coupling agent）又称促粘剂（Adhesive Promoter）或表面处理剂（Primer）。典型的偶联剂是分子中至少含有两类化学基团并能在某些混合或粘合体系中分别与两相物质发生化学反应、物理化学作用或物理作用而使两相物质紧密偶联结合的一类化学物质或产品。
三十多年来，偶联剂已日益广泛应用于塑料、橡胶、涂料、粘结剂、玻璃钢、层压制品、油墨、鞋油、电器、织品以及各种材料的表面改性等方面，起到改善加工性能、减少能耗、提高质量和降低成本的作用，并为开发新产品、开拓新用途提供了新的途径，成为愈来愈重要的一类精细化工产品和助剂。
五十年代美国杜邦公司（Du Pont）首先发明了以“沃兰”（Volan）系列产品为代表的铬体系偶联剂（U.S.P.352740），曾大量用于增强不饱和聚酯的玻璃纤维表面处理。因为铬离子的毒性和污染，以后无重大发展。大约与此同时，美国联合碳化物公司（Union Carbide）发明了以氨基硅烷为代表的硅体系偶联剂（J.G.Marsdenet al.，“Adherends and Bonding Technology”Section C，P.642-652）。主要用于以硅酸盐、二氧化硅为填料的工程塑料和橡胶的加工及其性能改进，取得很好的效果。至今已有近百个品种。七十年代美国肯里奇石油化学公司（Kenrich Petrochemical）研制成功以异丙氧基三异硬酯酰氧基钛（TTS）为代表的钛体系偶联剂（S、J、Monte et al.，32nd AnnualTechnical Conference，Section 4-E，1977，P.1-29）。主要适用于以碳酸盐，硫酸盐和金属氧化物为填料的聚烯烃塑料、涂料和粘结剂等方面，发展相当迅速，现在也有六十多个品种。1983年美国卡文顿化学公司（Cavedon Chemical）推出了以七个锆铝酸酯为代表的锆铝体系偶联剂（L.B.Cohen，Plastics Engineering.1983，39（11），29-32）。据称某些性能优于硅、钛体系偶联剂，但成本比硅烷偶联剂还高一半。
还有一些有机化合物以及含有其他金属原子的有机金属化合物也被作为偶联剂应用，但其性能和重要性都未能和上述四个体系的偶联剂相比。
此外，近年还提出将有机铝螯合物用作涂料催干剂（B.P.1462610）。电路板表面的促粘剂（JP、82、36、759）、增强环氧树脂的玻璃纤维表面处理剂（JP、83、79、023）、涂层对玻璃的促粘剂（C、A、99、214185g）、丙烯酸酯-甲基丙烯酸酯共聚物中玻璃纤维表面处理剂（C、A、97、56624b）以及代替胺基硅烷偶联剂用于改善大规模集成电路与聚酰亚胺的粘结性能（J.Electro Chemical Soc.，1982，129，2278-2282）等。至于将铝酸酯用作偶联剂的研究，由于铝酸酯较大的水解性，直到一九八三年还被认为不能作为偶联剂（D.H、Solomon et al.，“Chemistry of Pigments and Fillars”，John Wiley ＆ Sons，New York，1983，109-148）。
总之，迄今为止，国内外偶联剂的研究、生产和应用仍以硅体系和钛体系最为重要。但是这两大体系偶联剂几乎都是以其相应的无水氯化物为起始原料，成本高，腐蚀性大，工艺复杂，以致最终产品价格高，妨碍了它们的进一步推广应用。
鉴此，本发明的目的是提供一个易合成、成本低而又性能好的新偶联剂体系。
本发明选择原料丰富、价格低廉的三价元素铝作为偶联剂的中心原子，利用金属铝具有活泼并呈两性性质的特点，直接以金属铝为起始原料，经一步反应即获得中间体三烷氧基铝，再与具有一定链长和空间位阻的，或还含有其他官能团的含羟基、酚基、羧基、各种磷酸基、各种磺酸基、各种硫酸基等酸性反应基团的物质或其酯类、醚类和酸酐类物质进行反应，得到具有适当水解稳定性的铝酸酯或其衍生物。与此同时，采取适当满足中心铝原子配位数的方法克服或减少铝酸酯或其衍生物的缔合性，使制得的铝酸酯或其衍生物具有可以作为偶联剂应用所必需的理化性质。
基于上述发明构思，本发明的新型铝体系偶联剂具有如式（Ⅰ）所示的基本结构：
式（Ⅰ）
式（Ⅰ）中Al为偶联剂的中心铝原子;R为碳原子数为1-6的直链或支链或环状的脂烃基或芳烃基;O为氧原子，因此R-O-可以，是甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、各种异构戊氧基、各种异构己氧基及苯氧基等;L1、L2和L3为相同的或不同的或混合的含孤对电子原子的有机或无机的配位体，如酮类、醛类、胺类、醇类、含N、O等原子的杂环类以及水等分子或基团;E-A-和F-B-为相同的或不同的或混合的由二个具有不同功能结构部分组成的直链或支链或环状的长链基。其中A和B是相同的或不同的可以直接与中心铝原子以共价键结合的原子或原子团，如氧及各种酰氧基等。而E和F是含6-20个或更多碳原子的具有一定空间位阻或还含有可与聚合物分子链发生化学或物理化学作用的其他官能团，如双键、硫键、异氰酸、偶氮或叠氮基的直链、支链或环状长链。因此E-A-和F-B-长链基可以是含6-20个或更多碳原子的有一定空间位阻的，或还含有其他官能团的直链或支链或环状的脂（芳）氧基、脂（芳）酰氧基、各种磷酸酯酰氧基、各种烷基磺酰氧基、各种烷基硫酰氧基、各种酯的单羟氧基或单酰氧基以及它们的各种取代衍生物。
应当着重指出，具有上述基本结构的新型铝体系偶联剂的特征，除了中心原子为铝之外还有：
（1）.如果E-A-和F-B-两个长链基中E和F部分的空间位阻足够大或E和F中距离A或B为3-4个原子处是含孤对电子原子时，可以相应省去L1或L2或L3，因此本发明的新型铝体系偶联剂中直接与中心铝原子连接的基团总数目为3-6个，一般是4-5个，其中三个以共价键结合，其余以配位键连接。
（2）.选择E-A-和F-B-的结构、链长和空间位阻可以调节产物的水解稳定性。
（3）.选择L1、L2和L3的结构类型、大小和数目并与（2）配合可以克服或减少最终产物的缔合性。
（4）.选择R-O-中R的不同结构、碳原子数和位阻。可以调节产物的水解反应活性。
（5）.若将中间体三烷氧基铝控制适当的水解缩合可得聚合度为2-4的低聚烷氧基铝，进而合成得到相应的低聚的新型铝体系偶联剂。其结构如式（Ⅱ）所示。控制其聚合度也可以调节水解稳定性。
式（Ⅱ）
式（Ⅱ）中B′为式（Ⅰ）中B除去氧原子的其余部分。
显然本发明的新型铝体系偶联剂在结构上不但与已知的铬、硅、钛、锆铝体系偶联剂以及其他作为偶联剂应用的有机化合物，包括有机铝螯合物都有根本的不同。而且与已有的主要用作涂料催干剂的各种铝酸酯（B.P.1462610）也有明显的区别。
合成（制备或生产）本发明的新型铝体系偶联剂的方法及其步骤是：
一、中间体合成：
1、三烷氧基铝：各种形式的金属铝，加入1-10倍理论反应量的含1-6个碳原子的低级醇（酚）如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、叔丁醇、各种异构戊醇、各种异构己醇和苯酚等，必要时可添加金属铝重量0.01-1%的催化剂，如铜、汞、银、金的氯化物或醋酸盐等或它们与溴、碘等还原剂的配合。在20-160℃下迴流反应2-8小时。常压下蒸出过量低级醇，然后减压蒸出三烷氧基铝。反应式为：
2Al+6RoH→2Al（OR）3+3H2↑ 式（Ⅲ）
三烷氧基铝产率为45-90%，低级醇回收率在85-98%之间。
2、低聚烷氧基铝：将三烷氧基铝或溶于适量惰性溶剂中，加热、迴流、逐渐通入三烷氧基铝重量0.001-8.8%的水蒸气，保持迴流1-4小时，常压蒸出溶剂，添加微量酸或碱或氧化物等缩合催化剂，如硫酸、盐酸、磷酸、氢氧化钠、氢氧化钙、氧化镁和氧化钙等，减压下升温迴流，并逐渐将温度升高到160-200℃，反应时间2-4小时，最后继续升温，将低聚烷氧基铝蒸出。反应式为：
Al（OR）3+H2O→Al（OR）2（OH）+ROH 式（Ⅳ）
低聚烷氧基铝产率为10-80%
二、交换反应：
1、铝酸酯：一克分子三烷氧基铝，加二克分子的F-B-H（或E-A-H或其混合物），必要时加（1-3）克分子L（即L1、L2、L3或其混合物）和适量惰性溶剂，于40-160℃下迴流0.5-4小时后，蒸出低沸产物和溶剂。反应式为
n＝1-4
低聚铝酸酯产率接近100%。
按照本发明的新型铝体系偶联剂的八个系列，其合成（制备或生产）方法中所选用的F-B-H或E-A-H可以是：
1、烷氧系列：各种醇及其取代衍生物，如辛醇、癸醇、月桂醇、豆蔻醇、软脂醇、硬脂醇、油醇、亚油醇、亚麻油醇等脂肪醇及其异构体或混合物。还有薄荷醇、萜烯醇、松油醇、香叶醇、芳樟醇、橙花醇、
牛儿苗醇等萜醇以及十二烷基苯甲醇、邻甲氧基苯甲醇和糠醇等。
2、酚氧系列：各种酚及其取代衍生物，如十二烷基苯酚、二（十二烷基）苯酚、三（十二烷基）苯酚、十二烷基甲苯酚、2，5-二甲基，4-十二烷基苯酚、十四烷基苯酚、二（十四烷基）苯酚、三（十四烷基）苯酚、3-（十五碳二烯基）苯酚、3-（十五碳二烯基）5-羟基苯酚、十六烷基苯酚、二（十六烷基）苯酚、对异丙基苯酚等。
3、酰氧系列：各种羧酸及其取代衍生物。如辛酸、癸酸、月桂酸、豆蔻酸、软脂酸、硬脂酸、异硬脂酸、油酸、亚油酸、亚麻油酸、蓖麻油酸、环烷酸、妥儿油（Tall Oil）混合酸，还有枞酸、乳香脂酸等树脂酸以及十二烷基苯甲酸等。
4、磷酸酯酰氧系列：如二（异）辛基磷酸酯、二（异）辛基亚磷酸酯、二（异）辛基焦磷酸酯、二（异）辛基焦亚磷酸酯等。
5、烷磺酰氧系列：各种脂磺酸、苯磺酸及其取代衍生物。如十二烷基磺酸、十二烷基苯磺酸、二（十二烷基）苯磺酸、三（十二烷基）苯磺酸、十四烷基磺酸、十四烷基苯磺酸、二（十四烷基）苯磺酸、十六烷基磺酸、十六烷基苯磺酸、十八烷基磺酸、十八烷基苯磺酸等。
6、烷基硫酰氧系列：如十二烷基硫酸、十二烷基亚硫酸、十四烷基硫酸、十六烷基硫酸、十八烷基硫酸等。
7、酯单羟氧或单酰氧系列：邻苯二甲酸一丁（辛）酯、邻苯二甲酸酐、顺丁烯二酸一丁（辛）酯、顺丁烯二酸酐、甘油二脂酸酯、丙二醇-酯、各种低聚乙二醇一酯和各种低聚丙二醇一酯等。
8、混合系列：上述七个系列所用的F-B-H或E-A-H之间二种或几种的混合。
由上可见，本发明的新型偶联剂与已有的铬、硅、钛、锆铝体系及其他偶联剂相比，最根本的不同在于中心原子是铝，正因为这一点，本发明的新型铝体系偶联剂的合成（制备或生产）方法具有以下优点：
1、可以直接以原料丰富、价格便宜的金属铝为起始原料，经一步反应就得到中间体三烷氧基铝或进而水解缩合成低聚烷氧基铝。
2、中间体三烷氧基铝或其低聚体的合成反应快速、工艺简单、产率高，既无腐蚀性又大幅度降低生产成本。
3、由于上述二点，最终产物成本低。
4、由于采用含有6-20个或更多碳原子的具有一定空间位阻的长链为侧基、控制中间体一定聚合度并适当满足中心铝原子配位数的方法解决了作为偶联剂的铝酸酯、低聚铝酸酯及其衍生物所需的水解稳定性和较小的缔合性问题。
此外本发明的新型铝体系偶联剂无毒、颜色比相应的钛酸酯偶联剂浅，而且也有不同系列和品种，性能各异，可适应于各种不同的使用目的和要求。
本发明的新型铝体系偶联剂主要可以应用于两大方面：
一、在含无机物、有机物的多元复合体系，如塑料、橡胶、涂料、粘结剂、玻璃钢、层压制品、油墨和鞋油等制品中作为典型偶联剂应用。两种基本的使用方法是：
1、预处理法：将填料如轻质碳酸钙、重质碳酸钙、三水合氧化铝、二氧化硅、二氧化钛、氧化锌、硫酸钡、石膏粉、立德粉等，颜料如钛白粉、炭黑、铁红、铬黄、酞菁兰等和其重量0.1-2.5%的新型铝体系偶联剂混合，在适当的混合装置中于0°-150℃下搅拌2-30分钟，即制得相应的改性填料或颜料。使用时再与制品其他组分配合、加工。
2、直接加入法：在含无机物、有机物的多元复合体系的制品生产过程中直接掺入一定量的新型铝体系偶联剂。
新型铝体系偶联剂应用于这方面可以明显降低体系粘度、改善加工性能、减少能耗、增加填料用量、降低成本、提高质量或者增加体系粘度、防止沉降和流挂等。
二、作为促粘剂或表面处理剂处理各种材料表面，如填料、颜料、色谱担体、亲水聚合物、塑料、金属、岩石、水泥、玻璃、竹木、织品和电器表面处理，以改变表面性质或促进与其他材料的粘结，使用方法是用适当溶剂稀释后喷涂、刷涂或浸渍。
兹列举本发明的新型铝体系偶联剂的合成和应用实例如下：
例1：13.5克金属铝屑，加360克无水异丙醇和0.0959克氯化高汞，于80℃下迴流，反应2-8小时，常压下蒸出过量异丙醇，减压（1-10mmHg），收集110-140℃蒸出的三异丙氧基铝，产率80-95%。
称取20.4克三异丙氧基铝，57.9克甲苯、4.5克乙胺，于搅拌下分次加入54.0克十八烷醇，于110-130℃下迴流0.5-1小时，常压下蒸出溶剂和异丙醇，得异丙氧基二（十八烷氧基）铝62.4克，产率接近100%。
例2：称取20.4克三异丙氧基铝，50.3克苯、14.6克二乙胺，于搅拌下逐滴加入56.5克油酸，于80-90℃下迴流0.5-1小时，常压下蒸出苯和异丙醇，得79.5克异丙氧基二油酰氧基二（二乙胺）络铝，产率接近100%。
例3：称取20.4克三异丙氧基铝、60.8克二甲苯。搅拌下逐滴加入64.4克磷酸二异辛酯，在120-130℃迴流0.5-1小时，常压下蒸出二甲苯和异丙醇，得异丙氧基二（二异辛基磷酸酰氧基）铝72.8克，产率接近100%。
例4：称取20.4克三异丙氧基铝、23.6克松节油。搅拌下分次加入27.2克对异丙基苯酚。在130-140℃下迴流0.5-1小时，常压下蒸出松节油和异丙醇，得异丙氧基二（对异丙基苯氧基）铝35.6克，产率接近100%。
例5：称取20.4克三异丙氧基铝、64.4克二甲苯。搅拌下逐渐加入68.0克十二烷基甲苯磺酸，在120-130℃下迴流0.5-1小时，常压下蒸出二甲苯和异丙醇，得异丙氧基二（十二烷基甲苯磺酰氧基）铝76.4克，产率接近100%。
例6：称取20.4克三异丙氧基铝、40.0克二甲苯，搅拌下分次加入19.6克顺丁烯二酸酐，于120°-130℃下迴流0.5-1小时，常压下蒸出溶剂，得40.0克异丙氧基二（顺丁烯二酸单异丙醇酯酰氧基）铝，产率接近100%。
例7：称取20.4克三异丙氧基铝，加入119.8克苯，搅拌下加入123.3克甘油二亚麻油酸酯。于80-90℃下迴流0.5-1小时。常压下蒸出苯和异丙醇，得131.8克异丙氧基，二（甘油二亚麻油酸酯单羟氧基）铝，产率接近100%。
例8：称取20.4克三异丙氧基铝、51.6克二甲苯，搅拌下分次加入28.3克油酸和27.0克十八烷醇，于120-130℃迴流0.5-1小时，常压下蒸出溶剂和异丙醇，得63.6克异丙氧基油酰氧基，十八烷氧基铝，产率接近100%。
例9：含水量低于0.5%的轻质碳酸钙100份。添加本发明的LD-429偶联剂0.8份。在高速混合机中，于20-80℃下高速搅拌10分钟，得改性轻质碳酸钙。
例10：含水量低于0.5%的重质碳酸钙100份。添加本发明的LD-429偶联剂0.8份，在高速混合机中。于20-80℃下高速搅拌10分钟，得改性重质碳酸钙。
例11：氧化锌50份与石蜡油100份混匀后体系粘度大于5×104厘泊（28℃），添加氧化锌重量1%，本发明的LD-429偶联剂后，体系粘度下降至440厘泊（28℃）。
例12：轻质碳酸钙50份与石蜡油100份混匀后，体系粘度大于8.5×104厘泊（17.5℃），添加轻质碳酸钙重量1%。本发明的LD-429偶联剂后，体系粘度下降至690厘泊（17.5℃）。
例13：聚乙醇薄膜浸于5%本发明的LD-428偶联剂的石油醚溶液中，在60-90℃下迴流处理五分钟。用无水异丙醇洗涤数次。薄膜表面由亲水性变为憎水性。
例14：在聚氯乙烯微孔泡沫拖鞋配方中，采用例9制得的改性轻质碳酸钙为填料，填充量可从原来的0～15份增加到40～60份，不影响加工性能和产品主要性能指标（见表1）。在配方与加工条件完全一样的条件，添加新型铝体系偶联剂LD-429的制品性能比未加偶联剂的明显改善（见表1中1#与6#）。
例15：在改性聚乙烯交联发泡鞋底配方中采用例9制得的改性轻质碳酸钙为填料，填充量由原来的5-10份增加到40份，不影响加工性能和产品主要性能指标（见表2）。
例16：在聚氯乙烯微孔泡沫拖鞋鞋带上采用例9制得的改性轻质碳酸钙为填料，填料量从原来的15份增加到30～50份，不影响加工性能而且其余指标均超过标准（见表3）。
表1、新型铝体系偶联剂LD-429改性轻质碳酸钙在PVC微孔泡沫拖鞋中高填充制品性能测试结果＊
＊ 福建省中心检验所测试，试验在福建省永安市第一塑料厂进行
＊＊以100份树脂计。
表2、新型铝体系偶联剂LD-429改性轻质碳酸钙在改性PE交联发泡鞋底中高填充制品性能测试结果＊
＊ 试验和测试均在福州塑料橡胶厂进行
表3、新型铝体系偶联剂LD-429改性轻质碳酸钙在PVC微孔泡沫拖鞋鞋带中高填充制品性能测试结果＊
＊ 福建省中心检验所测试，试验在福建省永安市第一塑料厂进行。
Claims (18)
1、一种制备偶联剂的方法，其特征在于制备以铝为中心原子的铝体系偶联剂，包括以下步骤。
（1）、三烷氧基铝与低聚烷氧基铝的制备
（a）金属铝与1-10倍理论量的低级醇，必要时可添加金属铝重量0.01-1%的催化剂，在20～160℃下反应2-8小时后，常压下蒸出过量低级醇，然后减压蒸出三烷氧基铝，反应式为：
2Al+6ROH→2Al（OR）3+3H2↑……（A）
（b）将三烷氧基铝，或溶于适量惰性溶剂中，加热回流，逐渐通入三烷氧基铝重量0.001～8.8%的水蒸气，回流1～4小时，常压蒸出溶剂，加入微量酸或碱或氧化物等缩合剂，减压升温回流至160～200℃反应2～4小时，于减压下继续升温，将低聚烷氧基铝蒸出，反应式为：
Al（OR）3+H2O→Al（OR）2（OH）+ROH……（B）
（2）、交换与配位反应：
一克分子三（或低聚）烷氧基铝，加二克分子含羧基、羟基、酯基、醚键或酸酐的有机物（以F-B-H表示），必要时加1-3克分子配位体L和适量惰性溶剂，于40-160℃下回流0.5～4小时后，再蒸馏出低沸产物，获得铝体系偶联剂。反应式为：
2、按权利要求1所述的方法，其特征是金属铝须加工成反应接触面较大的各种形式。
3、按权利要求1和2所述的方法，其特征是用于活化处理各种形式的金属铝的催化剂为铜、汞、银、金的氯化物或醋酸盐，最适宜的是氯化汞或醋酸汞。
4、按权利要求1所述的方法，其特征是与金属铝反应的低级醇是甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、各种异构戊醇、各种异构己醇和苯酚，最适宜的是异丙醇、正丁醇或异丁醇。
5、按权利要求1所述的方法，其特征是反应式（E）中的是指三烷氧基铝、二至三聚烷氧基铝或其混合物。
6、按权利要求1所述的方法，其特征是配位体L系指含孤电子对原子的有机物，最适宜的是含氧或氮原子的有机物。
7、按权利要求1所述的方法，其特征是含羧基、羟基、酯基、醚键或酸酐的长链有机物是指含6～20或更多碳原子的，或具有支链或环状结构的单一或混合的脂肪醇、烷基取代烷、脂肪酸、磷酸酯、焦磷酸酯、焦亚磷酸酯、烷基磺酸、烷基硫酸酯基酸和酸酐。
8、按权利要求1和7所述的方法，其特征是含羧基、羟基、酯基醚键和酸酐的长链有机物的长链上还可含有能与聚合物分子链发生化学反应的官能团，最适宜的是双键、硫键、异氰酸基、偶氮基和叠氮基。
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85102942.6A CN1005265B (zh) | 1985-04-12 | 1985-04-12 | 新型铝体系偶联剂 |
| EP86104686A EP0198374A3 (en) | 1985-04-12 | 1986-04-05 | Coupling agent system of aluminium |
| US06/851,144 US4816594A (en) | 1985-04-12 | 1986-04-11 | Coupling agent system of aluminium |
| JP61083995A JPS6339883A (ja) | 1985-04-12 | 1986-04-11 | アルミネ−トカプリング剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85102942.6A CN1005265B (zh) | 1985-04-12 | 1985-04-12 | 新型铝体系偶联剂 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN85102942A CN85102942A (zh) | 1986-10-08 |
| CN1005265B true CN1005265B (zh) | 1989-09-27 |
Family
ID=4792875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN85102942.6A Expired CN1005265B (zh) | 1985-04-12 | 1985-04-12 | 新型铝体系偶联剂 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4816594A (zh) |
| EP (1) | EP0198374A3 (zh) |
| JP (1) | JPS6339883A (zh) |
| CN (1) | CN1005265B (zh) |
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| DE3726485A1 (de) * | 1987-08-08 | 1989-02-16 | Merck Patent Gmbh | Metallorganische verbindungen |
| US5084586A (en) * | 1990-02-12 | 1992-01-28 | Minnesota Mining And Manufacturing Company | Novel initiators for cationic polymerization |
| US6908665B2 (en) * | 1999-07-06 | 2005-06-21 | Northwest Coatings L.L.C. | Radiation-cured, laminated flexible packaging material |
| US7445797B2 (en) | 2005-03-14 | 2008-11-04 | Momentive Performance Materials Inc. | Enhanced boron nitride composition and polymer-based compositions made therewith |
| US6713088B2 (en) | 1999-08-31 | 2004-03-30 | General Electric Company | Low viscosity filler composition of boron nitride particles of spherical geometry and process |
| US7976941B2 (en) | 1999-08-31 | 2011-07-12 | Momentive Performance Materials Inc. | Boron nitride particles of spherical geometry and process for making thereof |
| US6753375B2 (en) * | 2001-07-02 | 2004-06-22 | The Goodyear Tire & Rubber Company | Process for preparing composite, composition and article thereof |
| US6989407B2 (en) | 2004-01-09 | 2006-01-24 | Northwest Coatings, Llc | Radiation curable laminating adhesives based on cycloaliphatic carboxylic acid functional monomers |
| US7524560B2 (en) | 2005-08-19 | 2009-04-28 | Momentive Performance Materials Inc. | Enhanced boron nitride composition and compositions made therewith |
| US7527859B2 (en) | 2006-10-08 | 2009-05-05 | Momentive Performance Materials Inc. | Enhanced boron nitride composition and compositions made therewith |
| US20090032162A1 (en) * | 2007-08-02 | 2009-02-05 | Xiao-Dong Pan | Belt assemblies and pneumatic tires including the same |
| DE102008031196A1 (de) * | 2008-07-03 | 2010-01-07 | Tesa Se | Hitze-aktivierbare Klebemassen zur Steigerung der Verbundfestigkeit zwischen Kunststoff und Metallen in Spritzgußbauteilen |
| US8415491B2 (en) | 2010-12-03 | 2013-04-09 | Southwest Research Institute | Surface treatment and exchange of nanostructures from aqueous suspension into organic media and into polymer-matrix composites |
| CN106588959B (zh) * | 2016-11-14 | 2019-04-19 | 江苏科技大学 | 一种含低聚烷氧基金属的偶联剂及其制备方法 |
| CN106591877A (zh) * | 2016-11-14 | 2017-04-26 | 江苏科技大学 | 一种中心原子可变换的偶联剂及其制备方法 |
| CN114516888A (zh) * | 2022-02-16 | 2022-05-20 | 山东键邦新材料股份有限公司 | 一种偶联剂的生产工艺方法及设备 |
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| US3042696A (en) * | 1956-07-20 | 1962-07-03 | Exxon Research Engineering Co | Preparation of aluminum alcoholates |
| GB840449A (en) * | 1956-09-13 | 1960-07-06 | Armour & Co | Improvements in and relating to the preparation of aluminium alcoholates |
| GB869951A (en) * | 1957-06-06 | 1961-06-07 | Du Pont | Werner type aluminium complexes, their preparation and use |
| US3070616A (en) * | 1960-03-31 | 1962-12-25 | Continental Oil Co | Oxidation of trialkylaluminum in the presence of aluminum trialkoxide |
| US3127432A (en) * | 1960-10-03 | 1964-03-31 | Monsanto Chemicals | Organic phosphorus-aluminum compounds and method of preparation |
| US3488370A (en) * | 1964-04-06 | 1970-01-06 | Gaf Corp | Organic polyoxyalkylene ether aluminates |
| US3538136A (en) * | 1967-02-02 | 1970-11-03 | Dow Chemical Co | Inorganic aluminum-oxygen-phosphorus bond polymers |
| US3686249A (en) * | 1970-04-24 | 1972-08-22 | Atlas Chem Ind | Method of preparing aluminum complexes of polyhydroxy compounds |
| JPS5022528B1 (zh) * | 1970-08-18 | 1975-07-31 | ||
| US3988333A (en) * | 1971-03-22 | 1976-10-26 | Teikoku Hormone Mfg. Co., Ltd. | Tri-substituted aluminum salts or di-substituted aluminum salts of carboxyl group-containing, pharmaceutically effective compounds |
| US4132724A (en) * | 1972-03-28 | 1979-01-02 | Manchem Limited | Preparation of organoaluminum compositions |
| GB1434191A (en) * | 1972-03-28 | 1976-05-05 | Hardman & Holden Ltd | Aluminium containing compounds and composites |
| ZA732070B (en) * | 1972-03-28 | 1973-12-19 | Hardman & Holden Ltd | Aluminium containing compounds |
| AU5942573A (en) * | 1972-08-25 | 1975-02-20 | Commw Scient Ind Res Org | Coating particulates |
| US3969387A (en) * | 1972-12-29 | 1976-07-13 | Merkl George | Metalic-organo-peroxide and organo-metalic-peroxide and preparation thereof |
| US3856841A (en) * | 1973-03-28 | 1974-12-24 | Merkl George | Aluminum organoiodides |
| JPS5839176B2 (ja) * | 1977-07-15 | 1983-08-27 | 住友化学工業株式会社 | 表面改質された有機物質用無機添加剤 |
| FR2420540A1 (fr) * | 1978-03-24 | 1979-10-19 | Philagro Sa | Procede de fabrication de monoethylphosphite d'aluminium |
| GB2048870A (en) * | 1979-04-30 | 1980-12-17 | Manchem Ltd | Aluminium complex method for its preparation and air-drying composition containing it |
| JPS56125475A (en) * | 1980-03-06 | 1981-10-01 | Kawaken Fine Chem Co Ltd | Surface modifier for powdered material having hydrophilic surface |
| US4283316A (en) * | 1980-09-12 | 1981-08-11 | Aluminum Company Of America | Surface modification of alumina hydrate with liquid fatty acids |
| JPS5796030A (en) * | 1980-12-08 | 1982-06-15 | Nippon Synthetic Chem Ind Co Ltd:The | Inorganic filler composition for polymer |
| JPS57195163A (en) * | 1981-05-27 | 1982-11-30 | Kawaken Fine Chem Co Ltd | Surface modifying agent for particulate and granular material having hydrophilic surface |
| JPS57200438A (en) * | 1981-06-03 | 1982-12-08 | Mitsubishi Rayon Co Ltd | Coating composition for polypropylene molded article |
| JPS57205431A (en) * | 1981-06-12 | 1982-12-16 | Kawaken Fine Chem Co Ltd | Surface modifier for particulate substance having hydrophilic surface |
| US4529555A (en) * | 1982-09-27 | 1985-07-16 | Kawaken Fine Chemicals Co., Ltd. | Surface modifier for powdery or granular substance having hydrophilic surface comprising an aluminum chelate compound |
| US4514555A (en) * | 1983-04-16 | 1985-04-30 | Idemitsu Kosan Company Limited | Process for the production of high molecular weight organoaluminum _polymers |
| US4525307A (en) * | 1983-08-02 | 1985-06-25 | Joseph Ayers, Inc. | Modified aluminum tri-alkoxide compounds |
| JPH0636573A (ja) * | 1992-07-22 | 1994-02-10 | Nec Corp | 半導体集積回路 |
-
1985
- 1985-04-12 CN CN85102942.6A patent/CN1005265B/zh not_active Expired
-
1986
- 1986-04-05 EP EP86104686A patent/EP0198374A3/en not_active Withdrawn
- 1986-04-11 US US06/851,144 patent/US4816594A/en not_active Expired - Fee Related
- 1986-04-11 JP JP61083995A patent/JPS6339883A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US4816594A (en) | 1989-03-28 |
| EP0198374A3 (en) | 1988-07-20 |
| JPS6339883A (ja) | 1988-02-20 |
| EP0198374A2 (en) | 1986-10-22 |
| CN85102942A (zh) | 1986-10-08 |
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