CN1069608C - 用于生产成品的层状蛭石的制备方法 - Google Patents
用于生产成品的层状蛭石的制备方法 Download PDFInfo
- Publication number
- CN1069608C CN1069608C CN95197150A CN95197150A CN1069608C CN 1069608 C CN1069608 C CN 1069608C CN 95197150 A CN95197150 A CN 95197150A CN 95197150 A CN95197150 A CN 95197150A CN 1069608 C CN1069608 C CN 1069608C
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- Prior art keywords
- resin
- vermiculite
- particle
- dry powder
- thermoplastic resin
- 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.)
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- 239000010455 vermiculite Substances 0.000 title claims description 126
- 229910052902 vermiculite Inorganic materials 0.000 title claims description 126
- 235000019354 vermiculite Nutrition 0.000 title claims description 126
- 238000000034 method Methods 0.000 title claims description 46
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 229920005989 resin Polymers 0.000 claims description 110
- 239000011347 resin Substances 0.000 claims description 110
- 239000008187 granular material Substances 0.000 claims description 75
- 239000002245 particle Substances 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 50
- 239000002904 solvent Substances 0.000 claims description 45
- 229920005992 thermoplastic resin Polymers 0.000 claims description 44
- 239000000843 powder Substances 0.000 claims description 39
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- 150000002148 esters Chemical class 0.000 claims description 22
- 230000005855 radiation Effects 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- -1 polyethylene Polymers 0.000 claims description 15
- 229920003986 novolac Polymers 0.000 claims description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
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- 150000008064 anhydrides Chemical class 0.000 claims description 6
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- 238000002360 preparation method Methods 0.000 claims description 5
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
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- OSQBFLZKVLCVGI-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carbonyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate Chemical compound C1CCC2=CC=CC=C2C1C(=O)OC(=O)C1C2=CC=CC=C2CCC1 OSQBFLZKVLCVGI-UHFFFAOYSA-N 0.000 claims description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- 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 claims description 3
- 239000002174 Styrene-butadiene Substances 0.000 claims description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003292 glue Substances 0.000 claims description 3
- 229920003225 polyurethane elastomer Polymers 0.000 claims description 3
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- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
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- 239000000835 fiber Substances 0.000 description 8
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
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- PGYPOBZJRVSMDS-UHFFFAOYSA-N loperamide hydrochloride Chemical group Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 PGYPOBZJRVSMDS-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000006424 Flood reaction Methods 0.000 description 2
- 229920002488 Hemicellulose Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
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- 238000001746 injection moulding Methods 0.000 description 2
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- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
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- 229920004449 Halon® Polymers 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 description 1
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
- B29C70/58—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising fillers only, e.g. particles, powder, beads, flakes, spheres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
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Abstract
一种用于生产成品如颗粒板的层状蛭石颗粒制备方法,其包括步骤:如必要,用一种在非水溶剂中的合适的酸酐浸渍蛭石而对蛭石化学改性,如必要给蛭石颗粒涂一种粘接促进剂以便促进树脂与蛭石颗粒表面的粘接;表面已用辐射或氟化改性的热塑树脂或异氰酸酯热固树脂,或酚醛清漆热固树脂干粉浸渍蛭石颗粒,如果必要并除去所存在的溶剂。
Description
发明背景
本发明涉及用于生产成品的层状蛭石颗粒的制备方法及由该层状蛭石颗粒制成成品的方法。
发明概要
本发明第一个方面是提供一种用于生产成品的层状蛭石颗粒的制备方法,该方法包括步骤:
(a)任意选择地,通过用一种浸渍组合物浸渍蛭石而对蛭石化学改性,该组合物包括溶解在非水溶剂中按浸渍组合物重量计为0.25%至20%的二羧酸酐或三羧酸酐;
(b)用下列过程之一对蛭石颗粒用树脂浸渍:
(ⅰ)给颗粒涂一种粘接促进剂从而促进树脂粘接到蛭石颗粒的表面上,然后给颗粒涂上按颗粒重量计为1%至50%的一种干粉形式的热塑树脂,以便该热塑树脂粘接到蛭石颗粒表面上,所述热塑树脂具有用辐射或氟化改性的表面;或
(ⅱ)在步骤(a)的浸渍组合物中包含有溶解在相容溶剂中的按浸渍组合物重量计的0.25%至50%的异氰酸酯热固树脂;或
(ⅲ)给颗粒涂一种粘接促进剂从而促进树脂粘接到蛭石颗粒的表面上,然后给颗粒涂一种干粉状的酚醛清漆热固树脂,以便酚醛清漆热固树脂干粉粘接在蛭石颗粒表面;以及
(c)在步骤(b)之后,除去所存在的溶剂。
在第一个选择方案中,该方法包括步骤:
(a)用一种浸渍组合物浸渍蛭石从而对蛭石化学改性,该浸渍组合物包括溶解在非水溶剂中的二羧酸酐或三羧酸酐;
(b)(ⅱ)通过在步骤(a)的浸渍组合物中包含一种溶解在相容溶剂中的异氰酸酯热固树脂从而用树脂浸渍蛭石颗粒;和
(c)在步骤(b)(ⅱ)之后除去溶剂。
在该情况下,不需要粘接促进剂。
二羧酸酐可选自马来酸酐、邻苯二甲酸酐、琥珀酸酐或四氢化邻苯二甲酸酐,而三羧酸酐可以是偏苯三酸酐。合适的溶剂包括乙酸甲酯、乙酸乙酯、甲乙酮、苯、三氯乙烯和二氯甲烷。优选二氯甲烷。
浸渍组合物优选地含有0.25%-20%,更优选0.25%-10%的酸酐(以浸渍组合物重量为基准)。
在除去溶剂之前,蛭石吸取优选为20%-250%,更优选为30%-150%的浸渍组合物时(以蛭石重量为基准),在除去溶剂后,蛭石中的酸酐数量为0.05%-50%,以蛭石重量为基准。
用于异氰酸酯树脂的溶剂优选地是与用于浸渍组合物的溶剂相同,但可以是不同的相容溶剂。
浸渍组合物优选地含有数量为0.25%-50%的异氰酸酯热固树脂(以浸渍组合物重量为基准)。
在第二个选择方案中,该方法包括步骤:
(b)(ⅰ)给颗粒涂一种粘接促进剂以便促进树脂粘接到蛭石颗粒的表面上,然后
给颗粒涂一种热塑树脂干粉,以便该热塑树脂粘接到蛭石颗粒表面上,热固树脂具有用辐射或氟化改性的表面;和
(c)在步骤(b)之后,除去任何存在的溶剂。
在该情况下,不再要求蛭石的化学改性。粘接促进剂可用或不用溶剂进行涂敷。
粘接促进剂优选地选自转化型树脂,如石油树脂、烃树脂和苯并呋喃茚树脂;热塑橡胶;苯乙烯丁二烯树脂;苯乙烯丙烯酸酯树脂;氯化橡胶;酚醛树脂;可溶热塑树脂;如聚苯乙烯或聚氯乙烯;木质纤维素衍生的胶或松香;溶胀纤维素,如甲基羟丙基纤维素;酚醛清漆树脂;聚氨酯弹性体;树脂增粘剂;沥青;煤焦油;(石油)沥青和木沥青;如果需要,它们溶解在合适的非水溶剂中,如那些在以上列出用于酸酐的溶剂。
在第二个选择方案中,粘接促进剂可在水相中应用,如选自于水溶、水分散或水混溶的聚合物的那些物质,它们在-15℃-40℃之间的温度下相对于电解质是稳定的并形成一薄膜,其包括聚乙烯醇、聚氨酯、烯烃、丙烯酸乙烯酯类、聚乙烯卤化物、氯丁二烯共聚物和丁苯橡胶分散液、丁二烯-乙酸乙烯酯共聚物和聚丙烯酸酯、丙烯酸和丙烯酸类压敏物。
涂在颗粒上的粘接促进剂量为0.1%-25%(以蛭石颗粒重量为基准)。
热塑树脂优选包括辐射后的交联热塑树脂干粉,优选为细分散干粉、该树脂干粉已经过γ辐射,树脂选自聚氯乙烯、线型低密度聚乙烯、低密度聚乙烯、高密度聚乙烯或热塑树脂干粉,优选为细分散干粉,其已进行了氟化,该树脂选自于聚氯乙烯、聚乙烯或聚丙烯。
在步骤(b)(ⅰ)中,用1%-500%的热塑树脂(以蛭石重量为基准)浸渍蛭石颗粒。当蛭石颗粒用于挤出或注模方法时,则随后优选地用50%-500%热塑树脂(以蛭石重量为基准)浸渍颗粒。然而,当颗粒用于压模成型方法时,例如生产颗粒板,则随后优选地用2%-50%的热塑树脂(以蛭石重量为基准)浸渍颗粒。
在第三个选择方案中,该方法包括步骤:
(b)(ⅲ)给颗粒涂一种粘接促进剂,该促进剂包含润湿蛭石颗粒并导致树脂粘接到蛭石颗粒的表面上的溶剂;然后
给颗粒涂一种酚醛清漆热固树脂干粉,以便酚醛清漆热固树脂干粉粘接到蛭石颗粒表面,并且
(c)在步骤(b)后,除去溶剂。
溶剂可选自水或二氯甲烷。
也可在蛭石颗粒中引入合适的增强纤维。
另外,蛭石颗粒可与合适数量的低温研磨后的橡胶碎颗粒混合,比如从汽车轮胎中回收到的橡胶颗粒,粒径为0.25-3mm,以便改善由其制成的成品的弹性、抗振性、可钉性、和韧性。
一种由层状蛭石颗粒制成制品的方法,该蛭石颗粒经过以上步骤(a)、(b)、(c)和(d)处理,该方法包括步骤:
(1)在合适的压力机或模具中,对蛭石颗粒加压同时加热以便使所存在的树脂聚合形成制品。
例如,可在合适的压力机或模具中,在120℃-250℃的温度下,以及在2-70kg/cm2的压力下,优选为130℃-220℃对蛭石颗粒加压并加热。
例如,制品可以是颗粒板。
一种由层状蛭石颗粒制成颗粒板的方法,该层状蛭石颗粒经过以上步骤(a)、(b)、(c)和(d)处理,该方法包括步骤:
(ⅰ)用一种组合物浸渍木质纤维材料板,该组合物包括热固树脂,热固树脂增量液,及热固树脂催化剂(如果需要)。
(ⅱ)回收增量液;
(ⅲ)在蛭石颗粒板的一侧或二侧装置浸渍后的木质纤维材料层从而形成复合体,以及
(ⅳ)在合适的压力机中对复合体加压同时加热从而使所存在的树脂聚合,并使在浸渍后的板材中的热固树脂聚合并胶结,从而整体凝固形成颗粒板。
还有,例如,可在合适的压力机中,在120℃-250℃之间,优选在130℃-200℃之间的温度下,及在2-70kg/cm2的压力下对复合体加压同时加热。
一种由层状蛭石颗粒制成制品的方法,该蛭石经过以上步骤(a)、(b)、(c)和(d)处理,该方法包括步骤:
(Ⅰ)对蛭石颗粒进行挤压或注模处理同时加热以便使所存在的树脂聚合形成制品。技术方案的描述
本发明第一个方面是一种制备用于生产成品的层状蛭石颗粒的方法。
蛭石是一种水合层状矿物的地质学名称,它是一种类似于白云母的铝、铁、镁硅酸盐,如云母或粘土,且当其受热时,由于内层产生气流的作用而剥离。该材料为惰性、化学纯、不致癌、不含石棉、不腐蚀、不燃、人体不过敏、无气味并人体摄入无害。它具有1315℃的熔点,和1260℃的烧结温度。它具有K=0.062-0.065w/m℃的热导率。它以颗粒形式使用,粒径为从通过200μm的筛子的量是98-100%(筛析),松密度为50-75克/升到90-130克/升。典型合适等级的蛭石是MDX,SFX,FNX或Micron(来自于Micronised Products Ltd,这是PalaboraMining Company,South Africa的子公司)。
在本发明第一个选择方案中,用一种浸渍组合物浸渍蛭石来对蛭石化学改性,该组合物包括二羧酸酐,如马来酸酐、邻苯二甲酸酐、琥珀酸酐或四氢化邻苯二甲酸酐,或三羧酸酐,如偏苯三酸酐,它们溶在合适的溶剂中。
溶剂的选择取决于其适用性,如毒性,处理的难易性,沸点和蒸发速率,它们依次影响从浸渍后的蛭石中回收溶剂的难易性,其惰性和无化学干扰性,可燃性和爆炸的危险性,用于浸渍液扩散和促进蛭石润湿的溶解能力用活性碳吸附接着蒸汽清洗和蒸馏,或冷凝和致冷或膜渗或筛分技术手段进行最终回收溶剂的难易性。合适的溶剂的实例是乙酸甲酯、乙酸乙酯、甲乙酮、苯、三氯乙烯,和二氯甲烷。二氯甲烷是优选的溶剂,因为它是不燃的,具有大约39℃的沸点并相对惰性,以及满足该方法的其它要求。另外,二氯甲烷具有吸收溶质水形成98%的共沸物并进一步扩散异氰酸酯潜在物的倾向,异氰酸酯与含羟基的化合物,大量水反应形成脲烷。二氯甲烷较高的蒸发率也促进了残余水更快地蒸发。
浸渍组合物包括溶解在合适相容溶剂中的异氰酸酯热固树脂。
异氰酸酯是含-N=C=O基的化合物并用通式:R(NCO)x表示,式中x是可变的并代表NCO基的数量而R代表预聚合物基。
这些异氰酸酯的实例是含有(NCO)百分含量优选超过20%,更优选超过30%的那些异氰酸酯。这些异氰酸酯促使潜伏或减少了反应活性并提供了羟基键合的最大能力。实例是Desmadur VKS或DesmadurVK(来自Bayer),它们是芳香族聚异氰酸酯,如二苯甲烷-4,4-二异氰酸酯和聚合物的无溶剂混合物,这些物质和类似物在工业上一般被称作MDIs。使用的另一种物质是二异氰酸根合二苯甲烷,又一实例是Suprasec DNR-5005,它是聚合物MDI,或Suprasec 2020,它是有效NCO百分含量为30.7%和29%的单体MDI,并且它们分别是具有标准官能度的聚合物MDI和单体MDI。Suprasec树脂由ICI提供。粗MDI的另一实例是Voronate M 229(由Dow Chemical Company提供)。
另一合适的二异氰酸酯是甲苯二异氰酸酯,其又一名称为亚苄基二异氰酸酯,或亚甲代苯基二异氰酸酯,缩写TDI,如Desmadur L75(来自Bayer)。
溶剂可以是任何适用的溶剂,并优选为二氯甲烷,将异氰酸酯热固树脂溶解在浓度为0.25-50%,更优选为1-10%(以浸渍组合物重量为基准)的二氯甲烷中。
蛭石是天然的铝硅酸盐,具有键合的铝硅酸盐四面体层,并与氢氧化镁或氢氧化铝层结合。粘土晶格中的羟基使异氰酸酯和酸酐交联,而金属氢氧化物的存在又催化了这种交联。例如,现已发现:密度为0.4,分别仅用2%和0.6%(以蛭石重量为基)的“Supersec 5005”(ICO)MDI和马来酸酐粘接的层状蛭石板具有显著的粘接强度。在给定的细层状蛭石表面区,这似乎是主要的粘接机理。
在用溶剂中的异氰酸酯热固树脂处理蛭石后,回收溶剂以便再利用。异氰酸酯热固树脂留在蛭石中在适当的加热和加压条件处于一种随时可以聚合的潜在条件下。
通过浸泡、或喷射,用浸渍组合物浸渍蛭石,接着回收溶剂以便再利用。
本发明方法第二个选择方案是给颗粒涂一种粘接促进剂以便促进热塑树脂与蛭石颗粒表面的粘接。
粘接促进剂可用或不用溶剂进行敷涂,并以任何合适的方式如喷射等进行敷涂。
粘接促进剂优选地选自可转变树脂,如石油树脂、烃树脂、和苯并呋喃茚树脂。例如,石油树脂可从裂解油C9不饱和单体中衍生得到。烃树脂可以是烷基化烃树脂或羟基改性的烃树脂;热塑橡胶,如KratonD1102CS(来自Shell);苯乙烯丁二烯树脂;苯乙烯丙烯酸酯树脂;氯化橡胶;酚醛树脂;可溶性热塑树脂,如聚苯乙烯或聚氯乙烯;木质纤维素衍生的胶或松香;溶胀纤维素,如甲基羟丙基纤维素,如Culminal MHPC 2000S(由Hercules Corporation提供);酚醛清漆树脂,如Plyophen 602N或Varcum 3337(由PRP ResinsDivison of Sentrachem Ltd提供);沥青,如硬沥青Mexphalte H80/90(来自Shell),煤焦油沥青和木沥青;聚氨酯弹性体;树脂增粘剂,如Oulutac 20GPR(来自Forchem OY)。
如果必要,将它们溶在以上列出的用于酸酐的合适非水溶剂中,优选为二氯甲烷。
给颗粒涂上数量为0.1-25%(以蛭石颗粒重量为基准)的粘接促进剂。
在涂了粘接促进剂之前或之后,给颗粒涂一种热塑树脂,优选为细分散干粉,以便在涂了粘接促进剂后,热塑树脂粘接在蛭石颗粒的表面上,热塑树脂具有用辐射或氟化改性的表面。
在涂粘接促进剂之前,热塑树脂可与蛭石干颗粒混合。然后当涂了粘接促进剂时,热塑树脂便粘接在蛭石颗粒的表面上。
另外,可以涂了粘接促进剂之后,将热塑树脂涂在蛭石颗粒上。
热塑树脂可以是辐射交联的热塑树脂干粉,优选为细分散干粉,该树脂干粉已进行了γ辐射,该树脂选自聚氯乙烯,线型低密度聚乙烯,低密度聚乙烯和高密度聚乙烯。
例如热塑树脂干粉可以是聚氯乙烯,或线型低密度聚乙烯,低密度聚乙烯或高密度聚乙烯,该树脂已以各种吸收剂量,典型为5-30kGy,优选为8-25kGy,并优选在氧气或氧化气氛中进行了γ辐射,以典型为1.38Gy/秒的剂量率进行辐射。需指出过量的剂量会导致聚合物降解。
在袋中预辐射树脂原料细颗粒的方法是实用的并是较廉价的。辐射还诱发了树脂化学结构的化学变化而导致树脂显著的物理变化,其中当在树脂转变前该辐射诱发了化学变化时,该变化改善了粘接强度,转变时的附着力,当将树脂用作蛭石复合体的胶结剂时,辐射对最终树脂的结构特征及其相关物理性能有显著影响,辐射诱使交联主要发生在树脂的非晶相中并导致最终热塑树脂晶体量的提高及诱发热固行为,尽管辐射的存在也诱发了反应基团的接枝。
在辐射后的热塑树脂干粉粘接到蛭石表面上后,可回收所用的溶剂以便再利用,或将之除去。这就给蛭石留下了用树脂浸渍过的表面,该表面是干燥的并在潜在条件下是有效的,以便随时可以加工成成品。
浸渍蛭石的树脂干粉含量为1%-500%(以重量计,取决于成品的最终应用),但对于模压成型方法,如蛭石板更通常地是2%-50%,而对于挤压或注模产品,含量则为50%-500%(以重量计)。
另外,这些辐射后的热塑树脂细分散干粉可与沥青和合适的增量剂,如碳酸盐、滑石、或高岭土一起研磨,并在生产板材期间在蛭石核芯的一个或两个外表面上叠铺作为干燥外部平面膜或预着色膜,以便提供装饰表面。
热塑树脂也可是热塑树脂干粉,优选为细分散干粉,其已氟化,树脂选自聚氯乙烯、聚乙烯,和聚丙烯。
用氟气处理树脂细分散粉末,或纵横比很高的树脂纤维,或树脂薄片,因为它是强氧化剂,所以可用不大于99%(体积)的另一气体稀释。在引入氟气前,树脂颗粒可先抽真空,氟气可用氮气、氧气或其它气体稀释,并加压。在充分接触后,可一次将氟气除去,并用真空除气以使在保留气体中氟气的含量减至0.1份/百万或更低。
热塑树脂选自聚氯乙烯、聚乙烯或聚丙烯,聚丙烯是优选的聚合物,其已氟化并粘接到蛭石表面上。
氟化诱使树脂化学结构发生化学变化而导致树脂产生物理变化,其中,当这种氟化是在树脂转变前诱使化学变化发生时,该变化改善了粘接强度和转变时的附着力。当将树脂用作蛭石复合体的胶结剂时,氟化对树脂结构特征及其相关物理性能有影响,其中可诱使它们使之具有热固行为,而不是纯热塑行为,尽管氟化也诱使反应基团接枝。
在氟化热塑树脂干粉、纤维,或薄片粘接到蛭石表面上后,可回收所用的溶剂以便再利用或将之除去。这就给蛭石留下用树脂浸渍后的表面,该表面是干燥的并在潜在条件下是有效的,因为只有使其达到必要的温度和压力条件才能完成氟化胶结剂树脂的活化,其如下所述。
浸渍蛭石的树脂含量为1%-500%(以重量计,取决于成品的最终应用)。但对于模压成型法,例如复合板,更通常的为2%-50%(以重量计),而对挤压和注模产品,则为50%-500%(以重量计)。
另外,可对这些氟化热塑树脂细分散干粉,薄片,或纤维,或膜预着色以便在板的生产期间在蛭石复合体核芯的一个或二个外表面上叠铺作为干燥外部平面膜或预着色膜,从而提供装饰表面。另外,可使用本身就是薄膜的外部层压膜,而仅对内层氟化。
作为又一个选择方案,粘接促进剂可在步骤(c)(ⅰ)之前涂在热塑树脂颗粒上。
浸渍树脂的颗粒用于将颗粒彼此胶结从而形成复合体,或挤压产品等。
本发明方法第三个选择方案是给颗粒涂一种为溶剂的粘接促进剂,以便促进酚醛清漆树脂干粉与蛭石颗粒表面的粘接。还可在酚醛清漆树脂干粉涂在蛭石颗粒上之前或之后敷涂粘接促进剂。
因此,在涂粘接促进剂之前酚醛清漆树脂可与蛭石干颗粒混合。然后,当涂了粘接促进剂时,酚醛清漆树脂涂接到蛭石颗粒表面上。
另外,可在涂了粘接促进剂后,将酚醛清漆树脂涂在蛭石颗粒上。
溶剂可选自水和二氯甲烷。
酚醛清漆树脂是以酚和甲醛为基础的树脂,以及这种树脂的任何变体或改性体,其中,酚和甲醛的摩尔比超过1∶1。酚醛清漆树脂可含有催化剂,其热分解产生甲醛,诱使聚合物缩合形成最小收缩的三维稳定网状结构,它是坚固和不溶的。采用细分散的树脂粉末并使之具有在催化剂,如六亚甲基四胺热分解后在大约100-130℃通常在110℃下开始流动的性能。合适的酚醛清漆树脂的实例是Schenectady Corporationof South Africa codes 6240或3174,或Plyophen 24-700,和Plyophen 602N或Varcum 3337 of PRP Resins Division ofSentrachem Ltd of South Africa。
在酚醛清漆热塑树脂干粉粘到蛭石表面上后,可溶的粘接促进剂可以回收再利用或将之除去。这就给蛭石留下用树脂浸渍过的表面,该表面是干燥的并处于潜在条件下,随时可以加工成成品。
另外,蛭石颗粒可与适量的低温研磨橡胶碎颗粒混合,如从汽车轮胎中回收的橡胶颗粒,粒径为0.25-3mm,以便改善由其制成的成品的弹性、抗震性、可钉性、韧性。
现以给出本发明实施例
实施例1
形成一种包括1%邻苯二甲酸酐和3%Suprasec 5005 MDI(来自ICI)的二氯甲烷溶液的浸渍混合物。
用浸渍混合物浸渍层状蛭石颗粒以使在导出液体后颗粒能吸收达到150%的浸渍混合物。
此后,回收溶剂,二氯甲烷以便再利用。
将处理后的颗粒置于压力机的两个面板之间并在约210℃的温度下用5分钟将其压成板从而形成密度为0.34g/cm2的颗粒板。
实施例2
形成一种包括10kg二氯甲烷,400g甲醇,40克Culminal MHPC2000S(来自Hercules Corporation)的浸渍混合物。浸渍混合物静置不少于40分钟以使纤维素膨胀。
用浸渍混合物浸渍层状蛭石颗粒并随后排出液体。
处理后的蛭石颗粒随后与12%(以重量计)线型低密度辐射过的粒径为300目的聚乙烯混合,该聚乙烯已以16kGy的吸收剂量进行了辐射,以便聚乙烯颗粒粘接到蛭石颗粒上。
随后,回收溶剂二氯甲烷以便再利用。
颗粒在压力机二个面板之间于约220℃下加压约6分钟形成密度为0.93克/cm3的板材。
实施例3
形成一种包括1%马来酸酐的二氯甲烷溶液的浸渍组合物。
用浸渍混合物喷射层状蛭石颗粒以便使其吸收浸渍混合物。
当蛭石颗粒还是润湿时,向蛭石颗粒中加入10%(以蛭石重量为基准)平均粒径为250目的Varcum 3337酚醛清漆树脂,并搅拌颗粒以便酚醛清漆树脂颗粒粘接到蛭石颗粒上。
此后,回收溶剂二氯甲烷以便再利用。
颗粒在压力机的二个面板之间于约190℃下加压约4分钟形成厚为12mm密度为0.6g/cm3的板材。
本发明第二个方面是由层状蛭石颗粒制成制品的方法,蛭石用以上步骤(a)、(b)、(c)和(d)进行处理,该方法包括在合适的压力机或模具中对蛭石颗粒加压并加热以使所存在的树脂聚合形成制品。
例如,蛭石颗粒可在合适的压力机中于120℃-250℃的温度,优选为150℃-220℃的温度下,及2-70kg/cm2,优选为约18-30kg/cm2的压力下加压并加热。
本发明第三个方面是上述但用于由层状蛭石颗粒形成颗粒板的方法,通过在颗粒板中引入用特殊组合物浸渍的一层或多层木质纤维材料板而对颗粒板改性。这样,将浸渍后的木质纤维材料板引入到颗粒板一边或两边的外部水平面上,由此提供应力表层复合层,其表面可涂一层处理剂。
木质纤维材料板可是纸板,优选为牛皮纸、纸浆板、木板、或任何其它合适的木质纤维材料板。
木质纤维材料板用一种组合物浸渍,该组合物包括热固树脂,用于热固树脂增量液和用于热固树脂催化剂(如必要)。
用于浸渍的合适组合物的实例已在南非专利90/2260(属于PlasconTechnologies(Proprietary)Limited)中公开并在下面更详细地陈述。
人们希望热固树脂具有延长了的适用期,即在树脂混合物中粘度没有发生明显变化的时间。人们希望适用期至少14-25周。通过合适地选择热固树脂、增量液,和存在的催化剂可达到该目的。热固树脂也可保持在低温下,例如在10℃以下以延长适用期。
增量液的另一重要作用是使浸渍入板中的树脂的重量改变,从而控制树脂粘度,而并不干扰聚合,其易于从浸渍后的材料中回收并易于处理而没有毒性,爆炸或起火的危害。
热固树脂可以是酚醛树脂(可溶苯酚-甲醛树脂)优选为液态酚醛树脂,其在室温或高温下可聚合。合适的酚醛树脂实例包括CelobondJ2027 L J2018 J20/1096 L和J20/1081 L(来自British PetroleumCompany Plc),它可用催化剂,如Phencar 10或更优选潜伏催化剂Phencat P.R.P 382(来自British Petroleum Plc)进行催化。酚糠树脂用六亚甲基四胺催化。或者也可选择酚醛和蜜胺甲醛或脲醛树脂的混合物。
用于酚醛树脂的合适增量液可以是树脂的溶剂或低粘度稀释剂,并可以是活性或非活性的。典型的实例包括水、Cl、C1-C4醇如甲醇、或乙醇、高级醇如糠醇、丙酮或甲乙酮,或它们的混合物。
另一种特别适用的热固树脂是MDI和TDI异氰酸酯,它们可在没有多元醇或普通交联成分的情况下使用,因为它们与木质纤维材料板中的纤维素或半纤维素中的羟基联结。这类合适的聚氨酯前体的实例是Desmodur VK或Desmodur VKS(来自Bayer)。
用于异氰酸酯的合适的增量液是卤化烃,如二氯甲烷或三氯乙烷,或乙酸乙酯,催化剂不是必需的。
可使用的另一类热固树脂是室温固化的液态丙烯酸和甲基丙烯酸酯,及甲基丙烯酸甲酯类,典型地用过氧化苯甲酰粉末催化。另一类是脲甲醛树脂,蜜胺甲醛树脂,可用酸或碱对之催化,其可用二醇类进行内部塑化。
组合物可包括其它组分,如抑制剂,加速剂或表面活性剂,阻燃剂或增塑剂。
有两种用于本发明的特别优选的组合物。这些组合物之所以优选是因为它们具有最佳适用期,它们向被浸渍的板材中提供了最佳的树脂浸渍量,也使得浸渍后的热固树脂易于聚合及增量液易于回收。
第一种优选的液态组合物包括酚醛树脂,30%-400%(以酚醛树脂重量为基准)的增量液和酚醛树脂的催化剂,增量液选自C1-C4醇,优选甲醇,其影响潜伏期,但可与另一种溶剂混合而增加蒸发率,催化剂例如是Phencat 10或潜在催化剂,如P.R.P382BY British PetroleumPlc等。
第二种优选的液体组合物是异氰酸酯,优选为MDI或TDI异氰酸酯,(其中不必加催化剂),20%-350%(以树脂重量为基准)的增量液,增量液选自二氯甲烷、三氯乙烯、乙酸乙酯、乙酸甲酯,或其它合适的增量液,优选为二氯甲烷和酸酐。用纸浆或纸或木板或其它天然纤维或木质纤维材料的纤维素和半纤维素分子中的羟基酯化甲基或乙基异氰酸酯,并使之自身形成脲烷聚合物结构,该结构对所处理材料的物理性能产生好的影响。
木质纤维材料板可以用任何合适形式的液体组合物浸渍。例如在合适的增压筒中通过真空/加压/真空的浸渍方式来浸泡或浸渍。随后,使浸渍后的板材通过该方法的下一步骤。
在本方法下一步骤中,通过蒸发和随后再冷凝,或吸收回收在浸渍板中存在的增量液以便再利用。
在本方法下一步骤中,将浸渍后的木质纤维材料板置于蛭石颗粒板的顶部,或底部或底和顶部上面形成复合体,然后在合适的压力和温度条件下,在压力机的两个面板之间对复合体加压,加压可以是连续的也可以是非连续的,当浸渍板中的热固树脂聚合时,蛭石中的树脂聚合并整体凝固形成颗粒板,该板外部浸渍层牢固地粘到复合体的核芯上。板一经加压并在必要的温度就使其自身得到粉末涂层。
在以上方法步骤(a)-(d)后,在合适的压力机或模具中对蛭石颗粒加热下加压,如此处理的层状蛭石颗粒可制成颗粒板或其它制品。已发现:在其在压力机或模具中加压之前,通过用天然乳胶或热塑橡胶或其它粘稠可溶化合物溶液润湿蛭石颗粒可进一步对蛭石颗粒处理,然后蒸发掉溶剂,在天然乳胶的情况下,溶剂可是水,也可是丙烯酸压敏粘接剂。
这种结果是不论沿外部平面方向,还是任意沿整个厚度方向,蛭石颗粒被热塑橡胶或其它粘稠化合物彼此粘接在一起从而形成柔韧的板材。如前所述该板可随后在合适的压力机或模具中加压和加热。
热塑橡胶可是以上所列任何一种,而溶剂可是任何合适的溶剂,如二氯甲烷。另外,也可使用水中的天然乳胶。
通过喷射可将热塑橡胶或其它粘稠化合物的溶液涂到蛭石颗粒上,随后在除去溶剂前或后可对颗粒施加合适的压力。
用此步骤制成的产品优点是该韧性板可放在具有一定形状的表面的压力机或模具中,例如皱纹或弯曲表面,而不会产生导致成品厚度过多变化的颗粒位移。在合适的压力和温度下加压该韧性板,其首先与压力机或模具的形状相一致,随后加压并发生不可逆粘接而形成合适形状的构件。最终构件是耐水的,具有良好的机械性能并保持稳定的形状,没有与毒气挥发有关的粘接剂,在成本是有利的。
本发明第四个方面是一种通过常规挤压或注模技术由层状蛭石颗粒形成制品的方法,该蛭石用以上步骤(a)、(b)、(c)和(d)处理。
在生产成品之前,处理后的蛭石颗粒也可与适量的木质纤维颗粒或增强纤维如玻璃纤维或合成有机纤维混合。
以上所公开的各种方法和用以上方法生产的产品具有下面提到的各种优点。
1)在对颗粒化学处理和树脂浸渍后,回收溶剂以便再利用,颗粒处于一种潜伏条件下,该条件允许在不同地点,不同时间下进行加压操作来制板。这就允许进行非连续生产,并导致将所生产的单位产品的投资成本减至最低的另一优点,以及带来较大的市场灵活性,即出售预先生产的板材或仅由用户加压成板的精选蛭石。
2)避免了涉及毒气挥发的粘接剂,遇水膨胀降至最低,带来对机械性能和表面整体性的良好影响。
3)整个复合体由于成分压制而成,这样使得技术要求,如外表面装饰,内部胶结剂的复合和百分含量,核芯成分的添加剂如纤维,或外层膜的选择,产品形状和成型方法有很宽的选择。
Claims (12)
1.一种用于生产成品的层状蛭石颗粒的制备方法,该方法包括步骤:
(a)任意选择地,用一种浸渍组合物浸渍蛭石来对蛭石化学改性,该浸渍组合物包括溶解在非水溶剂中的按浸渍组合物重量计的0.25%至20%的二羧酸酐或三羧酸酐;
(b)用下列过程之一对蛭石颗粒进行树脂浸渍:
(ⅰ)给颗粒涂一种粘接促进剂以便促进树脂粘结到蛭石颗粒表面,然后给颗粒涂上按颗粒重量计的1%至500%的一种热塑树脂干粉,以便热塑树脂粘接到蛭石颗粒表面上,热塑树脂具有用辐射或氟化改性的表面;或
(ⅱ)在步骤(a)的浸渍组合物中包括溶解在相容溶剂中的按浸渍组合物重量计的0.25%至50%的异氰酸酯热固树脂;或
(ⅲ)给颗粒涂一种粘接促进剂以便促进树脂粘结到蛭石颗粒表面,然后给颗粒涂一种酚醛清漆热固树脂干粉以便酚醛清漆热固树脂干粉粘接在蛭石颗粒表面;和
(c)在步骤(b)之后,除去存在的任何溶剂。
2.权利要求1的方法,其中包括步骤:
(a)用一种浸渍组合物浸渍蛭石以对蛭石化学改性,该浸渍组合物包括溶解在非水溶剂中的按浸渍组合物重量计的0.25%至20%的二羧酸酐或三羧酸酐;
(b)(ⅱ)用步骤(a)的浸渍组合物对蛭石颗粒进行树脂浸渍,该组合物包括溶解在相容溶剂中的按浸渍组合物重量计的0.25%至50%的异氰酸酯热固树脂;和
(c)在步骤(b)(ⅱ)之后,除去溶剂。
3.权利要求1或2的方法,其中酸酐选自马来酸酐、邻苯二甲酸酐、琥珀酸酐、四氢化邻苯二甲酸酐或三苯六甲酸酐。
4.权利要求3的方法,其中用于酸酐的溶剂选自乙酸甲酯、乙酸乙酯、甲乙酮、苯、三氯乙烯或二氯甲烷。
5.权利要求1或2的方法,其中,用于异氰酸酯热固树脂的溶剂与用于浸渍组合物的溶剂相同。
6.权利要求1的方法,其中所包括的步骤(b)是以下的步骤:
(b)ⅰ给颗粒涂上一种粘接促进剂以便促进树脂与蛭石颗粒表面的粘接,然后给颗粒涂上一种热塑树脂干粉,以便热塑树脂粘接到蛭石颗粒表面上,热固树脂具有用辐射或氟化改性的表面。
7.权利要求1或6的方法,其中粘接促进剂选自可转变的树脂、热塑橡胶、苯乙烯丁二烯树脂、苯乙烯丙烯酸酯树脂、氯化橡胶、酚醛树脂、可溶热塑树脂、木质纤维素衍生胶或松香、溶胀纤维素、酚醛清漆树脂、聚氨酯弹性体、树脂增粘剂、沥青、煤焦油、(石油)沥青或木沥青。
8.权利要求1或6的方法,其中将数量为0.1%-25%(以蛭石颗粒重量为基准)的粘接促进剂涂到颗粒上。
9.权利要求1或6的方法,其中热塑树脂包括干粉形式的辐射交联热塑树脂干粉,该树脂干粉已经过γ辐射,该树脂选自聚氯乙烯,线型低密度聚乙烯、低密度聚乙烯或高密度聚乙烯。
10.权利要求1或6的方法,其中热塑树脂包括已氟化的热塑树脂干粉,该树脂选自聚氯乙烯、聚乙烯或聚丙烯。
11.权利要求1的方法,其中所包括的步骤(b)是以下的步骤:
(b)(ⅲ)给颗粒涂一种粘接促进剂,该粘接促进剂包括润湿蛭石颗粒并导致树脂粘接到蛭石颗粒表面上的溶剂,然后给颗粒涂一种酚醛清漆热固树脂干粉,以便酚醛清漆热塑树脂干粉粘接到蛭石颗粒表面上。
12.权利要求11的方法,其中该粘接促进剂选自水或二氯甲烷。
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ZA95/6664 | 1995-08-10 | ||
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US4328146A (en) * | 1979-09-24 | 1982-05-04 | Robert Andy | Method for improving characteristics of polymethylpentene through addition of coated mica particles |
Also Published As
Publication number | Publication date |
---|---|
DE69509546T2 (de) | 2000-11-02 |
DE69508270T2 (de) | 1999-08-05 |
AU3751095A (en) | 1996-05-23 |
AU691676B2 (en) | 1998-05-21 |
DE69508270D1 (de) | 1999-04-15 |
DE69509546D1 (de) | 1999-06-10 |
US6451153B1 (en) | 2002-09-17 |
EP0789675A1 (en) | 1997-08-20 |
WO1996013468A1 (en) | 1996-05-09 |
AU3750995A (en) | 1996-05-23 |
CA2204117A1 (en) | 1996-05-09 |
CN1171769A (zh) | 1998-01-28 |
ATE179740T1 (de) | 1999-05-15 |
DE69508270T4 (de) | 2001-07-05 |
EP0789730B1 (en) | 1999-05-06 |
EP0789675B1 (en) | 1999-03-10 |
CA2204119A1 (en) | 1996-05-09 |
WO1996013551A1 (en) | 1996-05-09 |
ES2130664T3 (es) | 1999-07-01 |
EP0789730A1 (en) | 1997-08-20 |
AU690351B2 (en) | 1998-04-23 |
ES2128772T3 (es) | 1999-05-16 |
ATE177415T1 (de) | 1999-03-15 |
US5879600A (en) | 1999-03-09 |
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