TW505652B - Process for reducing the sulfane chain length of bis(silylorganyl)polysulfanes - Google Patents
Process for reducing the sulfane chain length of bis(silylorganyl)polysulfanes Download PDFInfo
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- TW505652B TW505652B TW087118798A TW87118798A TW505652B TW 505652 B TW505652 B TW 505652B TW 087118798 A TW087118798 A TW 087118798A TW 87118798 A TW87118798 A TW 87118798A TW 505652 B TW505652 B TW 505652B
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- 229910000057 polysulfane Inorganic materials 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 15
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- IKRMQEUTISXXQP-UHFFFAOYSA-N tetrasulfane Chemical compound SSSS IKRMQEUTISXXQP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 230000002079 cooperative effect Effects 0.000 claims description 4
- 238000006477 desulfuration reaction Methods 0.000 claims description 4
- 230000023556 desulfurization Effects 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 230000000875 corresponding effect Effects 0.000 claims description 3
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 3
- 238000004904 shortening Methods 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 150000008117 polysulfides Polymers 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 235000006708 antioxidants Nutrition 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- 229920001021 polysulfide Polymers 0.000 claims 1
- 239000005077 polysulfide Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- XSMURGJOAJVSKQ-UHFFFAOYSA-N 1-chloroethoxy-diethoxy-propylsilane Chemical compound CCC[Si](OCC)(OCC)OC(C)Cl XSMURGJOAJVSKQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 239000012758 reinforcing additive Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- KBMBVTRWEAAZEY-UHFFFAOYSA-N trisulfane Chemical compound SSS KBMBVTRWEAAZEY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0236—Polyarylenethioethers containing atoms other than carbon or sulfur in a linkage between arylene groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/14—Polysulfides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Silicon Polymers (AREA)
Description
經滴部中央標準局員工消費合作社印« 505652 π- 五、發明説明(1 ) 本發明係關於一種縮短雙(矽烷基有機基)多硫烷之 硫烷鏈長的方法,所用的方法是使這些化合物與硫化物和 鹵代烷基矽烷反應。 長久以來已經知道此類型的多硫烷( DE—PS 2255577),且廣泛地被用作爲含矽 石的橡膠硫化物(特別是輪胎部分)之強固用添加物。雙 (三乙氧基甲矽烷基丙基)四硫烷(Si 69,Degussa AG ) 特別被用於此應用上(請參考,Wolff, 129th Meeting of the Rubber Division, American Chemistry Society,April 8-11,1 986,NY )。 相關二硫烷的加工優點最近被述於許多出版品中。根 據E P - A— 0 7 3 2 3 6 2這些化合物應該以儘可能 純淨化合物的方式摻入橡膠組成物中( US — PS 5,580,919)或者以混合物形式摻 入(DS —〇S 1 9 7 0 246.1)。 但是,根據以前的技術,因爲锍基矽烷必須以二氧化 錳加以氧化,所以二硫烷是在非令人娛悅的條件下製得( EP — A 7 1 8 302)。 本發明的目的是要提出一種得到所欲產物且沒有這些 伴隨現象的方法。 本發明提出一種縮短雙(矽烷基有機基)多硫烷之硫 烷鏈長的方法,其特徵在於通式如下的有機矽化合物 Z-Alk-Sx-Alk-Z (I) 其中,Z代表下列基團 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297»f ) (讀先閲讀背面之注意事項再填寫本頁)
-4- 五、 發明説明(2
一 Si- R
R
R
\R
-Si -R
R · IT #中’ R1 代表具1至5個碳原子之直鏈或帶有支鏈的烷 ^ ’具5至8個碳原子的環烷基,苄基或苯基(其視情況 戶斤須地被甲基、乙基或氯所取代), R 2 代表具1至5個碳原子之直鏈或帶有支鏈的烷氧基, 具5至8個碳原子的環烷基,苯氧基或苄基,其中,R 1和 R 2相同或相異, A 1 k 代表具1至1 0個碳原子(特別是1至4個碳原 + )之二價飽和或單飽和直鏈或帶有支鏈的烴基或如下基 團 讀先閲讀背面之注意事項再填寫本頁 ------1L--L----- 訂— Γ -(CH2)n 鲁 (CH2)n, x 代表3至8的整數,特別是4至6, n 代表1至4, 與通式如下的無水硫化物反應 M e 2 S ( Π ) 其中,Me代表鹼金屬(特別是鈉)或鹼土金屬原子或鋅 或鋁,及通式如下的有機矽
Z — A 1 k — Y 其中,Z和A 1 k的意義如前述者,而
經濟部中央標準局員工消費合作社印製 Π ) 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) -5- 505652 經濟部中央標準局員工消費合作社印製 五、發明説明(3 ) Y 代表 c 1、B r, 其中,根據欲部分脫硫之多硫烷的所欲硫含量選擇多硫烷 和M e 2 S的莫耳比。 在一個特別的實施例中,X代表統計意義’通常不容 易製得相對應之純淨的多硫烷。 藉由適當地調整莫耳比,能夠製造出不同多硫烷之混 合物,其中,如根據US — PS 5,580,919使 用的二硫烷優勢物(DE —〇S 19702046)或 非常純淨的二硫烷。 通常,所選用的反應比例使得式(Π )化合物加至反 應混合物中的量(莫耳數)至少足以與由脫硫反應和添加 的N a 2 S之硫部分新形成的S y基團反應,而得到式(I )化合物,其中,藉脫硫反應而形成的硫烷鏈長中,y < X g 1。 此反應以於有機溶劑中進行爲佳,以於在試驗條件下 呈惰性的極性溶劑中進行爲佳。這樣的溶劑特別包括具1 至6個碳原子的脂族醇類、具2至1 2個碳原子的醚類、 醯胺類(如:二甲替甲醯胺、亞硕(如:二甲亞硕)。 此反應通常於5 0 °C至高至所用溶劑之迴餾溫度下進 行,視情況地於在此溫度建立的壓力下進行。 所得產物鏈長特別是S y,其中y = 2。 欲縮短硫烷鏈長,以使用四硫烷爲佳。 此特別用於可輕易取得的雙(三乙氧基甲矽氧基丙基 )四硫烷。由藉由將反應物四硫烷、M e 2 S和式(π )化 (誚先閱讀背面之注意事項馮填寫本頁) .#衣.
• Ji II ΙΜΊ · 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公t ) -6 - 經濟部中央標隼局員工消費合作社印製 505652 五、發明説明(4 ) 合物的莫耳比調整至1:0·4至0·6:0·9至 1 · 1,而由四硫烷製得相對應的三硫烷。 由四硫烷製造二硫烷所須比例爲1 : 1 · 8至2 · 2 ·· 2 · 5 至 3 · 5。 所使用之較佳的式(m )化合物係可形成對稱多硫烷 分子者。 實例 實例1 :將平均鏈長由4縮短至2 在有N 2保護用氣體的情況下,將於1 2 0毫升乙醇中 之67 · 4克(0 · 13莫耳)雙(3 —三乙氧基甲矽烷 基丙基)四硫烷和1 5 · 5克(0 · 2 4莫耳)硫化鈉引 至具迴餾冷凝管和磁攪拌器之5 0 0毫升容量的三頸瓶中 。於室溫下將108 · 7克(0 · 45莫耳)3 -氯一丙 基三乙氧基矽烷加至其中,此反應混合物維持於迴餾溫度 達2 · 5小時。冷卻至室溫後,濾出沉澱物,瀘渣以3 0 毫升乙醇淸洗三次,收集到的濾液在迴轉式蒸發器中於 1 00 °C蒸發至最終真空度爲40毫巴。得到153 . 1 克黃色液體,根據1 Η - NMR光譜分析,包含平均多硫院 鏈長爲2的多硫烷混合物。 產率:9 0 % 實例2 :將平均鏈長由4縮短至3 在有Ν 2保護用氣體的情況下,將於1 〇 〇毫升乙醇中 本紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ 297公t ) (翱先閱讀背面之注意事項再填寫本頁)
505652 一_— ___ h1 五、發明説明(5 ) 之1〇0克(0 · 19莫耳)雙(3 —三乙氧基甲矽烷基 丙基)四硫烷和7 · 8克(0 · 1莫耳)硫化鈉引至具迴 餾冷凝管(滴液冷凝轉)和磁攪拌器之5 0 0毫升容量的 三頸瓶中並迴餾1小時。將4 8 · 2克(0 · 2莫耳)3 一氯-丙基三乙氧基矽烷加至其中,此反應混合物再維持 於迴餾溫度達2 · 5小時。冷卻至室溫後,濾出沉澱物, 濾渣以3 0毫升乙醇淸洗三次,收集到的濾液在迴轉式蒸 發器中於1 1 0 °C蒸發至最終真空度爲4 0毫巴。得到 144·9克紅棕色液體,根據-NMR光譜分析,包 含平均多硫烷鏈長爲3的多硫烷混合物。 產率:9 8 % 讀先閱讀背面之注意事項再填寫本頁
訂
經濟部中央標準局員工消費合作社印聚 本紙張尺度適用中國國家標準(CNS ) A4規格(210X29?公釐) 505652
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一 σ> 1 ο r 0) > c o CL O) c 3 r 0> 爹 3 < ά Έ z |Massen-% | CM 对· s O) GO o o o CO o 〇 o δ 卜 GO s* § σ> o o* o o l〇 o o | 100,011 | Integral S I s 1 1 I I I I 72.0671 2 1 442,761 | 474,831 | 506.891 | 538,961 ! 571,03] ί 603,09] CO o ra s ΓΜ CO 5 in g s 〇) ra CM CO 〇· r> CO ΓΟ CO 899? IAl| |Delta (ppm) ΙΟ Γ\ί 卜 (N σ> ri r> s ΓΟ ΓΟ m r> ri CO ri 0) 〇> <5 1 ω ω 5 E Gesamtschwefel: | polysuif. Schwefel: j Chlor (gesamt): i FlOchtige Bestandteile: ] ― Ansatz: Ketteniange CO r〇 to V) VO if) If) ω 另 c\/ V) EtOPTES Ethanol I
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ir ζ:θμ 09 6Bg ID)unlrolt:IQ>>uejl-5sl>-oIQLID>unlrlq)Msnl<-lct:lsN Massen-% o ΓΟ f〇 g 5 1 1 1 in 厂 〇· o' 100,011 I I entspricht S3t6 bis S4t0 entspricht S3,7 bis S4.0 entspricht 4,1 Gew.-% Si 23C - 〇 5 l go (N σ" o" g ro σ> Si JC p 1 1 i I 1 1 I I I y iV '^a 132.9395 I 22.95+-0,9 11,1+-0,85 to o n V o CD H 5 442,76 474,83 68*905 538,96 571.03 603,09 GO 〇 s cm 1 50506,09 g· ro σ> Td to cd o 今 P19Z ΙΛΙ ~1 Oelta (ppm) in 1 CM· 卜1 CM* ri ^! ri uT r> icT Ί [mittlere Ketteniange: jGesamtschwefel: jpolysuif. Schwefel: |Chlor (gesamt): Φ I ·〇 Γ3 W 0) m ω σ> I ο <D σ> 25 0) 1 r>i if) r> CO ω I in CO in 〇l 另 CM EtOPTES Ethanol
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Claims (1)
- 505652 is8 (:8 r丨8 六、申請專利範圍 附件1 A : 第87 1 1 8798號專利申請案 中文申請專利範圍修 民 [曰修正 1 · 一種縮短雙(矽烷基有機基)多硫烷之硫烷鏈長 的方法,其特徵在於: 如下通式的有機矽化合物 Ζ - A 1 k - S X - A 1 k - Z ( I ) (其中,Z代表下列基團 ' R2 •Si-R" (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 R 其中 R 2 代表具1至5個碳原子之直鏈或分支的烷氧基, Aik 代表具1至1 0個碳原子之二價飽和直鏈或分支 的烴基 X 代表3至8的整數) 與如下通式的無水硫化物 M e 2 S ( Π ) (其中,Me代表鹼金屬或鹼土金屬原子或鋅或銨),及 如下通式的有機矽化合物 Z — A 1 k — Y (in ) 其中,Z和A 1 k的意義如前述者,而 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 505652 A8 B8 C8 D8 々、申請專利範圍 Y 代表C 1、B r )反應, (請先閱讀背面之注意事項再填寫本頁) 其中,根據欲部分脫硫之多硫烷與所要產物的所欲硫含量 選擇多硫烷和M e 2 S的莫耳比,該反應係於5 0 °C至所用 溶劑之迴流溫度的溫度下進行,而所得之經脫硫的多硫院 爲純物質,或者是與他種多硫烷之混合物形式。 2 ·如申請專利範圍第1項之方法,其中X代表4至 6之整數。 3 ·如申請專利範圍第1項之方法,其中M e代表鈉 〇 · 4 ·如申請專利範圍第1項之方法,其中式(π )化 合物加至反應溶液中的量(莫耳數)至少足以與由脫硫反 應和添加的N a 2 S之硫部分新形成的S y基團反應,而得 到式(I )化合物,其中,藉脫硫反應而形成的硫院鍵長 中,y < X g 1 〇 5 .如申請專利範圍第1至4項中任一項之方法,其 中使用醇類爲溶劑。 經濟部智慧財產局員工消費合作社印製 6 ·如申請專利範圍第1至4項中任一項之方法,其 中式(I )中的X和相對應的y相當於統計平均數。 了 ·如申請專利範圍第1至4項中任一項之方法,其 中對雙(矽烷基有機基)四硫烷進行脫硫處理。 8 ·如申請專利範圍第7項之方法,其中藉由將反應 物四硫烷、M e 2 S和式(m )化合物的莫耳比調整爲1 : 0 · 4至0 · 6 : 0 · 9至1 . 1,而由四硫烷製得三硫 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 505652 A8 B8 C8 D8 六、申請專利範圍 應:硫 反 1 二 將爲得 由整製. 藉調烷 中比硫 其耳四 ,莫由 法的而 方物 , 之合5 項化 · 7)3 第cmS 圍C 以車 利 專 請 申Μ . 如 、2 .烷至 9 硫 8 四 · 物 1 6 式 和 烷 (請先閱讀背面之注意事項再填寫本頁) 裝· 、11 經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中國國家標準(CNS ) Α4規格(210 X 297公釐) -3-
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE19750503A DE19750503A1 (de) | 1997-11-14 | 1997-11-14 | Verfahren zur Reduzierung der Sulfankettenlänge von Bis(silylorganyl)polysulfanen |
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TW087118798A TW505652B (en) | 1997-11-14 | 1998-11-11 | Process for reducing the sulfane chain length of bis(silylorganyl)polysulfanes |
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US (1) | US5965760A (zh) |
EP (1) | EP0937732B1 (zh) |
JP (1) | JPH11228582A (zh) |
KR (1) | KR19990045254A (zh) |
CN (1) | CN1218053A (zh) |
AT (1) | ATE238312T1 (zh) |
BR (1) | BR9804638A (zh) |
CA (1) | CA2254131A1 (zh) |
DE (2) | DE19750503A1 (zh) |
HU (1) | HUP9802649A3 (zh) |
ID (1) | ID21306A (zh) |
IL (1) | IL127046A (zh) |
PL (1) | PL329670A1 (zh) |
TW (1) | TW505652B (zh) |
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US6452034B2 (en) * | 2000-01-04 | 2002-09-17 | Crompton Corporation | Low-sulfur polysulfide silanes and process for preparation |
DE10034493C1 (de) * | 2000-07-15 | 2001-11-29 | Degussa | Verfahren zur Herstellung von Organosilylalkylpolysulfanen |
DE10045269A1 (de) * | 2000-09-13 | 2002-03-28 | Degussa | Verfahren zur Herstellung von gelbem Bis(3-[triethoxysilyl]propyl)polysulfan |
DE10132939C1 (de) * | 2001-07-06 | 2003-01-30 | Degussa | Verfahren zur Herstellung von gelben Bis(3-[trialkoxysilyl]alkyl)polysulfanen |
JP3975323B2 (ja) | 2001-07-25 | 2007-09-12 | 信越化学工業株式会社 | スルフィド鎖含有有機珪素化合物の製造方法 |
US6433206B1 (en) * | 2001-11-05 | 2002-08-13 | Crompton Corporation | Process for preparing silylorganomercaptans |
JP2003261580A (ja) * | 2002-03-08 | 2003-09-19 | Shin Etsu Chem Co Ltd | スルフィド鎖含有有機珪素化合物の製造方法 |
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DE19541404A1 (de) * | 1995-11-07 | 1997-05-15 | Degussa | Verfahren zur selektiven Synthese von Silylalkyldisulfiden |
JP3465558B2 (ja) * | 1997-09-26 | 2003-11-10 | 信越化学工業株式会社 | ポリスルフィドシランの製造方法 |
-
1997
- 1997-11-14 DE DE19750503A patent/DE19750503A1/de not_active Withdrawn
-
1998
- 1998-11-04 AT AT98120919T patent/ATE238312T1/de not_active IP Right Cessation
- 1998-11-04 EP EP98120919A patent/EP0937732B1/de not_active Expired - Lifetime
- 1998-11-04 DE DE59808060T patent/DE59808060D1/de not_active Expired - Fee Related
- 1998-11-11 JP JP10320702A patent/JPH11228582A/ja active Pending
- 1998-11-11 TW TW087118798A patent/TW505652B/zh not_active IP Right Cessation
- 1998-11-12 ID IDP981481A patent/ID21306A/id unknown
- 1998-11-12 PL PL98329670A patent/PL329670A1/xx unknown
- 1998-11-13 US US09/191,190 patent/US5965760A/en not_active Expired - Fee Related
- 1998-11-13 KR KR1019980048519A patent/KR19990045254A/ko not_active Application Discontinuation
- 1998-11-13 HU HU9802649A patent/HUP9802649A3/hu unknown
- 1998-11-13 CA CA002254131A patent/CA2254131A1/en not_active Abandoned
- 1998-11-13 CN CN98122313A patent/CN1218053A/zh active Pending
- 1998-11-13 BR BR9804638-1A patent/BR9804638A/pt not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
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IL127046A (en) | 2001-04-30 |
ATE238312T1 (de) | 2003-05-15 |
IL127046A0 (en) | 1999-09-22 |
BR9804638A (pt) | 1999-11-23 |
JPH11228582A (ja) | 1999-08-24 |
PL329670A1 (en) | 1999-05-24 |
CA2254131A1 (en) | 1999-05-14 |
EP0937732B1 (de) | 2003-04-23 |
HUP9802649A2 (hu) | 1999-09-28 |
CN1218053A (zh) | 1999-06-02 |
HU9802649D0 (en) | 1999-02-01 |
KR19990045254A (ko) | 1999-06-25 |
HUP9802649A3 (en) | 2002-05-28 |
US5965760A (en) | 1999-10-12 |
EP0937732A3 (de) | 2000-11-29 |
EP0937732A2 (de) | 1999-08-25 |
ID21306A (id) | 1999-05-20 |
DE59808060D1 (de) | 2003-05-28 |
DE19750503A1 (de) | 1999-05-20 |
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