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WO1999060047A1 - Polymeres de polysulfures et leur procede de preparation - Google Patents

Polymeres de polysulfures et leur procede de preparation Download PDF

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Publication number
WO1999060047A1
WO1999060047A1 PCT/JP1999/002581 JP9902581W WO9960047A1 WO 1999060047 A1 WO1999060047 A1 WO 1999060047A1 JP 9902581 W JP9902581 W JP 9902581W WO 9960047 A1 WO9960047 A1 WO 9960047A1
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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
general formula
polyoxyalkylene
polysulfide polymer
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.)
Ceased
Application number
PCT/JP1999/002581
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English (en)
Japanese (ja)
Inventor
Tatsuro Matsui
Kazuhisa Sakae
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Toray Thiokol Co Ltd
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Toray Thiokol Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Toray Thiokol Co Ltd filed Critical Toray Thiokol Co Ltd
Publication of WO1999060047A1 publication Critical patent/WO1999060047A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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

Definitions

  • the present invention relates to a polysulfide polymer which is liquid at ordinary temperature and has a mean sulfur number of repeating units of more than 2 and not more than 6 and a method for producing the same.
  • the present invention also relates to a polysulfide polymer suitable as a vulcanization accelerator, a vulcanizing agent and an extreme pressure agent, and a method for producing the same.
  • the polysulfide polymer is a liquid one in which the number of sulfur bonds in the repeating unit of the polysulfide polymer is 2, or a solid at room temperature in which the molecular weight exceeds 10 000 when the number of sulfur bonds in the repeating unit is 2 or more. Things are traded commercially. Polysulfide polymers that are liquid at room temperature and have more than two sulfur bonds in the repeating units are difficult to produce and there are no industrially effective ones. According to Japanese Patent Publication No. 63-42929, Japanese Patent Application Laid-Open (JP-A) No.
  • 63-42929 states that a polysulfide polymer which is liquid at room temperature and has a repeating unit sulfur bond number of more than 2 obtained by the reaction of sulfur chloride and dithiol is a rubber. It describes a method of using as a filler. In this method, it is necessary to use expensive dithiol as a raw material and to carry out the reaction in a large amount of anhydrous solvent, and the production cost is high industrially, which makes it difficult to use. In addition, the polysulfide polymer obtained by this method has a drawback that the terminal group is 1 SH and lacks storage stability.
  • An object of the present invention is to eliminate the above-mentioned conventional drawbacks and to provide a main chain having a repetition number of sulfur bonds exceeding disulfide, so that it can function only as a rubber flowing agent having a double bond. Instead, easily synthesize a polysulfide polymer having the required chemical structure, such as an alkyl group that increases the compatibility with mineral oil, such as a benzothiazol group or a thiocarbamyl group, which has a rubber vulcanization accelerating effect.
  • An object of the present invention is to provide a method and a novel specific polysulfide polymer which can be obtained by the method.
  • R 1 is an alkylene group having 2 to 10 carbon atoms, an oxyalkylene group having 2 to 10 carbon atoms, a polyoxyalkylene group having 2 to 20 oxygen atoms, and a hydroxyalkylene group having 3 to 12 carbon atoms. At least one group selected,
  • R 2 is an alkyl group having 1 to 20 carbon atoms, an ester thereof, a polyoxyalkylene group, a benzyl group, a resorcinol, a hydroxyalkyl group having 2 to 18 carbon atoms, a hydroxypolyoxyalkylene group, R 6 R 7 N (CS ) — (Where R 6 and R 7 are methyl, ethyl, butyl, or any alkyl or benzyl group of C 5 H.) thiocarbamyl, (CH 3 ) 2 CH ⁇ ( At least one group selected from the group consisting of a xanthate group showing a structure of CS), a benzothiazole group showing a structure of C 6 H 4 SNC—, and a morpholine group showing a structure of OC 4 H 8 N—,
  • X indicates a value from 2 to 6; and n represents an integer of 2 to 100.
  • R 1 is at least CH 2 CH 2 OCH 2 ⁇ CH 2 CH 2 or CH 2 CH 2 ⁇ CH 2 CH 2 OCH 2 CH 2 or CH 2 CH (OH) CH 2
  • R 2 is an alkyl group having 1 to 20 carbon atoms, an ester thereof, a polyoxyalkylene group, a benzyl group, a resorcinol, a hydroxyalkyl group having 2 to 18 carbon atoms, and a hydroxypolyoxy group.
  • the polysulfide polymer according to the above [1] which is a group selected from an allene group.
  • a general formula R 2 (S xR 1 ) n S xR 2 characterized by performing a sulfur exchange reaction between the general formula R 8 S (R'S y) nR'SR 8 and the general formula R 2 S yR 2
  • a method for producing a polysulfide polymer which is liquid at normal temperature
  • R ′ is selected from an alkylene group having 2 to 10 carbon atoms, an oxyalkylene group having 2 to 10 carbon atoms, a polyoxyalkylene group having 2 to 20 oxygen atoms, and a hydroxyalkylene group having 3 to 12 carbon atoms At least one group,
  • R 2 is an alkyl group having 1 to 20 carbon atoms, an ester thereof, a polyoxyalkylene group, a benzyl group, a resorsi hydroxyalkyl group having 2 to 18 carbon atoms, a hydroxypolyoxyalkylene group, R 6 R 7 N (CS) -(Where R 6 and R 7 are methyl, ethyl, butyl, CsH !, any alkyl group or benzyl group), thiol bamyl group, (CH 3 ) 2 CH ⁇ (CS) At least one group selected from a xanthate group having a structure of —, a benzothiazol group having a structure of C 6 H 4 SNC—, and a morpholine group having a structure of OC 4 H 8 N—
  • X indicates a value between 2 and 6
  • R 8 is R 2 S may be the same R 2 in the xR 2 well even different R 2,
  • y is a number greater than or equal to 2
  • n is an integer representing 2 to 100.
  • a compound represented by the general formula R 8 S (R'S y) nR'SR 8 and a compound represented by the general formula R 2 S.yR 2 are subjected to a sulfur exchange reaction in the presence of sulfur.
  • R ′ is an alkylene group having 2 to 10 carbon atoms, an oxyalkylene group having 2 to 10 carbon atoms, a polyoxyalkylene group having 2 to 20 oxygen atoms, and a hydroxyalkylene group having 3 to 12 carbon atoms. At least one group selected,
  • R 2 is an alkyl group having 1 to 20 carbon atoms, an ester thereof, a polyoxyalkylene group, a benzyl group, resorcinol, a hydroxyalkyl group having 2 to 18 carbon atoms, a hydroxy polyoxyalkylene group, R 6 R 7 N (CS) -(However, R 6 and R 7 are methyl, ethyl, butyl, CsH !.
  • any alkyl group or benzyl group any alkyl group or benzyl group), a rubamyl group, (CH 3 ) 2 CHO ( At least one group selected from the group consisting of a xanthogenic acid group having the structure of (CS) —, a benzothiazole group having the structure of C 6 H 4 S NC—, and a morpholine group having the structure of OC 4 H 8 N—. ,
  • X indicates a value between 2 and 6
  • R 8 ttR 2 S may be the same R 2 in the xR 2 well even different R 2,
  • y indicates a number greater than 1
  • n is an integer representing 2 to 100
  • [6] characterized by a sulfur exchange reaction and a polymerization reaction between a compound represented by the general formula HS (R'S y) nR 'SH and a compound represented by the general formula R 2 S yR 2 and sulfur
  • R 1 is selected from an alkylene group having 2 to 10 carbon atoms, an oxyalkylene group having 2 to 10 carbon atoms, a polyoxyalkylene group having 2 to 20 oxygen atoms, and a hydroxyalkylene group having 3 to 12 carbon atoms. At least one group
  • R 2 is an alkyl group having 1 to 20 carbon atoms, an ester thereof, a polyoxyalkyl group, a benzyl group, a hydroxyalkylene group having 2 to 18 carbon atoms, hydroxypolyoxy Alkylene group, R 6 R 7 N (CS)-(where R fi and R 7 are any alkyl groups of methyl group, ethyl group, butyl group and CsH), thiocarbamyl group showing the structure of (CH 3 ) 2 CHO (CS) At least one selected from a xanthate group showing a single structure, a benzothiazole group showing a C 6 H 4 SNC— structure, and a morpholine group showing a ⁇ C 4 H 8 N— structure Group,
  • X indicates a value between 2 and 6
  • y indicates a number greater than 1,
  • n an integer of 2 to L00.
  • R 1 is selected from an alkylene group having 2 to 10 carbon atoms, an oxyalkylene group having 2 to 10 carbon atoms, a polyoxyalkylene group having 2 to 20 oxygen atoms, and a hydroxyalkylene group having 3 to 12 carbon atoms At least one group,
  • R 2 is an alkyl group having 1 to 20 carbon atoms, an ester thereof, a polyoxyalkylene group, a benzyl group, a resorcinol, a hydroxyalkyl group having 2 to 18 carbon atoms, a hydroxypolyoxyalkylene group, R 6 R 7 N (CS )-(Where R s and R 7 are methyl, ethyl, butyl, CsH, any of alkyl or benzyl) thiocarbamyl, (CH 3 ) 2 CHO (CS) — At least one group selected from a xanthate group showing a structure, a benzothiazole group showing a structure of C 6 H 4 SNC—, and a morpholine group showing a structure of ⁇ C 4 H 8 N—,
  • X indicates a value between 2 and 6
  • y indicates a number greater than 1
  • n an integer of 2 to 100.
  • the most important feature of the present invention is to provide a novel and excellent method for producing polysulfide represented by the above-mentioned [4] to [7], which is suitable as a vulcanizing agent and a vulcanization accelerator.
  • the polysulfide polymer shown in [1] to [3] above is provided. It is in the point that we can offer.
  • the polysulfide polymer represented by the general formula HS (R 1 Sy) nR′SH used in the present invention is described in US Pat.No. 2,669,633 of Nodrick et al. And Japanese Patent Application Laid-Open No. 4-363325. Selected from such compounds. In this polysulfide polymer, the number of sulfur bonds y is usually two.
  • the polysulfide polymer represented by the general formula R 8 S (R 1 S y) nR'S R 8 is obtained by adding an oxygen atom such as ethylene oxide or propylene oxide to the compound represented by the general formula HS (R'S y) nR 'SH. It is easily obtained by adding a cyclic ether compound. Further, by reacting a compound represented by the general formula HS (R'Sy) n R 1 SH with an unsaturated group such as 2-hydroxyethyl acrylate or 2-hydroxyethyl methacrylate. Can also be easily obtained.
  • a glycidyl ether such as aryl, butyl, phenyl, methyl, 2-ethylhexyl, stearyl glycidyl ether, etc.
  • a polysulfide polymer having a terminal SH group can also be obtained by reacting an aldehyde or ketone with a terminal SH of a polysulfide polymer in the presence of an amine catalyst.
  • Examples of the compound represented by the formula R 2 S y R 2 include dimethyl disulfide, diphenyl disulfide, di-t-dodecyl polysulfide, di-t-nonyl polysulfide, di-t-butyl disulfide, resorcinol polysulfide, and bis (3-trimethoxysilylpropyl) polysulfide, bis (3-triethoxysilylpropyl) polysulfide, bis (3-trimethoxysilyltolylene) polysulfide, bis (3-triethoxysilyltolylene) polysulfide
  • Examples of the compound represented by the formula R 2 SH include mercaptosilanes such as amercaptopropyltrimethoxysilane and amercaptopropyltriethoxysilane, methyl mercaptan, ethyl mercaptan, propyl mercaptan, butyl mercaptan, and n Alkyl mercaptans such as octyl mercaptan, t-noyl mercaptan, dodecyl mercaptan, hexadodecyl mercaptan, noctadecyl mercaptan, 2-mercaptoethanol, 2-ethylhexyl thioglycolate, 3-mercapsipropion And mercaptans such as octyl acid, methoxybutyl monomercapsipropionate, and 2-mercaptobenzothiazole.
  • mercaptosilanes such as amer
  • an amine catalyst particularly triethylamine
  • the reaction temperature is preferably from 30 to 100 ° (:, the reaction time is from 10 minutes to 5 hours, and the amount of the catalyst is more preferably from 0.0 lwt% to 3 wt%.
  • R 2 S y R 2 to be added And Z or R 2 SH are preferably from 1 to 10 parts by weight of the raw material polysulfide polymer R 8 S (R'S y) n R 1 SR 8 and / or HS (R 'S y) n R' SH 100 parts by weight. 100 parts by weight, more preferably 2 to 500 parts by weight
  • the added sulfur is stoichiometric depending on the target x of the target polysulfide polymer R 2 SX (R ′ S x) nR 2. Can be decided.
  • R 2 is an alkyl group, polyoxyalkylene group, a hydroxyl group, a hydroxyalkyl group, if the hydroxy polyoxyalkylene group, It can be particularly suitably used for extreme pressure agents such as lubricating oil and cutting oil.
  • extreme pressure agents such as lubricating oil and cutting oil.
  • a surfactant is usually required, but a stable emulsion can be formed by selecting an appropriate.
  • the polysulfide polymer obtained by the production method of the present invention can also be used as a vulcanizing agent for rubber having a double bond, and is a polymer vulcanizing agent. It has good heat resistance and good stress relaxation, and can be expected to stabilize quality and improve quality by uniform dispersion of vulcanizing agent in rubber, rubber / rubber, and rubber Z resin.
  • rubbers having a double bond include natural rubber, butadiene rubber, styrene-butadiene rubber, isoprene rubber, butadiene-acrylonitrile rubber and / or its hydrogenated rubber, butyl rubber, halogenated butyl rubber, epichlorohydrin rubber, ethylene —Propylene-copolymer, ethylene-vinyl acetate copolymer, carboxy rubber, epoxide rubber, chloroprene rubber, acrylic rubber, millable urethane rubber and the like. These rubbers can be used not only for a single system but also for a blend system.
  • the use of the polysulfide polymer of the present invention in rubber having a double bond for dynamic crosslinking used as a thermoplastic elastomer does not preclude its use.
  • These applications include tire parts for automobiles, bicycles, trucks, buses, motorcycles, etc., various belts, various rollers, shoe materials, various hoses, seats, packing, vibration damping materials, seismic isolation materials, golf balls , Electric wire insulation • coating materials, cushioning elements, cables, gaskets, automobiles, home appliances, civil and architectural interior and exterior exterior materials and their parts.
  • the polysulfide polymer obtained in the present invention can be expected not only as a vulcanizing agent for the rubber itself by being compounded when producing a rubber or a thermoplastic elastomer, but also as an adhesive between glass and rubber, or between a glass and a thermoplastic elastomer. The effect can be expected.
  • R 2 is, R 5 R 6 N (CS ) - ( where, R 5, R 6 is methyl
  • a thiocarbamyl group having the structure of any of the following groups: an alkyl group, a benzyl group, an ethyl group, a butyl group, and a C 5 H group; a xanthate group having a structure of (CH 3 ) 2 CHO (CS) —
  • the polysulfide polymer obtained by the production method of the present invention is free of bloom, has good heat resistance and stress relaxation properties, and is obtained by uniform dispersion of a vulcanizing agent in rubber, rubber / rubber, and rubber Z resin. Can be expected to stabilize and improve quality.
  • Japan Rubber Chemical Industry Association has been taking measures against nitrosamines, and the emergence of polymer vulcanizing agents and polymer vulcanizing accelerators is expected (Akiha: Polymer Digest, 1999.11.11) , P21-29), the polysulfide polymer obtained by the present invention can meet this problem.
  • This substance had n of about 4 and a number average molecular weight of 1250. According to Raman analysis, the disulfide bonds of the starting polysulfide polymer were tri-, tetra-, and pen-bonds in this substance, and the average rank X was 4.
  • Example 1 It was examined whether the polysulfide polymer obtained in Example 1 had the effect of a vulcanizing agent and a vulcanization accelerator for rubber having a double bond.
  • the vulcanization characteristics at 150 ° C and 170 ° C were as follows, respectively.
  • Example 3 The test was conducted in the same manner as in Example 3 except that the amount of the polysulfide polymer of the present invention was reduced. 0.5 part of sulfur was added as a shortage of the vulcanizing agent.
  • the vulcanization characteristics at 150 ° C and 170 ° C were as follows. The results of Example 3 are also shown.
  • Example 2 It was examined whether the polysulfide polymer obtained in Example 2 had the effect of a vulcanizing agent and a vulcanization accelerator for a rubber having a heavy bond.
  • a rubber composition having the following composition was prepared at one outlet, and the vulcanization characteristics were examined (Curastome Ichiichi Type III Amplitude ⁇ 1 ° Frequency 100 cpm)
  • the vulcanization characteristics at 160 ° C. are as follows, and the polysulfide polymer of the present invention was sufficiently vulcanized even without a vulcanization accelerator or a vulcanizing agent.
  • This product has a viscosity at 118 ° C. of 18 boise at 25 ° C. and is a desired polysulfide polymer (structural formula: CH 3 — SX— (CH2CH2OCH2OCH2CH2-SX) 6 — CH 2 CH 2 OCH 2 ⁇ CH 2 CH 2 — S x — CH 3 ) was obtained.
  • This substance had n of about 6 and a number average molecular weight of 1520. According to the Raman analysis, the disulfide bonds of the raw polysulfide polymer were converted into tri-, tetra-, and pen-bonds with this substance, and the average rank X was 4.
  • Structural formula: HS— (CH 2 CH 2 OCH 2 ⁇ CH 2 CH 2 —S 2 ), 6 -CH 2 CH 2 CH 2 O CH2CH2 -SH) manufactured by Toray Recoal Co., SH content 2.3
  • the polysulfide polymer in which the number of sulfur bonds in the repeating unit of the present invention is more than 2 and not more than 6 is a rubber vulcanizing agent having an excellent double bond, It serves as a binder for the pressure agent, vulcanizing agent and vulcanization accelerator and rubber / silica filler.
  • the polysulfide polymer obtained by the production method of the present invention can also be used as a vulcanizing agent for a rubber having a double bond. It has good stress relaxation and can be expected to stabilize quality and improve quality by uniform dispersion of vulcanizing agent in rubber, rubber / rubber, and rubber / resin.
  • polysulfide polymer R 2 (S xR 1) n S xR 2 of the present invention R 2 Gaa alkyl group, polyoxyalkylene group, a hydroxyl group, a hydroxyalkyl group, if the hydroxy polyoxyalkylenated groups, the lubricant Particularly suitable for extreme pressure agents such as cutting oil. Can be used.
  • polysulfide polymer of the present invention can also be used for a rubber having a double bond for dynamic crosslinking used as a thermoplastic elastomer.
  • applications include tire parts for automobiles, bicycles, trucks, buses, motorcycles, etc., various belts, various mouthpieces, shoe materials, various hoses, seats, packing, vibration damping materials, seismic isolation materials.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé permettant de préparer facilement un polymère de polysulfures dont la chaîne principale contient des motifs répétés de polysulfures, supérieurs en nombre aux disulfures dans le nombre d'atomes de soufre constituants ce qui leur permet, par conséquent, de servir d'agent de vulcanisation pour les caoutchoucs à double liaison. Ledit polymère se termine par des groupes efficaces pour l'accélération de la vulcanisation des caoutchoucs, notamment des groupes benzothiazolyle ou thiocarbamyle, et des groupes alkyle efficaces quant à l'amélioration de la compatibilité avec les huiles minérales, ou autres structures chimiques requises. L'invention concerne également de nouveaux polymères de polysulfures spécifiques préparés selon le procédé de l'invention. Ces polymères de polysulfures, qui sont représentés par la formule générale (1): R2(SxR1)nSxR2 sont liquides à température ambiante.
PCT/JP1999/002581 1998-05-18 1999-05-18 Polymeres de polysulfures et leur procede de preparation Ceased WO1999060047A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP15359198A JP3978736B2 (ja) 1998-05-18 1998-05-18 ポリサルファイド重合体及びその製造方法
JP10/153591 1998-05-18

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2790262A1 (fr) * 1999-02-25 2000-09-01 Yokohama Rubber Co Ltd Composition de caoutchouc vulcanise pour bandage de pneumatique de poids lourd
US9079833B2 (en) 2011-04-12 2015-07-14 Shanghai Ici Research & Development & Management Co. Ltd. Process for the preparation of a polysulfide

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2311437A1 (fr) * 1999-08-17 2001-02-17 Marc Jules Alexis Henoumont Pneu dont l'element caoutchouc comporte un compose de polysulfide liquide
JP6843378B2 (ja) * 2016-10-17 2021-03-17 国立大学法人山口大学 含硫黄ポリマー
CN115477601A (zh) * 2022-09-22 2022-12-16 江苏麒祥高新材料有限公司 一种有机多硫化物及其制备方法和应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4119514B1 (fr) * 1963-08-16 1966-11-11
JPH047331A (ja) * 1990-04-25 1992-01-10 Toray Chiokoole Kk ポリサルファイドポリマー、その製造方法、及びその硬化型組成物
JPH04363325A (ja) * 1991-06-10 1992-12-16 Toray Chiokoole Kk 重合体組成物、その製造方法及びその硬化型組成物
JPH1067853A (ja) * 1996-05-14 1998-03-10 Nippon Shokubai Co Ltd エチレンスルフィド／硫黄共重合体の製造方法およびエチレンスルフィド／硫黄共重合体
JPH10120788A (ja) * 1996-10-21 1998-05-12 Toray Thiokol Co Ltd ポリサルファイド重合体

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4119514B1 (fr) * 1963-08-16 1966-11-11
JPH047331A (ja) * 1990-04-25 1992-01-10 Toray Chiokoole Kk ポリサルファイドポリマー、その製造方法、及びその硬化型組成物
JPH04363325A (ja) * 1991-06-10 1992-12-16 Toray Chiokoole Kk 重合体組成物、その製造方法及びその硬化型組成物
JPH1067853A (ja) * 1996-05-14 1998-03-10 Nippon Shokubai Co Ltd エチレンスルフィド／硫黄共重合体の製造方法およびエチレンスルフィド／硫黄共重合体
JPH10120788A (ja) * 1996-10-21 1998-05-12 Toray Thiokol Co Ltd ポリサルファイド重合体

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2790262A1 (fr) * 1999-02-25 2000-09-01 Yokohama Rubber Co Ltd Composition de caoutchouc vulcanise pour bandage de pneumatique de poids lourd
US6849674B2 (en) 1999-02-25 2005-02-01 The Yokohama Rubber Co., Ltd. Rubber composition
US6916888B2 (en) 1999-02-25 2005-07-12 The Yokohama Rubber Co., Ltd. Rubber composition
US9079833B2 (en) 2011-04-12 2015-07-14 Shanghai Ici Research & Development & Management Co. Ltd. Process for the preparation of a polysulfide

Also Published As

Publication number Publication date
JPH11322931A (ja) 1999-11-26
JP3978736B2 (ja) 2007-09-19

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