JPH04318043A - Clathrate compound of vulcanization accelerator - Google Patents
Clathrate compound of vulcanization acceleratorInfo
- Publication number
- JPH04318043A JPH04318043A JP8517291A JP8517291A JPH04318043A JP H04318043 A JPH04318043 A JP H04318043A JP 8517291 A JP8517291 A JP 8517291A JP 8517291 A JP8517291 A JP 8517291A JP H04318043 A JPH04318043 A JP H04318043A
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- vulcanization accelerator
- clathrate compound
- vulcanization
- diol
- 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.)
- Pending
Links
- 238000004073 vulcanization Methods 0.000 title claims abstract description 71
- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims abstract description 7
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims abstract description 7
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004380 Cholic acid Substances 0.000 claims abstract description 5
- 229960002471 cholic acid Drugs 0.000 claims abstract description 5
- 235000019416 cholic acid Nutrition 0.000 claims abstract description 5
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 claims description 8
- WXTPRAZNOXQAFY-UHFFFAOYSA-N 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C#CC#CC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 WXTPRAZNOXQAFY-UHFFFAOYSA-N 0.000 claims description 7
- CJETXAUUVYDHTN-UHFFFAOYSA-N 1,6-bis(2-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol Chemical compound C=1C=CC=CC=1C(C=1C(=CC=CC=1)Cl)(O)C#CC#CC(O)(C=1C(=CC=CC=1)Cl)C1=CC=CC=C1 CJETXAUUVYDHTN-UHFFFAOYSA-N 0.000 claims description 6
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims description 5
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 claims description 4
- MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 claims description 4
- CPXHDGJIYPGMMZ-UHFFFAOYSA-N 1,1,4,4-tetraphenylbut-2-yne-1,4-diol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C#CC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 CPXHDGJIYPGMMZ-UHFFFAOYSA-N 0.000 claims description 4
- YDMVFEUUJCFXNW-UHFFFAOYSA-N 1,1,6,6-tetrakis(2,4-dimethylphenyl)hexa-2,4-diyne-1,6-diol Chemical compound CC1=CC(C)=CC=C1C(O)(C=1C(=CC(C)=CC=1)C)C#CC#CC(O)(C=1C(=CC(C)=CC=1)C)C1=CC=C(C)C=C1C YDMVFEUUJCFXNW-UHFFFAOYSA-N 0.000 claims description 4
- GLQWGVMBEKNKTP-UHFFFAOYSA-N 1,1-bis(2,4-dimethylphenyl)prop-2-yn-1-ol Chemical compound CC1=CC(C)=CC=C1C(O)(C#C)C1=CC=C(C)C=C1C GLQWGVMBEKNKTP-UHFFFAOYSA-N 0.000 claims description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 4
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 claims description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 4
- RYFIDGIWTNANMO-UHFFFAOYSA-N 9,10-diphenylanthracene-9,10-diol Chemical compound C12=CC=CC=C2C(O)(C=2C=CC=CC=2)C2=CC=CC=C2C1(O)C1=CC=CC=C1 RYFIDGIWTNANMO-UHFFFAOYSA-N 0.000 claims description 4
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 4
- KDENVQZUIOWUSY-UHFFFAOYSA-N n,n-dicyclohexyl-2-[2-(dicyclohexylcarbamoyl)phenyl]benzamide Chemical compound C=1C=CC=C(C=2C(=CC=CC=2)C(=O)N(C2CCCCC2)C2CCCCC2)C=1C(=O)N(C1CCCCC1)C1CCCCC1 KDENVQZUIOWUSY-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- OSEHBGZOVPNBNK-UHFFFAOYSA-N 9,10-bis(4-methylphenyl)anthracene-9,10-diol Chemical compound C1=CC(C)=CC=C1C1(O)C2=CC=CC=C2C(O)(C=2C=CC(C)=CC=2)C2=CC=CC=C21 OSEHBGZOVPNBNK-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960003964 deoxycholic acid Drugs 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 abstract description 39
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 238000003860 storage Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000007965 phenolic acids Chemical class 0.000 abstract 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 14
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 13
- 239000004312 hexamethylene tetramine Substances 0.000 description 13
- 238000004898 kneading Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 229920001084 poly(chloroprene) Polymers 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 229960004337 hydroquinone Drugs 0.000 description 3
- -1 softeners Substances 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- GSFSVEDCYBDIGW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-6-chlorophenol Chemical compound OC1=C(Cl)C=CC=C1C1=NC2=CC=CC=C2S1 GSFSVEDCYBDIGW-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WFNXYMSIAASORV-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)cyclohexyl]phenol Chemical compound OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)CCCCC1 WFNXYMSIAASORV-UHFFFAOYSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- ULHIDKVNBFIQKP-UHFFFAOYSA-N butanal;butan-1-amine Chemical compound CCCCN.CCCC=O ULHIDKVNBFIQKP-UHFFFAOYSA-N 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- LEOJDCQCOZOLTQ-UHFFFAOYSA-N dibutylcarbamothioyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SC(=S)N(CCCC)CCCC LEOJDCQCOZOLTQ-UHFFFAOYSA-N 0.000 description 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 229950004394 ditiocarb Drugs 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010077 mastication Methods 0.000 description 1
- 230000018984 mastication Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010063 rubber manufacturing process Methods 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は加硫促進剤包接化合物に
係り、特に、加硫促進剤を包接することにより、ゴムと
の反応温度の適正化を図り、ゴム製造工程における歩留
り及び生産効率の向上を可能とする加硫促進剤包接化合
物に関する。[Industrial Application Field] The present invention relates to a vulcanization accelerator clathrate compound, and in particular, by including a vulcanization accelerator, it is possible to optimize the reaction temperature with rubber, thereby improving yield and production in the rubber manufacturing process. This invention relates to a vulcanization accelerator clathrate compound that enables improved efficiency.
【０００２】0002
【従来の技術】クロロプレンゴム等のゴムを加工してゴ
ム製品を製造する場合、まず、原料の秤量を行なった後
、原料ゴムを混合機に装入して素練りを行ない、更に、
充填剤、軟化剤、酸化亜鉛、硫黄及び加硫促進剤を添加
、混練りして成形用混合物を製造する。そして、この成
形用混合物を用いて成形品、押出品、ゴム引布等の各種
ゴム製品を製造する。[Prior Art] When manufacturing rubber products by processing rubber such as chloroprene rubber, first, the raw materials are weighed, and then the raw rubber is charged into a mixer and masticated.
Fillers, softeners, zinc oxide, sulfur and vulcanization accelerators are added and kneaded to produce a molding mixture. This molding mixture is then used to manufacture various rubber products such as molded products, extruded products, and rubberized cloth.
【０００３】上記ゴム製品の製造工程で使用される加硫
促進剤は、所定の加硫温度にて、ゴムの炭化水素分子間
を橋架けして３次元網目構造を形成させることにより、
成形性を付与するものである。従って、混練り工程にお
いてはゴムと反応することなく均一に混合され、かつ、
加硫成形時において効率的にゴムと反応することが要求
される。The vulcanization accelerator used in the manufacturing process of the above-mentioned rubber products bridges the hydrocarbon molecules of rubber to form a three-dimensional network structure at a predetermined vulcanization temperature.
It imparts moldability. Therefore, in the kneading process, it is uniformly mixed without reacting with the rubber, and
It is required to react efficiently with rubber during vulcanization molding.
【０００４】しかしながら、ゴムの素練り及び混練りは
加熱下で行なわれ、混合機内温度が高くなるため、混練
り工程において加硫促進剤がゴムと反応することにより
成形不能となる、いわゆるスコーチが発生する。そこで
、従来においては、混練り後１晩混合機内で冷却し、翌
日加工する方法が採用されている。However, mastication and kneading of rubber are carried out under heating, and the temperature inside the mixer becomes high, so the vulcanization accelerator reacts with the rubber during the kneading process, resulting in so-called scorch, which makes molding impossible. Occur. Therefore, in the past, a method has been adopted in which the mixture is cooled in a mixer overnight after kneading and processed the next day.
【０００５】また、加硫促進剤は、加硫成形効率の面か
ら、適正範囲内でできるだけ多く配合するのが有利であ
るが、加硫促進剤の高濃度配合はスコーチの原因となる
ため、配合濃度を高くすることができないという問題も
ある。[0005] In addition, from the viewpoint of vulcanization molding efficiency, it is advantageous to blend as much of the vulcanization accelerator as possible within an appropriate range, but since blending the vulcanization accelerator in a high concentration may cause scorch. There is also the problem that the concentration cannot be increased.
【０００６】このような問題を解決するために、加硫促
進剤をゲスト化合物とし、ハイドロキノン系ホスト化合
物等により包接化合物としたものを用いることが提案さ
れている（特開昭６２−８９７５３号）。In order to solve these problems, it has been proposed to use a vulcanization accelerator as a guest compound and a clathrate compound with a hydroquinone host compound or the like (Japanese Patent Application Laid-open No. 89753/1983). ).
【０００７】[0007]
【発明が解決しようとする課題】特開昭６２−８９７５
３号の方法によれば、ある程度の改善効果が得られるが
、特開昭６２−８９７５３号に開示されるようなハイド
ロキノン系ホスト化合物で包接化合物としたものは、そ
のものの保管中及びこれを用いたゴム製品中で、経時的
に白色から黄色に変色する。このため、ゴム製品の品質
に悪影響を及ぼすという欠点を有する。[Problem to be solved by the invention] JP-A-62-8975
According to method No. 3, a certain degree of improvement effect can be obtained, but when the clathrate compound is made of a hydroquinone-based host compound as disclosed in JP-A No. 62-89753, the clathrate compound may be damaged during storage and In the rubber product used, the color changes from white to yellow over time. For this reason, it has the disadvantage of adversely affecting the quality of rubber products.
【０００８】本発明は上記従来の問題点を解決し、ゴム
の混練り工程において反応することがなく、加硫成形工
程において効率的に反応することによりスコーチを防止
してゴム製品の製造における生産効率及び歩留りを大幅
に向上させることができる加硫促進剤包接化合物であっ
て、経時により変色することもない加硫促進剤包接化合
物を提供することを目的とする。The present invention solves the above conventional problems and prevents scorch by not reacting in the rubber kneading process and reacting efficiently in the vulcanization molding process, thereby improving production in the production of rubber products. It is an object of the present invention to provide a vulcanization accelerator clathrate compound which can significantly improve efficiency and yield and which does not change color over time.
【０００９】[0009]
【課題を解決するための手段】本発明の加硫促進剤包接
化合物は、加硫促進剤と、下記（１）〜（１９）のアル
コール系、フェノール系、環状アミン系及びコール酸系
多分子ホスト化合物から選ばれる１種又は２種以上のホ
スト化合物とからなることを特徴とする。
（１） １，１，６，６−テトラフェニル−２，４−
ヘキサジイン−１，６−ジオール
（２） １，６−ビス（２−クロロフェニル）−１，
６−ジフェニルヘキサ−２，４−ジイン−１，６−ジオ
ール
（３） １，１−ビス（２，４−ジメチルフェニル）
−２−プロピン−１−オール
（４） １，１，４，４−テトラフェニル−２−ブチ
ン−１，４−ジオール
（５） １，１，２，２−テトラフェニルエタン−１
，２−ジオール
（６） １，１−ビ−２−ナフトール（７） ９，
１０−ジフェニル−９，１０−ジヒドロアントラセン−
９，１０−ジオール
（８） １，１，６，６−テトラキス（２，４−ジメ
チルフェニル）−２，４−ヘキサジイン−１，６−ジオ
ール
（９） ９，１０−ビス（４−メチルフェニル）−９
，１０−ジヒドロアントラセン−９，１０−ジオール（
１０） ４，４’−シクロヘキシリデンビスフェノー
ル
（１１） Ｎ，Ｎ，Ｎ’，Ｎ’−テトラキス（シクロ
ヘキシル）−（１，１’−ビフェニル）−２，２’−ジ
カルボキシアミド
（１２） ４，４’−スルホニルビスフェノール（１
３） ４，４’−ブチリデンビス（３−メチル−６−
ｔｅｒｔ−ブチルフェノール）
（１４） ２，２’−メチレンビス（４−メチル−６
−ｔｅｒｔ−ブチルフェノール）
（１５） ４，４’−チオビス（３−メチル−６−ｔ
ｅｒｔ−ブチルフェノール）
（１６） ２，２’−メチレンビス（４−クロロフェ
ノール）
（１７） デオキシコール酸
（１８） コール酸
（１９） α，α，α’，α’−テトラフェニル−１
’，１’−ビフェニル−２，２’−ジメタノール以下に
本発明を詳細に説明する。本発明の加硫促進剤包接化合
物において、ゲスト化合物として、上記ホスト化合物に
包接される加硫促進剤としては特に制限はないが、例え
ば次の■〜■の加硫促進剤包接化合物が挙げられる。
■ グアニジン系
ジフェニルグアニジン，ジオルトトリルグアニジン■
アルデヒド−アミン系
ｎ−ブチルアルデヒド−アミン縮合品，ブチルアルデヒ
ド−モノブチルアミン縮合品
■ アルデヒド−アンモニア系
ヘキサメチレンテトラミン
■ チアゾール系
２−メルカプトベンゾチアゾール，ジベンゾチアジルジ
スルフィド
■ スルフィンアミド系
Ｎ−シクロヘキシル−２−ベンゾチアジルスルフィンア
ミド
■ チオ尿素系
エチレンチオ尿素，ジエチルチオ尿素
■ チウラム系
テトラメチルチウラムモノスルフィド，テトラブチルチ
ウラムモノスルフィド
■ ジチオカルバメート系
ジメチルジチオカルバミン酸ナトリウム，ジエチルジチ
オカルバミン酸ナトリウム
■ キサントゲネート系
イソプロピルキサントゲン酸ナトリウムこれらのうち、
特に、ヘキサメチレンテトラミンはクロロプレンの加硫
促進剤としてのみならず、ＳＢＲ、天然ゴム等の加硫促
進剤としても極めて有用であり、本発明に好適である。
なお、ヘキサメチレンテトラミンは合成樹脂の硬化剤と
しても使用されることから、本発明の加硫促進剤包接化
合物を、この用途に用いても良いことは言うまでもない
。[Means for Solving the Problems] The vulcanization accelerator clathrate compound of the present invention comprises a vulcanization accelerator and the following alcohol-based, phenol-based, cyclic amine-based, and cholic acid-based compounds. It is characterized by comprising one or more host compounds selected from molecular host compounds. (1) 1,1,6,6-tetraphenyl-2,4-
Hexadiyne-1,6-diol (2) 1,6-bis(2-chlorophenyl)-1,
6-diphenylhexa-2,4-diyne-1,6-diol (3) 1,1-bis(2,4-dimethylphenyl)
-2-propyn-1-ol (4) 1,1,4,4-tetraphenyl-2-butyne-1,4-diol (5) 1,1,2,2-tetraphenylethane-1
,2-diol (6) 1,1-bi-2-naphthol (7) 9,
10-diphenyl-9,10-dihydroanthracene-
9,10-diol (8) 1,1,6,6-tetrakis(2,4-dimethylphenyl)-2,4-hexadiyne-1,6-diol (9) 9,10-bis(4-methylphenyl )-9
, 10-dihydroanthracene-9,10-diol (
10) 4,4'-Cyclohexylidenebisphenol (11) N,N,N',N'-tetrakis(cyclohexyl)-(1,1'-biphenyl)-2,2'-dicarboxamide (12) 4 ,4'-sulfonylbisphenol (1
3) 4,4'-butylidene bis(3-methyl-6-
tert-butylphenol) (14) 2,2'-methylenebis(4-methyl-6
-tert-butylphenol) (15) 4,4'-thiobis(3-methyl-6-t
ert-butylphenol) (16) 2,2'-methylenebis(4-chlorophenol) (17) Deoxycholic acid (18) Cholic acid (19) α,α,α',α'-tetraphenyl-1
',1'-Biphenyl-2,2'-dimethanol The present invention will be explained in detail below. In the vulcanization accelerator clathrate compound of the present invention, the vulcanization accelerator to be included in the host compound as a guest compound is not particularly limited, but for example, the following vulcanization accelerator clathrate compounds can be mentioned. ■ Guanidine-based diphenylguanidine, diorthotolylguanidine ■
Aldehyde-amine type n-butyraldehyde-amine condensation product, butyraldehyde-monobutylamine condensation product ■ Aldehyde-ammonia type hexamethylenetetramine ■ Thiazole type 2-mercaptobenzothiazole, dibenzothiazyl disulfide ■ Sulfinamide type N-cyclohexyl-2 -Benzothiazyl sulfinamide ■ Thiourea-based ethylene thiourea, diethylthiourea ■ Thiuram-based tetramethylthiuram monosulfide, tetrabutylthiuram monosulfide ■ Dithiocarbamate-based sodium dimethyldithiocarbamate, sodium diethyldithiocarbamate ■ Xanthogenate-based isopropyl xanthogenic acid Of these, sodium
In particular, hexamethylenetetramine is extremely useful not only as a vulcanization accelerator for chloroprene, but also as a vulcanization accelerator for SBR, natural rubber, etc., and is suitable for the present invention. Note that since hexamethylenetetramine is also used as a curing agent for synthetic resins, it goes without saying that the vulcanization accelerator clathrate compound of the present invention may be used for this purpose.
【００１０】このような加硫促進剤をゲスト化合物とし
て包接化合物を形成するホスト化合物は、前記（１）〜
（１９）から選ばれる１種又は２種以上の多分子系ホス
ト化合物であるが、本発明においては、前記（１）〜（
１９）の多分子系ホスト化合物のうち、特に、２，２’
−メチレンビス（４−クロロフェノール）、４，４’−
シクロヘキシリデンビスフェノール、４，４’−スルホ
ニルビスフェノール等のフェノール系ホスト化合物を用
いるのが好ましい。[0010] The host compound that forms an clathrate compound using such a vulcanization accelerator as a guest compound is one of the above-mentioned (1) to
One or more types of multimolecular host compounds selected from (19) are selected from (1) to (1) in the present invention.
19) Among the multimolecular host compounds, especially 2,2'
-methylenebis(4-chlorophenol), 4,4'-
It is preferable to use phenolic host compounds such as cyclohexylidene bisphenol and 4,4'-sulfonyl bisphenol.
【００１１】本発明の加硫促進剤包接化合物は、例えば
、加硫促進剤を溶解させた溶液に、所定割合の多分子系
ホスト化合物を添加して反応させることにより、容易に
製造することができ、常法に従って、ゴムの加硫促進剤
として使用することができる。The vulcanization accelerator clathrate compound of the present invention can be easily produced, for example, by adding a predetermined proportion of a polymolecular host compound to a solution in which a vulcanization accelerator is dissolved and reacting the mixture. It can be used as a rubber vulcanization accelerator according to conventional methods.
【００１２】なお、本発明の加硫促進剤包接化合物を適
用し得るゴムの種類としては特に制限はなく、クロロプ
レンゴム、ＳＢＲ、天然ゴム、その他各種のゴム素材に
有効に使用することができる。[0012] There is no particular restriction on the type of rubber to which the vulcanization accelerator clathrate compound of the present invention can be applied, and it can be effectively used for chloroprene rubber, SBR, natural rubber, and various other rubber materials. .
【００１３】[0013]
【作用】本発明の加硫促進剤包接化合物において、ゲス
ト化合物である加硫促進剤は、特定の多分子系ホスト化
合物で包接されることにより化学的に安定化され、ゴム
の混練工程における温度（通常は１００℃以下）におい
てゴムと反応することが防止される。[Function] In the vulcanization accelerator clathrate compound of the present invention, the vulcanization accelerator, which is a guest compound, is chemically stabilized by being clathrated with a specific multimolecular host compound, and the vulcanization accelerator is chemically stabilized during the rubber kneading process. (usually below 100°C).
【００１４】一方、加硫温度（通常は１４０〜１８０℃
）においては、本発明の加硫促進剤包接化合物から加硫
促進剤が効率的に放出され、加硫促進剤がゴムと円滑に
反応して高い加硫効率が得られる。この加硫促進剤の放
出現象は、本発明の加硫促進剤包接化合物の融点が通常
のゴムの加硫温度である１４０〜１８０℃の範囲内にあ
るために起こるものと推定される。On the other hand, the vulcanization temperature (usually 140 to 180°C
), the vulcanization accelerator is efficiently released from the vulcanization accelerator clathrate compound of the present invention, and the vulcanization accelerator reacts smoothly with the rubber, resulting in high vulcanization efficiency. It is presumed that this phenomenon of release of the vulcanization accelerator occurs because the melting point of the vulcanization accelerator clathrate compound of the present invention is within the range of 140 to 180°C, which is the vulcanization temperature of ordinary rubber.
【００１５】[0015]
【実施例】以下に実施例及び比較例を挙げて本発明をよ
り具体的に説明するが、本発明はその要旨を超えない限
り、以下の実施例に限定されるものではない。[Examples] The present invention will be explained in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples unless it exceeds the gist thereof.
【００１６】実施例１
ヘキサメチレンテトラミン１ｇを１０ｍｌのメタノール
中に溶解し、得られた溶液に２，２’−メチレンビス（
４−クロロフェノール）をヘキサメチレンテトラミンと
等モルとなるように添加した。これを一晩放置し、メタ
ノールを蒸発させたところ、粉末結晶が得られた。この
結晶をＩＲ（赤外吸収スペクトル）で測定したところ、
ヘキサメチレンテトラミンをゲスト化合物とし、２，２
’−メチレンビス（４−クロロフェノール）をホスト化
合物とする包接化合物であることを確認した。包接化合
物中のヘキサメチレンテトラミン含有率は３３．６重量
％であった。Example 1 1 g of hexamethylenetetramine was dissolved in 10 ml of methanol, and 2,2'-methylenebis(
4-chlorophenol) was added in equimolar amounts with hexamethylenetetramine. When this was left overnight and methanol was evaporated, powder crystals were obtained. When this crystal was measured by IR (infrared absorption spectrum),
Hexamethylenetetramine is used as a guest compound, 2,2
It was confirmed that it is an inclusion compound containing '-methylenebis(4-chlorophenol) as a host compound. The content of hexamethylenetetramine in the clathrate compound was 33.6% by weight.
【００１７】次に、クロロプレン１００重量部に対して
ＭｇＯ５重量部、Ｚｎ５重量部、加硫促進剤として上記
加硫促進剤包接化合物１重量部を添加して、ゴムの混練
り、加硫成形を行なった。その結果、ゴムの混練り工程
において、ヘキサメチレンテトラミンは反応せず、温度
１４０℃の加硫工程において、クロロプレンゴムと効率
的に反応し、加硫が起こることが確認された。Next, to 100 parts by weight of chloroprene, 5 parts by weight of MgO, 5 parts by weight of Zn, and 1 part by weight of the above-mentioned vulcanization accelerator clathrate compound as a vulcanization accelerator were added, and rubber was kneaded and vulcanized. I did this. As a result, it was confirmed that hexamethylenetetramine did not react in the rubber kneading process, but reacted efficiently with chloroprene rubber in the vulcanization process at a temperature of 140°C, resulting in vulcanization.
【００１８】比較例１
加硫促進剤包接化合物の代りに、ヘキサメチレンテトラ
ミン０．３３重量部を用いたこと以外は、実施例１と同
様にしてクロロプレンゴムの混練り、加硫成形を行なっ
た。その結果、温度８０℃のゴムの混練り工程において
、一部加硫が進行し、成形不良品となった。Comparative Example 1 Chloroprene rubber was kneaded and vulcanized in the same manner as in Example 1, except that 0.33 parts by weight of hexamethylenetetramine was used instead of the vulcanization accelerator clathrate compound. Ta. As a result, vulcanization partially progressed during the rubber kneading process at a temperature of 80° C., resulting in a molded product.
【００１９】実施例２，３
２，２’−メチレンビス（４−クロロフェノール）の代
りに、４，４’−シクロヘキシリデンビスフェノール（
実施例２）又は４，４’−スルホニルビスフェノール（
実施例３）を用いたこと以外は実施例１と同様にして加
硫促進剤包接化合物を製造した。得られた包接化合物は
、いずれもヘキサメチレンテトラミンをゲスト化合物と
するものであって、その含有量は、それぞれ、３１．９
重量％（実施例２）、３７．６重量％（実施例３）であ
った。Examples 2 and 3 Instead of 2,2'-methylenebis(4-chlorophenol), 4,4'-cyclohexylidenebisphenol (
Example 2) or 4,4'-sulfonylbisphenol (
A vulcanization accelerator clathrate compound was produced in the same manner as in Example 1 except that Example 3) was used. The resulting clathrate compounds all have hexamethylenetetramine as a guest compound, and their content is 31.9%.
% by weight (Example 2), and 37.6% by weight (Example 3).
【００２０】次に得られた加硫促進剤包接化合物を用い
て、各々、実施例１と同様にしてクロロプレンゴムの混
練り、加硫成形を行なった。その結果、いずれの場合も
、ゴムの混練り工程において、ヘキサメチレンテトラミ
ンは反応せず、加硫工程においてクロロプレンゴムと効
率的に反応し、加硫が起こることが確認された。Next, using the obtained vulcanization accelerator clathrate compounds, chloroprene rubber was kneaded and vulcanized in the same manner as in Example 1. As a result, it was confirmed that in all cases, hexamethylenetetramine did not react in the rubber kneading process, but reacted efficiently with chloroprene rubber in the vulcanization process, resulting in vulcanization.
【００２１】比較例２，３
２，２’−メチレンビス（４−クロロフェノール）の代
りに、２−ｔｅｒｔ−ブチル−１，４−ベンゼンジオー
ル（比較例２）又は２，５−ジ−ｔｅｒｔ−ブチル−１
，４−ベンゼンジオール（比較例３）を用いたこと以外
は実施例１と同様にして加硫促進剤包接化合物を製造し
た。得られた包接化合物は、いずれもヘキサメチレンテ
トラミンをゲスト化合物とするものであって、その含有
量は、それぞれ３５．５重量％（比較例２）、３５．８
重量％（比較例３）であった。Comparative Examples 2 and 3 Instead of 2,2'-methylenebis(4-chlorophenol), 2-tert-butyl-1,4-benzenediol (Comparative Example 2) or 2,5-di-tert- Butyl-1
A vulcanization accelerator clathrate compound was produced in the same manner as in Example 1 except that , 4-benzenediol (Comparative Example 3) was used. The resulting clathrate compounds all contain hexamethylenetetramine as a guest compound, and their contents are 35.5% by weight (Comparative Example 2) and 35.8% by weight, respectively.
% by weight (Comparative Example 3).
【００２２】次に得られた加硫促進剤包接化合物を用い
て、実施例１と同様にしてクロロプレンゴムの混練り、
加硫成形を行なったところ、ゴムの混練り工程において
、ヘキサメチレンテトラミンは反応せず、加硫工程にお
いてクロロプレンゴムと効率的に反応し、加硫が起こる
ことが確認された。Next, using the obtained vulcanization accelerator clathrate compound, chloroprene rubber was kneaded in the same manner as in Example 1.
When vulcanization molding was performed, it was confirmed that hexamethylenetetramine did not react during the rubber kneading process, but reacted efficiently with chloroprene rubber during the vulcanization process, resulting in vulcanization.
【００２３】しかしながら、これらのハイドロキノン系
ホスト化合物を用いた包接化合物は、保管中及びゴム製
品中において、経時的に白色から黄色に変色し、このた
め、製品品質に悪影響を及ぼすことが確認された。[0023] However, it has been confirmed that clathrate compounds using these hydroquinone-based host compounds change color from white to yellow over time during storage and in rubber products, which has an adverse effect on product quality. Ta.
【００２４】[0024]
【発明の効果】以上詳述した通り、本発明の加硫促進剤
包接化合物は、ゴムの混練り工程においては加硫反応を
生起することなく、加硫工程において、ゴムと円滑に反
応して加硫を起こすことから、本発明の加硫促進剤包接
化合物によれば、スコーチを引き起こすことなく、ゴム
製品の成形を行なうことが可能とされる。このため、ス
コーチ防止のために、ゴムの混練り後、加硫工程に到る
前に冷却処理を施す必要がなくなり、混練り後、直ちに
加硫工程に移行することができ、生産効率は大幅に向上
する。また、加硫促進剤の高濃度添加も可能とされ、加
硫時間の短縮、加硫効率の向上が図れる。[Effects of the Invention] As detailed above, the vulcanization accelerator clathrate compound of the present invention smoothly reacts with rubber in the vulcanization process without causing a vulcanization reaction in the rubber kneading process. Since the vulcanization accelerator clathrate compound of the present invention causes vulcanization, it is possible to mold rubber products without causing scorch. This eliminates the need for cooling treatment after kneading the rubber and before the vulcanization process to prevent scorch, and allows the vulcanization process to proceed immediately after kneading, greatly increasing production efficiency. improve. Furthermore, it is possible to add a vulcanization accelerator at a high concentration, thereby shortening the vulcanization time and improving the vulcanization efficiency.
【００２５】しかも本発明の加硫促進剤包接化合物は、
保管中、或いは、ゴム製品中において、経時により変色
することもなく、製品品質を高く維持することができる
。従って、本発明の加硫促進剤包接化合物によれば、高
品質のゴム製品を、高い歩留りにて、かつ、高い生産効
率にて製造することが可能とされる。Moreover, the vulcanization accelerator clathrate compound of the present invention is
During storage or in rubber products, the product quality can be maintained at a high level without discoloring over time. Therefore, according to the vulcanization accelerator clathrate compound of the present invention, it is possible to produce high quality rubber products with high yield and high production efficiency.
Claims (1)
のアルコール系、フェノール系及びコール酸系多分子ホ
スト化合物から選ばれる１種又は２種以上のホスト化合
物との加硫促進剤包接化合物。 （１） １，１，６，６−テトラフェニル−２，４−
ヘキサジイン−１，６−ジオール （２） １，６−ビス（２−クロロフェニル）−１，
６−ジフェニルヘキサ−２，４−ジイン−１，６−ジオ
ール （３） １，１−ビス（２，４−ジメチルフェニル）
−２−プロピン−１−オール （４） １，１，４，４−テトラフェニル−２−ブチ
ン−１，４−ジオール （５） １，１，２，２−テトラフェニルエタン−１
，２−ジオール （６） １，１−ビ−２−ナフトール（７） ９，
１０−ジフェニル−９，１０−ジヒドロアントラセン−
９，１０−ジオール （８） １，１，６，６−テトラキス（２，４−ジメ
チルフェニル）−２，４−ヘキサジイン−１，６−ジオ
ール （９） ９，１０−ビス（４−メチルフェニル）−９
，１０−ジヒドロアントラセン−９，１０−ジオール（
１０） ４，４’−シクロヘキシリデンビスフェノー
ル （１１） Ｎ，Ｎ，Ｎ’，Ｎ’−テトラキス（シクロ
ヘキシル）−（１，１’−ビフェニル）−２，２’−ジ
カルボキシアミド （１２） ４，４’−スルホニルビスフェノール（１
３） ４，４’−ブチリデンビス（３−メチル−６−
ｔｅｒｔ−ブチルフェノール） （１４） ２，２’−メチレンビス（４−メチル−６
−ｔｅｒｔ−ブチルフェノール） （１５） ４，４’−チオビス（３−メチル−６−ｔ
ｅｒｔ−ブチルフェノール） （１６） ２，２’−メチレンビス（４−クロロフェ
ノール） （１７） デオキシコール酸 （１８） コール酸 （１９） α，α，α’，α’−テトラフェニル−１
’，１’−ビフェニル−２，２’−ジメタノール[Claim 1] A vulcanization accelerator and the following (1) to (19)
A vulcanization accelerator clathrate compound with one or more host compounds selected from alcohol-based, phenolic-based, and cholic acid-based multimolecular host compounds. (1) 1,1,6,6-tetraphenyl-2,4-
Hexadiyne-1,6-diol (2) 1,6-bis(2-chlorophenyl)-1,
6-diphenylhexa-2,4-diyne-1,6-diol (3) 1,1-bis(2,4-dimethylphenyl)
-2-propyn-1-ol (4) 1,1,4,4-tetraphenyl-2-butyne-1,4-diol (5) 1,1,2,2-tetraphenylethane-1
,2-diol (6) 1,1-bi-2-naphthol (7) 9,
10-diphenyl-9,10-dihydroanthracene-
9,10-diol (8) 1,1,6,6-tetrakis(2,4-dimethylphenyl)-2,4-hexadiyne-1,6-diol (9) 9,10-bis(4-methylphenyl )-9
, 10-dihydroanthracene-9,10-diol (
10) 4,4'-Cyclohexylidenebisphenol (11) N,N,N',N'-tetrakis(cyclohexyl)-(1,1'-biphenyl)-2,2'-dicarboxamide (12) 4 ,4'-sulfonylbisphenol (1
3) 4,4'-butylidene bis(3-methyl-6-
tert-butylphenol) (14) 2,2'-methylenebis(4-methyl-6
-tert-butylphenol) (15) 4,4'-thiobis(3-methyl-6-t
ert-butylphenol) (16) 2,2'-methylenebis(4-chlorophenol) (17) Deoxycholic acid (18) Cholic acid (19) α,α,α',α'-tetraphenyl-1
',1'-biphenyl-2,2'-dimethanol
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8517291A JPH04318043A (en) | 1991-04-17 | 1991-04-17 | Clathrate compound of vulcanization accelerator |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8517291A JPH04318043A (en) | 1991-04-17 | 1991-04-17 | Clathrate compound of vulcanization accelerator |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04318043A true JPH04318043A (en) | 1992-11-09 |
Family
ID=13851245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8517291A Pending JPH04318043A (en) | 1991-04-17 | 1991-04-17 | Clathrate compound of vulcanization accelerator |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04318043A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2569614A (en) * | 2017-12-21 | 2019-06-26 | Hexcel Composites Ltd | A curative composition and a resin composition containing the curative composition |
| GB2580087A (en) * | 2018-12-20 | 2020-07-15 | Hexcel Composites Ltd | Improved thermocurable moulding process |
-
1991
- 1991-04-17 JP JP8517291A patent/JPH04318043A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2569614A (en) * | 2017-12-21 | 2019-06-26 | Hexcel Composites Ltd | A curative composition and a resin composition containing the curative composition |
| GB2569614B (en) * | 2017-12-21 | 2022-04-06 | Hexcel Composites Ltd | A curative composition and a resin composition containing the curative composition |
| US11702516B2 (en) | 2017-12-21 | 2023-07-18 | Hexcel Composites Limited | Curative composition and a resin composition containing the curative composition |
| GB2580087A (en) * | 2018-12-20 | 2020-07-15 | Hexcel Composites Ltd | Improved thermocurable moulding process |
| GB2580087B (en) * | 2018-12-20 | 2022-09-07 | Hexcel Composites Ltd | Improved thermocurable moulding process |
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