JP5908970B2 - 硬化性フルオロエラストマー組成物 - Google Patents
硬化性フルオロエラストマー組成物 Download PDFInfo
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- JP5908970B2 JP5908970B2 JP2014502890A JP2014502890A JP5908970B2 JP 5908970 B2 JP5908970 B2 JP 5908970B2 JP 2014502890 A JP2014502890 A JP 2014502890A JP 2014502890 A JP2014502890 A JP 2014502890A JP 5908970 B2 JP5908970 B2 JP 5908970B2
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- nhnh
- hydrazide
- fluoroelastomer
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- curing
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- 239000000203 mixture Substances 0.000 title claims description 52
- 229920001973 fluoroelastomer Polymers 0.000 title claims description 36
- 239000000178 monomer Substances 0.000 claims description 22
- 125000002560 nitrile group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 description 15
- -1 hexafluoropropylene, tetrafluoroethylene Chemical group 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 7
- 238000007906 compression Methods 0.000 description 7
- 230000006835 compression Effects 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 7
- 150000002825 nitriles Chemical group 0.000 description 7
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- MOCKWYUCPREFCZ-UHFFFAOYSA-N chondroitin sulfate E (GalNAc4,6diS-GlcA), precursor 5a Chemical compound NNC(=O)NC1=CC=CC=C1 MOCKWYUCPREFCZ-UHFFFAOYSA-N 0.000 description 4
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BNXHWDWODIHJEH-UHFFFAOYSA-N 1-amino-3-phenylurea;hydrochloride Chemical compound Cl.NNC(=O)NC1=CC=CC=C1 BNXHWDWODIHJEH-UHFFFAOYSA-N 0.000 description 3
- MOKRDWKSHLLYKM-UHFFFAOYSA-N 2-hydrazinyl-2-oxoacetamide Chemical compound NNC(=O)C(N)=O MOKRDWKSHLLYKM-UHFFFAOYSA-N 0.000 description 3
- VVVFQQJJJRFDTE-UHFFFAOYSA-N 3-amino-1,1-diphenylurea Chemical compound C=1C=CC=CC=1N(C(=O)NN)C1=CC=CC=C1 VVVFQQJJJRFDTE-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000004811 fluoropolymer Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000013022 formulation composition Substances 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 3
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 2
- GFQJOAYQSOWWOE-UHFFFAOYSA-N 1-amino-3-(hydrazinecarbonyl)urea Chemical compound NNC(=O)NC(=O)NN GFQJOAYQSOWWOE-UHFFFAOYSA-N 0.000 description 2
- BGEVFSCRPUOYHH-UHFFFAOYSA-N 1-amino-3-(hydrazinecarbonylamino)urea Chemical compound NNC(=O)NNC(=O)NN BGEVFSCRPUOYHH-UHFFFAOYSA-N 0.000 description 2
- LYIPDZSLYLDLCU-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxypropanenitrile Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C#N LYIPDZSLYLDLCU-UHFFFAOYSA-N 0.000 description 2
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 2
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical group FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
- QAERDLQYXMEHEB-UHFFFAOYSA-N 1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=CC(F)(F)F QAERDLQYXMEHEB-UHFFFAOYSA-N 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- CUDYUNNRMLWYTR-UHFFFAOYSA-N 1-amino-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1(N)C(O)=O CUDYUNNRMLWYTR-UHFFFAOYSA-N 0.000 description 1
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 1
- GQILCMONWYJNFP-UHFFFAOYSA-N 4-[2-(3-amino-4-anilinophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-1-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC(C(C=2C=C(N)C(NC=3C=CC=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)=CC=C1NC1=CC=CC=C1 GQILCMONWYJNFP-UHFFFAOYSA-N 0.000 description 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- KEACLAVDTZRACA-UHFFFAOYSA-N [4-(2-carbamoylhydrazinyl)anilino]urea Chemical group NC(=O)NNC1=CC=C(NNC(N)=O)C=C1 KEACLAVDTZRACA-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001411 amidrazones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000019241 carbon black Nutrition 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical group C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 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
- 238000005096 rolling process Methods 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F224/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/24—Derivatives of hydrazine
- C08K5/25—Carboxylic acid hydrazides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08L27/18—Homopolymers or copolymers or tetrafluoroethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
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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)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
A) ニトリル基含有硬化部位モノマーの共重合単位を含むフルオロエラストマーと;
B) 一般式R1(C(O))nNHNHR2のヒドラジド(式中nは1または2であり;R1はNH2、NHNH2、NHR3、NR3 2、NHNHC(O)NH2、NHNHC(O)NHNH2、NHNHR2またはNHC(O)NHNH2であり;R2はH、アルキル、アリール、複素環、CO2R3、C(O)R3、CH2R4またはC(O)R4であり;R3はアルキル、アリール、複素環またはCH2R4であり;R4はフルオロアルキル基である)と;
を含む硬化性組成物に関する。
CF2=CFO(Rf’O)n(Rf’’O)mRf (I)
のものが含まれ、式中、Rf’およびRf’’は、2〜6個の炭素原子の異なる直鎖または分岐ペルフルオロアルキレン基であり、mとnは独立して0〜10であり、Rfは1〜6個の炭素原子のペルフルオロアルキル基である。
CF2=CFO(CF2CFXO)nRf (II)
の組成物が含まれ、式中XはFまたはCF3であり、nは0〜5、Rfは1〜6個の炭素原子のペルフルオロアルキル基である。
CF2=CFO[(CF2)mCF2CFZO]nRf (III)
のものが含まれ、式中、Rfは1〜6個の炭素原子を有するペルフルオロアルキル基であり、m=0または1であり、n=0〜5であり、Z=FまたはCF3である。この部類の好ましい成員は、RfがC3F7であり、m=0、n=1のものである。
CF2=CFO[(CF2CF{CF3}O)n(CF2CF2CF2O)m(CF2)p]CxF2x+1 (IV)
の化合物が含まれ、式中mとnは独立して0〜10であり、p=0〜3、x=1〜5である。この部類の好ましい成員としては、n=0〜1、m=0〜1そしてx=1である化合物がある。
CF2=CFOCF2CF(CF3)O(CF2O)mCnF2n+1 (V)
が含まれ、式中n=1〜5、m=1〜3であり、好ましくはn=1である。
CF2=CF−O(CF2)n−CN (VI)
(式中、n=2〜12、好ましくは2〜6である);
CF2=CF−O[CF2−CFCF3−O]n−CF2−CFCF3−CN (VII)
(式中、n=0〜4、好ましくは0〜2である);
CF2=CF−[OCF2CFCF3]x−O−(CF2)n−CN (VIII)
(式中、x=1〜2であり、n=1〜4である);
CF2=CF−O−(CF2)n−O−CF(CF3)CN (IX)
(式中、n=2〜4である)。
CF2=CFOCF2CF(CF3)OCF2CF2CN (X)
すなわち、ペルフルオロ(8−シアノ−5−メチル−3,6−ジオキサ−1−オクテン)または8−CNVEである。
硬化特性
硬化特性は、以下の条件下でモンサントMDR2000計器を用いて測定された:
移動ダイ周波数:1.66Hz
振幅:±0.5度
温度:別段の指摘のないかぎり190℃
試料サイズ:直径1.5インチ(38mm)のディスク
試験持続時間:30分
MH:dN・m単位で表わした最大トルクレベル、
ML:dN・m単位で表わした最小トルクレベル、
TC90:最大トルクの90%に至る時間、分単位、
FFKM− 61.8モルパーセント単位のTFE、37.4モルパーセント単位のPMVEおよび0.80モルパーセント単位の8−CNVEを含むターポリマーを、米国特許第5,789,489号明細書中に記載の一般的プロセスにしたがって調製した。
FKM− 23.3モルパーセント単位のTFE、50.7モルパーセント単位のVF2、25.1モルパーセント単位のヘキサフルオロプロピレンおよび0.90モルパーセント単位の8−CNVEを含むターポリマー。
本発明の硬化性組成物を、表Iに示された割合でゴム用2本ロール機上で配合した。配合組成物は、表I中で、実施例1(Alfa−Aesarから入手可能な4−フェニルセミカルバジド)および実施例2(Sigma−Aldrichから入手可能なカルボヒドラジド)と標識されている。配合組成物の硬化特性も表Iに示されている。Tc90プラス5分の間190℃の温度で硬化性組成物をプレス硬化させることによってOリングを製造し、その後、室温からの緩慢な温度上昇の後26時間305℃の温度で窒素雰囲気中で後硬化させた。圧縮永久歪と体積膨潤度の値も、表Iに示されている。
本発明の硬化性組成物を、表IIに示された割合でゴム用2本ロール機上で配合した。配合組成物は表II中で、実施例3(Acros Organicsから入手可能なオキサミン酸ヒドラジド、実施例4(Sigma Aldrichから入手可能なオキサリルジヒドラジド)および実施例5(塩化水素が省略されている点を除き米国特許第4,482,738号明細書の実施例1中の一般手順にしたがって尿素およびヒドラジン水和物から調製されたセミカルバジド)と標識されている。配合組成物の硬化特性も表IIに示されている。
本発明の硬化性組成物を、表IIIに示された割合でゴム用2本ロール機上で配合した。配合組成物は、表III中で実施例6(Sigma−Aldrichから入手可能な4−フェニルセミカルバジドヒドロクロリド)、実施例7(ジフェニルカルバモイルクロリドおよび無水ヒドラジンから調製された4,4−ジフェニルセミカルバジド)および実施例8(Sigma−Aldrichから入手可能なセミカルバジドヒドロクロリド)と標識されている。配合組成物の硬化特性も、表IIIに示されている。
本発明の硬化性組成物を、表IVに示された割合でゴム用2本ロール機上で配合した。配合組成物は、表IV中で、実施例9(カルボヒドラジド)と標識されている。配合組成物の硬化特性(199℃での)も表IVに示されている。Tc90プラス5分の間、199℃の温度で硬化性組成物をプレス硬化させることによってOリングを製造し、その後、室温からの緩慢な温度上昇の後8時間260℃の温度で窒素雰囲気中で後硬化させた。圧縮永久歪も、表IVに示されている。
1.A) ニトリル基含有硬化部位モノマーの共重合単位を含むフルオロエラストマーと;
B) 一般式R1(C(O))nNHNHR2のヒドラジド(式中nは1または2であり;R1はNH2、NHNH2、NHR3、NR3 2、NHNHC(O)NH2、NHNHC(O)NHNH2、NHNHR2またはNHC(O)NHNH2であり;R2はH、アルキル、アリール、複素環、CO2R3、C(O)R3、CH2R4またはC(O)R4であり;R3はアルキル、アリール、複素環またはCH2R4であり、R4はフルオロアルキル基である)と;
を含む硬化性組成物。
2.nが1であり;R1がNH2、NHNH2、NHR3、NR3 2、NHNHC(O)NH2、NHNHC(O)NHNH2、NHNHR2またはNHC(O)NHNH2であり;R2がHである、1に記載の硬化性組成物。
3.nが2であり;R1がNH2、NHNH2、NHR3、NR3 2、NHNHC(O)NH2、NHNHC(O)NHNH2、NHNHR2またはNHC(O)NHNH2であり;R2がHである、1に記載の硬化性組成物。
4.nが1であり;R1がNH2、NHNH2、NHR3、NR3 2、NHNHC(O)NH2、NHNHC(O)NHNH2、NHNHR2またはNHC(O)NHNH2であり;R2がCO2R3である、1に記載の硬化性組成物。
5.nが2であり;R1はNH2、NHNH2、NHR3、NR3 2、NHNHC(O)NH2、NHNHC(O)NHNH2、NHNHR2またはNHC(O)NHNH2であり;R2がCO2R3である、1に記載の硬化性組成物。
6.前記ヒドラジドが、カルボヒドラジド;炭酸ジヒドラジド、ジヒドロクロリド;4−フェニルセミカルバジド;4−フェニルセミカルバジドヒドロクロリド;4,4−ジフェニルセミカルバジド;オキサミン酸ヒドラジド;オキサリルジヒドラジド;セミカルバジド;1,2−ヒドラジンジカルボン酸、ジヒドラジド;ジアミノビウレット;チオカルボヒドラジド;およびチオセミカルバジドからなる群から選択される、1に記載の硬化性組成物。
7.前記ヒドラジドの少なくとも1つの酸素原子が硫黄原子で置換されている、1に記載の硬化性組成物。
8.さらに硬化促進剤を含む、1に記載の硬化性組成物。
9.1に記載の組成物から製造される硬化物品。
10.少なくとも168時間225℃の水に曝露した後ASTM D1414にしたがって測定した体積膨潤度が5%未満であり、ASTM D395にしたがって測定した300℃、70時間、15%圧縮での圧縮永久歪が70%未満である、9に記載の硬化物品。
Claims (2)
- A) ニトリル基含有硬化部位モノマーの共重合単位を含むフルオロエラストマーと;
B) 一般式R1(C(O))nNHNHR2のヒドラジド(式中nは1または2であり;
R1はNH2、NHNH2、NHR3、NR 3 2 、NHNHR 2 またはNHC(O)NHNH2であり;
R2はH、CO 2 R 3 、CH2R4またはC(O)R4であり;
R3はアルキル、アリール、複素環またはCH2R4であり、R4はフルオロアルキル基である)と;を含む硬化性組成物。 - 請求項1に記載の組成物から製造される硬化物品。
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