CA1057888A - Greffe de silane sur des thermoplastiques ou sur des elastomeres pour leur reticulation - Google Patents

Greffe de silane sur des thermoplastiques ou sur des elastomeres pour leur reticulation

Info

Publication number: CA1057888A
Authority: CA; Canada
Prior art keywords: cross; water; silane; linking; additives
Prior art date: 1974-03-08
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.): Expired

Application number

CA221,364A

Other languages

English (en)

Other versions

CA221364S (en

Inventor

Fritz Glander

Hermann U. Voigt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

KM Kabelmetal AG

Original Assignee

KM Kabelmetal AG

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.)

1974-03-08

Filing date

1975-03-06

Publication date

1979-07-03

1974-03-08 Priority claimed from DE2411141A external-priority patent/DE2411141A1/de

1974-04-20 Priority claimed from DE2419041A external-priority patent/DE2419041A1/de

1974-08-17 Priority claimed from DE19742439534 external-priority patent/DE2439534A1/de

1975-03-06 Application filed by KM Kabelmetal AG filed Critical KM Kabelmetal AG

1976-03-23 Priority to CA248,531A priority Critical patent/CA1078545A/fr

1979-07-03 Application granted granted Critical

1979-07-03 Publication of CA1057888A publication Critical patent/CA1057888A/fr

Status Expired legal-status Critical Current

Links

229910000077 silane Inorganic materials 0.000 title claims abstract description 55
238000004132 cross linking Methods 0.000 title claims abstract description 51
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 44
229920001169 thermoplastic Polymers 0.000 title claims abstract description 11
239000004416 thermosoftening plastic Substances 0.000 title abstract description 6
229920001971 elastomer Polymers 0.000 title description 6
239000000806 elastomer Substances 0.000 title description 4
229910001868 water Inorganic materials 0.000 claims abstract description 67
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 64
239000000654 additive Substances 0.000 claims abstract description 54
239000000463 material Substances 0.000 claims abstract description 39
229920000642 polymer Polymers 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 35
239000000203 mixture Substances 0.000 claims abstract description 20
239000012815 thermoplastic material Substances 0.000 claims abstract description 7
239000013536 elastomeric material Substances 0.000 claims abstract description 5
230000006872 improvement Effects 0.000 claims abstract description 3
239000002245 particle Substances 0.000 claims description 22
238000013019 agitation Methods 0.000 claims description 21
239000000843 powder Substances 0.000 claims description 18
230000000996 additive effect Effects 0.000 claims description 12
238000002844 melting Methods 0.000 claims description 12
230000008018 melting Effects 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 8
239000012530 fluid Substances 0.000 claims description 6
238000000354 decomposition reaction Methods 0.000 claims description 3
WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 claims description 2
229910052602 gypsum Inorganic materials 0.000 claims description 2
239000010440 gypsum Substances 0.000 claims description 2
150000002484 inorganic compounds Chemical class 0.000 claims description 2
229910010272 inorganic material Inorganic materials 0.000 claims description 2
239000004372 Polyvinyl alcohol Substances 0.000 claims 1
229920002451 polyvinyl alcohol Polymers 0.000 claims 1
238000009792 diffusion process Methods 0.000 abstract description 24
238000006243 chemical reaction Methods 0.000 abstract description 11
238000002360 preparation method Methods 0.000 abstract description 2
POSKOXIJDWDKPH-UHFFFAOYSA-N Kelevan Chemical compound ClC1(Cl)C2(Cl)C3(Cl)C4(Cl)C(CC(=O)CCC(=O)OCC)(O)C5(Cl)C3(Cl)C1(Cl)C5(Cl)C42Cl POSKOXIJDWDKPH-UHFFFAOYSA-N 0.000 abstract 1
-1 silane compound Chemical class 0.000 description 43
239000003054 catalyst Substances 0.000 description 40
239000004698 Polyethylene Substances 0.000 description 33
229920000573 polyethylene Polymers 0.000 description 31
150000002978 peroxides Chemical class 0.000 description 16
230000008569 process Effects 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
238000001125 extrusion Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
239000012975 dibutyltin dilaurate Substances 0.000 description 10
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 9
230000008901 benefit Effects 0.000 description 9
229920003023 plastic Polymers 0.000 description 9
239000004033 plastic Substances 0.000 description 9
238000002156 mixing Methods 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
239000000126 substance Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000005977 Ethylene Substances 0.000 description 5
239000012190 activator Substances 0.000 description 5
239000003963 antioxidant agent Substances 0.000 description 5
230000003078 antioxidant effect Effects 0.000 description 5
235000006708 antioxidants Nutrition 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
238000009826 distribution Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000178 monomer Substances 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229920002521 macromolecule Polymers 0.000 description 4
230000002028 premature Effects 0.000 description 4
150000004756 silanes Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
KSNRDYQOHXQKAB-UHFFFAOYSA-N 2,2,4-trimethyl-3,4-dihydro-1h-quinoline Chemical compound C1=CC=C2C(C)CC(C)(C)NC2=C1 KSNRDYQOHXQKAB-UHFFFAOYSA-N 0.000 description 2
229920000181 Ethylene propylene rubber Polymers 0.000 description 2
230000009471 action Effects 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 2
235000012438 extruded product Nutrition 0.000 description 2
238000005243 fluidization Methods 0.000 description 2
229920000578 graft copolymer Polymers 0.000 description 2
238000000265 homogenisation Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000003999 initiator Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
125000005372 silanol group Chemical group 0.000 description 2
238000005507 spraying Methods 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
QWWNXHZDQYBACK-UHFFFAOYSA-N 6-dodecyl-2,2,4-trimethyl-3,4-dihydro-1h-quinoline Chemical compound N1C(C)(C)CC(C)C2=CC(CCCCCCCCCCCC)=CC=C21 QWWNXHZDQYBACK-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920002943 EPDM rubber Polymers 0.000 description 1
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
241000490229 Eucephalus Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010021703 Indifference Diseases 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
241000286904 Leptothecata Species 0.000 description 1
241000283986 Lepus Species 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical group C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229920005601 base polymer Polymers 0.000 description 1
DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000008859 change Effects 0.000 description 1
239000004020 conductor Substances 0.000 description 1
230000002844 continuous effect Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000010292 electrical insulation Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
239000005038 ethylene vinyl acetate Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000013100 final test Methods 0.000 description 1
235000021588 free fatty acids Nutrition 0.000 description 1
239000007863 gel particle Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000009413 insulation Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000005397 methacrylic acid ester group Chemical group 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920000098 polyolefin Polymers 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
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1

Landscapes

Graft Or Block Polymers (AREA)
Processes Specially Adapted For Manufacturing Cables (AREA)
Compositions Of Macromolecular Compounds (AREA)
Processes Of Treating Macromolecular Substances (AREA)

CA221,364A 1974-03-08 1975-03-06 Greffe de silane sur des thermoplastiques ou sur des elastomeres pour leur reticulation Expired CA1057888A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA248,531A CA1078545A (fr)	1974-03-08	1976-03-23	Methode pour greffer du silane sur des polymeres thermoplastiques

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE2411141A DE2411141A1 (de)	1974-03-08	1974-03-08	Verfahren zur herstellung von umhuellungen aus in anwesenheit von fluessigkeit vernetzbaren thermoplasten fuer langgestrecktes gut
DE2419041A DE2419041A1 (de)	1974-04-20	1974-04-20	Verfahren zur herstellung von umhuellungen aus in anwesenheit von feuchtigkeit vernetzbaren thermoplasten fuer langgestrecktes gut
DE19742439534 DE2439534A1 (de)	1974-08-17	1974-08-17	Verfahren zur aufbereitung und vernetzung von peroxidisch- und feuchtigkeitsvernetzbaren materialien

Publications (1)

Publication Number	Publication Date
CA1057888A true CA1057888A (fr)	1979-07-03

Family

ID=27185813

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA221,364A Expired CA1057888A (fr)	1974-03-08	1975-03-06	Greffe de silane sur des thermoplastiques ou sur des elastomeres pour leur reticulation

Country Status (2)

Country	Link
JP (1)	JPS6037128B2 (fr)
CA (1)	CA1057888A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114525101A (zh) *	2022-02-21	2022-05-24	武汉比邻科技发展有限公司	一种低模量高弹性恢复率硅烷改性聚醚密封胶及其制备方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5428386A (en) *	1977-08-04	1979-03-02	Mitsui Petrochem Ind Ltd	Production of silane-modified polyolefin
JPS5477657A (en) *	1977-12-02	1979-06-21	Hitachi Cable Ltd	Crosslinking of polyolefin and production of corsslinked polyolefin insulated wire

1975
- 1975-03-06 CA CA221,364A patent/CA1057888A/fr not_active Expired
- 1975-03-06 JP JP2657575A patent/JPS6037128B2/ja not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114525101A (zh) *	2022-02-21	2022-05-24	武汉比邻科技发展有限公司	一种低模量高弹性恢复率硅烷改性聚醚密封胶及其制备方法
CN114525101B (zh) *	2022-02-21	2023-08-01	武汉比邻科技发展有限公司	一种低模量高弹性恢复率硅烷改性聚醚密封胶及其制备方法

Also Published As

Publication number	Publication date
JPS6037128B2 (ja)	1985-08-24
JPS50126789A (fr)	1975-10-06

Publication	Publication Date	Title
US4058583A (en)	1977-11-15	Grafting of silane on thermoplastics or elastomers for purposes of cross-linking
EP0004034B1 (fr)	1984-02-15	Méthode de réticulation de résines de la série des alpha-polyoléfines
KR101559638B1 (ko)	2015-10-12	고용융장력 프로필렌 폴리머의 제조 과정
US4857250A (en)	1989-08-15	One-extrusion method of making a shaped crosslinkable extruded polymeric product
US4136132A (en)	1979-01-23	Manufacture of extruded products
US4048129A (en)	1977-09-13	Preparing thermo-plastic or elastomeric materials for cross-linking of grafted silane
JPH03167229A (ja)	1991-07-19	シラン架橋剤の押出機への固体供給
DE2310040B2 (de)	1974-10-17	Schäumbare Polymermassen
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CN101255247A (zh)	2008-09-03	免水煮硅烷交联聚烯烃组合物
US4289860A (en)	1981-09-15	Grafting of silane on thermoplastics or elastomers for purposes of cross linking
JP3322818B2 (ja)	2002-09-09	シラン架橋ポリオレフィンの製造方法
EP1572784A1 (fr)	2005-09-14	Polymeres reticules recyclables a chaine principale saturee et a points de reticulation urethanne thermiquement reversible
US20030132017A1 (en)	2003-07-17	Method of manufacturing a cable sheath by extruding and cross-linking a composition based on silane-grafted polymer, and a cable including a sheath obtained by the method
CA1078545A (fr)	1980-05-27	Methode pour greffer du silane sur des polymeres thermoplastiques
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KR0177578B1 (ko)	1999-05-15	전선용 실란 가교 폴리올레핀 조성물 압축성형품의 제조방법
SU686627A3 (ru)	1979-09-15	Способ получени сшиваемых полиолефинов
JP5346823B2 (ja)	2013-11-20	ポリプロピレン系改質樹脂組成物の製造方法、ポリプロピレン系改質樹脂組成物
JPS6037128B2 (ja)	1985-08-24	シラン化合物をグラフトさせることによつて湿分の存在下に架橋し得る熱可塑性物質またはエラストマ−を製造する方法
JPH05174639A (ja)	1993-07-13	架橋ポリエチレン樹脂被覆電線・ケーブル
JPH0665563A (ja)	1994-03-08	蓄熱組成物の製法
JPH07330914A (ja)	1995-12-19	シラン架橋剤保持体およびそれを用いたシラン架橋樹脂成形体の製造方法