CA1250304A - Monomeres de polysiloxane, et leur preparation - Google Patents

Monomeres de polysiloxane, et leur preparation

Info

Publication number: CA1250304A
Authority: CA; Canada
Prior art keywords: carbon atoms; alkyl; substituted; phenyl; siloxane
Prior art date: 1980-12-15
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

CA000459941A

Other languages

English (en)

Inventor

Abe Berger

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.)

Arkema Inc

Original Assignee

M&T Chemicals Inc

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.)

1980-12-15

Filing date

1984-07-27

Publication date

1989-02-21

1980-12-15 Priority claimed from US06/216,599 external-priority patent/US4395527A/en

1984-07-27 Application filed by M&T Chemicals Inc filed Critical M&T Chemicals Inc

1984-07-27 Priority to CA000459941A priority Critical patent/CA1250304A/fr

1989-02-21 Application granted granted Critical

1989-02-21 Publication of CA1250304A publication Critical patent/CA1250304A/fr

Status Expired legal-status Critical Current

Links

-1 Polysiloxane Polymers 0.000 title claims abstract description 244
229920001296 polysiloxane Polymers 0.000 title claims abstract description 80
238000002360 preparation method Methods 0.000 title abstract description 54
239000000178 monomer Substances 0.000 title abstract description 8
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 206
239000007788 liquid Substances 0.000 claims abstract description 41
150000001875 compounds Chemical class 0.000 claims abstract description 37
239000003054 catalyst Substances 0.000 claims abstract description 36
125000003118 aryl group Chemical group 0.000 claims abstract description 34
229910052794 bromium Inorganic materials 0.000 claims abstract description 16
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 14
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 13
229910052740 iodine Inorganic materials 0.000 claims abstract description 13
125000000743 hydrocarbylene group Chemical group 0.000 claims abstract description 9
239000003513 alkali Substances 0.000 claims abstract description 8
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 199
238000006243 chemical reaction Methods 0.000 claims description 154
125000000217 alkyl group Chemical group 0.000 claims description 137
238000000034 method Methods 0.000 claims description 75
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
125000003342 alkenyl group Chemical group 0.000 claims description 52
238000010438 heat treatment Methods 0.000 claims description 38
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 35
125000002947 alkylene group Chemical group 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 29
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
239000003444 phase transfer catalyst Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
239000007858 starting material Substances 0.000 claims description 16
125000000547 substituted alkyl group Chemical group 0.000 claims description 16
125000000304 alkynyl group Chemical group 0.000 claims description 15
150000003983 crown ethers Chemical class 0.000 claims description 14
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
229910052705 radium Inorganic materials 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
125000004122 cyclic group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
229910052701 rubidium Inorganic materials 0.000 claims description 10
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
229910003827 NRaRb Inorganic materials 0.000 claims description 8
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
150000001450 anions Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
229910052710 silicon Inorganic materials 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
229910052787 antimony Inorganic materials 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
229910052785 arsenic Inorganic materials 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
150000004010 onium ions Chemical group 0.000 claims description 5
239000012429 reaction media Substances 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
229910052797 bismuth Inorganic materials 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
229920002554 vinyl polymer Chemical group 0.000 claims description 4
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 3
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
RIFHJAODNHLCBH-UHFFFAOYSA-N methanethione Chemical group S=[CH] RIFHJAODNHLCBH-UHFFFAOYSA-N 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000006413 ring segment Chemical group 0.000 claims description 3
XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 claims description 2
GQRWGIWRQMNZNT-UHFFFAOYSA-N 2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadecane Chemical compound O1CCOCCOCCOCCOC2CCCCC21 GQRWGIWRQMNZNT-UHFFFAOYSA-N 0.000 claims description 2
229940075103 antimony Drugs 0.000 claims description 2
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
FNEPSTUXZLEUCK-UHFFFAOYSA-N benzo-15-crown-5 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C21 FNEPSTUXZLEUCK-UHFFFAOYSA-N 0.000 claims description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 claims description 2
CFODJVUBUNRPAQ-UHFFFAOYSA-N octamethylcyclotetrafurfurylene Chemical group CC1(C)C(O2)=CC=C2C(C)(C)C(O2)=CC=C2C(C)(C)C(O2)=CC=C2C(C)(C)C2=CC=C1O2 CFODJVUBUNRPAQ-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
230000036647 reaction Effects 0.000 claims 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
150000003017 phosphorus Chemical class 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 133
125000000524 functional group Chemical group 0.000 abstract description 12
239000011253 protective coating Substances 0.000 abstract description 8
238000012546 transfer Methods 0.000 abstract description 5
239000004642 Polyimide Substances 0.000 description 219
229920001721 polyimide Polymers 0.000 description 208
239000000243 solution Substances 0.000 description 153
239000000203 mixture Substances 0.000 description 139
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
239000011541 reaction mixture Substances 0.000 description 125
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 112
229910001868 water Inorganic materials 0.000 description 111
235000013350 formula milk Nutrition 0.000 description 104
239000000047 product Substances 0.000 description 91
239000002904 solvent Substances 0.000 description 78
239000000463 material Substances 0.000 description 73
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 70
239000010408 film Substances 0.000 description 62
239000011521 glass Substances 0.000 description 57
150000008064 anhydrides Chemical class 0.000 description 55
239000000306 component Substances 0.000 description 49
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 44
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 42
150000004985 diamines Chemical class 0.000 description 41
239000002253 acid Substances 0.000 description 40
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
238000010992 reflux Methods 0.000 description 39
238000000576 coating method Methods 0.000 description 38
150000001412 amines Chemical class 0.000 description 37
239000007795 chemical reaction product Substances 0.000 description 37
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 32
229920000728 polyester Polymers 0.000 description 32
239000004814 polyurethane Substances 0.000 description 32
229920002635 polyurethane Polymers 0.000 description 32
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
238000009835 boiling Methods 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
239000011248 coating agent Substances 0.000 description 24
230000002829 reductive effect Effects 0.000 description 22
UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
125000005442 diisocyanate group Chemical group 0.000 description 21
229920000647 polyepoxide Polymers 0.000 description 21
239000007787 solid Substances 0.000 description 21
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 20
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
229940117389 dichlorobenzene Drugs 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000003822 epoxy resin Substances 0.000 description 19
238000001914 filtration Methods 0.000 description 19
229920005862 polyol Polymers 0.000 description 19
150000003077 polyols Chemical class 0.000 description 19
230000008569 process Effects 0.000 description 19
150000003839 salts Chemical class 0.000 description 19
239000004065 semiconductor Substances 0.000 description 19
239000000126 substance Substances 0.000 description 19
239000000758 substrate Substances 0.000 description 19
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 18
NHWCFKZCMZMPNO-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)butyl-methyl-trimethylsilyloxysilyl]butoxy]aniline Chemical compound C=1C=CC(N)=CC=1OCCCC[Si](C)(O[Si](C)(C)C)CCCCOC1=CC=CC(N)=C1 NHWCFKZCMZMPNO-UHFFFAOYSA-N 0.000 description 17
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 17
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 17
229910003849 O-Si Inorganic materials 0.000 description 17
229910003872 O—Si Inorganic materials 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 17
229960001760 dimethyl sulfoxide Drugs 0.000 description 17
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 16
239000000543 intermediate Substances 0.000 description 16
229920001169 thermoplastic Polymers 0.000 description 16
239000004416 thermosoftening plastic Substances 0.000 description 16
229960005088 urethane Drugs 0.000 description 16
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 15
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
125000001931 aliphatic group Chemical group 0.000 description 15
238000004132 cross linking Methods 0.000 description 15
239000012948 isocyanate Substances 0.000 description 15
239000012299 nitrogen atmosphere Substances 0.000 description 15
229960001701 chloroform Drugs 0.000 description 14
230000000694 effects Effects 0.000 description 14
229920002545 silicone oil Polymers 0.000 description 14
239000004593 Epoxy Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 13
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 13
229910052753 mercury Inorganic materials 0.000 description 13
239000005056 polyisocyanate Substances 0.000 description 13
238000003756 stirring Methods 0.000 description 13
MJJRMHZJIIYVNW-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)butyl-methyl-trimethylsilyloxysilyl]butoxy]aniline Chemical compound C=1C=C(N)C=CC=1OCCCC[Si](C)(O[Si](C)(C)C)CCCCOC1=CC=C(N)C=C1 MJJRMHZJIIYVNW-UHFFFAOYSA-N 0.000 description 12
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 12
239000004734 Polyphenylene sulfide Substances 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 12
HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 12
239000012071 phase Substances 0.000 description 12
229920001228 polyisocyanate Polymers 0.000 description 12
229920000069 polyphenylene sulfide Polymers 0.000 description 12
230000005855 radiation Effects 0.000 description 12
229920005989 resin Polymers 0.000 description 12
239000011347 resin Substances 0.000 description 12
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
125000003277 amino group Chemical group 0.000 description 11
238000010348 incorporation Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
229920000570 polyether Polymers 0.000 description 11
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 10
WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminobenzenethiol Chemical compound NC1=CC=C(S)C=C1 WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 10
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 10
238000013019 agitation Methods 0.000 description 10
ZPIWMTKLMUAYGY-UHFFFAOYSA-N bis(4-chlorobutyl)-methyl-trimethylsilyloxysilane Chemical compound ClCCCC[Si](C)(O[Si](C)(C)C)CCCCCl ZPIWMTKLMUAYGY-UHFFFAOYSA-N 0.000 description 10
ABIUHPWEYMSGSR-UHFFFAOYSA-N bromocresol purple Chemical compound BrC1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(Br)C(O)=C(C)C=2)=C1 ABIUHPWEYMSGSR-UHFFFAOYSA-N 0.000 description 10
239000000919 ceramic Substances 0.000 description 10
229930195733 hydrocarbon Natural products 0.000 description 10
150000002430 hydrocarbons Chemical class 0.000 description 10
239000010410 layer Substances 0.000 description 10
229940018564 m-phenylenediamine Drugs 0.000 description 10
238000000465 moulding Methods 0.000 description 10
229920000515 polycarbonate Polymers 0.000 description 10
239000004417 polycarbonate Substances 0.000 description 10
239000002861 polymer material Substances 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
229920001187 thermosetting polymer Polymers 0.000 description 10
239000004215 Carbon black (E152) Substances 0.000 description 9
238000005299 abrasion Methods 0.000 description 9
239000001361 adipic acid Substances 0.000 description 9
235000011037 adipic acid Nutrition 0.000 description 9
238000004821 distillation Methods 0.000 description 9
238000001035 drying Methods 0.000 description 9
239000000835 fiber Substances 0.000 description 9
150000003949 imides Chemical class 0.000 description 9
230000006872 improvement Effects 0.000 description 9
150000002513 isocyanates Chemical class 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
229910052979 sodium sulfide Inorganic materials 0.000 description 9
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 9
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 8
UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 8
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
230000015556 catabolic process Effects 0.000 description 8
238000006731 degradation reaction Methods 0.000 description 8
238000011067 equilibration Methods 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
239000006260 foam Substances 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
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MTLAQGJFFFYPSK-UHFFFAOYSA-N trimethyl-[methyl-bis[4-(2-prop-1-enylphenoxy)butyl]silyl]oxysilane Chemical compound CC=CC1=CC=CC=C1OCCCC[Si](C)(O[Si](C)(C)C)CCCCOC1=CC=CC=C1C=CC MTLAQGJFFFYPSK-UHFFFAOYSA-N 0.000 description 1
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AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
ITRNXVSDJBHYNJ-UHFFFAOYSA-N tungsten disulfide Chemical compound S=[W]=S ITRNXVSDJBHYNJ-UHFFFAOYSA-N 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
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238000005303 weighing Methods 0.000 description 1
238000004804 winding Methods 0.000 description 1
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239000011701 zinc Substances 0.000 description 1
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Landscapes

Silicon Polymers (AREA)

CA000459941A 1980-12-15 1984-07-27 Monomeres de polysiloxane, et leur preparation Expired CA1250304A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000459941A CA1250304A (fr)	1980-12-15	1984-07-27	Monomeres de polysiloxane, et leur preparation

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/216,599 US4395527A (en)	1978-05-17	1980-12-15	Siloxane-containing polymers
US216,599		1980-12-15
CA000391385A CA1183634A (fr)	1980-12-15	1981-12-02	Polymeres a teneur de siloxane
CA000459941A CA1250304A (fr)	1980-12-15	1984-07-27	Monomeres de polysiloxane, et leur preparation

Publications (1)

Publication Number	Publication Date
CA1250304A true CA1250304A (fr)	1989-02-21

Family

ID=25669502

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000459941A Expired CA1250304A (fr)	1980-12-15	1984-07-27	Monomeres de polysiloxane, et leur preparation

Country Status (1)

Country	Link
CA (1)	CA1250304A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
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CN112011085A (zh) *	2019-05-28	2020-12-01	赢创运营有限公司	循环利用硅酮的方法
CN116285356A (zh) *	2023-05-09	2023-06-23	江苏晶河电子科技有限公司	一种有机硅弹性体导热吸波材料的合成工艺与应用
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1984
- 1984-07-27 CA CA000459941A patent/CA1250304A/fr not_active Expired

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN112011085A (zh) *	2019-05-28	2020-12-01	赢创运营有限公司	循环利用硅酮的方法
CN116285356A (zh) *	2023-05-09	2023-06-23	江苏晶河电子科技有限公司	一种有机硅弹性体导热吸波材料的合成工艺与应用
CN117959956A (zh) *	2024-03-11	2024-05-03	江苏泷膜科技有限公司	一种选择透过性抗污染特种分离膜的制备方法
CN117959956B (zh) *	2024-03-11	2024-06-28	江苏泷膜科技有限公司	一种选择透过性抗污染特种分离膜的制备方法

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Date	Code	Title	Description
2006-02-21	MKEX	Expiry

Publication	Publication Date	Title
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US4499149A (en)	1985-02-12	Siloxane-containing polymers
CA1183634A (fr)	1985-03-05	Polymeres a teneur de siloxane
KR940000962B1 (ko)	1994-02-07	개량된 폴리(아미드-아미드산), 폴리아미드산, 폴리(에스테르아미드산), 폴리(아미드-이미드), 폴리이미드, 폴리(에스테르이미드)
CA1325075C (fr)	1993-12-07	Polyimidosiloxanes solubles et methodes pour leur preparation et leur utilisation
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