NO814254L - Polysiloksanholdige polymerer - Google Patents

Info

Publication number

NO814254L

NO814254L NO814254A NO814254A NO814254L NO 814254 L NO814254 L NO 814254L NO 814254 A NO814254 A NO 814254A NO 814254 A NO814254 A NO 814254A NO 814254 L NO814254 L NO 814254L

Authority

NO

Norway

Prior art keywords

carbon atoms

alkyl

substituted

alkenyl

phenyl

Prior art date

1980-12-15

Links

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• 229920000642 polymer Polymers 0.000 title claims description 147
• 125000004432 carbon atom Chemical group C* 0.000 claims description 425
• -1 polysiloxane unit Polymers 0.000 claims description 413
• 229920001721 polyimide Polymers 0.000 claims description 235
• 239000004642 Polyimide Substances 0.000 claims description 233
• 125000000217 alkyl group Chemical group 0.000 claims description 202
• 229920001296 polysiloxane Polymers 0.000 claims description 196
• 239000000203 mixture Substances 0.000 claims description 172
• 238000006243 chemical reaction Methods 0.000 claims description 142
• 125000003342 alkenyl group Chemical group 0.000 claims description 95
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
• 239000002904 solvent Substances 0.000 claims description 82
• 238000000034 method Methods 0.000 claims description 73
• 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 claims description 65
• 239000011521 glass Substances 0.000 claims description 64
• 125000002947 alkylene group Chemical group 0.000 claims description 61
• 150000008064 anhydrides Chemical class 0.000 claims description 59
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 49
• 150000004985 diamines Chemical class 0.000 claims description 44
• 238000000576 coating method Methods 0.000 claims description 40
• 239000002253 acid Substances 0.000 claims description 39
• 150000001412 amines Chemical class 0.000 claims description 39
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 239000007795 chemical reaction product Substances 0.000 claims description 38
• 239000007788 liquid Substances 0.000 claims description 37
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
• 229910052794 bromium Inorganic materials 0.000 claims description 35
• 239000000460 chlorine Substances 0.000 claims description 35
• 229910052801 chlorine Inorganic materials 0.000 claims description 35
• 229920000728 polyester Polymers 0.000 claims description 35
• 125000000304 alkynyl group Chemical group 0.000 claims description 34
• 239000004814 polyurethane Substances 0.000 claims description 34
• 229920002635 polyurethane Polymers 0.000 claims description 34
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
• 125000003545 alkoxy group Chemical group 0.000 claims description 33
• 150000001875 compounds Chemical class 0.000 claims description 33
• 239000012948 isocyanate Substances 0.000 claims description 31
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 30
• 229910052731 fluorine Inorganic materials 0.000 claims description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 239000011248 coating agent Substances 0.000 claims description 28
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 27
• 150000002513 isocyanates Chemical class 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 25
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 229920000647 polyepoxide Polymers 0.000 claims description 24
• 239000000758 substrate Substances 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 239000003444 phase transfer catalyst Substances 0.000 claims description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000000743 hydrocarbylene group Chemical group 0.000 claims description 20
• 239000004065 semiconductor Substances 0.000 claims description 20
• 239000000126 substance Substances 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
• 125000001931 aliphatic group Chemical group 0.000 claims description 17
• 125000004414 alkyl thio group Chemical group 0.000 claims description 17
• 239000011737 fluorine Substances 0.000 claims description 17
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 16
• 229920002647 polyamide Polymers 0.000 claims description 16
• 239000004952 Polyamide Substances 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 14
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 14
• 150000003983 crown ethers Chemical class 0.000 claims description 14
• 229910052740 iodine Inorganic materials 0.000 claims description 14
• 229920000515 polycarbonate Polymers 0.000 claims description 14
• 239000004417 polycarbonate Substances 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• RIFHJAODNHLCBH-UHFFFAOYSA-N methanethione Chemical group S=[CH] RIFHJAODNHLCBH-UHFFFAOYSA-N 0.000 claims description 12
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 11
• IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 11
• 125000000524 functional group Chemical group 0.000 claims description 11
• 229910052751 metal Inorganic materials 0.000 claims description 11
• 239000002184 metal Substances 0.000 claims description 11
• 125000006413 ring segment Chemical group 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 239000000835 fiber Substances 0.000 claims description 10
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 10
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
• 229920002554 vinyl polymer Polymers 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
• 239000004734 Polyphenylene sulfide Substances 0.000 claims description 9
• 229920000069 polyphenylene sulfide Polymers 0.000 claims description 9
• GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 239000000919 ceramic Substances 0.000 claims description 8
• 229920002492 poly(sulfone) Polymers 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 239000000853 adhesive Substances 0.000 claims description 7
• 230000001070 adhesive effect Effects 0.000 claims description 7
• QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 239000012429 reaction media Substances 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
• 150000001450 anions Chemical group 0.000 claims description 6
• 235000013824 polyphenols Nutrition 0.000 claims description 6
• IBRQUKZZBXZOBA-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 IBRQUKZZBXZOBA-UHFFFAOYSA-N 0.000 claims description 5
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 5
• 150000004820 halides Chemical group 0.000 claims description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
• 125000004957 naphthylene group Chemical group 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 229920000265 Polyparaphenylene Polymers 0.000 claims description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
• 229910052787 antimony Inorganic materials 0.000 claims description 4
• 229910052785 arsenic Inorganic materials 0.000 claims description 4
• 229910052797 bismuth Inorganic materials 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 239000004020 conductor Substances 0.000 claims description 4
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
• 239000011159 matrix material Substances 0.000 claims description 4
• 150000004010 onium ions 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
• 150000008065 acid anhydrides Chemical class 0.000 claims description 3
• 239000002245 particle Substances 0.000 claims description 3
• 229910052698 phosphorus Inorganic materials 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
• 229910052581 Si3N4 Inorganic materials 0.000 claims description 2
• 239000003513 alkali Substances 0.000 claims description 2
• 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
• WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
• 150000001491 aromatic compounds Chemical class 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
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
• PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 2
• YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-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
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 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
• 150000003017 phosphorus Chemical class 0.000 claims description 2
• 150000008442 polyphenolic compounds Chemical class 0.000 claims description 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 2
• 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
• 229910014033 C-OH Inorganic materials 0.000 claims 1
• QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical group ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims 1
• 229910014570 C—OH Inorganic materials 0.000 claims 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
• 125000001153 fluoro group Chemical group F* 0.000 claims 1
• 150000002431 hydrogen Chemical class 0.000 claims 1
• 150000007524 organic acids Chemical class 0.000 claims 1
• 239000000243 solution Substances 0.000 description 145
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
• 239000011541 reaction mixture Substances 0.000 description 129
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 113
• 239000000047 product Substances 0.000 description 81
• 239000000463 material Substances 0.000 description 75
• 239000010408 film Substances 0.000 description 64
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• 238000002360 preparation method Methods 0.000 description 54
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 44
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 41
• 238000010992 reflux Methods 0.000 description 41
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• 230000002829 reductive effect Effects 0.000 description 35
• 238000010438 heat treatment Methods 0.000 description 34
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 33
• 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
• 239000003054 catalyst Substances 0.000 description 32
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• 238000009835 boiling Methods 0.000 description 25
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 22
• 239000012467 final product Substances 0.000 description 22
• OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 21
• 230000015572 biosynthetic process Effects 0.000 description 21
• 229940117389 dichlorobenzene Drugs 0.000 description 21
• 238000001914 filtration Methods 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• 239000003822 epoxy resin Substances 0.000 description 20
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 20
• 238000003756 stirring Methods 0.000 description 20
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
• 229920005862 polyol Polymers 0.000 description 19
• 150000003077 polyols Chemical class 0.000 description 19
• 125000005442 diisocyanate group Chemical group 0.000 description 18
• 150000003839 salts Chemical class 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
• 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 16
• 238000004519 manufacturing process Methods 0.000 description 16
• 229920001169 thermoplastic Polymers 0.000 description 16
• 239000004416 thermosoftening plastic Substances 0.000 description 16
• 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
• 238000004132 cross linking Methods 0.000 description 15
• 239000012299 nitrogen atmosphere Substances 0.000 description 15
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 14
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 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 14
• 229920002545 silicone oil Polymers 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 238000004090 dissolution Methods 0.000 description 13
• 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 13
• 229920000570 polyether Polymers 0.000 description 13
• 239000005056 polyisocyanate Substances 0.000 description 13
• 229920001228 polyisocyanate Polymers 0.000 description 13
• RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 12
• 239000004593 Epoxy Substances 0.000 description 12
• 238000004458 analytical method Methods 0.000 description 12
• 229940106691 bisphenol a Drugs 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
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• 238000005481 NMR spectroscopy Methods 0.000 description 11
• 239000001361 adipic acid Substances 0.000 description 11
• 235000011037 adipic acid Nutrition 0.000 description 11
• 125000003277 amino group Chemical group 0.000 description 11
• 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 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 150000003949 imides Chemical class 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 229940018564 m-phenylenediamine Drugs 0.000 description 11
• 230000005855 radiation Effects 0.000 description 11
• 229920005989 resin Polymers 0.000 description 11
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