NO125392B - - Google Patents

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Info

Publication number: NO125392B
Authority: NO; Norway
Prior art keywords: parts; approx; methacrylate; terpolymer; styrene
Prior art date: 1966-08-10

Application number

NO169276A

Other languages

English (en)

Norwegian (no)

Inventor

B Jacknow

J Moriconi

Original Assignee

Rank Xerox Ltd

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.)

1966-08-10

Filing date

1967-08-07

Publication date

1972-09-04

1967-08-07 Application filed by Rank Xerox Ltd filed Critical Rank Xerox Ltd

1972-09-04 Publication of NO125392B publication Critical patent/NO125392B/no

Links

PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 66
229920001897 terpolymer Polymers 0.000 claims description 45
-1 acrylate ester Chemical class 0.000 claims description 21
FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 20
229920000642 polymer Polymers 0.000 claims description 18
150000003961 organosilicon compounds Chemical class 0.000 claims description 16
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical class CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 12
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 11
XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 10
229910052710 silicon Inorganic materials 0.000 claims description 10
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
125000000962 organic group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 5
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
150000001282 organosilanes Chemical class 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
238000000576 coating method Methods 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 22
239000011248 coating agent Substances 0.000 description 21
238000000034 method Methods 0.000 description 20
239000011521 glass Substances 0.000 description 18
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 15
239000000463 material Substances 0.000 description 15
238000006116 polymerization reaction Methods 0.000 description 15
238000000149 argon plasma sintering Methods 0.000 description 14
239000000178 monomer Substances 0.000 description 14
239000000376 reactant Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
238000003756 stirring Methods 0.000 description 13
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 10
229920003023 plastic Polymers 0.000 description 10
239000004033 plastic Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
238000001035 drying Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
239000007789 gas Substances 0.000 description 8
229940048053 acrylate Drugs 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229910001873 dinitrogen Inorganic materials 0.000 description 6
239000000203 mixture Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000000758 substrate Substances 0.000 description 5
239000003999 initiator Substances 0.000 description 4
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
150000003440 styrenes Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000004913 activation Effects 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
229920001558 organosilicon polymer Polymers 0.000 description 2
LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000010703 silicon Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-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
238000005406 washing Methods 0.000 description 2
FPDDOFWJHHYHOU-UHFFFAOYSA-N (3-ethenylphenyl)methanol Chemical compound OCC1=CC=CC(C=C)=C1 FPDDOFWJHHYHOU-UHFFFAOYSA-N 0.000 description 1
IZMZREOTRMMCCB-UHFFFAOYSA-N 1,4-dichloro-2-ethenylbenzene Chemical compound ClC1=CC=C(Cl)C(C=C)=C1 IZMZREOTRMMCCB-UHFFFAOYSA-N 0.000 description 1
PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
ZCDHKYZAFKYYIU-UHFFFAOYSA-N 1-chloro-4-ethenyl-2-fluorobenzene Chemical compound FC1=CC(C=C)=CC=C1Cl ZCDHKYZAFKYYIU-UHFFFAOYSA-N 0.000 description 1
LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
NCOMFXGCBNGEFH-UHFFFAOYSA-N 1-ethenyl-4-(3-methylbutoxy)benzene Chemical compound CC(C)CCOC1=CC=C(C=C)C=C1 NCOMFXGCBNGEFH-UHFFFAOYSA-N 0.000 description 1
OBRYRJYZWVLVLF-UHFFFAOYSA-N 1-ethenyl-4-ethoxybenzene Chemical compound CCOC1=CC=C(C=C)C=C1 OBRYRJYZWVLVLF-UHFFFAOYSA-N 0.000 description 1
WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
KWHSBYQFELZKKS-UHFFFAOYSA-N 1-ethenyl-4-iodobenzene Chemical compound IC1=CC=C(C=C)C=C1 KWHSBYQFELZKKS-UHFFFAOYSA-N 0.000 description 1
QBXXSFMGAKBCBX-UHFFFAOYSA-N 1-ethenyl-4-nonadecylbenzene Chemical compound CCCCCCCCCCCCCCCCCCCC1=CC=C(C=C)C=C1 QBXXSFMGAKBCBX-UHFFFAOYSA-N 0.000 description 1
LMAUULKNZLEMGN-UHFFFAOYSA-N 1-ethyl-3,5-dimethylbenzene Chemical compound CCC1=CC(C)=CC(C)=C1 LMAUULKNZLEMGN-UHFFFAOYSA-N 0.000 description 1
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 1
ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
DSIWLDCXHHMNQL-UHFFFAOYSA-N 2-ethenyl-1,4-difluorobenzene Chemical compound FC1=CC=C(F)C(C=C)=C1 DSIWLDCXHHMNQL-UHFFFAOYSA-N 0.000 description 1
WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
FUVRWYAHEUSYPD-UHFFFAOYSA-N 6-hexyldodec-1-enylbenzene Chemical compound CCCCCCC(CCCCCC)CCCC=CC1=CC=CC=C1 FUVRWYAHEUSYPD-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920000298 Cellophane Polymers 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
PDAVOLCVHOKLEO-UHFFFAOYSA-N acetyl benzenecarboperoxoate Chemical compound CC(=O)OOC(=O)C1=CC=CC=C1 PDAVOLCVHOKLEO-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
239000011324 bead Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
VXTQKJXIZHSXBY-UHFFFAOYSA-N butan-2-yl 2-methylprop-2-enoate Chemical compound CCC(C)OC(=O)C(C)=C VXTQKJXIZHSXBY-UHFFFAOYSA-N 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
TXTCTCUXLQYGLA-UHFFFAOYSA-L calcium;prop-2-enoate Chemical compound [Ca+2].[O-]C(=O)C=C.[O-]C(=O)C=C TXTCTCUXLQYGLA-UHFFFAOYSA-L 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
MAYIDWCWWMOISO-UHFFFAOYSA-N dichloro-bis(ethenyl)silane Chemical compound C=C[Si](Cl)(Cl)C=C MAYIDWCWWMOISO-UHFFFAOYSA-N 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
BRDYCNFHFWUBCZ-UHFFFAOYSA-N dodecaneperoxoic acid Chemical compound CCCCCCCCCCCC(=O)OO BRDYCNFHFWUBCZ-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000011953 free-radical catalyst Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
RXYJPCXASAZAQZ-UHFFFAOYSA-N hexadecan-7-yl prop-2-enoate Chemical compound CCCCCCCCCC(OC(=O)C=C)CCCCCC RXYJPCXASAZAQZ-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229940091853 isobornyl acrylate Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000123 paper Substances 0.000 description 1
GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
150000004819 silanols Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229940047670 sodium acrylate Drugs 0.000 description 1
SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
- 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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/10—Developers with toner particles characterised by carrier particles
- G03G9/113—Developers with toner particles characterised by carrier particles having coatings applied thereto
- G03G9/1132—Macromolecular components of coatings
- G03G9/1133—Macromolecular components of coatings obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/10—Developers with toner particles characterised by carrier particles
- G03G9/113—Developers with toner particles characterised by carrier particles having coatings applied thereto
- G03G9/1132—Macromolecular components of coatings
- G03G9/1135—Macromolecular components of coatings obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/1136—Macromolecular components of coatings obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31667—Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product

Landscapes

Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Spectroscopy & Molecular Physics (AREA)
General Physics & Mathematics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Joining Of Glass To Other Materials (AREA)
Paints Or Removers (AREA)
Adhesives Or Adhesive Processes (AREA)
Laminated Bodies (AREA)

NO169276A 1966-08-10 1967-08-07 NO125392B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US57138866A	1966-08-10	1966-08-10

Publications (1)

Publication Number	Publication Date
NO125392B true NO125392B (fr)	1972-09-04

Family

ID=24283491

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO169276A NO125392B (fr)	1966-08-10	1967-08-07

Country Status (9)

Country	Link
US (1)	US3467634A (fr)
BE (1)	BE702403A (fr)
CH (1)	CH484210A (fr)
DE (1)	DE1745341A1 (fr)
ES (1)	ES343902A1 (fr)
GB (1)	GB1200756A (fr)
NL (1)	NL6711065A (fr)
NO (1)	NO125392B (fr)
SE (1)	SE339752B (fr)

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* Cited by examiner, † Cited by third party
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US4070186A (en) *	1974-08-26	1978-01-24	Xerox Corporation	Tribo modified toner materials via silylation and electrostatographic imaging process
US3997485A (en) *	1975-02-11	1976-12-14	Ppg Industries, Inc.	Ambient temperature, moisture curable coating compositions which form films having excellent gloss
US4080304A (en) *	1975-06-16	1978-03-21	The Dow Chemical Company	Hydrocarbon oil compositions containing polymers to control viscosity temperature relationship
JPS55152745A (en) *	1979-05-17	1980-11-28	Kanegafuchi Chem Ind Co Ltd	Curable composition
US4277593A (en) *	1979-12-10	1981-07-07	Hercules Incorporated	Novel polymers based on azido and silane monomers
DE3166237D1 (en)	1980-03-03	1984-10-31	Scott Bader Co	Ceramic tile adhesives
DE3265777D1 (en) *	1981-05-08	1985-10-03	Toray Industries	Coating composition
GB2127422B (en) *	1982-08-27	1987-02-25	Contact Lenses	Prostheses contact lenses and polymers therefor
US4499150A (en) *	1983-03-29	1985-02-12	Ppg Industries, Inc.	Color plus clear coating method utilizing addition interpolymers containing alkoxy silane and/or acyloxy silane groups
ZA85159B (en) *	1984-02-01	1986-09-24	Ppg Industries Inc	Coating compositions containing polymeric microparticles
JPS61228078A (ja) *	1985-04-01	1986-10-11	Shin Etsu Chem Co Ltd	粘着剤用離型性組成物
JPS63168469A (ja) *	1986-12-29	1988-07-12	Shin Etsu Chem Co Ltd	室温硬化性塗料組成物
US5106930A (en) *	1988-09-28	1992-04-21	Ioptex Research Inc.	Contact lenses
US5032455A (en) *	1989-01-03	1991-07-16	Ppg Industries, Inc.	Silyated addition polymers with pendant ionic moieties
US4983699A (en) *	1989-01-03	1991-01-08	Ppg Industries, Inc.	Silylated addition polymers with pendant ionic moieties
US5213740A (en) *	1989-05-30	1993-05-25	Xerox Corporation	Processes for the preparation of toner compositions
WO1992014788A1 (fr) *	1991-02-14	1992-09-03	S.C. Johnson & Son, Inc.	Compositions polymeres melangees
US5304449A (en) *	1992-11-30	1994-04-19	Xerox Corporation	Toner and developer compositions with pyridinium compounds and tetrasubstituted ammonium salts as charge enhancing additives
US5985524A (en) *	1997-03-28	1999-11-16	International Business Machines Incorporated	Process for using bilayer photoresist
US6177222B1 (en)	1998-03-12	2001-01-23	Xerox Corporation	Coated photographic papers
US7208252B2 (en) *	2004-06-30	2007-04-24	Xerox Corporation	Magnetic toner and conductive developer compositions
US7329476B2 (en)	2005-03-31	2008-02-12	Xerox Corporation	Toner compositions and process thereof
JP5992416B2 (ja) *	2010-09-07	2016-09-14	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	電子不足オレフィン、電子吸引性置換基を持たないオレフィン及びアルコキシビニルシランから成るターポリマー
CN102649037B (zh) *	2011-05-04	2014-06-11	京东方科技集团股份有限公司	一种电子墨水微胶囊及其制作方法
US8802345B2 (en)	2012-10-17	2014-08-12	Xerox Corporation	Dispensing toner additives via carrier dispense
US8852843B2 (en)	2012-11-06	2014-10-07	Xerox Corporation	Dispensing toner additives via carrier dispense and clear toner
US20140303312A1 (en) *	2013-03-15	2014-10-09	The Sherwin-Williams Company	Flourinated silane-modified polyacrylic resin
TW202014177A (zh)	2018-10-11	2020-04-16	美商陶氏全球科技責任有限公司	防曬配方
TW202023523A (zh)	2018-10-11	2020-07-01	美商陶氏全球科技責任有限公司	彩妝化妝品配方
JP7493505B2 (ja)	2018-12-12	2024-05-31	ダウグローバルテクノロジーズエルエルシー	カルボシロキサンを有する多段ポリマーを含むパーソナルケア配合物
CN115010841B (zh) *	2022-07-20	2023-12-05	巩义市泛锐熠辉复合材料有限公司	一种改性气凝胶及其制备的保温涂料和制备方法

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US2532583A (en) *	1945-07-24	1950-12-05	Du Pont	Silicon-containing polymer preparation
US2982757A (en) *	1955-10-20	1961-05-02	Westinghouse Electric Corp	Styrenyl organosilicon monomers and polymers thereof
US2983719A (en) *	1956-02-20	1961-05-09	Bjorksten Res Lab Inc	Heat resistant elastomer
US3080348A (en) *	1958-04-23	1963-03-05	Dow Chemical Co	Copolymers of styrene and methyl methacrylate

1966
- 1966-08-10 US US571388A patent/US3467634A/en not_active Expired - Lifetime
1967
- 1967-08-02 GB GB35514/67A patent/GB1200756A/en not_active Expired
- 1967-08-04 CH CH1100667A patent/CH484210A/fr not_active IP Right Cessation
- 1967-08-07 ES ES343902A patent/ES343902A1/es not_active Expired
- 1967-08-07 NO NO169276A patent/NO125392B/no unknown
- 1967-08-07 BE BE702403D patent/BE702403A/xx not_active IP Right Cessation
- 1967-08-07 SE SE11194/67A patent/SE339752B/xx unknown
- 1967-08-10 NL NL6711065A patent/NL6711065A/xx unknown
- 1967-08-10 DE DE19671745341 patent/DE1745341A1/de active Pending

Also Published As

Publication number	Publication date
CH484210A (fr)	1970-01-15
BE702403A (fr)	1968-01-15
GB1200756A (en)	1970-08-05
NL6711065A (fr)	1968-02-12
SE339752B (fr)	1971-10-18
ES343902A1 (es)	1968-12-01
US3467634A (en)	1969-09-16
DE1745341A1 (de)	1971-09-09

Publication	Publication Date	Title
US3467634A (en)	1969-09-16	Organosilicon terpolymers
EP1396504B1 (fr)	2009-01-14	Macromonomère polyolefine, polymère greffé obtenu à partir de celui-ci et son utilisation
JPH0139445B2 (fr)	1989-08-21
JP6791615B2 (ja)	2020-11-25	紫外線架橋性組成物
JPH09324016A (ja)	1997-12-16	耐熱性メタクリル系樹脂およびその製造方法
US4593081A (en)	1986-06-03	Chain-transfer agents for emulsion polymerization and polymer products produced therewith
JP2018035225A (ja)	2018-03-08	メタクリル系樹脂
US7163992B2 (en)	2007-01-16	Methods for manufacturing a copolymer with a high yield by reacting a vinyl monomer and a macromonomer
JPS6390515A (ja)	1988-04-21	耐熱性樹脂組成物の製造方法
NO169276B (no)	1992-02-24	Piggingsmaskin
US2984650A (en)	1961-05-16	Clear styrene/acrylonitrile/methacrylonitrile terpolymers obtained by batch free-radical polymerization
JPS58217501A (ja)	1983-12-17	新規共重合体
US5756624A (en)	1998-05-26	Terpene copolymers
JPS61174209A (ja)	1986-08-05	共重合体の製造方法
JPS60123518A (ja)	1985-07-02	シリコ−ン系グラフト共重合体の製造方法
EP0794201B1 (fr)	2003-11-12	Matiere premiere destinee a la production d'une resine resistante a la chaleur, resine resistante a la chaleur et procede de production de cette resine
US10174145B1 (en)	2019-01-08	Methacrylic resin
KR920001354B1 (ko)	1992-02-11	규소함유 고분자화합물 및 그의 제조방법
JP2003040946A (ja)	2003-02-13	ポリオレフィン系グラフト共重合体の製造方法
JPH0696658B2 (ja)	1994-11-30	耐熱性樹脂組成物
Srivastava et al.	2002	Terpolymerization: A review
JP2010018690A (ja)	2010-01-28	アクリル共重合体の製造方法
JPH06220106A (ja)	1994-08-09	共重合体の製造法
JPH06199938A (ja)	1994-07-19	グルタルイミドコポリマーの製造方法と、その中間化合物
JPS61275314A (ja)	1986-12-05	共重合体の製造法