GB2204050A - U-V curable resin composition for coating optical fibres - Google Patents
U-V curable resin composition for coating optical fibres Download PDFInfo
- Publication number
- GB2204050A GB2204050A GB08807184A GB8807184A GB2204050A GB 2204050 A GB2204050 A GB 2204050A GB 08807184 A GB08807184 A GB 08807184A GB 8807184 A GB8807184 A GB 8807184A GB 2204050 A GB2204050 A GB 2204050A
- Authority
- GB
- United Kingdom
- Prior art keywords
- resin composition
- ultraviolet
- curable resin
- ray curable
- composition according
- Prior art date
- 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.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 40
- 239000011248 coating agent Substances 0.000 title claims abstract description 9
- 238000000576 coating method Methods 0.000 title claims abstract description 9
- 230000003287 optical effect Effects 0.000 title description 7
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000013307 optical fiber Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 239000011593 sulfur Substances 0.000 claims abstract description 11
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000012991 xanthate Substances 0.000 claims abstract description 6
- 229960002447 thiram Drugs 0.000 claims abstract description 5
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 4
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012990 dithiocarbamate Substances 0.000 claims abstract description 3
- 230000002401 inhibitory effect Effects 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 8
- 239000004925 Acrylic resin Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 5
- -1 thiazole compound Chemical class 0.000 claims description 5
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- VJDVTCMMFZCKKG-UHFFFAOYSA-N 1,1-ditert-butylthiourea Chemical compound CC(C)(C)N(C(N)=S)C(C)(C)C VJDVTCMMFZCKKG-UHFFFAOYSA-N 0.000 claims description 2
- XVNPNGPNQJUMSL-UHFFFAOYSA-N 1-ethyl-1-phenylthiourea Chemical compound CCN(C(N)=S)C1=CC=CC=C1 XVNPNGPNQJUMSL-UHFFFAOYSA-N 0.000 claims description 2
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 claims description 2
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 claims description 2
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 claims description 2
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- GCFZPYZBEBXONO-UHFFFAOYSA-N benzyl N,N-dicyclohexylcarbamodithioate Chemical compound C1(CCCCC1)N(C(SCC1=CC=CC=C1)=S)C1CCCCC1 GCFZPYZBEBXONO-UHFFFAOYSA-N 0.000 claims description 2
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 claims description 2
- PGAXJQVAHDTGBB-UHFFFAOYSA-N dibutylcarbamothioylsulfanyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SSC(=S)N(CCCC)CCCC PGAXJQVAHDTGBB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- OFHMODDLBXETIK-UHFFFAOYSA-N methyl 2,3-dichloropropanoate Chemical compound COC(=O)C(Cl)CCl OFHMODDLBXETIK-UHFFFAOYSA-N 0.000 claims description 2
- WGARMULIELDQEH-UHFFFAOYSA-N n-cyclohexyl-1,3-benzothiazole-2-sulfinamide Chemical compound N=1C2=CC=CC=C2SC=1S(=O)NC1CCCCC1 WGARMULIELDQEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- HLZBIKHKXIJIHX-UHFFFAOYSA-N benzyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SCC1=CC=CC=C1 HLZBIKHKXIJIHX-UHFFFAOYSA-N 0.000 claims 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims 1
- 150000002898 organic sulfur compounds Chemical class 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 229920001296 polysiloxane Polymers 0.000 abstract description 3
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 abstract description 2
- 150000004659 dithiocarbamates Chemical class 0.000 abstract description 2
- 150000003585 thioureas Chemical class 0.000 abstract description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 abstract 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 abstract 1
- 230000005540 biological transmission Effects 0.000 description 4
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 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 2
- IAMASUILMZETHW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCC(O)OC1=CC=CC=C1 IAMASUILMZETHW-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- OYKPJMYWPYIXGG-UHFFFAOYSA-N 2,2-dimethylbutane;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(C)(C)C OYKPJMYWPYIXGG-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-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
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- POYODSZSSBWJPD-UHFFFAOYSA-N 2-methylprop-2-enoyloxy 2-methylprop-2-eneperoxoate Chemical compound CC(=C)C(=O)OOOC(=O)C(C)=C POYODSZSSBWJPD-UHFFFAOYSA-N 0.000 description 1
- VKVWJISNCFMYCZ-UHFFFAOYSA-N 2-phenoxyundecane-1,2-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCCCCCCCC(O)(CO)OC1=CC=CC=C1 VKVWJISNCFMYCZ-UHFFFAOYSA-N 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- PSGCQDPCAWOCSH-BREBYQMCSA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] prop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C=C)C[C@@H]1C2(C)C PSGCQDPCAWOCSH-BREBYQMCSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- SNBMGLUIIGFNFE-UHFFFAOYSA-N benzyl n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)SCC1=CC=CC=C1 SNBMGLUIIGFNFE-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XWNVSPGTJSGNPU-UHFFFAOYSA-N ethyl 4-chloro-1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1Cl XWNVSPGTJSGNPU-UHFFFAOYSA-N 0.000 description 1
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/44—Mechanical structures for providing tensile strength and external protection for fibres, e.g. optical transmission cables
- G02B6/4401—Optical cables
- G02B6/4429—Means specially adapted for strengthening or protecting the cables
- G02B6/44384—Means specially adapted for strengthening or protecting the cables the means comprising water blocking or hydrophobic materials
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
Abstract
An ultraviolet-ray curable resin composition, comprising a sulfur-containing organic compound capable of inhibiting the generation of hydrogen is useful as a coating material of an optical fiber. The resin composition may comprise a urethane acrylate, epoxyacrylate silicone acrylate or trimethylol propane triacrylate together with N-vinylpyrrolidone and tris (2-acryloxyethyl) isocyanurate. Specified sulfur-containing compounds include certain benzothiazole compounds, thiuram mono-, di- and hexasulfides, thioureas, dithiocarbamates and xanthates.
Description
ULTRAVIOLET-RAY CURABLE RESIN COMPOSITION
Optical fibers comprise a core body (comprising a core and a cladding) formed by drawing glass or plastic into a fiber having a core/sheath structure and a protective layer having a refractive index different from that of the core body and formed on the outer surface of the core body. The light is transmitted from one end of the optical fiber to the other end thereof through the core body without undergoing scattering.
The optical fibers are used in an optical communication technique in virtue of this property.
The protective layers of the optical fibers usually comprise a primary coating layer (soft layer) formed in direct contact with the outer surface of the core body and a secondary coating layer (hard layer) formed thereon. These layers usually comprise a synthetic resin composition such as an ultraviolet-ray curable resin composition.
The ultraviolet-ray curable resin composition comprises, for example, an acrylic oligomer, an acrylic monomer, a photopolymerization initiator, and so forth.
However, hydrogen gas which diffuses into quartz glass or plastic exerts a significant influence on the optical transmission loss of the optical fiber under ordinary conditions. For example, hydrogen gas which has diffused into quartz glass is held in lattice defects of the main components of the glass, such as
SiC2 or GeO2, to form a hydroxyl group (OH) to thereby increase the optical transmission loss of the optical fiber. Therefore, when a resin composition which generates hydrogen gas is used as a coating material or the optical fiber, the optical transmission loss of the optical fiber coated with the resin composition is increased disadvantageously.
The present invention provides an ultravioletray curable resin composition useful as a coating material for optical fibers which contains a sulfurcontaining organic compound so as to inhibit the generation of hydrogen gas therefrom and to prevent the increase of the optical transmission loss.
The ultraviolet-ray curable resin composition of the present invention is characterized by containing a sulfur-containing organic compound.
The sulfur-containing organic compound usable in the present invention comprises one or more compounds selected from the group consisting of organic compounds of the following formulae (I) to (V), and xanthates.
wherein X represents H or an alkyl group or a residue of an amine such as cyclohexylamine, t-butylamine, morpholine or dicyclohexylamine,
wherein X represents H, an alkyl group or a residue of an amine such as cyclohexylamine, t-butylamine, morpholine or dicyclohexylamine, and X' represents a halogen or an alkoxy group having 1 to 8 carbon atoms,
wherein R1 to R4 each represent an alkyl group having 1 to 8 carbon atoms, usually 1 to 4 carbon atoms, or R1 and
R2 or R3 and R4 may form together a ring, and x represents an integer of 1 to 6,
wherein R5 and R6 each represent H or an alkyl or phenyl group, and
wherein R7 and R8 each represent an alkyl, arall cr aryl group and Rg is the same as R7 or RB or it represents a residue of an organic compound such as an amino group.
Among the sulfur-containing organic compounds of the present invention, preferably at least one compound selected from the group consisting of the organic compounds of the above formulae (I) to (V) and xanthates is incorporated in the resin composition used fcr coating the optical fibers.
Examples of the above-described sulfurcontaining organic compounds according to the present invention include the following ones: thiazoles of the formula (I):
mercaptobenzothiazole, dibenzothiazole disulfide, N-cyclohexylbenzothiazylsulfenamide,
N-oxydiethylenebenzothiazylsulfenamide, t-butylbenzothiazylsulfenamide and dicyclohexylbenzothiazylsulfenamide.
thiazoles of the formula (II) wherein the benzene nucleus is substituted:
compounds of the formula (I) wherein the benzene nucleus of the thiazole ring is substituted with at least one of halogen atoms such as C1 or Br and alkoxy groups having 1 to 8 carbon atoms, tiras of the formula (III):
tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetrabutylthiuram disulfide, tetramethylthiuram monosulfide and dipentamethylenethiuram hexasulfide, thioureas of the formula (IV):
thiourea, dimethylthiourea, diethylthiourea, di-t-butylthiourea, diphenylthiourea and ethylphenylthiourea, dithiocarbamates of the formula (V):
thiocarbamates, N'-morpholinomethyl dicyclohexyldithiocarbamate, 9-anthrylmethyl diethyldithiocarbamate, benzyl dicyclohexyldithiocarbamate and benzyl N,N-diethyldithiocarbamate.
xanthates of the following formula: RlnOCSSR11 wherein R10 represents an alkyl or aryl group and R11 represents also an alkyl or aryl group, such as ethylxanthogenylbenzyl, propylxanthogenylbenzyl, t-butylxanthogenylisopropyl, 2-ethylhexylxanthogenylbenzyl, and benzylxanthogenylisopropyl.
The sulfur-containing organic compounds are selected in consideration of their compatibility with the polymer used, dispersibility and stability to staining.
They can be used either alone or in the form of a mixture of two or more of them or a mixture with another compound so as to exhibit a synergistic effects.
The resin constituting the ultraviolet-ray curable resin composition of the present invention is not particularly limited and it may be any of resins which are curable by ultraviolet rays. The resins include, for example, urethane acrylate resin, acrylic resin, epoxy acrylate resin and unsaturated ester resins.
It is preferred to use urethane acrylate or acrylic resin for coating the optical fibers.
The amount of the sulfur-containing organic compound in the ultraviolet-ray curable resin composition of the present invention is in the range of 0.01 to 3.0 parts by weight, preferably 0.1 to less than 2.0 part by weight, for 100 parts by weight of the resin composition.
When the amount of the sulfur-containing organic compound is less than 0.01 part by weight, the effect of preventing the amount of hydrogen generated cannot be obtained and, on the contrary, when it exceeds 3.0 parts by weight, not only the amount of hydrogen generated becomes constant but also the photo-curing velocity of the resin composition is reduced unfavorably.
As an example of UV-curable resin composition used in the present invention; there is a resin composition which comprises 100 parts by weight of the resin such as urethane acrylate (urethane methacrylate), epoxy acrylate (epoxy methacrylate), silicone acrylate (silicone methacrylate) or trimethylpropane triacrylate, 1 to 40 parts by weight of N-vinyl pyrrolidone, 10 to 40 parts by weight of tris(2-acryloxyethyl)isocyanurate, 0.5 to 10 parts by weight of optical polymerization initiator and appropriate amounts of reactive diluent.
As reactive diluents, various mono acrylates are used, which include 2-ethylhexyl acrylate, lauryl acrylate, 2-hydroxyethyl acrylate, 2-methoxyethyl acrylate, 2-ethoxyethyl acrylate, 2-butoxyethyl acrylate, 2-phenoxyethyl acrylate, dicyclopentanyl acrylate, dicyclopentanyloxyethyl acrylate, isobornyl acrylate, tetrahydrofurfuryl acrylate, phenoxydiethyleneglycol acrylate, and nonylphenoxyethyleneglycol acrylate.
Especially, phenoxyethyl acrylate, isobornyl acrylate, phenoxydiethyleneglycol acrylate and dicyclopentanyloxyethyl acrylate. These can be alone or as a combination of two or more. The proportion of these monoacrylates is preferably less than 60 parts by weight per 100 parts by weight of urethane acrylate for the purpose of not impairing characteristic properties such as elastic modulus, elongation, and water-absorption causing from uethane acrylate and tris (2-acryloxyethyl) isocyanulate.
As photopolymerization initiator, radical cleavage type, hydrogen-abstraction type and other any type of initiators can be used. For example, 2,2dimethoxy-2-phenylacetophenone, l-hydroxycyclohexylphenyl ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, 2-hydroxy-2methylpropiophenone, benzil, benzophenone, 2-methyl[4(methylthio)phenyl]-2-morpholino-1-propanone, 2-methylanthraquinone, 2,4-diethylthioxanthone and the like are effectively used. The amount to be used less than 0.5 - 10% by weight, preferably less than 1 - 5% by weight.
Furthermore, the compositions according to the present invention may contain various types of additives, such as antioxidants, polymerization inhibitors, levelling agents, antifoaming agents and the like.
The following examples will further illustrate the present invention.
In the following examples, the amount of hydrogen generated from the resin composition was determined by the following evaluation test method:
Evaluation test method for hydrogen generated:
A resin composition was applied to a glass plate to form a film having a thickness of 200 to 250 um.
The coating film thus formed on the glass was irradiated with a light of 400 mJ/cm by means of a metal halide lamp (80 W/cm) to cure the film and thus to prepare a sample.
1 to 2 g of the sample was accurately weighed and placed in a vial having a known volume. The vial was left to stand in a dryer at 1000 C for 24 h. The headspace gas in the vial was introduced into a gas chromatograph by means of a gas-tight syringe. The determination was conducted by the absolute calibration method.
Example 1:
The amounts of hydrogen generated from resin composition Nos. 1 to 13 comprising components shown in
Table 1 (parts by weight) were determined to obtain the results shown in Table 1.
It is apparent from Table 1 that the resin composition Nos. 2 to 13 of the present invention containing a sulfur-containing organic compound generated a far reduced amount of hydrogen as compared with the composition No. 1.
Example 2:
The amounts of hydrogen generated from resin composition Nos. 14 to 22 comprising components shown in
Table 2 were determined in the same manner as that of
Example 1. The results are also shown in Table 2. Table 1
Resin composition: No. 1 No. 2 No. 3 No. 4 No. 5 No. 6 No. 7 No. 8 No. 9 No. 10 No. 11 No. 12 No. 13 Urethane acrylate* 70 70 70 70 70 70 70 70 70 70 70 70 70 N-Vinylpyrrolidone 10 10 10 10 10 10 10 10 10 10 10 10 10 Phenoxyethyl acrylate 15 15 15 15 15 15 15 15 15 15 15 15 15 1-Hydroxycyclohexyl phenyl ketone 5 5 5 5 5 5 5 5 5 5 5 5 5 2-N,N-Diethylthiocarbamoylthiobenzothiazole - 0.1 0.5 1.0 2.0 - - - - - - - Benzyl-N,N-diethyldithiocarbamate - - - - - - - - - 0.1 1.0 - N'-morpholinomethyldicyclohexyldicarbamate - - - - - - - - - - - 0.1 1.0 2-Mercaptobenzothiazole - - - - - 0.1 1.0 - - - - - Tetramethylthiuram disulfide - - - - - - - 0.1 1.0 - - - Amount of hydrogen 12.0 1.60 1.31 1.03 1.03 0.92 1.79 1.05 4.70 1.09 2.13 1.30 1.78 1.12 generated ( l/g) Notes: * urethane acrylate 2HEA/TDI/PPTG-4000/TDI/2HEA 2HEA: 2-hydroxyethyl acrylate TDI: tolylene diisocyanate
PPTG: polytetramethylene glycol (average molecular weight: 4000) Table 2
No.
No. 14 15 16 17 18 19 20 21 22 urethane acrylate 50 50 50 50 50 50 50 50 50 POA 12 12 12 12 12 12 12 12 12 R-604 7 7 7 7 7 7 7 7 7 FA-731A 20 20 20 20 20 20 20 20 20 N-VP 6 6 6 6 6 6 6 6 6 QM-589 5 5 5 5 5 5 5 5 5 0.1 SH 0.1 1.0 - - - - - - \ N C1gN > SH - - 0.1 1.0 ~ ~ | ~ E t-01 -SH 0.1 1.0 gS > ~ ~ | ~ 0 -1 | 1- 0 ~ - - - - | | j SN - - - - - - 1.0 j Br C3H7 4 N - , - - - - - - 11.0 C,H,O/\ 7 1-184 5 5 5 5 5 5 5 5 5 Amount of H2 generated 2.5 0.6 1.8 0.4 2.10 0.6 0.5 0.8 17.8 (a79) Young's modulus (kg/mm2) 40.8 36.6 41.9 40.4 41.2 34.2 39.1 35.0 40.7 aster curing (100 'nJ/cm2) 2 Yc'ng's modulus (kg/mm2) 48.6 50.9 46.0 47.6 6.5 48.3 a=.er curing (1000 mJ/cm2) ) Young's modulus ratio 100/1000 mJ/c'n2 (%) 84.9 79.3 85.3 83.1 80.9 74.4 82.1 75.2 84.3 solubility * | - x - 0 - 0 0 | o ~ * Solubility: o: heating unnecessary for dissolution
x: heating necessary for dissolution
It is apparent from Table 2 that the amounts of hydrogen generated from resin composition Nos. 12 to 19 of the present invention are far smaller than those of resin composition No. 20.
Claims (15)
1. An ultraviolet-ray curable resin composition containing an effective amount of a sulfur-containing organic compound capable of inhibiting the generation of hydrogen.
2. An ultraviolet-ray curable resin composition according to claim 1, wherein the sulfur-containing organic compound is at least one compound selected from the group consisting of organic compounds of the following formulae (I) to (V), and xanthates:
wherein X represents H, an alkyl group or a residue of an amine such as cyclohexylamine, t-butylamine, morpholine or dicyclohexylamine,
wherein X represents H, an alkyl group or a residue of an amine such as cyclohexylamine, t-butylamine, morpholine or dicyclohexylamine, and X' represents a halogen or an alkoxy group having 1 to 8 carbon atoms,
wherein R1 to R4 each represent an alkyl group having 1 to 8 carbon atoms, usually 1 to 4 carbon atoms, or R1 and R2 or R3 and R4 may form together a ring, and x represents an integer of 1 to 6,
wherein R5 and R6 each represent H or an alkyl or phenyl group, and
wherein R7 and RB each represent an alkyl, aralkyl or aryl group, and Rg is the same as R7 or R8 or it represents an organic residue such as an amino group.
3. An ultraviolet-ray curable resin composition according to claim 2, wherein the thiazole of the formula (I) is any of mercaptobenzothiazole, dibenzothiazole disulfide, N-cyclohexylbenzothiazylsulfenamide, N-oxydiethylenebenzothiazylsulfenamide, t-butylbenzothiazylsulfenamide and dicyclohexylbenzothiazylsulfenamide.
4. An ultraviolet-ray curable resin composition according to claim 2, wherein the thiazole of the formula (II) having a substituted benzene nucleus is a thiazole compound of the formula (I) in which the benzene nucleus is substituted with at least one atomic group selected from the group consisting of halogen atoms and alkoxy groups having 1 to 8 carbon atoms.
6. An ultraviolet-ray curable resin composition according to claim 2, wherein the thiuram of the formula (III) is any of tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetrabutylthiuram disulfide, tetramethylthiuram monosulfide and dipentamethylenethiuram hexasulfide.
6. An ultraviolet-ray curable resin composition according to claim 2, wherein the thiourea of the formula (IV) is any of thiourea, dimethylthiourea, diethylthiourea, di-t-butylthiourea, diphenylthiourea and ethylphenylthiourea.
7. An ultraviolet-ray curable resin composition according to claim 2, wherein the dithiocarbamate of the formula (V) is any of benzyl N,N-dimethyldithiocarbamate,
N'-morpholinomethyl dicyclohexyldithiocarbamate, 9-anthrylmethyl diethyldithiocarbamate, benzyl dicyclohexyldithiocarbamate and benzyl N,Ndiethyldithiocarbamate.
8. An ultraviolet-ray curable resin composition according to claim 2, wherein the xanthate is any of ethylxanthogenylbenzyl, propylxanthogenylbenzyl, t-butylxanthogenylisopropyl, 2-ethylhexylxanthogenylbenzyl and benzylxanthogenylisopropyl.
9. An ultraviolet-ray curable resin composition according to claim 1, wherein the ultraviolet-ray curable resin is at least one resin selected from the group consisting of urethane acrylate resin, acrylic resin, epoxy acrylate resin and unsaturated ester resin.
10. An ultraviolet-ray curable resin composition according to claim 1, wherein the amount of the organosulfur compound is in the range of 0.01 to 3.0 parts by weight for 100 parts by weight of the resin composition.
11. An ultraviolet-ray curable resin composition according to claim 1, wherein the composition is a resin used for coating optical fibers.
12. An ultraviolet-ray curable resin composition according to claim 1, wherein the composition is a resin used for coating optical fibers comprising a glass core body.
13. An ultraviolet-ray curable resin composition substantially as hereinbefore described.
14. A method of producing an ultraviolet-ray curable resin composition substantially as hereinbefore described.
15. Any novel integer or step, or combination of integers or steps, hereinbefore described, irrespective of whether the present claim is within the scope of, or relates to the same or a different invention from that of, the preceding claims.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7750287 | 1987-04-01 | ||
| JP62296051A JPS6426672A (en) | 1987-04-01 | 1987-11-26 | Ultraviolet-curing type resin composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8807184D0 GB8807184D0 (en) | 1988-04-27 |
| GB2204050A true GB2204050A (en) | 1988-11-02 |
| GB2204050B GB2204050B (en) | 1991-04-24 |
Family
ID=26418577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8807184A Expired - Lifetime GB2204050B (en) | 1987-04-01 | 1988-03-25 | Optical fibre coated with an ultraviolet-ray curable resin composition |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS6426672A (en) |
| KR (1) | KR960007612B1 (en) |
| GB (1) | GB2204050B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0813080A2 (en) * | 1996-06-10 | 1997-12-17 | Sumitomo Electric Industries, Ltd. | Optical fiber grating and method of manufacturing the same |
| US6004675A (en) * | 1991-09-03 | 1999-12-21 | Sumitomo Electric Industries, Ltd. | Optical glass fiber |
| WO2002022688A2 (en) * | 2000-09-18 | 2002-03-21 | Rhodia Chimie | Method for block polymer synthesis by controlled radical polymerisation in the presence of a disulphide compound |
| US6395393B1 (en) * | 1997-02-28 | 2002-05-28 | The Furukawa Electric Co., Ltd. | Optical fiber core wire binder and optical fiber unit |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB585179A (en) * | 1943-08-21 | 1947-01-31 | Ici Ltd | Photopolymerisation process |
| GB586297A (en) * | 1943-10-06 | 1947-03-13 | Du Pont | Improvements in or relating to the photopolymerisation of unsaturated organic compounds |
| GB771148A (en) * | 1954-07-22 | 1957-03-27 | Du Pont | Photopolymerizable compositions and the polymerization thereof |
| GB1116033A (en) * | 1966-05-23 | 1968-06-06 | Agfa Gevaert Nv | Photopolymerisation of ethylenically unsaturated organic compounds |
| GB1420888A (en) * | 1973-03-16 | 1976-01-14 | Ici America Inc | Photopolymerization of ethylenically unsaturated organic compounds |
| US3982942A (en) * | 1973-03-16 | 1976-09-28 | Ici United States Inc. | Photopolymerization of ethylenically-unsaturated organic compounds |
| EP0114982A2 (en) * | 1982-12-28 | 1984-08-08 | DeSOTO, INC. | Topcoats for buffer-coated optical fiber |
| EP0116140A1 (en) * | 1982-12-10 | 1984-08-22 | DeSOTO, INC. | Strippable coatings for optical fiber |
| US4511209A (en) * | 1982-02-24 | 1985-04-16 | Ensign-Bickford Industries, Inc. | Composition having improved optical qualities |
| US4587200A (en) * | 1983-06-06 | 1986-05-06 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition comprising an acridine and a heterocyclic thiol compound as a photopolymerization initiator and a photographic process using said photopolymerizable composition |
| EP0201903A2 (en) * | 1985-05-13 | 1986-11-20 | Mitsubishi Rayon Co., Ltd. | Photopolymerizable composition |
| EP0243605A2 (en) * | 1986-02-27 | 1987-11-04 | Dainippon Ink And Chemicals, Inc. | Fluorine-containing resin composition having a low refractive index |
-
1987
- 1987-11-26 JP JP62296051A patent/JPS6426672A/en active Pending
-
1988
- 1988-03-25 GB GB8807184A patent/GB2204050B/en not_active Expired - Lifetime
- 1988-03-30 KR KR1019880003485A patent/KR960007612B1/en active IP Right Grant
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB585179A (en) * | 1943-08-21 | 1947-01-31 | Ici Ltd | Photopolymerisation process |
| GB586297A (en) * | 1943-10-06 | 1947-03-13 | Du Pont | Improvements in or relating to the photopolymerisation of unsaturated organic compounds |
| GB771148A (en) * | 1954-07-22 | 1957-03-27 | Du Pont | Photopolymerizable compositions and the polymerization thereof |
| GB1116033A (en) * | 1966-05-23 | 1968-06-06 | Agfa Gevaert Nv | Photopolymerisation of ethylenically unsaturated organic compounds |
| GB1420888A (en) * | 1973-03-16 | 1976-01-14 | Ici America Inc | Photopolymerization of ethylenically unsaturated organic compounds |
| US3982942A (en) * | 1973-03-16 | 1976-09-28 | Ici United States Inc. | Photopolymerization of ethylenically-unsaturated organic compounds |
| US4511209A (en) * | 1982-02-24 | 1985-04-16 | Ensign-Bickford Industries, Inc. | Composition having improved optical qualities |
| EP0116140A1 (en) * | 1982-12-10 | 1984-08-22 | DeSOTO, INC. | Strippable coatings for optical fiber |
| EP0114982A2 (en) * | 1982-12-28 | 1984-08-08 | DeSOTO, INC. | Topcoats for buffer-coated optical fiber |
| US4587200A (en) * | 1983-06-06 | 1986-05-06 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition comprising an acridine and a heterocyclic thiol compound as a photopolymerization initiator and a photographic process using said photopolymerizable composition |
| EP0201903A2 (en) * | 1985-05-13 | 1986-11-20 | Mitsubishi Rayon Co., Ltd. | Photopolymerizable composition |
| EP0243605A2 (en) * | 1986-02-27 | 1987-11-04 | Dainippon Ink And Chemicals, Inc. | Fluorine-containing resin composition having a low refractive index |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6004675A (en) * | 1991-09-03 | 1999-12-21 | Sumitomo Electric Industries, Ltd. | Optical glass fiber |
| EP0813080A2 (en) * | 1996-06-10 | 1997-12-17 | Sumitomo Electric Industries, Ltd. | Optical fiber grating and method of manufacturing the same |
| EP0813080A3 (en) * | 1996-06-10 | 1998-08-26 | Sumitomo Electric Industries, Ltd. | Optical fiber grating and method of manufacturing the same |
| US6395393B1 (en) * | 1997-02-28 | 2002-05-28 | The Furukawa Electric Co., Ltd. | Optical fiber core wire binder and optical fiber unit |
| WO2002022688A2 (en) * | 2000-09-18 | 2002-03-21 | Rhodia Chimie | Method for block polymer synthesis by controlled radical polymerisation in the presence of a disulphide compound |
| FR2814168A1 (en) * | 2000-09-18 | 2002-03-22 | Rhodia Chimie Sa | PROCESS FOR THE SYNTHESIS OF BLOCK POLYMERS BY CONTROLLED RADICAL POLYMERIZATION IN THE PRESENCE OF A DISULFIDE COMPOUND |
| WO2002022688A3 (en) * | 2000-09-18 | 2002-06-20 | Rhodia Chimie Sa | Method for block polymer synthesis by controlled radical polymerisation in the presence of a disulphide compound |
| US6916884B2 (en) | 2000-09-18 | 2005-07-12 | Rhodia Chimie | Method for block polymer synthesis by controlled radical polymerization in the presence of a disulphide compound |
Also Published As
| Publication number | Publication date |
|---|---|
| KR960007612B1 (en) | 1996-06-07 |
| JPS6426672A (en) | 1989-01-27 |
| GB2204050B (en) | 1991-04-24 |
| GB8807184D0 (en) | 1988-04-27 |
| KR880012688A (en) | 1988-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940325 |