DE3535283C2 - - Google Patents
Info
- Publication number
- DE3535283C2 DE3535283C2 DE3535283A DE3535283A DE3535283C2 DE 3535283 C2 DE3535283 C2 DE 3535283C2 DE 3535283 A DE3535283 A DE 3535283A DE 3535283 A DE3535283 A DE 3535283A DE 3535283 C2 DE3535283 C2 DE 3535283C2
- Authority
- DE
- Germany
- Prior art keywords
- groups
- group
- polysiloxanes
- koh
- mol
- 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.)
- Expired - Fee Related
Links
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 91
- -1 polysiloxane Polymers 0.000 claims abstract description 80
- 238000000465 moulding Methods 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 229920000728 polyester Polymers 0.000 claims abstract description 16
- 230000000181 anti-adherent effect Effects 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 230000001588 bifunctional effect Effects 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 14
- 229920005989 resin Polymers 0.000 abstract description 12
- 239000011347 resin Substances 0.000 abstract description 12
- 230000008569 process Effects 0.000 abstract description 10
- 239000000654 additive Substances 0.000 abstract description 3
- 239000004922 lacquer Substances 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 22
- 238000007127 saponification reaction Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 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 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000010107 reaction injection moulding Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 238000012694 Lactone Polymerization Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 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
- 230000001960 triggered effect Effects 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4692—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2125/00—Compositions for processes using internal mould release agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2150/00—Compositions for coatings
- C08G2150/20—Compositions for powder coatings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Silicon Polymers (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853535283 DE3535283A1 (de) | 1985-10-03 | 1985-10-03 | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer |
| US06/913,302 US4812518A (en) | 1985-10-03 | 1986-09-30 | Polyester group containing polysiloxanes for lacquers and molding compositions |
| EP86113456A EP0217364B2 (de) | 1985-10-03 | 1986-10-01 | Lacke und Formmassen enthaltend polyestergruppenhaltige Polysiloxane |
| DE8686113456T DE3687617D1 (de) | 1985-10-03 | 1986-10-01 | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer. |
| AT86113456T ATE85062T1 (de) | 1985-10-03 | 1986-10-01 | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer. |
| ES86113456T ES2046166T5 (es) | 1985-10-03 | 1986-10-01 | Lacas y masas de moldeo con contenido de polisiloxanos que contienen grupos poliester. |
| CA000519658A CA1283493C (en) | 1985-10-03 | 1986-10-02 | Polyester group containing polysiloxanes for lacquers and molding compositions |
| JP61235458A JPH089700B2 (ja) | 1985-10-03 | 1986-10-02 | ラッカー |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853535283 DE3535283A1 (de) | 1985-10-03 | 1985-10-03 | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3535283A1 DE3535283A1 (de) | 1987-04-09 |
| DE3535283C2 true DE3535283C2 (enExample) | 1990-12-20 |
Family
ID=6282639
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853535283 Granted DE3535283A1 (de) | 1985-10-03 | 1985-10-03 | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer |
| DE8686113456T Expired - Lifetime DE3687617D1 (de) | 1985-10-03 | 1986-10-01 | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8686113456T Expired - Lifetime DE3687617D1 (de) | 1985-10-03 | 1986-10-01 | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4812518A (enExample) |
| EP (1) | EP0217364B2 (enExample) |
| JP (1) | JPH089700B2 (enExample) |
| AT (1) | ATE85062T1 (enExample) |
| CA (1) | CA1283493C (enExample) |
| DE (2) | DE3535283A1 (enExample) |
| ES (1) | ES2046166T5 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19847303A1 (de) * | 1998-10-14 | 2000-05-04 | Bosch Gmbh Robert | Sensorelement oder Aktorelement mit antiadhäsiver Oberflächenbeschichtung |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512676A (en) | 1987-09-03 | 1996-04-30 | The Boeing Company | Extended amideimide hub for multidimensional oligomers |
| US5705598A (en) | 1985-04-23 | 1998-01-06 | The Boeing Company | Polyester sulfone oligomers and blends |
| US5210213A (en) | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
| US5693741A (en) | 1988-03-15 | 1997-12-02 | The Boeing Company | Liquid molding compounds |
| US5516876A (en) | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| US5969079A (en) | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
| US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| US5610317A (en) | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| JPH0721050B2 (ja) * | 1988-05-27 | 1995-03-08 | 株式会社レグルス | ポリエステル樹脂及びその製造方法 |
| JPH0733427B2 (ja) * | 1988-10-05 | 1995-04-12 | 大日精化工業株式会社 | ポリウレタン系樹脂の製造方法 |
| DE3839937A1 (de) * | 1988-11-26 | 1990-05-31 | Henkel Kgaa | Gleitlack fuer elastomerteile |
| JPH02147688A (ja) * | 1988-11-29 | 1990-06-06 | Kansai Paint Co Ltd | 着氷防止組成物 |
| JPH02196862A (ja) * | 1989-01-26 | 1990-08-03 | Shin Etsu Chem Co Ltd | ラクトン変性シリコーン組成物及びそれを含有してなる化粧料又は艶出し材料 |
| US5084527A (en) * | 1989-02-23 | 1992-01-28 | Mitsubishi Rayon Co., Ltd. | Thermoplastic resin composition |
| JP2537395B2 (ja) * | 1989-03-15 | 1996-09-25 | 大日精化工業株式会社 | 磁気記録媒体 |
| JP2537396B2 (ja) * | 1989-03-15 | 1996-09-25 | 大日精化工業株式会社 | 磁気記録媒体 |
| US5177160A (en) * | 1989-05-31 | 1993-01-05 | Dow Corning Toray Silicone Co., Ltd. | Organopolysiloxane graft polyester and its manufacturing method |
| JPH0692481B2 (ja) * | 1989-06-02 | 1994-11-16 | 信越化学工業株式会社 | ポリラクトン変性オルガノポリシロキサン化合物 |
| DE4004628A1 (de) * | 1990-02-15 | 1991-08-22 | Beutelrock Geb Wehrmann Caroli | Mittel zum lackabweisenden beschichten von substraten |
| FR2658531B1 (fr) * | 1990-02-16 | 1992-04-30 | Alsthom Cge Alcatel | Vernis d'emaillage, procede de fabrication d'un tel vernis et fil conducteur emaille en faisant application. |
| DE4017075A1 (de) * | 1990-05-26 | 1991-11-28 | Basf Lacke & Farben | Lacke und verwendung dieser lacke als decklacke zur lackierung von automobilkarosserien |
| US5262492A (en) * | 1990-08-31 | 1993-11-16 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Siloxane-modified polyester resins and production processes thereof |
| DE4129413A1 (de) * | 1991-09-04 | 1993-03-11 | Tipp Ex Gmbh & Co Kg | Mehrschichtiges korrekturmaterial, verfahren zu der herstellung desselben und verwendung |
| US5260401A (en) * | 1992-02-19 | 1993-11-09 | Siltech Inc. | Terminal fluorine containing silicone polyester compounds |
| US5164471A (en) * | 1992-02-19 | 1992-11-17 | Siltech Inc. | Fluorine containing silanol polyester waxes |
| US5879671A (en) * | 1992-11-06 | 1999-03-09 | Dow Corning Corporation | Hair conditioning with blended silicones |
| JP3032673B2 (ja) * | 1993-11-10 | 2000-04-17 | 信越化学工業株式会社 | 合成樹脂含有塗料用改質剤 |
| JP3134638B2 (ja) * | 1993-12-03 | 2001-02-13 | 東洋インキ製造株式会社 | 磁気記録媒体 |
| JP3682874B2 (ja) * | 1994-09-01 | 2005-08-17 | 戸田工業株式会社 | 無機着色粒子粉末及びその製造法並びに該無機着色粒子粉末を用いた水系塗料 |
| DE4432260C1 (de) * | 1994-09-10 | 1995-06-22 | Herberts Gmbh | Überzugsmittel für kratzfeste und säurebeständige Deckschichten und deren Verwendung bei Verfahren zur Herstellung von Mehrschichtüberzügen |
| DE69623647T2 (de) * | 1995-12-22 | 2003-05-28 | Novartis Ag, Basel | Polyurethane aus polysiloxan-polyol-makromeren |
| EP0808881B1 (de) * | 1996-05-23 | 1999-09-22 | Ewald Dörken Ag | Beschichtung aus einem Pulverlack mit Antihaft-Effekt und Verfahren zu seiner Herstellung |
| EP0835897B1 (de) * | 1996-10-11 | 2001-11-28 | Goldschmidt AG | Siliconpoly(meth)acrylate, deren Herstellung und deren Verwendung in Beschichtungen |
| US6239212B1 (en) * | 1998-10-23 | 2001-05-29 | Basf Corporation. | Clearcoat composition and method for intercoat adhesion |
| DE19910975A1 (de) * | 1999-03-09 | 2000-09-21 | Goldschmidt Ag Th | Carbonatgruppen enthaltende, mit linearen Polyestern modifizierte Polysiloxane und ihre Verwendung als Zsatzstoffe in Beschichtungen |
| DE10048259A1 (de) * | 2000-09-29 | 2002-04-18 | Byk Chemie Gmbh | Beschichtungsmittel und polymere Formmassen mit anti-adhäsiven, schmutzabweisenden Eigenschaften |
| CN1268705C (zh) * | 2002-02-04 | 2006-08-09 | 巴斯福股份公司 | 防粘包装材料在化学品及食品包装上的应用 |
| DE10214436A1 (de) * | 2002-03-27 | 2003-10-23 | Blanco Gmbh & Co Kg | Giessmasse und daraus hergestellte Kunststoffformkörper |
| DE10227338B4 (de) * | 2002-06-19 | 2006-05-24 | Byk-Chemie Gmbh | Verwendung von Polyacrylat-modifizierten Polysiloxanen als Verlaufmittel in Beschichtungsmitteln |
| US7160959B2 (en) * | 2004-03-19 | 2007-01-09 | Ppg Industries Ohio, Inc. | Polymer additives for powder coatings |
| DE102004033060A1 (de) * | 2004-07-08 | 2006-01-26 | Byk-Chemie Gmbh | Polyestermodifizierte Polysiloxane und deren Verwendung als Additive für Thermoplaste, Formmassen und Lacke |
| DE102004035835A1 (de) * | 2004-07-23 | 2006-03-16 | Degussa Ag | Direkt metallisierbare Polyesterformmasse |
| US7651560B2 (en) | 2004-12-20 | 2010-01-26 | Koenig & Bauer Ag | Abhesive layer of cross-linked nanoparticles |
| TWI429688B (zh) * | 2005-02-14 | 2014-03-11 | Byk Chemie Gmbh | 經有機矽烷改質之聚矽氧烷及其用於表面改質作用之用途 |
| EP1942124A1 (en) * | 2006-12-22 | 2008-07-09 | DuPont Powder Coatings Ibérica, S.L. | Anti-graffity powder coating composition |
| CN101679786B (zh) * | 2007-05-01 | 2015-05-27 | 阿克佐诺贝尔国际涂料股份有限公司 | 含有羧基官能化有机聚硅氧烷的抗污涂料组合物 |
| CN102428145B (zh) * | 2009-03-18 | 2014-03-26 | 巴斯夫欧洲公司 | 改性的二氧化硅粒子和包含它们的防污聚合物组合物 |
| KR100962368B1 (ko) * | 2010-04-12 | 2010-06-10 | 엘지엠엠에이 주식회사 | 내스크래치성이 향상된 내충격 메틸메타크릴레이트 수지 조성물 |
| DE102010039168A1 (de) * | 2010-08-10 | 2012-02-16 | Schwering & Hasse Elektrodraht Gmbh | Elektroisolierlacke aus modifizierten Polymeren und daraus hergestellte elektrische Leiter mit verbesserter Gleitfähigkeit |
| DE102011003677B4 (de) | 2011-02-04 | 2015-09-24 | Schott Ag | Verbundstoff, Verfahren zu seiner Herstellung und Verwendung des Verbundstoffes |
| US8779012B2 (en) | 2011-06-21 | 2014-07-15 | Momentive Performance Materials Inc. | Biodegradable polyorganosiloxane demulsifier composition and method for making the same |
| JP2015502424A (ja) | 2011-11-14 | 2015-01-22 | ベーイプシロンカー ヘミー ゲゼルシャフト ミット ベシュレンクターハフトゥング | 塗装材料組成物および成形材料における変性ポリシロキサンの使用 |
| CN112218924B (zh) | 2018-06-05 | 2022-03-04 | 毕克化学有限公司 | 具有聚醚聚酯链段和聚硅氧烷链段的聚合物 |
| BR112021000476B1 (pt) * | 2018-08-02 | 2023-10-24 | Akzo Nobel Coatings International B.V | Composição de revestimento 2k, método de revestimento de um susbtrato e substrato revestido |
| CN112654676B (zh) * | 2018-09-10 | 2022-12-06 | 三洋化成工业株式会社 | 聚氨酯树脂组合物 |
| CN110003705A (zh) * | 2019-04-15 | 2019-07-12 | 广州市斯洛柯高分子聚合物有限公司 | 一种聚酯改性有机硅流平剂及其制备方法 |
| EP3772527A1 (de) * | 2019-08-08 | 2021-02-10 | Evonik Operations GmbH | Durchsichtige zusammensetzung |
| JP2023518571A (ja) * | 2020-03-24 | 2023-05-02 | ワッカー ケミー アクチエンゲゼルシャフト | ポリエステル－ポリシロキサンコポリマー含有組成物 |
| FI131665B1 (en) * | 2021-07-21 | 2025-09-03 | Metsae Spring Oy | Process for producing coated fiber products |
| CN114015054B (zh) * | 2021-12-09 | 2023-01-13 | 万华化学集团股份有限公司 | 苯酐有机硅二元醇、制备方法及热塑性苯硅聚氨酯胶黏剂 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2770631A (en) * | 1954-05-20 | 1956-11-13 | Dow Corning | Hydroxyester substituted siloxanes |
| US4076695A (en) * | 1977-02-07 | 1978-02-28 | Dow Corning Corporation | Silicone containing reaction injection molded polyurethanes |
| US4395527A (en) * | 1978-05-17 | 1983-07-26 | M & T Chemicals Inc. | Siloxane-containing polymers |
| JPS59149919A (ja) * | 1983-02-17 | 1984-08-28 | Toray Silicone Co Ltd | 反応射出成形体の製造方法 |
| DE3344911A1 (de) * | 1983-12-13 | 1985-06-13 | Bayer Ag, 5090 Leverkusen | Thermoplastische polysiloxan-polyester(carbonat)-blockcopolymere, ihre herstellung und verwendung |
| FR2565233B1 (fr) * | 1984-05-30 | 1986-09-12 | Rhone Poulenc Rech | Copolymere greffe de silicone et de polylactone lie par une liaison urethanne |
| DE3427208C2 (de) * | 1984-07-24 | 1986-06-05 | BYK-Chemie GmbH, 4230 Wesel | Lacke und Formmassen mit einem den Verlauf fördernden und die Gleitfähigkeit erhöhenden Gehalt an Siloxanen und die Verwendung solcher Siloxane als Zusatzmittel für Lacke und Formmassen |
| US4663413A (en) * | 1985-01-04 | 1987-05-05 | Thoratec Laboratories Corp. | Polysiloxane-polylactone block copolymers |
-
1985
- 1985-10-03 DE DE19853535283 patent/DE3535283A1/de active Granted
-
1986
- 1986-09-30 US US06/913,302 patent/US4812518A/en not_active Expired - Lifetime
- 1986-10-01 ES ES86113456T patent/ES2046166T5/es not_active Expired - Lifetime
- 1986-10-01 DE DE8686113456T patent/DE3687617D1/de not_active Expired - Lifetime
- 1986-10-01 AT AT86113456T patent/ATE85062T1/de not_active IP Right Cessation
- 1986-10-01 EP EP86113456A patent/EP0217364B2/de not_active Expired - Lifetime
- 1986-10-02 CA CA000519658A patent/CA1283493C/en not_active Expired - Lifetime
- 1986-10-02 JP JP61235458A patent/JPH089700B2/ja not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19847303A1 (de) * | 1998-10-14 | 2000-05-04 | Bosch Gmbh Robert | Sensorelement oder Aktorelement mit antiadhäsiver Oberflächenbeschichtung |
| DE19847303B4 (de) * | 1998-10-14 | 2006-11-30 | Robert Bosch Gmbh | Sensorelement mit antiadhäsiver Oberflächenbeschichtung |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3535283A1 (de) | 1987-04-09 |
| CA1283493C (en) | 1991-04-23 |
| EP0217364A3 (en) | 1989-07-05 |
| DE3687617D1 (de) | 1993-03-11 |
| ATE85062T1 (de) | 1993-02-15 |
| ES2046166T5 (es) | 1996-04-01 |
| EP0217364B1 (de) | 1993-01-27 |
| JPS62187772A (ja) | 1987-08-17 |
| EP0217364A2 (de) | 1987-04-08 |
| EP0217364B2 (de) | 1995-11-29 |
| US4812518A (en) | 1989-03-14 |
| ES2046166T3 (es) | 1994-02-01 |
| JPH089700B2 (ja) | 1996-01-31 |
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Legal Events
| Date | Code | Title | Description |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |