DE102005004639A1 - Modifiziertes Poly(meth)acrylat mit reaktiven ethylenischen Gruppen und dessen Verwendung - Google Patents
Modifiziertes Poly(meth)acrylat mit reaktiven ethylenischen Gruppen und dessen Verwendung Download PDFInfo
- Publication number
- DE102005004639A1 DE102005004639A1 DE102005004639A DE102005004639A DE102005004639A1 DE 102005004639 A1 DE102005004639 A1 DE 102005004639A1 DE 102005004639 A DE102005004639 A DE 102005004639A DE 102005004639 A DE102005004639 A DE 102005004639A DE 102005004639 A1 DE102005004639 A1 DE 102005004639A1
- Authority
- DE
- Germany
- Prior art keywords
- meth
- acrylate
- isocyanate
- synthetic resin
- urethane
- 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.)
- Ceased
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 99
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 239000000178 monomer Substances 0.000 title claims abstract description 44
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 42
- 239000000057 synthetic resin Substances 0.000 title claims abstract description 42
- 239000012948 isocyanate Substances 0.000 title claims abstract description 40
- 230000000379 polymerizing effect Effects 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 150000002513 isocyanates Chemical class 0.000 title claims description 10
- 239000011230 binding agent Substances 0.000 title claims description 7
- -1 isocyanate compound Chemical class 0.000 claims abstract description 55
- 239000002131 composite material Substances 0.000 claims abstract description 50
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 49
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 45
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 229920000193 polymethacrylate Polymers 0.000 claims abstract description 41
- 238000004132 cross linking Methods 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000004922 lacquer Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 24
- 239000003973 paint Substances 0.000 claims description 19
- 239000000945 filler Substances 0.000 claims description 16
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 239000000049 pigment Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 4
- 239000004971 Cross linker Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000007493 shaping process Methods 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 230000001747 exhibiting effect Effects 0.000 abstract 5
- 239000013543 active substance Substances 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 description 49
- 239000000126 substance Substances 0.000 description 22
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 238000001723 curing Methods 0.000 description 12
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 239000004926 polymethyl methacrylate Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 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 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000006750 UV protection Effects 0.000 description 3
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-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
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 206010053317 Hydrophobia Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 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 description 2
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-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
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011151 fibre-reinforced plastic Substances 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002986 polymer concrete Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XASGSDGLJNPIOL-UHFFFAOYSA-N 1,1-diisocyanato-3,3,5,5-tetramethylcyclohexane Chemical compound CC1(C)CC(C)(C)CC(N=C=O)(N=C=O)C1 XASGSDGLJNPIOL-UHFFFAOYSA-N 0.000 description 1
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 1
- GNQKHBSIBXSFFD-UHFFFAOYSA-N 1,3-diisocyanatocyclohexane Chemical compound O=C=NC1CCCC(N=C=O)C1 GNQKHBSIBXSFFD-UHFFFAOYSA-N 0.000 description 1
- AGJCSCSSMFRMFQ-UHFFFAOYSA-N 1,4-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=C(C(C)(C)N=C=O)C=C1 AGJCSCSSMFRMFQ-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- VFFFESPCCPXZOQ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.OCC(CO)(CO)CO VFFFESPCCPXZOQ-UHFFFAOYSA-N 0.000 description 1
- ZCHGODLGROULLT-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;propane-1,2-diol Chemical compound CC(O)CO.OCC(CO)(CO)CO ZCHGODLGROULLT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005004639A DE102005004639A1 (de) | 2005-02-01 | 2005-02-01 | Modifiziertes Poly(meth)acrylat mit reaktiven ethylenischen Gruppen und dessen Verwendung |
| PL06700673T PL1846461T3 (pl) | 2005-02-01 | 2006-01-11 | Zmodyfikowany poli(met)akrylan o reaktywnych grupach etylenowych i jego zastosowanie |
| AT06700673T ATE404592T1 (de) | 2005-02-01 | 2006-01-11 | Modifiziertes poly(meth)acrylat mit reaktiven ethylenischen gruppen und dessen verwendung |
| ES06700673T ES2312105T3 (es) | 2005-02-01 | 2006-01-11 | Poli(met)acrilato modificado con grupos etilenicos reactivos y su uso. |
| DE502006001329T DE502006001329D1 (de) | 2005-02-01 | 2006-01-11 | Modifiziertes poly(meth)acrylat mit reaktiven ethylenischen gruppen und dessen verwendung |
| US11/883,403 US20100093924A1 (en) | 2005-02-01 | 2006-01-11 | Modified Poly(meth)acrylate with Reactive Ethylenic Groups and Use Thereof |
| CA002596464A CA2596464A1 (en) | 2005-02-01 | 2006-01-11 | Modified poly(meth)acrylate with reactive ethylenic groups and use thereof |
| JP2007553488A JP2008528771A (ja) | 2005-02-01 | 2006-01-11 | 反応性エチレン基で修飾されたポリ（メタ）アクリレートおよびその使用 |
| PCT/EP2006/000188 WO2006081916A1 (de) | 2005-02-01 | 2006-01-11 | Modifiziertes poly(meth)acrylat mit reaktiven ethylenischen gruppen und dessen verwendung |
| EP06700673A EP1846461B1 (de) | 2005-02-01 | 2006-01-11 | Modifiziertes poly(meth)acrylat mit reaktiven ethylenischen gruppen und dessen verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005004639A DE102005004639A1 (de) | 2005-02-01 | 2005-02-01 | Modifiziertes Poly(meth)acrylat mit reaktiven ethylenischen Gruppen und dessen Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005004639A1 true DE102005004639A1 (de) | 2006-08-03 |
Family
ID=36097134
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005004639A Ceased DE102005004639A1 (de) | 2005-02-01 | 2005-02-01 | Modifiziertes Poly(meth)acrylat mit reaktiven ethylenischen Gruppen und dessen Verwendung |
| DE502006001329T Expired - Lifetime DE502006001329D1 (de) | 2005-02-01 | 2006-01-11 | Modifiziertes poly(meth)acrylat mit reaktiven ethylenischen gruppen und dessen verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502006001329T Expired - Lifetime DE502006001329D1 (de) | 2005-02-01 | 2006-01-11 | Modifiziertes poly(meth)acrylat mit reaktiven ethylenischen gruppen und dessen verwendung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20100093924A1 (https=) |
| EP (1) | EP1846461B1 (https=) |
| JP (1) | JP2008528771A (https=) |
| AT (1) | ATE404592T1 (https=) |
| CA (1) | CA2596464A1 (https=) |
| DE (2) | DE102005004639A1 (https=) |
| ES (1) | ES2312105T3 (https=) |
| PL (1) | PL1846461T3 (https=) |
| WO (1) | WO2006081916A1 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006038714A1 (de) * | 2006-08-18 | 2008-02-21 | Evonik Röhm Gmbh | Medienbeständige Lackharze |
| WO2008043486A1 (de) * | 2006-10-09 | 2008-04-17 | Ashland-Südchemie-Kernfest GmbH | Radikalische kalthärtung von auf modifizierten poly(meth)acrylaten mit reaktiven ethylenischen gruppen basierenden kunstharzen |
| WO2008043487A1 (de) * | 2006-10-09 | 2008-04-17 | Ashland-Südchemie-Kernfest GmbH | Radikalische kalthärtung von auf modifizierten poly(meth)acrylaten mit reaktiven ethylenischen gruppen basierenden kunstharzen |
| EP2862904A1 (en) | 2013-10-18 | 2015-04-22 | Samtastic Products GmbH | Polymeric material, article comprising said poymeric material and method for producing the same |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009036481A1 (de) | 2009-08-07 | 2011-02-10 | Nightec Gmbh & Co. Kg | Photolumineszierendes Granulat und Verfahren zu dessen Herstellung |
| KR101624213B1 (ko) | 2012-01-17 | 2016-05-25 | 디아이씨 가부시끼가이샤 | 활성 에너지선 경화형 수성 수지 조성물, 활성 에너지선 경화형 수성 도료, 및 당해 도료로 도장된 물품 |
| US10442963B1 (en) | 2015-12-22 | 2019-10-15 | McTron Technologies, LLC | Durable and hydrophobic polymeric binder and adhesive |
| EP3587526B1 (en) * | 2018-06-29 | 2022-02-16 | 3M Innovative Properties Company | Both sides coated automotive paint compatible liner for structural adhesive film |
| CN113185646A (zh) * | 2021-06-12 | 2021-07-30 | 湖南创瑾科技有限公司 | 导电3d打印材料及其制备方法 |
| WO2025248386A1 (en) * | 2024-05-31 | 2025-12-04 | Unilin, Bv | Acrylate coating composition and method for applying a coating layer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE35280E (en) * | 1981-04-28 | 1996-06-18 | Imperial Chemical Industries Plc | Copolymerization of unsaturated urethane monomers |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS532919B2 (https=) * | 1971-08-12 | 1978-02-01 | ||
| JPS524541A (en) * | 1975-06-30 | 1977-01-13 | Dainippon Toryo Co Ltd | Tentative protection of metal surfaces with ultraviolet-curing paint |
| JPH0786125B2 (ja) * | 1985-10-09 | 1995-09-20 | 日本ペイント株式会社 | 反応性微小樹脂粒子、その製法ならびに硬化組成物 |
| JPH11514622A (ja) * | 1995-11-03 | 1999-12-14 | デー エス エム エヌ．ヴェー． | 無溶剤、輻射線硬化性、光学ガラス繊維用のコーテイング組成物および無溶剤、輻射線硬化性、光学ガラス繊維用のコーテイング組成物の無溶剤式製造方法 |
-
2005
- 2005-02-01 DE DE102005004639A patent/DE102005004639A1/de not_active Ceased
-
2006
- 2006-01-11 US US11/883,403 patent/US20100093924A1/en not_active Abandoned
- 2006-01-11 PL PL06700673T patent/PL1846461T3/pl unknown
- 2006-01-11 ES ES06700673T patent/ES2312105T3/es not_active Expired - Lifetime
- 2006-01-11 DE DE502006001329T patent/DE502006001329D1/de not_active Expired - Lifetime
- 2006-01-11 AT AT06700673T patent/ATE404592T1/de active
- 2006-01-11 WO PCT/EP2006/000188 patent/WO2006081916A1/de not_active Ceased
- 2006-01-11 CA CA002596464A patent/CA2596464A1/en not_active Abandoned
- 2006-01-11 EP EP06700673A patent/EP1846461B1/de not_active Expired - Lifetime
- 2006-01-11 JP JP2007553488A patent/JP2008528771A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE35280E (en) * | 1981-04-28 | 1996-06-18 | Imperial Chemical Industries Plc | Copolymerization of unsaturated urethane monomers |
Non-Patent Citations (1)
| Title |
|---|
| US Re. 35280E |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006038714A1 (de) * | 2006-08-18 | 2008-02-21 | Evonik Röhm Gmbh | Medienbeständige Lackharze |
| WO2008043486A1 (de) * | 2006-10-09 | 2008-04-17 | Ashland-Südchemie-Kernfest GmbH | Radikalische kalthärtung von auf modifizierten poly(meth)acrylaten mit reaktiven ethylenischen gruppen basierenden kunstharzen |
| WO2008043487A1 (de) * | 2006-10-09 | 2008-04-17 | Ashland-Südchemie-Kernfest GmbH | Radikalische kalthärtung von auf modifizierten poly(meth)acrylaten mit reaktiven ethylenischen gruppen basierenden kunstharzen |
| EP2862904A1 (en) | 2013-10-18 | 2015-04-22 | Samtastic Products GmbH | Polymeric material, article comprising said poymeric material and method for producing the same |
| WO2015055316A1 (en) | 2013-10-18 | 2015-04-23 | Samtastic Products GmbH | Polymeric material, article comprising said polymeric material, and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1846461A1 (de) | 2007-10-24 |
| US20100093924A1 (en) | 2010-04-15 |
| JP2008528771A (ja) | 2008-07-31 |
| ATE404592T1 (de) | 2008-08-15 |
| WO2006081916A1 (de) | 2006-08-10 |
| ES2312105T3 (es) | 2009-02-16 |
| CA2596464A1 (en) | 2006-08-10 |
| EP1846461B1 (de) | 2008-08-13 |
| PL1846461T3 (pl) | 2009-04-30 |
| DE502006001329D1 (de) | 2008-09-25 |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8131 | Rejection |