DE3329877C2 - - Google Patents
Info
- Publication number
- DE3329877C2 DE3329877C2 DE3329877A DE3329877A DE3329877C2 DE 3329877 C2 DE3329877 C2 DE 3329877C2 DE 3329877 A DE3329877 A DE 3329877A DE 3329877 A DE3329877 A DE 3329877A DE 3329877 C2 DE3329877 C2 DE 3329877C2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- groups
- general formula
- hydrophobic
- abhesive
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 24
- -1 reactive thinners Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 6
- 229920000642 polymer Polymers 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002466 imines Chemical class 0.000 claims description 5
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001925 cycloalkenes Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000003949 imides Chemical class 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 150000001361 allenes Chemical class 0.000 claims description 3
- 125000005375 organosiloxane group Chemical group 0.000 claims description 3
- 150000004291 polyenes Chemical class 0.000 claims description 3
- 150000004756 silanes Chemical class 0.000 claims description 3
- 150000004819 silanols Chemical class 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 241001120493 Arene Species 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000003377 silicon compounds Chemical class 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 6
- 239000004014 plasticizer Substances 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000012188 paraffin wax Substances 0.000 description 13
- 238000001723 curing Methods 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000006068 polycondensation reaction Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000006384 oligomerization reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- WFWOOWWOUDZVSA-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl) prop-2-enoate Chemical compound CC(C)(O)C(C)(C)OC(=O)C=C WFWOOWWOUDZVSA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000010559 graft polymerization reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- XTUXVDJHGIEBAA-BQYQJAHWSA-N (e)-3,4-dimethylhex-3-ene Chemical compound CC\C(C)=C(/C)CC XTUXVDJHGIEBAA-BQYQJAHWSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- SYQIWVMFOAHDMK-UHFFFAOYSA-N 2,2,3,3-tetramethyloxirane Chemical compound CC1(C)OC1(C)C SYQIWVMFOAHDMK-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- QOAGMYDHXIIWPW-UHFFFAOYSA-N 2,3,4,5,6,7-hexamethyloct-1-ene Chemical compound CC(C)C(C)C(C)C(C)C(C)C(C)=C QOAGMYDHXIIWPW-UHFFFAOYSA-N 0.000 description 1
- BHGNYYIOYPFWKC-UHFFFAOYSA-N 2,3,4,5-tetramethylhexane Chemical compound CC(C)C(C)C(C)C(C)C BHGNYYIOYPFWKC-UHFFFAOYSA-N 0.000 description 1
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 1
- LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 1
- AYQOFYMBBCZHFO-UHFFFAOYSA-N 2-(2,3,3-trimethyloxiran-2-yl)propanal Chemical compound O=CC(C)C1(C)OC1(C)C AYQOFYMBBCZHFO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XAJOPMVSQIBJCW-UHFFFAOYSA-N 3-penten-1-yne Chemical compound CC=CC#C XAJOPMVSQIBJCW-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000012958 Amine synergist Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000010471 Markovnikov's rule Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000007075 allylic rearrangement reaction Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 229940009827 aluminum acetate Drugs 0.000 description 1
- 239000011952 anionic catalyst Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 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
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011093 chipboard Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012967 coordination catalyst Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000008642 heat stress Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical class OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
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- C09J2423/005—Presence of polyolefin in the release coating
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Priority Applications (20)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833329877 DE3329877A1 (de) | 1983-08-18 | 1983-08-18 | Hydrophobe und/oder abhaesive masse, reaktiver verduenner und weichmacher und deren verwendung |
DE19833347861 DE3347861A1 (de) | 1983-08-18 | 1983-08-18 | Formmassen |
IT22325/84A IT1196227B (it) | 1983-08-18 | 1984-08-13 | Massa idrofoba e/o antiadesiva,diluente reattivo,plastificante e suo impiego |
CA000460896A CA1275204C (en) | 1983-08-18 | 1984-08-13 | Polymeric hydrocarbon abhesive and repellant compositions |
ES535131A ES535131A0 (es) | 1983-08-18 | 1984-08-14 | Procedimiento de obtencion de compuestos hidrofobicos. |
AT90114969T ATE122691T1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhäsive masse, reaktive verdünner, weichmacher und deren verwendung. |
EP90114969A EP0408085B1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhäsive Masse, reaktive Verdünner, Weichmacher und deren Verwendung |
AT84903165T ATE61597T1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhaesive masse, reaktive verduenner, weichmacher und deren verwendung. |
PCT/DE1984/000169 WO1985000820A1 (en) | 1983-08-18 | 1984-08-17 | Hydrophobic and/or antiadhesive masses, reactive diluents, plasticizer and utilization thereof |
BR8407024A BR8407024A (pt) | 1983-08-18 | 1984-08-17 | Massa hidrofoba e/ou anti-acesiva,diluentes reativos,plastificantes e sua utilizacao |
DE3486389T DE3486389D1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhäsive Masse, reaktive Verdünner, Weichmacher und deren Verwendung. |
JP59503251A JPS61500020A (ja) | 1983-08-18 | 1984-08-17 | 疎水性及び/又は剥離性物質、反応希釈剤、可塑剤及びそれらの使用 |
AU33189/84A AU582547B2 (en) | 1983-08-18 | 1984-08-17 | Hydrophobic and/or antiadhesive masses, reactive diluents, plasticizer and utilization thereof |
EP84903165A EP0153375B1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhäsive masse, reaktive verdünner, weichmacher und deren verwendung |
DE8484903165T DE3484280D1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhaesive masse, reaktive verduenner, weichmacher und deren verwendung. |
DK172185A DK172185D0 (da) | 1983-08-18 | 1985-04-17 | Hydrophobe og/eller abhesive materialer, reaktive fortyndingsmidler,plastificeringsmidler og anvendelsen af disse |
FI851531A FI72326C (fi) | 1983-08-18 | 1985-04-17 | Hydrofoba och/eller abhesiva materialier och deras anvaendning. |
US07/302,124 US4940846A (en) | 1983-08-18 | 1989-01-26 | Hydrophobic and/or abhesive materials, reactive diluents |
US07/529,324 US5061524A (en) | 1983-08-18 | 1990-05-29 | Hydrophobic and/or abhesive materials, reactive diluents |
US07/783,049 US5210121A (en) | 1983-08-18 | 1991-10-28 | Hydrophobic and/or abhesive materials, reactive diluents, and reactive plasticizers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833329877 DE3329877A1 (de) | 1983-08-18 | 1983-08-18 | Hydrophobe und/oder abhaesive masse, reaktiver verduenner und weichmacher und deren verwendung |
Publications (2)
Publication Number | Publication Date |
---|---|
DE3329877A1 DE3329877A1 (de) | 1985-03-07 |
DE3329877C2 true DE3329877C2 (en, 2012) | 1989-09-21 |
Family
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Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19833329877 Granted DE3329877A1 (de) | 1983-08-18 | 1983-08-18 | Hydrophobe und/oder abhaesive masse, reaktiver verduenner und weichmacher und deren verwendung |
DE3486389T Expired - Fee Related DE3486389D1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhäsive Masse, reaktive Verdünner, Weichmacher und deren Verwendung. |
DE8484903165T Expired - Lifetime DE3484280D1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhaesive masse, reaktive verduenner, weichmacher und deren verwendung. |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3486389T Expired - Fee Related DE3486389D1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhäsive Masse, reaktive Verdünner, Weichmacher und deren Verwendung. |
DE8484903165T Expired - Lifetime DE3484280D1 (de) | 1983-08-18 | 1984-08-17 | Hydrophobe und/oder abhaesive masse, reaktive verduenner, weichmacher und deren verwendung. |
Country Status (13)
Country | Link |
---|---|
US (1) | US5061524A (en, 2012) |
EP (2) | EP0408085B1 (en, 2012) |
JP (1) | JPS61500020A (en, 2012) |
AT (1) | ATE122691T1 (en, 2012) |
AU (1) | AU582547B2 (en, 2012) |
BR (1) | BR8407024A (en, 2012) |
CA (1) | CA1275204C (en, 2012) |
DE (3) | DE3329877A1 (en, 2012) |
DK (1) | DK172185D0 (en, 2012) |
ES (1) | ES535131A0 (en, 2012) |
FI (1) | FI72326C (en, 2012) |
IT (1) | IT1196227B (en, 2012) |
WO (1) | WO1985000820A1 (en, 2012) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
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AT388550B (de) * | 1987-06-27 | 1989-07-25 | Muanyagipari Kutato Intezet | Verfahren zur hydrophobierung von gipsgegenstaenden |
EP0381096A3 (en) * | 1989-01-30 | 1991-12-04 | Cappar Limited | Additive for two component epoxy resin compositions |
DE4138627A1 (de) * | 1991-11-25 | 1993-05-27 | Buna Ag | Verfahren zur hydrophobierung von calciumsulfatprodukten |
DE19544493A1 (de) * | 1995-11-29 | 1997-06-05 | Basf Ag | Strahlungshärtbare Zusammensetzung enthaltend alpha-Olefine |
US6057033A (en) * | 1997-12-12 | 2000-05-02 | Avery Dennison Corporation | Radiation-curable release compositions containing cellulose fibers |
US6486267B1 (en) | 2000-08-03 | 2002-11-26 | Avery Dennison Corporation | Release composition |
US6558513B1 (en) | 2001-05-29 | 2003-05-06 | Hercules Incorporated | Non-aqueous release from paper machine equipment |
EP2205691A2 (en) * | 2007-10-31 | 2010-07-14 | Lord Corporation | Additives for improved adhesion to oily substrates |
US8997434B1 (en) * | 2011-04-20 | 2015-04-07 | United States Gypsum Company | Method of installing a flooring system utilizing gypsum underlayments |
DE102014012198B4 (de) * | 2014-08-16 | 2016-03-10 | Technische Universität Bergakademie Freiberg | Wasserstoffhaltige Polysilathiane, Verfahren zu deren Herstellung und deren Verwendung |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
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US2340109A (en) * | 1942-06-23 | 1944-01-25 | Gen Electric | Copolymer of divinyl benzene polymers and unsaturated alkyd resins |
DE948818C (de) * | 1955-03-27 | 1956-09-06 | Gerhardt Schroeder | Kluppe |
US2952576A (en) * | 1955-11-02 | 1960-09-13 | Phillips Petroleum Co | Glass fiber treated with the reaction product of a liquid polymer of a conjugated diene and silicon halide |
BE631007A (en, 2012) | 1962-04-13 | |||
US3341475A (en) * | 1962-08-28 | 1967-09-12 | Hercules Inc | Vulcanizable copolymers of oxetanes and halogen substituted epoxides |
FR1345108A (fr) * | 1962-10-25 | 1963-12-06 | Nouvelle peinture pour surfaces souples | |
NL125765C (en, 2012) * | 1963-11-29 | |||
US3324051A (en) * | 1963-12-13 | 1967-06-06 | Goodyear Tire & Rubber | Polymerization of epoxides and episulfides |
NL126303C (en, 2012) * | 1965-01-08 | 1900-01-01 | ||
US3644315A (en) * | 1969-03-14 | 1972-02-22 | Exxon Research Engineering Co | Moisture-curable polymers |
US4083856A (en) * | 1969-08-18 | 1978-04-11 | Union Carbide Corporation | Addition of unsaturated epoxy monomer to Si-H with chloroplatinic acid and HCl-acceptor |
US3814679A (en) * | 1969-11-14 | 1974-06-04 | Union Rheinische Braunkohlen | Preparation of fuels for supersonic aircraft |
DE2014394A1 (de) * | 1970-03-25 | 1971-10-14 | Veba Chemie Ag | Verfahren zur Polymerisation von Vinylidenkohlenwasserstoffen, gegebenenfalls im Gemisch mit anderen Olefinen |
US3778487A (en) * | 1970-07-06 | 1973-12-11 | Sun Research Development | Polyisobutylene oil having a high viscosity index |
CA980321A (en) * | 1971-06-28 | 1975-12-23 | John O. Turner | Epoxidation of olefins using novel catalyst system |
US3877962A (en) * | 1972-12-18 | 1975-04-15 | Owens Illinois Inc | Substrate coating composition and process |
SE409302B (sv) * | 1973-12-14 | 1979-08-13 | Sjoo Gunnar Arthur S | Forfarande for att oka hallfastheten hos tre genom platimpregnering av treet med anvendning av katalysatorer |
JPS5850247B2 (ja) * | 1974-05-25 | 1983-11-09 | エヌオーケー株式会社 | ネツコウカセイソセイブツ |
GB1494332A (en) | 1974-07-09 | 1977-12-07 | Exxon Research Engineering Co | Self-sealing films |
US4154714A (en) * | 1975-03-05 | 1979-05-15 | Wacker-Chemie Gmbh | Adhesive repellent coatings and substrates coated therewith |
JPS53139696A (en) * | 1977-05-12 | 1978-12-06 | Daikin Ind Ltd | Fluorine-containing polyester copolymer, its production and use |
JPS5846142B2 (ja) * | 1977-07-05 | 1983-10-14 | 三菱電線工業株式会社 | ポリ4−メチルペンテン−1組成物 |
FR2405985A1 (fr) * | 1977-10-17 | 1979-05-11 | Rhone Poulenc Ind | Compositions organosiliciques durcissant a temperature ambiante en elastomeres presentant une permeabilite reduite aux gaz et aux vapeurs |
US4201808A (en) * | 1978-06-12 | 1980-05-06 | Union Carbide Corporation | Radiation curable silicone release compositions |
DE2917779C2 (de) * | 1979-05-03 | 1981-05-27 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur Herstellung von 2,3-Dimethylbuten-2 |
US4940846A (en) * | 1983-08-18 | 1990-07-10 | Rudolf Hinterwaldner | Hydrophobic and/or abhesive materials, reactive diluents |
-
1983
- 1983-08-18 DE DE19833329877 patent/DE3329877A1/de active Granted
-
1984
- 1984-08-13 CA CA000460896A patent/CA1275204C/en not_active Expired - Lifetime
- 1984-08-13 IT IT22325/84A patent/IT1196227B/it active
- 1984-08-14 ES ES535131A patent/ES535131A0/es active Granted
- 1984-08-17 BR BR8407024A patent/BR8407024A/pt unknown
- 1984-08-17 AT AT90114969T patent/ATE122691T1/de not_active IP Right Cessation
- 1984-08-17 EP EP90114969A patent/EP0408085B1/de not_active Expired - Lifetime
- 1984-08-17 JP JP59503251A patent/JPS61500020A/ja active Pending
- 1984-08-17 DE DE3486389T patent/DE3486389D1/de not_active Expired - Fee Related
- 1984-08-17 WO PCT/DE1984/000169 patent/WO1985000820A1/de active IP Right Grant
- 1984-08-17 AU AU33189/84A patent/AU582547B2/en not_active Ceased
- 1984-08-17 DE DE8484903165T patent/DE3484280D1/de not_active Expired - Lifetime
- 1984-08-17 EP EP84903165A patent/EP0153375B1/de not_active Expired - Lifetime
-
1985
- 1985-04-17 FI FI851531A patent/FI72326C/fi not_active IP Right Cessation
- 1985-04-17 DK DK172185A patent/DK172185D0/da not_active IP Right Cessation
-
1990
- 1990-05-29 US US07/529,324 patent/US5061524A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ES8604282A1 (es) | 1986-01-01 |
EP0153375B1 (de) | 1991-03-13 |
EP0153375A1 (de) | 1985-09-04 |
FI851531L (fi) | 1985-04-17 |
CA1275204C (en) | 1990-10-16 |
WO1985000820A1 (en) | 1985-02-28 |
FI72326B (fi) | 1987-01-30 |
US5061524A (en) | 1991-10-29 |
BR8407024A (pt) | 1985-07-30 |
DE3329877A1 (de) | 1985-03-07 |
EP0408085A2 (de) | 1991-01-16 |
IT8422325A0 (it) | 1984-08-13 |
JPS61500020A (ja) | 1986-01-09 |
DK172185A (da) | 1985-04-17 |
IT1196227B (it) | 1988-11-16 |
EP0408085A3 (en) | 1991-03-27 |
FI851531A0 (fi) | 1985-04-17 |
DE3486389D1 (de) | 1995-06-22 |
AU3318984A (en) | 1985-03-12 |
DE3484280D1 (de) | 1991-04-18 |
ATE122691T1 (de) | 1995-06-15 |
AU582547B2 (en) | 1989-04-06 |
FI72326C (fi) | 1987-05-11 |
EP0408085B1 (de) | 1995-05-17 |
ES535131A0 (es) | 1986-01-01 |
DK172185D0 (da) | 1985-04-17 |
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