CS274283B2 - Method of hardened product production - Google Patents

Method of hardened product production Download PDF

Info

Publication number: CS274283B2
Authority: CS; Czechoslovakia
Prior art keywords: weight; compounds; process according; groups; acid
Prior art date: 1985-11-21

Application number

CS839886A

Other languages

Czech (cs)

English (en)

Other versions

CS839886A2 (en

Inventor

Gerhard Dr Brindopke

Gerd Dr Walz

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-11-21

Filing date

1986-11-19

Publication date

1991-04-11

1986-11-19 Application filed by Hoechst Ag filed Critical Hoechst Ag

1990-09-12 Publication of CS839886A2 publication Critical patent/CS839886A2/cs

1991-04-11 Publication of CS274283B2 publication Critical patent/CS274283B2/cs

Links

238000000034 method Methods 0.000 title claims description 25
238000004519 manufacturing process Methods 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims description 43
-1 alkali metal alkoxides Chemical class 0.000 claims description 23
239000003054 catalyst Substances 0.000 claims description 21
239000005056 polyisocyanate Substances 0.000 claims description 20
229920001228 polyisocyanate Polymers 0.000 claims description 20
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 19
239000000047 product Substances 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
239000007795 chemical reaction product Substances 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
229920005989 resin Polymers 0.000 claims description 12
239000011347 resin Substances 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
239000004925 Acrylic resin Substances 0.000 claims description 10
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
229920001577 copolymer Polymers 0.000 claims description 8
239000003822 epoxy resin Substances 0.000 claims description 8
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 claims description 8
229920000647 polyepoxide Polymers 0.000 claims description 8
239000007787 solid Substances 0.000 claims description 8
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
229920000178 Acrylic resin Polymers 0.000 claims description 6
239000004593 Epoxy Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
125000003700 epoxy group Chemical group 0.000 claims description 6
229920000728 polyester Polymers 0.000 claims description 6
229920000570 polyether Polymers 0.000 claims description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
150000002430 hydrocarbons Chemical group 0.000 claims description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
239000011976 maleic acid Substances 0.000 claims description 5
UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 claims description 5
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 5
239000002879 Lewis base Substances 0.000 claims description 4
150000007527 lewis bases Chemical class 0.000 claims description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
229920000768 polyamine Polymers 0.000 claims description 3
229920006149 polyester-amide block copolymer Polymers 0.000 claims description 3
229920005862 polyol Polymers 0.000 claims description 3
150000003077 polyols Chemical class 0.000 claims description 3
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 2
239000004721 Polyphenylene oxide Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001409 amidines Chemical class 0.000 claims description 2
ZDBIRELPHMTOGQ-UHFFFAOYSA-N bis[(4-methoxyphenyl)methyl]-methylphosphane Chemical compound C1=CC(OC)=CC=C1CP(C)CC1=CC=C(OC)C=C1 ZDBIRELPHMTOGQ-UHFFFAOYSA-N 0.000 claims description 2
150000002357 guanidines Chemical class 0.000 claims description 2
XWZZZMXGYMXMQX-UHFFFAOYSA-N methyl-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C)C1=CC=C(C)C=C1 XWZZZMXGYMXMQX-UHFFFAOYSA-N 0.000 claims description 2
229920003055 poly(ester-imide) Polymers 0.000 claims description 2
RAVACSWYIIPFFV-UHFFFAOYSA-N tris[(4-methoxyphenyl)methyl]phosphane Chemical compound C1=CC(OC)=CC=C1CP(CC=1C=CC(OC)=CC=1)CC1=CC=C(OC)C=C1 RAVACSWYIIPFFV-UHFFFAOYSA-N 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims 2
229910019142 PO4 Inorganic materials 0.000 claims 1
235000011114 ammonium hydroxide Nutrition 0.000 claims 1
235000021317 phosphate Nutrition 0.000 claims 1
150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 description 19
150000002148 esters Chemical class 0.000 description 14
125000000217 alkyl group Chemical group 0.000 description 12
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 11
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 9
238000000576 coating method Methods 0.000 description 9
239000012948 isocyanate Substances 0.000 description 9
229920000642 polymer Polymers 0.000 description 9
239000008096 xylene Substances 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
150000002513 isocyanates Chemical class 0.000 description 7
150000005846 sugar alcohols Polymers 0.000 description 7
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000011248 coating agent Substances 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
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 5
239000003973 paint Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
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 4
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 4
238000004132 cross linking Methods 0.000 description 4
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000005058 Isophorone diisocyanate Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000945 filler Substances 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
239000011521 glass Substances 0.000 description 3
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
239000000178 monomer Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229910000064 phosphane Inorganic materials 0.000 description 3
150000003002 phosphanes Chemical class 0.000 description 3
150000003003 phosphines Chemical class 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
239000001294 propane Substances 0.000 description 3
150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
229920000877 Melamine resin Polymers 0.000 description 2
238000006845 Michael addition reaction Methods 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000008064 anhydrides Chemical class 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
239000011230 binding agent Substances 0.000 description 2
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000001273 butane Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 2
239000000975 dye Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 2
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000004922 lacquer Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000002763 monocarboxylic acids Chemical class 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000049 pigment Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
239000004848 polyfunctional curative Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000758 substrate Substances 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
239000010936 titanium Substances 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
238000005829 trimerization reaction Methods 0.000 description 2
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
239000002966 varnish Substances 0.000 description 2
239000002023 wood Substances 0.000 description 2
SLYLZTFTYNJIID-UHFFFAOYSA-N (2-methoxyphenyl)methyl-diphenylphosphane Chemical compound COC1=CC=CC=C1CP(C=1C=CC=CC=1)C1=CC=CC=C1 SLYLZTFTYNJIID-UHFFFAOYSA-N 0.000 description 1
IBTPYQRLYBREMH-UHFFFAOYSA-N (4-methoxyphenyl)methyl-diphenylphosphane Chemical compound C1=CC(OC)=CC=C1CP(C=1C=CC=CC=1)C1=CC=CC=C1 IBTPYQRLYBREMH-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 1
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
XKQMKMVTDKYWOX-UHFFFAOYSA-N 1-[2-hydroxypropyl(methyl)amino]propan-2-ol Chemical compound CC(O)CN(C)CC(C)O XKQMKMVTDKYWOX-UHFFFAOYSA-N 0.000 description 1
QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 1
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 1
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230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
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NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 description 1
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XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
RUNXIYVBAYQTIH-UHFFFAOYSA-N butylimino(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=NCCCC)C1=CC=CC=C1 RUNXIYVBAYQTIH-UHFFFAOYSA-N 0.000 description 1
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239000004567 concrete Substances 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
XMYLSWOTJKUSHE-UHFFFAOYSA-N cyanamide;lead Chemical compound [Pb].NC#N XMYLSWOTJKUSHE-UHFFFAOYSA-N 0.000 description 1
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WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
ZKBBUZRGPULIRN-UHFFFAOYSA-N diethyl 2,2-diethylpropanedioate Chemical compound CCOC(=O)C(CC)(CC)C(=O)OCC ZKBBUZRGPULIRN-UHFFFAOYSA-N 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
239000011094 fiberboard Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
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239000007789 gas Substances 0.000 description 1
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FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
VPKDCDLSJZCGKE-UHFFFAOYSA-N methanediimine Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
VOWOYSREBMUEQA-UHFFFAOYSA-N methyl-bis(2-methylphenyl)phosphane Chemical compound C=1C=CC=C(C)C=1P(C)C1=CC=CC=C1C VOWOYSREBMUEQA-UHFFFAOYSA-N 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000465 moulding Methods 0.000 description 1
YQIYTHIOMUASNS-UHFFFAOYSA-N n-(diphenylphosphanylmethyl)-n-ethylethanamine Chemical compound C=1C=CC=CC=1P(CN(CC)CC)C1=CC=CC=C1 YQIYTHIOMUASNS-UHFFFAOYSA-N 0.000 description 1
PYUYQYBDJFMFTH-WMMMYUQOSA-N naphthol red Chemical compound CCOC1=CC=CC=C1NC(=O)C(C1=O)=CC2=CC=CC=C2\C1=N\NC1=CC=C(C(N)=O)C=C1 PYUYQYBDJFMFTH-WMMMYUQOSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000010422 painting Methods 0.000 description 1
230000035515 penetration Effects 0.000 description 1
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
XUEZMHGLLYOBIT-UHFFFAOYSA-N phenylmethanamine;hydrate Chemical class [OH-].[NH3+]CC1=CC=CC=C1 XUEZMHGLLYOBIT-UHFFFAOYSA-N 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000010454 slate Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
NVKTUNLPFJHLCG-UHFFFAOYSA-N strontium chromate Chemical compound [Sr+2].[O-][Cr]([O-])(=O)=O NVKTUNLPFJHLCG-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
BSFVCIYREAMMOJ-UHFFFAOYSA-N tris[(2-methoxyphenyl)methyl]phosphane Chemical compound COC1=CC=CC=C1CP(CC=1C(=CC=CC=1)OC)CC1=CC=CC=C1OC BSFVCIYREAMMOJ-UHFFFAOYSA-N 0.000 description 1
235000013799 ultramarine blue Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002025 wood fiber Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
229910052984 zinc sulfide Inorganic materials 0.000 description 1
NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- 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
- C08G18/83—Chemically modified polymers
- C08G18/833—Chemically modified polymers by nitrogen containing compounds
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8093—Compounds containing active methylene groups
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
General Chemical & Material Sciences (AREA)
Paints Or Removers (AREA)
Polyurethanes Or Polyureas (AREA)
Epoxy Resins (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Compositions Of Macromolecular Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Macromonomer-Based Addition Polymer (AREA)

CS839886A 1985-11-21 1986-11-19 Method of hardened product production CS274283B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853541140 DE3541140A1 (de)	1985-11-21	1985-11-21	Haertungsprodukt auf basis von olefinisch ungesaettigten verbindungen und wasserstoffaktiven verbindungen, verfahren zu dessen herstellung und darauf basierende zwei-komponentenlacke

Publications (2)

Publication Number	Publication Date
CS839886A2 CS839886A2 (en)	1990-09-12
CS274283B2 true CS274283B2 (en)	1991-04-11

Family

ID=6286451

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS839886A CS274283B2 (en)	1985-11-21	1986-11-19	Method of hardened product production

Country Status (22)

Country	Link
US (1)	US5159024A (es)
EP (1)	EP0224158B1 (es)
JP (1)	JPH0816152B2 (es)
KR (1)	KR950007997B1 (es)
CN (1)	CN1013117B (es)
AR (1)	AR245157A1 (es)
AT (1)	ATE98965T1 (es)
AU (1)	AU588399B2 (es)
BR (1)	BR8605727A (es)
CA (1)	CA1282536C (es)
CS (1)	CS274283B2 (es)
DD (1)	DD260072A5 (es)
DE (2)	DE3541140A1 (es)
DK (1)	DK555586A (es)
ES (1)	ES2061437T3 (es)
FI (1)	FI89930C (es)
IE (1)	IE62801B1 (es)
MX (1)	MX4392B (es)
NO (1)	NO169549C (es)
PL (1)	PL149347B1 (es)
PT (1)	PT83783B (es)
ZA (1)	ZA868795B (es)

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DE3734916A1 (de) *	1987-10-15	1989-04-27	Hoechst Ag	Haertungskomponente fuer kunstharze, diese enthaltende haertbare mischungen sowie deren verwendung
DE3932517A1 (de) *	1989-09-29	1991-04-11	Herberts Gmbh	Bindemittelzusammensetzung und deren verwendung in ueberzugsmitteln
DE4133704A1 (de) *	1991-10-11	1993-04-15	Herberts Gmbh	Katalysatorfreies einkomponenten-ueberzugsmittel und dessen verwendung zur herstellung von saeurebestaendigen lackierungen
DE4213671A1 (de) *	1992-04-25	1993-10-28	Herberts Gmbh	Verfahren zur Rückgewinnung des Oversprays von wäßrigen Überzugsmitteln beim Spritzauftrag in Spritzkabinen
BE1005775A3 (nl) *	1992-04-29	1994-01-25	Dsm Nv	Bindmiddelsamenstelling voor oplosmiddel- of watergebaseerde coatings.
DE4225104C1 (de) *	1992-07-30	1993-12-09	Herberts Gmbh	Überzugsmittel und dessen Verwendung bei der Herstellung von Überzügen mit rasch bearbeitbarer Oberfläche
DE4225105C1 (de) *	1992-07-30	1993-12-09	Herberts Gmbh	Überzugsmittel und dessen Verwendung bei der Herstellung von Überzügen mit rasch bearbeitbarer Oberfläche
DE4237492A1 (de) *	1992-11-06	1994-05-11	Herberts Gmbh	Wäßrige Bindemittelzusammensetzung, diese enthaltende Überzugsmittel und deren Verwendung
DE4237490A1 (de) *	1992-11-06	1994-05-11	Herberts Gmbh	Überzugsmittel und dessen Verwendung zur Herstellung von säurebeständigen Lackierungen
EP0672072B1 (en) *	1993-09-22	1998-08-05	Ashland Oil, Inc.	Polyurethane reaction system having a blocked catalyst combination
CA2164994A1 (en) *	1994-12-24	1996-06-25	Heinz Dietholf Becker	Binder composition, coating agents containing it, and use thereof
JPH08283627A (ja) *	1995-04-12	1996-10-29	Nippon Paint Co Ltd	塗料用一液熱硬化性樹脂組成物
DE19528878A1 (de) *	1995-08-05	1997-02-06	Herberts Gmbh	Wäßrige Überzugsmittel unter Verwendung von Polyalkylenglykoldialkylethern und Verfahren zur Mehrschichtlackierung
AU721485B2 (en) *	1996-10-30	2000-07-06	Ems-Patent Ag	Heat curable coating compounds
GB2323599A (en) *	1997-03-18	1998-09-30	Courtaulds Plc	Compositions curable by a Michael reaction
US7256241B2 (en)	2000-01-21	2007-08-14	Cyclics Corporation	Methods for polymerizing macrocyclic polyester oligomers using catalyst promoters
US6906147B2 (en)	2002-03-20	2005-06-14	Cyclics Corporation	Catalytic systems
RU2265621C2 (ru) *	2000-03-13	2005-12-10	Акцо Нобель Н.В.	Композиция, включающая соединение с изоцианатной функциональной группой, соединение, способное реагировать с изоцианатами, и сокатализатор
US7750109B2 (en)	2000-09-01	2010-07-06	Cyclics Corporation	Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer
US7767781B2 (en) *	2000-09-01	2010-08-03	Cyclics Corporation	Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom
JP2004507599A (ja)	2000-09-01	2004-03-11	サイクリクス　コーポレイション	線形ポリエステルを、大環状オリゴエステル組成物および大環状オリゴエステルに変換する方法
US7304123B2 (en)	2001-06-27	2007-12-04	Cyclics Corporation	Processes for shaping macrocyclic oligoesters
US7071291B2 (en)	2001-06-27	2006-07-04	Cyclics Corporation	Isolation, formulation and shaping of macrocyclic oligoesters
US6787632B2 (en)	2001-10-09	2004-09-07	Cyclics Corporation	Organo-titanate catalysts for preparing pure macrocyclic oligoesters
KR20030053018A (ko) *	2001-12-21	2003-06-27	다이니혼 잉키 가가쿠 고교 가부시키가이샤	경화성 수지 조성물 및 아크릴로일기, 치환된메타크릴레이트기 및 β-디카르보닐기를 갖는 올리고머또는 폴리머의 제조 방법
US8013068B2 (en) *	2003-01-02	2011-09-06	Rohm And Haas Company	Michael addition compositions
DE102015105983A1 (de)	2015-04-20	2016-10-20	Mankiewicz Gebr. & Co. Gmbh & Co. Kg	Verbesserte Beschichtungssysteme, deren Verwendung zur Beschichtung von Bauteilen sowie damit beschichtete Bauteile für Land- und Baumaschinen
CN113437438A (zh) *	2020-03-06	2021-09-24	厦门大学	一种环氧树脂改性陶瓷隔膜及其制备方法和应用

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JPS4928653B1 (es) *	1970-04-21	1974-07-29
DE2612783C3 (de) *	1976-03-25	1981-11-05	Hoechst Ag, 6000 Frankfurt	Biurete, Verfahren zu ihrer Herstellung und deren Verwendung
DE2631949A1 (de) *	1976-07-15	1978-01-19	Bayer Ag	Strahlen-haertende bindemittel
DE2639491B1 (de) *	1976-09-02	1978-02-02	Hoechst Ag	Einbrennlacke auf der Grundlage von freie Hydroxylgruppen enthaltenden Polyester- und/oder Alkydharzen und blockierten Polyisocyanaten
DE3046409A1 (de) *	1980-12-10	1982-07-15	Bayer Ag, 5090 Leverkusen	Beschichtungsmittel und ein verfahren zur herstellung von ueberzuegen
ATE46178T1 (de) *	1984-04-04	1989-09-15	Hoechst Ag	Umsetzungsprodukt von olefinisch ungesaettigten verbindungen mit wasserstoffaktiven verbindungen, verfahren zu dessen herstellung und darauf basierende 2-komponentenlacke.

1985
- 1985-11-21 DE DE19853541140 patent/DE3541140A1/de not_active Withdrawn
1986
- 1986-11-15 DE DE86115895T patent/DE3689441D1/de not_active Expired - Fee Related
- 1986-11-15 EP EP86115895A patent/EP0224158B1/de not_active Expired - Lifetime
- 1986-11-15 AT AT86115895T patent/ATE98965T1/de not_active IP Right Cessation
- 1986-11-15 ES ES86115895T patent/ES2061437T3/es not_active Expired - Lifetime
- 1986-11-18 DD DD86296387A patent/DD260072A5/de not_active IP Right Cessation
- 1986-11-19 CS CS839886A patent/CS274283B2/cs unknown
- 1986-11-19 MX MX4392A patent/MX4392B/es unknown
- 1986-11-19 AR AR86305949A patent/AR245157A1/es active
- 1986-11-19 US US06/932,635 patent/US5159024A/en not_active Expired - Fee Related
- 1986-11-19 FI FI864719A patent/FI89930C/fi not_active IP Right Cessation
- 1986-11-19 KR KR1019860009771A patent/KR950007997B1/ko not_active IP Right Cessation
- 1986-11-20 IE IE306786A patent/IE62801B1/en not_active IP Right Cessation
- 1986-11-20 CA CA000523406A patent/CA1282536C/en not_active Expired - Fee Related
- 1986-11-20 AU AU65536/86A patent/AU588399B2/en not_active Ceased
- 1986-11-20 NO NO864643A patent/NO169549C/no unknown
- 1986-11-20 JP JP61275473A patent/JPH0816152B2/ja not_active Expired - Lifetime
- 1986-11-20 DK DK555586A patent/DK555586A/da not_active Application Discontinuation
- 1986-11-20 PT PT83783A patent/PT83783B/pt not_active IP Right Cessation
- 1986-11-20 ZA ZA868795A patent/ZA868795B/xx unknown
- 1986-11-20 PL PL1986262500A patent/PL149347B1/pl unknown
- 1986-11-20 CN CN86107731A patent/CN1013117B/zh not_active Expired
- 1986-11-20 BR BR8605727A patent/BR8605727A/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
MX4392A (es)	1993-02-01
ZA868795B (en)	1987-07-29
CN86107731A (zh)	1987-06-17
DK555586A (da)	1987-05-22
FI89930C (fi)	1993-12-10
PT83783B (pt)	1989-06-30
IE863067L (en)	1987-05-21
PL149347B1 (en)	1990-02-28
FI89930B (fi)	1993-08-31
AU588399B2 (en)	1989-09-14
CN1013117B (zh)	1991-07-10
KR950007997B1 (ko)	1995-07-24
AR245157A1 (es)	1993-12-30
IE62801B1 (en)	1995-03-08
NO864643L (no)	1987-05-22
EP0224158A2 (de)	1987-06-03
DE3541140A1 (de)	1987-05-27
PL262500A1 (en)	1987-11-30
AU6553686A (en)	1987-05-28
NO864643D0 (no)	1986-11-20
BR8605727A (pt)	1987-08-18
JPS62143927A (ja)	1987-06-27
EP0224158A3 (en)	1989-01-04
FI864719A0 (fi)	1986-11-19
DK555586D0 (da)	1986-11-20
FI864719A (fi)	1987-05-22
CS839886A2 (en)	1990-09-12
CA1282536C (en)	1991-04-02
NO169549B (no)	1992-03-30
NO169549C (no)	1992-07-08
ES2061437T3 (es)	1994-12-16
US5159024A (en)	1992-10-27
ATE98965T1 (de)	1994-01-15
EP0224158B1 (de)	1993-12-22
KR870005023A (ko)	1987-06-04
DE3689441D1 (de)	1994-02-03
MX4392B (es)	1993-05-06
JPH0816152B2 (ja)	1996-02-21
PT83783A (de)	1986-12-01
DD260072A5 (de)	1988-09-14

Publication	Publication Date	Title
CS274283B2 (en)	1991-04-11	Method of hardened product production
US4871822A (en)	1989-10-03	Reaction product of olefinically unsaturated compounds with compounds containing active hydrogen, processes for their preparation and 2-component lacquers based thereon HOE 85/F O36J
KR101320004B1 (ko)	2013-10-22	포스폰산 디에스테르 및 디포스폰산 디에스테르의 용도, 및포스폰산 디에스테르 및 디포스폰산 디에스테르를함유하는 실란기함유，경화가능한 혼합물
US5336566A (en)	1994-08-09	Tri-carbamate-functional crosslinking agents
US7339020B2 (en)	2008-03-04	High-functionality polyisocyanates
AU745476B2 (en)	2002-03-21	Sprayable coating compositions comprising an oxazolidine, an isocyanable, and a compound selected from a mercapto and a sulfonic acid functional compound
US9404011B2 (en)	2016-08-02	Coating agents having improved runoff tendency
US20090142601A1 (en)	2009-06-04	Aspartic ester functional compounds
KR20010111590A (ko)	2001-12-19	머캅토-작용기 화합물을 포함하는 조성물
EP2521745B1 (en)	2015-08-05	Solvent borne two-component polyurethane coating composition
KR20120028934A (ko)	2012-03-23	우레트디온 기 및 상이한 작용 기를 지닌 화합물을 함유한 경화성 코팅 조성물, 및 경화된 코팅
KR20180051522A (ko)	2018-05-16	스크래치-내성 2-성분 폴리우레탄 코팅
US4861853A (en)	1989-08-29	Isocyanate functional polymers
US4983676A (en)	1991-01-08	Isocyanate functional polymers
JP5606522B2 (ja)	2014-10-15	ウレトジオン構造を有するオリゴマー、その製造方法、それを被覆する被覆組成物、及びそれらの硬化被覆
US5169979A (en)	1992-12-08	Curing component, and the use thereof
KR930007692B1 (ko)	1993-08-18	올레핀성 불포화 화합물과 활성 수소 함유 화합물의 반응 생성물의 제조방법 및 당해 생성물을 함유하는 2성분 래커
US6566481B2 (en)	2003-05-20	Polyisocyanates with allophanate groups derived from alicyclic alkanediols
KR19990022816A (ko)	1999-03-25	폴리우레탄 폴리올과 감소된 점도를 갖는 그의 코팅재
US4731415A (en)	1988-03-15	Polyisocyanates and resin compositions thereof