DE3041732A1 - Loesungen von isocyanato-isocyanuraten in weichmachern fuer polyvinylchlorid, ein verfahren zu ihrer herstellung, sowie ihre verwendung als haftverbessernde zusatzmittel in beschichtungsmitteln auf basis von weichgemachtem polyvinylchlorid - Google Patents
Loesungen von isocyanato-isocyanuraten in weichmachern fuer polyvinylchlorid, ein verfahren zu ihrer herstellung, sowie ihre verwendung als haftverbessernde zusatzmittel in beschichtungsmitteln auf basis von weichgemachtem polyvinylchloridInfo
- Publication number
- DE3041732A1 DE3041732A1 DE19803041732 DE3041732A DE3041732A1 DE 3041732 A1 DE3041732 A1 DE 3041732A1 DE 19803041732 DE19803041732 DE 19803041732 DE 3041732 A DE3041732 A DE 3041732A DE 3041732 A1 DE3041732 A1 DE 3041732A1
- Authority
- DE
- Germany
- Prior art keywords
- isocyanate groups
- solutions
- diisocyanatodiphenylmethane
- polyvinyl chloride
- mol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229920000915 polyvinyl chloride Polymers 0.000 title claims abstract description 54
- 239000004800 polyvinyl chloride Substances 0.000 title claims abstract description 54
- 239000000654 additive Substances 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 22
- 230000000996 additive effect Effects 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- 239000011248 coating agent Substances 0.000 title description 9
- 239000000853 adhesive Substances 0.000 title description 7
- 229920000642 polymer Polymers 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- 239000004014 plasticizer Substances 0.000 claims abstract description 27
- 238000005829 trimerization reaction Methods 0.000 claims abstract description 22
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 18
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims abstract description 15
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims abstract description 9
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 239000008199 coating composition Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 8
- 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 claims description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 238000002845 discoloration Methods 0.000 abstract description 5
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 73
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 27
- 229920001944 Plastisol Polymers 0.000 description 26
- 239000004999 plastisol Substances 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 16
- 238000000576 coating method Methods 0.000 description 13
- 239000002318 adhesion promoter Substances 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 6
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 6
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WIJRMGQOERPOJA-UHFFFAOYSA-N benzyl cyanate Chemical compound N#COCC1=CC=CC=C1 WIJRMGQOERPOJA-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RVBLXUAPXWEIPM-UHFFFAOYSA-N 1-o-benzyl 2-o-(2-ethylhexyl) benzene-1,2-dicarboxylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 RVBLXUAPXWEIPM-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- RYUJRXVZSJCHDZ-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC(C)C)OC1=CC=CC=C1 RYUJRXVZSJCHDZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RTOSJSSWYMWLIG-UHFFFAOYSA-J C(CCCCCCCCCCC)(=O)[O-].[Ba+2].[Cd+2].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCC)(=O)[O-].[Ba+2].[Cd+2].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-] RTOSJSSWYMWLIG-UHFFFAOYSA-J 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241001506137 Rapa Species 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 1
- SLETZFVTVXVPLS-UHFFFAOYSA-N [Zn].[Cd].[Ba] Chemical compound [Zn].[Cd].[Ba] SLETZFVTVXVPLS-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- UMKARVFXJJITLN-UHFFFAOYSA-N lead;phosphorous acid Chemical compound [Pb].OP(O)O UMKARVFXJJITLN-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
-
- 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
- C09D127/00—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 a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—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 a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/04—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 a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C09D127/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Image Analysis (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Apparatus For Radiation Diagnosis (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803041732 DE3041732A1 (de) | 1980-11-05 | 1980-11-05 | Loesungen von isocyanato-isocyanuraten in weichmachern fuer polyvinylchlorid, ein verfahren zu ihrer herstellung, sowie ihre verwendung als haftverbessernde zusatzmittel in beschichtungsmitteln auf basis von weichgemachtem polyvinylchlorid |
| US06/313,842 US4518729A (en) | 1980-11-05 | 1981-10-22 | Solutions of isocyanato-isocyanurates in plasticizers for polyvinyl chloride, a process for their production and their use as adhesion-improving additives in coating compositions based on plasticized polyvinyl chloride |
| EP81108894A EP0051239B1 (de) | 1980-11-05 | 1981-10-24 | Lösungen von Isocyanato-Isocyanuraten in Weichmachern für Polyvinylchlorid, ein Verfahren zu ihrer Herstellung, sowie ihre Verwendung als haftverbessernde Zusatzmittel in Beschichtungsmitteln auf Basis von weichgemachtem Polyvinylchlorid |
| DE8181108894T DE3168076D1 (en) | 1980-11-05 | 1981-10-24 | Solutions of isocyanato-isocyanurates in plasticizers for polyvinylchloride, process for their preparation and their use in adhesion improving additives in coating agents based on plasticized polyvinylchloride |
| AT81108894T ATE11051T1 (de) | 1980-11-05 | 1981-10-24 | Loesungen von isocyanato-isocyanuraten in weichmachern fuer polyvinylchlorid, ein verfahren zu ihrer herstellung, sowie ihre verwendung als haftverbessernde zusatzmittel in beschichtungsmitteln auf basis von weichgemachtem polyvinylchlorid. |
| JP56174671A JPS57105441A (en) | 1980-11-05 | 1981-11-02 | Isocyanate-isocyanurate solution in plasticizer for vinyl chloride, manufacture and use as adhesion increasing additive in coating composition based on plasticized vinyl chloride |
| ZA817631A ZA817631B (en) | 1980-11-05 | 1981-11-04 | Solutions of isocyanato-isocyanurates in plasticisers for polyvinyl chloride,a process for their production and their use as adhesion-improving additives in coating compositions based on plasticised polyvinyl chloride |
| ES506843A ES506843A0 (es) | 1980-11-05 | 1981-11-04 | Procedimiento para la obtencion de soluciones de isocianato-isocianuratos en plastificantes para cloruro de polivinilo. |
| DK487681A DK487681A (da) | 1980-11-05 | 1981-11-04 | Oploesninger af isocyanato-isocyanurater i bloedgoeringsmidler til polyvinylchlorid fremgangsmaade til deres fremstilling samt deres anvendelse som haefteforbedrende tilsaetningsmidler i belaegningsmidler paa basis af bloedgjort polyvinylchlorid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803041732 DE3041732A1 (de) | 1980-11-05 | 1980-11-05 | Loesungen von isocyanato-isocyanuraten in weichmachern fuer polyvinylchlorid, ein verfahren zu ihrer herstellung, sowie ihre verwendung als haftverbessernde zusatzmittel in beschichtungsmitteln auf basis von weichgemachtem polyvinylchlorid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3041732A1 true DE3041732A1 (de) | 1982-06-09 |
Family
ID=6116025
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803041732 Withdrawn DE3041732A1 (de) | 1980-11-05 | 1980-11-05 | Loesungen von isocyanato-isocyanuraten in weichmachern fuer polyvinylchlorid, ein verfahren zu ihrer herstellung, sowie ihre verwendung als haftverbessernde zusatzmittel in beschichtungsmitteln auf basis von weichgemachtem polyvinylchlorid |
| DE8181108894T Expired DE3168076D1 (en) | 1980-11-05 | 1981-10-24 | Solutions of isocyanato-isocyanurates in plasticizers for polyvinylchloride, process for their preparation and their use in adhesion improving additives in coating agents based on plasticized polyvinylchloride |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181108894T Expired DE3168076D1 (en) | 1980-11-05 | 1981-10-24 | Solutions of isocyanato-isocyanurates in plasticizers for polyvinylchloride, process for their preparation and their use in adhesion improving additives in coating agents based on plasticized polyvinylchloride |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4518729A (https=) |
| EP (1) | EP0051239B1 (https=) |
| JP (1) | JPS57105441A (https=) |
| AT (1) | ATE11051T1 (https=) |
| DE (2) | DE3041732A1 (https=) |
| DK (1) | DK487681A (https=) |
| ES (1) | ES506843A0 (https=) |
| ZA (1) | ZA817631B (https=) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005070984A1 (de) * | 2004-01-23 | 2005-08-04 | Lanxess Deutschland Gmbh | Monomerenarme, niedrigviskose lösungen von tdi-isocyanuraten in verzweigten dialkylphthalaten |
| US20080277106A1 (en) * | 2004-02-03 | 2008-11-13 | Atlas Copco Airpower | Heat Exchanger |
| DE102007034977A1 (de) | 2007-07-26 | 2009-01-29 | Lanxess Deutschland Gmbh | Phthalatfreie Isocyanuratzubereitungen |
| EP2354172A1 (de) | 2010-02-08 | 2011-08-10 | LANXESS Deutschland GmbH | Phthalatfreie Isocyanuratzubereitungen |
| DE102010033061A1 (de) | 2010-08-02 | 2012-02-02 | Bayer Materialscience Ag | Phthalatfreie Isocyanuratzubereitung |
| EP3909994A1 (de) | 2021-02-18 | 2021-11-17 | LANXESS Deutschland GmbH | Neue phthalatfreie isocyanurat-zusammensetzung |
| EP3916031A1 (de) | 2020-05-28 | 2021-12-01 | LANXESS Deutschland GmbH | Neue phthalatfreie isocyanurat-zusammensetzung und deren verwendung |
| WO2025131813A1 (de) | 2023-12-20 | 2025-06-26 | Lanxess Deutschland Gmbh | Neue phthalatfreie isocyanurat-zusammensetzung und deren verwendung |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3304889A1 (de) * | 1983-02-12 | 1984-08-16 | Basf Ag, 6700 Ludwigshafen | Fluessige, isocyanuratgruppen enthaltende polyisocyanatmischungen aus 4,4'- und 2,4'-diphenylmethan-diisocyanaten, verfahren zu deren herstellung und deren verwendung fuer polyurethan- oder polyisocyanurat-kunststoffe |
| DE3339579A1 (de) * | 1983-11-02 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung sowie ihre verwendung als isocyanat-komponente in polyurethanlacken |
| DE3403497A1 (de) | 1984-02-02 | 1985-08-08 | Bayer Ag, 5090 Leverkusen | Haftungsvermittelnde zusaetze enthaltende pvc-plastisole fuer beschichtungszwecke und ihre verwendung |
| NL8500475A (nl) * | 1985-02-20 | 1986-09-16 | Akzo Nv | Thixotrope bekledingssamenstelling. |
| JPS61287933A (ja) * | 1985-06-05 | 1986-12-18 | Mitsuboshi Belting Ltd | 繊維材料と軟質ポリ塩化ビニ−ルとの接着方法 |
| JPS62148536A (ja) * | 1985-12-23 | 1987-07-02 | Mitsubishi Kasei Vinyl Co | 複合ポリエステルシ−ト及び積層シ−トの製造方法 |
| JPS63265637A (ja) * | 1987-04-24 | 1988-11-02 | Mitsubishi Kasei Vinyl Co | 複合ポリエステルシ−ト及びその製造方法 |
| JPH01292053A (ja) * | 1988-05-18 | 1989-11-24 | Kiyoueishiya Yushi Kagaku Kogyo Kk | 低温硬化性プラスチゾル組成物 |
| DE3920325C2 (de) * | 1988-06-24 | 2001-04-12 | Sunstar Engineering Inc | Maskierte Polyisocyanuratverbindung und sie enthaltende Plastisolzusammensetzung |
| US5130402A (en) * | 1988-07-01 | 1992-07-14 | Sanyo Chemical Industries, Ltd. | Coating composition and plastisol composition, and articles coated therewith |
| JPH02296851A (ja) * | 1989-05-10 | 1990-12-07 | Sanyo Chem Ind Ltd | プラスチゾル組成物 |
| US5092953A (en) * | 1989-03-21 | 1992-03-03 | Air Products And Chemicals, Inc. | Aqueous vinyl chloride-ethylene copolymer/polyisocyanate adhesive compositions for wood composites |
| DE3938880A1 (de) * | 1989-11-24 | 1991-05-29 | Huels Chemische Werke Ag | Textile fixiereinlagen |
| US6515125B1 (en) * | 2001-03-09 | 2003-02-04 | Bayer Corporation | Liquid partially trimerized polyisocyanates based on toluene diisocyanate and diphenylmethane diisocyanate |
| CN103834121B (zh) * | 2014-02-28 | 2016-04-27 | 广东若天新材料科技有限公司 | 三(2-羟基环己基)异氰尿酸酯在pvc复合热稳定剂中的应用及应用其制备的pvc制品 |
| US20160251798A1 (en) * | 2015-02-26 | 2016-09-01 | Eastman Chemical Company | Bonding agents for plastisols containing dotp or dinch |
| PL3589708T3 (pl) | 2017-03-01 | 2023-02-13 | Basf Se | Kompozycja środka powłokowego zawierająca pvc i składniki plastyfikujące |
| RU2019130672A (ru) * | 2017-03-01 | 2021-04-01 | Басф Се | Покровная композиция, содержащая поливинилхлорид и пластифицирующие компоненты |
| US11359045B2 (en) * | 2017-12-21 | 2022-06-14 | Covestro Deutschland Ag | Method for producing isocyanate mixtures containing isocyanurate groups |
| CN108822276B (zh) * | 2018-05-29 | 2021-01-19 | 武汉理工大学 | 一种pvc/pet复合膜胶黏剂的制备方法 |
| CN112300519A (zh) * | 2020-11-12 | 2021-02-02 | 广元瑞峰新材料有限公司 | 一种基于mdi-dinp的pvc交联剂及其pvc交联材料 |
| CN112300518A (zh) * | 2020-11-12 | 2021-02-02 | 广元瑞峰新材料有限公司 | 一种基于tdi-dbp的pvc交联剂 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505A (en) * | 1844-03-26 | Mill-btjsh | ||
| GB1052042A (https=) * | 1962-08-09 | |||
| DE1669161A1 (de) * | 1966-01-29 | 1970-08-20 | Goldschmidt Ag Th | Selbsthaftendes Plastisol oder Organosol auf Basis Polyvinylchlorid bzw.Polyvinylchloridmischpolymerisat |
| DE1669186B1 (de) * | 1967-05-11 | 1969-12-04 | Henkel & Cie Gmbh | Plastisol |
| GB1455701A (en) * | 1973-04-19 | 1976-11-17 | Ici Ltd | Polyvinyl chloride plastisol compositions |
| DE2325926C2 (de) * | 1973-05-22 | 1990-08-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von lignozellulosehaltigen Werkstoffen |
| JPS5533704B2 (https=) * | 1973-06-15 | 1980-09-02 | ||
| US3947426A (en) * | 1974-04-12 | 1976-03-30 | Story Chemical Corporation | Solid particle-form polymerizable polymeric material and compositions, structures and methods of employing and producing the same |
| DE2452532C3 (de) * | 1974-11-06 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanurat-Struktur |
| DE2551634C3 (de) * | 1975-11-18 | 1980-07-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten |
| DE2732662A1 (de) * | 1977-07-20 | 1979-02-01 | Veba Chemie Ag | Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen-enthaltende verbindungen |
| DE2806731A1 (de) * | 1978-02-17 | 1979-08-23 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
-
1980
- 1980-11-05 DE DE19803041732 patent/DE3041732A1/de not_active Withdrawn
-
1981
- 1981-10-22 US US06/313,842 patent/US4518729A/en not_active Expired - Lifetime
- 1981-10-24 AT AT81108894T patent/ATE11051T1/de not_active IP Right Cessation
- 1981-10-24 EP EP81108894A patent/EP0051239B1/de not_active Expired
- 1981-10-24 DE DE8181108894T patent/DE3168076D1/de not_active Expired
- 1981-11-02 JP JP56174671A patent/JPS57105441A/ja active Granted
- 1981-11-04 ES ES506843A patent/ES506843A0/es active Granted
- 1981-11-04 ZA ZA817631A patent/ZA817631B/xx unknown
- 1981-11-04 DK DK487681A patent/DK487681A/da not_active Application Discontinuation
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005070984A1 (de) * | 2004-01-23 | 2005-08-04 | Lanxess Deutschland Gmbh | Monomerenarme, niedrigviskose lösungen von tdi-isocyanuraten in verzweigten dialkylphthalaten |
| DE102004003794B4 (de) * | 2004-01-23 | 2008-01-24 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung von Toluylendiisocyanat-basierenden Isocyanurat-Polyisocyanatlösungen |
| US20080277106A1 (en) * | 2004-02-03 | 2008-11-13 | Atlas Copco Airpower | Heat Exchanger |
| DE102007034977A1 (de) | 2007-07-26 | 2009-01-29 | Lanxess Deutschland Gmbh | Phthalatfreie Isocyanuratzubereitungen |
| EP2028203A1 (de) | 2007-07-26 | 2009-02-25 | Lanxess Deutschland GmbH | Phthalatfreie Isocyanuratzubereitungen |
| WO2011095569A2 (de) | 2010-02-08 | 2011-08-11 | Lanxess Deutschland Gmbh | Phthalatfreie isocyanuratzubereitungen |
| EP2354172A1 (de) | 2010-02-08 | 2011-08-10 | LANXESS Deutschland GmbH | Phthalatfreie Isocyanuratzubereitungen |
| DE102010033061A1 (de) | 2010-08-02 | 2012-02-02 | Bayer Materialscience Ag | Phthalatfreie Isocyanuratzubereitung |
| WO2012016903A1 (de) | 2010-08-02 | 2012-02-09 | Lanxess Deutschland Gmbh | Phthalatfreie isocyanuratzubereitungen |
| EP3916031A1 (de) | 2020-05-28 | 2021-12-01 | LANXESS Deutschland GmbH | Neue phthalatfreie isocyanurat-zusammensetzung und deren verwendung |
| WO2021239621A1 (de) | 2020-05-28 | 2021-12-02 | Lanxess Deutschland Gmbh | Neue phthalatfreie isocyanurat-zusammensetzung und deren verwendung |
| EP3909994A1 (de) | 2021-02-18 | 2021-11-17 | LANXESS Deutschland GmbH | Neue phthalatfreie isocyanurat-zusammensetzung |
| WO2025131813A1 (de) | 2023-12-20 | 2025-06-26 | Lanxess Deutschland Gmbh | Neue phthalatfreie isocyanurat-zusammensetzung und deren verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0051239B1 (de) | 1985-01-02 |
| ZA817631B (en) | 1982-10-27 |
| JPH0116267B2 (https=) | 1989-03-23 |
| DK487681A (da) | 1982-05-06 |
| ATE11051T1 (de) | 1985-01-15 |
| ES8303491A1 (es) | 1983-02-01 |
| EP0051239A1 (de) | 1982-05-12 |
| DE3168076D1 (en) | 1985-02-14 |
| US4518729A (en) | 1985-05-21 |
| ES506843A0 (es) | 1983-02-01 |
| JPS57105441A (en) | 1982-06-30 |
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