DE2715294A1 - Formmassen und verfahren zur herstellung von formbaren vorkoerpern und formkoerpern - Google Patents
Formmassen und verfahren zur herstellung von formbaren vorkoerpern und formkoerpernInfo
- Publication number
- DE2715294A1 DE2715294A1 DE19772715294 DE2715294A DE2715294A1 DE 2715294 A1 DE2715294 A1 DE 2715294A1 DE 19772715294 DE19772715294 DE 19772715294 DE 2715294 A DE2715294 A DE 2715294A DE 2715294 A1 DE2715294 A1 DE 2715294A1
- Authority
- DE
- Germany
- Prior art keywords
- ethylenically unsaturated
- polyester
- resin
- composition according
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000465 moulding Methods 0.000 title claims description 40
- 150000001875 compounds Chemical class 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title description 13
- 239000000203 mixture Substances 0.000 claims description 55
- 239000000178 monomer Substances 0.000 claims description 47
- 229920005989 resin Polymers 0.000 claims description 35
- 239000011347 resin Substances 0.000 claims description 35
- 229920000728 polyester Polymers 0.000 claims description 30
- 229920001225 polyester resin Polymers 0.000 claims description 29
- 150000004985 diamines Chemical class 0.000 claims description 25
- 239000000945 filler Substances 0.000 claims description 23
- 229920006305 unsaturated polyester Polymers 0.000 claims description 18
- 125000005442 diisocyanate group Chemical group 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 150000002009 diols Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 229920002635 polyurethane Polymers 0.000 claims description 13
- 239000004814 polyurethane Substances 0.000 claims description 13
- 239000003365 glass fiber Substances 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 10
- 229920005749 polyurethane resin Polymers 0.000 claims description 10
- 239000002657 fibrous material Substances 0.000 claims description 8
- 229920001228 polyisocyanate Polymers 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 38
- 238000002360 preparation method Methods 0.000 description 33
- 239000000463 material Substances 0.000 description 25
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000012948 isocyanate Substances 0.000 description 20
- 150000002513 isocyanates Chemical class 0.000 description 19
- 239000004645 polyester resin Substances 0.000 description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
- 239000011521 glass Substances 0.000 description 16
- 239000000499 gel Substances 0.000 description 15
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- 239000002562 thickening agent Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 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 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- -1 saturated aliphatic diols Chemical class 0.000 description 12
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 11
- 239000000835 fiber Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 8
- 235000011037 adipic acid Nutrition 0.000 description 7
- 239000001361 adipic acid Substances 0.000 description 7
- 238000005266 casting Methods 0.000 description 7
- 238000001879 gelation Methods 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 229940093476 ethylene glycol Drugs 0.000 description 4
- 239000008240 homogeneous mixture Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 3
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 3
- 229960001826 dimethylphthalate Drugs 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 2
- 235000012245 magnesium oxide Nutrition 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical class [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000582 polyisocyanurate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical class C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 1
- XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- BNCFLKMOWWGLCR-UHFFFAOYSA-N 4-(4-amino-2-chlorophenyl)sulfonyl-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1Cl BNCFLKMOWWGLCR-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- XIZHZKHLXXCEMF-UHFFFAOYSA-N 4-[2-(4-amino-2-chlorophenyl)propan-2-yl]-3-chloroaniline Chemical compound C=1C=C(N)C=C(Cl)C=1C(C)(C)C1=CC=C(N)C=C1Cl XIZHZKHLXXCEMF-UHFFFAOYSA-N 0.000 description 1
- UHNUHZHQLCGZDA-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethyl]aniline Chemical group C1=CC(N)=CC=C1CCC1=CC=C(N)C=C1 UHNUHZHQLCGZDA-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- HQDCQNCMUSAKQU-UHFFFAOYSA-N 4-bromobenzene-1,3-diamine Chemical compound NC1=CC=C(Br)C(N)=C1 HQDCQNCMUSAKQU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- 239000004342 Benzoyl peroxide Substances 0.000 description 1
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- 241000143476 Bidens Species 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- 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 1
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- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
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- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
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- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C08L75/04—Polyurethanes
- C08L75/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
-
- 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
- C08G18/86—Chemically modified polymers by peroxides
-
- 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
- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
- Graft Or Block Polymers (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/676,531 US4073828A (en) | 1976-04-12 | 1976-04-12 | Ethylenically unsaturated monomer solutions containing urylated linear polyester/polyurethane resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2715294A1 true DE2715294A1 (de) | 1977-10-27 |
Family
ID=24714908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772715294 Ceased DE2715294A1 (de) | 1976-04-12 | 1977-04-05 | Formmassen und verfahren zur herstellung von formbaren vorkoerpern und formkoerpern |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4073828A (enExample) |
| JP (1) | JPS52124052A (enExample) |
| BE (1) | BE853514A (enExample) |
| BR (1) | BR7702154A (enExample) |
| CA (1) | CA1070882A (enExample) |
| DE (1) | DE2715294A1 (enExample) |
| FR (1) | FR2348246A1 (enExample) |
| GB (1) | GB1573525A (enExample) |
| IT (1) | IT1125733B (enExample) |
| MX (1) | MX151211A (enExample) |
| NL (1) | NL7703955A (enExample) |
| SE (1) | SE437528B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0028470A3 (en) * | 1979-10-29 | 1981-08-26 | Ici Americas Inc | Solutions of resins in a monomer, containing polyamine reactable with isocyanates, moulding compositions and cured product thereof |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1422778A (en) * | 1972-04-10 | 1976-01-28 | Ici Ltd | Shaped polymeric articles |
| DE2719149A1 (de) * | 1977-04-29 | 1978-11-09 | Bayer Ag | Verfahren zur herstellung von perlpolymeren |
| DE2741196A1 (de) * | 1977-09-13 | 1979-03-15 | Bayer Ag | Verfahren zur herstellung von perlpolymeren |
| DE2752611A1 (de) * | 1977-11-25 | 1979-06-07 | Bayer Ag | Dentalformkoerper |
| US4242415A (en) * | 1978-12-26 | 1980-12-30 | Ici Americas Inc. | In-mold coating compositions containing functional group terminated liquid polymers |
| US4296215A (en) * | 1978-07-27 | 1981-10-20 | Ici Americas Inc. | Method to thicken dissolved thermoset resins |
| US4232133A (en) * | 1978-07-27 | 1980-11-04 | Ici Americas Inc. | Polyisocyanurate containing molding compositions |
| EP0016248B1 (en) * | 1978-10-24 | 1984-02-15 | Dainippon Ink And Chemicals, Inc. | Method for producing prepreg rovings and method for producing fibre reinforced plastic articles |
| US4421894A (en) * | 1979-03-02 | 1983-12-20 | Olin Corporation | Polyurethane oligomer impact and shrinkage modifiers for thermoset polyesters |
| CA1164142A (en) * | 1979-05-22 | 1984-03-20 | Ici Americas Inc. | Polyester urethane-containing molding compositions |
| JPS5667322A (en) * | 1979-11-05 | 1981-06-06 | Showa Highpolymer Co Ltd | Curable resin composition |
| US4289682A (en) * | 1979-12-26 | 1981-09-15 | Union Carbide Corporation | Curable resin compositions comprising hydroxyl-terminated unsaturated polyester oligomer, a polyisocyanate, an ethylenically unsaturated monomer and a catalyst |
| US4289684A (en) * | 1980-04-23 | 1981-09-15 | Freeman Chemical Corporation | Sheet molding compound |
| US4348503A (en) * | 1980-06-04 | 1982-09-07 | Bachmann Andrew G | Adhesive composition |
| EP0085722A4 (en) * | 1981-08-19 | 1983-12-23 | Sony Corp | Electron beam-curable resin. |
| US4425468A (en) | 1981-12-31 | 1984-01-10 | Ppg Industries, Inc. | Polyurea-polyurethane acrylate polymer dispersions |
| US4555551A (en) * | 1981-12-31 | 1985-11-26 | Ppg Industries, Inc. | Method of molding |
| US4880872A (en) * | 1986-04-03 | 1989-11-14 | Ici Americas Inc. | Heat resistant high modulus reaction injection molding (RIM) polymers, blends used in the production thereof and a process for producing the same |
| DE3613790A1 (de) * | 1986-04-24 | 1987-10-29 | Bayer Ag | Verfahren zur herstellung von thermoplastischen polyurethanen fuer die strahlenvernetzung und ihre verwendung |
| US5494741A (en) * | 1986-12-12 | 1996-02-27 | Frank Fekete | Time delayed thickening, slump-resistant polymer concrete compositions, methods of repairing concrete surfaces, concrete structures repaired therewith and articles of construction comprising a formed mass of said compositions in cured condition |
| US5242708A (en) * | 1986-12-12 | 1993-09-07 | Frank Fekete | Time delayed thickening slump-resistant polymer concrete composition, methods of repairing concrete surfaces, concrete structures repaired therewith and articles of construction comprising a formed mass of said compositions in cured condition |
| DE3731067A1 (de) * | 1987-09-16 | 1989-04-06 | Basf Ag | Eingedickte formmassen |
| US4868231A (en) * | 1988-05-27 | 1989-09-19 | Gencorp Inc. | Thickened molding resin compositions and cured molded compounds |
| JP2686682B2 (ja) * | 1991-10-16 | 1997-12-08 | いすゞ自動車株式会社 | 成形品の製造方法 |
| US6692802B1 (en) * | 1997-08-27 | 2004-02-17 | Reichhold, Inc. | Resins for lining surfaces |
| US5925409A (en) * | 1997-08-27 | 1999-07-20 | Reichhold, Inc. | Resins for lining surfaces |
| CN1170869C (zh) * | 1998-10-15 | 2004-10-13 | 托马斯·布彻尔 | 聚氨酯材料模制体及其制备方法和应用 |
| US6727320B2 (en) * | 1998-11-02 | 2004-04-27 | Henkel Loctite Corporation | Polymerizable compositions in non-flowable forms |
| US20050182205A1 (en) * | 2004-02-17 | 2005-08-18 | Guha Probir K. | Polymeric thickener for molding compounds |
| US7829637B2 (en) * | 2004-02-17 | 2010-11-09 | Continental Structural Plastics | Polymeric thickener for molding compounds |
| US20050191468A1 (en) * | 2004-02-27 | 2005-09-01 | Neil Sater | Contoured laminated slate and method for production thereof |
| US10102946B1 (en) | 2015-10-09 | 2018-10-16 | Superior Essex International LP | Methods for manufacturing discontinuous shield structures for use in communication cables |
| US11214679B2 (en) | 2016-04-20 | 2022-01-04 | Continental Structural Plastics, Inc. | High strength sheet molding composition formed with an interpenetrating polymer network |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2912418A (en) * | 1955-10-07 | 1959-11-10 | Peterlite Products Ltd | Method of preparing moulded article from polymerisable materials |
| US3377406A (en) * | 1963-12-16 | 1968-04-09 | Shell Oil Co | Process of esterification of polyepoxides with ethylenically unsaturated monocarboxylic acids in the presence of onium salts of inorganic acids |
| US3509234A (en) * | 1965-08-13 | 1970-04-28 | Ford Motor Co | Radiation curable paint binders containing vinyl monomers and a hydroxylated polymer reacted with a polyisocyanate and an hydroxyl alkyl acrylate |
| US3644569A (en) * | 1968-11-19 | 1972-02-22 | American Cyanamid Co | Two-part adhesives comprising an isocyanate terminated prepolymer an isocyanate reactive monomer and an unsaturated polyester |
| GB1239701A (enExample) * | 1969-01-27 | 1971-07-21 | Ici Ltd | |
| US3641199A (en) * | 1969-07-07 | 1972-02-08 | Rohm & Haas | Urethane elastomer with active hydrogen containing monoethylenical unsaturated monomer |
| US3886229A (en) * | 1969-08-21 | 1975-05-27 | Ici Ltd | Shaped polymeric articles |
| US3962370A (en) * | 1970-12-11 | 1976-06-08 | Imperial Chemical Industries Limited | Shaped polymeric articles |
| BE795641A (fr) * | 1972-02-23 | 1973-08-20 | Ici Ltd | Compositions a mouler |
| US3868431A (en) * | 1972-05-16 | 1975-02-25 | Ici Ltd | Elastomer production |
| US3893956A (en) * | 1972-12-11 | 1975-07-08 | August Merckens Nachfolger Kom | Thixotropic coating agents based on urea adduct of polyamine and diisocyanates |
| US3859381A (en) * | 1973-04-19 | 1975-01-07 | Ici Ltd | Crosslinked polyurethanes from polyurethane precursors and vinyl monomers |
| JPS535917B2 (enExample) * | 1973-12-29 | 1978-03-02 | ||
| JPS538354B2 (enExample) * | 1974-02-15 | 1978-03-28 | ||
| US3994764A (en) * | 1975-06-13 | 1976-11-30 | Pratt & Lambert, Inc. | Adhesive compositions |
-
1976
- 1976-04-12 US US05/676,531 patent/US4073828A/en not_active Expired - Lifetime
-
1977
- 1977-02-25 CA CA272,727A patent/CA1070882A/en not_active Expired
- 1977-03-28 GB GB12917/77A patent/GB1573525A/en not_active Expired
- 1977-04-04 MX MX168626A patent/MX151211A/es unknown
- 1977-04-05 BR BR7702154A patent/BR7702154A/pt unknown
- 1977-04-05 DE DE19772715294 patent/DE2715294A1/de not_active Ceased
- 1977-04-06 SE SE7704056A patent/SE437528B/xx not_active IP Right Cessation
- 1977-04-07 JP JP3990777A patent/JPS52124052A/ja active Granted
- 1977-04-08 IT IT22332/77A patent/IT1125733B/it active
- 1977-04-12 BE BE176643A patent/BE853514A/xx not_active IP Right Cessation
- 1977-04-12 NL NL7703955A patent/NL7703955A/xx not_active Application Discontinuation
- 1977-04-12 FR FR7710997A patent/FR2348246A1/fr active Granted
- 1977-12-06 US US05/857,917 patent/US4129641A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0028470A3 (en) * | 1979-10-29 | 1981-08-26 | Ici Americas Inc | Solutions of resins in a monomer, containing polyamine reactable with isocyanates, moulding compositions and cured product thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US4073828A (en) | 1978-02-14 |
| FR2348246A1 (fr) | 1977-11-10 |
| GB1573525A (en) | 1980-08-28 |
| JPS571530B2 (enExample) | 1982-01-12 |
| SE7704056L (sv) | 1977-10-13 |
| US4129641A (en) | 1978-12-12 |
| CA1070882A (en) | 1980-01-29 |
| NL7703955A (nl) | 1977-10-14 |
| BR7702154A (pt) | 1978-10-31 |
| FR2348246B1 (enExample) | 1983-12-23 |
| SE437528B (sv) | 1985-03-04 |
| MX151211A (es) | 1984-10-11 |
| JPS52124052A (en) | 1977-10-18 |
| IT1125733B (it) | 1986-05-14 |
| BE853514A (fr) | 1977-10-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C08L 75/06 |
|
| 8131 | Rejection |