CS128891A3 - Compositions on the base of unsaturated polyester resins and a novel anti-contraction additive - Google Patents

Compositions on the base of unsaturated polyester resins and a novel anti-contraction additive Download PDF

Info

Publication number: CS128891A3
Authority: CS; Czechoslovakia
Prior art keywords: resin compositions; liquid resin; unsaturated polyester; compositions according; alkyl methacrylate
Prior art date: 1990-05-04

Application number

CS911288A

Other languages

Czech (cs)

English (en)

Inventor

Dominique Fourquier

Laurent Suspene

Original Assignee

Cray Valley Sa

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.)

1990-05-04

Filing date

1991-05-03

Publication date

1992-01-15

1991-05-03 Application filed by Cray Valley Sa filed Critical Cray Valley Sa

1992-01-15 Publication of CS128891A3 publication Critical patent/CS128891A3/cs

Links

239000000203 mixture Substances 0.000 title description 59
229920006337 unsaturated polyester resin Polymers 0.000 title description 18
239000000654 additive Substances 0.000 title description 17
230000000996 additive effect Effects 0.000 title description 10
-1 hydroxylated alkyl methacrylate Chemical compound 0.000 claims abstract description 40
229920000642 polymer Polymers 0.000 claims abstract description 35
239000011342 resin composition Substances 0.000 claims abstract description 30
239000007788 liquid Substances 0.000 claims abstract description 21
239000000178 monomer Substances 0.000 claims abstract description 19
229920006305 unsaturated polyester Polymers 0.000 claims abstract description 17
239000003365 glass fiber Substances 0.000 claims abstract description 13
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 40
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 7
230000009477 glass transition Effects 0.000 claims description 7
150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 6
150000003440 styrenes Chemical class 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
239000004641 Diallyl-phthalate Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical class C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 3
229920001577 copolymer Polymers 0.000 claims description 3
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
URESCTIIPYNKAC-UHFFFAOYSA-N prop-2-enoic acid;prop-1-en-2-ylbenzene Chemical class OC(=O)C=C.CC(=C)C1=CC=CC=C1 URESCTIIPYNKAC-UHFFFAOYSA-N 0.000 claims 1
238000000465 moulding Methods 0.000 abstract description 18
238000004519 manufacturing process Methods 0.000 abstract description 3
238000002347 injection Methods 0.000 abstract 1
239000007924 injection Substances 0.000 abstract 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 14
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 12
229920003229 poly(methyl methacrylate) Polymers 0.000 description 12
229920005989 resin Polymers 0.000 description 12
239000011347 resin Substances 0.000 description 12
238000009472 formulation Methods 0.000 description 11
239000004926 polymethyl methacrylate Substances 0.000 description 11
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 10
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
229920001225 polyester resin Polymers 0.000 description 8
239000004645 polyester resin Substances 0.000 description 8
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
229910000019 calcium carbonate Inorganic materials 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
229920000193 polymethacrylate Polymers 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000006229 carbon black Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
238000001746 injection moulding Methods 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
229920001169 thermoplastic Polymers 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004412 Bulk moulding compound Substances 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
235000013539 calcium stearate Nutrition 0.000 description 2
239000008116 calcium stearate Substances 0.000 description 2
239000012986 chain transfer agent Substances 0.000 description 2
238000004040 coloring Methods 0.000 description 2
239000002131 composite material Substances 0.000 description 2
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000003999 initiator Substances 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000005395 methacrylic acid group Chemical group 0.000 description 2
KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 2
239000000049 pigment Substances 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
239000007870 radical polymerization initiator Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
238000010186 staining Methods 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
ZLUFYQVHJAVDHU-IHWYPQMZSA-N (6z)-2-methyl-2,3-dihydro-1,4-dioxocine-5,8-dione Chemical compound CC1COC(=O)\C=C/C(=O)O1 ZLUFYQVHJAVDHU-IHWYPQMZSA-N 0.000 description 1
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
RPBWMJBZQXCSFW-UHFFFAOYSA-N 2-methylpropanoyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(=O)C(C)C RPBWMJBZQXCSFW-UHFFFAOYSA-N 0.000 description 1
DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
XRUKRHLZDVJJSX-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical compound N#CC(C)CCC(O)=O XRUKRHLZDVJJSX-UHFFFAOYSA-N 0.000 description 1
XOJXZLAGXTXBEQ-UHFFFAOYSA-N 4-hydroxy-2-methylbutanenitrile Chemical compound N#CC(C)CCO XOJXZLAGXTXBEQ-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
WDPRYXKBIDOGEC-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.C=CC.C=CC Chemical compound C(C=CC(=O)O)(=O)O.C=CC.C=CC WDPRYXKBIDOGEC-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
238000005275 alloying Methods 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000003006 anti-agglomeration agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 description 1
XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000001879 gelation Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
229940091853 isobornyl acrylate Drugs 0.000 description 1
229940119545 isobornyl methacrylate Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229920003145 methacrylic acid copolymer Polymers 0.000 description 1
229940117841 methacrylic acid copolymer Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
239000012170 montan wax Substances 0.000 description 1
GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
239000005445 natural material Substances 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
UTOPWMOLSKOLTQ-UHFFFAOYSA-M octacosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O UTOPWMOLSKOLTQ-UHFFFAOYSA-M 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001299 polypropylene fumarate Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
238000005488 sandblasting Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
229940035024 thioglycerol Drugs 0.000 description 1
238000001721 transfer moulding Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Classifications

- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0478—Copolymers from unsaturated polyesters and low molecular monomers characterised by the monomers used
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Macromonomer-Based Addition Polymer (AREA)
Compositions Of Macromolecular Compounds (AREA)
Picture Signal Circuits (AREA)
Studio Devices (AREA)

CS911288A 1990-05-04 1991-05-03 Compositions on the base of unsaturated polyester resins and a novel anti-contraction additive CS128891A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9005631A FR2661682B1 (fr)	1990-05-04	1990-05-04	Nouvelles compositions resineuses a base de resines polyesters non saturees et de nouveaux additifs anti-retrait.

Publications (1)

Publication Number	Publication Date
CS128891A3 true CS128891A3 (en)	1992-01-15

Family

ID=9396326

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911288A CS128891A3 (en)	1990-05-04	1991-05-03	Compositions on the base of unsaturated polyester resins and a novel anti-contraction additive

Country Status (17)

Country	Link
US (1)	US5420179A (de)
EP (1)	EP0455544B1 (de)
JP (1)	JPH05505639A (de)
AT (1)	ATE155162T1 (de)
AU (1)	AU637492B2 (de)
CA (1)	CA2041781C (de)
CS (1)	CS128891A3 (de)
DE (1)	DE69126740T2 (de)
DK (1)	DK0455544T3 (de)
ES (1)	ES2106064T3 (de)
FR (1)	FR2661682B1 (de)
GR (1)	GR3024816T3 (de)
HR (1)	HRP920442B1 (de)
SI (1)	SI9110774B (de)
WO (1)	WO1991017214A1 (de)
YU (1)	YU77491A (de)
ZA (1)	ZA913323B (de)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2702215B1 (fr) *	1993-03-04	1995-04-14	Cray Valley Sa	Compositions de résines polyester insaturées et d'additifs anti-retrait.
FR2703062B1 (fr) *	1993-03-24	1995-05-12	Cray Valley Sa	Additifs anti-retrait pour résines polyesters insaturées.
JP3174271B2 (ja) *	1995-07-27	2001-06-11	株式会社小糸製作所	ランプ反射鏡用成形組成物、それを用いたランプ反射鏡の製造方法及びランプ反射鏡
US5731035A (en) *	1995-09-22	1998-03-24	Cook Composites And Polymers	Process for making a paintable polymer article
US5869154A (en) *	1996-03-21	1999-02-09	Fort James Corporation	Resin composition having special colors and decoration added thereto
US6124373A (en)	1998-04-10	2000-09-26	Wm. Marsh Rice University	Bone replacement compound comprising poly(polypropylene fumarate)
JP2002542349A (ja) *	1999-04-16	2002-12-10	ダブリューエム・マーシュ・ライス・ユニバーシティー	ポリ（プロピレンフマラート）−ジアクリレートマクロマーで交差結合された生体分解性のポリ（プロピレンフマラート）ネットワーク
WO2001018102A1 (en) *	1999-09-10	2001-03-15	Kt Holdings, Llc	Novel polymer additives for forming objects
US7629388B2 (en) *	2001-11-20	2009-12-08	William Marsh Rice University	Synthesis and characterization of biodegradable cationic poly(propylene fumarate-co-ethylene glycol) copolymer hydrogels modified with agmatine for enhanced cell adhesion
EP1483340A1 (de) *	2002-02-19	2004-12-08	Verdant Technologies, Inc.	Sprühbare in der gussform anwendbare gelförmige zusammensetzungen mit niedriger flüchtigkeit zur beschichtung
DE102004031968A1 (de) *	2004-07-01	2006-01-19	Wacker Polymer Systems Gmbh & Co. Kg	Mit Säuregruppen funktionalisierte Polyvinylacetat-Festharze
US20070083005A1 (en) *	2005-10-07	2007-04-12	Premix Inc.	Molding compositions for use in forward lighting applications and headlight components molded therefrom
US9828597B2 (en)	2006-11-22	2017-11-28	Toyota Motor Engineering & Manufacturing North America, Inc.	Biofunctional materials
US8563221B2 (en) *	2008-03-11	2013-10-22	3M Innovative Properties Company	Phototools having a protective layer
US10988714B2 (en)	2010-06-21	2021-04-27	Regents Of The University Of Minnesota	Methods of facilitating removal of a fingerprint from a substrate or a coating
US11015149B2 (en)	2010-06-21	2021-05-25	Toyota Motor Corporation	Methods of facilitating removal of a fingerprint
US9121016B2 (en)	2011-09-09	2015-09-01	Toyota Motor Engineering & Manufacturing North America, Inc.	Coatings containing polymer modified enzyme for stable self-cleaning of organic stains
US8796009B2 (en)	2010-06-21	2014-08-05	Toyota Motor Engineering & Manufacturing North America, Inc.	Clearcoat containing thermolysin-like protease from Bacillus stearothermophilus for cleaning of insect body stains
US9388370B2 (en)	2010-06-21	2016-07-12	Toyota Motor Engineering & Manufacturing North America, Inc.	Thermolysin-like protease for cleaning insect body stains
CN108353523B (zh) *	2015-11-25	2020-02-25	株式会社巴川制纸所	匹配型电磁波吸收体

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3701748A (en) *	1966-07-20	1972-10-31	Rohm & Haas	Unsaturated polyester resinous compositions
JPS4849884A (de) *	1971-10-27	1973-07-13
JPS5126960B2 (de) *	1971-10-28	1976-08-10
US3956421A (en) *	1974-12-12	1976-05-11	Owens-Corning Fiberglas Corporation	Polar thermoplastic additive for molding compounds and molding compound containing same
CA1188036A (en) *	1981-06-29	1985-05-28	Union Carbide Corporation	Curable molding compositions
US4579890A (en) *	1981-07-01	1986-04-01	Union Carbide Corporation	Curable molding compositions containing a polyester resin
US4626570A (en) *	1984-06-29	1986-12-02	Union Carbide Corporation	Low shrinking thermosetting polyester resin compositions and a process for the preparation thereof
FR2589473B1 (fr) *	1985-10-30	1988-09-16	Saint Gobain Vetrotex	Composition de resines polymerisables renforcee par des fils coupes

1990
- 1990-05-04 FR FR9005631A patent/FR2661682B1/fr not_active Expired - Fee Related
1991
- 1991-04-25 AT AT91401105T patent/ATE155162T1/de not_active IP Right Cessation
- 1991-04-25 JP JP91509100A patent/JPH05505639A/ja active Pending
- 1991-04-25 DK DK91401105.1T patent/DK0455544T3/da active
- 1991-04-25 WO PCT/FR1991/000347 patent/WO1991017214A1/fr not_active Ceased
- 1991-04-25 ES ES91401105T patent/ES2106064T3/es not_active Expired - Lifetime
- 1991-04-25 EP EP91401105A patent/EP0455544B1/de not_active Expired - Lifetime
- 1991-04-25 US US07/941,121 patent/US5420179A/en not_active Expired - Fee Related
- 1991-04-25 DE DE69126740T patent/DE69126740T2/de not_active Expired - Fee Related
- 1991-04-29 AU AU76211/91A patent/AU637492B2/en not_active Ceased
- 1991-04-29 YU YU77491A patent/YU77491A/sh unknown
- 1991-04-29 SI SI9110774A patent/SI9110774B/sl unknown
- 1991-05-02 ZA ZA913323A patent/ZA913323B/xx unknown
- 1991-05-03 CA CA002041781A patent/CA2041781C/fr not_active Expired - Fee Related
- 1991-05-03 CS CS911288A patent/CS128891A3/cs unknown
1992
- 1992-09-23 HR HRP-774/91A patent/HRP920442B1/xx not_active IP Right Cessation
1997
- 1997-09-24 GR GR970402450T patent/GR3024816T3/el unknown

Also Published As

Publication number	Publication date
US5420179A (en)	1995-05-30
FR2661682B1 (fr)	1993-12-10
AU637492B2 (en)	1993-05-27
HRP920442B1 (en)	2000-02-29
EP0455544A1 (de)	1991-11-06
FR2661682A1 (fr)	1991-11-08
DE69126740T2 (de)	1998-02-12
ATE155162T1 (de)	1997-07-15
WO1991017214A1 (fr)	1991-11-14
GR3024816T3 (en)	1998-01-30
CA2041781A1 (fr)	1991-11-05
SI9110774A (en)	1997-06-30
SI9110774B (sl)	2000-08-31
ZA913323B (en)	1993-04-28
EP0455544B1 (de)	1997-07-09
YU77491A (sh)	1994-05-10
CA2041781C (fr)	2002-12-10
AU7621191A (en)	1991-11-07
ES2106064T3 (es)	1997-11-01
DK0455544T3 (da)	1998-02-23
DE69126740D1 (de)	1997-08-14
JPH05505639A (ja)	1993-08-19
HRP920442A2 (en)	1995-10-31

Publication	Publication Date	Title
CS128891A3 (en)	1992-01-15	Compositions on the base of unsaturated polyester resins and a novel anti-contraction additive
US3701748A (en)	1972-10-31	Unsaturated polyester resinous compositions
US3772241A (en)	1973-11-13	Unsaturated polyester resinous compositions
NO137322B (no)	1977-10-31	Polymere, formede gjenstander samt fortykkbar, polymeriserbar st¦peblanding for anvendelse ved fremstilling av slike gjenstander.
US3810863A (en)	1974-05-14	Polymerizable unsaturated polyester resin compositions and articles made therefrom
US3318975A (en)	1967-05-09	Mar-resistant polyesters
US4172102A (en)	1979-10-23	Low-shrink unsaturated polyester molding compositions
KR20010051060A (ko)	2001-06-25	불포화 폴리에스테르 수지 및 성형 재료용 조성물
US3665055A (en)	1972-05-23	Polymerizable unsaturated polyester resin compositions and articles made therefrom
US3042651A (en)	1962-07-03	Polymerizable composition containing unsaturated polyester, an acrylic ester, a monovinyl benzene and a vinyl ester of an alkyl carboxylic acid
US4049749A (en)	1977-09-20	Pigmentable low-profile polyester molding compositions
US4131635A (en)	1978-12-26	Thermosetting polyester compositions
JPS61166850A (ja)	1986-07-28	不飽和ポリエステル樹脂組成物
JPS6372513A (ja)	1988-04-02	繊維強化樹脂成形品の成形方法およびそれに使用する不飽和ポリエステル樹脂組成物
JP2859070B2 (ja)	1999-02-17	浴槽成形用不飽和ポリエステル樹脂組成物
KR20010051002A (ko)	2001-06-25	투명도가 높은 성형품을 얻을 수 있는 시트형 성형 재료및 그 성형품
JPH11172092A (ja)	1999-06-29	不飽和ポリエステル樹脂組成物
JPH0632920A (ja)	1994-02-08	熱硬化性樹脂プリプレグ
JPH04198209A (ja)	1992-07-17	ジシクロペンタジエン変性不飽和ポリエステル組成物及びその使用
JPS5846206B2 (ja)	1983-10-14	ポリエステル樹脂組成物
JPH04507105A (ja)	1992-12-10	クエン酸エステル組成物及びその製造方法
JPS582315A (ja)	1983-01-07	不飽和ポリエステル樹脂組成物
JPH0337257A (ja)	1991-02-18	低収縮性不飽和ポリエステル樹脂組成物
JPS6357619A (ja)	1988-03-12	繊維強化樹脂成形品の成形方法およびそれに使用する不飽和ポリエステル樹脂組成物
JPH02296862A (ja)	1990-12-07	硬化時のチョーキングが抑制された液状の低収縮性不飽和ポリエステル樹脂組成物