CA1165993A - Antioxydants et polymeres renforces; emulsions, d'huile dans l'eau, d'antioxydants - Google Patents

Antioxydants et polymeres renforces; emulsions, d'huile dans l'eau, d'antioxydants

Info

Publication number: CA1165993A
Authority: CA; Canada
Prior art keywords: antioxidant; emulsion; weight percent; glass fibers; amount
Prior art date: 1980-04-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000365047A

Other languages

English (en)

Inventor

Albert E. Tamosauskas

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

PPG Industries Ohio Inc

Original Assignee

PPG Industries Inc

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.)

1980-04-03

Filing date

1980-11-19

Publication date

1984-04-24

1980-11-19 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1984-04-24 Application granted granted Critical

1984-04-24 Publication of CA1165993A publication Critical patent/CA1165993A/fr

Status Expired legal-status Critical Current

Links

239000003963 antioxidant agent Substances 0.000 title claims abstract description 201
239000000839 emulsion Substances 0.000 title claims abstract description 149
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 82
229920000642 polymer Polymers 0.000 title claims abstract description 77
239000000203 mixture Substances 0.000 claims abstract description 209
230000003078 antioxidant effect Effects 0.000 claims abstract description 169
239000003995 emulsifying agent Substances 0.000 claims abstract description 121
239000003365 glass fiber Substances 0.000 claims abstract description 80
238000004513 sizing Methods 0.000 claims abstract description 56
-1 film-former Substances 0.000 claims abstract description 52
239000000463 material Substances 0.000 claims abstract description 36
239000003960 organic solvent Substances 0.000 claims abstract description 36
239000007764 o/w emulsion Substances 0.000 claims abstract description 32
230000002787 reinforcement Effects 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 31
238000002144 chemical decomposition reaction Methods 0.000 claims abstract description 21
239000003822 epoxy resin Substances 0.000 claims abstract description 21
229920000647 polyepoxide Polymers 0.000 claims abstract description 21
239000007822 coupling agent Substances 0.000 claims abstract description 15
238000006243 chemical reaction Methods 0.000 claims abstract description 11
238000003878 thermal aging Methods 0.000 claims abstract description 11
238000009835 boiling Methods 0.000 claims abstract description 10
229920005989 resin Polymers 0.000 claims abstract description 8
239000011347 resin Substances 0.000 claims abstract description 8
125000000129 anionic group Chemical group 0.000 claims abstract description 7
229920005862 polyol Polymers 0.000 claims abstract description 6
150000003077 polyols Chemical class 0.000 claims abstract description 6
238000000354 decomposition reaction Methods 0.000 claims abstract description 5
229920001281 polyalkylene Polymers 0.000 claims abstract description 4
230000004224 protection Effects 0.000 claims abstract description 4
235000006708 antioxidants Nutrition 0.000 claims description 192
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 44
239000002904 solvent Substances 0.000 claims description 34
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 31
239000000126 substance Substances 0.000 claims description 26
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
230000015556 catabolic process Effects 0.000 claims description 19
238000006731 degradation reaction Methods 0.000 claims description 19
239000002245 particle Substances 0.000 claims description 17
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 16
239000000314 lubricant Substances 0.000 claims description 16
238000009472 formulation Methods 0.000 claims description 15
230000003993 interaction Effects 0.000 claims description 15
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 14
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 14
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 13
239000011521 glass Substances 0.000 claims description 13
239000007787 solid Substances 0.000 claims description 13
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
239000012875 nonionic emulsifier Substances 0.000 claims description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
239000000047 product Substances 0.000 claims description 12
235000015112 vegetable and seed oil Nutrition 0.000 claims description 10
239000008158 vegetable oil Substances 0.000 claims description 10
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 8
125000005266 diarylamine group Chemical group 0.000 claims description 8
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 claims description 7
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclo-pentanone Natural products O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 7
229940035422 diphenylamine Drugs 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
229940035044 sorbitan monolaurate Drugs 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 6
238000005755 formation reaction Methods 0.000 claims description 6
230000002209 hydrophobic effect Effects 0.000 claims description 6
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 6
239000004593 Epoxy Substances 0.000 claims description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
150000002170 ethers Chemical class 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 5
241000592335 Agathis australis Species 0.000 claims description 4
238000001035 drying Methods 0.000 claims description 4
UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 claims description 4
229920001451 polypropylene glycol Polymers 0.000 claims description 4
238000012545 processing Methods 0.000 claims description 4
238000005979 thermal decomposition reaction Methods 0.000 claims description 4
230000004580 weight loss Effects 0.000 claims description 4
239000008096 xylene Substances 0.000 claims description 4
239000002530 phenolic antioxidant Substances 0.000 claims description 3
239000011877 solvent mixture Substances 0.000 claims description 3
238000002411 thermogravimetry Methods 0.000 claims description 3
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
229940117927 ethylene oxide Drugs 0.000 claims 3
BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical group O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 claims 1
239000002861 polymer material Substances 0.000 claims 1
FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims 1
230000000087 stabilizing effect Effects 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 5
239000003381 stabilizer Substances 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 3
239000000835 fiber Substances 0.000 abstract description 3
239000000243 solution Substances 0.000 description 22
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
238000007792 addition Methods 0.000 description 17
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
229920002066 Pluronic® P 65 Polymers 0.000 description 10
KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000007859 condensation product Substances 0.000 description 9
229920000126 latex Polymers 0.000 description 8
238000012360 testing method Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229920002430 Fibre-reinforced plastic Polymers 0.000 description 7
229920001707 polybutylene terephthalate Polymers 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229920002023 Pluronic® F 87 Polymers 0.000 description 6
230000032683 aging Effects 0.000 description 6
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 6
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 6
238000009826 distribution Methods 0.000 description 6
239000011151 fibre-reinforced plastic Substances 0.000 description 6
239000002657 fibrous material Substances 0.000 description 6
239000004816 latex Substances 0.000 description 6
229920000136 polysorbate Polymers 0.000 description 6
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 5
UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 5
229920002166 Pluracol® V 10 Polymers 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
229920001983 poloxamer Polymers 0.000 description 5
238000003860 storage Methods 0.000 description 5
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 5
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
239000004698 Polyethylene Substances 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 4
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
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239000011369 resultant mixture Substances 0.000 description 4
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ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 3
PLFJWWUZKJKIPZ-UHFFFAOYSA-N 2-[2-[2-(2,6,8-trimethylnonan-4-yloxy)ethoxy]ethoxy]ethanol Chemical compound CC(C)CC(C)CC(CC(C)C)OCCOCCOCCO PLFJWWUZKJKIPZ-UHFFFAOYSA-N 0.000 description 3
BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
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WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
AHKRMDMQOAEIKN-UHFFFAOYSA-N 2-benzyl-3-methylphenol Chemical compound CC1=CC=CC(O)=C1CC1=CC=CC=C1 AHKRMDMQOAEIKN-UHFFFAOYSA-N 0.000 description 2
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239000004215 Carbon black (E152) Substances 0.000 description 2
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WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
JZLWSRCQCPAUDP-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-triamine;urea Chemical compound NC(N)=O.NC1=NC(N)=NC(N)=N1 JZLWSRCQCPAUDP-UHFFFAOYSA-N 0.000 description 1
WYZIVNCBUWDCOZ-UHFFFAOYSA-N 2-(1-phenylethyl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1 WYZIVNCBUWDCOZ-UHFFFAOYSA-N 0.000 description 1
VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
YJCGDTJZLYIZRY-UHFFFAOYSA-N 2-benzyl-3,4-dimethylphenol Chemical compound CC1=CC=C(O)C(CC=2C=CC=CC=2)=C1C YJCGDTJZLYIZRY-UHFFFAOYSA-N 0.000 description 1
NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
VDRHHMJLYVHYDO-UHFFFAOYSA-N 2-hydroxyethyl 7-(3-tert-butyl-4-hydroxy-5-methylphenyl)heptanoate Chemical compound CC1=CC(CCCCCCC(=O)OCCO)=CC(C(C)(C)C)=C1O VDRHHMJLYVHYDO-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 1
WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
FJDLQLIRZFKEKJ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanamide Chemical compound CC(C)(C)C1=CC(CCC(N)=O)=CC(C(C)(C)C)=C1O FJDLQLIRZFKEKJ-UHFFFAOYSA-N 0.000 description 1
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 1
VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
206010022528 Interactions Diseases 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
239000004640 Melamine resin Substances 0.000 description 1
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
235000008098 Oxalis acetosella Nutrition 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229920003265 Resimene® Polymers 0.000 description 1
244000126309 Trifolium dubium Species 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
239000012874 anionic emulsifier Substances 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000002238 attenuated effect Effects 0.000 description 1
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
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 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
125000003636 chemical group Chemical group 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000012612 commercial material Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
229910003460 diamond Inorganic materials 0.000 description 1
239000010432 diamond Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
239000006066 glass batch Substances 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000005484 gravity Effects 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229920005669 high impact polystyrene Polymers 0.000 description 1
239000004797 high-impact polystyrene Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000004579 marble Substances 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
238000012667 polymer degradation Methods 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920006264 polyurethane film Polymers 0.000 description 1
239000010734 process oil Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
150000003445 sucroses Chemical class 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/24—Coatings containing organic materials
- C03C25/26—Macromolecular compounds or prepolymers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
- C08J5/08—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials glass fibres
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/10—Reinforcing macromolecular compounds with loose or coherent fibrous material characterised by the additives used in the polymer mixture
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/16—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen
- C09K15/18—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen containing an amine or imine moiety

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Manufacturing & Machinery (AREA)
Life Sciences & Earth Sciences (AREA)
General Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Geochemistry & Mineralogy (AREA)
Compositions Of Macromolecular Compounds (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Reinforced Plastic Materials (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Surface Treatment Of Glass Fibres Or Filaments (AREA)

CA000365047A 1980-04-03 1980-11-19 Antioxydants et polymeres renforces; emulsions, d'huile dans l'eau, d'antioxydants Expired CA1165993A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13706380A	1980-04-03	1980-04-03
US137,063		1980-04-03

Publications (1)

Publication Number	Publication Date
CA1165993A true CA1165993A (fr)	1984-04-24

Family

ID=22475676

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000365047A Expired CA1165993A (fr)	1980-04-03	1980-11-19	Antioxydants et polymeres renforces; emulsions, d'huile dans l'eau, d'antioxydants

Country Status (9)

Country	Link
JP (1)	JPS5928587B2 (fr)
BE (1)	BE886942A (fr)
CA (1)	CA1165993A (fr)
CH (1)	CH651843A5 (fr)
DE (2)	DE3047503C2 (fr)
FR (2)	FR2479836B1 (fr)
GB (1)	GB2078270B (fr)
IT (1)	IT1129941B (fr)
NL (1)	NL8006696A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20060147707A1 (en) *	2004-12-30	2006-07-06	Jian Meng	Compacted, chopped fiber glass strands
EP2580053A1 (fr) *	2010-06-14	2013-04-17	E.I. Du Pont De Nemours And Company	Structures composites de polyester résistant à une exposition de longue durée aux intempéries et leurs procédés de préparation
CN113308020A (zh) *	2021-04-22	2021-08-27	长春工业大学	一种水性抗氧剂乳液及其制备方法和应用
US20250179295A1 (en) *	2023-11-30	2025-06-05	Hanwha Totalenergies Petrochemical Co., Ltd.	Flame-Retardant Polyester Resin Composite Composition And Article Molded Therefrom

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2717880A (en) *	1951-09-07	1955-09-13	Shell Dev	Alkyl phenol emulsions and process for preparing the same
NL274696A (fr) *	1961-02-13
NL284832A (fr) *	1961-10-30
US3290392A (en) *	1963-11-12	1966-12-06	Ethyl Corp	Ortho-alkylated phenols
US3285855A (en) *	1965-03-11	1966-11-15	Geigy Chem Corp	Stabilization of organic material with esters containing an alkylhydroxy-phenyl group
US3484223A (en) *	1965-09-08	1969-12-16	Exxon Research Engineering Co	Method for sizing glass fibers
US3506476A (en) *	1966-08-15	1970-04-14	Owens Corning Fiberglass Corp	Glass fiber-elastomeric products and method
CA983048A (en) *	1971-06-21	1976-02-03	Hooker Chemicals And Plastics Corp.	Antidegradant
JPS498511A (fr) *	1972-05-17	1974-01-25
JPS4916773A (fr) *	1972-06-02	1974-02-14
JPS5124653A (ja) *	1974-08-26	1976-02-28	Teijin Ltd	Horiesuterusoseibutsu
JPS5130254A (ja) *	1974-09-09	1976-03-15	Teijin Ltd	Horiesuterusoseibutsu
DE2550852A1 (de) *	1974-11-25	1976-05-26	Ici Ltd	Antioxidationsmittel
JPS5253971A (en) *	1975-10-29	1977-04-30	Fuji Fibre Glass Co Ltd	Treated glass fiber for reinforcing thermal setting resin and its manufacture
US4134841A (en) *	1978-03-10	1979-01-16	Union Carbide Corporation	Fiber lubricants

1980
- 1980-11-19 CA CA000365047A patent/CA1165993A/fr not_active Expired
- 1980-12-09 IT IT68873/80A patent/IT1129941B/it active
- 1980-12-10 NL NL8006696A patent/NL8006696A/nl not_active Application Discontinuation
- 1980-12-17 DE DE3047503A patent/DE3047503C2/de not_active Expired
- 1980-12-17 DE DE3050872A patent/DE3050872C2/de not_active Expired
- 1980-12-18 CH CH9357/80A patent/CH651843A5/fr not_active IP Right Cessation
- 1980-12-20 JP JP55181176A patent/JPS5928587B2/ja not_active Expired
- 1980-12-23 FR FR8027377A patent/FR2479836B1/fr not_active Expired
- 1980-12-31 BE BE0/203385A patent/BE886942A/fr not_active IP Right Cessation
1981
- 1981-03-06 GB GB8107038A patent/GB2078270B/en not_active Expired
- 1981-05-20 FR FR8110074A patent/FR2479843B1/fr not_active Expired

Also Published As

Publication number	Publication date
NL8006696A (nl)	1981-11-02
BE886942A (fr)	1981-06-30
JPS56141353A (en)	1981-11-05
IT1129941B (it)	1986-06-11
GB2078270A (en)	1982-01-06
FR2479836B1 (fr)	1986-03-21
FR2479843B1 (fr)	1985-10-04
JPS5928587B2 (ja)	1984-07-13
GB2078270B (en)	1984-09-19
FR2479836A1 (fr)	1981-10-09
DE3047503A1 (de)	1981-10-08
DE3050872C2 (de)	1985-08-22
CH651843A5 (fr)	1985-10-15
FR2479843A1 (fr)	1981-10-09
IT8068873A0 (it)	1980-12-09
DE3047503C2 (de)	1985-03-07

Legal Events

Date	Code	Title	Description
2001-04-24	MKEX	Expiry

Publication	Publication Date	Title
US4341677A (en)	1982-07-27	Antioxidants and reinforced polymers and oil-in-water emulsions of antioxidants
US4483948A (en)	1984-11-20	Antioxidants and reinforced polymers and oil-in-water emulsions of antioxidants
CA1153841A (fr)	1983-09-13	Composition d'une emulsion et methode destinees au traitement de la fibre de verre
CA1187234A (fr)	1985-05-14	Composition aqueuse de calibrage pour fibres de verre; utilisation de ces fibres pour le renforcement de matieres thermoplastiques
EP0116871B1 (fr)	1986-09-17	Procédé de préparation d'une composition aqueuse adhésive
US4752527A (en)	1988-06-21	Chemically treated glass fibers for reinforcing polymeric materials processes
US5130198A (en)	1992-07-14	Polymeric-containing compositions with improved oxidative stability
AU678825B2 (en)	1997-06-12	Elastomer/aramid fiber dispersion
US4283322A (en)	1981-08-11	Emulsion composition and method for use in treating glass fibers
AU592972B2 (en)	1990-02-01	Aqueous additive systems, methods and polymeric particles
EP0526546B1 (fr)	1996-07-17	Systemes d'additifs se presentant sous forme solide et se dispersant dans des milieux aqueux, procedes concernant leur preparation et leur application sur des particules polymeres
CA2120018C (fr)	1997-12-23	Additifs sous forme solides, dispersables dans des milieux aqueux et methode pour les preparer
US4960644A (en)	1990-10-02	Aqueous additive systems, methods and polymeric particles
US5096493A (en)	1992-03-17	Aqueous additive systems, methods and polymeric particles
CA1335136C (fr)	1995-04-04	Systemes aqueux d'application d'additifs, methodes pour la preparation d'emulsions aqueuses et particules polymeriques
CA1336123C (fr)	1995-07-04	Systemes d'additifs aqueux, methodes et particules polymeriques
GB2326164A (en)	1998-12-16	Emulsions of functionalized polyolefins
US5204022A (en)	1993-04-20	Solid-form additive systems dispersible in aqueous media
GB2078270A (en)	1982-01-06	Antioxidants and reinforced polymers and oil-in-water emulsions of antioxidants
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