DE1032919B - Verfahren zur Herstellung einer lagerfaehigen, aushaertbaren Polyestermasse - Google Patents
Verfahren zur Herstellung einer lagerfaehigen, aushaertbaren PolyestermasseInfo
- Publication number
- DE1032919B DE1032919B DEU4420A DEU0004420A DE1032919B DE 1032919 B DE1032919 B DE 1032919B DE U4420 A DEU4420 A DE U4420A DE U0004420 A DEU0004420 A DE U0004420A DE 1032919 B DE1032919 B DE 1032919B
- Authority
- DE
- Germany
- Prior art keywords
- copper
- salts
- resin
- polyester
- inhibitors
- 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.)
- Pending
Links
- 229920000728 polyester Polymers 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims 4
- 239000003112 inhibitor Substances 0.000 claims description 29
- 239000005749 Copper compound Substances 0.000 claims description 19
- 150000001880 copper compounds Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229940120693 copper naphthenate Drugs 0.000 claims description 8
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 claims description 8
- -1 amine salts Chemical class 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical group [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 claims description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 4
- 150000004714 phosphonium salts Chemical group 0.000 claims description 3
- 150000004053 quinones Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 239000011152 fibreglass Substances 0.000 claims 1
- 230000002028 premature Effects 0.000 claims 1
- 239000010949 copper Substances 0.000 description 37
- 229910052802 copper Inorganic materials 0.000 description 36
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 35
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 28
- 239000011342 resin composition Substances 0.000 description 28
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 14
- 238000001879 gelation Methods 0.000 description 11
- 230000002401 inhibitory effect Effects 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical group 0.000 description 9
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229920001225 polyester resin Polymers 0.000 description 7
- 239000004645 polyester resin Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000001879 copper Chemical class 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 239000000499 gel Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 description 2
- UXCKXHXXSNDUMI-UHFFFAOYSA-L copper;2-carboxy-6-phenylphenolate Chemical compound [Cu+2].OC1=C(C([O-])=O)C=CC=C1C1=CC=CC=C1.OC1=C(C([O-])=O)C=CC=C1C1=CC=CC=C1 UXCKXHXXSNDUMI-UHFFFAOYSA-L 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- MJPVGGOIMUJJEB-UHFFFAOYSA-M methyl(triphenyl)arsanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[As+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 MJPVGGOIMUJJEB-UHFFFAOYSA-M 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- PJCNSVHWHHVSMK-UHFFFAOYSA-N 4-(4-methylanilino)phenol Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C=C1 PJCNSVHWHHVSMK-UHFFFAOYSA-N 0.000 description 1
- HFLGBNBLMBSXEM-UHFFFAOYSA-N 4-Ethyl-1,2-benzenediol Chemical compound CCC1=CC=C(O)C(O)=C1 HFLGBNBLMBSXEM-UHFFFAOYSA-N 0.000 description 1
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 description 1
- NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 description 1
- JXSRRBVHLUJJFC-UHFFFAOYSA-N 7-amino-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound N1=CC(C#N)=C(N)N2N=C(SC)N=C21 JXSRRBVHLUJJFC-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ZCGHEBMEQXMRQL-UHFFFAOYSA-N benzyl 2-carbamoylpyrrolidine-1-carboxylate Chemical compound NC(=O)C1CCCN1C(=O)OCC1=CC=CC=C1 ZCGHEBMEQXMRQL-UHFFFAOYSA-N 0.000 description 1
- YLIFEFSWTZZMTC-UHFFFAOYSA-N benzyl(triphenyl)arsanium Chemical compound C=1C=CC=CC=1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 YLIFEFSWTZZMTC-UHFFFAOYSA-N 0.000 description 1
- BNQRPLGZFADFGA-UHFFFAOYSA-N benzyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 BNQRPLGZFADFGA-UHFFFAOYSA-N 0.000 description 1
- YKOQAAJBYBTSBS-UHFFFAOYSA-N biphenyl-2,3-diol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1O YKOQAAJBYBTSBS-UHFFFAOYSA-N 0.000 description 1
- GINMLXSVBUQABY-UHFFFAOYSA-N carboxymethyl(triphenyl)arsanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[As+](C=1C=CC=CC=1)(CC(=O)O)C1=CC=CC=C1 GINMLXSVBUQABY-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- CMRVDFLZXRTMTH-UHFFFAOYSA-L copper;2-carboxyphenolate Chemical compound [Cu+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O CMRVDFLZXRTMTH-UHFFFAOYSA-L 0.000 description 1
- RIOSFUBRIQHOMS-UHFFFAOYSA-L copper;benzenesulfonate Chemical compound [Cu+2].[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1 RIOSFUBRIQHOMS-UHFFFAOYSA-L 0.000 description 1
- JDPSPYBMORZJOD-UHFFFAOYSA-L copper;dodecanoate Chemical compound [Cu+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O JDPSPYBMORZJOD-UHFFFAOYSA-L 0.000 description 1
- FWBOFUGDKHMVPI-UHFFFAOYSA-K dicopper;2-oxidopropane-1,2,3-tricarboxylate Chemical compound [Cu+2].[Cu+2].[O-]C(=O)CC([O-])(C([O-])=O)CC([O-])=O FWBOFUGDKHMVPI-UHFFFAOYSA-K 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- GHLKOMSNOFJXDT-UHFFFAOYSA-M methyl(triphenyl)arsanium;iodide Chemical compound [I-].C=1C=CC=CC=1[As+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 GHLKOMSNOFJXDT-UHFFFAOYSA-M 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- BDJXVNRFAQSMAA-UHFFFAOYSA-N quinhydrone Chemical compound OC1=CC=C(O)C=C1.O=C1C=CC(=O)C=C1 BDJXVNRFAQSMAA-UHFFFAOYSA-N 0.000 description 1
- 229940052881 quinhydrone Drugs 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- IUVXCVGGLRYGFE-UHFFFAOYSA-N tetraphenyl-lambda5-arsane hydrochloride Chemical compound C1=CC=C(C=C1)[AsH](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.Cl IUVXCVGGLRYGFE-UHFFFAOYSA-N 0.000 description 1
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US834286XA | 1956-05-07 | 1956-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1032919B true DE1032919B (de) | 1958-06-26 |
Family
ID=22178257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU4420A Pending DE1032919B (de) | 1956-05-07 | 1957-03-12 | Verfahren zur Herstellung einer lagerfaehigen, aushaertbaren Polyestermasse |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1032919B (enrdf_load_stackoverflow) |
| FR (1) | FR1172736A (enrdf_load_stackoverflow) |
| GB (1) | GB834286A (enrdf_load_stackoverflow) |
| NL (1) | NL98509C (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1105609B (de) * | 1959-10-29 | 1961-04-27 | Basf Ag | Verfahren zum Verbessern der Lagerfaehigkeit von ungesaettigten polymerisierbaren Polyesterharzmassen |
| DE1174978B (de) * | 1959-10-22 | 1964-07-30 | Allied Chem | Verbessern der Lagerfaehigkeit von Polyester-Formmassen |
| DE1224488B (de) * | 1964-07-23 | 1966-09-08 | Huels Chemische Werke Ag | Stabilisatoren fuer die Lagerstabilitaet von Polyester-Formmassen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2203509B1 (en) | 2007-10-25 | 2015-03-18 | DSM IP Assets B.V. | Unsaturated polyester resin compositions |
| WO2013007602A1 (en) | 2011-07-08 | 2013-01-17 | Dsm Ip Assets B.V. | Multi-component resin system |
| RU2017103145A (ru) * | 2014-07-01 | 2018-08-02 | Ашленд Лайсенсинг Энд Интеллектчуал Проперти Ллк | Не содержащая кобальт предварительно промотированная система на основе ненасыщенной сложной полиэфирной смолы, предназначенная для изготовления искусственного камня |
| CN107108359A (zh) * | 2014-09-12 | 2017-08-29 | 亚什兰许可和知识产权有限公司 | 用于抗静电地板的包含可固化树脂的组合物 |
| EP4087679A2 (en) * | 2020-01-09 | 2022-11-16 | Colorado State University Research Foundation | Benzoperylene imide photoredox catalysts and methods of using such catalysts |
-
0
- NL NL98509D patent/NL98509C/xx active
-
1957
- 1957-01-31 GB GB3419/57A patent/GB834286A/en not_active Expired
- 1957-02-26 FR FR1172736D patent/FR1172736A/fr not_active Expired
- 1957-03-12 DE DEU4420A patent/DE1032919B/de active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1174978B (de) * | 1959-10-22 | 1964-07-30 | Allied Chem | Verbessern der Lagerfaehigkeit von Polyester-Formmassen |
| DE1105609B (de) * | 1959-10-29 | 1961-04-27 | Basf Ag | Verfahren zum Verbessern der Lagerfaehigkeit von ungesaettigten polymerisierbaren Polyesterharzmassen |
| DE1224488B (de) * | 1964-07-23 | 1966-09-08 | Huels Chemische Werke Ag | Stabilisatoren fuer die Lagerstabilitaet von Polyester-Formmassen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL98509C (enrdf_load_stackoverflow) | |
| FR1172736A (fr) | 1959-02-13 |
| GB834286A (en) | 1960-05-04 |
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