DE2328524A1 - Verfahren zur herstellung eines modifizierten kohlenwasserstoffpolymers - Google Patents
Verfahren zur herstellung eines modifizierten kohlenwasserstoffpolymersInfo
- Publication number
- DE2328524A1 DE2328524A1 DE2328524A DE2328524A DE2328524A1 DE 2328524 A1 DE2328524 A1 DE 2328524A1 DE 2328524 A DE2328524 A DE 2328524A DE 2328524 A DE2328524 A DE 2328524A DE 2328524 A1 DE2328524 A1 DE 2328524A1
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- ester
- silyl
- silyl ester
- group
- 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
- 229920000642 polymer Polymers 0.000 title claims description 60
- 238000000034 method Methods 0.000 title claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 13
- 229930195733 hydrocarbon Natural products 0.000 title claims description 13
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 silyl ester Chemical class 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 16
- 150000001993 dienes Chemical class 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- HSVFKFNNMLUVEY-UHFFFAOYSA-N sulfuryl diazide Chemical compound [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-] HSVFKFNNMLUVEY-UHFFFAOYSA-N 0.000 claims description 8
- GZNPNQZOGITHGL-UHFFFAOYSA-N 3-azidosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)N=[N+]=[N-])=C1 GZNPNQZOGITHGL-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 238000004073 vulcanization Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 8
- 229920001195 polyisoprene Polymers 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000012763 reinforcing filler Substances 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- 150000001540 azides Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000006884 silylation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000000463 material Substances 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
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KQPUUBBRXBUZRW-UHFFFAOYSA-N 2-(4-azidosulfonylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1 KQPUUBBRXBUZRW-UHFFFAOYSA-N 0.000 description 1
- RFKWPZSWBXUOCY-UHFFFAOYSA-N 2-azidosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)N=[N+]=[N-] RFKWPZSWBXUOCY-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical class CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- WQBQDHDUGLLGHT-UHFFFAOYSA-N 4-chloro-n-diazobenzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1 WQBQDHDUGLLGHT-UHFFFAOYSA-N 0.000 description 1
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 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
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- XRLLPTOZRSBHHS-UHFFFAOYSA-N carboxysulfonyl(diazonio)azanide Chemical compound OC(=O)S(=O)(=O)[N-][N+]#N XRLLPTOZRSBHHS-UHFFFAOYSA-N 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- ITKVLPYNJQOCPW-UHFFFAOYSA-N chloro-(chloromethyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCl ITKVLPYNJQOCPW-UHFFFAOYSA-N 0.000 description 1
- SXSNZRHGAMVNJE-UHFFFAOYSA-N chloro-[[[chloromethyl(dimethyl)silyl]amino]-dimethylsilyl]methane Chemical compound ClC[Si](C)(C)N[Si](C)(C)CCl SXSNZRHGAMVNJE-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- UQOLEKZLCRBTMR-UHFFFAOYSA-N n-diazopyridine-3-sulfonamide Chemical compound [N-]=[N+]=NS(=O)(=O)C1=CC=CN=C1 UQOLEKZLCRBTMR-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/22—Incorporating nitrogen atoms into the molecule
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7207689A NL7207689A (cg-RX-API-DMAC7.html) | 1972-06-07 | 1972-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2328524A1 true DE2328524A1 (de) | 1974-01-03 |
Family
ID=19816221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2328524A Pending DE2328524A1 (de) | 1972-06-07 | 1973-06-05 | Verfahren zur herstellung eines modifizierten kohlenwasserstoffpolymers |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4962587A (cg-RX-API-DMAC7.html) |
| BE (1) | BE800161A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1024296A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2328524A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES415554A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2198955B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1435127A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1006586B (cg-RX-API-DMAC7.html) |
| NL (1) | NL7207689A (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA733792B (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940427A (en) * | 1974-06-26 | 1976-02-24 | Union Carbide Corporation | Azidosulfonyl compounds |
| US4551504A (en) * | 1984-01-18 | 1985-11-05 | Union Carbide Corporation | Water curable, azide sulfonyl silane modified ethylene polymers |
| US4514545A (en) * | 1984-01-18 | 1985-04-30 | Union Carbide Corporation | Water curable, azide sulfonyl silane modified, alkylene-alkyl acrylate copolymers |
| RU2213101C2 (ru) * | 1997-08-27 | 2003-09-27 | Дау Глобал Текнолоджиз Инк. | Связывание винилароматических полимеров и пены |
| EP1007589B1 (en) | 1997-08-27 | 2003-10-01 | The Dow Chemical Company | Coupling of blends of alpha-olefin/vinyl aromatic monomer or hindered aliphatic vinyl monomer interpolymers with polyolefins |
| US6325956B2 (en) | 1997-08-27 | 2001-12-04 | The Dow Chemical Company | Crosslinking of polymers and foams thereof |
| EP1007586B1 (en) | 1997-08-27 | 2005-10-12 | Dow Global Technologies Inc. | Rheology modification of low density polyethylene |
| US6277916B1 (en) | 1999-02-25 | 2001-08-21 | The Dow Chemical Company | Process for preparing thermoplastic vulcanizates |
| ATE286939T1 (de) | 1999-06-24 | 2005-01-15 | Dow Chemical Co | Polyolefinzusammensetzung mit verbesserten schlagzäheigenschaften |
| US6331597B1 (en) * | 1999-08-09 | 2001-12-18 | The Dow Chemical Company | Azidosilane-modified, moisture-curable polyolefin polymers, process for making, and articles obtained therefrom |
| EP1276611B1 (en) | 2000-01-24 | 2004-04-21 | Dow Global Technologies Inc. | Composition and films thereof |
| KR100740729B1 (ko) | 2000-05-04 | 2007-07-19 | 다우 글로벌 테크놀로지스 인크. | 분자 용융물 및 그 분자 용융물의 제조 방법 및 사용 방법 |
| WO2001092403A2 (en) | 2000-05-26 | 2001-12-06 | Dow Global Technologies Inc. | Polyethylene rich/polypropylene blends and their uses |
| US6800669B2 (en) | 2000-12-22 | 2004-10-05 | Dow Global Technologies Inc. | Propylene copolymer foams |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3220985A (en) * | 1962-10-15 | 1965-11-30 | Hercules Powder Co Ltd | Modifying hydrocarbon polymers |
-
1972
- 1972-06-07 NL NL7207689A patent/NL7207689A/xx unknown
-
1973
- 1973-05-01 CA CA170,193A patent/CA1024296A/en not_active Expired
- 1973-05-29 BE BE1005101A patent/BE800161A/xx unknown
- 1973-06-04 IT IT25026/73A patent/IT1006586B/it active
- 1973-06-05 DE DE2328524A patent/DE2328524A1/de active Pending
- 1973-06-05 FR FR7320354A patent/FR2198955B1/fr not_active Expired
- 1973-06-05 ES ES415554A patent/ES415554A1/es not_active Expired
- 1973-06-05 GB GB2673573A patent/GB1435127A/en not_active Expired
- 1973-06-05 JP JP48062650A patent/JPS4962587A/ja active Pending
- 1973-06-05 ZA ZA733792A patent/ZA733792B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU5654673A (en) | 1974-12-05 |
| ES415554A1 (es) | 1976-02-16 |
| BE800161A (nl) | 1973-11-29 |
| FR2198955B1 (cg-RX-API-DMAC7.html) | 1977-05-06 |
| IT1006586B (it) | 1976-10-20 |
| JPS4962587A (cg-RX-API-DMAC7.html) | 1974-06-18 |
| ZA733792B (en) | 1974-04-24 |
| GB1435127A (en) | 1976-05-12 |
| NL7207689A (cg-RX-API-DMAC7.html) | 1973-12-11 |
| FR2198955A1 (cg-RX-API-DMAC7.html) | 1974-04-05 |
| CA1024296A (en) | 1978-01-10 |
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