USRE39559E1 - Butadiene polymers having terminal functional groups - Google Patents
Butadiene polymers having terminal functional groups Download PDFInfo
- Publication number
- USRE39559E1 USRE39559E1 US10/657,064 US65706403A USRE39559E US RE39559 E1 USRE39559 E1 US RE39559E1 US 65706403 A US65706403 A US 65706403A US RE39559 E USRE39559 E US RE39559E
- Authority
- US
- United States
- Prior art keywords
- polymer
- molecular weight
- peak molecular
- hydrogenated butadiene
- polymers
- 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.)
- Expired - Lifetime
Links
- 125000000524 functional group Chemical group 0.000 title claims abstract description 24
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 title abstract description 71
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 168
- 229920000642 polymer Polymers 0.000 claims abstract description 88
- 238000011925 1,2-addition Methods 0.000 claims abstract description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 5
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- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 229920001400 block copolymer Polymers 0.000 abstract description 25
- 238000000576 coating method Methods 0.000 abstract description 15
- 239000000565 sealant Substances 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 239000011230 binding agent Substances 0.000 abstract description 2
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- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 11
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- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 3
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- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 3
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- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
-
- X—B—Li
- X—A—B—Li
- X—A—B—A—Li
- Li—B—Y—B—Li
- Li—A—B—Y—B—A—Li
wherein B represents polymerized units of one or more conjugated diene hydrocarbons such as butadiene or isoprene, A represents polymerized units of one or more vinyl aromatic compounds such as styrene, X is the residue of a monolithium initiator such as sec-butyllithium, and Y is the residue of a dilithium initiator such as the diadduct of sec-butyllithium and m-diisopropenylbenzene. Some structures, including those pertaining to polylithium initiators or random units of styrene and a conjugated diene, generally have limited practical utility although known in the art.
TABLE 1 | |||||
| MW | 1,2-Addition | EO Capping | Hydrogen- | |
Number | (Peak) | (%) | Efficiency (%) | ation (%) | |
1 | 2900 | 40 | 82 | 95 | |
2 | 3900 | 41 | 95 | 98 | |
3 | 5060 | 40 | 92 | 99 | |
4 | 3500 | 52 | 87 | 98 | |
5 | 3970 | 48 | 85 | 99 | |
POLY- | 2300 | 84 | NA | 993 | |
TAIL HA1 | |||||
NISSO | 2380 | 84 | NA | 983 | |
GI-20002 | |||||
POLY- | 3720 | 22 | NA | NA | |
TAIL H1 | |||||
1Polymer produced by Mitsubishi. | |||||
2Polymer produced by Nippon Soda. | |||||
3Measured by ozonolysis. |
TABLE 2 | |||||
| MW | 1,2-Addition | Viscosity | Adj. Viscosity | |
Number | (Peak) | (%) | (poise) | (poise/MW3,4) | |
1 | 2900 | 40 | 195 | 0.26 × 10−9 |
2 | 3900 | 41 | 836 | 0.52 × 10−9 |
3 | 5060 | 40 | 2322 | 0.59 × 10−9 |
4 | 3500 | 52 | 353 | 0.32 × 10−9 |
5 | 3970 | 48 | 760 | 0.44 × 10−9 |
POLYTAIL | 2300 | 84 | 1650 | 6.1 × 10−9 |
HA1 | ||||
NISSO | 2380 | 84 | 1480 | 4.9 × 10−9 |
GI-20002 | ||||
POLYTAIL | 3720 | 22 | Solid3 | — |
H1 | ||||
1Polymer produced by Mitsubishi. | ||||
2Polymer produced by Nippon Soda. | ||||
3Infinite visocity at room temperature. |
Claims (27)
Priority Applications (1)
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US10/657,064 USRE39559E1 (en) | 1992-08-31 | 2003-09-05 | Butadiene polymers having terminal functional groups |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/938,917 US5393843A (en) | 1992-08-31 | 1992-08-31 | Butadiene polymers having terminal functional groups |
US10/657,064 USRE39559E1 (en) | 1992-08-31 | 2003-09-05 | Butadiene polymers having terminal functional groups |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US07/938,917 Reissue US5393843A (en) | 1992-08-31 | 1992-08-31 | Butadiene polymers having terminal functional groups |
Publications (1)
Publication Number | Publication Date |
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USRE39559E1 true USRE39559E1 (en) | 2007-04-10 |
Family
ID=25472204
Family Applications (4)
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US07/938,917 Ceased US5393843A (en) | 1992-08-31 | 1992-08-31 | Butadiene polymers having terminal functional groups |
US08/306,552 Ceased US5405911A (en) | 1992-08-31 | 1994-09-15 | Butadiene polymers having terminal functional groups |
US10/655,988 Expired - Lifetime USRE39617E1 (en) | 1992-08-31 | 2003-09-05 | Butadiene polymers having terminal functional groups |
US10/657,064 Expired - Lifetime USRE39559E1 (en) | 1992-08-31 | 2003-09-05 | Butadiene polymers having terminal functional groups |
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US07/938,917 Ceased US5393843A (en) | 1992-08-31 | 1992-08-31 | Butadiene polymers having terminal functional groups |
US08/306,552 Ceased US5405911A (en) | 1992-08-31 | 1994-09-15 | Butadiene polymers having terminal functional groups |
US10/655,988 Expired - Lifetime USRE39617E1 (en) | 1992-08-31 | 2003-09-05 | Butadiene polymers having terminal functional groups |
Country Status (2)
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US (4) | US5393843A (en) |
GB (1) | GB2270317A (en) |
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Also Published As
Publication number | Publication date |
---|---|
USRE39617E1 (en) | 2007-05-08 |
US5393843A (en) | 1995-02-28 |
GB2270317A (en) | 1994-03-09 |
GB9317935D0 (en) | 1993-10-13 |
US5405911A (en) | 1995-04-11 |
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