CN111961197B - 一种氨基酸改性硅烷封端聚醚及其制备方法 - Google Patents
一种氨基酸改性硅烷封端聚醚及其制备方法 Download PDFInfo
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- CN111961197B CN111961197B CN202010861804.6A CN202010861804A CN111961197B CN 111961197 B CN111961197 B CN 111961197B CN 202010861804 A CN202010861804 A CN 202010861804A CN 111961197 B CN111961197 B CN 111961197B
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- Prior art keywords
- amino acid
- polyether
- nucleophilic addition
- addition reaction
- terminated
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- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 114
- 229920000570 polyether Polymers 0.000 title claims abstract description 114
- -1 Amino acid modified silane Chemical class 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001413 amino acids Chemical class 0.000 claims abstract description 54
- 229920005862 polyol Polymers 0.000 claims abstract description 44
- 150000003077 polyols Chemical class 0.000 claims abstract description 44
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 22
- NOKSMMGULAYSTD-UHFFFAOYSA-N [SiH4].N=C=O Chemical compound [SiH4].N=C=O NOKSMMGULAYSTD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 238000005935 nucleophilic addition reaction Methods 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000000047 product Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 12
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 10
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 8
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
- 229960003104 ornithine Drugs 0.000 claims description 8
- MJHLGXKXOPOSNH-GFCCVEGCSA-N (2r)-6-[bis(ethylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound CCNC(NCC)=NCCCC[C@H](C(O)=O)NC(=O)OC(C)(C)C MJHLGXKXOPOSNH-GFCCVEGCSA-N 0.000 claims description 7
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 3
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- 239000012970 tertiary amine catalyst Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 238000012661 block copolymerization Methods 0.000 abstract description 3
- 239000003707 silyl modified polymer Substances 0.000 abstract description 3
- 239000002861 polymer material Substances 0.000 abstract description 2
- 229940024606 amino acid Drugs 0.000 description 53
- 238000003756 stirring Methods 0.000 description 20
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 16
- 239000012975 dibutyltin dilaurate Substances 0.000 description 16
- 239000000565 sealant Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 238000001291 vacuum drying Methods 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005034 decoration Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VKSCZTWQDPUHIK-UHFFFAOYSA-N isocyanic acid;trimethoxy(propyl)silane Chemical compound N=C=O.CCC[Si](OC)(OC)OC VKSCZTWQDPUHIK-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000004588 polyurethane sealant Substances 0.000 description 3
- 239000012812 sealant material Substances 0.000 description 3
- 239000004526 silane-modified polyether Substances 0.000 description 3
- 239000004590 silicone sealant Substances 0.000 description 3
- UAYLDTQWSNYJDA-MPUYUTEFSA-N (3S)-3-amino-4-[4-[[4-[(2S)-2-amino-3-carboxypropanoyl]oxycyclohexyl]methyl]cyclohexyl]oxy-4-oxobutanoic acid Chemical compound N[C@@H](CC(O)=O)C(OC1CCC(CC(CC2)CCC2OC([C@H](CC(O)=O)N)=O)CC1)=O UAYLDTQWSNYJDA-MPUYUTEFSA-N 0.000 description 2
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
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CN202010861804.6A CN111961197B (zh) | 2020-08-25 | 2020-08-25 | 一种氨基酸改性硅烷封端聚醚及其制备方法 |
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CN202010861804.6A CN111961197B (zh) | 2020-08-25 | 2020-08-25 | 一种氨基酸改性硅烷封端聚醚及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN111961197A CN111961197A (zh) | 2020-11-20 |
CN111961197B true CN111961197B (zh) | 2021-05-14 |
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CN202010861804.6A Active CN111961197B (zh) | 2020-08-25 | 2020-08-25 | 一种氨基酸改性硅烷封端聚醚及其制备方法 |
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6046295A (en) * | 1993-08-20 | 2000-04-04 | 3M Innovative Properties Company | Room temperature curable silane-terminated polyurethane dispersions |
US6626988B1 (en) * | 1999-05-21 | 2003-09-30 | Bayer Aktiengesellschaft | Phosphate-stabilized polyurethane materials, cross-linked by condensation, method for their production and use thereof |
CN1871270A (zh) * | 2003-10-22 | 2006-11-29 | 拜尔材料科学有限公司 | 可湿固化的具有活性硅烷基的聚醚氨酯及其作为密封剂、粘合剂和涂料的应用 |
CN104277227A (zh) * | 2013-07-01 | 2015-01-14 | 赢创工业集团股份有限公司 | 具有含有包含脲基和/或氨基甲酸酯基和氨基酸基团的末端有机官能团的硅氧烷聚合物 |
CN104387547A (zh) * | 2014-11-19 | 2015-03-04 | 上海华峰新材料研发科技有限公司 | 水性聚氨酯树脂及其制备方法和应用 |
CN107001556A (zh) * | 2014-11-24 | 2017-08-01 | Sika技术股份公司 | 含有硅烷基团的快速固化组合物 |
CN107001568A (zh) * | 2014-11-24 | 2017-08-01 | Sika技术股份公司 | 含硅烷基团的快速固化组合物 |
CN111479846A (zh) * | 2017-12-19 | 2020-07-31 | 科思创德国股份有限公司 | 制备聚醚酯多元醇的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110301639A1 (en) * | 2010-05-28 | 2011-12-08 | Beckman Eric J | One-Part Moisture-Curable Tissue Sealant |
-
2020
- 2020-08-25 CN CN202010861804.6A patent/CN111961197B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6046295A (en) * | 1993-08-20 | 2000-04-04 | 3M Innovative Properties Company | Room temperature curable silane-terminated polyurethane dispersions |
US6626988B1 (en) * | 1999-05-21 | 2003-09-30 | Bayer Aktiengesellschaft | Phosphate-stabilized polyurethane materials, cross-linked by condensation, method for their production and use thereof |
CN1871270A (zh) * | 2003-10-22 | 2006-11-29 | 拜尔材料科学有限公司 | 可湿固化的具有活性硅烷基的聚醚氨酯及其作为密封剂、粘合剂和涂料的应用 |
CN104277227A (zh) * | 2013-07-01 | 2015-01-14 | 赢创工业集团股份有限公司 | 具有含有包含脲基和/或氨基甲酸酯基和氨基酸基团的末端有机官能团的硅氧烷聚合物 |
CN104387547A (zh) * | 2014-11-19 | 2015-03-04 | 上海华峰新材料研发科技有限公司 | 水性聚氨酯树脂及其制备方法和应用 |
CN107001556A (zh) * | 2014-11-24 | 2017-08-01 | Sika技术股份公司 | 含有硅烷基团的快速固化组合物 |
CN107001568A (zh) * | 2014-11-24 | 2017-08-01 | Sika技术股份公司 | 含硅烷基团的快速固化组合物 |
CN111479846A (zh) * | 2017-12-19 | 2020-07-31 | 科思创德国股份有限公司 | 制备聚醚酯多元醇的方法 |
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Effective date of registration: 20231221 Address after: Room 710, No. 2, Lane 58, Xinjian East Road, Minhang District, Shanghai, 201199 Patentee after: Yuxuan Investment (Hainan) Co.,Ltd. Address before: Room 1122, building 3, No. 215, Lianhe North Road, Fengxian District, Shanghai 201400 Patentee before: Shanghai Xinda Chemical Co.,Ltd. |