WO1995002004B1 - Halogen-free radiation curable flame retardant compositions - Google Patents
Halogen-free radiation curable flame retardant compositionsInfo
- Publication number
- WO1995002004B1 WO1995002004B1 PCT/NL1994/000155 NL9400155W WO9502004B1 WO 1995002004 B1 WO1995002004 B1 WO 1995002004B1 NL 9400155 W NL9400155 W NL 9400155W WO 9502004 B1 WO9502004 B1 WO 9502004B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- diisocyanate
- group
- oligomer
- polyol
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 19
- 239000003063 flame retardant Substances 0.000 title claims abstract 5
- 229920005862 polyol Polymers 0.000 claims abstract 7
- 229920001228 Polyisocyanate Polymers 0.000 claims abstract 6
- 239000000178 monomer Substances 0.000 claims abstract 6
- 239000005056 polyisocyanate Substances 0.000 claims abstract 6
- -1 phosphonate polyol Chemical class 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims 5
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims 4
- 239000007795 chemical reaction product Substances 0.000 claims 4
- 229920000642 polymer Polymers 0.000 claims 3
- 150000003077 polyols Chemical class 0.000 claims 3
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 claims 2
- MTPIZGPBYCHTGQ-UHFFFAOYSA-N 2-[2,2-bis(2-prop-2-enoyloxyethoxymethyl)butoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCC(CC)(COCCOC(=O)C=C)COCCOC(=O)C=C MTPIZGPBYCHTGQ-UHFFFAOYSA-N 0.000 claims 2
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 claims 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N Hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N Isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N Toluene diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 2
- UQFAQHDNJXQUAS-UHFFFAOYSA-N [N-]=C=O.[N-]=C=O.C1=CC=CC=C1C1=CC=CC=C1 Chemical compound [N-]=C=O.[N-]=C=O.C1=CC=CC=C1C1=CC=CC=C1 UQFAQHDNJXQUAS-UHFFFAOYSA-N 0.000 claims 2
- YPSDSVRZCYLHBF-UHFFFAOYSA-N [N-]=C=O.[N-]=C=O.CCCCCC(C)(C)C Chemical compound [N-]=C=O.[N-]=C=O.CCCCCC(C)(C)C YPSDSVRZCYLHBF-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- QIMNMSOZIDDLGN-UHFFFAOYSA-L cyclohexylmethylcyclohexane;dicyanate Chemical compound [O-]C#N.[O-]C#N.C1CCCCC1CC1CCCCC1 QIMNMSOZIDDLGN-UHFFFAOYSA-L 0.000 claims 2
- 239000003365 glass fiber Substances 0.000 claims 2
- 239000011159 matrix material Substances 0.000 claims 2
- YNXCGLKMOXLBOD-UHFFFAOYSA-N oxolan-2-ylmethyl prop-2-enoate Chemical group C=CC(=O)OCC1CCCO1 YNXCGLKMOXLBOD-UHFFFAOYSA-N 0.000 claims 2
- 239000000758 substrate Substances 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims 1
- DQJSFBCVEPQRLA-UHFFFAOYSA-N 1-methoxyethyl prop-2-enoate Chemical compound COC(C)OC(=O)C=C DQJSFBCVEPQRLA-UHFFFAOYSA-N 0.000 claims 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims 1
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- VONWDASPFIQPDY-UHFFFAOYSA-N Dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 238000010894 electron beam technology Methods 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims 1
Abstract
A halogen-free radiation curable flame retardant composition that comprises an end-capped oligomer of a phosphonate polyol and a polyisocyanate and an organic monomer.
Claims
1. An essentially halogen-free UV-radiation or electron-beam curable composition suitable for producing a flame retardant polymer , which compr ises :
an oligomer that is the react ion product of a
polyisocyanate and a phosphonate polyol , said oligomer being end-capped by at least one monohydroxyfunctional compound with ethylenic unsaturat ion; and an organic monomer ; said polyol having the formula ;
wherein R1 and R3 are independently C1 to C10 alkyl or aryl; and R2 is polyhydroxyalkyl, polyhydroxyaryl, polyhydroxyalkylarainoalkyl, polyhydroxyarylamino-alkyl, polyhydroxyalkylaminoaryl or polyhydroxyaryl-aminoaryl having from 1 to 18 carbon atoms inclusive.
2. The composition of claim 1 wherein said polyisocyanate is selected from the group consisting of toluene
diisocyanate, trimethylhexane diisocyanate,
dicyclohexylmethane diisocyanate, isophoronediisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, phenylene diisocyanate, and biphenyl diisocyanate.
3. The composition of claim 1 wherein R1 and R3 are ethyl.
4. The composition of claim 1 wherein R2 is N,N-bis(2- hydroxyethyl) aminomsthyl.
5. The composition of claim 1 wherein said organic monomer is selected from the group consisting of
tetrahydrofurfuryl acrylate, ethoxyethoxyethyl acrylate, diethyleneglycol diacrylate, trimethylolpropane
ethoxylate triacrylate, methoxyethyl acrylate and hydroxy caprolactone acrylate.
6. The composition of claim 1 wherein said monohydroxy
compound with ethylenic unsaturation is 2-hydroxyethyl acrylate.
7, A radiation curable composition suitable for producing a flame retardant polymer, which comprises:
an oligomer that is the reaction product of a
polyisocyanate and a phosphonate polyol, said oligomer being capped by at least one monohydroxy functional compound with ethylenic unsaturation; and an organic monomer; said polyol being the reaction product of dimethyl methylphosphonate, phosphorus pentoxide, ethylene oxide and water in a molar ratio of about
2:2:8:1, respectively.
8. A radiation curable composition suitable for producing a flame retardant polymer, which comprises:
an oligomer that is the reaction product of a
polyisocyanate and a phosphonate polyol, said oligomer being capped by at least one monohydroxy functional compound with ethylenic unsaturation; and an organic monomer; said polyol having the formula:
polyhydroκyalkylaminoalkyl, polyhydroxyarylaminoalkyl, polyhydroxyalkylaminoaryl and polyhydroxyarylaminoaryl; R3 and Ra are each independently selected from the group consisting of alkylene and arylene; m and n are each independently an integer from 0 to 10 inclusive, provided that at least one of m and n is 1 or more; and x is 1 to 100.
9. The composition of claim 8 wherein said monohydroxy
compound with ethylenic unsaturation is 2- hydroxyethylacrylate.
10. The composition of claim 8 wherein R3 and R5 are ethylene.
11. The composition of claim 8 wherein R4 is methyl.
12. The composition of claim 8 wherein said polyisocyanate is selected from the group consisting of toluene
diisocyanate, trimethylhexanediisocyanate, dicyclohexyl methane diisocyanate, isophorone diisocyanate,
diphenylmethane diisocyanate, hexamethylene diisocyanate, phenylene diisocyanate and biphenyl diisocyanate.
13. The composition of claim 8 wherein said organic monomer is selected from the group consisting of diethyleneglycol diacrylate, tripropyleneglycoldiacrylate, hexanediol diacrylate, tetrahydrofurfurylacrylate and
trimethylolpropane ethoxylate triacrylate.
14. A substrate that is coated with the composition of claim 1, which is cured.
15. A substrate that is coated with the cured composition of claim 8, which is cured.
16. A group of optical fibers having a matrix made from the cured composition of claim 1.
17. A group of optical fibers having a matrix made from the cured composition of claim 8.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50397395A JP3512804B2 (en) | 1993-07-08 | 1994-07-05 | Halogen-free radiation-curable flame-retardant compositions |
| AU74683/94A AU687085B2 (en) | 1993-07-08 | 1994-07-05 | Halogen-free radiation curable flame retardant compositions |
| EP94924415A EP0707606B1 (en) | 1993-07-08 | 1994-07-05 | Halogen-free radiation curable flame retardant compositions |
| DE69413821T DE69413821T2 (en) | 1993-07-08 | 1994-07-05 | HALOGEN-FREE, RADIATION-curable, flame-retardant compositions |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8917393A | 1993-07-08 | 1993-07-08 | |
| US21226594A | 1994-03-14 | 1994-03-14 | |
| US08/089,173 | 1994-03-14 | ||
| US08/212,265 | 1994-03-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1995002004A1 WO1995002004A1 (en) | 1995-01-19 |
| WO1995002004B1 true WO1995002004B1 (en) | 1995-02-23 |
Family
ID=26780320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/NL1994/000155 WO1995002004A1 (en) | 1993-07-08 | 1994-07-05 | Halogen-free radiation curable flame retardant compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5456984A (en) |
| EP (1) | EP0707606B1 (en) |
| JP (1) | JP3512804B2 (en) |
| AU (1) | AU687085B2 (en) |
| CA (1) | CA2166716A1 (en) |
| DE (1) | DE69413821T2 (en) |
| WO (1) | WO1995002004A1 (en) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4003838B2 (en) | 1997-03-18 | 2007-11-07 | ディーエスエム アイピー アセッツ ビー． ブイ | Optical fiber coating and ink curing by low power electron beam irradiation |
| FR2767724B1 (en) | 1997-09-01 | 2001-06-01 | France Telecom | METHOD AND DEVICE FOR COATING A WIRED ELEMENT WITH A THIN LAYER OF LIQUID AND OPTICAL FIBER AGENT THUS COATED |
| US5977202A (en) * | 1997-09-22 | 1999-11-02 | Dsm N.V. | Radiation-curable compositions having fast cure speed and good adhesion to glass |
| EP1031574A1 (en) * | 1999-02-26 | 2000-08-30 | Ucb S.A. | Phosphorylated polyol, oligomer therefrom, polymer therefrom, processes for preparing them and their uses |
| DE19927548C2 (en) * | 1999-06-16 | 2002-12-12 | Clariant Gmbh | Process for the production of flame-retardant flexible polyurethane foams |
| EP1101785A1 (en) * | 1999-11-15 | 2001-05-23 | Alcatel | Hollow or bundle charger |
| KR100730872B1 (en) | 1999-12-30 | 2007-06-20 | 코닝 인코포레이티드 | Optical fibers prepared with a primary coating composition including a monomer with a pendant hydroxyl functional group |
| EP1272497A1 (en) * | 2000-04-03 | 2003-01-08 | Ucb, S.A. | Phosphorus containing materials, their preparation and use |
| US20040253594A1 (en) | 2001-05-31 | 2004-12-16 | Tuggle Christopher K | Genetic markers for improved disease resistance in animals (nramp1) |
| US7155100B2 (en) | 2001-11-08 | 2006-12-26 | Dsm Ip Assets B.V. | Flame-retardant optical fiber coating composition |
| JP2003212954A (en) * | 2002-01-21 | 2003-07-30 | Showa Denko Kk | Phosphorus-containing urethane (meth)acrylate compound and photosensitive composition |
| MXPA04012833A (en) | 2002-07-01 | 2005-07-14 | Surface Specialties Sa | Water-thinnable polymer precursors, their preparation and use. |
| EP1556210A1 (en) * | 2002-10-18 | 2005-07-27 | Surface Specialties, S.A. | Flame retardant translucent laminate and method of producing such a laminate |
| US7232850B2 (en) * | 2003-10-03 | 2007-06-19 | Huntsman Advanced Materials Americas Inc. | Photocurable compositions for articles having stable tensile properties |
| US7221841B2 (en) | 2003-10-17 | 2007-05-22 | Dsm Ip Assets B.V. | Flame retardant UV cured buffered optical fibers and buffer composition |
| KR20080113741A (en) * | 2007-06-25 | 2008-12-31 | 김도균 | Polyol included phosphorus and nitrogen |
| KR101023230B1 (en) | 2008-10-06 | 2011-03-21 | 주식회사 대원포리머 | Synthesis and application of flame retardant as UV fixing agent |
| TW201022335A (en) * | 2008-10-21 | 2010-06-16 | Albemarle Corp | Mixed glycol polyphosphonate compounds |
| KR20120052946A (en) * | 2009-07-30 | 2012-05-24 | 아사히 가라스 가부시키가이샤 | Unsaturated urethane oligomer, curable resin composition, transparent laminate, and process for producing same |
| CN102482396A (en) * | 2009-08-14 | 2012-05-30 | 旭硝子株式会社 | Curable resin composition, transparent laminate, and method for producing same |
| US8871843B2 (en) * | 2009-12-15 | 2014-10-28 | Apple Inc. | Halogen-free flame retardant material |
| DK2513002T3 (en) | 2009-12-17 | 2016-04-04 | Dsm Ip Assets Bv | LED CURE OF RADIATABLE OPTICAL FIBER COATING COMPOSITIONS |
| KR101237855B1 (en) | 2010-01-05 | 2013-02-28 | 두루케미칼(주) | Phosphor-based incombustible material and method of preparing the same |
| JP6319793B2 (en) * | 2014-03-31 | 2018-05-09 | ジャパンコーティングレジン株式会社 | Composite resin composition and method for producing the same |
| DK3078723T3 (en) * | 2015-04-09 | 2019-02-25 | Evonik Degussa Gmbh | ADDUCTORS OF ISOCYANATOALKYL TRIMETHOXYSILANES AND WITH THEIR REACTIVE FLAMMIT PROTECTORS |
| US10222547B2 (en) | 2015-11-30 | 2019-03-05 | Corning Incorporated | Flame-retardant optical fiber coating |
| US10167396B2 (en) | 2017-05-03 | 2019-01-01 | Corning Incorporated | Low smoke fire-resistant optical ribbon |
| CN110483578B (en) * | 2019-08-29 | 2020-09-22 | 北京理工大学 | Reactive phosphorus-nitrogen flame retardant and preparation method thereof |
| CN112851925B (en) * | 2021-02-02 | 2023-01-31 | 扬州晨化新材料股份有限公司 | Preparation method of mixed phosphorus-containing polyol flame retardant |
| CN117820599B (en) * | 2024-03-04 | 2024-05-07 | 江苏一特新材料有限责任公司 | Preparation method of ultraviolet light curing softening and cracking preventing agent, positive electrode slurry and preparation method thereof, and preparation method of positive electrode plate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US364910A (en) * | 1887-06-14 | Hand-guide and brake for sleds | ||
| US3953393A (en) * | 1974-01-07 | 1976-04-27 | Basf Wyandotte Corporation | Low temperature process for the preparation of graft copolymer dispersions |
| US4269727A (en) * | 1978-11-13 | 1981-05-26 | The Dow Chemical Company | Radiation curable flame retardant compositions containing 2,2-dialkylpropane-1,3-diolbis[bis-(acryloyloxylkyl) phosphates] |
| JPS59149917A (en) * | 1983-02-16 | 1984-08-28 | Hitachi Chem Co Ltd | Flame-retarding photopolymer composition |
| US4591522A (en) * | 1985-01-04 | 1986-05-27 | W. R. Grace & Co. | Liquid photopolymers curable to fire-retardant, hydrolysis resistant compositions |
| US4883892A (en) * | 1985-05-23 | 1989-11-28 | Akzo America Inc. | Phosphate and phosphonate compounds |
| US4886895A (en) * | 1985-05-23 | 1989-12-12 | Akzo America Inc. | Phosphate-containing and phosphonate-containing phosphate esters |
| US5136679A (en) * | 1985-07-23 | 1992-08-04 | U.S. Philips Corp. | Optical glass fibre having a synthetic resin coating and curable elastomer forming material |
| US4657968A (en) * | 1986-05-14 | 1987-04-14 | Ashland Oil, Inc. | Thermosetting resinous molding compositions for preparing polyurethane containing a phosphorous polyol and an esterol |
| JPH04248506A (en) * | 1991-02-04 | 1992-09-04 | Mitsubishi Rayon Co Ltd | Optical fiber cord |
| US5175228A (en) * | 1991-12-09 | 1992-12-29 | Gencorp Inc. | Two-component primerless urethane-isocyanurate adhesive compositions having high temperature resistance |
-
1994
- 1994-07-05 JP JP50397395A patent/JP3512804B2/en not_active Expired - Fee Related
- 1994-07-05 DE DE69413821T patent/DE69413821T2/en not_active Expired - Fee Related
- 1994-07-05 CA CA 2166716 patent/CA2166716A1/en not_active Abandoned
- 1994-07-05 EP EP94924415A patent/EP0707606B1/en not_active Expired - Lifetime
- 1994-07-05 AU AU74683/94A patent/AU687085B2/en not_active Ceased
- 1994-07-05 WO PCT/NL1994/000155 patent/WO1995002004A1/en active IP Right Grant
-
1995
- 1995-02-06 US US08/381,281 patent/US5456984A/en not_active Expired - Lifetime
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