CA1256243A - Compose adhesif polymerisable par rayonnement - Google Patents

Compose adhesif polymerisable par rayonnement

Info

Publication number: CA1256243A
Authority: CA; Canada
Prior art keywords: composition; component; weight; monoester; polyol
Prior art date: 1983-11-02
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

Application number

CA000440212A

Other languages

English (en)

Inventor

Pierre Chevreux

Christiane A.R. Chevreux

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Deltaglass SA

Original Assignee

Deltaglass SA

Priority date (The priority date 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 date listed.)

1983-11-02

Filing date

1983-11-02

Publication date

1989-06-20

1983-11-02 Application filed by Deltaglass SA filed Critical Deltaglass SA

1983-11-02 Priority to CA000440212A priority Critical patent/CA1256243A/fr

1989-06-20 Application granted granted Critical

1989-06-20 Publication of CA1256243A publication Critical patent/CA1256243A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 132
239000000853 adhesive Substances 0.000 title claims abstract description 40
230000001070 adhesive effect Effects 0.000 title claims abstract description 40
230000005855 radiation Effects 0.000 title description 7
239000000463 material Substances 0.000 claims abstract description 63
UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 58
239000011521 glass Substances 0.000 claims abstract description 45
239000003085 diluting agent Substances 0.000 claims abstract description 32
239000005340 laminated glass Substances 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 10
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 52
150000003077 polyols Chemical class 0.000 claims description 49
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 48
229920005862 polyol Polymers 0.000 claims description 47
239000005056 polyisocyanate Substances 0.000 claims description 41
229920001228 polyisocyanate Polymers 0.000 claims description 32
238000000034 method Methods 0.000 claims description 31
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 25
125000004429 atom Chemical group 0.000 claims description 14
229920005989 resin Polymers 0.000 claims description 13
239000011347 resin Substances 0.000 claims description 13
239000010410 layer Substances 0.000 claims description 12
-1 polymethylene diisocyanates Polymers 0.000 claims description 12
239000004721 Polyphenylene oxide Substances 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
229920003023 plastic Polymers 0.000 claims description 11
229920000570 polyether Polymers 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
239000011888 foil Substances 0.000 claims description 10
239000004033 plastic Substances 0.000 claims description 10
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 9
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000002596 lactones Chemical class 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
239000012790 adhesive layer Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
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 description 5
229920005906 polyester polyol Polymers 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000003822 epoxy resin Substances 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
229920000647 polyepoxide Polymers 0.000 claims description 4
QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical class O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
125000000962 organic group Chemical group 0.000 claims description 3
239000012260 resinous material Substances 0.000 claims description 3
150000002924 oxiranes Chemical class 0.000 claims description 2
239000003999 initiator Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 18
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
239000011229 interlayer Substances 0.000 description 10
239000002253 acid Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 6
230000006872 improvement Effects 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
230000007423 decrease Effects 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000000178 monomer Substances 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
239000012965 benzophenone Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000012634 fragment Substances 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
KBAYQFWFCOOCIC-GNVSMLMZSA-N [(1s,4ar,4bs,7s,8ar,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methanol Chemical compound OC[C@@]1(C)CCC[C@]2(C)[C@H]3CC[C@H](C(C)C)C[C@H]3CC[C@H]21 KBAYQFWFCOOCIC-GNVSMLMZSA-N 0.000 description 3
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 3
230000002411 adverse Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
230000008569 process Effects 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical class OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
230000032683 aging Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003086 colorant Substances 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
125000006850 spacer group Chemical group 0.000 description 2
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical class O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical class C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 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
244000287680 Garcinia dulcis Species 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000000295 emission spectrum Methods 0.000 description 1
239000005329 float glass Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
229910052743 krypton Inorganic materials 0.000 description 1
DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000005336 safety glass Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical class OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Landscapes

Macromonomer-Based Addition Polymer (AREA)

CA000440212A 1983-11-02 1983-11-02 Compose adhesif polymerisable par rayonnement Expired CA1256243A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000440212A CA1256243A (fr)	1983-11-02	1983-11-02	Compose adhesif polymerisable par rayonnement

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000440212A CA1256243A (fr)	1983-11-02	1983-11-02	Compose adhesif polymerisable par rayonnement

Publications (1)

Publication Number	Publication Date
CA1256243A true CA1256243A (fr)	1989-06-20

Family

ID=4126426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000440212A Expired CA1256243A (fr)	1983-11-02	1983-11-02	Compose adhesif polymerisable par rayonnement

Country Status (1)

Country	Link
CA (1)	CA1256243A (fr)

1983
- 1983-11-02 CA CA000440212A patent/CA1256243A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-06-20	MKEX	Expiry

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